WO2003091223A1 - Pyrimidine derivative - Google Patents

Abstract

A pyrimidine derivative having the general formula (I): (I) wherein R1 and R3 each represent a hydrogen atom, a lower alkyl group or the like; R2 and R4 each represent an aryl group, a heterocyclic group or the like; A1 and A2 each represent an oxygen atom or the like; R5 represents a group having the formula: -D- R8, where D is a group having -NH- and the like and R8 is an aryl group or the like; R6 represents a hydrogen atom or the like, a pharmaceutically acceptable salt thereof, an ester thereof or another derivative thereof. The pyrimidine derivative exhibits excellent MLR inhibiting action.

Description

 Description Pyrimidine derivatives Technical field

 The present invention relates to a pyrimidine derivative having a mixed lymphocyte culture reaction (hereinafter, abbreviated as MLR) inhibitory action, a pharmacologically acceptable salt thereof, an ester thereof, or another derivative thereof. It relates to a drug contained as an active ingredient. Background art

 In the case of bone marrow transplantation and organ transplantation, rejection reactions to transplants are caused by the reaction between autologous lymphocytes on the recipient side and non-autologous cells in the transplanted tissue to activate and proliferate the lymphocytes. It is caused by eliminating attacks.

This rejection reaction can be attributed to 1) recognition of non-self cells, 2) increased expression of costimulatory molecules or production of proliferative cytokins on the surface of lymphocytes, 3) activation and proliferation of lymphocytes, 4) proliferation It is a multi-step reaction consisting of steps such as attacking the graft with lymphocytes that have been performed. Recognition of non-self cells by lymphocytes is performed through major histocompatibility complex (Maj or Histoco immediately at ibil Uy; MHC). Lymphocytes that are activated by recognizing non-self cells due to differences in MHC produce cytokins called inulin leukin 2 (hereinafter abbreviated as IL-2). Various immune cells are activated to proliferate. Activated lymphocytes activate proliferation of various immune cells via costimulatory molecules expressed on the membrane surface. Proliferative activated T cells, B cells, such as killer one T cell, attack eliminate transplanted lymphocytes' tissue cells ^{(IMMUN0BI0L0G Y 3 rd edi t ion} , 67).

MLR is considered to be a simple evaluation system that reflects the proliferative response of autologous lymphocytes to non-autologous lymphocytes in this rejection reaction. It is one. Some of the compounds found to be effective in suppressing transplant rejection, which have recently been found to be effective in this system It has become a Gaaka ^{(IM UNOBIOLOGY 3 rd edition, 505} ). Therefore, compounds that inhibit MLR are expected to be useful drugs that suppress rejection in bone marrow transplantation and organ transplantation and maintain long-term survival of transplanted bone marrow and organs.

 On the other hand, the experimental system for evaluating MLR is an experimental system that reflects cell-mediated immunity such as lymphocyte cell proliferation and cell killing activity, and humoral immunity such as antibody production. Is considered to be effective also for the following diseases involving excessive humoral immune function.

 Excessive cellular immunity and humoral immunity can be caused by chronic inflammatory diseases such as rheumatoid arthritis, or organ-specific autoimmune diseases such as multiple sclerosis, inflammatory bowel disease, dysuria, and glomeruli. Nephritis, primary biliary cirrhosis, chronic active hepatitis, pernicious anemia, Hashimoto's thyroiditis, atrophic gastritis, myasthenia gravis, psoriasis, and systemic erythematosus, a non-organ-specific autoimmune disease with Siedalen syndrome, It is thought to be involved in allergic diseases, rhinitis, asthma, and atopic dermatitis. [Imnmnol. Today, Vol. 16, 34-38, (1995); Science Vol. 260, 547-549, (1993); I. community, Vol. 3, 171-174, (1995); J. Exp. Med., Vol. 190, 995-1003, (1999); Kidney Int. 52, 52-59, (1997); J. Exp. Med., Vol. 185, 65-70, (1997), NANZANDO'S MEDICAL DICTIONARY, 797]. In defense, It is believed to show efficacy.

 From the above background, attempts have been made to find a compound having an excellent MLR inhibitory action. Disclosure of the invention

The present inventors conducted a sharp study on a derivative having an MLR inhibitory action. As a result, the pyrimidine derivative of the present invention has an excellent MLR inhibitory action, has low cytotoxicity, and is useful in bone marrow transplantation, organ transplantation, Inhibitor of transplant rejection, inhibitor of cancer cells by selective cell killing activity (eg, inhibitor of cancerous lymphocytes), or rheumatoid arthritis, an inflammatory disease, organ-specific autoimmunity Diseases (e.g., multiple sclerosis, inflammatory bowel disease, diabetes, glomerulonephritis, primary biliary cirrhosis, chronic active hepatitis, pernicious anemia, Hashimoto's thyroiditis, atrophic gastritis, myasthenia gravis, Psoriasis or siedare Prophylactic agent and Z or therapeutic agent (preferably, bone marrow) for organ-specific autoimmune diseases (for example, systemic lupus erythematosus) or allergic diseases (for example, rhinitis, asthma or atopic dermatitis). The present invention has been found to be useful as an agent for suppressing rejection of transplants in transplantation and organ transplantation, or as an agent for preventing or treating rheumatoid arthritis, or as a therapeutic agent).

(1) The present invention provides a compound represented by the general formula (I):

(I)

Or the general formula (I I)

 [Where,

R ¹ and R ³ are the same or different and are a hydrogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy lower alkyl group, a (mono-lower alkylamino) lower alkyl group, a (G lower alkylamino) lower alkyl group, an aryl An aryl group independently substituted by 1 to 5 groups or an arbitrary group selected from substituent group a,

R ² and R ⁴ are the same or different and are independently an aryl group, a heterocyclic group, an aryl group or a substituent group which is independently substituted with 1 to 5 arbitrary groups selected from a substituent group a. represents a heterocyclic group which is independently substituted by 1 to 3 arbitrary groups selected from a, or R ² is the same as R ¹ or R ⁴ is the same or different as R ³ , including the carbon atoms to which they are each attached, saturated carbocyclic group, saturated heterocyclic group A saturated carbocyclic group independently substituted with 1 to 5 arbitrary groups selected from the substituent group a or a saturated heterocyclic group independently substituted with 1 to 3 arbitrary groups selected from the substituent group a Form a ring group,

A ¹ and A ² are the same or different and each have a formula NR ⁷ — (wherein, R ⁷ represents a hydrogen atom or a lower alkyl group) or an oxygen atom;

R ⁵ is a cycloalkyl group independently substituted with 1 to 5 arbitrary groups selected from a cycloalkyl group, an aryl group, a heterocyclic group, a lower alkylthio group, a substituent group a, An aryl group independently substituted with 1 to 5 arbitrary groups selected from substituent group a, a heterocyclic group independently substituted with 1 to 3 arbitrary groups selected from substituent group a, A group having the formula 1 D—R ⁸ , a group having the formula 1 CH ₂ —E—R ⁸ (wherein

 D represents a group having one NH—, an oxygen atom or a sulfur atom,

 E represents an oxygen atom, a sulfur atom or a single bond,

R ⁸ is a cycloalkyl group, an aryl group, a heterocyclic group, an aralkyl group, a cycloalkyl group independently substituted with 1 to 5 substituents selected from a substituent group a, and a substituent group a Selected from an aryl group independently substituted with 1 to 5 substituents, a heterocyclic group independently substituted with 1 to 3 substituents from any group selected from the substituent group a, or a substituent group a Represents an aralkyl group independently substituted with 1 to 5 arbitrary groups. ) Or the formula —A ³ — N = CR ⁹ R ^1Q (where

A ³ represents a group having the formula NR ¹¹ — (wherein R ¹¹ represents a hydrogen atom or a lower alkyl group) or an oxygen atom;

R ⁹ is any selected from a hydrogen atom, a lower alkyl group, a lower alkoxy lower alkyl group, a (mono-lower alkylamino) lower alkyl group, a (di-lower alkylamino) lower alkyl group, an aryl group or a substituent group a Represents an aryl group independently substituted by 1 to 5 groups,

R ^1Q represents an aryl group, a heterocyclic group, an aryl group substituted with 1 to 5 substituents independently from an arbitrary group selected from substituent group a, or an arbitrary group selected from substituent group a. Independently represents 1 to 3 substituted heterocyclic groups, or R ^lfl together with R ⁹ is independently substituted with 1 to 5 arbitrary groups selected from a saturated carbocyclic group, a saturated heterocyclic group and a substituent group a, including the carbon atom to which they are bonded. And 1 to 3 independently substituted saturated carbocyclic groups or a saturated heterocyclic group substituted with an arbitrary group selected from substituent group a. ),

R ⁶ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a (mono-lower alkylamino) lower alkyl group, a (di-lower alkylamino) lower alkyl group, an aralkyl group or an anilino group;

 Substituent group a is a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halogeno lower alkylthio group, a halogeno lower alkyloxy group, a cycloalkyl group, a hydroxy group, a carboxy group, a carboxymethyl group. , Lower alkoxycarbonyl, amino, mono-lower alkylamino, di-lower alkylamino, lower aliphatic acylamino, nitro, cyano, sulfonyl, lower alkylsulfonyl, octogeno lower alkylsulfonyl, aryl Sulfonyl group, heterocyclic group sulfonyl group, lower alkylsulfinyl group, arylsulfinyl group, dirubamoyl group, mono-lower alkyl force rubamoyl group, di-lower alkyl force rubamoyl group, lower alkyl (aryl) Rubamoyl group, ethylidenehydrazinocarbonyl group, rubamoyloxy group, mono-lower alkyl rubamoyloxy group, g-lower alkyl rubamoyloxy group, carbamoylamino group, mono-lower alkyl rubamoylamino group, g-lower alkyl rubamoylamino group Group, sulfonylamino group, lower alkylsulfonylamino group, aminosulfonyl group, mono-lower alkylaminosulfonyl group, di-lower alkylaminosulfonyl group, mono-cycloalkylaminosulfonyl group, mono-lower 7-alkoxy Lower alkylaminosulfonyl group, mono-lower alkoxycarbonyl lower alkylaminosulfonyl group, mono-l-rubamoyl lower alkylaminosulfonyl group, mono-lower aliphatic acetylaminosulfonyl group, hydro Xy represents a group consisting of a lower alkyl group, an oxo group, an aryl group, an aryloxy group and an aralkyl group. ]

And a pharmacologically acceptable salt thereof, an ester or other derivative thereof, and a pharmaceutical composition containing the same as an active ingredient. . In the above, preferably,

(2) In (1), a pyrimidine derivative having the general formula (I), a pharmaceutically acceptable salt thereof, an ester or other derivative thereof,

 (3) In (1), a pyrimidine derivative having the general formula (II), a pharmaceutically acceptable salt thereof, an ester or other derivative thereof,

 (4) In any one selected from (1) to (3),

R ¹ and R ³ are a hydrogen atom, a pyrimidine derivative or a pharmaceutically acceptable salt thereof,

(5) In any one of (1) through (3),

A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein R ¹ and R ³ are the same or different and are a lower alkyl group,

 (6) In any one selected from (1) to (3),

A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein R ¹ and R ³ are the same or different and are each a C ₂ alkyl group;

 (7) In any one selected from (1) to (3),

R ¹ and R ³ are a pyrimidine derivative or a pharmaceutically acceptable salt thereof, which is a methyl group,

(8) In any one of (1) to (3),

R ¹ and R ³ are the same or different and are selected from a lower alkoxy lower alkyl group, a (mono-lower alkylamino) lower alkyl group, a (di-lower alkylamino) lower alkyl group, an aryl group and a substituent group a. A pyrimidine derivative or a pharmaceutically acceptable salt thereof, which is an aryl group independently substituted by 1 to 5 groups

(9) In any one selected from (1) to (3),

R ¹ and R ³ are the same or different and are a aryl group or an aryl group independently substituted with 1 to 5 arbitrary groups selected from the substituent group a, or a pharmaceutically acceptable pyrimidine derivative thereof. salt,

 (10) In any one of (1) to (3),

R ² is the same or different as R ¹ and Z or R ⁴ is the same or different as R ³ , including the carbon atom to which they are each attached, saturated carbocyclic group, saturated heterocyclic group, substituted Base group a Forms a saturated carbocyclic group independently substituted with 1 to 5 groups by an arbitrary group selected from the group consisting of: or a saturated heterocyclic group independently substituted by 1 to 3 groups by an arbitrary group selected from the substituent group a A pyrimidine derivative or a pharmaceutically acceptable salt thereof,

 (11) In any one selected from (1) to (3),

R ² is together and / or R ⁴ and R ¹ together with R ^3, same or different, including the carbon atom to which each it we are attached, a benzene ring condensed with optionally c ₄ one c ₇ saturated carbocyclic group, 5- to 6-membered saturated heterocyclic group, 1 is five independently substituted with any group selected from substituent group a, a benzene ring condensed with optionally C ₄ one C ₇ saturated carbonates TamakiHajimemata is acceptable on a pyrimidine derivative or a pharmacologically to form a 5- or 6-membered saturated heterocyclic group substituted 1 to 3 independently any group selected from substituent group a,

(12) In any one of (1) to (3),

R ² together with R ¹ and / or in R ⁴ is together with R ^3, same or different, each including a carbon atom to which it we are attached, may be fused with a benzene ring C ₅ - C ₆ saturated carbocyclic group, tetrahydrothiophene ring group, tetrahydropyran ring group, piperidine ring group, benzene ring, which is independently substituted with 1 to 5 arbitrary groups selected from substituent group a A C ₅ -C ₆ saturated carbocyclic group which may be condensed or a tetrahydrothiophene ring, a tetrahydropyran ring or a piperidine ring group which is independently substituted by 1 to 3 groups selected from a substituent group a. Forming a pyrimidine derivative or a pharmacologically acceptable salt thereof,

 (13) In any one of (1) to (3),

R ² together with R ¹ and / or in R ⁴ is together with R ^3, same or different, each including a carbon atom to which it we are attached, may be fused with a benzene ring C ₅ - Forming a C ₅ —C ₆ saturated carbocyclic group which may be condensed with a benzene ring, which is independently substituted with 1 to 5 C ₆ saturated carbocyclic groups or any group selected from substituent group a A pyrimidine derivative or a pharmacologically acceptable salt thereof,

 (14) In any one of (1) to (3),

R ² together with R ¹ and R or R ⁴ together with R ³ , identical or different, each including the carbon atom to which they are attached, an indane group, 1,2,3,4-tetrahydro A naphthalene group or indane or 1, 2, 3, A pyrimidine derivative forming a 4-tetrahydronaphthylene group (the substituent is a group selected from the group consisting of a lower alkoxy group, a lower aliphatic acylamino group, a lower alkylsulfonyl group and a cyano group) or a pyrimidine derivative thereof; A pharmacologically acceptable salt, (15) in any one selected from (1) to (3),

R ² is together with R ¹ and Z or R ⁴ together with R ³ , identical or different, each including the carbon atom to which they are attached, an indane group, 1, 2, 3, 4— A pyrimidine derivative or a pharmaceutically acceptable salt thereof which forms an indane or 1,2,3,4-tetrahydronaphthylene group substituted with 1 to 3 tetrahydronaphthalene groups or lower alkoxy groups,

 (16) In any one selected from (1) to (9),

R ² and R ⁴ are the same or different and each independently represent an aryl group, a 5- to 6-membered heterocyclic group which may be condensed with a benzene ring, or an arbitrary group selected from substituent group a; A pyrimidine derivative or a 5- or 6-membered heterocyclic group which is independently substituted with 1 to 3 substituted aryl groups or an arbitrary group selected from substituent group a and which may be condensed with a benzene ring, or Pharmacologically acceptable salts,

 (17) (1) to (9) Force ^ In any one of the selected items,

R ² and R ⁴ are the same or different and are C ₆ —. Aryl group, furyl, cyenyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, vilanyl, pyridyl, 1,3-dioxolanyl or 1,3-dioxanyl group which may be condensed with a benzene ring, any group selected from substituent group a C ₆ —C _1Q aryl group independently substituted with 1 to 5 groups, or 1 to 3 independently substituted with any group selected from substituent group a, may be condensed with a benzene ring A pyrimidine derivative which is a furyl, chenyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, pyranyl, pyridyl, 1,3-dioxolanyl or 1,3-dioxanyl group or a pharmaceutically acceptable salt thereof, (18) (1) In any one selected from to (9),

1 ^ and 1 ⁴ are the same or different, phenyl group, naphthyl group, thienyl group, Ji Azoriru group, a pyridyl group, a quinolyl group, 1, 3-base Nzojiokizora group, optionally selected from Substituent Group a A phenyl or naphthyl group independently substituted with 1 to 5 groups, or 1 to 3 independently substituted with any group selected from substituent group a A pyrimidine derivative or a pharmacologically acceptable salt thereof, which is a chenyl, thiazolyl, pyridyl, quinolyl, or 1,3-benzodioxolanyl group,

 (19) In any one selected from (1) to (9),

R ² and R ⁴ may be the same or different and are phenyl, naphthyl, phenyl, thiazolyl, pyridyl, quinolyl, 1,3-benzodioxolanyl, or 1 to 3 substituents; Phenyl, naphthyl, phenyl, thiazolyl, pyridyl, quinolyl or 1,3-benzodioxolanyl group (the substituent is a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group, a nitro group , A cyano group, a lower alkoxycarbonyl group, an aliphatic acylamino group, a lower alkylsulfonyl group, an aminosulfonyl group, a mono-lower alkylaminosulfonyl group, a monocycloalkylaminosulfonyl group and a di-lower alkylaminosulfonyl group A pyrimidine derivative or a pharmaceutically acceptable derivative thereof. Salt,

 (20) In any one selected from (1) to (9),

R ² and R ⁴ are the same or different and are phenyl, 2,3,6-trifluorophenyl, 4-methylsulfonylphenyl, 4-ethylsulfonylphenyl, 2,6-difluorophenyl, 2,3 Dimethoxyphenyl, 2,5-dimethoxyphenyl, 2-, 3- or 4-cyanophenyl, 3,4-dimethoxy-6-dimethoxyphenyl, 4-methoxycarbonylphenyl, 4-ethoxycarbonylphenyl, 4-phenyl Cetylaminophenyl, 2-chloro-5-nitrophenyl, 3-hydroxy-6-nitrophenyl, 4-aminosulfonylphenyl, 4-methylaminosulfonylphenyl, 4-ethylaminosulfonylphenyl, 4-propylamino Sulfonylphenyl, 4-cyclopropylaminosulfonylphenyl, 4-dimethylaminosulfonylphenyl, 2- Quinoline-1-yl, pyridine-3-1-fir, pyridine-41-yl, thiophene-21-yl, 1,3-benzodioxolan-6-yl, 1,3-benzodioxolan _ 7-yl, 5-nitro-1,3-benzodioxolan _ 6— ^ f, 6-nitro-1,3,1-benzodioxolan-7-1 ^ f, 5-chloro-1, 3-Benzodioxolan-6-yl, 6-clo mouth — 1,3 Benzodioxolan-1 7-yl or 2,4-dimethyl-1,3-thiazo —Ru 5-yl pyrimidine derivative or a pharmacologically acceptable salt thereof, (21) In any one selected from (1) to (9),

R ² and R ⁴ are the same or different and are phenyl, 4-cyanophenyl, 4-methylsulfonylphenyl, .4-ethylsulfonylphenyl, 4-acetylaminophenyl, 3,4-dimethoxy-6-nitrophenyl 4-aminosulfonylphenyl, 4-methylaminosulfonylphenyl, 4-ethylaminosulfonylphenyl, 4-propylaminosulfonylphenyl, 4-cyclopropylaminosulfonylphenyl, 4-dimethylaminosulfonylphenyl, 4-dimethylaminosulfonylphenyl, A pyrimidine derivative or a pharmacologically acceptable salt thereof, which is a pyridine-14-yl or thiophene-12-yl group,

 (22) In any one selected from (1) to (21),

A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein A ¹ and A ² are —NH— groups;

 (23) In any one selected from (1) to (21),

Wherein A ¹ and A ² are pyrimidine derivatives or pharmaceutically acceptable salts thereof, which are oxygen radicals, (24) in any one selected from (1) to (23),

R ⁵ is independently selected from a cycloalkyl group, an aryl group, a heterocyclic group, a cycloalkyl group substituted with 1 to 5 arbitrary groups selected from a substituent group a, and a substituent group a A pyrimidine derivative, which is a heterocyclic group independently substituted with 1 to 3 aryl groups or 1 to 3 independently substituted with an arbitrary group selected from substituent group a, or a pharmacologically acceptable derivative thereof, Acceptable salts,.

(25) In any one selected from (1) to (23),

R ⁵ is a pyrimidine derivative or a pharmaceutically acceptable salt thereof, which is a cycloalkyl group or a heterocyclic group,

 (26) In any one selected from (1) to (23),

R ⁵ is C ₃ . ₆ a pyrimidine derivative or a pharmacologically acceptable salt thereof, which is a 5- or 6-membered complex ring group which may be condensed with a cycloalkyl group or a benzene ring,

 (27) In any one selected from (1) to (23),

Pyrimidi wherein R ⁵ is a cyclopropyl group, an indolyl group or an indolinyl group Derivatives or pharmacologically acceptable salts thereof,

 (28) In any one selected from (1) to (23),

A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein R ⁵ is a group having the formula —D—R ⁸ (wherein R ⁸ has the same meaning as described above);

 (29) In (28),

 D is a pyrimidine derivative having one NH— or a pharmacologically acceptable salt thereof,

(30) In any one selected from (28) or (29), R ⁸ is a C _s -C _1Q aryl group, a 5- or 6-membered aromatic heterocyclic group which may be condensed with a benzene ring, C ₆ —C _1Q aryl group independently substituted with 1 to 5 arbitrary groups selected from substituent group a or 1 to 3 independently selected from any group selected from substituent group a A substituted pyrimidine derivative or a pharmacologically acceptable salt thereof, which is a 5- or 6-membered aromatic heterocyclic group which may be condensed with a benzene ring,

(31) In any one selected from (28) or (29), R ⁸ is a C ₆ -C 1 _Q aryl group, a pyridyl group, a phenyl group, a benzoyl group, a benzodioxolanyl group, a benzodioxanyl group or C ₆ — C, which is independently substituted with 1 to 3 arbitrary groups selected from the substituent group a. A pyrimidine derivative which is an aryl group or a pharmacologically acceptable salt thereof,

(32) In any one selected from (28) and (29), R ⁸ represents a phenyl group, a pyridyl group, a phenyl group, a benzodioxolanyl group, a benzodioxanyl group, or one to three substituted groups. A pyrimidine derivative which is a phenyl group substituted with a group (the substituent is a group selected from a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group and an aryl group); Its pharmacologically acceptable salts,

 (33) In any one selected from (28) or (29),

R ⁸ is phenyl, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluoro Phenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,3,4-trifluoro Phenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-ethoxyphenyl, 2-methylthiophenyl, 3,5-dimethoxyphenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 2-fluoro-4-methylphenyl, 2-fluoro- 5-Methylphenyl, 2-fluoro-5-trifluoromethylphenyl, 2-methoxy-5-methylphenyl, 2-methoxy-5-t-butylphenyl, 2-fluoro-4-methoxyphenyl, 4-fluoro-3-methoxyphenyl, 2-methoxy 5-phenylphenyl, 1,3-benzodioxolan-5-yl, 1,4-benzodioxane-1 6-yl or pyridi A pyrimidine derivative which is a 3-yl group or a pharmacologically acceptable salt thereof,

(34) In any one selected from (28) or (29), R ⁸ is a pyrimidine derivative or a pharmacologically acceptable salt thereof, which is a phenyl or 2-methoxyphenyl group.

 (35) In any one selected from (1) to (34),

R ⁵ is a group having the formula: A ³ —N = CR ⁹ R ^1Q (where A ³ , R ⁹ and R ^{1 ()} have the same meanings as described above) ′. Or a pharmacologically acceptable salt thereof, (36)

A ³ is a pyrimidine derivative having —NH— or a pharmacologically acceptable salt thereof,

 (37) In subsection (35) or (36),

R ⁹ is acceptable salts pyrimidine derivative or a pharmacologically a methyl group or a hydrogen atom, (38) In any one selected from (35) to (37), R ^1D is, phenyl, 4 —Cyanophenyl, 4-methylsulfonylphenyl, 4—Acetylaminophenyl, 3,4-dimethoxy-6-2-nitrophenyl, pyridin-4-yl or pyrimidine derivative which is a thiophen-12-yl group or its pharmacology Above acceptable salts,

(39) In any one of (1) to (35), R ¹ ", together with R ⁹ , is the same or different and includes an indane group, a 1,2,3,4-tetrahydronaphthalene group or a lower alkoxy group, each containing a carbon atom to which they are bonded; A pyrimidine derivative or a pharmacologically acceptable salt thereof, which forms a 3-substituted indane or 1,2,3,4-tetrahydronaphthalene group;

 (40) In any one selected from (1) to (39),

R ⁵ is a pyrimidine derivative or a pharmacologically acceptable salt thereof, which is a hydrogen atom.

R ⁶ is a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a (mono-lower alkylamino) lower alkyl group, a (di-lower alkylamino) lower alkyl group or an aralkyl group, a pyrimidine derivative or a pharmaceutically acceptable derivative thereof. Salt,

 (42) In any one selected from (1) to (39),

R ⁶ is a lower alkyl group, a lower alkoxy group or an aralkyl group, a pyrimidine derivative or a pharmaceutically acceptable salt thereof

 (43) In any one selected from (1) to (39),

R ⁶ is a C, —C ₂ alkyl group, a C ₂ alkoxy group or a benzyl group, a pyrimidine derivative or a pharmaceutically acceptable salt thereof,

 (44) In (1),

 1- (4-pyridinyl)-1-ethanone N- (2- (2-fluoroalanilino) -6- {2- [2- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidyl) hydrazone,

 1- (4-pyridinyl) -triethanone N- (2-anilino-6_ {2-[(4- (pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

 1- (4-pyridinyl) -toethanone N- (2- (3-methoxyanilino) -6_ {2- [to (4-pyridinyl) ethylidene] drazino} -4- -pyrimidinyl) hydrazone,

 Tri (4-methylsulfamoylofenyl)-1-ethanone N- (2-anilino-1-6- [2- [1- (4-methylsulfamoylofenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone,

1 one ₍₄ one-pyridyl) Single Bok ethanone N-(2- (benzo [1, 3] Jiokiso Ichiru - 5 Iruami Bruno) one 6- {2- [1- (4-pyridyl) Echiriden] hydrazino} - 4-pyrimidinyl) hydrazo ,

 1_ (4-ethylsulfonylphenyl) -1 -ethanone-(2-anilino-6- {2- [1- (4-ethylsulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

 1- (4-cyclopropylsulfamoylofenyl) -triethanone N- (2-anilino —6- {2-[(tri (4-cyclopropylsulfamoylofenyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone,

 1-(4-Methylsulfamoyleneyl) -1 -Ethanone N_ (2- (2,4,5-trifluoranilino) -1-6- (2- [1- (4-methylsulfamoyl) Roofenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

 1- (4-Methylsulfamoylofenyl) -triethanone N- (2- (2-fluoroallylinyl) 1 6- {2- [1- (4-Methylsulfamoylofenyl) ethylidene] hydrazino} -4 -pyrimidinyl) hydrazone,

 4- (Ethylsulfamoylofenyl) -1 -Ethanone N- (2-anilino-6- {2-[(4- (4-ethylsulfamoylofenyl) ethylidene] hydrazino} hydrazino} -4-pyrimidinyl ) Hydrazone,

 1- (4-Methylsulfamoylphenol) -1 -Ethanone N- (2- (2,3,4-trifluoroanilino)-6- {2- [1- (4-methylsulfamoyl) Roofenyl) ethylidene] hydrazino}-4-pyrimidinyl) hydrazone,

 1- (4-Methylsulfamoylofenyl) -triethanone N- (2- (2-Fluoro-4-chloroanilino) 1 6- {2-[tri (4-methylsulfamoylofenyl) ethylidene] Hydrazino} -4-pyrimidinyl) hydrazone,

 1- (4-Methylsulfamoylfurenyl) -triethanone N- (2- (3-Methoxyanilino) -1-6- (2- [1- (4-Methylsulfamoyl-phenyl) ethylidene] hydrazino } -4-pyrimidinyl) hydrazone,

 Tri (4-methylsulfamoylofenyl) -triethanone N- (2-anilino-5-ethoxy) 6- {2- [1- (4-methylsulfamoylofenyl) ethylidene] hydrazide} -4 -Pyrimidinyl) hydrazone,

(4-Methylsulfamoylphenylethanone N- (2- (3,5-difluoroa Nirino) -6-{2-[H4-,

4-Pirimigere) hydrazone,

 1- (4-methylsulfamoylphenyl) -triethanone Ν- (2- (3,4,5-trifluoroaluminino) -6- {2- [1-[(4-methylsulfamoylphenyl) ethylidene) ] Hydrazino} _4-pyrimidinyl) hydrazone,

 1- (4-methylsulfamoylphenyl) -triethanone Ν- (2-anilino-15-benzyl-6- {2- [1- [4- (4-methylsulfamoylphenyl) ethylidene] hydrazino}-4- Pyrimigel) hydrazone,

 1- (4-Methylsulfamoylphenyl) -toluenenon- (2- (3,4-difluoroa-2rino) -6- {2- [1- [4- (4-Methylsulfamoylphenyl) ethylidene] hydrazino) 4-pyrimidinile) hydrazone,

 Tri (4-methylsulfamoylphenyl) -triethanone Ν- (2- (3-fluoroanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4-pi Limidinyl) hydrazone,

 Tri (4-methylsulfamoylphenyl)-1-ethanone Ν- (2- (benzo [1,3] dioxol-5-yl-amino) -6- {2- [tri (4-methyl Sulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

 Tri- (4-methylsulfamoylphenyl) -triethanone Ν- (2- (2,4-difluora-4-pyrimidinyl) hydrazone,

 1- (4-Methylsulfamoylphenyl) -toluene non-Ν- (2- (2-methoxyanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] Hydrazino 4-pyrimidinyl) hydrazone,

 1- (4-methylsulfamoylphenyl) -toethanone Ν- (2- (2-fluoro-5-chloroanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

1- (4-Methylsulfamoylphenyl) -toluenenon- (2- (4-chloroanilino) -6- {2-[(4- (4-methylsulfamoylphenyl) ethylidene] hydrazino) }-4-pyrimidinyl) hydrazone, Tri (4-methylsulfamoylphenyl) -triethanone N- (2- (2-fluoro-4-methoxymethoxylinino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino } -4-pyrimidinyl) hydrazone,

 Tri- (4-methylsulfamoylphenyl) -triethanone N- (2- (3-methoxy-4-fluoroalilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrid Razino} -4-pyrimidinyl) hydrazone and

 Tri (4-ethylsulfamoylphenyl) -triethanone N- (2- (3-fluoroarylamino) _6-{2- [1- (4-ethylsulfamoylphenyl) ethylidene] hydrazino} -4 -pyrimidinyl) hydrazone

A compound selected from the group consisting of:

 (4 5) (1) to (4 4) Force ^ A pharmaceutical composition containing the compound according to any one of the selected items, a pharmacologically acceptable salt thereof, an ester thereof or another derivative thereof as an active ingredient. ,

 (46) The pharmaceutical composition according to (45), wherein the pharmaceutical composition is a composition for inhibiting a mixed lymphocyte culture reaction.

 (47) The pharmaceutical composition suppresses rejection of grafts in bone marrow transplantation, organ transplantation, etc. or prevents inflammatory diseases, organ-specific autoimmune diseases, non-organ-specific autoimmune diseases or allergic diseases, and Z Or a pharmaceutical composition according to (45), which is a composition for treatment.

 (48) The pharmaceutical composition is rheumatoid arthritis, multiple sclerosis, inflammatory bowel disease, diabetes, glomerulonephritis, primary biliary cirrhosis, chronic active hepatitis, pernicious anemia, Hashimoto's thyroiditis, atrophic gastritis The pharmaceutical composition according to (45), which is a composition for preventing and treating Z or treating myasthenia gravis, psoriasis, siedalen syndrome, systemic lupus erythematosus-death, rhinitis, asthma or atopic dermatitis.

 (49) The pharmaceutical composition according to (45), wherein the pharmaceutical composition is a composition for suppressing cancer cells.

 (50) The pharmaceutical composition according to (45), wherein the pharmaceutical composition is a composition for suppressing cancerous lymphocytes.

(51) The pharmaceutical composition is rejected for transplantation in bone marrow transplantation, organ transplantation, etc. A pharmaceutical composition according to (45), which is a composition for inhibiting or responding to a disease or preventing and / or treating rheumatoid arthritis.

 (52) Use of the compound according to any one of (1) to (44), a pharmacologically acceptable salt thereof, an ester thereof, or another derivative for producing a pharmaceutical composition. ,

 (53) The use according to (52), wherein the pharmaceutical composition is a composition for inhibiting a mixed lymphocyte culture reaction.

 (54) The pharmaceutical composition suppresses rejection of grafts in bone marrow transplantation, organ transplantation, etc. or prevents inflammatory diseases, organ-specific autoimmune diseases, non-organ-specific autoimmune diseases or allergic diseases, and Z or The use according to (52), which is a composition for treatment.

 (55) The pharmaceutical composition is rheumatoid arthritis, multiple sclerosis, inflammatory bowel disease, diabetes, glomerulonephritis, primary biliary cirrhosis, chronic active hepatitis, pernicious anemia, Hashimoto's thyroiditis, atrophic gastritis, The use according to (52), which is a composition for the prevention and Z or treatment of myasthenia gravis, psoriasis, Siedalen syndrome, systemic lupus erythematosus-death, rhinitis, asthma or atopic dermatitis,

 (56) The use according to (52), wherein the pharmaceutical composition is a composition for suppressing cancer cells.

 (57) The use according to (52), wherein the pharmaceutical composition is a composition for suppressing cancerous lymphocytes,

 (58) The use according to (52), wherein the pharmaceutical composition is a composition for suppressing rejection of a graft in bone marrow transplantation / organ transplantation or preventing or treating rheumatoid arthritis.

 (59) Administering a pharmacologically effective amount of the compound according to any one of (1) to (44), a pharmacologically acceptable salt thereof, an ester or other derivative thereof to a warm-blooded animal Bone marrow transplantation11 Methods for suppressing rejection of graft

(60) The pharmacologically effective amount of the compound according to any one of (1) to (44), a pharmacologically acceptable salt thereof, an ester thereof, or another derivative thereof is heated. Prevention and / or treatment method of diseases to be administered to blood animals,

 (61) The method according to (60), wherein the disease is an inflammatory disease, an organ-specific autoimmune disease, a non-organ-specific autoimmune disease or an allergic disease.

 (62) The disease is rheumatoid arthritis, multiple sclerosis, inflammatory bowel disease, diabetes, glomerulonephritis, primary biliary cirrhosis, chronic active hepatitis, pernicious anemia, Hashimoto's thyroiditis, atrophic gastritis, severe muscle disease The method according to (60), which is asthenia, psoriasis, Siedalen syndrome, systemic lupus erythematosus, rhinitis, asthma or atopic dermatitis.

 (63) The method according to (60), wherein the disease is rheumatoid arthritis.

 (64), (1) to (44) a pharmacologically effective amount of the compound according to any one of the above, a pharmacologically acceptable salt thereof, an ester or other derivative thereof, and a warm-blooded animal. A method for suppressing cancer cells to be administered to

 (65) The method according to (64), wherein the cancer cells are lymphocytes that have undergone cancer treatment.

 (66) The method according to any one of (59) to (65), wherein the warm-blooded animal is a human

Can be mentioned.

In the above formula, RR ³ , R ⁶ , RR \ R ¹¹ and the lower alkyl group in the definition of the substituent group a include, for example, methyl, ethyl, propyl, isopropyl, butyl, isoptyl, s-butyl, t-butyl. , Pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2, 2- 1 to 6 carbon atoms such as dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1-ethylbutyl or 2-ethylbutyl groups a linear or branched alkyl group, preferably a C _t one C ₄ alkyl group, and more preferably is an C ₂ alkyl group, most preferably, It is a methyl group.

In the above formula, R ⁶ and the lower alkoxy group in the definition of the substituent group a are the lower alkoxy groups Alkyl group bonded to an oxygen atom, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentoxy, iso-ventoxy, 2-methylbutoxy, 1-methylbutoxy Ethylpropoxy, 2-ethylpropoxy, neopentoxy, hexyloxy, 4-methylpentoxy, 3-methylpentoxy, 2-methylpentoxy, 3,3-dimethylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethyl A straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms such as butoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy or 2,3-dimethylbutoxy; _{It is a 4} alkoxy group, more preferably a 1 C ₂ alkoxy group, and most preferably a methoxy group.

In the above formula, the lower alkoxy lower alkyl group in the definition of R ¹ , R ³ , R ⁶ and R ^{9 represents} a group in which one of the lower alkoxy groups is bonded to the lower alkyl group, for example, methoxymethyl, Ethoxymethylile, propoxymethyl, isopropoxymethyl, butoxymethyl, isobutoxymethyl, s-butoxymethyl, t-butoxymethyl, 2-methoxyethyl, 2-ethoxyxetil, 2-propoxyshetyl, 2-propoxyxethyl, 2-butoxyxethyl, 2-I-butoxyxetil, 2- (s-butoxy) ethyl, 2- (t-butoxy) ethyl, 1-methoxyethyl, 1-ethoxyxyl, 1-Proboxixyl, 1-Iproxoxethyl, 1-butoxyxethyl, 1 1-isobutoxyshethyl, 1- (s-butoxy) ethyl, 1- (t-butoxy) ethyl or C, such as 3-isopropoxy-propyl group, one C ₆ alkoxy C, is an C ₆ Al kill groups, preferably one C ₄ alkoxy (: an alkyl group, and more favorable suitable one C ₂ An alkoxy-alkyl group, most preferably a methoxymethyl group.

In the above formula, the mono-lower alkylamino group in the definition of the substituent group a represents a group in which one lower alkyl group is bonded to an amino group, for example, methylamino, ethylamino, propylamino, isopropylamino, butylamino, Isoptylamino, s-butylamino, t-butylamino, pentylamino, isopentyl W

20 amino, 2-methylbutylamino, neopentylamino, 1-ethylpropylamino, hexylamino, isohexylamino, 4-methylpentylamino, 3-methylpentylamino, 2-methylpentylamino, 1- Methylpentylamino, 3,3-dimethylbutylamino, 2,2-dimethylbutylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,3-dimethyl Mono (such as butylamino or 2-ethylbutylamino) is an alkylamino group, preferably a mono C ₄ , 1 C ₄ alkylamino group, and more preferably a mono 1 C ₂ alkylamino group, and most preferably a Mechiruamino group. in the formula, (mono- lower Arukiruamino) in the definition of RR \ R ⁶ and R ⁹ lower The alkyl group represents a group in which one of the mono-lower alkylamino groups is bonded to the lower alkyl group, for example, methylaminomethyl, ethylaminomethyl, propylaminomethyl, isopropylaminomethyl, butylaminomethyl, Isobutylaminomethyl, sec-butylaminomethyl, t-butylaminomethyl, 2-methylaminoethyl, 2-ethylaminoethyl, 2-propylaminoethyl, 2-isopropylaminoethyl, 2-butylaminoethyl, 2 _Isobutylaminoethyl, 2- (s-butylamino) ethyl, 2- (t-butylamino) ethyl, 1-methylaminoethyl, 1-ethylaminoethyl, 1-propylaminoethyl, 1-isopropylaminoethyl, 1 1-butylaminoethyl, 1-isobutylaminoethyl, 1- (s-butylamino ) Ethyl, 1- (t-butylamino) ethyl is a (mono-C ₆ alkylamino) -C ₆ alkyl group such as a 3-isopropylaminopropyl group, and is preferably (mono-C ₄ alkylamino) C i is an C ₄ alkyl group, more preferably a - a (mono d-C ₂ Arukiruamino) one C ₂ alkyl group, most preferably a methyl § amino methyl group.

In the above formula, the di-lower alkylamino group in the definition of the substituent group a indicates a group in which two of the lower alkyl groups are bonded to an amino group, such as dimethylamino, Ruamino, N- Echiru -N- Mechiruamino, di like dipropylamino, Kishiruamino group Jibuchiruamino, to dipentyl § amino or di - is C i one C ₆ Arukiruamino group, preferably, di C, one C ₄ alkyl an amino group, more preferably a di - - (: ₂ Arukiruamino group, most preferably a Jimechiruamino group.

In the above formula, the (di-lower alkylamino) lower alkyl group in the definition of RR ³ , R ⁶ and R ^{9 represents} a group in which one of the di-lower alkylamino groups is bonded to the lower alkyl group; For example, dimethylaminomethyl, dimethylaminomethyl, (N-ethyl-N-methylamino) methyl, dipropylaminomethyl, dibutylaminomethyl, 2-dimethylaminoethyl, 2-dimethylaminoethyl, 2- (N-ethyl) —N-methylamino) ethyl, 2-dipropylaminoethyl, 2-dibutylaminoethyl, 1-dimethylaminoethyl, 1-ethylaminoethyl, 1- (N-ethylamino-methylamino) ethyl, 1-dipropyl A (di-d-C ₆ alkylamino) -C ₆ alkyl group such as aminoethyl or 1-dibutylaminoethyl group; - A C ₄ Arukiruamino) is an C ₄ alkyl group, more preferably a (di one C ₂ Arukiruamino) one C ₂ alkyl group, most preferably a dimethyl § amino methyl.

In the above formula, RR ² , R ³ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , R ^1Q and a group selected from the aryl group and the substituent group a in the definition of the substituent group a. The aryl moiety of the aryl group substituted with 1 to 5 is, for example, an aromatic hydrocarbon group having 6 to 14 carbon atoms such as phenyl, indenyl, naphthyl, phenanthrenyl, anthracenyl or fluorenyl group. Yes, preferably C ₆ —. Aryl group, more preferably phenyl or naphthyl group, and most preferably phenyl group.

In the above ^{formulas, R 2, R 4, RKR} s and R ^{1 (1} of the 1 to 3 heterocyclic group substituted with a substituent in the heterocyclic group and substituent group from a to selected a group of defined The heterocyclic moiety is a 5- to 7-membered heterocyclic group containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms, For example, furyl, cynyl, pyrrolyl, azepinyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxazadiazolyl, triazolyl, tetrazolyl, thiadiazolyl, pyranyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl Aromatic heterocyclic groups such as, tetrahydropyranyl, tetrahydrothenyl, morpholinyl, thiomorpholinyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, pyrazolidinyl, piberidinyl, piperazinyl, oxazolidinyl, isoxazolidinyl, thiazolidinyl, pyrazolidinyl or pyrazolidinyl, pyrazolidinyl or pyrazolidinyl Such a partially or completely reduced type saturated heterocyclic group. Benzothienyl, benzothiazolyl, benzoxazolyl, isobenzofuranyl, quinolyl, 1,3-benzodioxolanyl, benzodioxane, oxanyl indolyl, isoindolyl or the like. And an indolinyl group.

In RR ⁴ and R ^lfl , preferably a 5- or 6-membered heterocyclic group which may be condensed with a benzene ring, more preferably furyl, phenyl, pyrrolyl which may be condensed with a benzene ring, Pyrazolyl, imidazolyl, thiazolyl, pyranyl, pyridyl, 1,3-dioxolanyl or 1,3-dioxanyl group, more preferably thienyl group, thiazolyl group, pyridyl group, quinolyl group or 1,3-benzodioxolael And further more preferably a phenyl group, a thiazolyl group, a pyridyl group, a quinolyl group or a 1,3-benzodioxolar group, more preferably a pyridin-3-yl or pyridine group 1 4 1 ^ f, thiophene 1-2-yl, 1, 3-benzodioxolan-6-yl, 1, 3-benzodioxolan-1-7 -yl or 1,3-thiazole-5-yl group so Ri, and most preferably a pyridine one 4-I le or Chiofue Hmm 2 Iru group.

R ⁵ is preferably a 5- or 6-membered heterocyclic group which may be condensed with a benzene ring, more preferably an indolyl or indolinyl group, and most preferably one monoindolinyl group. R ⁸ is preferably a 5- or 6-membered heterocyclic group which may be condensed with a benzene ring, more preferably pyridyl, phenyl, 1,3-benzodioxoral or benzodiazo. It is a xanyl group, most preferably a pyridine-13-yl, 1,3-benzodioxolan-15-yl or 1,4-benzodioxane-16-yl group. In the above formula, R ² is together with R ¹ , R ⁴ is together with R ³ , and Z or R ^1Q is together with R ⁹ , each containing a carbon atom to which they are bonded. The saturated carbocyclic moiety of the saturated carbocyclic group substituted by 1 to 5 groups selected from the ring group and the substituent group a is, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane Such a saturated carbocyclic group having 3 to 10 carbon atoms. Further, the above-mentioned saturated carbocyclic group is a 5, 6, 7, 8-tetrahydroisoquinoline group which may be condensed with another cyclic group such as a benzene ring / heterocyclic ring. In such a saturated carbocyclic group, preferably a benzene ring condensed with a good C ₄ one C ₇ saturated carbocyclic group which may, more preferably, may be condensed with a benzene ring c ₅ - c _{It is a 6-} saturated carbocyclic group, most preferably an indane or 1,2,3,4-tetrahydronaphthalene group. In the above, R ² is together with R ¹ , R ⁴ is together with R ³ , and Z or R ^1Q is together with R ⁹ , each including a carbon atom to which they are bonded, and a saturated heterocyclic ring The saturated heterocyclic moiety of the saturated heterocyclic group substituted with 1 to 3 substituents with a group selected from the group and the substituent group a is, for example, trahydropyran, tetrahydrothiophene, morpholine, thiomorpholine, pyrrolidine , Pyrroline, imidazolidine, pyrazolidine, piperidine, piperazine, oxazolidine, isoxazolidine, thiazolidine, villazolidine, dioxolan or dioxane, preferably a 5- or 6-membered saturated heterocyclic group, and most preferably Is a tetrahydrothiophene ring group, a tetrahydrobiran ring group or a piperidine ring group. In the above formula, R ⁵ , R ⁸ and the cycloalkyl group in the definition of the substituent group a and the cycloalkyl portion of the cycloalkyl group substituted with 1 to 5 groups selected from the substituent group a are, for example, And a saturated carbocyclic group having 3 to 10 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norpolnyl or adamantyl. Further, the cycloalkyl group may be condensed with another cyclic group such as a benzene ring, and is, for example, indanyl, benzocyclohexyl or benzocycloheptyl. In R ⁵ , preferably C ₃ —. _A cycloalkyl group, most preferably a cyclopropyl group, and in R ⁸ and the substituent group a, a C ₅ —C ₆ cycloalkyl group, most preferably a cycloalkyl group. It is a hexyl group.

In the above formula, the aralkyl part of the aralkyl group substituted with 1 to 5 aralkyl groups and a group selected from the substituent group a in the definition of R ⁶ , R ⁸ and the substituent group a is the lower group of the aryl group. Represents a group to which an alkyl group is bonded, such as benzyl, α-naphthylmethyl,] 3-naphthylmethyl, indenylmethyl, diphenylmethyl, triphenylmethyl, 1-phenethyl, 2-phenyl, 1-naphthylethyl, 2-naphthylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-naphthylpropyl, 2-naphthylpropyl, 3-naphthylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl , 1 naphthyl butyl, 2 naphthyl butyl, 3 naphthyl butyl, 4 naphthyl butyl 1 1-pentyl pentyl, 2 _ pentyl pentyl, 3-pentyl pentyl, 4-pentyl pentyl, 5-pentyl pentyl, 1-naphthyl pentyl, 2- naphthyl pentyl, 3-naphthyl pentyl, 4-naphthyl pentyl, 5-naphthylpentyl, 1-phenylhexyl, 2-phenylhexyl, 3-phenylhexyl, 4-phenylhexyl, 5-phenylhexyl, 6-phenyl C ₇ —C _2fl aralkyl, such as hexyl, 1-naphthylhexyl, 2-naphthylhexyl, 3-naphthylhexyl, 4-naphthylhexyl, 5-naphthylhexyl or 6-naphthylhexyl And preferably a C ₇ -C _1Q aralkyl group, most preferably a benzyl group It is.

In the above formula, the octogen atom in the definition of the substituent group a is a fluorine, chlorine, bromine or iodine atom, preferably a fluorine atom or a chlorine atom, and most preferably a fluorine atom.

In the above formula, RR ³ and the halogeno lower alkyl group in the definition of the substituent group a represent a group in which the lower alkyl group is substituted with a halogen atom, for example, trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, dibromomethyl, Fluoromethyl, 2,2,2-Trifluoroethyl, 2,2,2-Trifluoroethyl, 2-Promoethyl, 2-Chloroethyl, 2-Fluoroethyl, 2-Eodoethyl, 3-Chloropropyl, 4-Fluorobutyl, 6 - hexyl Yodo or 2, 2 - halogeno one C ₆ alkyl groups such as Jiburomoechiru group, preferably, halogenoalkyl - a Ji ₄ Arukiru group, more preferably a halogeno - an alkyl group, more preferably, Furuoro - alkyl or black hole is an C ₂ alkyl group, most preferably, Torifuruo It is a methyl group.

In the above formula, R ⁵ and the lower alkylthio group in the definition of the substituent group a represent a group in which the lower alkyl group is bonded to a sulfur atom, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, S-butylthio, t-butylthio, pentylthio, isopentylthio, 2-methylbutylthio, neopentylthio, hexylthio, 4-methylpentylthio, 3-methylpentylthio, 2-methylpentylthio, 3,3-dimethylbutyl 1 to 6 carbon atoms such as thio, 2,2-dimethylbutylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio or 2,3-dimethylbutylthio a linear or branched alkylthio group, preferably a c "c ₄ Arukiruchio group, more preferred Is one c ₂ alkylthio group, and most preferably, Ru der methylthio group. In the above formula, the octogeno lower alkylthio group in the definition of the substituent group a indicates a group in which a halogen atom is substituted on the lower alkylthio group, for example, trifluoromethylthio, trichloromethylthio, difluoromethylthio, dichloromethylthio. , Dibumomethylthio, fluoromethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-bromoethylthio, 2-chloroethylthio, 2-fluoroethylthio Chiruchio, 2 ® - Doechiruchio, 3 black port propylthio, 4- full O b butylthio, 6- Yodo cyclohexylthio or 2 to, 2-jib port Moechiruchio halogenoalkyl 〇 like group, - (- ₆ Arukiruchio group There, preferably a halogeno one ₍₄ § alkylthio group, more preferably a halogeno one C ₂ alkylthio group, yo Ri preferred Is Furuoro is an C ₂ alkylthio group or a click every mouth C c ₂ alkylthio group, most preferably a triflate Ruo b methylthio group.

In the above formula, the halogeno lower alkyloxy group in the definition of the substituent group a indicates a group in which the octa-lower lower alkyl group is bonded to an oxygen atom, for example, trifluoromethyloxy, trichloromethyloxy, difluoromethyloxy, Dichloromethyloxy, dibromomethyloxy, fluoromethyloxy, 2,2,2-trifluoroethyloxy, 2,2,2-trichloroethyloxy, 2-bromoethyloxy, 2-chloroethyloxy Cyloxy, 2-fluoroethyloxy, 2-chloroethyloxy, 3-chloropropyloxy, 4-fluorobutyloxy, 6-hydroxyhexyloxy or 2,2-dibromoethyloxy halogeno C such as groups, - a C ₆ Arukiruokishi group, preferably a halogeno one C ₄ Arukiruokishi group, more preferably a halogen It is one c ₂ Arukiruokishi group, more preferably a Furuoro -c ^ al Kill group or black port one C ₂ Arukiruokishi group, most preferably a Torifuruoro Mechiruokishi group.

In the above formula, the lower alkoxy group in the definition of the substituent group a represents a group in which the lower alkoxy group is bonded to a carbonyl group, for example, methoxycarbonyl, Ethoxycarbonyl, propoxyl-proponyl, isopropoxyl-l-onil, butoxycarponyl, isobutoxyl-carponil, s-butoxyl-carponil, t-butoxyl-l-ponyl, pentoxycarponyl, isopentoxyl-carponyl, 2-methylbutoxyl-carponyl, neopentoxycarbonyl, Hexyloxy-capillonyl, 4-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1 A (C f Ce alkoxy) carbonyl group such as, 2,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl or 2,3-dimethylbutoxycarbonyl, preferably (C 1, 1C ₄ Alkoxy) an Karuponiru group, more preferably, (C, is an C ₂ alkoxy ') Karuponiru groups, and most preferably a methoxy local Poni Le group.

In the above formula, the lower aliphatic acylamino group in the definition of the substituent group a represents a lower aliphatic acyl group (a group in which a saturated or unsaturated chain hydrocarbon group is bonded to a carbonyl group, for example, acetyl, propionyl, A straight-chain or branched lower aliphatic acetyl group having 2 to 7 carbon atoms such as a butyryl, isoptyryl, valeryl, isovaleryl, bivaloyl, hexanoyl, acryloyl, methacryloyl or crotonyl group) is an amino group And represents, for example, acetylamino, propionylamino, butyrylamino, isoptyrylamino, valerylamino, isovalerylamino, pivaloylamino, hexanoylamino, acryloylamino, methacryloylamino, crotonylamino, etc. Straight-chain or 2-7 carbon atoms Edakusari a lower aliphatic Ashiruamino group, preferably, C ₂ - a C ₃ aliphatic Ashirua amino group, and most preferably a Asechiruamino group.

In the above formula, the lower alkylsulfonyl group in the definition of the substituent group a represents a group in which the lower alkyl group is bonded to a sulfonyl group. Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, Butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl, pentyl Sulfonyl, isopentylsulfonyl, 2-methylbutylsulfonyl, neopentylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, isohexylsulfonyl, 4-methylpentylsulfonyl, 3-methylpentylsulfonyl, 2-methylpentylsulfonyl 1,1-methylpentylsulfonyl, 3,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2 A C ₆ alkylsulfonyl group such as a 1,3-dimethylbutylsulfonyl or 2-ethylbutylsulfonyl group, preferably a C 1, 1C ₄ alkylsulfonyl group, more preferably 1 C ₂ Alkylsulfonyl group, most preferably methyls This is the Luho-yi group.

In the above formula, the halogeno lower alkylsulfonyl group in the definition of the substituent group a indicates a group in which the aforementioned halogeno lower alkyl group is bonded to a sulfonyl group, for example, trifluoromethylsulfonyl, trichloromethylsulfonyl, difluoromethyl Sulfonyl, dichloromethylsulfonyl, dimethyl monomethylsulfonyl, fluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, 2-bromoethylsulfonyl, 2-chloroethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 3-chloropropylsulfonyl, 4-fluorobutylsulfonyl, 6-hexylhexylsulfonyl or 2,2-dib halogeno C such as mouth Moe chill sulfonyl group, - with C ₆ alkyl sulfonyl Le group Ri, preferably a halogeno one C ₄ alkylsulfonyl group, more preferably a halogeno C, - a C ₂ alkylsulfonyl group, and more preferably, Furuoro one C ₂ alkylsulfonyl group or click port DC, - a C ₂ alkylsulfonyl group, most preferably a triflate Ruo b methylsulfonyl group.

In the above formula, the arylsulfonyl group in the definition of the substituent group a represents a group in which the aryl group is bonded to a sulfonyl group, such as phenylsulfonyl, indenylsulfonyl, naphthylsulfonyl, phenanthrenylsulfonyl, Anthracenyls An aromatic hydrocarbon sulfonyl group having 6 to 14 carbon atoms such as a rufonyl or fluorenylsulfonyl group, and preferably C ₆ —. An arylsulfonyl group, more preferably a phenyl or naphthylsulfonyl group, and most preferably a phenylsulfonyl group.

In the above formula, the heterocyclic group sulfonyl group in the definition of the substituent group a indicates a group in which the heterocyclic group is bonded to a sulfonyl group, for example, furylsulfonyl, phenylylsulfonyl, pyrrolylsulfonyl, azepinylsulfonyl, pyrazolyl Sulfonyl, imidazolylsulfonyl, oxazolylsulfonyl, isoxazolylsulfonyl, thiazolylsulfonyl, isothiazolylsulfonyl, 1,2,3-oxadiazolylsulfonyl, triazolylsulfonyl, tetrazolyl Aromatic heterocyclic groups such as sulfonyl, thiadiazolylsulfonyl, pyranylsulfonyl, pyridylsulfonyl, pyridazinylsulfonyl, pyrimidinylsulfonyl or pyrazinylsulfonyl groups sulfonyl group, tetrahydroviranylsulfonyl, tetrahydrocheni Rusulfonyl, morpholinylsulfonyl, thiomorpholinylsulfonyl, pyrrolidinylsulfonyl, pyrrolinylsulfonyl, azetidinylsulfonyl, imidazolidinylsulfonyl, pyrazolidinylsulfonyl, piberidinylsulfonyl, piperazinyl Partial or fully reduced saturation such as rusulfonyl, oxazolidinylsulfonyl, isoxazolidinylsulfonyl, thiazolidinylsulfonyl, vilazolidinylsulfonyl, dioxolanylsulfonyl or dioxanylsulfonyl groups A heterocyclic sulfonyl group, and the heterocyclic sulfonyl group may be condensed with another cyclic group such as a benzene ring, for example, benzothienylsulfonyl, benzothiazolylsulfonyl, benzo Oxazolylsulfonyl, isobenzo A lanylsulfonyl, quinolylsulfonyl, 1,3-benzodioxolanylsulfonyl, benzodioxanylindolylsulfonyl, isoindolylsulfonyl or indolinylsulfonyl group, preferably 1-pyrrolidinyl group; Rusulfonyl or 1-azetidinylsulfonyl group. In the above formula, the lower alkylsulfinyl group in the definition of the substituent group a indicates a group in which the lower alkyl group is bonded to a sulfiel group, such as methylsulfiel, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, Isobutylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, pentylsulfenyl, isopentylsulfinyl, 2-methylbutylsulfinyl, neopentylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, isohexylsulfinyl, 4-methylpentyl Sulfinyl, 3-methylpentylsulfinyl, 2-methylpentylsulfinyl, 1-methylpentylsulfinyl, 3,3-dimethylbutylsulfinyl, 2,2 Such as dimethylbutylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl or 2-ethylbutylsulfinyl; A C ₆ alkylsulfinyl group, preferably a C ₄ alkylsulfinyl group, more preferably a C 1, C ₂ alkylsulfinyl group, most preferably a methylsulfinyl group .

In the above formula, the arylsulfenyl group in the definition of the substituent group a indicates a group in which the aryl group is bonded to a sulfinyl group, and examples thereof include phenylsulfinyl, indenylsulfiel, naphthylsulfinyl, and phenanthrenyl. An aromatic hydrocarbon sulfinyl group having 6 to 14 carbon atoms such as a sulfinyl, anthracenylsulfinyl or fluorenylsulfinyl group, and preferably C ₆ —. An arylsulfinyl group, more preferably a phenylsulfenyl or naphthylsulfinyl group, and most preferably a phenylsulfinyl group.

In the above formula, the mono-lower alkyl group rubamoyl group in the definition of the substituent group a indicates a group in which one of the lower alkyl groups is bonded to the carbamoyl group, for example, methylcarbamoyl, edilcarbamoyl, propyl carbamoyl, Isopropyl carbamoyl, butyl carbamoyl, isobutyl carbamoyl, S-butyl carbamoyl, t- butylcarbamoyl, pentylcarbamoyl, isopentylcarbamoyl butylcarbamoyl, 2 - methyl Petit carbamoyl, neopentyl carbamoyl, a mono- one C ₆ alkyl force Rupamo I le groups such as 1 one Echirupuropiru force Rubamoiru or the alkoxy carbamoyl group, preferably Is a mono-C i-C ^ alkyl-powered rubamoyl group, more preferably a mono-C i- ^ alkyl-powered rubamoyl group, most preferably a methylcarbamoyl group.

In the above formula, the di-lower alkyl group rubamoyl group in the definition of the substituent group a represents a group in which two of the lower alkyl groups are bonded to a carpamoyl group, for example, dimethylcarbamoyl, getylcarbamoyl, N-ethyl N— methylcarbamoyl, dipropionate pills force Rubamoiru, dibutylcarbamoyl, Gee, such as carboxymethyl carbamoyl group to di pentylcarbamoyl or di (: an alkyl force Rubamoiru group, preferably a di one C ₄ alkyl force Rubamoiru group, further preferably Is a di-d-C ₂ alkylcarbamoyl group, most preferably a dimethylcarbamoyl group.

In the above formula, the lower alkyl (aryl) rubamoyl group in the definition of the substituent group a indicates a group in which the aryl group is bonded to the mono-lower alkyl rubamoyl group, for example, N-methyl N-phenylcarbamoyl, N-ethyl N-phenylcarbamoyl, N-phenyl N-propylcaproluvyl, N-isopropyl N-phenylcarbamoyl, N-butyl N-phenylcarbamoyl, N-pentyl N-phenylcarbamoyl, N —Hexyl N-phenylcarbamoyl group, N-methyl N-naphthyl carbamoyl, N-ethyl N-naphthylcarbamoyl, N-naphthyl N-propyl carbamoyl, N-isopropyl N-naphthylcarbamoyl, N-butyl N-naph Tylcarbamoyl, N-naphthyl N-pentylcarbamoyl, or N-hexyl N-naphthylka A Bamoiru group, preferably a N _ methyl N- phenylene Rukarubamoi Le group. In the above formula, the ethylidenehydrazinocarbonyl group in the definition of the substituent group a is, for example, [111- (phenyl) ethylidene] hydrazinocarbonyl, [111- (4-pyridyl) ethylidene] hydrazinocarbonyl or [1- (Methyl) ethylidene] hydrazinocarbonyl group, and preferably [1- (4-pyridyl) ethylidene] hydrazino carbonyl group.

In the above formula, the mono-lower alkyl group rubamoyloxy group in the definition of the substituent group a represents a group in which one of the above mono-lower alkylcarbamoyl groups is bonded to an oxygen atom, for example, methylcarbamoyloxy, ethylcarbamoyl Propyl, propyl carbamoyloxy, isopropyl rubamoyloxy, butylcarbamoyloxy, isobutylcarbamoyloxy, s-butylcarbamoyloxy, t-butylcarbamoyloxy, pentylcarbamoyloxy, isopentylcarbamoyloxy, 2-methylmethyl carbamoyl O carboxymethyl, neopentyl carbamoyl O carboxymethyl, model no C such as 1 over E Chirupuropiru force Rubamoiruokishi or the carboxymethyl-carbamoyl O alkoxy group, an C ₆ alkyl force Rubamoiruokishi group, preferably, mono- 〇 ₄ § A Ruki carbamoyl O alkoxy group, more preferably a mono - is one c ₂ alkyl Cal Bamoiruokishi group, most preferably a methylcarbamoyl O alkoxy group.

In the above formula, the di-lower alkyl rubamoyloxy group in the definition of the substituent group a represents a group in which one of the above di-lower alkyl rubamoyl groups is bonded to an oxygen atom, for example, dimethylcarbamoyloxy, A di-C ₆ alkyl radical rubamoyloxy group such as rucarbamoyloxy, N-ethyl N-methylcarbamoyloxy, dipropyl carbamoyloxy, dibutylcarbamoyloxy, dipentylcarbamoyloxy or dihexylcarbamoyloxy; Preferably, it is a di-C, 1 C ₄ alkyl radical rubamoyloxy group, more preferably, a di-C ₂ alkyl carbamoyloxy group, most preferably, a dimethylcarbamoyloxy group. In the above formula, the mono-lower alkyl rubamoylamino group in the definition of the substituent group a represents a group in which one mono-lower alkyl rubamoyl group is bonded to an amino group, for example, methylcarbamoylamino, ethylcarbamoylamino Mino, Propyl carbamoylamino, isopropylcarbamoylamino, butylcarbamoylamino, soptylcarbamoylamino, s-butylcarbamoylamino, t-butylcarbamoylamino

2-methyl-butylcarbamoyl § Mino, neopentyl carbamoyl § amino, -1-E No - alkyl force Rubamoiruamino group, preferably a mono- ten ₄ § Ruki carbamoyl § amino group, more preferably a mono - One C ₂ alkylcarbamoylamino group, most preferably a methylcarbamoylamino group.

In the above formula, the di-lower alkyl rubamoylamino group in the definition of the substituent group a represents a group in which one di-lower alkyl rubamoyl group is bonded to an amino group, for example, dimethylcarbamoylamino, carbamoyl § Mino, N- Echiru N- methylcarbamoyl § amino, dipropyl force Rubamoiruamino, di-heptyl carbamoylthiopheno such Gee C, - a C ₆ alkyl force Rubamoiruamino group, preferably a, - C, - C ₄ alkyl force Rubamoiruamino And more preferably a di-c ₂ alkylcarbamoylamino group, most preferably a dimethylcarbamoylamino group.

In the above formula, the lower alkylsulfonylamino group in the definition of the substituent group a indicates a group in which an amino group is bonded to the lower alkylsulfonyl group, for example, methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, Isopropyl sulfonylamino, butylsulfonylamino, isobutylsulfonylamino, S-butylsulfonylamino, t-butylsulfonylamino, pentylsulfonylamino, isopentylsulfonylamino, 2-methylbutylsulfonylamino, neobe 1-ethylpropylsulfonylamino, hexylsulfo Nilamino, isohexylsulfonylamino, 4-methylpentylsulfonylamino, 3-methylpentylsulfonylamino, 2-methylpentylsulfonylamino, 1-methylpentylsulfonylamino, 3,3-dimethylbutylsulfonylamino 1,2,2-dimethylbutylsulfonylamino, 1,1-dimethylbutylsulfonylamino, 1,2-dimethylbutylsulfonylamino, 1,3-dimethylbutylsulfonylamino, 2,3-dimethylbutylsulfonylamino, or 2 Echirubuchirusuru Honiruamino is an C ₆ alkylsulfonyl § amino groups such as, preferably a C _t one C ₄ alkylsulfonyl § amino group, and more preferably is an C ₂ Arukirusu Ruhoniruamino group, Most preferably, it is a methylsulfonylamino group.

In the above formula, the mono-lower alkylaminosulfonyl group in the definition of the substituent group a represents a group in which the mono-lower alkylamino group is bonded to a sulfonyl group, for example, methylaminosulfonyl, ethylaminosulfonyl, propylamino Sulfonyl, isopropylaminosulfonyl, butylaminosulfonyl, isobutylaminosulfonyl, s-butylaminosulfonyl, t-butylaminosulfonyl, pentylaminosulfonyl, isopentylaminosulfonyl, 2-methylbutylaminosulfonyl, neopentylaminosulfonyl, 11 Ethylpropylaminosulfonyl, hexylaminosulfonyl, isohexylaminosulfonyl,

3 _ methylpentylaminosulfonyl, 2-

3-dimethylbutylaminosulfonyl, 2,2-dimethylbutylaminosulfonyl, 1,1-dimethylbutylaminosulfonyl, 1,2-dimethylbutylaminosulfonyl, 1,3-dimethylbutylaminosulfonyl, 2,3- A mono-C ₆ alkylaminosulfonyl group such as a dimethylbutylaminosulfonyl or 2-ethylbutylaminosulfonyl group, preferably a mono-C ₄ alkylaminosulfonyl group, and more preferably a mono-C ₄ alkylaminosulfonyl group; C, - a C ₃ alkylamino scan Ruhoniru group, most preferably a methyl aminosulfonyl group. In the above formula, the di-lower alkylaminosulfonyl group in the definition of the substituent group a indicates a group in which the di-lower alkylamino group is bonded to a sulfonyl group, for example, dimethylaminosulfonyl, getylaminosulfonyl, N— Echiru N- Mechiruami Nosuruhoniru, dipropylamino sulfonyl, dibutyl aminosulfonyl, a di ten ₆ § Le kills aminosulfonyl groups such as cyclohexyl § amino sulfonyl group to Jipen chill aminosulfonyl or di, preferably, di C, A C ₄ alkylaminosulfonyl group, more preferably a di-C ₂ alkylaminosulfonyl group, and most preferably a dimethylaminosulfonyl group.

In the above formula, the mono-cycloalkylaminosulfonyl group in the definition of the substituent group a represents a group in which a monocycloalkylamino group is bonded to a sulfonyl group, for example, cyclopropylaminosulfonyl, cyclobutylaminosulfonyl, cyclopentylaminosulfonyl or cyclohexyl § amino mono- such as sulfonyl group C ₃ to consequent opening - (a 3 ₆ cycloalkyl aminosulfonyl group, preferably, mono- C ₃ - (a 3 ₄ cycloalkylamino sulfonyl Lulu group, most suitably Is a cyclopropylaminosulfonyl group.

In the above formula, the mono-lower alkoxy lower alkylaminosulfonyl group in the definition of the substituent group a indicates a group in which the lower alkoxy group is bonded to the mono-lower alkylaminosulfonyl group, for example, methoxymethylaminosulfonyl, Methoxyethylaminosulfonyl, methoxypropylaminosulfonyl, methoxybutylaminosulfonyl, methoxypentylaminosulfonyl, methoxyhexylaminosulfoxypropylaminosulfonyl, propoxymethylaminosulfonyl, propoxy shetylaminosulfonyl or propoxypropylaminosulfonyl group mono- C, such as one C ₆ alkoxy C _r - a C ₆ alkyl § amino sulfonyl group, preferably a mono - is an C ₃ alkoxy one c ₄ alkylaminosulfonyl group, most virtuous The, methoxymethyl aminosulfonyl or methoxy E chill aminosulfonyl group is there. '

In the above formula, the mono-lower alkoxycarbonyl lower alkylaminosulfonyl group in the definition of the substituent group a represents a group in which the lower alkoxycarbonyl group is bonded to the mono-lower alkylaminosulfonyl group. L-methylaminosulfonyl, methoxycarbonylethylaminosulfonyl, methoxycarbonylpropylaminosulfonyl, methoxycarbonylbutylaminosulfonyl, methoxycarbonylpentylaminosulfonyl, methoxycarboylhexylaminosulfonyl, ethoxycarbonylmethylaminosulfonyl , Ethoxycarbonylethylaminosulfonyl, ethoxycarbonylpropylaminosulfonyl, propoxycarbonylmethylaminosulfonyl, propoxycarbonylethylyl Mono-ci such as minosulfonyl or propoxycarbonylpropylaminosulfonyl groups

- C ₆ Arukokishikarupo sulfonyl (3, - a C ₆ alkyl § amino sulfonyl group, preferably, mono- C, one C ₃ alkoxy force Lupo sulfonyl (: is one C ₄ alkyl § amino sulfonyl group, Most preferably, it is a methoxycarbonylmethylaminosulfonyl or ethoxycarbonylmethylaminosulfonyl group.

In the above formula, the mono-l-rubamoyl lower alkylaminosulfonyl group in the definition of the substituent group a indicates a group in which a l-rubamoyl group is bonded to the mono-lower alkylaminosulfonyl group, for example, l-rubamoyl methylamino sulfonyl, force Rubamoirue chill aminosulfonyl, force Luba carbamoyloxy propyl aminosulfonyl, force Rubamoirubu chill aminosulfonyl, with a force Rubamoiru one c ₆ alkylaminosulfonyl groups such as forces Rubamoiru pen hexyl aminosulfonyl group to chill aminosulfonyl or force Rubamoiru And preferably, a carbamoyl (, —C ₄ alkylaminosulfonyl group, most preferably a carbamoylmethylaminosulfonyl group.

In the above formula, the mono-lower aliphatic acylaminosulfonyl in the definition of the substituent group a The group represents a group in which the above-mentioned mono-lower aliphatic acylamino group is bonded to a sulfonyl group. C2-C7 linear or branched lower fatty acids such as aminosulfonyl, pivaloylaminosulfonyl, hexanoylaminosulfonyl, acryloylaminosulfonyl, methacryloylaminosulfonyl or crotonylaminosulfonyl groups a family § sill aminosulfonyl group, preferably, mono- C ₂ - a C ₃ aliphatic § sill aminosulfonyl group, and most preferably, Ru § cetyl aminosulfonyl group der.

In the above formula, the hydroxy lower alkyl group in the definition of the substituent group a indicates a group in which one hydroxy group is substituted by the lower alkyl group, and examples thereof include hydroxymethyl, 2-hydroxyethyl, and 1-hydroxyethyl. A hydroxy (^ — (: ₆ alkyl group, such as tyl, 3-hydroxypropyl, 4-hydroxybutyl, 5-hydroxypentyl or 6-hydroxyhexyl group, and preferably a hydroxy-C ₄ alkyl group; More preferably, it is a hydroxy CC ₂ alkyl group, and most preferably, a hydroxymethyl group.

In the above formula, the aryloxy group in the definition of the substituent group a indicates a group in which the above aryl group is bonded to an oxygen atom, for example, phenyloxy, indenyloxy, naphthyloxy, phenanthrenyloxy, anthracenyloxy or fluorenyloxy. An aromatic hydrocarbon group having 6 to 14 carbon atoms such as a C ₆ -C 1 _Q group, preferably a C ₆ -C _1Q aryloxy group, more preferably a phenyloxy or naphthyloxy group; Preferably, it is a phenyloxy group.

In the above formula, 1 to ⁵ aryl groups independently substituted with any group selected from the substituent group a in the definition of RR ² , R ³ , R ⁴ , R ⁵ , RR ⁹ and R ^{1 ()} For specific examples of W

38 For example, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6 —Difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,3,4-trifluorophenyl, 2,3,6-trifluorophenyl, 2,4,5-trifluorophenyl, 3, 4,5-Trifluorophenyl, 2,3,5,6-tetrafluorophenyl, 2,3,5-Trichlorophenyl, 2,3,6-Trichloromethylphenyl, 2-, 3- or 4-methylphenyl, 2 1, 3- or 4-ethylphenyl, 4-isopropylphenyl,

4-isobutylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 3,5-dimethylphenyl, 2,3,4,5,6-pentenemethylphenyl, 2-,

3- or 4-trifluoromethylphenyl, 2-, 3- or 4-difluoromethyloxyphenyl, 2-, 3- or 4-trifluoromethyloxyphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 4-butoxyphenyl, 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxy Huenir, 3,

5-dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2-, 3- or 4-methylthiophene Enyl, 2-, 3- or 4-carboxyphenyl, 2-, 3- or 4-methoxycarbonyl phenyl, 2-, 3- or 4-ethoxycarbonylphenyl, 4-t-butoxycarbonyl phenyl , 2-, 3- or 4-cetylaminophenyl, 2-, 3- or 4-methylsulfonylphenyl, 2-, 3- or 4-ethylsulfonylphenyl, 2-, 3- or 4- Aminosulfonylphenyl, 21,3- or 4-methylaminosulfonylphenyl, 2-, 3- or 4-ethylaminosulfonylphenyl, 2-, 3- or 4-propylaminosulfonylphenyl , 2-, 3- or 4-cyclopropylaminosulfonylphenyl, 2-, 3- or 4-dimethylaminosulfonylphenyl, 2-, 3_ or 4-hydroxyphenyl, 3,5-dihydroxyphenyl, 2 1,3- or 4-aminophenyl, 2-, 3- or 4-dimethylaminophenyl, 2-, 3- or 412-trophenyl, 2-, 3- or 4-cyano Phenyl, 2-fluoro-5-chlorophenyl, 2-fluoro-4-methylphenyl, 2-fluoro-5-methylphenyl, 2-fluoro-3-trifluoromethylphenyl, 2-fluoro-4-trifluoromethylphenyl 2-fluoro-5-trifluoromethylphenyl, 2-fluoro-6-trifluoromethylphenyl, 2-fluoro-4-methoxyphenyl, 2-fluoro-3-ethoxyphenyl, 2-fluoro-5-nitrophenyl, 3 —Fluoro-2-methylphenyl, 3-fluoro 4-methylphenyl, 3-fluoro-5-trifluoromethylphenyl, 4-fluoro-2-trifluoromethylphenyl, 4-fluoro-3-trifluoromethylphenyl, 4-fluoro-3 —Methoxyphenyl, 2-chloro-4-Fluoro mouth phenyl, 2-chloro 1-fluorophenyl, 2-chloro-5-trifluoromethylphenyl, 2-chloro-4-hydroxyphenyl, 2-chloro-5-nitrophenyl, 3-chloro-6-nitrophenyl, 4-chloro-2-fluorophenyl, 4-chlorophenyl 3-fluorophenyl, 4-chloro-3-nitrophenyl, 4-chloro 6-nitrophenyl, 3,5-dichloro-2-hydroxyphenyl, 3-t-butyl-2-hydroxyphenyl, 3-t-butyl _ 6-hydroxyphenyl, 3-trifluoromethyloxy 6-hydroxyphenyl, 2-methoxy-5-methylphenyl, 2-methoxy-5-t-butylphenyl, 2-methoxy-5-phenylphenyl, 4-methoxy-1,2,3-dimethylphenyl, 4-methoxy-2,5-dimethylphenyl, 3-ethoxy-4-methoxy Phenyl, 4-ethoxy-3-methoxyphenyl, 2,4-dimethoxy-3-methylphenyl, 3,4-dimethoxy-6-ditrophenyl, 2-hydroxy-5-methylphenyl, 2-hydroxy-4-methoxyphenyl, 2-hydroxy-1 5-methoxyphenyl, 2-hydroxy-3-ethoxyphenyl, 2-hydroxy-4-ethylpyraminophenyl, 2-hydroxy-5-ethylpyraminophenyl, 2-hydroxy-5-1-2trophenyl, 2 —Hydroxy-3-methoxy-5-ditrophenyl, 3-hydroxy-14-nitrophenyl, 3-hydroxy-16-ditrophenyl, 4-hydroxy-3-methoxy-5-ditrophenyl, 4-hydroxy-13,5 -Dimethylaminophenyl, 4-hydroxy-3-methylphenyl, 4-hydroxy-2-methoxyphenyl , 4-hydroxy-3-Metokishifue sulfonyl, 4-hydroxy one 3-nitrophenyl, 4 —Hydroxy-1,3,5-dimethylphenyl, 3-hydroxy-4,5-dimethoxyphenyl, 4-hydroxy-1,3,5-dimethoxyphenyl, 3-hydroxypropyl-4-hydroxyphenyl, 5-carboxy-6-hydroxyphenyl They are enyl, 2-ethoxy-naphthalene-11-yl, 4-methoxynaphthalene-111-yl, and 4-dimethylaminononaphthalene-1-yl.

In RR ³ and R ⁹ , preferably a phenyl group independently substituted with 1 to 3 arbitrary groups selected from the substituent group a, more preferably 1 to 3 substituents (The substituent is a group selected from the group consisting of a lower alkyl group, a halogen atom, a lower alkoxy group, a halogeno lower alkyl group, and a hydroxy group.) A phenyl group substituted with one to three substituents (the substituent is a group selected from the group consisting of a lower alkyl group and an octogen atom).

In R ² , R ⁴ and R ^{1 ()} , preferably C ₆ —C [independently substituted with 1 to 5 arbitrary groups selected from the substituent group a. Aryl group, more preferably a phenyl or naphthyl group independently substituted with 1 to 5 arbitrary groups selected from the substituent group a, more preferably 1 to 3 substituted A phenyl or naphthyl group substituted with a group (the substituent is a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group, a nitro group, a cyano group, a carboxy group, a lower alkoxycarbonyl group, an aliphatic acylamino group, Halobamoyl, lower alkylsulfonyl, hydroxy lower alkyl, lower alkylsulfonylamino, aminosulfonyl, mono-lower alkylaminosulfonyl, mono-cycloalkylaminosulfonyl, di-lower alkylaminosulfonyl, arylyl And oxo groups.) And, more preferably, a phenyl or naphthyl group substituted with 1 to 3 substituents (the substituent is a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group, a nitro group, a cyano group) , Lower alkoxycarbonyl, aliphatic acylamino, lower alkylsulfonyl, aminosulfonyl, mono It is a group selected from the group consisting of a lower alkylaminosulfonyl group, a mono-cycloalkylaminosulfonyl group and a di-lower alkylaminosulfonyl group. ) Der is, more preferably, substituted by 1 to 3 substituents, phenyl or naphthyl group (the substituent is a fluorine atom, a chlorine atom, C, - C ₂ alkyl groups, C [- C ₂ alkoxy group, hydroxy group, nitro group, Shiano group, (! C one C ₂ alkoxy) carboxamide sulfonyl group, c ₂ - c ₃ aliphatic Ashiruamino group, c, - c ₂ alkylsulfonyl group, Aminosuruhoni group, one A C ₃ alkylaminosulfonyl group, a C ₃ —C ₄ cycloalkylaminosulfonyl group and a di-C 1, 1 C ₂ alkylaminosulfonyl group.) Preferably, 2,3,6-trifluorophenyl, 4-methylsulfonylphenyl, 4-ethylsulfonylphenyl, 2,6-difluoromouth phenyl, 2,3-dimethoxyphenyl, 2,5-dimethoxy Phenyl, 2—, 3 —Or 4-cyanophenyl, 3,4-dimethoxy-1-6-ditrophenyl, 4-methoxycarbonylphenyl, 4-ethoxycarbonylphenyl, 4-acetylmethylaminophenyl, 2-chloro-5-ditrophenyl, 3-hydroxy-6-2 Torophenyl, 4-aminosulfonylphenyl, 4-methylaminosulfonylphenyl, 4-ethylaminosulfonylphenyl, 4-propylaminosulfonylphenyl, 4-cyclopropylaminosulfonylphenyl or 4-dimethylaminosulfonyl A diphenyl group, most preferably, 4-cyanophenyl, 4-methylsulfonylphenyl, 4-ethylsulfonylphenyl, 4-acetylaminophenyl, 3,4-dimethoxy-6-ditrophenyl, 4-aminosulfonyl Phenyl, 4-methylaminosulfonyl Enyl, 4 E chill aminosulfonyl phenylalanine, 4 one propylamino sulfonyl phenylalanine, 4-cyclopropyl-aminosulfonyl-phenylalanine or 4 one dimethyl § amino sulfonyl phenyl group.

In R ⁵ and R ⁸ , preferably C ₆ — independently substituted with 1 to 5 arbitrary groups selected from the substituent group a. And more preferably C ₆ —C, which is independently substituted with 1 to 3 arbitrary groups selected from the substituent group a. Aryl group, more preferably, a phenyl group substituted with 1 to 3 substituents (the substituent is Selected from a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkoxycarbonyl group, a mono lower alkylamino group, a G lower alkylamino group, a nitro group, a cyano group and an aryl group. Group. And more preferably, a phenyl group substituted with 1 to 3 substituents (the substituents may be a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, And more preferably a phenyl group substituted with 1 to 3 substituents (the substituent is a fluorine atom, a chlorine atom, a C,-^ alkyl group). , halogeno ten ₂ § alkyl group, C, -C ₂ alkoxy, C, -C ₂ alkylthio group, and a C ₆ -. a C _1Q Ari group selected from Le group), more preferably, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluoro Phenyl, 3, 4-difluorophenyl 3,5-difluorophenyl, 2,3,4-trifluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-methylphenyl, 4-methylphenyl, 2,4 -Dimethylphenyl, 2-, 3_ or 4-methoxyphenyl, 2-ethoxyphenyl, 2-methylthiophenyl, 3,5-dimethoxyphenyl, 2-fluoro-4-chlorophenyl, 2_ Fluoro-5-chlorophenyl, 2-fluoro-4-methylphenyl, 2-fluoro-5-methylphenyl, 2-fluoro-5-trifluoromethylphenyl, 2-methoxy-5-methylphenyl, 2-methoxy-5-t-butylphenyl , 2-fluoro-4-methoxyphenyl, 4-fluoro-3-methoxyphenyl or 2-methoxy-15-phenylphenyl, most preferably 2 —Fluorophenyl or 2-methoxyphenyl group. In the above formula, specific examples of the heterocyclic group independently substituted with 1 to 3 arbitrary groups selected from the substituent group a in the definition of R ² , R ⁴ , RK R ⁸ and R ^1D include, for example, 3-, 4- or 5-fluorothiophene-2-yl, 3-, 4- or 5-chlorothiophene-2-yl, 3-, 4- or 5-methylthiophene-2-yl , 3-, 4- or 5-ethylthiophen-2-yl, 3-, 4- or 5-nitrothiophen-2-yl, 3-, 4- or 5-carboxythiophen-2-yl 3-, 1- or 5-methylfuran-2-yl, 3-, 4- or 5-ethylfuran-2-yl, 3-, 4- or 5-hydroxymethylfuran-21-yl, 3-, 4- or 5-carboxyfuran-2-yl, 4,5-dimethylfuran-2-yl, 1-methyl-pyrrole-12-yl, 2,4-dimethyl-2,3 —Thiazoyl 5-yl, 8-hydroxyquinoline 2-yl, 2-chloroquinoline-3-yl, 1-methylindole 2-yl, 1-acetylamino-indole-21-yl, 2-Methylindole 3-yl, 1-acetyl-yl 3-yl, 5-Methoxyindole 3-yl, 1 -Methylimidazo-Lu-2-yl, 5-Methylimidazole-41-yl, 3,5-Dimethyl-111-Fenrubirazol-4-1-yl, 2,2-Difluoro-1,3-benzodioxo-lan-5-yl , 5-chloro-1,3-benzobenzoxolane 6-yl, 6-chloro-1,3-benzobenzoxolane 7-yl, 5-twotro 1,3-benzobenzoxolane-6-yl Or 6-Nitro 1, 3.—Benzodioxolan— 7-yl.

In R ² , R ⁴ and R ^1Q , preferably a 5- to 6-membered heterocyclic ring which may be condensed with a benzene ring, which is independently substituted with 1 to 3 arbitrary groups selected from substituent group a More preferably, furyl, phenyl, pyrrolyl, pyrazolyl, imidazolyl, which is independently substituted with 1 to 3 arbitrary groups selected from the substituent group a and may be condensed with a benzene ring, Thienyl which is a thiazolyl, a pyranyl, a pyridyl, a 1,3-dioxolanyl or a 1,3-dioxanyl group, more preferably 1 to 3 independently substituted by any group selected from the substituent group a. Thiazolyl, pyridyl, quinolyl or a 1,3-benzodioxolanyl group, and even more preferably, phenyl, thiazolyl, pyridyl, quinolyl or 1, substituted with 1 to 3 substituents. 3-benzodioxolar group (The substituent is a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group, a nitro group, a cyano group, a hydroxyl group, a lower alkoxycarbonyl group, an aliphatic acylamino group. Group, Lubamoyl group, It is a group selected from the group consisting of a lower alkylsulfonyl group, a hydroxy lower alkyl group, a lower alkylsulfonylamino group, an aryl group and an oxo group. More preferably, a phenyl, thiazolyl, pyridyl, quinolyl or 1,3-benzodioxolanyl group substituted with 1 to 3 substituents (the substituent is a halogen atom, A lower alkyl group, a lower alkoxy group, a hydroxy group, a nitro group, a cyano group, a lower alkoxycarbonyl group, an aliphatic acylamino group, and a lower alkylsulfonyl group.) the substituted with 1 to 3 substituents, thienyl, thiazolyl, pyridyl, 1 quinolyl young properly, 3-benzo-di O key Sora sulfonyl group (the substituent is a fluorine atom, a chlorine atom, CC ₂ alkyl group, C, - C ₂ alkoxy group, hydroxy group, nitro group, Shiano group, (! C -cZ alkoxy) Karuponiru group, c ₂ - c ₃ aliphatic Ashiruamino group and one c ₂ A group selected from the group consisting of alkenylsulfonyl groups.) And most preferably. 2-Chloroquinolin-1-yl, 5-nitro-1,3-benzobenzoxorane-6- 7-yl, 6-nitro-1,3-benzodioxolan, 7-yl, 5-chloro-1,3-benzodioxolan-6-yl, 6-chloro-1,3-benzodioxolan-1 or 2,4-Dimethyl-1,3-thiazol-5-yl group.

In R ⁵ and R ⁸ , it is preferably a 5- to 6-membered heterocyclic group which may be independently condensed with a benzene ring, which is independently substituted with 1 to 3 arbitrary groups selected from the substituent group a. More preferably, it is a 5- to 6-membered aromatic heterocyclic group independently substituted with 1 to 3 arbitrary groups selected from the substituent group a, more preferably selected from the substituent group a. A pyridyl or phenyl group, which is independently substituted with 1 to 3 substituents, and even more preferably a pyridyl or phenyl group, which is substituted with 1 to 3 substituents. The groups include a halogen atom, a lower alkyl group, an octogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkoxycarbonyl group, a mono-lower alkylamino group, a di-lower alkylamino group, a nitro group, a cyano group and the like. From reel reel It is a group-option.), And the most preferred, which is substituted by 1 to 3 substituents, pyridyl or thienyl group (the substituent is a halogen atom, lower W

It is a group selected from a 45-alkyl group, a halogeno-lower alkyl group, a lower-alkoxy group, a lower-alkylthio group and an aryl group. ). In the above formula, R ² is together with R ¹ , R ⁴ is together with R ³ and Z or R ^{1 ()} is together with R ⁹ , each comprising a carbon atom to which they are attached. Specific examples of the saturated carbocyclic group substituted by 1 to 5 groups selected from the group a include, for example, 3,5-tetramethylcyclohexane-111-pyridene, 3-, 5- or 6- Fluoro-2,3-dihydroindene-1-ylidene, 3-, 5- or 6-chloro-2,3-dihydroindene-1-ylidene, 3-, 5- or 6-methoxy-2,3-dihydroindene-11 Ilidene, 3-, 5- or 6-acetylamino-2,3-dihydroindene-1-ylidene, 3-, 5- or 6-nitro-12,3-dihydroindene-1-ylidene or 5,6-dimethoxy-2 , 3-dihydric indene 1-ylidene group; A C ₄ -C ₇ saturated carbocyclic group which is independently substituted with 1 to 5 arbitrary groups selected from the substituent group a and may be condensed with a benzene ring, more preferably a substituent group a C ₅ -C ₆ saturated carbocyclic group which may be condensed with a benzene ring, which is independently substituted with 1 to 5 arbitrary groups selected from a, and more preferably 1 to 3 substituted Substituted with an indane or a 1,2,3,4-tetrahydronaphthalene group (the substituent is an octylogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a lower alkoxycarbonyl group, a lower aliphatic acylamino) A lower alkylsulfonyl group, a cyano group and an aralkyl group.), And even more preferably, indane or 1, 2, or 3, 4-tetrahydronaphthalene (The substituent is a group selected from the group consisting of a lower alkoxy group, a lower aliphatic acylamino group, a lower alkylsulfonyl group and a cyano group), and most preferably a lower alkoxy group. And 3 to 3 substituted indane or 1,2,3,4-tetrahydronaphthalene groups. In the above formula, R ² is formed together with R ¹ , R ⁴ is formed together with R ³ and R or R ^{1 ()} is formed together with R ′ ⁹ , each including the carbon atom to which they are bonded. Selected from substituent group a Specific examples of the saturated heterocyclic group which is independently substituted with 1 to 3 arbitrary groups include, for example, 1-t-butoxycarbonylpyridine-141-ylidene or 1-benzylpyridine-141-ylidene group And is preferably a 5- to 6-membered saturated heterocyclic group independently substituted with 1 to 3 arbitrary groups selected from the substituent group a, and more preferably a substituent group a A tetrahydrothiophene ring, a tetrahydropyran ring or a piperidine ring group independently substituted by 1 to 3 substituents with an arbitrary group selected, more preferably a tetrahydrothiophene ring substituted by 1 to 3 substituents A phen ring, a tetrahydric pyran ring or a piperidine ring group (the substituent is a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a lower alkoxycarbonyl group, a lower aliphatic acylamino group, A group selected from the group consisting of an alkylsulfonyl group, a cyano group and an aralkyl group.), And most preferably a tetrahydrothiophene ring, a tetrahydropyran ring or a tetrahydropyran ring substituted by one to three substituents. And a piperidine ring group (the substituent is a group selected from the group consisting of a lower alkoxy group, a lower aliphatic acylamino group, a lower alkylsulfonyl group and a cyano group). The pharmacologically acceptable salt is a pyrimidine derivative having the general formula (I) or (II) of the present invention, which has a basic group such as an amino group, when reacted with an acid. When the compound has an acidic group such as a carboxy group, it can be converted into a salt by reacting with a base.

As the salt based on a basic group, preferably, hydrofluoride, hydrochloride, hydrobromide, hydrooctylogenate such as hydroiodide, nitrate, perchlorate, Inorganic acid salts such as sulfates and phosphates; lower alkanesulfonates such as methanesulfonate, trifluoromethanesulfonate and ethanesulfonate, benzenesulfonates and salts such as p-toluenesulfonate Organic acid salts such as reel sulfonate, acetate, malate, fumarate, succinate, citrate, ascorbate, tartrate, oxalate, maleate; and glycine salt, lysine And salts of amino acids such as salts, arginine salts, orditin salts, glutamate salts, and aspartate salts, most preferably hydrohalide salts, inorganic acid salts or organic acid salts. . On the other hand, the salt based on an acidic group is preferably a sodium salt, a potassium salt, or a sodium salt. Alkali metal salts such as lithium salts, alkaline earth metal salts such as calcium salts and magnesium salts, metal salts such as aluminum salts and iron salts; inorganic salts such as ammonium salts; octylamine salts, dibenzylamine salts Salts, morpholine salts, darcosamine salts, phenylglycine alkyl ester salts, ethylenediamine salts, N-methyl dalkamine salts, guanidine salts, getylamine salts, triethylamine salts, dicyclohexylamine salts, N, N, dibenzylethylenediamine Organic salts such as mine salt, black mouth pro-force salt, pro-force salt, diethanolamine salt, N-benzylphenethylamine salt, piperazine salt, tetramethylammonium salt, tris (hydroxymethyl) amino methane salt Amine salts such as salts; and glycine salts, lysine salts, Ginin salts, Ol two Chin, glutamate, there may be mentioned Amino acid salts such as Asuparagin acid salt, most preferably a alkali metal salt. The pyrimidine derivative having the general formula (I) or (II), its pharmaceutically acceptable salt, its ester or its pond derivative of the present invention has various asymmetric carbon atoms in its molecule. Isomers. In the compounds of the present invention, these isomers and mixtures of these isomers are all represented by a single formula, that is, by the general formula (I) or (II). Accordingly, the present invention includes all such isomers and mixtures of these isomers in any proportion. In particular, the pyrimidine derivative having the general formula '(I) or' (II), its pharmaceutically acceptable salt, its ester or other derivatives of the present invention has a double bond in its molecule. Having geometric isomers. In the compounds of the present invention, all the geometric isomers and mixtures of geometric isomers are represented by a single formula, that is, the general formula (I) or (II) ′. Accordingly, the present invention includes all geometric isomers and mixtures of geometric isomers in any proportion. The pyrimidine derivative having the general formula (I) or (II) of the present invention, its pharmaceutically acceptable salt, its ester or other derivative can be obtained by leaving it in the air or by recrystallization. , Absorbs water, becomes wet with water and hydrates In some cases, such hydrates are also included in the salts of the present invention. The ester in the above refers to the ester of the compound (I) or (II) of the present invention because it can be converted to an ester. Examples of such an ester include an ester of a hydroxy group. Refers to an ester whose ester residue is a general protecting group or a protecting group that can be cleaved in vivo by a biological method such as hydrolysis. A general protecting group is a protecting group that can be cleaved by a chemical method such as hydrogenolysis, hydrolysis, electrolysis, or photolysis.

Preferred general protecting groups for the ester of a hydroxy group include formyl, acetyl, propionyl, butyryl, isoptyryl, pentanoyl, pivaloyl, valeryl, isovaleryl, octanoyl, nonanoyl, decanol, 3-methylnonanoyl, and 8-methylnonanol. , 3-Echiloktanoyl, 3,7-Dimethyloktanoyl, Pendekanoyl, Dodecanoyl, Tridecanoyl, Tetradecanoyl, Pentadecanoyl, Hexadecanyl, 1-Methylpendecanyl, Tadecanoyl, Dekanoyl, 15-methyl 1 Alkanoyl groups such as methyl-heptadecanoyl, nonadecanoyl, eicosanoyl, henicosanoyl, chloroacetyl, dichloroacetyl, trichloroacetyl, trichloroacetyl Halogenated alkylcarbonyl groups such as fluoroacetyl, alkoxyalkylcarbonyl groups such as methoxyacetyl, acryloyl, propioloyl, methacryloyl, crotonyl, isocrotonyl, and unsaturated alkyl groups such as (E) 1-2-methyl-2-butenoyl And lower-substituted aliphatic acyl groups such as a group (preferably a lower aliphatic acyl group having 2 to 6 carbon atoms); aryl carboxyl groups such as benzoyl, α-naphthoyl and j3-naphthoyl 1,2-bromobenzyl, 4-alkylbenzoyl groups such as mono-benzoyl, 2,4,6-trimethylbenzoyl, lower alkylyl-carbonyl groups such as 4-toluoyl, 4-anisole Lower alkoxylated arylcarbonyl Group, 4-nitrobenzoyl, nitrated aryl groups such as 2-nitrobenzoyl, roponyl group, lower alkoxy groups, such as 2- (methoxycarbonyl) benzoyl, phenylated arylcarbonyl group, 4-phenylene Aryl groups such as rubenzyl Substituted aromatic acyl groups such as aryl carbonyl group; lower alkoxy groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, S-butoxycarbonyl, t-butoxycarbonyl, and isobutoxycarbonyl. Alkoxyl-lponyl groups such as lower alkoxyl-lponyl groups substituted with halogens or tri-l-lower alkylsilyl groups such as carbonyl groups, 2,2,2-trichloromouth ethoxycarbonyl and 2-trimethylsilylethoxycarbonyl; tetrahydropyran One two one Or tetrahydropyranyl such as 3-bromotetrahydropyran-1-yl, 4-methoxytetrahydropyran-4-yl, tetrahydrothiopyran-12-yl, 4-methoxytetrahydrothiopyran-14-yl or Tetrahydrothiopyranyl group; tetrahydrofuranyl or tetrahydrothiofuranyl group such as tetrahydrofuran-1-yl and tetrahydrothiofuran-12-yl; trimethylsilyl, triethylsilyl, isopropyldimethylsilyl, t-butyldimethylsilyl, methyldiisopropyl Tri-lower alkylsilyl groups such as silyl, methyldi-butylsilyl, triisopropylsilyl, diphenylmethylsilyl, diphenylbutylsilyl, diphenylisopropylsilyl, and phenyldiisopropylsilyl Silyl groups such as tri-lower alkylsilyl groups substituted by one or two aryl groups; methoxymethyl, 1,1-dimethyl-1-methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, butoxy Lower alkoxymethyl groups such as methyl and t-butoxymethyl; alkoxymethyl groups such as halogeno lower alkoxymethyl such as 2,2,2-trichloroethoxymethyl and bis (2-chloroethoxy) methyl; 1 One et

Substituted ethyl groups such as halogenated ethyl groups such as 2,2,2-trichloromethyl; benzyl, hynaphthylmethyl, β-naphthylylmethyl, diphenylmethyl, triphenylmethyl, naphthyldiphenylmethyl, 9-anthrylmethyl As Lower alkyl groups substituted with 1 to 3 aryl groups, 4-methylbenzyl, 2,4,6-trimethylbenzyl, 3,4,5-trimethylbenzyl, 4-methoxybenzyl, 4-methoxyphenyldiph Aryl ring substituted with lower alkyl, lower alkoxy, nitro, halogen, cyano groups such as enylmethyl, 2-nitrobenzyl, 4-nitrobenzyl, 4-chlorobenzyl, 4-bromobenzyl, 4-cyanobenzyl An aralkyl group such as a lower alkyl group substituted with 1 to 3 aryl groups; an alkenyloxylponyl group such as bieroxyloxycarbonyl, aryloxycarbonyl; benzyloxycarbonyl, 4-methoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, 2-dibenzyloxycarbonyl 4 An arylalkyloxycarbonyl group in which the aryl ring may be substituted with one or two lower alkoxy or nitro groups, such as 12-trobenzylsiloxycarbonyl, is preferably substituted. It is a lower aliphatic acyl group, an aralkyl group or a silyl group.

 The general protecting group for the ester of a carboxy group is preferably the lower alkyl group described above: ethenyl, 1-propenyl, 2-propenyl, 1-methyl-2-propenyl, 1-methyl-1 1-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 2-ethyl-2-propenyl, 1-butenyl, 2-butenyl, 1-methyl-2-butenyl, 1-methyl — 1-butenyl, 3-methyl-2-butenyl, 1-ethyl-2-butenyl, 3-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 1-ethyl-3-butenyl, 1-pentenyl,

2-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,

3-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,

Lower alkenyl groups such as 4-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-1-pentenyl 1-hexenyl, 2-hexenyl, 3_hexenyl, 4-hexenyl, 5-hexenyl; Ethynyl, 2-propiel, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-ethyl-2-propynyl, 2-butenyl, 1-methyl-1-butynyl, 2-methyl-1-butynyl, 1-ethyl -2-butynyl, 3-butenyl, 1-methyl-1-butynyl, 2-methyl-3-butynyl, 1-ethyl-3-butynyl, 2-pentynyl, 1-methyl-2-pen W

51 Thynyl, 2-methyl-2-pentynyl, 3-pentynyl, 1-methyl-3-pentynyl, 2-methyl_3-pentynyl, 4-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 2- Lower alkynyl groups such as hexynyl, 3-hexynyl, 4-hexyl, and 5-hexynyl; the above-mentioned halogeno lower alkyl; 2-hydroxyethyl, 2,3-dihydroxypropyl, 3-hydroxypropyl, 3, A hydroxy lower alkyl group such as 4-dihydroxybutyl and 4-hydroxybutyl; a lower aliphatic acyl-lower alkyl group such as acetylmethyl; the aralkyl group; the silyl group, preferably a lower alkyl group or an aralkyl group; Group. A protective group that can be cleaved in vivo by a biological method such as hydrolysis is a protective group that is cleaved in a human body by a biological method such as hydrolysis to generate a free acid or a salt thereof. To determine whether a derivative is such, administer it to a test animal such as a rat or mouse by intravenous injection and then examine the body fluid of the animal to detect the original compound or its pharmacologically acceptable salt. Can be determined by what you can do,

As the protecting group which can be cleaved by a biological method such as hydrolysis in the living body to the ester of the hydroxy group, preferably, formyloxymethyl, acetooxymethyl, dimethylaminoacetoxymethyl, propionyloxymethyl , Butyryloxymethyl, Pivaloyloxymethyl, Valeryloxymethyl, Isoparelliroxymethyl, Hexanoyloxymethyl, 1-Formyloxyxetil, 1-Acetoxyxetil, 1-Propionyloxyxetil, 1-Ptyrilyl 1-pivaloyloxetil, 1-valeryloxetil, 1-isovaleryloxetil, 1-hexanolyloxetil, 1-formyloxypropyl, 1-acetoxy Propyl, 1-propionyloxypropyl, 1-butyryloxypropyl, 1-pi Lyloxypropyl, 1-valeryloxypropyl, 1-isovaleryloxypropyl, 1-hexanoyloxypropyl, 1-acetoxybutyl, 1-propionyloxybutyl, 1-butyryloxybutyl, 1- Pivaloyloxybutyl, 1-acetoxypentyl, 1-propionyloxypentyl, 1-butyryloxypentyl, 1-pivaloyloxypentyl, 1-piva 1- (lower aliphatic acyloxy) lower alkyl groups such as loyloxyhexyl, cyclopentylcarpoxyloxymethyl, cyclohexylcarpoxyloxymethyl, 1-cyclopentylcarpoxyloxyshetyl, 1-cyclohexylcarpoxyloxyshetyl, 1 1- (cycloalkylcarbonyloxy) lower alkyl groups, such as 1-cyclopentylcarbonyloxypropyl, 1-cyclohexylcarbonyloxypropyl, 1-cyclopentylcarbonyloxybutyl, and 1-cyclohexylcarbonyloxybutyl, benzoylo 11- (Acryloxy) lower alkyl groups such as 11- (aromatic acyloxy) lower alkyl groups such as xymethyl; methoxycarponyloxymethyl, ethoxycarponyloxymethyl, propoxyl Xymethyl, isopropoxyloxyloxymethyl, butoxycarpoxyloxymethyl, isobutoxycarpoxyloxymethyl, pentyloxyloxyloxyloxymethyl, hexyloxyloxyloxyloxymethyl, cyclohexyloxyloxyloxymethyl, Cyclohexyloxycarpoxyloxy (cyclohexyl) methyl, 1- (methoxycarpoxyloxy) ethyl, 1- (ethoxycarpoxyloxy) ethyl, 1- (propoxyloxylponoxyl) ethyl, 1- (iso Ethyl, 1- (Butoxycarponyloxy) ethyl, 1- (Isobutoxycarponyloxy) ethyl, 1- (t_Butoxycarponyloxy) ethyl, 11- (Pentyloxycarponyloxy) ethyl Ethyl, 11 Oxycarbonyloxy) ethyl, 1- (cyclopentyloxycarbonyloxy) ethyl, 1- (cyclopentyloxycarponyloxy) propyl, 1- (cyclohexyloxy-propylonyloxy) propyl, 1- (cyclopentyloxy) propyl (Xycarbonyloxy) butyl, 1- (cyclohexyloxy) butyl, 1- (cyclohexyloxycarbonyl) ethyl, 1- (ethoxycarbonyloxy) propyl, 1- (methoxycarbonyl) Xy) propyl, 1- (ethoxycarbonyloxy) propyl, 1- (propoxycarponyloxy) propyl, 1- (isopropoxyl-ponyloxy) propyl, 1- (butoxycarponyloxy) propyl, 1- (iso Butoxycarbonyloxy) propyl, 1 1- (Pentyloxycarponyloxy) propyl, 1- (Hexyloxy-capillonyloxy) propyl Xy) butyl, 1- (ethoxycarponyloxy) butyl, 1- (propoxyl-ponyloxy) butyl, 1- (isopropoxy-lponyloxy) butyl, 1- (butoxycarponyloxy) butyl, 1- (isobutoxycarponylo) Xyl) Like butyl, 1- (methoxycarponyloxy) pentyl, 1- (ethoxycarboxy) pentyl, 1- (methoxycarbonyloxy) hexyl, 1- (ethoxycarponyloxy) hexyl (Lower alkoxycarbonyloxy) alkyl group; (5-phenyl-2-oxo-1,3-dioxolen-4-yl) methyl, [5- (4-methylphenyl) 1-2-oxo-1,3 —Dioxolen-41-yl] Methyl, [5- (4-Methoxyphenyl) -121-oxo _1,3-Dioxolen-4-1-yl] Tyl, [5- (4-fluorophenyl) -l-oxo-l, 3-dioxolene-l-yl] methyl, [5- (4-chlorophenyl) -l-l-oxo-l, 3-dioxolene 4'-yl) methyl, (2-oxo-1,3-dioxolen-1-4-yl) methyl, (5-methyl-2-oxo-1 1,3-dioxolen-1 4-^^) methyl, (5-Ethyl-2-oxo-1,3-dioxolen-41-yl) Methyl, (5-Propyl-2-oxo-1,3-dioxolen-4-1-yl) methyl, (5-isopropyl-1-2-oxo) Lower calponyloxy groups such as oxodioxorenylmethyl groups such as 1,3-dioxolen-4-yl) methyl and (5-butyl-2-oxo-1,3-dioxolen-4-yl) methyl; Alkyl group; furidyl, dimethylphthalidyl, dimethoxyphthalidyl A lower aliphatic acyl group; the aromatic acyl group; a residue of a succinic acid salt of a salt of a phosphate; a residue of a phosphoric acid ester salt: an ester-forming residue of an amino acid or the like; a carbamoyl group; A carbamoyl group substituted with a lower alkyl group; and a (acyloxy) alkyloxycarbonyl group such as pivaloyloxymethyloxycarbonyl.

On the other hand, as the protecting group which can be cleaved by a biological method such as hydrolysis in a living body, an ester of a carboxy group is preferably methoxyethyl, 1-ethoxyethyl, 1-methyl-1-methoxyethyl, or 1-methoxyethyl. (Isopropoxy) ethyl, 2-methoxyethyl, 2-ethoxyl, 1,1-dimethyl-1-methyl'toxethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, n-buty Lower alkoxy lower alkyl groups such as xymethyl, t-butoxymethyl, 2-alkyl groups, aryloxy lower alkyl groups such as phenoxymethyl, 2,2,2-trichloroethoxymethyl, bis (2-chloroethoxy) Alkoxyalkyl groups such as halogenated lower alkoxy lower alkyl groups such as methyl; lower alkoxycarbonyl lower alkyl groups such as methoxycarbonylmethyl; cyano lower alkyl groups such as cyanomethyl and 2-cyanoethyl; methylthiomethyl and ethylthiomethyl Lower alkylthiomethyl group; arylthiomethyl group such as phenylthiomethyl and naphthylthiomethyl; lower alkylsulfonyl which may be substituted with halogen such as 2-methanesulfonylether and 2-trifluoromethanesulfonylethyl Lower alkyl groups; arylsulfonyl lower alkyl groups such as 2-benzenesulfonylethyl and 2-toluenesulfonylethyl; the above-mentioned (acyloxy) lower alkyl groups; the above-mentioned phenylidyl groups; and the above-mentioned aryl groups The lower alkyl groups; carboxyalkyl groups such as carboxymethyl; and amide-forming residues of amino acids such as phenylalanine. When the compound (I) or (II) of the present invention has an amino group, the other derivative may be a derivative other than the above-mentioned pharmaceutically acceptable salts and the above-mentioned esters. Is shown. Such derivatives include, for example, compounds

An amide derivative other than the amide group defined in (I) or (II). Specific examples of the compound having the general formula (I) or (II) of the present invention include, for example, the compounds described in Examples 1 to 872 below. It is not limited. '' In Examples 1 to 872,

Examples: 1, 2, 314, 393, 394, 509, 516, 522, 523 525, 526, 529, 531, 424, 425, 533, 535, 537 538, 539, 540, 541, 542, 543, 544 , 545, 546 550, 554, 555, 556, 557, 558 559 560, 561,

562, 570, 571, 573, 574, 576 577 578, 580,

581, 584, 585, 586, 593, 595 600 601, 608,

616, 621, 643, 644, 649, 651 652 653 655,

664, 667 668 669, 671, 672 673 674 675, 681, 682 683 684, 690, 694 696 697 698,

700 701 702 703, 704, 705, 706 707 708, 710 727 728 730, 732, 733, 734 735 736,

737 743 747 749 751 752 753 754 755,

761 763 765 769 771 773 774 777 782,

784 790 798 799 800 801 802 803 804,

80, 5 807 808 809 810 823 824 825 826, 827 828 829 835, 836 838 839 840 842,

844, 849, 858 and 859, more preferably the examples: 522, 526, 571, 573, 576, 577 586, 593, 600, 621, 649, 651, 667, 669, 671 672, 673,

674, 675, 681, 682, 683, 696, 697 698, 701,

702, 703, 705, 707, 708, 710, 727 733, 734, 735, 736, 737, 747, 751, 771, 774 784, 790, 799, 803, 804, 805, 809, 826, 828 829, 835 , 836, 838, 839, 840, 844, 849, 858 and 859, most preferably

Example 522: tri (4-pyridinyl) -triethanone N- (2- (2-fluoroalirino) _6_ {2- [tri (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone, Example 526 : 4- (pyridinyl) -1-ethanone N- (2-anilino-6- {2-[[4- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone;

Example 586: 1- (4-pyridinyl) -toethanone N- (2- (3-methoxyanilino) -6- {2- [2- (1-pyridinyl) edylidene] hydrazino} -4-pyrimidinyl) hydrazone Example 697: 4- (4-methylsulfamoyl-phenyl) -1-ethanone N- (2-aniline) Reno-1 6- {2-[4- (4-methylsulfamoylofenyl) ethylidene] hydrazino}-

4-pyrimidinyl) hydrazone,

Example 7 07: 1- (4-pyridyl) -triethanone N- (2- (benzo [1,3] dioxol-5-ylamino) -1 6- {2- [tri (4-pyridyl) ethylidene] hydrazino }-4-pyrimidyl) hydrazone,

Example 7 10: 1- (4-ethylsulfonylphenyl) -toluene non-N- (2-anilino-1-6-[2- [1- (4-ethylsulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 73: 4- (4-cyclopropylsulfamoylenyl)-1-ethanone N- (2-anilino-6- {2- [1- (4-cyclopropylsulfamoylylenyl)) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 7 3 5: 1- (4-Methylsulfamoylofenyl) -1-ethanone N- (2- (2,4,

5 -Trifluoroalirino) 1 6-{2- [1- (4-Methylsulfamoyl-phenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 7 36: 1_ (4-methylsulfamoylofenyl) -toethanone N- (2- (2-fluoroallylino) 16- {2- [1- (4-methylsulfamoylofenyl) ) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 7 51: 1 _ (4-ethylsulfamoylenyl) -triethanone N- (2-anilino-6- {2- [1- (4-ethylethylsulfamoylenyl) ethylidene] Hydrazino}-4-pyrimidinyl) hydrazone,

Example 7 7 1: 1- (4-Methylsulfamoylofenyl) -triethanone N- (2- (2,3,4-trifluoroalirino) 1 6- {2- [tri (4-methylsulfuryl) Famoylofenilile) tylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 7 7 4: tri (4-methylsulfamoyl ether) -1 -ethanone N- (2- (2-fluoro-4-chloroanilino) -1-6- {2- [tri (4-methyl Sulfamoyl-phenyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone,

Example 7 84: tri (4-methylsulfamoylofenyl) -triethanone N- (2- (3-methoxyanilino) -1-6- (2- [tri (4-methylsulfamoylofenyl) ethylidene) ] Hydrazino} -4-pyrimidinyl) hydrazone, Example 7 9 9: 1- (4-methylsulfamoylenyl) -toethanone N- (2-anilino-5-ethoxy-6- {2- [1- (4-methylsulfamoylofyl) Enyl) ethylidene] hydrazino}-4-pyrimidinyl) hydrazone,

Example 8 03: 1- (4-methylsulfamoylphenyl) -thuetanone N- (2- (3,5-difluoroanilino) -6- {2- [1- (4- Methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 8 04: 1- (4-methylsulfamoylphenyl) -1-ethanone N- (2- (3,4,5-trifluoroalirino) -6- {2- [tri (4-methylsulfa Moylphenol) ethylene den] hydrazino} -4-pyrimidinyl) hydrazone,

Example 80: 1- (4-methylsulfamoylphenyl) -1-ethanone N- (2-anilino_5-benzyl-6- {2- [1- (4-methylsulfamoylphenyl) ) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 809: 1- (4-methylsulfamoylphenyl) -toethanone- (2- (3,4-difluoroalilino) -6- {2- [1- (4-methylsulfayl Moylphen) ethylidene] hydrazino} 4-pyrimidinyl) hydrazone,

Example 826: 1- (4-methylsulfamoylphenyl) -1-ethanone N- (2- (3-fluoroalirino) 6- {2- [tri (4-methylsulfamoylphenyl) Le) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 82 8: 1- (4-Methylsulfamoylphenyl) -toethanone N- (2- (benzo [1,3] dioxo-l-5-yl-amino) -6- {2_ [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,,

Example 8 35: tri (4-methylsulfamoylphenyl) -1-ethanone N- (2- (2,4-difluoroalirino) -6- {2- [tri (4-methylsulfayl) Moylphen) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 8 36: tri (4-methylsulfamoylphenyl) -1-ethanone N- (2- (2-methoxyanilino) -6- {2- [tri (4-methylsulfamoylphenyl)] Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 83 8: 1- (4-Methylsulfamoylphenyl) -toluene non-N- (2- (2-7-ruorole-5-chloroanilino) -1-6- (2- [1- (4-methyl Sulfamoylphenyl) eti W 03

58 Riden] hydrazino 4-pyrimidinyl) hydrazone,

Example 8 39: 1- (4-methylsulfamoylphenyl) -1 -ethanone N- (2- (4-octaluminylino) -6- {2- [tri (4-methylsulfuryl) Famoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,

Example 8 4 4: 1- (4-methylsulfamoylphenyl) -toethanone- (2- (2-fluoro-4-methoxyanilino) -6- {2- [1- (4-methylsulfamo Ilphenyl) e tyriden] hydrazino} -4-pyrimidinyl) hydrazone,

Example 8 49: 1- (4-methylsulfamoylphenyl) -1--1-ethanone N- (2- (3-methoxy-4-1-fluoroanilino) -6- {2- [1- (4- Methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone, and

Example 8 59: 1- (4-ethylsulfamoylphenyl) -thuetanone N- (2- (3-fluoroanilino) -6- {2- [1- (4-ethylsulfamoylphenyl) ) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

It is. The compound having the general formula (I) or (II) of the present invention can be produced according to the method described below.

Method A is a method for producing compound (I).

Method A

上記式中、 R R²、 R R⁴、 R⁵、 R⁶及び R⁷は、 前述したものと同意義を示 し、 R ^la、 R^2a、 R^3a、 R^4a、 R^5a及び R^6aは、 R '、 R²、 R³、 R⁴、 R⁵及び R⁶の基 に置換基として含まれるアミノ基、 ヒドロキシ基及び/又はカルボキシ基が、 保 護されてもよいアミノ基、 ヒドロキシ基及び Z又はカルポキシ基である他、 R R R³、 R⁴、 R⁵及び R⁶の基の定義における基と同様の基を示し、 Xは、 ハロ ゲン原子、 ァリ一ルスルホネート基又はアルキルスルホネート基を示す。 上記において、 ： ^la、 R²\ R^3a、 R^4a、 R^5a及び R^6aの定義における保護されて もよぃァミノ基の保護基は、 有機合成化学の分野で使用されるァミノ基の保護基 であれば特に限定はされないが、 例えば、 前記ヒドロキシ基のエステルに斯かる 一般的保護基における、 脂肪族ァシル基；芳香族ァシル基；アルコキシ力ルポ二 ル基；アルケニルォキシカルボニル基；ァラルキルォキシ力ルポニル基；シリル 基；又はァラルキル基と同様な基を示すか或いは N， N—ジメチルアミノメチレ ン、 ベンジリデン、 4ーメトキシベンジリデン、 4一二トロべンジリデン、 サリ シリデン、 5—クロロサリシリデン、 ジフエ二ルメチレン、 （5 _クロ口 _ 2— ヒドロキシフエニル） フエニルメチレンのようなシッフ塩基を形成する置換され たメチレン基であり、 好適には、 脂肪族ァシル基、 芳香族ァシル基又はアルコキ シカルポニル基であり、 最も好適には、 アルコキシカルボニル基である。 上記において、 R ^la、 R^2a、 R^3a、 R R^5a及び R^6aの定義における保護されて もよぃヒドロキシ基の保護基は、 有機合成化学の分野で使用されるヒド口キシ基 の保護基であれば特に限定はされないが、 例えば、 前記ヒドロキシ基のエステル に斯かる一般的保護基と同意義を示す。 上記において、 R ^la、 R \ R^3a、 R^4a、 R^5a及び R^6aの定義における保護されて もよいカルポキシ基の保護基は、 有機合成化学の分野で使用される力ルポキシ基 の保護基であれば特に限定はされないが、 例えば、 前記カルボキシ基のエステル に斯かる一般的保護基と同意義を示す。 第 A 1工程は、化合物（ I ) において、 A¹及び A²が酸素原子である化合物（ I a ) を製造する工程であり、 不活性溶媒中、 塩基の存在下、 一般式 （I I I ) を 有する化合物を、 一般式 ( I V) 及び （V) を有する化合物と反応させた後、 所 望により R ^la、 R R^3a、 R^4a、 R^5a及び R^6aにおけるアミノ基、 ヒドロキシ基及 び Z又はカルポキシ基の保護基を除去することにより行なわれる。 化合物 （I I I) を化合物 （I V) 及び （V) と反応させる際に使用される不 活性溶媒は、 反応を阻害せず出発物質をある程度溶解するものであれば特に限定 はないが、 例えば、 ホルムアミド、 Ν,Ν-ジメチルホルムアミド、 Ν,Ν-ジメチルァ セトアミド、 Ν-メチル -2-ピロリドン、 Ν-メチルピロリジノン、 へキサメチルリ ン酸トリアミドのようなアミド類、ジェチルェ一テル、ジイソプロピルエーテル、 テトラヒドロフラン、 ジォキサン、 ジメトキシェタン、 ジエチレングリコールジ メチルエーテルのようなエーテル類、ジクロロメタン、 1， 2—ジクロロェタン、 ジクロロベンゼンのようなハロゲン化炭化水素類であり、 好適には、 アミド類又 はェ一テル類（最も好適には、 Ν,Ν-ジメチルホルムアミド又は Ν，Ν-ジメチルァセ 卜アミド） である。

In the above formula, RR ² , RR ⁴ , R ⁵ , R ⁶ and R ⁷ have the same meanings as described above, and R ^la , R ^2a , R ^3a , R ^4a , R ^5a and R ^6a are R , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , wherein the amino, hydroxy and / or carboxy groups contained as substituents are amino, hydroxy and Z or Other than a carboxy group, it represents the same group as defined in the definition of RRR ³ , R ⁴ , R ⁵ and R ⁶ ; A gen atom, an arylsulfonate group or an alkylsulfonate group. In the above, the protecting group of the amino group which may be protected in the definition of ^la , R ² \ R ^3a , R ^4a , R ^5a and R ^6a is the protecting group of the amino group used in the field of organic synthetic chemistry. If it is not particularly limited, for example, an aliphatic acyl group; an aromatic acyl group; an alkoxy group; an alkenyloxycarbonyl group; an alkenyloxy group; A ruponyl group; a silyl group; or a group similar to the aralkyl group, or N, N-dimethylaminomethylene, benzylidene, 4-methoxybenzylidene, 412 trobenzylidene, salicylidene, 5-chlorosalicylidene, Substituted methylene groups that form Schiff bases such as diphenylmethylene, (5-chloro-2-hydroxyphenyl) phenylmethylene There, preferably, aliphatic Ashiru group, an aromatic Ashiru group or alkoxy Shikaruponiru group, and most preferably, an alkoxycarbonyl group. In the above, the protecting group for the hydroxy group which may be protected in the definition of R ^la , R ^2a , R ^3a , RR ^5a and R ^6a is a protecting group for a hydroxy group used in the field of synthetic organic chemistry. There is no particular limitation as long as it is present, but for example, it has the same meaning as the above general protecting group for the ester of a hydroxy group. In the above, the protecting group of the carboxy group which may be protected in the definition of R ^la , R \ R ^3a , R ^4a , R ^5a and R ^6a is a protecting group of a carbonyl group used in the field of organic synthetic chemistry. There is no particular limitation as long as it is present, but for example, it has the same meaning as the general protecting group for the ester of the carboxy group. The A 1 step, In compound (I), a step of A ¹ and A ² to produce a compound which is an oxygen atom (I a), in an inert solvent in the presence of a base, the general formula (III) Is reacted with a compound having the general formulas (IV) and (V), and then, if desired, the amino group, hydroxy group and Z or carboxy group in R ^la , RR ^3a , R ^4a , R ^5a and R ^6a . It is carried out by removing the protecting group of the group. The inert solvent used for reacting compound (III) with compounds (IV) and (V) is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Amides such as Ν, Ν-dimethylformamide, Ν, Ν-dimethylacetamide, Ν-methyl-2-pyrrolidone, Ν-methylpyrrolidinone, hexamethylphosphoric acid triamide, geethylether, diisopropyl ether, tetrahydrofuran, dioxane, Ethers such as dimethoxyethane and diethylene glycol dimethyl ether; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane and dichlorobenzene; preferably amides or ethers (most preferable). Ν, Ν-dimethylformamide or Ν, Ν-dimethylacetamide) It is.

Bases used in reacting compound (III) with compounds (IV) and (V) include, for example, alkali metal carbonates such as sodium carbonate, potassium carbonate and lithium carbonate; sodium hydrogen carbonate, potassium hydrogen carbonate Alkali metal bicarbonates such as lithium bicarbonate; Alkali metal hydrides such as lithium hydride, sodium hydride, and lithium hydride; sodium hydroxide, potassium hydroxide, barium hydroxide, and hydroxide Alkali metal hydroxides such as lithium; inorganic bases such as sodium fluoride and alkali metal fluorides such as potassium fluoride; sodium methoxide, sodium methoxide, potassium methoxide, potassium methoxide Alkali metal alkoxides such as potassium t-butoxide, lithium methoxide; methyl Mercaptan alkali metals such as sodium rucaptan and ethylmerbutane sodium; N-methylmorpholine, triethylamine, tripropylamine, tributylamine, disopropylethylamine, dicyclohexylamine, N-methylbiperidine, pyridine, 4 _Pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (t-butyl) -4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-ethyl Luaniline, 1,5-diazabicyclo [4.3.0] nonane 5-ene (DBN), 1,4-diazabicyclo [2.2.2] octane (DABC〇), 1,8-dia Organic bases such as zabicyclo [5.4.0] pendant-7-ene (DBU) or organic metal bases such as butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) amide. Preferably, they are alkali metal hydroxides or alkali metal alkoxides (most preferably, sodium hydroxide).

 The reaction temperature at which the compound (III) is reacted with the compounds (IV) and (V) varies depending on the starting compound, the inert solvent used, the type of the base, etc., but is usually from o ° c to 110 (preferably 60 to 100 ° C).

 The reaction time for reacting compound (III) with compounds (IV) and (V) varies depending on the starting compound, the inert solvent used, the type of base, the reaction temperature, etc., but is usually 30 minutes to 48 hours. (Preferably 15 to 24 hours).

The removal of the protecting group for the amino group, the hydroxy group and the Z or carboxy group varies depending on the type, but generally, methods well known in the art of organic synthetic chemistry, for example, TW Green, (Protective Groups in Organic Synthesis), John Wiley & Sons: JFW McOmis, (Protective Groups in Organic Chemistry), P1 enum Press. The step A2 is to produce a compound (lb) in which, in the compound (I), A ¹ and A ² are groups having the formula NR ⁷ — (R ⁷ has the same meaning as described above). Reacting compound (III) with compounds having the general formulas (VI) and (VII) in the presence or absence (preferably in the presence) of an inert solvent, It is carried out by removing the protecting group of the amino group, hydroxy group and Z or carboxy group in R ^Ia , R ² \ RR ^4a , R ^5a and R ^6a .

 The inert solvent used when reacting compound (III) with compounds (VI) and (VII) is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. The same inert solvents as those used in Step A1 of Method A can be used.

Reaction temperature for reacting compound (III) with compounds (VI) and (VII) The degree varies depending on the starting compound, the inert solvent used, and the like, but is usually from 0 ° C. to 15 Ot: (preferably from 60 ° C. to 100 ° C.).

 The reaction time when the compound (III) is reacted with the compounds (VI) and (VII) varies depending on the starting compound, the inert solvent used, the reaction temperature, etc., but is usually 30 minutes to 48 hours. (Preferably 24 to 48 hours).

Amino group, removal of the protecting group of hydroxy group and Z or Karupokishi group, Ri ^a desired in the A Act A 1 ^{step, R 2a, R 3a, R} 4a, an amino group in the R ^5a and R ^6a, hydroxy It is carried out in the same manner as the method for removing the protecting group and the protecting group of Z or carboxy group. Step A3 is a step of producing a compound having the general formula (VIII), and converting compound (III) into hydrazine monohydrate in the presence or absence (preferably, absence) of an inert solvent. It is carried out by reacting with a hydrate.

 The inert solvent used in the above reaction is not particularly limited as long as it does not hinder the reaction and dissolves the starting materials to some extent. Examples thereof include formamide, Ν, Ν-dimethylformamide, Ν, Ν- Amides such as dimethylacetamide, ethers such as getyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether, dichloromethane, 1,2-dichloroethane, dichlorobenzene Such as halogenated hydrocarbons, aromatic hydrocarbons such as benzene, toluene and xylene, methanol, ethanol, η-propanol, i-propanol, η-butanol, topbutanol, isomayl alcohol, Diethylene glycol, glycerin, octanol, Hexanol click port, an alcohol such as Mechiruse port cellosolve, preferably, § alcohol compound (most preferably, ethanol) is.

The reaction temperature in the above reaction varies depending on the starting compound, the inert solvent used and the like, but is usually from room temperature to 120 ° C (preferably 50 ° C to 110 ° C). The reaction time in the above reaction varies depending on the starting compound, the inert solvent used, the reaction temperature and the like, but is usually 30 minutes to 24 hours (preferably 1 hour to 3 hours). Step A4 is a step for producing a compound (I b-1) in which A ¹ and A ² are groups having the formula —NH— in the compound (I). In the presence of an inert solvent, the compound (VIII the), it was reacted with a compound having the general formula (IX) and (X), optionally more ^{R la, R 2a, R 3a} , R 4a, an amino group in the R ^5a and R ^6a, hydroxy group and Z or It is carried out by removing the protecting group of the carboxy group.

 The inert solvent used when reacting compound (VIII) with compounds (IX) and (X) is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Amides such as formamide, Ν, Ν-dimethylformamide, Ν, Ν-dimethylacetamide, ethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, ethers such as diethylene glycol dimethyl ether, dichloromethane, Halogenated hydrocarbons such as 1,2-dichloroethane and dichlorobenzene, aromatic hydrocarbons such as benzene, toluene, and xylene, methanol, ethanol, η-propanol, i-propanol, diethylene glycol, and glycerin Alcohols such as dimethylsulfo Sid, sulfoxides such as sulfolane, nitriles such as acetonitrile, ethyls formate, ethyl acetate, propyl acetate, butyl acetate, esters such as ethyl carbonate or a mixed solvent of the above solvents, and preferably a mixed solvent of Ethers (most preferably dioxane).

 The reaction temperature at which the compound (VIII) is reacted with the compounds (IX) and (X) varies depending on the starting compound, the inert solvent used and the like, but is usually from room temperature to 120 ° C (preferably 90 ° C). To 100.C).

The reaction time when the compound (VIII) is reacted with the compounds (IX) and (X) varies depending on the starting compound, the inert solvent used, the reaction temperature, etc., but is usually from 1 hour to 24 hours (preferably , 15 hours to 24 hours). Removal of the protecting group for the amino group, the hydroxy group and / or the carboxy group may be carried out, if desired, in the above-mentioned Method A, Step A1, by the amino group, the hydroxy group in R ^la , R ^2a , R ^3a , R ^4a , R ^5a and R ^6a . And the method for removing the protecting group of Be done. After the completion of the reaction in each step in Method A, each target compound is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, then an immiscible organic solvent such as water and ethyl acetate is added, and the organic layer containing the target compound is separated. It is obtained by washing with water and the like, drying with anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogen carbonate, etc., and distilling off the solvent. If necessary, the obtained target compound can be combined with a conventional method, for example, recrystallization, reprecipitation, etc., using a method commonly used for separation and purification of organic compounds as appropriate. It can be separated and purified by elution.

Method B is a method for producing compound (II).

B method

上記式中、 R R^la、 R²、 R^2a、 R³、 R^3a、 R⁴、 R^4a、 R⁵、 R^5a、 R⁶、 R^6a、 R 及び Xは、 前述したものと同意義を示す。 第 B1工程は、 化合物 （I I) において、 A¹及び A²が酸素原子である化合物 (I I a) を製造する工程であり、 不活性溶媒中、塩基の存在下、 一般式 （XI) を有する化合物を、 化合物 （I V) 及び（V) と反応させた後、 所望により R^la、 R^2a、 R^3a、 R R^5a及び R^6aにおけるアミノ基、 ヒドロキシ基及び/又は力ルポ キシ基の保護基を除去することにより行なわれ、 本工程は、 前記 A法第 A 1工程 と同様に行われる。 第 B 2工程は、 化合物 （I I) において、 A¹及び A²が式— NR⁷—を有する基 (R⁷は、 前述したものと同意義を示す。） である化合物 （l i b) を製造するェ 程であり、 不活性溶媒の存在下又は非存在下 （好適には、 存在下）、 化合物 （X I) を、 化合物 （V I) 及び （V I I) と反応させた後、 所望により R^la、 R^2a、

In the above formula, RR ^la , R ² , R ^2a , R ³ , R ^3a , R ⁴ , R ^4a , R ⁵ , R ^5a , R ⁶ , R ^6a , R and X are as defined above. . Step B1 is a step for producing a compound (IIa) in which A ¹ and A ² are oxygen atoms in the compound (II), and the compound represented by the general formula (XI) in an inert solvent in the presence of a base: Is reacted with compounds (IV) and (V), and if necessary, protection of amino, hydroxy and / or carbonyl groups in R ^la , R ^2a , R ^3a , RR ^5a and R ^6a This step is carried out by removing the group, and this step is carried out in the same manner as the above-mentioned Method A, Step A1. Step B2 is to produce a compound (lib) wherein A ¹ and A ² in the compound (II) are groups having the formula —NR ⁷ — (R ⁷ has the same meaning as described above). After reacting compound (XI) with compounds (VI) and (VII) in the presence or absence (preferably in the presence) of an inert solvent, R ^la and R ^2a ,

This step is carried out by removing the protecting group for the amino group, the hydroxy group and / or the carboxy group in R ^3a , R ^4a , R ^5a and R ^6a , and this step is carried out in the same manner as the above-mentioned Method A, Step A2. Step B3 is a step of producing a compound having the general formula (XII), and converting compound (XI) to hydrazine 1 in the presence or absence (preferably, absence) of an inert solvent. This step is carried out in the same manner as the above-mentioned Method A, Step A3. Step B4 is a step of producing a compound (IIb-l) of the compound (II), wherein A ¹ and A ² are groups having the formula —NH—, and in the presence of an inert solvent, the compound After reacting (XII) with compounds (IX) and (X), if desired, the amino group, hydroxy group and Z or carboxy group in R ^la , -R ^2a , R ^3a , R ^4a , R ^5a and R ^6a This step is performed by removing the protecting group of the group, and this step is performed in the same manner as in the above-mentioned Method A, Step A4. After completion of the reaction in each step in Method B, each target compound is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, and then an immiscible organic solvent such as water and ethyl acetate is added to separate the organic layer containing the target compound. After washing with water etc., anhydrous magnesium sulfate, It is obtained by drying over anhydrous sodium sulfate, anhydrous sodium hydrogen carbonate, etc., and distilling off the solvent. If necessary, the obtained target compound can be obtained by a conventional method, for example, recrystallization, reprocessing.

Separation and purification can be carried out by appropriately combining ordinary methods commonly used for separation and purification of organic compounds such as precipitation, applying chromatography, and eluting with an appropriate eluent.

Method C, the compound is a starting compound of Method A in (III), R ^5a is a compound which is a group having the formula one NH- R ^8a (I lia) and R ^5a are the formula one - having a R ^8a This is a method for producing a compound (IIIb) which is a group represented by

In the above formula, R ^5a , R ^6a and X have the same meanings as described above, and R ^8a is a group in which the amino group, hydroxy group and Z or carboxy group contained as substituents in R ⁸ are protected. Other than the amino group, hydroxy group and Z or carboxy group, and the same groups as defined in the definition of R ⁸ , and D, represents an oxygen atom or a sulfur atom. Step CI is a step of producing the compound (Ilia) in an inert solvent (preferably ketones such as acetone, amides, ethers, alcohols, halogenated hydrocarbons, Water or a mixed solvent of the above solvents, most preferably a mixed solvent of water and ketones), a compound having the general formula (XIII) and a compound having the general formula (XIV) at room temperature to 80 ° C. (Preferably 40 ° C to 60 ° C) for 3 hours to The reaction is carried out for 24 hours (preferably 15 hours to 20 hours). Step C2 is a step of producing compound (IIIb), and compound (XIII) in an inert solvent (preferably ketones or ethers, most preferably ketones). 2 hours to 24 hours (preferably 15 hours to 20 hours) at room temperature to 80 ° C. (preferably 40 ° C. to 60 ° C.) and a compound having the general formula (XV) This is done by reacting. After the completion of the reaction in each step in Method C, each target compound is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, then an immiscible organic solvent such as water and ethyl acetate is added, and the organic layer containing the target compound is separated. It is obtained by washing with water and the like, drying with anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogen carbonate, etc., and distilling off the solvent. If necessary, the desired compound obtained can be combined with a conventional method, for example, recrystallization, reprecipitation, etc., which is commonly used for the separation and purification of organic compounds, and then applied to the appropriate eluent by chromatography. It can be separated and purified by elution.

Method D is a process for producing compound (X I) which is a starting compound of method B.

 D

In the above formula, R ^5a , R ^6a and X have the same meanings as described above, and R ¹² represents a lower alkyl group. Step D1 is a step of preparing a compound having the general formula (XVIII), and is performed in an inert solvent (preferably, an amide, ether, alcohol, or halogenated compound). W

70 hydrocarbons, most preferably alcohols) in the presence of a base (preferably Al metal alkoxides, Al metal carbonates or organic bases; most preferably , An alkali metal alkoxide), a compound having the general formula (XVI) and a compound having the general formula (XVI I) at room temperature to 12 O (preferably 80 to 100) for 1 hour to 48 hours (preferably Is carried out for 10 hours to 24 hours). Step D2 is a step of producing compound (XI),

 (i) When X represents a halogen atom, in the presence or absence of an inert solvent (preferably in the presence of ethers, aromatic hydrocarbons or halogenated hydrocarbons), The compound (XVIII) is a halogenating agent (preferably a phosphorus oxyhalide such as phosphorus oxychloride, phosphorus oxybromide or phosphorus oxyiodide, most preferably phosphorus oxychloride) and 20 to The reaction is carried out at 120 (preferably 80 ° C. to 100 ° C.) for 30 minutes to 24 hours (preferably 4 hours to 8 hours) to convert the hydroxy group in compound (XVI II) into a halogen atom Done by

(ii) When X represents an arylsulfonate group or an alkylsulfonate group, the compound (XVIII) in the presence or absence of an inert solvent (preferably in the presence of a halogenated hydrocarbon) To a sulfonylating agent (preferably, tosyl chloride, 2,4,6-trimethylbenzenesulfonyl chloride, 2,4,6-triisopropylbenzenesulfonyl chloride, methanesulfonyl chloride, trifluoromethanesulfonyl chloride, etc. Most preferably 2,4,6-triisopropylbenzenesulfonyl chloride) and 0 ° 〇 to 80 ° 0 (preferably from room temperature to 40 ° C) for 30 minutes to 24 hours ( (Preferably 4 hours to 8 hours) by reacting to convert the hydroxy group in compound (XVIII) to an arylsulfonate group or an alkylsulfonate group. Ri is done. After completion of the reaction in each step in Method D, each target compound is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, and then an immiscible organic solvent such as water and ethyl acetate is removed. In addition, the organic layer containing the target compound is separated, washed with water or the like, dried over anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogen carbonate, or the like, and then the solvent is distilled off. If necessary, the obtained target compound can be combined with a conventional method, for example, recrystallization, reprecipitation, etc., using a method commonly used for separation and purification of organic compounds as appropriate. It can be separated and purified by elution.

The method E is a method for producing a compound (XV la) in which R ^5a is a group having the formula —NH R ^8a in the compound (XVI) which is a starting compound of the method D.

 E method H

 HE 1 丄 主., _ H

 R 8a— -NH, 8a '

 R

(XIX) NH ₂

 (XVIa)

In the above formula, R ^Sa has the same meaning as described above. Step E1 is a step for producing the compound (XVIa) in an inert solvent (preferably amides, ethers, alcohols, water or a mixed solvent of the above solvents; Preferably, an amide or alcohol) or a compound having the general formula (XIX) is converted to a guanidine derivative (for example, cyanamide ゃ HCl 1 H-pyrazole-1-force lipoxyamidine, 3,5-dimethylpyrazole nitrate-1-carboxylate) A carboxamidine compound activated by a pyrazole such as amidine; preferably, cyanamide or 1 H-pyrazole-l-carboxamidine hydrochloride; and room temperature to 120 ° C (preferably 8 The reaction is carried out at 0 ° C. to 100 ° C. for 1 hour to 48 hours (preferably 10 hours to 24 hours). After the completion of the reaction in each step in Method E, each target compound is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, and then an immiscible organic solvent such as water and ethyl acetate is added to separate the organic layer containing the target compound. After washing with water etc., anhydrous magnesium sulfate, It is obtained by drying over anhydrous sodium sulfate, anhydrous sodium hydrogen carbonate, etc., and distilling off the solvent. If necessary, the obtained target compound can be combined with a conventional method, for example, recrystallization, reprecipitation, etc., using a method commonly used for separation and purification of organic compounds as appropriate. It can be separated and purified by elution.

The method F is a method for producing the compounds (IV) and (V), which are the starting compounds of the methods A and B.

 F method 0 R 1a

 Step F 1

 HO,

 R R 2a 2a

H ₂ N-OH "NR

 (XX) (IV)

0 R 3a

 Step F 2

 HO,, 4a

H ₂ N-OH

 (XXI) (V)

In the above formula, R ^la , R ^2a , R ^3a and R ^4a have the same meaning as described above. Step F1 is a step of producing the compound (IV). In an inert solvent (preferably ethers or alcohols), the compound having the general formula (XX) is treated with hydroxyamine at room temperature to 12 The reaction is carried out at 0 ° C (preferably 60 ° C to 100 ° C) for 30 minutes to 24 hours (preferably 15 hours to 18 hours). The step F2 is a step of producing the compound (V), and is carried out by reacting the compound having the general formula (XXI) with hydroxylamine in an inert solvent. This is performed in the same manner as in the F1 step. After the completion of the reaction in each step in Method F, each target compound is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, and then an immiscible organic solvent such as water and ethyl acetate is removed. In addition, the organic layer containing the target compound is separated, washed with water or the like, dried over anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous sodium hydrogen carbonate, or the like, and then the solvent is distilled off. If necessary, the desired compound obtained can be combined with a conventional method, for example, recrystallization, reprecipitation, etc., which is commonly used for the separation and purification of organic compounds, and then applied to the appropriate eluent by chromatography. It can be separated and purified by elution. The starting compounds (VI), (VI1), (I), (X), (XIII) to (XVII) and ή (ήιχ) to (χχιι) are known compounds or known compounds. It is easily manufactured according to a method or a similar method. The invention's effect

 The pyrimidine derivative having the above general formula (I) or (II), its pharmaceutically acceptable salt, its ester or other derivative of the present invention has excellent MLR inhibitory activity, low cytotoxicity, Inhibitors of transplant rejection in transplantation, organ transplantation, etc., inhibitors of cancer cells by selective cell killing activity (eg, inhibitors of cancer-affected lymphocytes), or rheumatoid arthritis, an inflammatory disease And organ-specific autoimmune diseases (e.g., multiple sclerosis, inflammatory bowel disease, diabetes, glomerulonephritis, primary biliary cirrhosis, chronic active hepatitis, pernicious anemia, Hashimoto's thyroiditis, atrophic gastritis) , Myasthenia gravis, psoriasis or Shederdalen syndrome), non-organ-specific autoimmune diseases (eg, systemic lupus erythematosus), allergic diseases (eg, rhinitis, asthma or atopy) Useful as a preventive and / or therapeutic agent for atopic dermatitis (preferably, an agent for suppressing rejection of transplants in bone marrow transplantation, organ transplantation, etc. or an agent for preventing and / or treating rheumatoid arthritis) It is. Industrial applicability

When the compound of the present invention having the general formula (I) or (II), a pharmaceutically acceptable salt thereof, an ester or other derivative thereof is used as the above-mentioned therapeutic or prophylactic agent, Is mixed with an appropriate pharmacologically acceptable excipient, diluent, etc. For example, they can be administered orally by means of tablets, capsules, granules, powders or syrups, or parenterally by injections or suppositories.

These preparations may contain excipients (eg, lactose, sucrose, dextrose, mannitol, sorbitol), sugar derivatives such as starch; corn starch, potato starch, starch derivatives such as starch, dextrin; Organic excipients such as gum arabic; dextran; pullulan; and silicate derivatives such as light anhydrous silicic acid, synthetic aluminum silicate, calcium silicate, magnesium silicate and magnesium aluminate; hydrogen phosphate Phosphates such as calcium; carbonates such as calcium carbonate; inorganic excipients such as sulfates such as calcium sulfate; and lubricants (eg, stearic acid, calcium stearate) Metal stearate, such as magnesium stearate; talc; colloidal silica Waxes such as veegum and gay ；; boric acid; adipic acid; sulfates such as sodium sulfate; glycol; fumaric acid; sodium benzoate; DL leucine; fatty acid sodium salt; sodium lauryl sulfate; Lauryl sulfate; silicic acid such as silicic anhydride and silicic acid hydrate; and the above-mentioned starch derivatives.) Binders (eg, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinylpyrrolidone, macrogol) And the same compounds as the above-mentioned excipients), disintegrants (for example, low-substituted hydroxypropylcellulose, propyloxylmethylcellulose, carboxymethylcellulose calcium, internal crosslinkable lipoxylmethylcellulose sodium) Cell-derived derivatives such as sodium; carboxylmethyl starch, sodium carboxylmethyl starch, chemically modified starches such as cross-linked polybierpyrrolidone, and celluloses.) Stabilizers (methylparaben, propyl Paraoxybenzoic acid esters such as parabens; alcohols such as chlorobutanol, benzyl alcohol, and phenylethyl alcohol; benzonalconium chloride; phenols such as phenol and cresol; thimerosal; dehydroacetic acid; Acids, etc.) and flavoring agents (for example, commonly used sweeteners, acidulants, flavors, etc.). ), Manufactured by well-known methods using additives such as diluents. The dosage varies depending on symptoms, age, etc., but in the case of oral administration, the lower limit is 0.1 mg (preferably 0.5 mg) per day, the upper limit is 400 Omg (preferably 40 Omg) per dose. In the case of intravenous administration, a minimum dose of 0.1 mg (preferably 0.05 mg) per day and a maximum dose of 50 mg (preferably 30 mg) per day for adults should be 1 mg / day. It is desirable to administer it up to 6 times according to the symptoms. BEST MODE FOR CARRYING OUT THE INVENTION

 Hereinafter, the present invention will be described in more detail with reference to Examples, Reference Examples, and Test Examples, but the scope of the present invention is not limited thereto. The equipment used to measure the various data and the measurement conditions for the liquid mouth are as follows. Measurement conditions for liquid chromatography and mass spectrometry

 The liquid chromatograph-to-mass spectrometry (LCMS) measuring device used was HP-1100 LCZMSD manufactured by Hewlett-Packard. The column used was CD-C18 manufactured by Inktact in a reverse layer system. The analytical conditions were a column temperature of 40 ° C, and acetonitrile and water (containing 0.01% trifluoroacetic acid) as the mobile phase. The flow rate was 1.5 ml / min and the acetonitrile was a linear gradient from 8% to 99% for 10 minutes. Atmospheric pressure chemical ionization (APC I) was used for the mass spectrometer. Measurement device for nuclear magnetic resonance spectrum (hereinafter abbreviated as Ή-band R spectrum)

Ή-Awake R spectrum data were measured with a JEOL JNM-GX 270 FT-NMR or a Variance 400 instrument. Chemical shift values are described at <5 ppm using tetramethylsilane as a reference substance. Fission patterns are indicated by s for singlet, d for doublet, t for triplet, q for quadruple, etc. In the following, DMF means dimethylformamide. Example 1

 1- (4-pyridinyl) _1-ethanone N- (4- (2-methoxyanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -2-pyrimidinyl) hydrazone

 N- (2,6-dihydrazinopyrimidin-4-yl) _ (2-methoxyphenyl) amine (78 mg, 0.3 mol ol) prepared in Reference Example 2 was dissolved in dioxane (2 ml) and 4-acetyl was dissolved. 'Pyridine (0.198 ml, 1.8 ol) was added, and the mixture was refluxed for 15 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was suspended by adding a mixed solvent of ether and ethyl acetate. The precipitated solid was pulverized, collected by filtration, and washed again with a mixed solvent of ether and ethyl acetate to obtain the desired product (40 mg, 29 mg).

'H-NMR spectrum _{(270 MHz, DMS0 - d 6} ) <5ppm: 9.77 (s, 1H), 9.60 (s, 1H), 8. 75-8.72 (m, 1H), 8.61 (d, 4H, J = 5.6 Hz), 8.41 (s, 1H), 7.82-7.78 (m, 4H), 7.03-6.97 (m, 3H), 6.59 (s, 1H), 3,89 (s, 3H), 2.30 (s, 6H )

MS (APCI, m / z): 468 (M + 1) +

 HPLC (reversed): Rt. (Min) = 2.78. Example 2

 1- (4-pyridinyl) -1 -ethanone-(4-anilino-6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -2-pyrimidinyl) hydrazone

Hydrazine monohydrate (3 ml) was added to N- (2,6-dichloropyrimidine-4-yl) -phenylamine (480 mg, 2 mmol) produced in Reference Example 3, and the mixture was added at 90 ° C. Stirred for hours. The reaction system was cooled to room temperature, water was added to the reaction solution, and the precipitated solid was collected by filtration. The obtained solid was washed with water and ethyl acetate, and dried under reduced pressure to obtain N- (2,6-dihydrazino-pyrimidine-4-yl) -phenylamine as a crude product. This was dissolved in dioxane (5 ml), 4-acetylpyridine (1.7 ml, 12 mol) was added, and the mixture was heated under reflux for 15 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was suspended in a mixed solvent of ether and ethyl acetate. The precipitated solid was pulverized, collected by filtration, and washed again with a mixed solvent of ether and monoethyl acetate to obtain the desired product. -NMR spectrum (270 MHz, DMSO-d ₆ ) άρριη: 8.79-8.75 (m, 5H), 8.41-8.33

(m, 2H), 8.03-8.00 (m, 2H), 7.84-7.82 (m, 2H), 7.45-7.39 (m, 2H), 7.17-

7.11 (m, 1H), 6.43 (s, 1H), 2.48 (s, 6H)

 MS (APCI, m / z): 438 (M + D +

 HPLC (reversed): Rt. Din) = 2.79. Example 3

 3-Hydroxy-4-ditobenzaldehyde N- (4-anilino-6- {2-[(3-hydroxy-4-ditophenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone Prepared in Reference Example 4 N- (2,6-dihydrazinopyrimidin-4-yl) -phenylamine (23 mg, 0.1 bandol) was dissolved in dioxane (1 ml) and 3-hydroxy-4-nitrobenzaldehyde (0.35 And heated under reflux for 15 hours. After the reaction, the solvent was distilled off under reduced pressure, and a mixed solvent of ethyl monoacetate was added to the residue to suspend. The precipitated solid was pulverized, collected by filtration, and washed again with a mixed solvent of ether and monoethyl acetate to obtain a target substance.

Ή- negation R spectrum _{(270 MHz, DMSO- d 6)} Sppm: 11.18 (s, 1H), 11.02 (s, 1H), 9.29 (s, 1H), 7.97-8.10 On, 4H), 7.66 (d, 2H , J = 8.3 Hz), 7.31-7.34 (m, 6H), 6.95 (t, 1H, J = 6.3 Hz), 6.19 (s, 1H)

 MS (APCI, m / z): 530 (M + l

 HPLC (reversed): Rt. (Min) = 4.40. Example 4

3-Hydroxy-4-nitrobenzaldehyde N- [4- {2 _ [(3-hydroxy-4-nitrophenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimigere] Reference Example 2 The N- (2,6-dihydrazinopyrimidin-4-yl) _ (2-methoxyphenyl) amine (26 mg, 0.1 mmol) prepared in the above was dissolved in dioxane (1 ml) and the mixture was dissolved in 3-hydroxy-4- Nitrobenzaldehyde (0.35 mmol) was added, and the mixture was heated under reflux for 15 hours. reaction Thereafter, the solvent was distilled off under reduced pressure, and a mixed solvent of ether and monoethyl acetate was added to the residue to suspend. The precipitated solid was ground, collected by filtration, and washed again with a mixed solvent of ether and monoethyl acetate to obtain the desired product.

 MS (APCI, m / z): 560 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.45. Example 5

 4-Hydroxybenzaldehyde N- (4-anilino-6- {2-[(4-hydroxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

 N- (2,6-Dihydrazinopyrimidine-4-yl) -phenylamine (23 mg, 0.1 t ol) prepared in Reference Example 4 was dissolved in dioxane (1 ml) to give 4-hydroxybenzaldehyde. (0.35 t) was added and the mixture was refluxed for 15 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was suspended by adding a mixed solvent of ether and ethyl acetate. The precipitated solid was pulverized, collected by filtration, and washed again with a mixed solvent of ether and ethyl acetate to obtain the desired product. MS (APCI, m / z): 440 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.70. -Thereafter, the same reaction as in Example 4 was carried out and purified to obtain the desired products of Examples 6 to 390. Example 6: 4-Hydroxybenzaldehyde N- [4_ {2-[(4-hydroxyphenyle) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone MS (APCI, m / z) : 470 (M + l

HPLC (reversed): Rt. (Min) = 3.74. Example 7: 5-Hydroxy-2-nitrobenzaldehyde N- (4-anilino-6- {2-[(5-hydroxy-2-nitrophenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρριη: 11.29 (s, 1H), 11.15 (s, 1H), 11.02 (S, 1H), 10.99 (s, 1H), 9.31 (s, 1H), 8.68 (s, 1H), 8.62 (s, 1H), 8.06 (d, 2H, J = 8.9 Hz) 7.89 (d, 2H, J = 8.4 Hz), 7.54 (d, 1H, J = 2.

5 Hz), 7.41 (d, 1H, J = 2.6 Hz), 7.32 (t, 2H, J = 7.8 Hz), 6.18-6.92 (m, 3H), 6.18 (s, 1H)

MS (APCI, m / z) 530 (M + D +

 HPLC (reversed) Rt. (Min) = 4.01. Example 8: 5-Hydroxy-2-nitrobenzaldehyde N- [4- {2-[(5-hydroxy-2-nitrophenyl) methylidene] hydrazino 6- (2-methoxyanilino) -2-pyrimidinile ] Hydrazone

-NMR spectrum _{(270 MHz, DMSO- d 6)} (5ppm 11.23 (s, 1H), 11.08 (s, 1H), 10.99 (s, 1H), 10.96 (s, 1H), 8.65 (s, 1H), 8.59 (s, 1H), 8.35 (s, 1H), 8.02 (d, 2H, J = 8.9 Hz), 7.38-7.49 (m, 2H), 6.90-7.06 On, 6H), 6.3

6 (s, 1H), 3.85 (s, 3H)

MS (APCI, m / z) 560 (M + D +

 HPLC (reversed) Rt. (Rain) = 4.00. Example 9 2,3-Dihydro-1,4-benzoxazine-6-carpaldehyde N- (4-anilino-6- {2- [2,3-dihydro-1,4-benzodioxin-ylmethylidene] hydrazino} -2-pyrimidinyl) hydrazone ·

MS (APCI, m / z) 524 (M + D +

HPLC (reversed) Rt. (Rain) = 4.29. Example 10: 2,3-Dihydro-1,4-benzoxazine-6-hydroxylpaldehyde N- [4- {2- [2,3-dihydro-1,4-benzodioxin-6-ylmethylidene] hydrazino}- 6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z) 554 (M + D +

HPLC (reversed) Rt. (Min) = 4.35. Example 11: 2,5-Dimethoxybenzaldehyde N- (4-anilino-6- {2-[(2,5-dimethoxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 528 (M + D +

 HPLC (reversed): Rt. (Min) = 4.47. Example 12: 2,5-Dimethoxybenzaldehyde [4- {2-[(2,5-dimethoxyphenylyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

 MS (APCI, m / z): 558 (M + D +

 HPLC (reversed): Rt. (Min) = 4.54. Example 13: 3- {4-[(2- {4-anilino-6- [2-({4- [3-hydroxy-3-oxo-toprobenyl] phenyl} methylidene) hydrazino] -2 " -Pyrimidinyl} hydrazono) methyl] phenyl} -2 -Probenoic acid

 MS (APCI, m / z): 548 (M + D +

 HPLC (reversed): Rt. (Min) = 3.77. Example 14: 3- [4-({2_ [2_ [2-({4- [3-hydroxy-3-oxo-toprobenyl] phenyl} methylidene) hydrazino] -6- (2-methoxyanilino )-4-Pyrimidinyl] hydrazono} methyl) phenyl] -2-Probenoic acid '

 MS (APCI, m / z): 578 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.79. Example 15: 6-chloro-1,3-benzodioxole-5-carpaldehyde N- (4-ani "lino-6- {2-[(6-cyclo-1,3-benzodioxo) 1-5-yl) methylidene] hydrazino}-2-pyrimidinyl) hydrazone

Ή- 丽 R spectrum (270 MHz, DMS0-d ₆ ) ρριιι: 10.89 (s, 1H), 10.81 (s, 1H), 9.10 (s, 1H), 8.32 (s, 1H), 8.28 (s, 1H) ), 7.85-7.88 (m, 2H), 7.46 (s, 1H), 7.34 (s, 1H), 7.20 (t, 2H, J = 7.8 Hz), 7.05-7.06 (m, 2H), 6.86 (t, 1H, J = 7.1 Hz), 6.07 (s, 5H)

MS (APCI, m / z): 564 (M + l) +

HPLC (reversed): Rt. (Min) = 4.66. Example 16: 6-chloro-1,3-benzodioxoyl-5-phenolaldehyde N- [4- {2-[(6-chloro-1,3,3-benzodioxol-5-yl) methylidene] ] Hydrazino} -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone

- NMR spectrum _{(270 MHz, DMS0 - d 6} ) δ ρηι: 10.93 (s, 1H), 10.85 (s, 1H), 8.28-8.40 (m, 3H), 7.51 (s, 2H), 6.93-7.12 (m , 5H), 6.44 (s, 1H), 6.22 (s, 1H), 6.15 (s, 4H), 3.88 (s, 3H)

 MS (APCI, m / z): 594 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.76. Example 17: 4-oxo-4H-octamen-3-carbaldehyde N- (4-anilino-6- {2-[(4-oxo-4H-octamen-3-yl) methylidene] hydrazino } -2-pyrimidinyl) hi

MS (APCI, m / z): 544 (Mll) l

 HPLC (reversed): Rt. (Rain) = 4.27. Example 18: 3-phenyl-1H-pyrazole-4-carpaldehyde N- (4-anilino-6- {2-[(3-phenyl-1H-pyrazol-4-yl) methylidene] hydrazino 2-pyrimidi Nyl) hydrazone trifluoroacetate

MS (APCI, m / z): 540 (M + D +

HPLC (reversed): Rt. (Min) = 3.90. Example 19: 3-Phenyl-1H-pyrazole-4-carpaldehyde N- (4- (2-methoxyanilino) -6- {2-[(3-phenyl-1H-pyrazole-4-yl) methylidene] Hydrazino} _2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z) :, 570 (M + D + HPLC (reversed): Rt. (Min) = 3.91. Example 20: 4-Hydroxy-3-nitrobenzaldehyde N- (4-anilino-6- {2-[(4-hydroxy-3-ditrophenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetic acid salt

MS (APCI, m / z): 530 (M + D +

HPLC (reversed): Rt. (Min) = 4.24. Example 21 4-Hydroxy-3-nitrobenzaldehyde N- [4- {2 _ [(4-hydroxy-3-nitrophenyl) methylidene] hydrazino 6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone trifluorozol Acetate

MS (APCI, m / z): 560 (M + D +

HPLC (reversed): Rt. (Min) = 4.26. Example 22: 2-Methoxybenzaldehyde N- (4-anilino-6- {2 _ [(2-methoxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 468 (M + l) +

HPLC (reversed): Rt. (Min) = 4.54. Example 23: 2-Methoxybenzaldehyde N- (4- (2-methoxyphenyl) -6- {2-[(2-methoxyphenyl) methylidene] hydrazino} _2_pyrimidinyl) hydrazone MS (APCI, m / z): 498 (M + D +

HPLC (reversed): Rt. (Min) = 4.83. Example 24: 2-Fluorobenzaldehyde N- (4-anilino-6- {2-[(2_fluorophenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 444 (M + l) +

HPLC (reversed): Rt. (Min) = 4.41. Example 25: 2-Fluorobenzaldehyde N_ [4- {2-[(2-fluorophenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone MS (APCI, m / z ): 474 (M + D +

HPLC (reversed): Rt. (Min) = 4.46. Example 26: 4-hydroxy-3,5-dimethoxybenzaldehyde N- (4-anilino-6- {2-[(4-hydroxy_5-dimethoxyphenyl) methylidene] hydrazino} -2_pyrimidinyl) hydrazone

MS (APCI, m / z): 560 (M + D +

HPLC (reversed): Rt. (Min) = 3.61. Example 27: 4-Hydroxy_3,5-dimethoxybenzaldehyde N- [4- {2-[(4-hydroxy-3,5-dimethoxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino -2-Pyrimidinyl] hydrazone

MS (APCI, m / z): 590 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.64. Example 28: 4-{[2- (4-anilino-6- {2-[(4_carboxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazono] methyl} benzoic acid

MS (APCI, m / z): 496 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.58. Example 29: 4 _ ({2- [4- {2-[(4-potoxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazono} methyl) benzoic acid

MS (APCI, m / z): 526 (M + l) +

HPLC (reversed): Rt. (Min) = 3.59. Example 30: 3-Hydroxy-4-methoxybenzaldehyde N- (4-anilino-6- {2-[(3-hydroxy-4-methoxyphenyl) methylidene] hydrazino} -2-pyrimige Le) Hydrazone

 MS (APCI, m / z): 500 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.78. Example 31: 3-Hydroxy-4-methoxybenzaldehyde N- [4- {2-[(3-hydroxy-4-methoxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] Hydrazone

MS (APCI, m / z): 530 (M + D +

HPLC (reversed): Rt. (Min) = 3.86 Example 32: 2_ [2-({2- [4-anilino-6- (2-{[2- (2-hydroxy-2-oxoxetoxy)] Phenyl] methylidene} hydrazino) -2-pyrimidinyl] hydrazono} methyl) phenoxy] acetic acid

 MS (APCI, m / z): 556 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.92. Example 33: 2- [2-({2- [2- (2-{[2_ (2-hydroxy-2-oxoethoxy) phenyl] methylidene} hydrazino) -6- (2-methoxyanilino) -4-pyrimidinyl] Hydrazono} methyl) phenoxy] acetic acid

MS (APCI, m / z): 586 (M + l) +

HPLC (reversed): Rt. (Min) = 3.93. Example 34: 4-Chlorobenzaldehyde N- (4-anilino-6- {2-[(4-chlorophenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 476 (M + D +

HPLC (reversed): Rt. (Min) = 4.80. Example 35: 4-Chlorobenzaldehyde N- [4- {2-[(4-Chlorophenyl) methylidene] hydrazino 6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone MS (APCI, m / z): 506 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.84. Example 36: 3-Hydroxybenzaldehyde N- (4-anilino-6- {2-[(3-hydroxyphenyl) methylidene] hydrazino 2-pyrimidyl) hydrazone

MS (APCI, m / z): 440 (M + l) +

HPLC (reversed): Rt. (Min) = 3.72. Example 37: 3-Hydroxybenzaldehyde N- [4- {2-[(3-hydroxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 470 (M + l) +

HPLC (reversed): Rt. (Min) = 3.64. Example 38: 2-Hydroxybenzaldehyde N_ (4-anilino-6- {2 _ [(2-hydroxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

'H-NMR spectrum _{(270 MHz, DMSO- d 6)} ppm: 11.70 (s, 1H), 10.88 (s, 1H), 10.75 (s, 1H), 10.38 (s, 1H), 9.23 (s, 1H) , 8.40 (s, 1H), 8.31 (s, 1H),

7.80 (d, 2H, J = 8.1 Hz), 7.59 (d, 1H, J = 6.8 Hz), 7.20-7.39 (m, 5H), 6.90-6.95 (m, 5H), 6.02 (s, 1H)

MS (APCI, m / z): 440 (M + D +

HPLC (reversed): Rt. (Min) = 5.06. Example 39: 2-Hydroxybenzaldehyde N- [4- {2-[(2-hydroxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone 'H-NMR spectrum (270 _{MHz, DMSO- d 6) (5ppm} : 11.67 (s, 1H), 10.83 (s, 1H), 10.70 (s, 1H), 8.28-8.38 (m, 4H), 7.61 (d, 1H, J = 6.9 Hz ), 7.35 (d, 1 H, J = 7.6 Hz), 7.22 (t, 2H, J = 7.0 Hz), 6.89-7.01 (m, 8H), 6.21 (s, 1 H), 3.87 (s, 3H) MS (APCI, m / z): 470 (M + D +

 HPLC (reversed): Rt. (Min) = 4.88. Example 40: 4-Hydroxy-3-methylbenzaldehyde N- (4-anilino-6- {2-[(4-hydroxy-3-methylphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 468 (M + D +

 HPLC (reversed): Rt. (Min) = 3.97. Example 41: 4-Hydroxy-3N- [4- (2-[(4-hydroxy

-3-Methylphenyl) methylidene] hydr-6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

 MS (APCI, m / z): 498 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.98. Example 42: 4-Chloro-3-nitrobenzaldehyde N- (4-anilino-6- {2-[(4-chloro-3-nitrophenyl) methylidene] hydrazino} -2-pyrimidinyl) Hydrazone MS (APCI, m / z) 566 (M + D +

HPLC (reversed): Rt. (Min) = 4.85. Example 43: 4-chloro-3-nitrobenzaldehyde N- [4- {2-[(4-chloro-3-nitrophenyl) methylidene] hydrazino 6- (2-methoxyanilino) -2- Pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 596 (M + l) +

HPLC (reversed): Rt. (Min) = 5.02. Example 44: 3-Methoxybenzaldehyde N- (4-anilino-6- {2-[(3-methoxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 468 (M + D + HPLC (reversed): Rt. (Min) = 4.37. Example 45: 3-methoxybenzaldehyde N- (4- (2-methoxyanilino) -6- {2-[(3-methoxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone MS (APCI, m / z) : 498 (M + D +

 HPLC (reversed): Rt. (Min) = 4.38. Example 46: 3-Chlorobenzaldehyde N- (4-anilino-6- {2-[(3-chlorophthyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 476 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.78. Example 47: 3-Clo-benzaldehyde N- [4- {2-[(3-Clo-phenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 506 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.82. Example 48: 4-Ethylbenzaldehyde N- (4-anilino-6- {2-[(4-ethylphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

Ή-Awake R spectrum (270 MHz, DMS0-d ₆ ) dppm 10.75 (s, 1H), 10.55 (s, 1H), 9.14 (s, m), 8.10 (s, 1H), 8.06 (s, 1H), 7.90 (d, 2H, J-7.1 Hz), 7.59 (t, 4H, J = 7.6 Hz), 7.26-7.29 (m, 6H), 6.94 (t, 1H, J = 7.3 Hz), 6.11 (s, 1H), 2.64 (q, 4H, J-7.1 Hz), 1.21 (ί, 6H, J = 7.6 Hz)

MS (APCI, m / z): 464 (M + D +

HPLC (reversed): Rt. (Min) = 5.17. Example 49: 4-Ethylbenzaldehyde N- [4- {2-[(4-ethylphenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριη: 10.72 (s, 1H), 10.50 (s, 1H), 8.19 (s, 1H), 8.09 (s, 1H), 8.04 (s, 1H), 7.57-7.60 (m, 5H), 7.25-7.29 (m, 5H), 6.93-7.08 (m, 3H), 6.32 ( s, 1H), 2.63 (q, 4H, J = 7.5 Hz), 1.22 (t, 6H, J = 7.6 Hz)

MS (APCI, m / z): 494 (M + D +

HPLC (reversed): Rt. (Min) = 5.10. Example 50: 3-{[2- (4-anilino-6- {2-[(3-carpoxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazono] methyl} benzoic acid

MS (APCI, m / z): 496 (M + l) +

HPLC (reversed): Rt. (Min) = 3.65. Example 51: 2- [4-({2- [4-anilino-6- (2-{[4- (2-hydroxy-2-oxoethoxy) phenyl] methylidene} hydrazino) -2-pyrimidinyl] hydrazono} Methyl) phenoxy] acetic acid.

MS (APCI, m / z): 556 (M + l) +

 HPLC (reversed): Rt. (Rain) = 3.68. Example 52: 4-Hydroxy-3,5-dimethylbenzaldehyde N- (4-anilino-6- {2-[(4-hydroxy-3,5-dimethylphenyl) methylidene] hydrazino} -2-pyrimidinyl) Hydrazone

 MS (APCI, m / z): 496 (M + D +

 HPLC (reversed): Rt. (Min): 4.18. Example 53: 4-Hydroxy-3-methoxy-5-nitrobenzaldehyde N- (4-anilino-6- {2-[(4-hydroxy-3-methoxy-5-nitrophenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 590 (M + D +

HPLC (reversed): Rt. (Min) = 4.14. Example 54: 4-Methylbenzaldehyde N- (4-anilino-6- {2-[(4-methylphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 436 (M + D +

HPLC (reversed): Rt. (Min) = 4.79. Example 55: 5-Ethyl-2-furaldehyde N- (4-anilino-6- {2-[(5-ethyl-2-furyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 444 (M + l) +

HPLC (reversed): Rt. (Min) = 4.47. Example 56: 4- (Jethylamino) -2-HN- [4-anilino-6- (2-{[4- (Jethylamino) -2-hydroxyphenyl.

 ノ)-2-Pyrimidinyl] hydrazone

MS (APCI, m / z): 582 (M + D +

HPLC (reversed): Rt. (Min)-5.10. Example 57: 2-Hydroxoxy-5-nitrobenzaldehyde N- (4-anilino-6- {2-[(2-hydroxy-5-nitrophenyl) methylidene] hydrazino} -2-pyrimidinyl) hydride Razon

NMR-NMR spectrum (270 MHz, DMSO-d ₆ ) δρρπι: 11.16 (s, 1H), 11.00 (s, 1H), 9.35 (s, 1H), 8.58 (d, 1H, J = 2.8 Hz), 8.42- 8.50 (m, 3H), 8.12 (dd, 2H, J = 2.8 Hz, 9.1 Hz), 7.84 (d, 2H, J = 8.4 Hz), 7.33 (t, 2H, J = 7.7 Hz), 7.07-7.13 (in, 2H), 6.96 (t, 1H, J = 7.3 Hz), 6.13 (s, 1H)

MS (APCI, m / z): 530 (M + D +

HPLC (reversed): Rt. (Min) = 5.81.

MS (APCI, m / z): 516 (M + D + HPLC (reversed): Rt. (Min) = 4.83. Example 59: 2-chloro-6-N- (4-anilino-6- {2-[(2-cyclolip-6-fluorophenyl) methylidene] hi-2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 512 (M + l) +

HPLC (reversed): Rt. (Min) = 4.59. Example 60: 2-chloro-5-nitrobenzaldehyde N- (4-anilino-6- {2 _ [(2-chloro-5-nitrophenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone — rogue R Spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 11.38 (s, 1H), 11.27 (s, 1H),

9.43 (s, 1H), 8.79 (s, 1H), 8.69 (s, 1H), 8.57 (s, 1H), 8.53 (s, 1H), 8.16-8.19 (m, 2H), 7.92 (d, 2H, J = 8.2 Hz), 7.83 (dd, 2H, J = 3.0 Hz, 8.7 Hz), 7.35 (t, 2H, J = 7.7 Hz), 6.97 (t, 1H, J = 7.4 Hz), 6.23 (s, 1 H)

 MS (APCI, m / z): 566 (M + D +.

HPLC (reversed): Rt. (Min) = 5.24. Example 61: 5-Chloro-2--2-N- (4-anilino-6- {2-[(5-chloro-2-nitrophenyl) methylidene] hy 2-pyrimidinyl) hydrazone MS (APCI, m / z ): 566 (M + l) +

HPLC (reversed): Rt. (Min) = 5.37. Example 62 3,6 Trichloro

 MS (APCI, m / z): 612 (M + D +

HPLC (reversed): Rt. (Min) = 5.33 Example 63: 2-chloro-4- 4-fluorobenzaldehyde N- (4-anilino-6- {2--((2- Black mouth-4-Fluorophenylyl) methylidene] hydrazino}-'2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 512 (M + D +

 HPLC (reversed): Rt. (Min) = 4.92. Example 64: 2,3,5_Triclomouth benzaldehyde N- (4-anilino-6- {2-[(2,3,5-trichloromouthphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone MS (APCI, m / z): 612 (M + 1) +

HPLC (reversed): Rt. (Min) = 7.29. Example 65: 4-Fluoro-3- (trifluoromethyl) benzaldehyde N- [4-anilino-6- (2-{[4-fluoro-3- (trifluoromethyl) phenyl] methylidene} hydra Zino) -2-pyrimidinile] hydrazone

MS (APCI, m / z): 580 (M + D +

ゾン MS (APCI, m/z)： 566 (M+D + HPLC (reversed): Rt. (Min) = 5,08. Example 66 [(2-chloro-6-nitto

Zon MS (APCI, m / z): 566 (M + D +

HPLC (reversed): Rt. (Min) = 4.56 Example 67: 2-chloro-5- (trifluoromethyl) bed N-[4-anilino-6- (2--[[2-chloro Mouth-5- (Trifluoromethyl) hue hydrazino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 612 (M + 1) +

HPLC (reversed): Rt. (Min) = 6.07. Example 68: 2,2,5-mi N- (4-anilino-6- {2-[(2,5-difluoropheni-2-pyrimidinyl) hydrazone MS (APCI, m / z): 480 (M + l) +

HPLC (reversed): Rt. (Min) = 4.56. Example 69: 2,4-Difluoro mouth benzaldehyde N- (4-anilino-6- {2-[(2,4-difluorophenyl) methylidene] hydrazino 2-pyrimidinyl) hydrazone

MS (APCI, m / z): 480 (M + D +

HPLC (reversed): Rt. (Min) = 4.60. Example 70:

[(2,3,5,6-te

Hydrazone

 MS (APCI, m / z): 552 (M + l) +

HPLC (reversed): Rt. (Min) = 4.87 Example 71: 4-Fluoro-2- (trifluoromethyl) benzaldehyde N- [4-anilino-6- (2-{[4-fluoro-2 -(Trifluoromethyl) phenino

Dino)-2-pyrimidinyl] hydrazone

MS (APCI, m / z): 580 (M + l

HPLC (reversed): Rt. (Min) = 5.30. Example 72: 2,6-Difluoride N- (4-anilino-6- {2-[(2,6-difluorophenyl-2-pyrimidinyl) hydrazone

MS (APCI, m / z): 480 (M + D +

HPLC (reversed): Rt. (Min) = 4.39. Example 73: 3,5-Difluoro mouth benzaldehyde N- (4-anilino-6- {2-[(3,5-difluorophenyl) methylidene] hydrazino 2-pyrimidinyl) hydrazone

MS (APCI, m / z): 480 (M + D +

HPLC (reversed): Rt. (Rain) = 4.66. 'Example: .3--({2--[4--(2- [(3-Ripoxyfeni

 -(2-Methoxyanilino) -2-pyrimidinyl] h

 MS (APCI, m / z): 526 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.68. Example 75: 2- [4-({2- [2- (2-{[4- (2-hydroxy-2-oxoethoxy) phenyl] methylidene} hydrazino) -6- (2-methoxyanilino) -4-pyrimidinyl ] Hydrazono} methyl) phenoxy] acetic acid

 MS (APCI, m / z): 586 (M + D +

HPLC (reversed): Rt. (Min) = 3.67.

 2-Pyrimidinyl] hydrazone

 MS (APCI, m / z): 526 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.19 Example 77: 4-Hydroxy-3-methoxy-5-diN- [4- {2-[(4-hydroxy-3-methoxy-5-nitrophene: hydrazino } -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone

 MS (APCI, m / z): 620 (M + D +

 HPLC (reversed): Rt. (Rain) = 4.24. 'Example 78: 4N- (4- (2-methoxyanilino) -6- {2-[(4

-Methylphenyl) methylidene] hi-2-pyrimidinylyl) hydrazone

 MS (APCI, m / z): 466 (M + 1) +

HPLC (reversed): Rt. (Min): 5.04 Example 79: 5-Ethyl-2-furaldehyde N- [4- {2-[(5-ethyl-2-furyl) methylidene] hydrazino} -6_ (2-methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 474 (M + D +

HPLC (reversed): Rt. (Min) = 4.57. Example 80: 4- (Jethylamino) -2-hydroxybenzaldehyde N- [4- (2-{[4- (Jethylamino) -2-hydroxyphenyl] methylidene} hydrazino) -6- (2-methoxydiarino ) -2-Pyrimidinyl] hydrazone 2-trifluoroacetate

MS (APCI, m / z): 612 (M + 1) +

HPLC (reversed): Rt. (Min) = 5.30. Example 81: 2-hydroxy-5-hydroxybenzaldehyde N- [4- {2-[(2-hydroxy-5-nitrophenyl) methylidene] hydrazinoto 6_ (2-methoxyanilino) -2-pyrimidinyl] Hydrazone

MS (APCI, m / z): 560 (M + D +

HPLC (reversed): Rt. (Min) ii 5.63. Example 82: 2,3,4-Trifluorobenzaldehyde N- (4_ (2-methoxyanilino) -6- {2-[(2,3,4-trifluorophenyl) methylidene] hydrazino 2-pyrimidinyl) Hydrazone

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) 5 pm: 11.11 (s, 1H), 10.95 (s, 1H), 8.53 (brs, 1H), 8.31 (s, 1H), 8.26 (s, 1H) , 8.20 (s, 1H), 7.71-7.76 (m, 2H), 7.41-7.52 (m, 2H), 6.93-7.05 (m, 3H), 6.39 (s, 1H), 3.87 (s, 3H) MS ( APCI, m / z): 546 (M + l) +

HPLC (reversed): Rt. (Min) = 4.87. Example 83: 2-chloro-6-fluorobenzaldehyde N— [4- {2 -— ((2-chloro-6-fluorophenyl) methylidene] hydrazino} -6- (2-methoxyanilino)- 2-Pyrimidinyl] hydrazone MS (APCI, m / z): 542 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.65. Example 84: 2-chloro-5-nitrobenzaldehyde N- [4- {2-[(2-chloro-5-nitrophenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2 -Pyrimidinyl] hydrazone

 MS (APCI, m / z): 596 (M + l) +

 HPLC (reversed): Rt. (Min) = 5.17. Example 85: 5-chloro-2-N-nitrobenzaldehyde N- [4- {2-[(5-chloro-2-nitrophenyl) methylidene] hydrazino 6- (2-methoxyanilino) -2- Pyrimidinyl] hydrazone

 MS (APCI, m / z): 596 (M + l) +

 HPLC (reversed): Rt. (Min) = 5.41. Example 86: 2,3,6-Trichlorobenzaldehyde N- (4- (2-methoxyanilino) -6- {2-[(2,3,6-trichloromethylphenyl) methylidene] hydrazino} -2-pyrimidinyl ) Hydrazone

 MS (APCI, m / z): 642 (M + l) +

HPLC (reversed): Rt. (Min) = 5.58. Example 87: 2-chloro-4-fluorobenzaldehyde N- [4- {2-[(2-chloro-4-fluorophenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2- Pyrimidinyl] hydrazone

MS (APCI, m / z): 542 (M + l) +

HPLC (reversed): Rt. (Min) = 5.04. Example 88: 2,3,5-Triclomethylbenzaldehyde N- (4- (2-methoxyanilino) -6- {2-[(2,3,5-trichloromethylphenyl) methylidene] hydrazino} -2- Pyrimidinyl) Hydrazone

 MS (APCI, m / z): 642 (M + l) +

 HPLC (reversed): Rt. (Min) = 7.34. Example 89: 4-fluoro-3- (trifluoromethyl) benzaldehyde- [4- (2-[[4-fluoro-3- (trifluoromethyl) phenyl] methylidene} hydrazino) _6- (2-methoxyanilino) ) -2-Pyrimidinyl] hydrazone

MS (APCI, m / z): 610 (M + l) +

HPLC (reversed): Rt. (Min) = 5.16. Example 90: 2-chloro-6-nitrobenzaldehyde N- [4- {2-[(2-chloro-6-nitrophenyl) methylidene] hydrazino 6- (2-methoxyanilino) -2- Pirimigel] hydrazone

 MS (APCI, m / z): 596 (M + l) +.

HPLC (reversed): Rt. (Min): 4.56. Example 91: 2-Chloro - 5- (triflate Ruo b-methyl) benzaldehyde - [4- (2 - {[2 one black hole - ₅ one (Torifuruo port methyl) phenyl] methylidene} hydrazino) - ₆ - ₍₂ - Methoxyilino) -2-pyrimidinyl] hydrazone

- NMR spectrum _{(270 MHz, DMS0 - d 6} ) δ ριη: 11.22 (s, 1H), 11.14 (s, 1H), 8.22-8.54 n, 6H), 7.74-7.75 (m, 4H), 6.89-7.05 ( m, 3H), 6.36 (s, 1H), 3.86 (s, 3H)

 MS (APCI, m / z): 642 (M + l) +

 HPLC (reversed): Rt. (Min) = 6.00. Example 92: 2,5-difluorobenzaldehyde- [4- {2-[(2,5-difluorophenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

'H-NMR spectrum _{(270 MHz, DMSO- d 6)} ^ pm: 11.08 (s, 1H), 10.99 (s, 1H), 8.69 (brs, 1H), 8.36 (s, 1H), 8.28 (s, 1H), 8.23 (s, 1H), 7.65-7.74 (m, 2H), 7.21-7.39 (m, 4H), 6.91-7.06 ( m, 3H), 6.50 (s, 1H), 3.89 (s, 3H)

MS (APCI, m / z): 510 (M + D +

 HPLC (reversed): Rt. (Min) = 4.68. Example 93: 2,4-difluorobenzaldehyde N- [4- {2-[(2,4-difluorophenyl) methylidene] hydrazino 6- (2-methoxyanilino) -2_pyrimigel] hydrazone

-NMR spectrum _{(270 MHz, DMSO- d 6)} 6 ppm: 11.00 (s, 1H), 10.82 (s, 1H), 8.28 (s, 1H), 8.26 (s, 1H), 8.22 (s, 1H), 7.92-8.03 (m, 2H), 7.18-7.38 (m, 5H), 6.95-7.05 (m, 3H), 6.38 (s, 1H), 3.87 (s, 3H)

 MS (APCI, m / z): 510 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.63. Example 94: 2,3,5,6-Tetrafluoromethylbenzaldehyde N- (4- (2-methoxyanilino) _6- {2-[(2,3,5,6-tetrafluoromethylphenyl) methylidene] hydrazino } -2 -Pyrimidinyl) hydrazone

Ή-image R spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 11.19 (s, 1H), 11.07 (s, 1H), 8.46 (s, 2H), 8.24 (s, 1H), 8.19 (s, 1H) ), 7.83-7.89 (m, 2H), 6.87-7.02 (m, 3H), 6.28 (s, .1H), 3.85 (s, 3H)

MS (APCI, m / z): 582 (M + l) +

HPLC (reversed): Rt. (Min) = 4.91. Example 95: 4-Fluoro-2- (trifluoromethyl) benzaldehyde- [4- (2-{[4-fluoromethyl-2- (trifluoromethyl) phenyl] methylidene} hydrazino) -6- (2 -Methoxyanilino)-2-pyrimidinyl] hydrazone

Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) (5 pm: 11.21 (s, 1H), 11.07 (s, 1H), 8.26-8.42 (m, 6H), 7.67 (m, 4H), 6.97-7.03 (m, 3H), 6.44 (s, 1H), 3.88 (s, 3H) MS (APCI, m / z): 610 (+ l) +

 HPLC (reversed): Rt. (Min) = 5.39. Example 96: 2,6-Difluorobenzaldehyde N- [4- {2-[(2,6-difluorophenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

Ή - NMR spectrum _{(270 MHz, DMS0 - d 6} ) <5ppm: 11.00 (s, 1H), 10.79 (s, 1H), 8.20-8.28 (HI, 3H), 7.40-7.45 (m, 2H), 7.14- 7.27 (m, 5H), 6.93-7.05 (m, 3H), 6.19 (s, 1H), 3.85 (s, 3H)

 MS (APCI, m / z): 510 (M + D +

 HPLC (reversed): Rt. (Min) = 4.43. Example 97: 3,5-Difluoro mouth benzaldehyde N- [4- {2-[(3,5-difluorophenyl) methylidene] hydrazino 6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

丽R spectrum _{(270 MHz, DMSO- d 6)} (5ppm: 11.04 (s, 1H), 10.94 (s, 1H), 8.36 (s, m), 8.10 (s, 1H), 8.05 (s, 1H), 7.41 (m, 5H), 7.23 (in, 2H), 6.96-7.05 (m, 3H), 6.49 (s, 1H), 3.90 (s, 3H) MS (APCI, m / z): 510 (M + l HPLC (reversed): Rt. (Min) = 4.71 Example 98: 4-Methyl-1Η-imidazole-5-carpaldehyde N- (4_anilino-6- {2-[(4-methyl-1H -Imidazole-5-yl) methylidene] hydrazino 2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 416 (M + lH

HPLC (reversed): Rt. (Min) = 3.81. Example 99: 4-methyl-1H-imidazole-5-carpaldehyde N- (4- (2-methoxyanilino) -6- {2-[(4-methyl-1H-imidazole-5-yl) methylidene] Hydrazino} -2-pyrimidinyl) hydrazone 2 trifluoroacetic acid MS (APCI, m / z): 446 (Mil) I

 HPLC (reversed): Rt. (Min) = 3.84. Example 100: 1,3-Benzodioxol-4-force lipaldehyde N- (4-anilino-6- {2- [1,3_benzodioxol-4-ylmethylidene] hydrazino} -2-pyrimidinyl) Hydrazone trifluoroacetate

MS (APCI, m / z): 496 (M + D +

HPLC (reversed): Rt. (Min) = 4.34. Example 101: 1,3-benzodioxole-4-carpaldehyde-[4- {2- [1,3-benzodioxol-4-ylmethylidene] hydrazino} -6- (2-methoxyanilino) -2- Pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 526 (M + l

HPLC (reversed): Rt. (Min) = 4.43. Example 102: 3- (tert-butyl)

6- (2- {[3- (ter t-butyl) -2-

Limidinyl] hydrazone

MS (APCI, m / z): 552 (M + lH

HPLC (reversed): Rt. (Min) = 8.32.

Nirino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 582 (M + D +

HPLC (reversed): Rt. (Min) = 8.19. Example 104: 5-Methoxy-1-N- {4-anilino-6- [2- (5-methoxy-2,3-dihydro-1H-indene-1--1--2-pyrimidinyl} hydrazone MS (APCI, m / z): 520 (M + l

 HPLC (reversed): Rt. (Min) = 4.99. Example 105: 5-Fluoro-1-indanone N- -anilino-6- [2- (5-fluoro-2,3-dihydro-1H-indene-1-ylidene) hydrazino] -2-pyrimidinyl} hydrazone MS ( APCI, m / z): 496 (M + lH

HPLC (reversed): Rt. (Min) = 4.89. Example 106: 5-Chlorobutanodanone N- -anilino-6- [2- (5-chloro-2,3-dihydrido-1H-indene-toylidene) hydrazino] -2-pyrimidinyl} hydrazone

MS (APCI, m / z): 528 (M + l) +

HPLC (reversed): Rt. (Min) = 5.76. Example 107: 6-methoxy-1-indanone N_ {4-anilino-6- [2- (6-methoxy-2,3-dihydro-1H-indene-triylidene) hydrazino] -2-pyrimidinyl} hydrazone trifluoroacetic acid salt

MS (APCI, m / z): 520 (M + D +

HPLC (reversed): Rt. (Min) = 4.78. Example 108: 3-chloro-4-fluorobenzaldehyde N- (6-anilino-2- {2-[(3-chloro-4-fluorophenyl) methylidene] hydrazino-4-hydrimidinyl) hydra

MS (APCI, m / z): 512 (M + D +

 HPLC (reversed): Rt. (Min) = 4.91. Example 109: 2-Fluoro-3- (trifluoromethyl) benzaldehyde N- [6-anilino-2- (2-{[2-fluoro-3- (trifluoromethyl) phenyl] methylidene}} Hydra-zino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 580 (M + l) + HPLC (reversed): Rt. (Min) = 5.23. Example 110: 2,3-Difluorobenzaldehyde N- (6-anilino-2- {2-[(2,3-difluorophenyl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 480 (M + D +

HPLC (reversed): Rt. (Min) = 4.58. Example 111: 2-Fluoro-6- (trifluoromethyl) benzaldehyde N- [6-anilino-2- (2-{[2-fluoro-6- (trifluoromethyl) phenyl] methylidene} hydridino} hydrazino -4-Pyrimidinyl] hydrazone

MS (APCI, m / z): 580 (M + l) +

HPLC (reversed): Rt. (Min) = 4.74. Example 112: 4-Chloro-2-N- (6-anilino-2- {2-[(4-chloro-2-fluorophenyl) methylidene] hi-4-pyrimidinyl) hydrazone

 MS (APCI, m / z): 512 (M + l) +

 HPLC (reversed): Rt. (Min) = 5.11. Example 113: 4-chloro-3-N- (6-anilino-2- {2-[(4-chloro-3-fluorophenyl) methylidene] hy-4-pyrimidinyl) hydra

MS (APCI, m / z): 512 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.93. Example 114: 2-Fluoro_5-nitrobenzaldehyde N- (6-anilino-2- {2-[(2-fluoro-5-ditrophenyl) methylidene] hydrazino} -4-pyrimidinyl) hydra

MS (APCI, m / z): 534 (M + l) + W

102

HPLC (reversed): Rt. (Min) = 4.64. Example 115: 2-hydroxy-3-methoxy-5-di-N- (4-anilino-6- {2-[(2-hydroxy-3-methoxy-5-nitrophenihydrazino) -2-pyrimigel] ) Hydrazone trifluoroacetate

MS (APCI, m / z): 590 (M + D +

HPLC (reversed): Rt. (Min) = 5.36. Example 116: 4-chloro-2-nitrobenzaldehyde N— (4-anilino-6- {2 -— ((4-chloro-2-2-nitrophenyl) methylidene] hy-2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 566 (M + l) +

HPLC (reversed): Rt. (Min) = 5.25 Example 117: 5-{[2- (4-anilino-6- {2-[(5-carboxy-2-furyl) methylidene] hydrazino} -2-pyrimidinyl} ) Hydrazono] methyl} -2-fruit acid MS (APCI, m / z): 476 (M + 1) +

HPLC (reversed): Rt. (Rain) = 3.30

ノ }- 2-ピリミジニル） ヒドラゾン N- (4-anilino-6- {2- [

ノ}-2-Pyrimidinyl) hydrazone

 MS (APCI, m / z): 504 (M + l) +

ジノ }-2-ピリミジニ ル）ヒドラゾン HPLC (reversed): Rt. (Min) = 4.59 Example 119: 3-Ethoxy-2-HN- (4-anilino-6- {2-[(3-ethoxy-2-hydroxyphenyl)

Zino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 528 (+ l) + HPLC (reversed): Rt. (Min) = 5.07 Example 120: 5-Crosin-triindanenone N- [4- [2- [5-Crosin-2,3-dihydro-1H-indene- Trilidene) hydrazino] -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

 MS (APCI, m / z): 558 (Mll) +

 HPLC (reversed): Rt. (Min) = 5.60. Example 121: Methyl 3-({2- [4-anilino-6- (2-{[3- (methoxycarbonyl) phenol)

 MS (APCI, m / z): 524 (Mll) +

HPLC (reversed): Rt. (Min) = 4.46 Example 122: 6-Methyl-1-indanone N- {4- (2-methoxyanilino) -6- [2- (6-methyl-2,3 -Dihydrid-1H-indene-1-ylidene) hydrazino] -2-pyrimidinyl} hydrazone

 MS (APCI, m / z): 518 (M + D +

HPLC (reversed): Rt. (Min) = 5.36 Example 123: Methyl 3-({2- [4- (2-methoxyanilino) -6- (2-{[3- (methoxycarbonyl) phenyl] methylidene) } Hydrazino) -2-pyrimidinyl] hydrazono} Methyl) benzoate trifluoroacetate.

MS (APCI, m / z): 554 (M + l) +

HPLC (reversed): Rt. (Min) = 4.48 Example 124: 8-Hydroxy-2-quinolinecarbaldehyde N- (4-anilino-6- {2-([8-hydroxy-2-quinolinyl) methylidene) ] Hydrazino-2-pyrimidinyl) hydrazone trifluoroacetate MS (APCI, m / z): 542 (M + l) +

HPLC (reversed): Rt. (Min) = 4.55 Example 125: 8-Hydroxy-2-quinolinecarpaldehyde N- [4- {2-[(8-hydroxy-2-quinolinyl) methylidene] hydrazino} -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 572 (M + D +

HPLC (reversed): Rt. (Min) = 4.62. Example 126: 3_clo mouth-4-fluorobenzaldehyde N- [2- {2 _ [(3-cloopen-4-fluorophenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -4-pyrimi Zinyl] hydrazone

MS (APCI, m / z): 542 (M + D +

HPLC (reversed): Rt. (Min) = 4.98

-Methoxyanilino) -4-Pyrimidinyl] hydrazone

MS (APCI, m / z): 610 (M + 1) +

HPLC (reversed): Rt. (Min) = 5.29 Example 128: 2,3-Difluorobenzaldehyde [2- {2-[(2,3-difluorophenyl) methylidene] hydrazino} -6- (2 -Methoxyanilino)-4-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 510 (M + l

HPLC (reversed): Rt. (Min) = 4.76 Example 129: 2-fluoro-6- (trifluoro

{[2-Fluoro-6- (trifluoromethyl) -Methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 610 (M + D +

HPLC (reversed): Rt. (Min) = 4.77 Example 130: 4-chloro-2-fluorobenzaldehyde N- [2- {2-[(4-chloro-2-fluorophenyl) methylidene] Hydrazino} -6- (2-Methoxyanilino) -4-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 542 (M + l

HPLC (reversed): Rt. (Min) = 5.24. Example 131: 4-Chloro-3-de N- [2- {2-[(4-chloro-3-fluorophenyl) methylidene] hi-6- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 542 (M + l) +

HPLC (reversed): Rt. (Min) = 4.95 Example 132: 5-nitro-3-thiophenecarbaldehyde N- (4-anilino-6- {2-([5-trito-3 phenyl) ) Methylidene] hydrazino} -2-pyrimidinyl) hydrazone MS (APCI, m / z): 510 (M + lH

HPLC (reversed): Rt. (Min) = 4.27 Example 133: 2-Fluoro-5-nitrobenzaldehyde N- [2- {2-[(2-fluoro-5-nitrophenyl) methylidene] hydrazino} -6- (2-methoxyanilino)-4-pyrimidinyl] hydrazone trifluoacetate

MS (APCI, m / z): 564 (M + lH

HPLC (reversed): Rt. (Min) = 4.66 Example 134: 2-hydroxy-3-methoxy-5-nitrobenzaldehyde N- [4- {2-[(2-hydroxy-3-methoxy- 5-nitrophenyl) methylidene] hydrazino} -6- (2- Methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate MS (APCI, m / z): 620 (M + l) +

HPLC (reversed): Rt. (Min) = 5.22 Example 135: 2-Chloro-3-quinolinecarpaldehyde N- [4-{2-[(2-chloro-3-quinolinyl) methylidene] hydrazino 6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone 2 trifluoroacetate

MS (APCI, m / z): 608 (M + D +

HPLC (reversed): Rt. (Min) = 5.20. Example 136: 4-chloro-2-nitrobenzaldehyde N- [4- {2-[(4-chloro-2-nitrophenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2 -Pyrimidinyl] hydrazone

 MS (APCI, m / z): 596 (M + l) +

HPLC (reversed): Rt. (Min) = 5.27 Example 137: 5-({2- [4- {2-[(5-carboxy-2-fuhydrazino)}-6_ (2-methoxyanilino) -2-pyrimidinyl ] H-2-Floic Acid

 MS (APCI, ra / z): 506 (M + l

HPLC (reversed): Rt. (Min) = 3.28 Example 138: 2-Fluoro-4-Methyl N_ [4- {2-[(2-fluoro-4-methoxyphenyl) methylidene] hi-6- ( 2-Methoxyanilino)-2-Pyrimidinyl] hydrazone

 MS (APCI, m / z): 534 (M + D +

HPLC (reversed): Rt. (Min) = 4.66 Example 139: 3-ethoxy-2-hide N- [4- {2-[(3-ethoxy 2-hydroxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 558 (M + D +

HPLC (reversed): Rt. (Min) = 4.90 Example 140: 5-Nitro-3-thiophencarpaldehyde N- (4- (2-methoxyanilino) -6- {2 _ [(5-dito Mouth-3-Chenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 540 (M + D +

HPLC (reversed): Rt. (Min) = 4.34. Example 141: 5-{[2- (4-anilino-6-caproloxy-2-phenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazono] methyl} -2-thiophenecarboxylic acid MS (APCI, m / z): 508 (M + l) +

HPLC (reversed): Rt. (Min) = 3.52 Example 142: 5-({2- [4- {2-[(5-hexyloxy-2-phenyl) methylidene] hydrazino} -6- ( 2-methoxyanilino) -2-pyrimidinyl] hydrazono} methyle) -2-thiophene

MS (APCI, m / z): 538 (M + D +

ラジノ } -2 -ピリミ ジニリレ）ヒドラゾン HPLC (reversed): Rt. (Min) = 3.48 Example 143: 3,5-dichloro-2- 2-N- (4-anilino-6- {2-[(3,5-dichloro-2-hydroxy)

Radino} -2 -Pirimi ginirile) hydrazone

MS (APCI, m / z): 576 (M + l) +

HPLC (reversed): Rt. (Min) = 8.42 Example 144: 2-Fluoro-4- (trifluoromethyl) benzaldehyde N- [4- (2- {[2-Fluoro-4- (trifluoromethyl) phenino '-6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 610 (M + D +

HPLC (reversed): Rt. (Min) = 6.02 Example 145: 2-Fluoro-5- (trifluoromethyl) benzaldehyde N- [4-anilino-6- (2-{[2-fluoro Mouth-5- (trifluoromethyl) phenyl] methylidene} hydrazino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 580 (M + 1) +

HPLC (reversed): Rt. (Min) = 5.31.

{

-Methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 610 (M + D +

ジノ } _2-ピリミジニ ル）ヒドラゾン HPLC (reversed): Rt. (Min) = 5.33 Example 147: N- (4-anilino-6- {2-[(2-hydroxy

Zino} _2-Pyrimidinyl) hydrazone

 MS (APCI, m / z): 500 (M + l) +

HPLC (reversed): Rt. (Min) = 4.75 Example 148: 2-hydroxy-4-methylaldehyde N- [4_ {2-[(2-hydroxy-4-methoxyphenyl) methylidene] hydrazino} -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 530 (M + l

HPLC (reversed): Rt. (Min) = 4.67 Example 149: 4-Hydroxy-2-methoxybenzaldehyde N- (4-anilino-6- {2-[(4-hydroxy-2-methoxyphenyl) methylidene] hydrazino} -2-pyrimidyl) hydrazone trifluoroacetate

MS (APCI, m / z): 500 (M + D +

HPLC (reversed): Rt. (Min) = 3.97 Example 150: 4-Hydroxy-2-methoxybenzaldehyde N- [4- {2-[(4-hydroxy-2-methoxyphenyl) methylidene] hydrazino } -6- (2-Methoxyanilino)-2-pyrimigel] hydrazone

MS (APCI, m / z): 530 (M + D +

 HPLC (reversed): Rt. (Min) = 3.98. Example 151: Benzaldehyde aldehyde N- (4-anilino-6- {2- [phenylmethylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 408 (M + l

 HPLC (reversed): Rt. (Min) = 4.37 Example 152: Benzaldehyde N- (4- (2-methoxyanilino) -6- {2- [phenylmethylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 438 (M + l) +

 HPLC (reversed): Rt. (Rain) = 4.44 Example 153: 1H-indole-3-carbaldehyde N- (4-anilino-6- {2- [1H-indole-3-ylmethylidene] hydrazino} 2-Pyrimidinyl) hydrazone trifluoroacetate

 MS (APCI, m / z): 486 (M + D +

HPLC (reversed): Rt. (Min) = 4.22 Example 154: 1H-indole-3-carboxaldehyde N- [4- {2- [1H-indole-3- -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 516 (M + l

HPLC (reversed): Rt. Din) = 4.20 Example 155: 4-M-N- (4-anilino_6- {2-[(4-methoxyphen: 2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 468 (M + D +

 HPLC (reversed): Rt. (Min) = 4.43. Example 156: 4-Methoxybenzaldehyde N- (4- (2-methoxyanilino) -6- {2-[(4-methoxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone MS (APCI, m / z) : 498 (M + lH

HPLC (reversed): Rt. (Min) = 4.49 Example 157: 4-{[2- (4-anilino_6-{2-[(4_cyanophenyl) methylidene] hydrazino} -2-pyrimidinyl) hydran "Nito U

MS (APCI, m / z): 458 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.0 Example 158: 4-({2-[4- {2_ [(4_ shear)

-Methoxyanilino) -2-pyrimidinyl]

MS (APCI, m / z): 488 (M + l) +

HPLC (reversed): Rt. (Min) = 4.26 Example 159: N- (4-anilino-6- {2- [cyclo

 -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 420 (M + l) +

HPLC (reversed): Rt. (Min) = 5.14 Example 160: Cyclohexane power lipaldehyde N- [4- {2- [cyclohexylmethylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone MS (APCI, m / z): 450 (M + 1) +-HPLC (reversed): Rt. (Min) = 5.16. Example 161: 3,5-Dichro-2--2-N- [4- {2-[(3,5-dichloro-2-Hydroxyphenyhydrazino) -6- (2-methoxyanilino) -2] -Pyrimidinyl] hydrazone

MS (APCI, m / z): 606 (M + l) +

HPLC (reversed): Rt. (Min) = 8.31 Example 162: Methyl 4-({2- [4-anilino-6- (2-{[4- (methoxycarbonyl) feto trifluoroacetate]

 MS (APCI, m / z): 524 (M + D +

HPLC (reversed): Rt. (Min) = 4.47 Example 163: 5-Methyl-2-furaldehyde N- (4-anilino-6_ {2-[(5-methyl-2-furyl) methylidene] hydrazino 2-pyrimidinyl) hydrazone

MS (APCI, m / z): 416 (M + D +

HPLC (reversed): Rt. (Min) = 4.18 Example 164: 5-methyl-2-furaldehyde N- (4- (2-methoxyanilino) -6- {2-([5-methyl-2- Furyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone MS (APCI, m / z): 446 (M + D +

HPLC (reversed): Rt. (Min) = 4.19 Example 165: 3-ethoxy-4-H-N- (4-anilino-6- {2 -[(3-Ethoxy-4-hydroxyphenyl) methylidene] hydrazino} -2-pyrimidinylyl) hydrazone

 MS (APCI, m / z): 528 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.02. Example 166: 3_ethoxy-4-N- [4- {2-[(3-ethoxy-4-hydroxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 558 (M + D +

HPLC (reversed): Rt. (Min) = 3.99 Example 167: 3-methylbenzaldehyde N- (4-anilino-6- {2-[(3-methylphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 436 (M + l) +

HPLC (reversed): Rt. (Min) = 4.80 Example 168: 3 N- (4- (2-Methoxyphenyl)-{2 _ [(3-methylphenyl) methylidene] hy-2-pyrimidinyl) hydrazone trifluorfluoroacetate

 MS (APCI, m / z): 466 (M + l) +

HPLC (reversed): Rt. (Min) = 4.94 Example 169: 3-{[2- (4-anilino-6- {2-[(3-cyanophenyl) methylidene] hydrazino 2_pyrimidinyl) hydrazono] methyl } Benzonitrile

MS (APCI, m / z): 458 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.20 Example 170: 3-({2- [4- [2-[(3-cyanophen :: l) methylidene] hydrazino}-6- (2-methoxyanilino)- [2-pyrimidinyl] hydryl MS (APCI, m / z): 488 (M + D +

HPLC (reversed): Rt. (Min) = 4.23. Example 171: Methyl 4-({2- [4- (2-methoxyanilino) -6- (2-{[4- (methoxycarbonyl) phenyl] methylidene} hydrazino) -2-pyrimidinyl] hydrazono} methyl) benzoe 1-Trifluoroacetate

MS (APCI, m / z): 554 (M + l) +

HPLC (reversed): Rt. (Min) = 4.46 Example 172: 4-butoxybenzaldehyde N- (4-anilino-6- {2 _ [(4-bu, toxylphenyl) methylidene] hydrazino} -2-pyrimidinyl} ) Hydrazone

MS (APCI, m / z): 552 (M + l) +

HPLC (reversed): Rt. (Min) = 6.14 Examples 1-3: 4-butoxybenzaldehyde N- [4- {2-[(4_butoxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino ) -2-Pyrimidinyl] hydrazone MS (APCI, m / z): 582 (Mll) +

HPLC (reversed): Rt. (Min) = 6.10 Example 174: 4-N- (4-anilino-6- {2-[(4-isopropylpropylphenyl) methylidene] hi-2-pyrimidinyl) hydrazone MS (APCI, m / z): 492 (M + D +

HPLC (reversed): Rt. (Min) = 5.57 Example 175: 4-isopropylbenzaldehyde-[4- {2-[(4-isopropylphenyl) methylidene] hydrazino} -6- (2-methoxyanilino) )-2-Pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 522 (M + l) +

HPLC (reversed): Rt. (Min) = 5.84. Example 176: dihydro-3 (2H) -thiophenone N- {6-anilino-2- [2-dihydro-3 (2H) -thiophenylidenehydrazino] -4-pyrimidinyl} hydrazone

 MS (APCI, m / z): 400 (M + D +

ラゾ ン トリフルォロ酢酸塩 HPLC (reversed): Rt. (Min) = 3.90 Example [(2,4,5-tri

Razon trifluoroacetate

 MS (APCI, m / z): 588 (M + D +

 HPLC (reversed): Rt. (Min) = 4.31 Example 178: 2,4,5-trimethoxybenzaldehyde N- (4- (2-methoxyanilino) -6- {2-[(2,4,4 5-trimethoxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetate

 MS (APCI, m / z): 618 (M + D +

 HPLC (reversed): Rt. (Min) = 4.31

ジノ }- 2-ピリミジェ ル）ヒドラゾン トリフルォロ酢酸塩 N- (4_anilino-6-{2

Dino}-2-pyrimidyl) hydrazone trifluoroacetate

 MS (APCI, m / z): 556 (M + l

 HPLC (reversed): Rt. (Min) = 5.24 Example 180: 2,4-Dimethoxy-3- "N— [4_ {2-[(2,4-Dimethoxy-3-methylphen-2-6) -(2-Methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate

, MS (APCI, m / z): 586 (M + D +

HPLC (reversed): Rt. (Min) = 5.27. Example 181: 4-Methoxy-2,5-dimethylbenzaldehyde N- (4-anilino-6- {2-[(4-methoxy-2,5-dimethylphenyl) methylidene] hydrazino} -2-pyrimidyl) Hydrazone trifluoroacetate

MS (APCI, m / z): 524 (M + D +

 HPLC (reversed): Rt. (Min) = 5.22 Example 182: 4-Methoxy-2,5-dimethylpenzaldehyde N- (4- (2-methoxyquinolinyl) -6- {2-[(4 -Methoxy-2,5-dimethylphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 554 (M + 1) +

HPLC (reversed): Rt. (Min) = 5.21 Example 183: 2-methoxy-1-naphthaldehyde N- (4-anilino-6- {2-[(2-methoxy-1-naphthyl) methylidene] hydrazino }-2-Pyrimidinyl) hydrazone

MS (APCI, m / z): 568 (M + D +

HPLC (reversed): Rt. (Min) = 5.01 Example 184: 2-Methoxy-1-naphthaldehyde N_ [4- {2-[(2-methoxy-1-naphthyl) methylidene] hydrazino} -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 598 (M + 1) +

HPLC (reversed): Rt. (Min) = 5.26 Example 185: 4-ethoxy-3-methoxybenzaldehyde N- (4-anilino-6- {2-[(4-ethoxy-3-methoxyphenyl) methylidene] Hydrazino 2-pyrimidinyl) hydrazone

H-NMR spectrum _{(270 MHz, DMSO- d 6)} δ ριη: 10.64 (s, 1H), 9.84 (s, lh), 9.08 (s, lh), 8.07 (s, 1H), 8.00 (s, 1H) , 7.83 (d, 2H, J = 8.1 Hz), 7. W

116

54 (d, 1H, J = 8.2 Hz), 7.38 (s, 1H), 7.24-7.29 (m, 3H), 7.11-7.17 (m,

2H), 6.93-7.02 (m, 2H), 6.08 (s, 1H), 4.01-4.18 (m, 4H), 3.83 (s, 6H),

1.32-1.39 (m, 6H)

 MS (APCI, m / z): 556 (M + l) +

 HPLC (reversed): Ri. (Min) = 4.37. Example 186: 4-Ethoxy-3-meth N- [4- {2-[(4-ethoxy-3-methoxypheno 6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 586 (M + l) +

HPLC (reversed): Rt. (Min) = 4.41 Example 187: 4,5-dimethyl-2-furaldehyde ^ (4-anilino-6- {2-[(4,5_dimethyl-2-furyl) Methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 444 (M + l) +

HPLC (reversed): Rt. (Min) = 4.51 Example 188: 4,5-Dimethyl-2-furaldehyde N- [4- {2-[(4,5-dimethyl-2-furyl) methylidene] hydrazino 6- (2-Methoxyanilino) -2-pyrimidinyl] hydra

MS (APCI, m / z): 474 (M + l) +

HPLC (reversed): Rt. (Min) = 4.55 Example 189: 2,4,6-trime N- (4-anilino-6- {2-[(2,4,6-trimethoxyphenyl)] [Methylidene] hydrazinoto • 2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 588 (M + l) +

HPLC (reversed): Rt. (Min) = 4.48 W

117 Example 190: 3-Hydroxy-4,5-dimethoxybenzaldehyde N- (4-anilino-6- {2 _ [(3-hydroxy-4,5-dimethoxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) Hydrazone

MS (APCI, m / z): 560 (Mil) +

ラゾン MS (APCI, m/z): 472 (M+l HPLC (reversed): Rt. (Min) = 3.73. Example 191 {2-[(3,5-dihydroxy

Razon MS (APCI, m / z): 472 (M + l

HPLC (reversed): Rt. (Min) 3.35 Example 192: 2,5-Dimethylbenzaldehyde N- (4-anilino-6- {2-[(2,5-dimethylphenylenediyl) methylidene] hydrazino} -2 -Pyrimidinyl) hydrazone

MS (APCI, m / z): 464 (M + D +

HPLC (reversed): Rt. (Min) = 4.89 Example 193: 2-hydroxy-5-methaldehyde N- (4_anilino-6- {2-[(2-hydroxy-5-methoxyphenyl hydrazino} -2] _Pirimigel) Hydrazone

 MS (APCI, m / z): 500 (M + l) +

HPLC (reversed): Rt. (Min) = 4.87 Example 194: 4-Methoxy-1-naphthaldehyde N- (4-anilino-6- {2-[(4-methoxy-1-naphthyryl) methylidene] Hydrazino} -2-pyrimidini) hydrazone

MS (APCI, m / z): 568 (M + D +

HPLC (reversed): Rt. (Rain) = 5.26 Example 195: 2,6-Dimethyl N- (4-anilino-6- {2-[(2,6-dimethoxyphene: --2-pyrimidinino) MS (APCI, m / z): 528 (Μ + 1) +

 HPLC (reversed): Rt. (Min) = 4.41. Example 196: 2-hydroxy-5-miN- (4-anilino-6- {2-[(2-hydroxy-5-methylphenyl) methylidene] hi-2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 468 (M + l) +

HPLC (reversed): Rt. (Min) = 5.58 Example 197: 2-hydroxy-3-methylbenzaldehyde N- (4-anilino-6- {2-

[(2-Hydroxy-3-methylphenino-2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 468 (M + l) +

ヒドラゾン MS (APCI, m/z)： 520 (M+1) + HPLC (reversed): Rt. (Rain) = 6.77 Example 198 no_6- (2-{[4- (te rt-butyl) phenyl)

Hydrazone MS (APCI, m / z): 520 (M + 1) +

HPLC (reversed): Rt. (Min) 5.86 Example 199: 3-ethoxy-4-me N- (4-anilino-6— {2-

[(3-ethoxy-4-methoxyphenyl) methylidene] hydrazino 2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 556 (M + l) +

HPLC (reversed): Rt. (Min) = 4.28

ジノ } - 2 -ピリミジニ レ）ヒドラゾン MS (APCI, m/z)： 524(M+1) + N- (4-anilino-6- {2

Zino}-2-pyrimidini) hydrazone MS (APCI, m / z): 524 (M + 1) +

 HPLC (reversed): Rt. (Rain) = 5.18. Example 201: 3-Me ;, N— (4-anilino-6- {2-[(3-methoxyphenyl) methi i 2 -pyrimidinyl) hydrazone

MS (APCI, m / z): 468 (M + l

HPLC (reversed): Rt. (Min) = 4.30 Example 202: 3,4,5-trimed N- (4-anilino-6- {2-[(3,4,5-trimethoxyphenyl) [Methylidene] hydr-2-pyrimidinyl) hydrazones

 MS (APCI, m / z): 588 (M + D +

 HPLC (reversed): Rt. (Min) = 4.04 Example 203: 3,5-Dimethoxybenzaldehyde N- (4-anilino-6- {2-[(3,5-dimethoxyphenyl) methylidene] hydrazino}- 2-pyrimidinyl) hydrazone

MS (APCI, m / z): 528 (M + l) +

HPLC (reversed): Rt. (Min) = 4.35 Example 04: 2-Naphthaldehyde N- (4-anilino-6- {2- [2-naphthylmethylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 508 (M + lH

HPLC (reversed): Rt. (Rain) = 5.15 Example 205: 2,4-dimed N- (4-anilino-6- {2-[(2,4-dimethoxyphenyl) methylidene] hi 2- Pyrimidinyl) hydrazone

MS (APCI, m / z): 528 (M + D +

HPLC (reversed): Rt. (Min) = 4.62 Example 206: 5-Methoxy-1H-indole-3-carpaldehyde N- (4-anilino-6- {2-[(5-methoxy-1H-indolin-3-yl) methylidene] hydrazinoto 2 -Pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 546 (M + D +

HPLC (reversed): Rt. (Min) = 3.99 Example 207: 2-methyl-1H-indole-3-carpaldehyde N- (4-anilino-6- {2-[(2-methyl-1H- Indole-3-yl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 514 (M + D +

 HPLC (reversed): Rt. (Min) = 4.29 Example 208: 2,3,4,5,6-pentamethylbenzaldehyde N- (4-anilino-6- {2-[(2,3,4 , 5,6-Pentamethylphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 548 (M + D +

HPLC (reversed): Rt. (Min) = 5.89 Example 209: 2-Ethoxy-1-naphthaldehyde N- (4-anilino-6- {2-[(2-ethoxy-1-naphthyl) methylidene ] Hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 596 (M + D +

HPLC (reversed): Rt. (Min) = 5.43 Example 210: 9H-Fluoren-2-carbaldehyde N- (4-anilino-6- {2- [9H-fluoren-2-ylmethylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 584 (M + 1) +

HPLC (reversed): Rt. (Min) = 5.97. Example 211: 5-61 "tributyl) -2_hydroxybenzaldehyde N- [4-anilino- 6- (2-{[5- (tert-butyl) -2-hydroxyphenyl] methylidene} hydrazino) -2-pyrimidinyl] hydrazone

 MS (APCI, m / z): 552 (M + D +

 HPLC (reversed): Rt. (Min) = 7.28 Example 212: 4-hydroxy-2-methoxybenzaldehyde N- (4-anilino-6- {2hydroxy-2-methoxyphenyl) methylidene] hydrazino} -2- Pyrimidinyl) hydrazone

 MS (APCI, m / z): 500 (M + D +

HPLC (reversed): Rt. (Min) = 3.95 Example 213: 2,4,6-trimethoxybenzaldehyde N- (4- (2-methoxyanilino) -6- {2-[(2,4,6- Trimethoxyphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 618 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.61 Example 214: 3-hydroxy-4,5-dimethoxybenzaldehyde N_ [4- {2-[(3-hydroxy-4,5-dimethoxyphenyl) methylidene] ] Hydrazino} -6- (2-methoxydilino) -1-pyrimidinyl] hydrazone

MS (APCI, m / z): 590 (M + 1) +

HPLC (reversed): Rt. (Min) = 3.78 Example 215: 3,5-Dihydroxybenzaldehyde N- [4_ {2 _ [(3,5-dihydroxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino)- 2-Pirimigel] Hydrazone

 MS (APCI, m / z): 502 (M + D +

HPLC (reversed): Rt. (Min) = 3.38. Example 216: 2,5-Dimethylpenzaldehyde N- [4- {2-[(2,5-dimethylphenyl) methylidene] hydrazino 6- (2-methoxyanilino) -1-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, i / z): 494 (M + D +

HPLC (reversed): Rt. (Min) = 4.97 Example 217: 2-hydroxy-5-methoxybenzaldehyde [4- {2-[(2-hydroxy-5-methoxyphenyl) methylidene] hydrazino} -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 530 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.70 Example 218: 4-methoxy-1-naphthaldehyde N_ (4- (2-methoxyanilino) -6- {2-[(4-toxyl-tunaphthyl) methylidene] Hydrazino}-2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 598 (M + l) +

HPLC (reversed): Rt. (Min) = 5.27 Example 219: 2,6-Dimethoxybenzaldehyde N- [4- {2-[(2,6-dimethoxyphenyl) methylidene] hydrazino 6- (2-methoxyanilino ) -2-Pyrimidinyl] hydrazone

 MS (APCI, m / z): 558 (M + l) +

HPLC (reversed): Rt. (Min) = 4.42 Example 220: 2-hydroxy-5-methylbenzaldehyde N- [4- {2-[(2-hydroxy-5-methylphenyl) methylidene] hydrazino} -6- (2-Methoxyanilino)-2-pyrimidinyl] hydrazone

MS (APCI, m / z): 498 (M + l) +

HPLC (reversed): Rt. (Min) = 5.41. Example 221: 2-Hydroxy-3-do N- [4- {2-[(2-hydroxy-3-methylphenyl) methylidene] hi-6- (2-methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 498 (M + D +

HPLC (reversed): Rt. (Min) = 6.60 Example 222: 4- (tert-butyl) benzaldehyde N- [4 (2 _ {[4- (tert-butyl) phenyl] methylin} hydrazino) -6- ( 2-Methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetic acid

MS (APCI, m / z): 550 (M + l) +

HPLC (reversed): Rt. (Min) = 5.84 Example 223: 3-ethoxy-4-methoxybenzaldehyde N_ [4- {2 _ [(3-ethoxy-4-methoxyphenyl) methylidene] hydrazino} -6- ( 2-Methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 586 (M + D +

HPLC (reversed): Rt. (Min) = 4.29 Example 224: 4-methoxy-2,3-dimethylpenzaldehyde N- (4 '-(2-methoxyquinolinyl) -6- {2-[(4- Methoxy-2,3-dimethylphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoacetate

MS (APCI, m / z): 554 (M + l) +

HPLC (reversed): Rt. (Min) = 5.18 Example 225: 3-methoxybenzaldehyde N_ (4- (2-methoxyanilino) -6- {2-[(3-methoxyphenyl) methylidene] hydrazino} -2- Pyrimidinyl) hydrazone MS (APCI, m / z): 498 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.40. Example 226: 3,4,5-trime N- (4- (2-methoxyanilino) -6- {2-[(3,4,5-trimethoxyphene: -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 618 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.12 Example 227: 3,5-dimethoxybenzaldehyde N- [4- {2-[(3,5-dimethoxyphenyl) methylidene] hydrazino} -6 -(2-Methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 558 (M + D +

HPLC (reversed): Rt. (Min) = 4.47 Example 228: 2-Naphthaldehyde N- (4- (2-methoxyanilino) -6- {2- [2-naphthylmethylidene] hydrazino} -2-pyrimidinyl ) Hydrazone

MS (APCI, m / z): 538 (M + D +

HPLC (reversed): Rt. (Min) = 5.20 'Example 229: 2,4-dimethoxybenzaldehyde N- [4-{2-[(2,4-dimethoxyphenyl) methylidene] hydrazino} -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 558 (M + D +

HPLC (reversed): Rt. (Min) = 4.61 Example 230: 5-Methoxy-1H-indole-3-carbaldehyde N- (4- (2-methoxyanilino) -6- {2-[(5 -Methoxy-1H-indole-3_ '

{}-2-Pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 576 (M + D +

HPLC (reversed): Rt. (Min) = 4.04. Example 231: 2-Methyl-1H-indole-3-forcelpaldehyde N- (4- (2-methoxyanilino) -6- {2-[(2-methyl-1H-indole-3-yl) methylidene ] Hydrazino-2-pyrimidinyl) hydrazone trifluoacetate

MS (APCI, m / z): 544 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.33 Example 32: 2,3,4,5,6-pentamethylbenzaldehyde N_ (4- (2-methoxyanilino) -6- {2-[(2,3 , 4,5,6-Pentamethylphenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 578 (M + D +

HPLC (reversed): Rt. (Min) = 6.00 Example 233: 2-Ethoxy-1-naphthaldehyde N_ [4- {2-[(2-ethoxy-1_naphthyl) methylidene] hydrazino} -6- ( 2-methoxyanilino) -2 -pyrimidinyl] hydrazone trifluoroacetate +

MS (APCI, m / z): 626 (M + l) +

HPLC (reversed): Rt. (Min) = 5.54 Example 234: 9H-fluorene-2-carbaldehyde N_ [4- {2- [9H-fluorene_2_ ylmethylidene] hydrazino} -6- (2-methoxyanilino) -2 -Pyrimidinyl] hydrazone trifluoroacetate

 MS (APCI, m / z): 614 (M + D +

HPLC (reversed): Rt. (Rain) = 6.19

Nirino) -2-pyrimidinyl] hydrazone

 MS (APCI, m / z): 582 (M + l) +

HPLC (reversed): Rt. (Min) = 7.02. Example 236: Cyclobutane non-N- [6-anilino-2- (2-

ノ) -4 -Pyrimidinyl] hydrazone

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριη: 9.40 (s, 1H), 8.93 (s, 1H), 8.85 (s, 1H), 7.66 (d, 2H, J = 7.8 Hz), 7.23 (t, 2H, J = 7.9 Hz), 6.88

(t, 1H, J = 7.4 Hz), 5.85 (s, 1H), 2.87-3.00 (m, 8H), 1.88-1.98 (m, 4H) MS (APCI, m / z): 336 (M + 1) +

HPLC (reversed): Rt. (Min) = 3.83 Example 237: 1-phenyl-triethanone N- (4-anilino-6- {2- [1-phenylethylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 436 (M + l

HPLC (reversed): Rt. (Min) = 4.65 Example 238: Cyclopentene non-N- [6-anilino-2- (2-cyclopentylidenehydrazino) -4-pyrimidini Jre] hydrazone

MS (APCI, m / z): 364 (M + l) +

HPLC (reversed): Rt. (Min) = 4.15 Example 239: Tricyclopropyl-1-ethanone N- (4-anilino-6- {2- [tricycloprop-pyruethylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 364 (M + lH

HPLC (reversed): Rt. (Min) = 4.16 Example 240: 1-cyclobutyl-1-ethanone N- (4-anilino-6- {2- [tricyclobutylethylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 392 (M + lH

HPLC (reversed): Rt. (Rain) = 4.69. W

127 Example 241: Cyclohexanone N- [6-anilino-2- (2-cyclohexylidenehydrazino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 392 (M + l

HPLC (reversed): Rt. (Min) = 4.56 Example 242: Cycloheptanone N- [6-anilino-2- (2-i

Radino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 420 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.93 Example 243: Tetrahydro-4H-pyran-4-one N- [6-anilino-2- (2-tetrahydride mouth-4H-pyran-4-ylidene) Hydrazino)-4-pyrimidinyl] hydrazone

MS (APCI, m / z): 396 (M + l) +

HPLC (reversed): Rt. (Min) = 3.39

Three

Zon trifluoroacetate

MS (APCI, m / z): 504 (M + l) +

HPLC (reversed): Rt. (Min) = 5.98 Example 245: Cyclobutenonone N- [2- (2--6- (2-Methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 366 (M + l) +

HPLC (reversed): Rt. (Min) = 3.89. Example 246: 1- (2-furyl) -triethanone N- [2- {2- [to (2-f '

 Drazino} -6- (2-Methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 446 (M + 1) + HPLC (reversed): Rt. (Min) = 4.4 Example 247: Phenyl-1-ethanone N- (4- (2-methoxyanilino) -6- {2- [trifluorophenylethylidene] hydrazino} -2- Pyrimidinyl) hydrazone

MS (APCI, m / z): 466 (M + D +

HPLC (reversed): Rt. (Min) = 4.65 Example 248: Cyclopentene non-N- [2- (2- (2-methoxyanilino) -4-pyrimidinyl]

MS (APCI, m / z): 394 (M + l) +

HPLC (reversed): Rt. (Min) = 4.18 Example 249: Cyclopropyl-1-ethanone N- [2- {2- [Tricyclopropylethylidene] hydrazino} -6- (2-methoxyanilino)- 4-Pyrimidinyl] hydrazone

MS (APCI, m / z): 394 (M + D +

HPLC (reversed): Rt. (Min) = 4.22 Example 250: Cyclobutyl-1-ethanone- [2- {2- [1-hydrazino} -6- (2-methoxyanilino) -4-pyrimidinyl] hine

MS (APCI, m / z): 422 (M + D +

HPLC (reversed): Rt. (Min) = 4.74. Example 251: Cyclohexanone N-[-(2'-1- (2-methoxyanilino) -4-pyrimidinyl] h

MS (APCI, m / z): 422 (M + D +

HPLC (reversed): Rt. (Min) = 4.53 Example 252: Cycloheptanone N- [2- (2- (2-methoxyanilino) -4-pyrimidinyl] MS (APCI, m / z): 450 (Mil) +

 HPLC (reversed): Rt. (Min) = 4.96 Example 253: Tetrahydro-4H-pyran-4-one N- [6- (2-methoxyanilino) -2- (2-tetrahydro-4H-pyran-4-y Ridenhydrazino) -4-pyrimidinyl] hydrazone

 MS (APCI, m / z): 426 (M + l) +

ヒドラジノ] -4-ピリミジ 二ル}ヒドラゾン トリフルォロ酢酸塩 HPLC (reversed): Rt. (Min) = 3.41 Example 254 N-{6- (2-methoxyanilino)-2- [2- (3,

Hydrazino] -4-pyrimidinyl} hydrazone trifluoroacetate

MS (APCI, m / z): 534 (M + D +

HPLC (reversed): Rt. (Min) = 6.05 Example 255: 4- (dimethylamino) -1-naphthaldehyde N- [2- (2-{[4- (dimethylamino) -tonaphthyl] methylidene} hydrazino) _6-(2-Methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 624 (M + D +

HPLC (reversed): Rt. (Min) = 5.65. Example 256: ethyl 4- (1- {2- [2- (2-U- [4- (ethoxycarbonyl) phenyl] ethylidene} hydrazino) -6- (2-methoxyanilino) -4-pyrimidinyl] hydrazono} Ethyl) benzoate

'Η -Substitute R spectrum (270 MHz, DMS0-d ₆ ) (5 pm: 9.67 (s, 1H), 9.49 (s, 1H), 8.35 (s, 1H), 7.91-8.12 (m, 8H), 6.97 -7.10 (m, 4H), 6.53 (s, 1H), 4.31— 4.39 (m, 4H), 3.89 (s, 3H), 2.50 (s, 6H), 1.35 (t, 6H, J = 7.1 Hz) MS (APCI, m / z): 610 (M + l) +

HPLC (reversed): Rt. (Min) = 4.96 Example 257: 4,5-Dimethoxy-2-nitrobenzaldehyde N- (4-anilino-6_ {2-[(4,5-dimethoxy-2-nitrophenyl) methylidene] hydrazino} -2-pyrimidyl) hydrazone

Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) 0 pm: 11.16 (s, 1H), 11.05 (s, 1H), 9.13 (s, 1H), 8.67 (s, 1H), 8.61 (s, 1H) , 7.78 (d, 2H, J = 7.8 Hz), 7.

59-7.62 (m, 3H), 7.54 (s, 1H), 7.27 (t, 2H, J = 7.9 Hz), 6.96 (t, 1H, J = 7.3 Hz), 6.17 (s, 1H), 3.95-3.97 (m, 6H), 3.1 (s, 6H)

 MS (APCI, m / z): 618 (M + l

 HPLC (reversed): Rt. (Min) = 4.50 Example 258: 4,5-Dimethoxy-2--2-toluene Benzaldehyde N- [4- {2-[(4,5-Dimethoxy-2 -Nitrophenyl) methylidene] hydrazino} -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone

-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριιι: 11.14 (s, 1H), 10.99 (s, 1H), 8.65 (s, 1H), 8.60 (s, 1H), .8.20 (s, 1H), 8.13 (d, 1H, J = 7.8 Hz), 7.50-7.63 (m, 4H), 7.05 (d, 2H, J = 4.1 Hz), 6.86-7.01 (m, 1H), 6.22 (s, 1H) , 3.84-3.97 (m, 5H)

MS (APCI, m / z): 648 (M + D +

HPLC (reversed): Rt. (Min) = 4.49

{

Hydrazone

 MS (APCI, m / z): 500 (M + l) +

HPLC (reversed): Rt. (Min) = 4.86 Example 260: 4- (Methylsulfanyl) benzaldehyde N- [4- (2-methoxyanilino) -6- (2-{[4- (methylsulfanyl) phenyl] Methylidene} hydrazino) -2-pi Rimijinil] Hydrazone

 MS (APCI, m / z): 530 (M + l) +

 HPLC (reversed): Rt. (Min) = 5.07. Example 261: 3-Hydroxy-3-methoxybenzaldehyde N- (4-anilino-6- {2 [(4-hydroxy-3-methoxyphenyl, -2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 500 (M + l) +

HPLC (reversed): Rt. (Min) = 3.80 Example 262: 4-Hydroxy-3-methoxybenzaldehyde N- [4- {2-[(4-hydroxy-3-methoxyphenyl) methylidene] hydrazino } -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 530 (M + l) +

HPLC (reversed): Rt. (Min) = 3.81 Example 263: 5-{[2- (4-anilino-6- {2-[(3-hexyloxy-4-hydroxyphenyl) methylidene] hydrazino } -2-Pyrimidinyl) hydrazono] methyl} -2-Hydroxyamine MS (APCI, m / z): 528 (M + D +

 HPLC (reversed): Rt. (Min): 3.84 Example 264: 5-({2- [4- {2-[(3-hexyloxy-4-hydroxyphenyl) methylidene] hydrazino} -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazono} methyl)-2-hydroxybenzoic acid

 MS (APCI, m / z): 558 (M + D +

HPLC (reversed): Rt. (Min) = 3.87 Example 265: 1Η-imidazole-4_caproleptaldehyde N- (4-anilino-6- {2-[m_ Imidazole-4-ylmethylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetate

 MS (APCI, ra / z): 388 (M + l

 HPLC (reversed): Rt. (Min) = 2.98. Example 266: 1H-imidazole-4-carpaldehyde N- [4- {2- [1H-imidazole-4-ylmethylidene] hydrazino} -6- (2-methoxyanilino) _2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 418 (M + l) +

HPLC (reversed): Rt. (Min) = 3.03 Example 267: 1H-imidazole-2-hydroxypropyl N- (4-anilino-6- {2- [1H-imidazole-2-ylmethylidene] hydrazino} 2-Pyrimidinyl) hydrazone MS (APCI, m / z): 388 (M + l) +

HPLC (reversed): Rt. (Min) = 2.60 Example 268: Dihydro-3 (2H) -thiophenone N- [2- [2-dihydro-3 (2H) -thiophenylidenehydrazino] -6- (2-Methoxyanilino) -4-pyrimidinyl] hydrazone MS (APCI, m / z): 430 (M + D +

HPLC (reversed): Rt. (Min) 2 3.92 Example 269: Clos-4-hydroxyaldehyde N- (4-anilino-6- {2-[(2-clos-4-hydroxyhydroxy: hydrazino } _2 -Pyrimidinyl) hydrazone

 MS (APCI, m / z): 508 (M + l) +

HPLC (reversed): Rt. (Min) = 4.15 Example 270: Clo-4-4-hid N_ [4- {2-[(2-clo-4-4-hydroxyphenyl) pm 1 1 -6_ (2-methoxyanilino) -2-pyri W

133 Miguel] Hydrazone

 MS (APCI, m / z): 538 (M + D +

 HPLC (reversed): Rt. (Min) = 4.18.

{

 Hydrazone

 MS (APCI, m / z): 544 (M + D +

HPLC (reversed): Rt. (Min) = 5.23 Example 272: 3- (Trifluoromethyl) benzaldehyde N- [4- (2-methoxyanilino) -6 (2-{[3- (trifluoromethyl) Methylile) phenyl] methylidene} hydrazino)-2-pyrimidinyl] hydrazone

MS (APCI, m / z): 574 (M + l) +

HPLC (reversed): Rt. (Min) = 5.26 Example 273: 4- (

{[4-(Trifluolo

Hydrazone

 MS (APCI, m / z): 544 (M + l) +

HPLC (reversed): Rt. (Min) = 5.08 Example 274: 4- (Trifluoromethyl) be N- [4- (2-methoxyanilino) -6- (2-([4- Oromethyl) fue-drazino) -2 -pyrimidinyl] hydrazone

 MS (APCI, m / z): 574 (M + l '

HPLC (reversed): Rt. (Min)-5.16 Example 275: 4-Methyl-2-thiophene-powered lipoaldehyde N- (4-anilino-6- {2- [(3-Methyl-2-chenin-2-pyrimidinyl) hydrazone MS (APCI, m / z): 448 (M + D +

HPLC (reversed): Rt. (Min) = 4.53. Example 276: 2-Methyl-2-thiophencarpaldehyde N- (4_ (2-methoxyanilino) -6- {2-[(3-methyl-2-phenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone Trifluoroacetate

MS (APCI, m / z): 478 (M + D +

HPLC (reversed): Rt. (Min)-4.53

Example 277: 4-'N- [4-anilino-6- (2-{[4- (trifluoromethoxy) phenino'-2-pyrimidinyl] hydrazone

 MS (APCI, m / z): 576 (M + D +. '

HPLC (reversed): Rt. (Min) = 5.39 Example 278: 4- (Trifluorome N- [4_ (2-methoxymethoxylinino), 6- (2-{[4- (trifluoromethoxy) phene) ,

2-pyrimidinile] hydrazone

MS (APCI, m / z): 606 (M + l) +,

HPLC (reversed): Rt. (Min) = 5.31 Example 279: 5-nitro-2-thiophene N- (4-anilino-6- {2-[(5-nitro-2-enyl) methy2 -Pyrimidinyl) hydrazone MS (APCI, m / z): 510 (M + l) +

HPLC (reversed): Rt. (Min)-4.65 Example 280: 6_Nitro-2-thiophene-powered lipoaldehyde N- (4- (2-methoxyanilino) -6- {2-[(5- Ton-2--2-enyl) methylidene] hydrazino} -2-pyrimidinyl) MS (APCI, m / z): 540 (M + D +

 HPLC (reversed): Rt. (Min) = 4.72. Example 281: 5-methyl-2-thiophenecarbaldehyde N- (4-anilino-6- {2-[(5-methyl-2-phenyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetate

 MS (APCI, m / z): 448 (M + D +

 HPLC (reversed): Rt. (Min) = 4.54 Example 282: 6-methyl-2-thiophencarbaldehyde N- (4- (2-methoxyanilino) -6- {2-([5-methyl- 2-Chenyl) methylidene] hydrazino} -2 -pyrimidinylyl) hydrazone trifluoroacetate

MS (APCI, m / z): 478 (M + D +

HPLC (reversed): Rt. (Min) = 4.60 Example 283: Nitrobenzaldehyde N- (4-anilino-6- {2-[(4-ditrophenyl) methylidene] hydrazino} -2- Pyrimidinyl) hydrazone

MS (APCI, m / z): 498 (M + D +

HPLC (reversed): Rt. (Min) = 4.57 Example 284: 7-nitro-1,3-benzodioxol-5-carpaldehyde N- (4-anilino-6- {2- [ (6-Nitro-1,3-benzodioxoyl-5-yl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 586 (M + l) +

HPLC (reversed): Rt. (Min) = 4.54 Example 285: 7-Nitro-1,3-benzodioxole-5-hydroxylaldehyde N- (4- (2-methoxyanilino) -6- {2-[(6-Nitro-1,3-benzozoxol-5-yl) methyl Den] hydrazino}-2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 616 (M + D +

HPLC (reversed): Rt (min ) = 4.57 0 Example 286:. 2- (triphenylmethyl Ruo ii methyl) benzaldehyde N_ [4-Anirino - 6_ (2-

{[2- (Trifluoromethyl) phenino-2-pyrimigel] hydrazone

 MS (APCI, m / z): 544 (M + D +

HPLC (reversed): Rt. (Min) = 5.16 Example 287: 2- (Trifluoromethyl) benzaldehyde N- [4- (2-methoxyanilino) -6- (2-{[2- (trifluoromethyl ) Phenyl] methylidene} hydrazino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 574 (M + D +

HPLC (reversed): Rt. (Min) = 5.27 Example 288:

{[2- (Gifluo

Hydrazone

 MS (APCI, m / z): 540 (M + l) +

HPLC (reversed): Rt '. (Min) = 4.81 Example 289: 2- (difluorome N_ [4- (2-{[2- (difluoromethoxy) phene,' -6- (2-methoxya) Nilihar — pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 570 (M + l) +

HPLC (reversed): Rt. (Min) = 4.70 Example 290: 2-hydroxy-5- (trifluoromethoxy) benzaldehyde N- [4 -Anilino-6- (2-{[2-hydroxy-5- (trifluoromethoxy) phenyl] methylidene} hydrazino) -2-pyrimidinyl] hydrazone

 MS (APCI, m / z): 608 (M + l) +

 HPLC (reversed): Rt. (Min) = 6.66. Example 291: 3-Hydroxy-5-benzaldehyde- [4

-(2-{[2-hydroxy-5- (trifluoromethoxy) phenino

NO) -6- (2-Methoxyanilino) -2-pyrimidinyl] hydrazone

MS (APCI, m / z): 638 (M + l) +

HPLC (reversed): Rt. (Min) = 6.50 Example 292: 4- (Methylsulfonyl N_ [4-anilino-6- (2-{[4- (methylsulfonyl) 'phenihydrazino] -2-pyrimidinyl] hydrid Razon

 MS (APCI, m / z): 564 (M + l) +

HPLC (reversed): Rt. (Min) = 3.93 Example 293: 4- (Methylsulfonyl) benzo N- [4- (2-methoxyanilino) -6- (2-([4- (methylsulfonyl) phene [2-Pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 594 (M + D +

HPLC (reversed): Rt. (Min) = 3.75 Example 294: 3-{[2- (4-Anylino-6- {2-[(3-potoxy-2-hydroxyphenyl) methylidene] hydrazino}- 2-pyrimidinyl) hydrazono] methyl} -2-hydroxyammonium

MS (APCI, m / z): 528 (M + l) +

HPLC (reversed): Rt. (Min) = 4.02 Example 295: 3-({2- [4- {2-[(3-caproloxy-2-hydroxyphenyl) methylidene] hydrazino} -6- (2-methoxyanilino) -2-pyrimidini J J] hydrazono} Methyl) -2 -Hydroxybenzoic acid

MS (APCI, m / z): 558 (M + D +

HPLC (reversed): Rt. (Min) = 3.98. Example 296: 4-Methyl-1-indanone N- {4- (2-methoxyanilino) -6- [2- (4-methyl-2,3-dihydro-1H-indene_1-ylidene) hydrazino] -2 -Pirimigel} Hydrazon

MS (APCI, m / z): 518 (M + D +

 HPLC (reversed): Rt. (Min) = 5.78 Example 297: 2-Methyl-1-indanone N- {4- (2-methoxyanilino) -6- [2- (2-methyl-2,3 -Dihydro-1H-indene-1-ylidene) hydrazino] -2-pyrimidinyl} hydrazone trifluoroacetate

 MS (APCI, m / z): 518 (M + l '

HPLC (reversed): Rt. (Min) = 5.33 'Example 298: Ethyl 4- [2- (6-anilino-2- {2- [4- (ethoxycarponyl) cyclohexylidene] hydrazino} -4 -Pyrimidinyl) hydrazono] cyclohexanecarboxylate ·

 MS (APCI, m / z): 536 (M + lH

HPLC (reversed): Rt. (Min) = 4.40 Example 299: 1- (3,5-dihydroxyphenyl) -triethanone N- (4-anilino-6- {2- [1- (3, 5-dihydroxyphenyl) ethylidene] hydrazino}-2_pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 500 (M + lH

HPLC (reversed): Rt. (Min) = 3.45 Example 300: tri (3,5-dimethoxyphenyl) -triethanone N- (4-anilino-6- {2- [1- (3,5-dimethoxyphenyl) ethylidene] hydrazino} -2-pyrimidinyl) Hydrazone trifluoroacetate

MS (APCI, m / z): 556 (M + l

HPLC (reversed): Rt. (Min) = 4.58. Example 301: 1- (3,5-dimethylphenyl) -toethanone N- (4-anilino-6- {2- [1- (3,5-dimethylphenyl) ethylidene] hydrazino} -2-pyrimidinyl} ) Hydrazone trifluoroacetate

 MS (APCI, m / z): 492 (M + 1) +

 HPLC (reversed): Rt. (Min) = 5.50 Example 302: 3- {2- [6- (anilino-2--2- {2- [3- (3-cyanophenyl) ethylidene] hydrazino} -4-pyrimidinyl} ) Hydrazono] ethyl} benzonitrile trifluo mouth acetate

 MS (APCI, m / z) 486 (M + D +

HPLC (reversed): Rt. (Min) = 4.28 Example 303: 4-U- [2_ (6-anilino-2- {2- [tri (4-cyanophenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazono] ethyl} benzonitrile trifluo mouth acetate

 MS (APCI, m / z): 486 (M + D +

HPLC (reversed): Rt. (Min) = 4.30 Example 304: Ethyl 4- {2- [2- {2- [4- (ethoxycarbonyl) cyclohexylidene] hydrazino} -6- (2- Methoxyanilino) -4-pyrimigel] hydrazono} cyclohexanecarboxylate

MS (APCI, m / z): 566 (M + lH HPLC (reversed): Rt. (Min) = 4.43 Example 305: l- (3-methylphenyl) -toluenenon- (4- (2-methoxyanilino) -6- {2- [1- ( 3-Methylphenyl) ethylidene] hydrazino 2_pyrimidinyl) hydrazone

 MS (APCI, m / z): 494 (M + D +

 HPLC (reversed): Rt. (Min) = 5.04. Example 306: tri (3,5-dihydroxyphenyl) -triethanone N- [2- (2- [tri (3,5-dihydroxyphenyl) ethylidene] hydrazino} -6- (2-methoxyanilino)- 4-Pyrimidinyl] hydrazone

MS (APCI, m / z): 530 (M + l) +

HPLC (reversed): Rt. (Min) = 3.46 Example 307: tri (3,5-dimethoxyphenyl) -triethanone N- [2- {2- [tri (3,5-dimethoxyphenyl) ethylidene] ] Hydrazino} -6- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 586 (M + D +

HPLC (reversed): Rt. (Min) 4.60 Example 308: tri (3-hydroxyphenyl) -triethanone N- [2- [2- [tri (3-hydroxyphenyl) ethylidene] hydrazino} -6 -(2-Methoxyanilino) -4-pyrimidinyl] hydrazone

 MS (APCI, m / z): 498 (M + D +

HPLC (reversed): Rt. (Min) = 3.89 Example 309: l- (3,5-dimethylphenyl) -triethanone N- [2- {2- [tri (3,5-dimethylphenylene) Le) ethylidene] hydrazino}-6- (2-methoxyanilino) -4-pyrimidinire] hydrazone MS (APCI, m / z): 522 (M + l

HPLC (reversed): Rt. (Min) = 5.54 Example 310: 6,7,8,9-tetrahydro_5H-benzo [a] cyclohepten-5-one N- {6- (2-methoxyanilino) -2 -[2- (6,7,8,9-tetrahydro-5H-benzo [a] cycloheptene-5-ylidene) hydrazino] -4-pyrimidinyl} hydrazone trifluoroacetate

 MS (APCI, m / z): 546 (M + l) +

 HPLC (reversed): Rt. (Min) = 5.49. Example 311: Tri (4-methoxyphenyl) -1-ethanone N- (4- (2-methoxyphenylino) _6-{2- [tri (4-methoxyphenyl) ethylidene] hydrazino} -2-pyrimidinyl) hydrid Razone trifluoroacetate

MS (APCI, m / z): 526 (M + D +

HPLC (reversed): Rt. (Min) = 4.71 Example 312: Tri (2,3-dihydro_1H-indene-5-yl) -1-ethanone N- [2-(2_ [tri (2,3- Dihydro-1H-indene-5-yl) ethylidene] hydrazino 6- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 546 (M + D +

HPLC (reversed): Rt. (Min) = 5.81 Example 313: 3- (l- {2- [2- [2- [1- (3-Cyanophenyl) ethylidene] hydrazino] 6- (2-methoxyanilino)- 4-Pyrimidinyl] hydrazono} ethyl) benzonitrile Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) d ppm: 9.67 (s, 1H), 9.48 (s, 1H), 8.66 (brs, 1H), 8.13 -8.41 (m, 5H), 7.78-7.85 (m, 2H), 7.07-7.67 (m, 2H), 7.01-7.04 (m, 3H), 6.52 (s, 1H), 3.88 (s, 3H), 2.25 -2.33 (m, 6H)

MS (APCI, m / z): 516 (M + l) +

HPLC (reversed): Rt. (Min) = 4.34 Example 314: 4- (1- {2- [2- [1- [4- (4-cyanophenyl) ethylidene] hydrazino] 6- (2-methoxyanilino) -4-pyrimidinyl] hydrazono} ethyl) benzonitrile —NMR Spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 9.75 (s, 1H), 9.59 (s, 1H), 8.71 (s, 1H), 8.41 (s, 1H), 7.87-8.12 (m, 8H ), 7.03-7.09 (m, 3H), 6.55 (s,

1H), 3.89 (s, 3H), 2.24-2.37 (m, 6H)

MS (APCI, m / z): 516 (M + D +

HPLC (reversed): Rt. (Min) = 4.30 Example 315: 1- (3-Aminophenyl) -1-ethanone N- [2- {2- [tri (3-aminophenyl) ethylidene] hydrazino} -6- (2-Methoxyanilino) -4-pyrimidinyl] hydrazone

 MS (APCI, m / z): 496 (M + D +

 HPLC (reversed): Rt. (Rain) = 3.57. Example 316: 1-Acetyl-1H-l_3-propanolaldehyde- [2- {2-[(lT-cetyl-m-indenyl-3--6- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 600 (M + D +

HPLC (reversed): Rt. (Min) = 4.46 Example 317: 1- (4-chlorophenyl) -1-ethanone N- (4-anilino-6- {2- [tri (4-chlorophenyl)] [Ethylidene] hydrazino}-2-pyrimidinyl) hydrazone trifluoroacetate

 MS (APCI, m / z): 504 (M + D +

HPLC (reversed): Rt. (Min) = 5.14 Example 318: Phenyl (2-pyridinyl :: l) methanone N- (4-anilino-6- {2- [phenyl (2-pyridin: ί-2-pyrimidinylylene) ) Hydrazone MS (APCI, m / z): 562 (M + l) +

HPLC (reversed): Rt. (Min) = 4.41 Example 319: 1- (3-Chenyl) -toethanone N- (4-anilino-6- {2_ [to (3-Chenyl) ethylidene] hydrazino} -2-pyrimidinyl) hydrazone

MS (APCI, m / z): 448 (M + l) +

HPLC (reversed): Rt. (Min) = 4.54 Example 320: tri (3_nitrophenyl) -toethanone N- (4-anilino-6- {2- [tri (3-nitrophenyl) ethylidene] hydrazino} -2 -Pyrimidinyl) hydrazone

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.77 (s, 1H), 9.55 (s, 1H), 9.32 (s, 1H), 8.64 (s, 1H), 8.55 (s , 1H), 8.21-8.37 (m, 5H), 7.95 (d, 2H, J = 8.2 Hz), 7.70-7.77 (m, 2H), 7.31 (t, 2H, J = 7.2 Hz), 6.95 (t, 1H, J = 7.2 Hz), 6.27 (s, 1H), 2.40 (s, 6H)

MS (APCI, m / z): 526 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.45. Example 321: tert-butyl 4- [2- (6-anilino-2- {2- [1- (tert-butoxycarbonyl) -4-pyridinylidene] hydrazino} + pyrimidinyl) hydrazono] -1-pi-ぺ Lysine carboxylate

 MS (APCI, m / z): 594 (M + D +

 HPLC (reversed): Rt. (Rain) = 4.54 Example 322: 1-benzyl-4-piberidinone N_ {6-anilino-2- [2- (1-benzyl-4-piperidinylidene) hydrazino] -4- Pyrimidinyl} hydrazone

MS (APCI, m / z): 574 (M + D +

HPLC (reversed): Rt. (Min) = 2.75 Example 323: N- [3- (tri {2- [4- (2- {tri [3- (acetylamino) phenyl] ethylidene}} Hydrazino) -6-azirino-2-pyrimidinyl] hydrazono} ethyl) phenyl] acetoamide trifluoroacetate

MS (APCI, m / z): 550 (M + D +

HPLC (reversed): Rt. (Min) = 3.75 Example 324: Trimethyl-m-indole-3-carpaldehyde N- (6- (2-methoxyanilino) -2_ {2-([1-methyl -1H-indole-3-ylyl) methylidene] hydrazinoto 4-pyrimidinyl) hydrazone

MS (APCI, m / z): 544 (M + l

HPLC (reversed): Rt. (Min) = 4.59 Example 325: tri (4-chlorophenyl)-1-ethanone N- [2- {2- [tri (4-chlorophenyl) ethylidene ] Hydrazino} -6- (2-methoxyanilino) -4-pyrimidinyl] hydra MS (APCI, m / z): 534 (M + lH

 HPLC (reversed): Rt. (Min) = 5.23. Example 326: Phenyl (2-pyridinyl) methanone N- (4- (2-methoxyanilino) -6- {2- [phenyl (2-pyridinyl) methylidene] hydrazino} -2-pyrimidinyl) hydrazone

 MS (APCI, m / z): 592 (M + D +

HPLC (reversed): Rt. (Min) = 4.43 Example 327: 1- (2-aminophenyl) -1N—L2— {2- [1- (2-aminophenyl) ethylidene] hydrazino} -6 -(2-Methoxyanilino) -4-pyrimidinyl] hydra

MS (APCI, m / z): 496 (M + D +

HPLC (reversed): Rt. (Min) = 4.25 Example 328: 1- (3-Chenyl) -triethanone N- (4- (2- ^ toxianilino) -6- {2- [1- (3-Chenylyl) ethylidene] hydrazino} -2-pyrimidinyl) Hydrazone

MS (APCI, m / z): 478 (M + D +

HPLC (reversed): Rt. (Min) = 4.52 Example 329: 1- (2,4-dimethyl-1,3-thiazol-5-yl) -triethanone N- [2- {2- [ 1- (2,4-Dimethyl-1,3-thiazol-5-yl) ethylidene] hydrazino} -6- (2-Methoxyanilino) -4-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 536 (M + D +

HPLC (reversed): Rt. (Min) = 3.80 Example 330: tri (3-nitrophenyl) -toethanone N- (4- (2-methoxyphenyl)-6- {2-nitrophenyl) ethylidene] hydrazino}- 2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 556 (M + D +

HPLC (reversed): Rt. (Min) = 4.47. Example 331: tert-butyl 4-{2_ [2- {2- [1- (tert-butoxycarbonyl) -4-pyridinylidene] hydrazino] 6- (2-methoxyanilino) -4-pyrimidinyl] hydra

MS (APCI, m / z): 624 (Mll) +

 HPLC (reversed): Rt. (Min) = 4.57 Example 332: tribenzyl-4-piberidinone N_ [2- [2- (1-benzyl-4-piperidineylidene) hydrazino] -6- (2 -Methoxyanilino)-4-pyrimidinyl] hydrazone MS (APCI, m / z): 604 (M + l) +

HPLC (reversed): Rt. (Min) = 2.76 Example 333: N- [3- (tri {2- [4- (2-U- [3_ (acetylamino) phenyl] ethylidene}} Hydrazino) -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazono} ethyl) phenyl] acetoamide

 MS (APCI, m / z): 580 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.77 Example 334: 5- (Hydroxymethyl) -2_furaldehyde N- [6-anilino-2- (2-([5- (hydroxymethyl) -2- Furyl] methylidene} hydrazino) -4-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 448 (M + l) +

HPLC (reversed): Rt. (Min) = 3.28 Example 335: 2-{[2- (6-anilino-2- {2-[(2-cyanophenyl) methylidene] hydrazino} -4-pyrimidinyl) hydrazono] Methyl} benzonitrile

-NMR spectrum (270 MHz, DMSO-d ₆ ) δ ρπι: 11.33 (s, 1H), 11.24 (s, 1H), 9.29 (s, 1H), 8.50 (s, 1H), 8.43 (s, 1H). 6.96-8.19 (m, 13H), 6.25 (s, 1H)

 MS (APCI, m / z): 458 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.33. Example 336: 1,3-Thiazol-2-propanolaldehyde N- (6-anilino-2- {2- [1,3-thiazol-2-ylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 422 (M + l) +

HPLC (reversed): Rt. (Min) = 3.70 Example 337: 2-furaldehyde N- (6-anilino-2- {2- [3-furylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 388 (M + l) +

HPLC (reversed): Rt. (Min) = 3.91 Example 338: 3-Fluoro-2N- (6-anilino-2- {2-[(3-fluoro-2-methylphenyl) methy1.-4-pyrimidinyl) hydrazone

 MS (APCI, m / z): 472 (M + l) +

HPLC (reversed): Rt. (Min) = 4.74 Example 339: 4- (Dimethylamino) benzaldehyde N_ [6-anilino-2- (2-{[4- (dimethylamino) phenyl] methylidene} hydrazino) -4- Pyrimidinyl] hydrazones

 MS (APCI, m / z): 494 (Mll) +

HPLC (reversed): Rt. (Min) = 4.94 Example 340: l- [3- (Dimethylamino) phenyl] -1N- [4-anilino-6- (2- {tri [3- (dimethylamino) phenyl]] Ethylidene} hi 2-pyrimidinyl] hydrazone

 MS (APCI, m / z): 522 (Mll) +

 HPLC (reversed): Rt. (Min) = 4.64. Example 341: N- [4-({2- [4-(2-{[4- (acetylamino) phenyl] methylidene} hydrazino) -6-anilino-2-pyrimidinyl] hydrazono} methyl) phenyl] acetamy F

MS (APCI, m / z): 522 (M + l

HPLC (reversed): Rt. (Min) = 3.70 Example 342: trimethyl-m-indole-3-carpaldehyde N- (6-anilino-2- 2- {2-[(trimethyl-1H-indole- 3-yl) methylidene] hydrazino}-4-pyrimidinyl) hydrazone

 MS (APCI, m / z): 514 (M + D +

HPLC (reversed): Rt. (Min) = 4.56 Example 343: 1-Acetyl-1H-indole-3 -caproleptaldehyde N- (2- {2 -— ((1-Acetyl-1H-indole-3-yl) methylidene] hydrazino 6-anilino-4 -Pyrimidinyl) hydrazone

MS (APCI, m / z): 570 (M + D +

HPLC (reversed): Rt. (Min) = 4.47 Example 344: 4-N- [6-anilino + (2-{[4--4-pyrimidinyl]

 MS (APCI, m / z): 594 (M + l) +

HPLC (reversed): Rt. (Min) = 5.61 Example 345: 5- (hydroxymethyl) -2_N— [2 -— (2-({[5- (hydroxy

 -6- (2-Methoxyanilino) -4-pyrimidinyl] hydrazone trifluoroacetate

 MS (APCI, m / z): 478 (M + D +

HPLC (reversed): Rt. (Min) = 3.27. Example 346: 2-({2- [2_ {2-[(2-sia (2-methoxyanilino) -4-pyrimidinyl]

MS (APCI, m / z): 488 (M + D +

HPLC (reversed): Rt. (Min) = 4.36 Example 347: 1,3-thiazole-2-carbaldehyde N- (6- (2-methoxyanilino) -2- {2- [1,3-thiazole-2 -Irmethylidene] hydrazino 4-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 452 (M + l) +

HPLC (reversed): Rt. (Min) = 3.73 Example 348: 1- (2-Chenyl) -1-ethanone N- (4- (2-methoxyanilino) -6- {2- [1- (2-Chenyl) ethylidene] hydrazino} -2-pyrimidinyl) hydrazone triflu Oroacetate

MS (APCI, m / z): 478 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.40 Example 349: 1_ (5-methyl_2_thenyl) -1-ethanone N- (4- (2-methoxyanilino) -6- {2- [1 -(5-methyl-2-chenyl) ethylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, m / z): 506 (M + l) +

HPLC (reversed): Rt. (Min) = 4.83 Example 350: 1_ (5-chloro-2-Chenyl) -1-ethanone N- [2- {2- [1_ (5-chloro-2 -Chenyl) ethylidene] hydrazino}-6- (2-methoxyanilino) -4-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 546 (M + l) +

HPLC (reversed): Rt. (Min) = 5.14. Example 351: 1- (3-Methyl-2_thenyl) -1-ethanone N- (4- (2-methoxyanilino) -6- {2- [1- (3-methyl-2-methyl-2-enyl)] Ethylidene] hydrazino} -2-pyrimidinyl) hydrazone trifluoroacetate

MS (APCI, ra / z): 506 (M + l

HPLC (reversed): Rt. (Min) = 4.67 Example 352: Tri [3- (dimethylamino) phenyl] -1 -ethanone N- [2_ (2- {1- [3- (dimethylamino) phenyl]] Ethylidene} hydrazino) -6- (2-methoxyanilino) -4-pyrimigel] hydrazone trifluoroacetate

MS (APCI, m / z): 552 (M HPLC (reversed): Rt. (Min) = 4.56 Example 353: 1- (3,5-difluorophenyl) -1 -ethanone N- [2- {2- [1- (3,5-difluorophenyl) ) Ethylidene] hydrazino 6_ (2-methoxyanilino) -4-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 538 (M + l) +

HPLC (reversed): Rt. (Min) = 4.84 Example 354: tri [3- (trifluoromethoxy) phenyl] -1-ethanone N- [4- (2-methoxyanilino) -6- (2- {3- [3- (trifluoromethoxy) phenyl] ethylidene} hydrazino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 634 (M + l

HPLC (reversed): Rt. (Min) = 5.26 Example 355: 1- [3- (Trifluoromethyl) phenyl]-1-ethanone N- [4- (2-Methoxyanilino)- 6_ (2-U- [3- (trifluoromethyl) phenyl] ethylidene} hydrazino) -2-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 602 (M + l) +

HPLC (reversed): Rt. (Rain) = 5.12. Example 356: 1- [3-Fluoro-5- (trifluoromethyl) phenyl] -toluenenonΝ- [2- (2- {tri [3-fluoro-5- (trifluoromethyl)] [Phenyl] ethylidene} hydrazino) -6- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 638 (M + 1) +

HPLC (reversed): Rt. (Min) = 5.43 Example 357: tri (3-pyridinyl) -triethanone N- (4- (2-methoxyanilino) -6- {2- (1- (3-pyridinyl) ) Ethylidene] hydrazino} _2-pyrimidinyl) hydrazone MS (APCI, m / z): 468 (M + l) + HPLC (reversed): Ri. (Min) = 3.09 Example 358: tri (4-isobutylphenyl) -1-ethanone N- [2- {2- [1- (4-isobutylphenyl) ethylidene] Hydrazino 6- (2-methoxyanilino) -4-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 578 (M + D +

HPLC (reversed): Rt. (Min) = 6.64 Example 359: Trimethyl_1H-imidazole-2-carpaldehyde N- (4-anilino-6- {2-[(trimethyl-1H-imidazole) -2-yl) methylidene] hydrazino} -2-pyrimidineylyl) hydrazone

MS (APCI, m / z): 416 (M + l) +

HPLC (reversed): Rt. (Min) = 2.61 Example 360: Trimethyl-1H-imidazole-2-carboxaldehyde N_ (4- (2-methoxyanilino) -6- {2-[(trimethyl- 1H-imidazole-2-yl) methylidene] hydrazino}-2-pyrimidinyl) hydrazone ''

MS (APCI, m / z): 446 (M + l) +

 HPLC (reversed): Rt. (Min) = 2.64. Example 361: 3,5-Dimethyl-1-phenyl-1H-pyrazole-4_caproleptaldehyde N- (4-anilino-6- {2-[(3,5-dimethyl-1-phenyl-1H-pyrazole) -4-yl) methylidene] hydrazino 2-pyrimidinyl) hydrazone trifluoroacetate

 MS (APCI, m / z): 596 (M + D + '

HPLC (reversed): Rt. (Min) = 4.43 Example 362: 3,5-Dimethyl-1_phenyl-1H-pyrazole-4-carboxaldehyde N- [4- {2-[(3 , 5-Dimethyl-1-phenyl-1H-pyrazole + yl) methylidene] hydrazino}-6- (2-methoxyanilino) -2-pyrimidyl] hydrazone trifluoroacetic acid salt

lH-NMR spectrum (270 MHz, DMSO-d ₆ ) <5ppm: 12.07 (s, 1H), 11.53 (s, 1H), 9.67 (s, 1H), 8.33 (s, 1H), 8.5 (s, 1H), 7.45-7.54 (m, 11H), 7.22-7.3

1 (m, 2H), 7.04-7.06 (m, 1H), 5.94 (s, 1H), 3.86 (s, 3H), 2.24-2.51 (m, 12H)

 MS (APCI, m / z): 626 (M + D +

HPLC (reversed): Rt. (Min) = 4.45 Example 363: 4-quinolinecarpaldehyde N- (6-anilino-2- {2- [4-quinolinylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 510 (M + D +

HPLC (reversed): Rt. (Min) = 3.46 Example 364: 5-quinolinecarpaldehyde N- (6- (2-methoxyanilino) -2- {2_ [4-quinolinylmethylidene] hydrazino} -4- Pyrimidinyl) hydrazone trifluoroacetate

 MS (APCI, m / z): 540 (M + D +

HPLC (reversed): Rt. (Min) = 3.56

Pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 554 (M + l) +

HPLC (reversed): Rt. (Min) = 5.24. Example 366: Isonicotinaldehyde N- (6-anilino-2- {2- [4-pyridinylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 410 (M + D +

HPLC (reversed): Rt. (Min) = 2.67 Example 367: 2-Thiophenecarpaldehyde N_ (6-anilino-2- {2- [2-Cenylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 420 (M + D +

HPLC (reversed): Rt. (Min) = 4.12 Example 368: 1-Methyl-1H-pyrrol-2--2-propanolaldehyde N- (6-anilino + {2-[(trimethyl-1H-pyrrole- 2-yl) methylidene] hydrazino 4_pyrimidinyl) hydrazone

 MS (APCI, m / z): 414 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.18 Example 369: Cyclopropanecarpaldehyde N- (6-anilino-2- {2-mouth pyrmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 336 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.83 'Example 370: 2-thiophencarpaldehyde N- (6-anilino-2- {2- [3-Cenylmethylidene] hydrazino 4-pyrimidinyl) hydrazone

MS (APCI, m / z): 420 (M + D +

 HPLC (reversed): Rt. (Min) = 4.21. Example 371: 2,3,6-Trifluorobenzaldehyde N- (6-anilino-2- {2-[(2,3,6-trifluorophenyl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

丽R spectrum _{(270 MHz, DMS0-d 6} ) dpp: 11.11 (s, 1H), 11.00 (s, 1H), 9.29 (s, 1H), 8.25 (s, 1H), 8.19 (s, 1H), 7.93 (d, 2H, J = 7.8 Hz), 7.47-7.51 (m, 2H), 7.19-7.29 (m, 4H), 6.93 (t, 1H, J = 7.2 Hz), 6.14 (s, 1H) MS (APCI, m / z): 516 (M + l

HPLC (reversed): Rt. (Min) = 4.54 Example 372: Tolbenzofuran-2-caprolaldehyde N- (6-anilino-2- 2- {2- [1-benzofuran-2-ylmethylidene] hydrazino}- 4-pimidinyl) hydrazone

MS (APCI, m / z): 488 (M + l) +

HPLC (reversed): Rt. (Min) = 4.69 Example 373: 2-furaldehyde N- [2- {2- [3-furylmethylidene] hydrazino} -6- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 418 (M + 1) +

HPLC (reversed): Rt. (Min) = 3.98 Example 374: 3-nitrobenzaldehyde N- (6-anilino-2- {2 _ [(3-nitrophenyl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 498 (M + l) +

HPLC (reversed): Rt. (Min) = 4.39 Example 375: 1H-pyrrole-2-carbaldehyde N- (6-anilino-1-2- {2- [1H-pyrrol-2-ylmethylidene] hydrazino 4 -Pyrimidinyl) hydrazone trifluo mouth acetate

 MS (APCI, m / z): 386 (M + D +

 HPLC (reversed): Rt. (Min) = 4.05. Example 376: Nicotinaldehyde N- (6-anilino-2- {2- [3-pyridinylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 410 (M + D + '

HPLC (reversed): Rt. (Min) = 3.06 Example 377: 3-Pyridine-powered lipoaldehyde N- (6- (2-methoxyanilino) -2_ {2- [2-pyridinylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone trifluoroacetate

 MS (APCI, m / z): 440 (M + l) +

HPLC (reversed): Rt. (Min) = 3.46 Example 378: Isonicotinaldehyde N- (6- (2-methoxyanilino) -2- 2- {2- [4-pyridinylmethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone

Ή-NMR spectrum (270 MHz, DMSO- d ₆ ) <5ppm: 11.20 (s, 1H), 11.02 (s, 1H), 8.53-8.67 (m, 5H), 8.38 (s, 1H), 8.10 (s, 1H), 8.04 (s, 1H), 7.66-7.89 (m, 4H), 6.99-7.05 (m, 3H), 6.48 (s, 1H), 3.88 (s, 3H)

MS (APCI, m / z): 440 (M + l) +

HPLC (reversed): Rt. (Min) = 2.72 Example 379: 2-thiophene-powered lipoaldehyde N- (6- (2-methoxyanilino) -2- (2- [2-Cenylmethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone

MS (APCI, m / z): 450 (M + 0 +

HPLC (reversed): Rt. (Min) = 4.19 Example 380: trimethyl-lH-pyrrolyl-2_carpaldehyde N- (6- (2-methoxy-2-arino) -2- (2-[(1 -Methyl-1H-pyrrol-2-yl) methylidene] hydrazino 4 -pyrimidinyl) hydrazone

MS (APCI, m / z): 444 (M + D +

 HPLC (reversed): Rt. (Min) = 4.18. 'Example 381: 5-de N- [2- {2- [cyclopropylpropylmethylidene] hydrazino} -6- (2-methoxyani-4-pyrimidinyl] hydrazone MS (APCI, m / z): 366 (M + D +

HPLC (reversed): Rt. (Min) = 3.86 Example 382: 2-thiophenecarbaldehyde N- (6- (2-methoxyanilino) -2- {2- [3- ceenylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 450 (M + D +

HPLC (reversed): Ri. (Min) = 4.25 Example 383: 2,3,6-Trifluorobenzaldehyde (6_ (2_methoxyanilino) -2_ {2-[(2,3,6-tri Fluorophenyl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 546 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.55 Example 384: Tribenzofuran-2-carboxaldehyde N- [2- {2- [1-benzofuran-2-ylmethylidene] hydrazino} -6- ( 2-Methoxyanilino) -4-pyrimidinyl] hydrazone

 MS (APCI, m / z): 518 (M + l) +

HPLC (reversed): Rt. (Rain) = 4.71 Example 385: 2-Fluoro-2-methylbenzaldehyde N- [2- {2-[(3-fluoro-2-methylphenyl) methylidene] hydrazino} -6 -(2-Methoxyanilino) -4-pyrimidinire] hydrazone

MS (APCI, m / z): 502 (M + D +

HPLC (reversed): Rt. (Min) = 4.74. {twenty three

MS (APCI, m / z): 528 (M + l) l

HPLC (reversed): Rt. (Min) = 4.45 Example 387: 1H-Pyrrol-2-carbaldehyde N- (6- (2-methoxyanilino) -2- (2- [1H-pyrrole-2-ylmethylidene] hydrazino} -4-pyrimigyl) hydrazone MS (APCI , m / z): 416 (M + l) +

HPLC (reversed): Rt. (Min) = 4.07 Example 388: Nicotinaldehyde N- (6- (2-methoxyanilino) -2--2- {2- [3-pyridinylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

MS (APCI, m / z): 440 (M + l) +

HPLC (reversed): Rt. (Min) = 3.08 Example 389: 4- (dimethylamino) benzaldehyde N- [2- (2 _ {[4- (dimethylamino) phenyl] methylidene} hydrazino) -6- (2 -Methoxyanilino) -4-pyrimidinyl] hydrazone trifluoroacetate

MS (APCI, m / z): 524 (M + D +

HPLC (reversed): Rt. (Min) = 4.78 Example 390: N- [4-({2- [4- (2-{[4- (acetylamino) phenyl] methylidene} hydrazino) -6- (2-methoxyanilino) -2-pyrimidinyl] hydrazono} methyl) phenyl] acetoamide

MS (APCI, m / z): 552 (M + l) +

HPLC (reversed): Rt. (Min) = 3.75. Example 391: Tri (4-pyridinyl) -triethanone 0- [4- (2-methoxyanilino) -6-({[tri (4-pyridinyl) ethylidene] amino} oxy) -2-pyrimidinyl] oxime sodium hydride (155 °, 55 ° C, 155 mg, 3.57 marl ol) was dissolved in DMF (3 ml), and the mixture was cooled under ice-cooling and 1_pyridine-4-yl-ethanone oxime hydrochloride prepared in Reference Example 86 (270 mg, 1.57 wakeup) and stirred at room temperature for 5 minutes. Furthermore, (2,6-dichloropyrimidin-4-yl)-(2-methoxyphenyl) amine (193 mg, 0.714 mmol) produced in Reference Example 1 was added thereto, and the mixture was added at 90 ° C. Stirred for hours. After the reaction, water was added, and the deposited precipitate was collected by filtration. Then, the desired product (123 mg, 37%) was obtained by washing with a mixed solvent of water and ether / ethyl acetate.

 MS (APCI, m / z): 470 (Mil) +

 HPLC (reversed): Rt. (Min) = 3.76. Example 392: l- (4-pyridinyl) -1-ethanone N- (4- (2-methoxyphenoxy) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -2-pyrimidinyl ) Hydrazone N- (2,6-dihydrazinopyrimidin-4-yl) -phenylamine (0.076 mg, 20 mg) prepared in Example was dissolved in dioxane (0.5 ml) to give 4-acetylpyridine (0. 051 ml, 0.46 mmol) was added and the mixture was refluxed for 15 hours. After the reaction, the solvent was evaporated under reduced pressure, and a mixed solvent of ether and ethyl acetate was added to the residue to suspend the residue. The precipitated solid was collected by filtration and filtered, and washed again with a mixed solvent of ether and ethyl acetate to obtain the desired product.

 MS (APCI, m / z): 469 (M + l) +

HPLC (reversed): Rt. (Min) = 2.78. Example 393

 1- (4-Pyridinyl) -toethanone N- (2-cyclopropyl-6- {2- [to (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The 4,6-dihydrazino-2-cyclopropylpyrimidine (90 mg,

0.5 mmol) was dissolved in dioxane (3 ml), and 4-acetylpyridine (0.332 ml, 3 mmo) was dissolved.

After 1) was added, the mixture was heated under reflux for 18 hours. After evaporating the solvent under reduced pressure, an ethyl acetate-ethyl ether solution was added to the residue and suspended. The precipitated solid was pulverized and collected by filtration to obtain the desired product (96 mg, 50%).

'Η-wake R spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 10.27 (brs, 2H), 8.64 (dd, 4H,

J = 1.6 Hz, 4.9 Hz), 7.76 (dd, 4H, J = 1.6 Hz, 4.9 Hz), 6.97 (s, 1H), 2.

33 (s, 6H), 1.98-1.95 (m, 1H), 1.08-1.02 (m, 2H), 0.95-0.90 (m, 2H)

HPLC (reversed): Rt. (Min) = 2.57

MS (APCI, m / z): 387 (M + l) +. PT / JP03 / 05216

159

Example 394

 1- (4_pyridinyl) -triethanone N_ (2- (2-methoxyanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 2- (2-Methoxyanilino) -4,6-dihydrazinopyrimidine (1.5 mmol) produced in Reference Example 9 was dissolved in dioxane (5 ml), and 4-acetylpyridine (1.7 ml, 15.6 thigh) was dissolved. ol), and the mixture was stirred for 18 hours. After evaporating the solvent under reduced pressure, an ethyl acetate-diethyl ether solution was added to the residue and suspended. The precipitated solid was pulverized and collected by filtration to obtain the desired product (406 mg, 58%). '

NMR-NMR spectrum (270 MHz, DMSO-d ₆ ) 5 ppm: 10.24 (s, 2H), 8.83 (d, 1H, J = 6.8 Hz), 8.66 (d, 4H, J = 4.9 Hz), 7.79 (d, 4H, J = 4.9 Hz), 7.43 (s,

1H), 7.04-6.94 (m, 3H), 6.74 (s, 1H), 3.93 (s, 3H), 2.35 (s, 6H)

HPLC (reversed): Rt. (Min) = 2.86

MS (APCI, m / z): 468 (M + 1) +

Elemental analysis value (C ₂₅ H ₂₅ F ₂ N ₉ 0)

Calculated values: C: 64.22; H: 5.39; N: 26.96

Actual measurement: C: 63.94; H: 5.30; N: 26.56. Example 395

1- (4-Pyridinyl) -1-ethanone 0- [2- (2-Methoxyanilino) -6-({[(4- (pyridinyl) ethylidene] amino} oxy) -4-pyrimidinyl] oxime

Sodium hydride (oil, 55%, 100 mg, 2.27 mmol) was dissolved in DMF (2 ml), and ice-cooled, tripyridine-4-ethanone oxime hydrochloride prepared in Reference Example 86 (172 mg, 1 mmol) Was added and stirred at room temperature for 5 minutes. Further, 2- (2-methoxyanilino) -4,6-dichloropyrimidine (112 mg, 0.42 IMOI) produced in Reference Example 9 was added, and the mixture was stirred at 60 ° C. for 3 hours. After the reaction, the solvent was distilled off under reduced pressure, and extraction was performed with ethyl acetate-water. The organic layer was dried over anhydrous sodium sulfate and concentrated. After that, the solvent was distilled off under reduced pressure, and the residue was suspended by adding a solution of ethyl acetate-getyl ether. The precipitated solid was pulverized and then collected by filtration to obtain the desired product (16 mg, 8%). 'Η-丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 8.75 (dd, 4H, J = 1.7 Hz, 4.5 Hz), 8.35 (s, 1H), 8.10 (d, 1H, J = 7.3) , 7.79 (dd, 4H, J = 1.7 Hz, 4.5 Hz), 7.09-7.07 (m, 2H), 7.01-6.97 (m, 1H), 6.72 (s, 1H), 3.86 (s, 3H), 2.50 ( s, 6H)

HPLC (reversed): t. (Min) = 4.66

MS (APCI, m / z): 470 (M + l) +. Example 396

l- (4-pyridinyl) -triethanone N- (2,6-bis {2- [tri (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 2,4,6-Trihydrazinopyrimidine (1 ol) was dissolved in dioxane (5 ml), and 4-acetylpyridine (0.66 ml, 6 mmol) was added, followed by heating under reflux for 18 hours. After the solvent was distilled off under reduced pressure, an ethyl acetate-getyl ether solution was added to the residue and suspended. The desired product was obtained by pulverizing the precipitated solid and collecting the solid by filtration.

HPLC (reversed): Rt. (Min) = 2.36

MS (APCI, m / z): 480 (Μ + 1) +. Example 397

 6-Methoxy-1-indanone N- {2- (2-methoxyanilino) _6_ [2- (6-methoxyindan-triylidene) hydrazino] -4-pyrimidinyl} hydrazone

 2- (2-Methoxyanilino) -4,6-dihydrazinopyrimidine (0.1 mmol) is dissolved in dioxane (1 ml), 6-methoxyindanone (57 mg, 0.35 mmol) is added, and then 15 hours. Stirred. After the solvent was distilled off under reduced pressure, an ethyl acetate-jetil ether solution was added to the residue and suspended. The precipitated solid was pulverized, filtered, and dried under reduced pressure to obtain the desired product.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) 6ppm: 9.67 (brs, 2H), 8.76 (brs, 1H), 7.32-7.20 (m, 5H), 7.02-6.91 (m, 5H), 3.85 (s , 3H), 3.80 (s, 6H), 3.05- 2.94 (m 8H)

HPLC (reversed): Rt. (Min) = 5.08 MS (APCI, m / z): 550 (M + l) +. Thereafter, the same reaction as in Example 397 was carried out and purification was carried out to obtain the desired compounds of Examples 398 to 508. Example 398: 1- (2-Chenyl) -1-ethanone N- (2- (2-methoxyanilino) -6- {2- [1- (2-Chenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

-NMR spectrum (270 MHz, DMSO- d ₆ ) <5 ppm: 8.64 (brs, 1H), 7.46-7.62 (m, 5H), 6.95-7.11 (m, 6H), 6.48 (s, 1H), 3.91 (s , 3H), 2.40 (s, 6H)

HPLC (reversed): Rt. (Min) = 4.65

MS (APCI, m / z): 478 (M + 1) + Example 399: 1_ (2-Chenyl) -triethanone (2- (2-methoxy-5-methylanilino) -6- {2- [1 -(2-Chenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazones

lH_NMR spectrum (270 MHz, DMSO-d ₆ ) (5 pm: 7.43-7.60 (m, 5H), 6.79-7.10 (m, 4H), 3.86 (s, 3H), 2.32-2.50. (m, 9H)

HPLC (reversed): Rt. (Min) = 5.00

MS (APCI, m / z): 492 (M + 1) + Example 400

 N- (l- {2- [6- {2- [5- (acetylamino) indane-1-ylidene] hydrazino}-2- (2-methoxyanilino) -4-pyrimidinyl] hydrazono} indan-5-yl) Acetamime F HPLC (reversed): Rt. (Min) = 4.05

MS (APCI, m / z): 604 (M + l) +. Example 401: N- (l- {2- [6- {2- [5- (acetylamino) indan-1-ylidene] hydrazino] 2- (2-methoxy-5-methylanilino) -4-pyrimidinyl] hydrazono } Inda N-5-yl) acetamide

 HPLC (reversed): Rt. (Min) = 4.17

 MS (APCI, m / z): 618 (M + 1) + Example 402: tri (4-cyanophenyl) -triethanone 1 ^-(2_anilino-6- {2- [1- (4-cyanophenyl) Ethylidene] hydrazino}-4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.09

MS (APCI, m / z): 486 (M + 1) + Example 403: N- {2- [2- (2- [5- (acetylamino) indane-1-ylidene] hydrazino 2-anilino- " 4-Pyrimidinyl) hydrazono] indan-5-yl} acetamide HPLC (reversed): Rt. (Min) = 4.02

MS (APCI, m / z): 574 (M + 1) + Example 04: 6-Methoxy-1-indanone N- [6- [2- (6-Methoxyindan-1-ylidene) hydrazino] -2- (2-Methoxy-5-methylanilino) -4-pyrimidinyl] hydra

HPLC (reversed): Rt. (Min) = 5.10

MS (APCI, m / z): 564 (M + 1) + Example 05: Methyl 4-α- {2- [6_ (2- {to [4- (methoxycarbonyl) phenyl] ethylidene} hydrazino)- 2- (2-methoxy-5-methylanilino) -4_pyrimidinyl] h

HPLC (reversed): Rt. (Min) = 5.10

MS (APCI, m / z): 568 (M + l) +. Example 406: Methyl 4- (2- {2- [2- (2-methoxyanilino) -6_ (2- {1- [4- (methoxypropanol) phenyl] ethylidene} hydrazino) -4-pyrimidinyl] hydrazono} Chill) benzoate 'H-NMR spectrum (270 MHz, DMSO-d ₆ ) <5 pm: 11.19 (brs, 2H), 8.53 (brs, 1 H), 8.16 (s, 2H), 8.07 (d, 4H, J = 8.4 Hz ), 7.84 (d, 4H, J = 8.4 Hz), 7.38 (s, 1H), 7.05-6.94 (m, 3H), 6.51 (s, 1H), 3.89 (s, 9H)

HPLC (reversed): Rt. (Min) = 4.77

MS (APCI, i / z): 582 (M + 1) + Example 407: 2,2,3-Dimethoxybenzaldehyde N- [6- {2-[(2,3-dimethoxyphenyl) methylidene] hydrazino} -2 -(2-Methoxyanilino) -4- -pyrimidinyl] hydrazone

'H-NMR spectrum (270 MHz, DMSO-d ₆ ) (5 ppm: 10.94 (s, 2H), 8.60-8.58 (m, 1H), 8.37 (s, 2H), 7.46 (d, 2H, J = 7.6 Hz ), 7.31 (s, 1H), 7.17 (t, 2H, J = 7.9 Hz), 7.08-7.00 (m, 3H), 6.95-6.43 (m, 2H), 3.90 (s, 3H), 3.84 (s, 6H), 3.79 (s, 6H)

HPLC (reversed): Rt. (Min) = 4.57

MS (APCI, m / z): 558 (Mil) + Example 408: 2,5-dimethoxybenzaldehyde N- [6- [2-[(2,5-dimethoxyphenyl) methylidene] hydrazino 2- 2- (2 -Methoxyanilino)-4-pyrimidinyl] hydrazone

NMR spectrum (270 MHz, DMS0-d ₆ ) δρριιι: 10.95 (1, 2Η), 8.61-8.59 (m, 1H), 8.40 (s, 2H), 7.38 (d, 2H, J = 3.0 Hz), 7.38 -7.17 (m, 1H), 7.06-6.46 (m, 7H), 3.90 (s, 3H), 3.81 (s, 6H), 3.79 (s, 6H)

HPLC (reversed): Rt. (Min) = 4.82

MS (APCI, m / z): 558 (M + 1) + Example 409: 2,5-Dimethoxybenzaldehyde N- [6- {2-[(2,5-dimethyloxyphenyl) methylidene] hydrazino } -2- (2-Methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 5.05 MS (APCI, m / z): 572 (M + 1) + Example 410: 5-Methoxy-tridannone N- {2- (2-methoxyanilino) -6- [2- (5-methoxyindand-1-ylidene) ) Hydrazino] -4-pyrimidinyl} hydrazone

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρι: 9.43 (s, 2H), 8.77 (d, 1H, J = 7.8), 7.63 (d, 2H), 7.01-6.89 (m, 8H), 6.48 (s, 1H), 3.88 (s, 3H), 3.80 (s, 6H)

 HPLC (reversed): Rt. (Min) = 5.05

MS (APCI, m / z): 550 (M + l) +. Example 411: 2,2,3-Dimethoxybenzaldehyde [6- {2-[(2,3-dimethoxyphenyl) methylidene] hydrazino} -2- (2-methoxy-5-methylanilino) -4-pyrimidinyl] Hydrazone

 HPLC (reversed): Rt. (Min) = 4.82

MS (APCI, m / z): 572 (M + 1) + EXAMPLE 412: 5,6-Dimethoxy-1-indanone N-[6- [2- (5,6-dimethoxyindan-triylidene) hydrazino] -2- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

¾-Band R spectrum (270 MHz, DMS0-d ₆ ) «5ppm: 9.35 (s, 2H), 8.78-8.75 (m, 1H), 7.28-7.22 (m, 3H), 6.98-6.91 (in, 5H ), 6.50 (s, 1H), 3.89 (s, 3H), 3.82 (s, 6H), 3.81 (s, 6H), 3.00-2.96 (m, 4H), 3.95-3.91 (m, 4H)

HPLC (reversed): Rt. (Min) = 4.74

MS (APCI, m / z): 610 (M + 1) + Example 413: 5-methoxy-1-indanone N- [6- [2- (5-methoxyindan-triylidene) hydrazino] -2-- (2-Methoxy-5_methylanilino) -4-pyrimidinyl] hydrazone

'Η-wake R spectrum (270 MHz, DMSO- d ₆ ) 5ppm: 9.41 (s, 2H), 8.55-8.53 (m, 1 H), 7.65-7.60 (m, 2H), 6.99-6.84 (m, 6H), 6.70-6.68 (m, 1H), 6.45 (s, 1H), 3.85 (s, 3H), 3.81 (s, 6H ), 3.04-3.07 (m, 4H), 2.93-2.90 (m, 4H), 2.23 (s, 3H)

 HPLC (reversed): Rt. (Min) = 5.25

MS (APCI, m / z): 56 (Mil) + Example 414: 5,6-Dimethoxy-1-indanone N- [6- [2- (5,6-dimethoxyindane-1-ylidene) hydrazino]- 2- (2-Methoxy-5-methylanilino) -4-pyrimidinyl] HPLC (reversed): Rt. (Min) = 4.79

MS (APCI, m / z): 624 (Mil) + Example 15: Methyl 4-({2- [2-anilino-6- (2-{[4- (methoxycarbonyl) phene trifluoroacetate]

-Band R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 8.23 (s, 2H), 8.07 (d, 4H, J = 8.2 Hz), 7.91-7.82 (m 6H), 7.33-7.8 (m, 2H), 3.89 (2, 6H)

HPLC (reversed): Rt. (Min) = 4.97

MS (APCI, m / z): 524 (M + l) +. Example 16: 2,3-Dimethoxybenzaldehyde N- (2-anilino-6- {2-[(2,3-dimethoxyphenyl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone trifluoroacetate

[H - negation R spectrum _{(270 MHz, DMS0 - d 6} ) δρριη: 8.47 (s, 2H), 7.81-7.74 (m, 2 H), 7.55-7.03 (m, 10H), 3.85 (s, 6H), 3.81 (s, 6H)

HPLC (reversed): Rt. (Min) = 4.60

MS (APCI, m / z) : 528 (M + l) + 0 Example 417: 2, 5-dimethyl de N - (2-Anirino one 6- {2 - [(2, 5 - di Methoxyphenyl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

'H-NMR spectrum _{(270 MHz, DMSO- d 6)} δρριιι: 10.76 (s, 2H), 8.78 (s, 1H), 8.44 (s, 2H), 7.87 (d, 2H, J = 8.1 Hz), 7.38 (d, 2H, J = 3.0 Hz), 7.30- 7.17 (m, 2H), 7.05-6.86 (m, 5H), 6.45 (s, 1H), 3.80 (s, 6H), 3.79 (s, 6H)

 HPLC (reversed): Rt. (Min) = 4.95

MS (APCI, m / z): 528 (M + l) +. Example 418: 1- (2-Chenyl) -triethanone N- (2-anilino-6- {2- [2- (2-Cenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

-丽 R spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 9.58 (s, 2H), 8.62 (s, 1H), 7.94 (m, 2H), 7.56-7.58 (m, 2H), 7.20-7.29 (m, 4H), 7.05-7.11 (ni, 2H), 6.86-6.88 (m, 1H), 6.54 (s, 1H)

HPLC (reversed): Rt. (Min) = 4.49

MS (APCI, m / z): 448 (M + l) + ₀ Example 419: 5-methoxy-1-indanone N- {2-anilino-6- [2- (5-methoxyindane-1-ylidene) ) Hydrazino] -4-pyrimidinyl} hydrazone

Ή -Awake R spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 9.11 (brs, 2H), 8.61 (brs, 1H), 7.91 (d, 2H, J = 7.3 Hz), 7.63 (d, 2H, J = (7.3 Hz), 7.25-7.23 (m, 2H), 6.96-6.87 (m, 5H), 6.46 (s, 1H), 3.81 (s, 6H), 3.09-3.07 (m, 4H), 2.94

-2.92 (m, 4H)

 HPLC (reversed): Rt. (Min)-5.28

MS (APCI, m / z): 520 (Mil) I Example 420: 5,6-Dimethoxy-1-indanone N- {2-anilino-6- [2- (5,6-dimethoxyxindan-1) -Ylidene) hydrazino] -4-pyrimidinyl} hydrazone

HPLC (reversed): Rt. (Min) = 4.85

MS (APCI, m / z): 580 (M + l) +. Example 421: N- [4- (tri {2- [6- (2- {1- [4- (acetylamino) phenyl] ethylidene} hydrazino) -2-anilino-4-pyrimidinyl] hydrazono} ethyl) phenyl] Acetamide

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) (5 pm: 10.10 (brs, 2H), 9.55 (brs, 2 H), 8.69 (brs, 1H), 7.96 (d, 2H, J = 8.2 Hz) , 7.81 (d, 4H, J = 8.7 Hz),

7.67 (d, 4H, J = 8.7 Hz), 7.25 (t, 2H, J = 7.1 Hz), 6.92-6.89 On, 1H),

6.60 (s, 1H), 2.31 (s, 6H), 2.09 (s, 6H)

HPLC (reversed): Rt. (Min) = 4.14

MS (APCI, m / z): 550 (M + l) +. Example 422: N- [4- (l- {2- [6- (2-U- [4_ (acetylamino) phenyl] ethylidene] hydrazino) -2- (2-methoxyanilino) -4-pyrimidinyl] hydrazono} ethyl ) Phenyl] acetamide

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρηι: 10.08 (brs, 2H), 9.82 (brs, 2 H), 8.85 (brs, 1H), 7.80 (d, 4H, J = 8.6 Hz) , 7.65 (d, 4H, J = 8.6 Hz), 7.34 (s, 1H), 7.02-6.91 (m, 3H), 6.62 (s, 1H), 3.90 (s, 3H), 2.31 (s, 6H), 2.09 (s, 6H)

HPLC (reversed): Rt. (Min) = 4.13

MS (APCI, m / z): 580 (M + 1) + Example 423: N- [4- (tri {2- [6- (2- {tri- [4- [acetylamino] phenyl] ethylidene} hydrazino)) -2- (2-Methoxy-5-methylanilino) -4-pyrimidinyl] hydrazono} ethyl) phenyl] acetoamide

麵 R spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 10.12 (s, 2H), 7.88-7.85 (m, 4H), 7.68-7.65 (m, 4H), 3.86 (s, 3H), 2.34 (s, 6H), 2.27 (s, 3H), 2.08 (s, 6H)

 HPLC (reversed): Rt. (Min) = 4.27

MS (APCI, m / z): 594 (M + 1) + Example 424: [4- (methylsulfonyl) phenyl] _1-N- [2-anilino-6- (2- {1- [4- (methylsulfonyl) phenyl] -4-pyrimidi

'.Eta. Li R spectrum _{(270 MHz, DMSO- d 6)} 6ppm: 9.90 (s, 2H), 8.77 (s, 1H), 7.

96-8.11 (m, 10H), 7.25-7.31 (m, 2H), 6.92 (m, 1H), 6.65 (s, 1H), 3.26

(s, 6H), 2.40 (s, 6H)

 HPLC (reversed): Rt. (Min) = 4.18

 MS (APCI, m / z): 592 (M + 1) + Example 25: 1- [4- (methylsulfonyl) phenyl] -triethanone N- [2- (2-methoxyanilino) -6- (2 -U-[4- (Methylsulfonyl) phenyl] ethyline} hydrazino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 4.12

MS (APCI, m / z): 622 (M + l) + ₀ Example 426: 1- [4_ (methylsulfonyl) phenyl] -1 -ethanone N- [2- (2-methoxy-5-methylanilino) -6- (2-U- [4- (methylsulfonyl) phenyl] ethylidene} hydrazino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 4.24

MS (APCI, m / z): 636 (M + 1) I Example 427: 6,7-dimethoxy-3,4-dihydro-1 (2H) -naphthalenone N- (2-anilino-6- {2 -[6,7-dimethoxy-3,4-dihydro_1 (2H) -naphthalenylidene] hydrazino}-4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 4.82

MS (APCI, m / z): 608 (M + 1) + Example 428: 5-hydroxy-2-nitrobenzaldehyde N- [6- {2-[(5-hydroxy C2-Nitrofenino_2- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 4.85

MS (APCI, m / z): 560 (M + 1) + Example 429: 5-Hydroxy-2-nitrobenzaldehyde N- [6- {2-[(5-hydroxy-2-nitrophenyl) Methylidene] hydrazino} _2- (2-methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 5.27

MS (APCI, m / z): 574 (M + 1) + Example 430: 6-chloro-1,3_benzodioxole-5-propaldehyde -C2-T Nirino-6- {2_ [(6-Chloro-1,3-benzodioxoyl-5-yl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.53

MS (APCI, m / z) : 564 (M + l) + 0 Example 431: 6_ black hole - 1, 3-benzodioxolyl O benzodioxole - 5- force Lupo aldehyde N-[6- {2 one [ (6-chloro-1,3-benzodioxoyl-5-yl) methylidene] hydrazino} -2- (2-methoxyanilino) -4-pyrimigel] hydrazone

HPLC (reversed): Rt. (Min) = 5.91

MS (APCI, m / z): 594 (M + 1) + Example 32: 6-chloro-1,3-benzodioxole-5-hydroxylaldehyde N-[6- -2-[( 6-chloro-1,3-benzodioxole-5-yl) methylidene] hydrazino} -2- (2-methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 6.15

MS (APCI, m / z): 608 (M + 1) + Example 433: 3-hydroxy-4-nitrobenzaldehyde N- (2-anilino-6- {2 _ [(3-hydroxy-4-nitrophenyl) methylidene] hydrazino} -4_pyrimidinyl) hydrazone

 HPLC (reversed): Rt. (Min) = 6.26

MS (APCI, m / z): 530 (M + 1) + Example 434: 3-hydroxy-4-nitrobenzaldehyde N- [6- {2-[(3-hydroxy-4-ditrophenyl) Methylidene] hydrazino} _2- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 5.12

 MS (APCI, m / z): 560 (M + 1) +

 Example 435: 3-Hydroxy-4-nitrobenzaldehyde N- [6- {2-[(3-hydroxy-4-nitrophenyl) methylidene] hydrazino} -2- (2-methoxy-5-methylanilino) -4-Pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 5.65

 MS (APCI, m / z): 574 (M + l) +. Example 436: 4- (Jethylamino) -2-hN- [2-anhylino-6- (2-{[4- (Jethylamino) -2-hydroxyphene :: l] methylidene} hydrazino) -4- Pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 6.55

ト キシァニリノ）- 4 -ピリミジニリレ]ヒドラゾン MS (APCI, m / z): 582 (Mil) +

Toxianilino) -4-Pyrimidinylile] hydrazone

HPLC (reversed): Rt. (Min) = 5.97

MS (APCI, m / z): 612 (M + 1) + Example 438: 4- (Jethylamino) -2-hydroxybenzaldehyde N- [6- (2-{[4- (Jethylamino) -2-hydroxyphenyl] methylidene} hydrazino) -2- (2-methoxy-5 -Methylanilino) -4-pyrimidinyl] hydrazone

MS (APCI, m / z): 626 (Mil) + Example 439: 2-chloro-6-fluorobenzaldehyde N-(2-anilino-6- {2-[(2-chloro-6- Fluorophenyl) methylidene] hydrazino}-4-pyrimidyl) hydrazone

 HPLC (reversed): Rt. (Min) = 5.87 '

MS (APCI, m / z): 512 (M + 1) + Example 440: 2_chloro opening-6-fluorobenzaldehyde N- [6- {2-[(2-chloro-6_fluorophenyl) methylidene] ] Hydrazino} -2- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 5.93

MS (APCI, m / z): 542 (Μ + 1) +. Example 441: 2_clo mouth-6-fluorobenzaldehyde N- [6- {2-[(2-clo mouth_6-fluorophenyl) methylidene] hydrazino} -2- (2-methoxy-5-methylanilino) -4-Pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 6.29

MS (APCI, m / z): 556 (M + 1) + Example 442: 2_clo mouth-5-nitrobenzaldehyde N- (2-anilino-6- {2-[(2 -clo mouth- 5-nitrophenylyl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριη: 11.39 (s, 2H), 9.01 (s, 1H), 8.72 (d, 2H, J-2.9 Hz), 8.53 (s, 2H), 8.19 (dd , 2H, J = 2.9 Hz, 8.8 Hz, 7.81-7.91 (m, 4H), 7.28 (t, 2H, J = 7.4 Hz), 6.93 (t, 1H, J = 7.4 H z), 6.56 (brs, 1H)

 HPLC (reversed): Ri. (Min) = 6.19

 MS (APCI, m / z): 566 (Mil) + Example 443: 2-Mouth mouth-5_Mouth benzaldehyde N- [6- {2- [(2-Mouth mouth-5- Phenyl) methylidene] hydrazino} -2- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

 HPLC (reversed): Rt. (Min) = 6.19

MS (APCI, m / z): 596 (M + 1) + Example I | 444: 2-D mouth- 5-D benzaldehyde N_ [6- {2-[(2-D mouth -5-Nito-Methylphenyl) methylidene] hydrazino} _2- (2-methoxy-5_methylanilino) -4-4-Primidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 6.61

MS (APCI, m / z): 610 (M + 1) + Example 445: 5-chloro-2- nitrobenzaldehyde N_ (2-anilino-6- {2- [(5-chloro- 2-nitrophenyl) methylidene] hydrazino} -4_pyrimidinyl) hydrazone

 HPLC (reversed): Rt. (Min) = 6.63

MS (APCI, m / z): 566 (M + l) + ₀ Example 446: 5-Methoxy-2-benzaldehyde N- [6- {2-([5-M -2-Nito-mouth phenyl) methylidene] hydrazino}-2- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

 HPLC (reversed): Rt. (Min) = 6.66

MS (APCI, m / z): 596 (M + 1) + Example 447: 5-Mouth mouth-2-2-Mouth benzaldehyde 1 ^-[6- {2-[(5-Mouth mouth -2-two 6

173 Mouth phenyl) methylidene] hydra 1 dinote 2- (2-methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

 HPLC (reversed): Rt. (Min) = 6.94

 MS (APCI, m / z): 610 (M + 1) + Example 448: 2,4-difluorobenzaldehyde N- (2-anilino-6- {2-[(2,4-difluorophenyl) Methylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.38

MS (APCI, m / z): 480 (M + 1) + Example 449: 2,4-Difluorobenzaldehyde N- [6- {2-[(2,4-difluorophenyl) methylidene] hydrazino} -2- (2-Methoxyanilino) -4-pyrimidinyl] hydrazone

 HPLC (reversed): Rt. (Min) '= 5.32

MS (APCI, m / z): 510 (M + 1) + Example 450: 2,4-N- [6- [2-[(2,4-difluorophenyl) methylidene] hi-2- ( 2-Methoxy-5-methylanilino) -4-pyrimidi HPLC (reversed): Rt. (Min) = 5.67

MS (APCI, m / z): 524 (M + l) +. Example 51: 2,6-Difluoro N- (2-anilino_6- {2-[(2,6-difluorophenyl) methylidene] hi 4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.14

MS (APCI, m / z): 480 (M + 1) + Example 452: 2,6-difluorobenzaldehyde N- [6- [2-[(2,6-difluorophenyl) methylidene] hydrazinoto 2- (2-Methoxyanilino) -4-pyrimidinyl] hide Razon

'H-NMR spectrum (270 MHz, DMSO-d ₆ ) δρριη: 11.13 (s, 2H), 8.53-8.57 (s, 1H), 8.24 (s, 2H), 7.38-7.50 (m, 3H), 7.18- 7.26 (m, 4H), 6.94-7.06 (m, 3H), 6.50 (s, 1H)

HPLC (reversed): Rt. (Min) = 5.20

MS (APCI, m / z): 510 (M + 1) + Example 453: 2,6-difluorobenzaldehyde N- [6- {2-[(2,6-difluorophenyl) methylidene] hydrazino} _2- (2-Methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

 HPLC (reversed): Rt. (Min) = 5.49

MS (APCI, m / z): 524 (M + 1) + Example 454: 5-Fluoro-indanone N_ {2-anilino-6- [2_ (5_fluoroindan-1-ylidene) hydrazino] -4 -Pyrimidinyl} hydrazone

HPLC (reversed): Rt. (Min) = 5.80

MS (APCI, m / z): 496 (M + 1) + Example 55: 5-Fluoro-1-indanone N-[6- [2- (5-Fluoroindan-triylidene) hydrazino] -2- (2-Methoxyanilino) -4-pyrimidinyl] hydrazone HPLC (reversed): Rt. (Min) = 5.36

MS (APCI, m / z) : 526 (M + l) + 0, Example 456: 5 - Furuoro - 1- indanone N- [6 - [2 - ( 5- Furuoroindan - Bok ylidene) hydrazino] - 2 -(2-Methoxy-5-methylanilino) -4-pyrimidinyl] hydra

HPLC (reyersed): Rt. (Min) = 5.63

MS (APCI, m / z): 540 (M + 1) + Example 457: 6-Methyl-1-indanone N- {2-anilino-6- [2- (6-methylindan-triylidene) hydrazino] -4-pyrimidinyl} hydrazone

HPLC (reversed): Rt. (Min) = 6.23

MS (APCI, m / z): 488 (M + 1) + EXAMPLE 458: 6-methyl-1-indanone N- {2- (2-methoxyanilino) -6- [2- (6-methylindane-1 -Ylidene) hydrazino] -4-pyrimidinyl} hydrazone

HPLC (reversed): Rt. (Min)-5.77

MS (APCI, m / z): 518 (M + 1) + EXAMPLE 459: 6-methyl-triindanone N- {2- (2-methoxy-5-methylanilino) -6- [2- (6-methyl Indane-1-ylidene) hydrazino] -4-pyrimidinyl} hydrazone HPLC (reversed): Rt. (Min) = 6.13

MS (APCI, m / z): 532 (M + 1) + Example 460: 3-Methyl-1-indanone N- {2-anilino-6- [2- (3-methylindan-triylidene) hydrazino] -4-pyrimidinyl} hydrazone

HPLC (reversed): Rt. (Min) = 5.74

MS (APCI, m / z): 488 (M + l) +. Example 461: 3Methyl-1-indanone N- {2- (2-methoxyanilino) -6- [2- (3-methylindan-1-ylidene) hydrazino] -4-pyrimidinyl} hydrazone

HPLC (reversed): Rt. (Min) = 5.57

MS (APCI, m / z): 518 (M + 1) + Example 462: 3-Methyl-1-indanone N- {2- (2-methoxy-5-methylanilino) -6- [2- (3- Methylindane-1-ylidene) hydrazino] -4-pyrimigel} hydrazone HPLC (reversed): Rt. (Min)-5.98

MS (APCI, m / z): 532 (M + 1) +. Example 463: 5-Kuguchiguchi-Tridandanone N- {2-anilino-6-[2- (5-cloguchiloindan-1-ylidene) hydrazino] -4-pyrimidinyl} hydrazone

HPLC (reversed): Rt. (HI in) = 6.75

MS (APCI, m / z): 528 (Mil) + Example 464: 5-Chloro-tridandanone N- [6- [2- (5-Couroloindane-triylidene) hydrazino] -2- (2- Methoxyanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 6.15

MS (APCI, m / z): 558 (M + 1) + Example 465: 5-Kuguchi-Toindanone N- [6- [2_ (5-Kuloindan-toylidene) hydrazino] -2- (2 -Methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone HPLC (reversed): Rt. (Min) = 6.57

MS (APCI, m / z): 572 (M + l) +. Example 466: 1,3-Benzodoxyl-4-l-propanolaldehyde N- (2-anilino-6- {2- [1,3-benzodioxol-4-ylmethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone

 HPLC (reversed): Rt. (Min) = 4.74

MS (APCI, m / z): 496 (M + 1) + Example 467: 1,3-benzodioxole-4-carpaldehyde N- [6- {2- [1,3-benzodioxol- 4-ylmethylidene] hydrazino} -2- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

'Η-image R spectrum (270 MHz, DMS0-d ₆ ) (5 ppm: 11.01 (s, 2H), 8.52-8.56 (m, 1H), 8.16 (s, 2H), 7.26-7.34 (m, 3H), 6.92-7.05 (m, 7H), 6.51 (s, 1H), 6.15 (s, 4H), 3.90 (s, 3H)

HPLC (reversed): Rt. (Min) = 4.72 MS (APCI, / z): 526 (M + 1) + Example 468: 1,3-benzodioxole- 4-carboxaldehyde N- [6- {2- [1, 3-benzodioxol- 4-ylmethylidene] hydrazino}-2- (2-methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 8.25 (brs, 2H), 7.22-7.38 (m, 2H), 6.92-7.07 (m, 7H), 6.15-6.21 (m, 5H), 3.86 (s, 3H), 2.33 (s, 3H) HPLC (reversed): Rt. (Min) = 5.06

MS (APCI, m / z): 540 (M + 1) + Example 469: 2,3-Difluorobenzaldehyde N- (2-anilino_6-{2-[(2,3-difluorophenino) ■ -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.60

MS (APCI, m / z): 480 (M + 1) + Example 470: 2,3-: N- [6- {2-[(2,3-difluorophenyl) methylidene] hydrazino} -2 -(2-Methoxyanilino) -4-pyrimidinyl] hydrazone

 HPLC (reversed): Rt. (Min) = 5.42

MS (APCI, m / z): 510 (M + l) + _o Example 71: 2,3-difluorobenzaldehyde N- [6- {2-[(2,3-difluorophenyl) methylidene] hydrazino } -2-(2-Methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

 HPLC (reversed): Rt. (Min) = 5.81

MS (APCI, m / z): 524 (M + 1) + Example 472: 4-chloro-2-nitronitrobenzaldehyde N- (2-anilino-6- {2-[(4-chloro- 2-nitrophenyl) methylidene] hydrazino}-4-pyrimidinyl) hydrazo N

 HPLC (reversed): Rt. (Min) = 6.79

MS (APCI, m / z): 566 (M + 1) + Example 473: 4- ク 口 口 -2_ 二 ト ロ robenzaldehyde N- [6- {2-[(4- ク 口 口 -2 -Nito-mouth phenyl) methylidene] hydrazino 2- (2-methoxyanilino) -4- 4-pyrimidyl] hydrazone

 HPLC (reversed): Rt. (Min) = 6.61

 MS (APCI, m / z): 596 (M + 1) + · Example 474: 4- -2-Nitrobenzaldehyde N- [6- {2-[(4- ク ロ -2-nitro Mouth phenyl) methylidene] hydrazino} -2- (2-methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 6.94

MS (APCI, m / z): 610 (M + 1) + Example 475: 6,7-dimethoxy-3,4-dihydro_1 (2H). -Naphthalenone N-[6- {2--[6,7 -Dimethoxy-3,4-dihydro-1 (2H) -naphthalenylidene] hydrazino} -2- (2-methoxydiarino) -4--4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Rain) = 4.87

MS (APCI, m / z): 638 (M + l) +. Example 76: 6,7-dimethoxy-3,4-dihydro-1 (2H) -naphthalenone- [6- {2- [6,7-dimethoxy-3,4-dihydro-1 (2 © -naphthalenylidene] hydrazino) 2- (2-Methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 5.10

MS (APCI, m / z): 652 (M + 1) + EXAMPLE 477: 7-Nitro-3,4-dihydro-1 (2H) -naphthalenone N- (2-anilino-6- {2 05216

179

-[7-Nitro-3,4-dihydro-1 (2H) -naphylrenylidene] hydrazino} -4-pyrimidinyl) hydrazone

 HPLC (reversed): Rt. (Min) = 5.39

MS (APCI, m / z): 578 (M + 1) + Example 478: 4_butoxybenzaldehyde N- (2-anilino-6- {2-[(4-butoxyphenyl) methylidene] hydrazino} -4- Pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 6.27

MS (APCI, m / z): 552 (M + 1) + Example 479: 4_butoxybenzaldehyde N- [6- {2-[(4-butoxyphenyl) methylidene] hydrazino} -2- (2-methoxyanilino ) -4-Pyrimidinyl] hydrazone HPLC (reversed): Rt. (Min) = 6.27

MS (APCI, m / z): 582 (M + 1) + Example 480: 4-butoxybenzaldehyde N- [6- {2-[(4-butoxyphenyl) methylidene] hydrazino}-2- (2-methoxy -5-methylanilino) -4-pyrimidinyl] h

HPLC (reversed): Rt. (Min) = 6.90

MS (APCI, m / z) : 596 (M + l) + 0 Example 481: Bok (3 Metokishifue sulfonyl) - 1 - ethanone N-(2-Anirino - 6_ {2 - [Bok (3 - methoxy Phenyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.00

MS (APCI, m / z): 496 (M + 1) + Example 482: tri (3-methoxyphenyl) -triethanone N- (2- (2-methoxyanilino) -6- {2- 3-Methoxyphenyl) ethylidene] hydrazino} -4-Pyrimigel) hydrazone HPLC (reversed): Rt. (Min) = 5.17

 MS (APCI, m / z): 526 (M + 1) + 'Example 483: tri (3-methoxyphenyl) -1-ethanone N- (2- (2-methoxy-5-methylanilino) -6 -{2- [1- (3-Methoxyphenyl) ethylidene] hydrazino} _4-pyrimidinyl) hydrazone

 HPLC (reversed): Rt. (Min)-5.26

MS (APCI, m / z): 540 (M + 1) + Example 484: 1,3-benzodioxol-5-hydroxypropyl N- (2-anilino-6- {2- [1,3- Benzodioxol-5-ylmethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 HPLC (reversed): Rt. (Min) = 4.61

MS (APCI, m / z): 496 (Mil) + Example 485: 1,3-benzodioxole-5-hydroxyl-aldehyde- [6- {2- [1,3-benzodioxol- 5-ylmethylidene] hydrazino} -2- (2-methoxyanilino) -4-pyrimidinyl] hydrazone.

HPLC (reversed): Rt. (Min) = 4.66

MS (APCI, m / z): 526 (M + l) +. Example 486: 1,3-Benzodoxyl-5-carbaldehyde N_ [6- {2- [1,3-benzodioxol-5-ylmethylidene] hydrazino} -2- (2-methoxy-5-methylani Reno) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 4.92

MS (APCI, m / z) 540 (M + 1) + Example 487: 6-Nitro-1,3-benzodioxol-5-hydroxypropyl N- (2-anilino-6- {2 _ [( 6-Nitro-1,3-benzodioxol-5-ylyl) methylidene] hydra Dino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.26

MS (APCI, m / z): 586 (M + 1) + Example 488: 6-Nitro-1,3-benzodioxoyl-5-hydroxypropyl N- (2- (2-methoxyanilino) -6- {2-[(6-Nitro-1,3-benzodioxol-5-yl) methylidene] hydrazino} -4-pyrimidinylyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.08

MS (APCI, m / z): 616 (M + 1) + Example 489: 6-nitro-1,3-benzodioxole-5-carbaldehyde N- (2- (2-methoxy-5_ Methylanilino) -6- {2-[(6-nitro-1,3-benzodioxol-5-yl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.45

MS (APCI, m / z): 630 (M + 1) + Example 490: 6-methoxy-1-indanone N- {2-anilino-6- [2- (6-methoxyindan-1-ylidene) hydrazino ] -4-Pyrimidinyl} hydrazone

'H-NMR spectrum (270 MHz, DMSO-d ₆ ) 5 pm: 9.33 (s, 2H), 8.62 (s, 1H), 7.90-7.93 (m, 2H), 7.20—7.31 On, 6H), 6,88-6.98 (m, 3H), 6.61 (s, 1H), 3.8 2 (s, 6H), 2.97-3.01 (m,,, 8H)

HPLC (reversed): Rt. (Min) = 5.40

MS (APCI, m / z): 520 (M + l) + _o Example 491: 4,5-dimethoxy-2-nitrobenzaldehyde N- (2-anilino-6- {2-[(4, 5 -dimethoxy-2-nitropheni) 1g, no, hydrazino} -4-pyrimidini M hydrazone

 HPLC (reversed): Rt. (Min) = 4.73

MS (APCI, m / z): 618 (M + 1) + Example 492: 6-Nitro-1,3-benzodioxole-5-propanolaldehyde N- (2-anilino-6- {2-[(6-dito-1,3-benzodioxol) Oxol-5-yl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 4.91

MS (APCI, m / z): 586 (M + 1) + Example 493: 4,5-dimethoxy-2-nitrobenzaldehyde N- [6- {2-[(4,5-dimethoxy-2 -Ditrophenyl) methylidene] hydrazino}-2- (2-methoxyanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 4.70

MS (APCI, m / z): 648 (M + 1) + EXAMPLE 494: 6-nitro-1,3-benzodioxoyl-5-carpaldehyde N- (2_ (2-methoxyanilino) -6- {2 -[(6-Nitro-1,3-benzodioxol-5-yl) methylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 4.85

MS (APCI, m / z): 616 (M + 1) + Example 495: 4,5-dimethoxy-2-nitrobenzaldehyde N- [6- {2-[(4,5-dimethyloxy- 2-Nittophenyl) methylidene] hydrazino} -2- (2-Methoxy-5-methyla2rino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 4.94

MS (APCI, m / z): 662 (M + l) +. Example 496: 6-Nitro-1,3_benzodioxol-5-propanolaldehyde N- (2- (2-methoxy-5-methylanilino) -6- {2 _ [(6_nitro-1, 3-benzodioxole _5-yl) metylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.09 05216

183

MS (APCI, m / z): 630 (M + 1) +

 Example 497: 4-Methyl-3,4-dihydro-1 (2H) -naphthalenone N- (2- (2-methoxy-5-methylanilino) -6_ {2- [4-methyl-3,4-dihydro- 2H) -Naphthalenylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 6.07

MS (APCI, m / z): 560 (Mil) + Example 498: 5-methoxy-3,4-dihydro-1 (2H) -naphthalenone N- (2- (2-methoxyanilino) -6- {2 -[5-Methoxy-3,4-dihydro-1 (2H) -naphthalenylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.55

MS (APCI, m / z): 578 (M + 1) + Example 499: 5-methoxy-3,4-dihydro-1 (2H) -naphthorenenone N- [6- {2- [5-meth Xy-3,4-dihydro-1 (2H) -naphthalenylidene] hydrazino} -2- (2-methoxy-5-methylanilino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 5.87

MS (APCI, m / z): 592 (M + 1) + Example 500: 6-methoxy-3,4-dihydro-1 (2H) -naphthalenone N- (2- (2-methoxyanilino) -6- {2_ [6-Methoxy-3,4-dihydro-1 (2H) -naphylrenylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.87

MS (APCI, m / z): 578 (M + l) +. Example 501: 6-Methoxy-3,4-dihydro-1 (2H) -naphthalenone N- [6- {2- [6-methoxy-3,4-dihydro_1 (2H) -naphthalenylidene] hydrazino} -2 -(2-Methoxy-5-methylanilino)-4-Pirimigel] hydrazone

HPLC (reversed): Rt. (Min) = 5.55 JP03 / 05216

184

MS (APCI, m / z): 592 (M + 1) + EXAMPLE 502: 7-methoxy-3,4-dihydro-1 (2H) -naphthalenone N- (2- (2-methoxyanilino) -6- {2- [7-Methoxy-3,4-dihydro-1 (2H) -naphthalenylidene] hydrazino} -4-pyrimidinylyl) hydrazone

MS (APCI, m / z): 57 Australia 1) + Example 503: 4-Methyl-3,4-dihydro-1 (2H) -naphthalenone N- (2-anilino-6_ {2-[4-methyl- 3,4-dihydro-1 (2H) -naphthalenylidene] hydrazino} -4-pyrimidini

HPLC (reversed): Rt. (Min) = 6.09

MS (APCI, m / z): 516 (M + 1) + Example 504: 5-Methoxy-3,4-dihydro-1 (2H) -naphthorenone N- (2-anilino-6- {2- [5-Methoxy-3,4-dihydro_1 (2H) -naphthalenylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.76

MS (APCI, m / z): 548 (M + 1) + Example 505: 7-methoxy-3,4-dihydro-1 (2H) -naphthalenone N- (2-anilino-6- {2- [7 -Methoxy-3,4-dihydro-1 (2H) -naphylrenylidene] hydrazino 4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.67

MS (APCI, m / z) : 548 (M + l) + 0 Example 506: 7-nitro - 3, 4 - dihydro - 1 (2H) - -naphthalenone N- (2- (2- Metokishia two Reno) - 6- {2- [7-Nitro-3,4-dihydro-1 (2H) -naphthalenylidene] hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 5.58 MS (APCI, m / z) 608 (M + 1) + Example 507: 7-Nitro-3,4-dihydro-1 (2H) -naphthalenone N- (2- (2-methoxy-5-methylanilino) -6- {2- [7-Nitro-3,4-dihydro-1 (2H) -naphylrenylidene] hydrazino 4-pyrimidinyl) hydrazone

HPLC (reversed) Rt. (Min) = 5.72

MS (APCI, m / z) 622 (M + l) † Example 508: N- [5- {2- [6- {2- [6- (acetylamino) -3,4-dihydro-1 (2H) -Naphthylenylidene] hydrazino} _2- (2-methoxyanilino) -4-pyrimidinyl] hydrazono}-7,8-dihydro-2 (6H) -naphthalenyl] acetamide

HPLC (reversed) Rt. (Min) = 4.30

MS (APCI, m / z) 632 (M + l) + Example 509

 1- (4-pyridinyl) -1-ethanone N- (2- (2,4-dimethylanilino) -6_ {2- [1_ (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 2- (2,4-Dimethylanilino) -4,6-dihydrazinopyrimidine (0.1 IMOI) was dissolved in dioxane (1 ml), and 4-acetylpyridine (0.66 ml, 0.1 mmol) was added. Stirred for 18 hours. After distilling off the solvent under reduced pressure, a solution of ethyl acetate-getyl ether was added to the residue and suspended. The desired product was obtained by pulverizing the precipitated solid and collecting the solid by filtration.

Ή-丽 R spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 10.20-10.14 (brs, 1H), 8.66 (dd, 4H, J = 1.3 Hz, 4.8 Hz), 7.81 (dd, 4H, J = 1.3 Hz, 4.8 Hz), 7.61-7.5 9 On, 1H), 7.02-7.00 (m, 2H), 6.65 (s, 1H), 2.32 (s, 6H), 2.28 (s, 3H), 2.23 (s, 3H)

HPLC (reversed) Rt. (Min) = 3.04

MS (APCI, ra / z) 466 (M + l) +. Thereafter, the same reaction as in Example 509 was carried out, and the product was purified to obtain the desired compounds of Examples 510 to 547. Example 510: 1- (4-Pyridinyl) -1-ethanone N- (2- (2-chloroanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

'H-NMR spectrum (270 MHz, CD30D, TMS) d 8.78 (d, 4H, J = 6.6 Hz), 8.33 (d, 4H, J = 6.6 Hz), 8.26 (dd, 1H, J = 1.3 Hz , 5.3 Hz), 7.48 (d, 1H, J = 8.1 Hz), 7.40 (t, 1H, J = 7.1 Hz), 7.18 (t, 1H, J = 7.1 Hz), 6.93 (s, 1H), 2.47 ( s, 6H)

HPLC (reversed): Rt. (Min) = 3.10

MS (APCI, m / z): 472 (M + l) +. Example 511: 1_ (4_pyridinyl) -1'N- (2- (2-phenyl-ethylamino) -6- {2- [1_ (4-pyridinyl) eth-4-pyrimidinyl) hydrazone HPLC (reversed) : Rt. (Min) = 2.88

MS (APCI, m / z) : 466 (Μ + 1) + 0 Example 512: 1- (4-pyridinyl) - 1- N-(2 - Kishiruamino to consequent opening - 6- {2 - [1- ( 4-pyridinyl) ethi 1 -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 2.91

MS (APCI, m / z): 444 (M + D + Example 513: tri (4-pyridinyl) -triethanone N- (2- (2-methoxy-5-methylanilino) -6- {2- [ (4-pyridinylyl) ethylidene] hydrazino}-4-pyrimidinyl) hydra

¾-R spectrum (270 MHz, DMSO-d ₆ ) δ ρπι: 10.80-10.45 (brs, 2H), 8.70 (dd, 4H, J = 1.8 Hz, 4.5 Hz), 8.37 (brs-, 1H), 7.90 (dd, 4H, J = 1.8 Hz, 4.5 Hz), 6.95 (d, 1H, J = 7.8 Hz), 6.83 (m, 1H), 6.71 (s, 1H), 3.87 (s, 3H), 2.40 (s, 6H), 2.25 (s, 3H) HPLC (reversed): Rt. (Min) = 3.11

MS (APCI, m / z): 482 (M + 1) + Example 514: 1- (4-pyridinyl) -1 -ethanone N- (2-pyridyl-6- {2- [1-(4 -Pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Ή-NMR spectrum _{(270 MHz, DMSO- d 6)} άρριιι: 9.84 (s, 2H), 8.63 (d, 4H, J = 5.9 Hz), 7.75 (d, 4H, J = 5.9 Hz), 6.57 (s, 1H), 3.76-3.79 (m, 4H), 2.31 (s, 6H), 1.51-1.62 (m, 6H)

HPLC (reversed): Rt. (Min) = 2.89

MS (APCI, m / z): 430 (M + 1) + Example 515: 1-(4-pyridinyl) -thuetanone N- (2-pyrrolidyl-6_ {2_ [1- (4-pyridinyl) ethylidene) ] Hydrazino} -4-pyrimidinyl) hydrazone

HPLC (reversed): Rt. (Min) = 2.54

MS (APCI, m / z): 416 (M + l) +. Example 516: l- (4-pyridinyl) -toethanone N- (2- (2-ethoxyethoxylinylino) -6- {2- (1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidiel) hydrazone

Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) 5 pm: 10.28 (brs, 2H), 8.81 (m, 1H), 8.66 (d, 4H, J = 6.1 Hz), 7.79-7.83 (m, 5H) , 6.96-7.00 (m, 3H), 6.75 (s, 1H), 4.14 (q, 2H, J = 7.1 Hz), 2.36 (s, 6H), 1.417 (m, 3H)

HPLC (reversed): Rt. (Min) = 3.23

MS (APCI, m / z): 482 (M + 1) + Example 517: 1- (4-pyridinyl)-1-ethanone N- [6- {2- [1- (4-pyridinyl) ethylidene] Hydrazino} -2- (2-toluidino) -4-pyrimidinyl] hydrazone

HPLC (reversed): Rt. (Min) = 2.92

MS (APCI, m / z): 452 (M + 1) + Example 518: 1- (4-Pyridinyl) -toethanone N- (2- (3,5-dimethoxyanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone HPLC (reversed): Rt. (Min) = 2.95

MS (APCI, m / z): 498 (M + 1) + Example 519: 1 _ (4-pyridinyl) -1 -ethanone N- (2- [(4-methoxy [-1, Γ-biphenyl) ] -3-yl) amino] -1 6_ {2— [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) 5 ppm: 10.20 (s, 2H), 8.84-8.80 (m, 1H), 8.57 (d, 4H), 7.82-7.63 (m, 6H), 7.46-7.25 (m, 5H), 7.10 (m, 1H), 6,76 (s, 1H), 3.94 (s, 3H), 2.34 (s, 3H)

HPLC (reversed): Rt. (Min) = 3.61

MS (APCI, m / z): 544 (M + 1) + Example 520: 1- (4-Pyridinyl) -1-ethanone N- (2- [5- (tert-butyl) -2-methoxyanilino] -6-{2- [1_ (4-pyridinyl) ethylidene] hydrazino 4_pyrimidinile) hydrazone

! H-NMR spectrum _{(270 MHz, DMSO- d 6)} <5 pm: 10.01 (s, 2H), 8.63 (dd, 4H, J = 1.7 Hz, 4.6 Hz), 8.47 (brs, 1H), 7.77 (dd , 4H, J = 1.7 Hz, 4.6 Hz), 7.39 (s, 1H), 6.93-6.95 (m, 2H), 6.74 (s, 1H), 3.86 (s, 3H), 2.35 (s, 6H), 1.29 (s, 9H)

HPLC (reversed): Rt. (Rain) = 3.58

MS (APCI, m / z) : 524 (M + l) + 0 Example 521: 1- (4-pyridinyl) - 1_ ethanone N-(2-[2-methoxy - 5- (Torifuruo Romechiru) Anirino] -6- {2- [Ur (4-pyridinyl) ethylidene] hydrazino} _4 -Pyrimidinyl) hydrazone

Ή-NMR spectrum (270 MHz, D S0-d 6) δρριη: 10.10 (s, 2H), 8.63 (dd, 4H, J = 1.3 Hz, 4.8 Hz), 8.46 (m, 1H), 8.23 (s, 1H ), 7.76 (dd, 4H, J = 1.3 Hire 216

189

Hz, 4.8 Hz), 7.49-7.46 (m, 2H), 6.75 (s, 1H), 2.33 (s, 6H)

HPLC (reversed): Rt. (Min) = 3.41

MS (APCI, m / z) : 524 (M + l) + 0 Example 522: 1- (4 - pyridinyl) - Bok ethanone N-(2 - (2-Furuoroa two Reno) -6 - {2 - [ 1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone ΐ-NMR spectrum (270 MHz, DMS0-d ₆ ) <5 ppm: 10.10 (s, 1H), 8.64 (d, 4H, J = 6.1 Hz) ), 8.42 (t, 1H, J = 8.1 Hz), 7.77 (d, 4H, J = 6.1 Hz), 7.26-7.16 (m, 2H), 7.09-7.04 (m, 1H), 6.74 (s.1H) ), 2.34 (s, 6H)

HPLC (reversed): Rt. (Min) = 2.99

MS (APCI, m / z): 456 (M + l) +. Example 523: 1- (4-Pyridinyl) -1-ethanone N- (2- (2-fluoro-4-methylanilino) -6- {2- [1- [4- (4-pyridinyl) ethylidene] hydrazino 4-pyrimidinyl ) Hydra Zon

NMR-NMR spectrum (270 MHz, DMSO-d ₆ ) <5 ppm: 10.05 (s, 2H), 8.64 (dd, 4H, J = 1.5 Hz, 4.5 Hz), 8.15-8.12 (m, 1H), 7.77 (dd , 4H, J = 1.5 Hz, 4.5 Hz, 7.05 (d, 1H, 8.6 Hz, 11.9 Hz), 6.71 (s, 1H), 2.33 (s, 6H), 2.31 (s, 3H)

HPLC (reversed): Rt. (Min) = 3.11

MS (APCI, m / z): 470 (M + l) +. Example 524: tri (4-pyridinyl) -triethanone N- (2- (2,6-difluoroalilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone i-NMR spectrum (270 MHz, DMS0-d ₆ ) <5 m: 9.96 (brs, 2H), 8.63 (d, 4H, J = 4.9), 8.12 (brs, 1H), 7.74 (d, 4H, J = 4.9), 7.34-7.29 (ra, 1H), 7.1 8-7.12 (m, 2H), 6.70 (s, 1H), 2.29 (s, 6H)

HPLC (reversed): Rt. (Min) = 2.81

MS (APCI, m / z): 474 (M + 1) + 5216

190

Example 525: 1- (4-Pyridinyl) -1-ethanone N- [6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -2- (2,3,4_trifluorofluorinylino) -4-Pyrimidinyl] hydrazones

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 10.07 (s, 2H), 8.63 (dd, 4H, J = 1.7 Hz, 4.6 Hz), 8.31 (brs, 1H), 7.87-7.78 (m, 1H), 7.76 (dd, 4H, J = 1.7 Hz, 4.6 Hz), 7.32-7.25 (m, 1H), 6.73 (s, 1H), 2.33 (s, 6H)

HPLC (reversed): Rt. Din) = 3.20

MS (APCI, m / z): 492 (M + 1). Example 526: 1- (4-pyridinyl) -toethanone N- (2-anilino-6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

¾-NMR spectrum (270 MHz, DMS0-d ₆ ) 5ppra: 9.95 (s, 2H), 8.76 (s, 1H), 8.65 (dd, 4H, J = 1.5 Hz, 4.6 Hz), 7.96 (d, 2H, J = 7.7 Hz), 7.79 (dd, 4H, J = 1.5 Hz, 4.6 Hz), 7.27 (t, 2H, J = 8.2 Hz), 6.92 (t, 1H, J = 7.9 Hz), 6.70 ( s, 1H), 2.35 (s, 6H)

HPLC (reversed): Ri. (Min) = 2.84

MS (APCI, m / z): 438 (M + 1) +.

Elemental analysis _{(C 24 H 23 N 9)} '

Calculated values: C: 65.89; H: 5.30; N: 28.81

Found: C, 65.47; H, 5.34; N, 28.37. Example 527: 1- (4-Pyridinyl) -1-ethanone N- (2- (methylanilino) _6- {2- [tri (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Ή -image R spectrum (270 MHz, DMS0-d ₆ ) δ κ: 9.90 (s, 2H), 8.62 (d, 4H, J = 5.9 Hz), 7.74 (d, 4H, J = 5.9 Hz), 7.40- 7.36 (m, 4H), 7.19-7.17 (m, 1H), 6.67 (s, 1H), 3.52 (s, 3H), 2.30 (s, 6H)

HPLC (reversed): Rt. (Min)-2.81

MS (APCI, m / z): 452 (M + l) +. Example 528: 1- (4-Pyridinyl) -1 -ethanone N- (5-ethyl-2- (2-methoxyanilino) -6- {2- [2- (4-pyridinyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone

-NMR spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 9.19 (s, 2H), 9.09 (s, 1H), 8.65 (dd, 4H, J = 1,6 Hz, 4.9 Hz), 7.81 (dd, 4H, J = 1.6 Hz, 4.9 Hz), 7.0 5-6.93 (m, 4H), 3.90 (s, 3H), 2.98 (q, 2H, J = 6.9 Hz), 2.37 (s, 6H), 1.18 (t, 3H, J = 6.9 Hz)

HPLC (reversed): Rt. (Min) = 2.92

MS (APCI, m / z): 496 (M + 1) + Example 529: tri (4-pyridinyl) -triethanone N- (5-benzyl-2- (2-methoxyanilino) -6- {2- [4- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

'Η-Ran R spectrum (270 MHz, DMS0-d ₆ ) 6ppm: 9.09 (s, 2H), 8.52 (d, 4H, J = .8 Hz), 7.59 (d, 4H, J = 4.8 Hz), 7.32 -6.98 (in, 9H), 4.42 (s, 2H), 3.92 (s, 3H), 2.15 (s, 6H)

HPLC (reversed): Rt. (Min) = 3.33

 MS (APCI, m / z): 558 (M + 1) + '. Example 530: 1- (4-pyridinyl) -1 -ethanone N- (2- (3-pyridyl) _6- {2- [1 -(4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

'Η- 丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ρηι: 10.65 (s, 2H), 9.45 (s, 1H), 8.85-8.60 (m, 5H), 8.35 (brs, 1H), 8.10- 7.87 (m, 4H), 7.77-7.67 (m, 2H), 6.85 (s, 1H), 2.25 (s, 6H)

 HPLC (reversed): Rt. (Min) = 2.6

MS (APCI, m / z) : 439 (M + l) + 0 Example 531: 1- (4-pyridinyl) - Bok ethanone N-(2-(2 - Metokishianirino) - 5- menu 0305216

192 tyl-6- {2- [l- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydra

^! H -丽R spectrum _{(270 MHz, DMSO- d 6)} dm: 9.22 (s, 2H), 9.12-9.09 (m, 1

H), 8.65 (dd, 4H, J = 1.3 Hz, 4.8 Hz), 7.82 (dd, 4H, J = 1.3 Hz, 4.8 Hz), 7.01-6.94 (ηι, 4H), 3.91 (s, 3H), 2.37 (s, 6H), 2.33 (s, 3H)

HPLC (reversed): Rt. (Min) = 2.77

MS (APCI, m / z): 482 (M + 1) + Example 532: 1- (4-Pyridinyl) -1 -ethanone N-(2- (2-methoxyanilino) -5-propyl pent-6- {2- [1- (4-Pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Ή-丽 R spectrum (270 MHz, DMS0-d ₆ ) δρρηι: 8.89-8.86 (m, 1H), 8.75 (d, 4H), 7.98-7.93 (m, 4H), 7.13 (d, 2H, J = 2.1 Hz), 7.02-6.96 (m, 1H), 3.93 (s, 3H), 2.89 (t, 2H, J = 7.4 Hz), 1.64-1.56 (m, 2H), 1.00 (t, 3H, J = 7.4)

 HPLC (reversed): Rt. (Min) = 3.04

MS (APCI, m / z): 510 (M + 1) + Example 533: 1- (4-pyridinyl) -triethanone N-(2_ (2,5-difluoroalirino)-6- {2-[ (4-pyridinyl) ethylidene] hydrazino 4- (pyrimidinyl) hydrazone ¾- 丽 1 spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 10.21 (s, 2H9), 8.64 (d, 5H, J-5.9 Hz), 7.79 (d, 5H, J = 5.9 Hz), 7.22-7.31 (m, 1H), 6.75-6.81 (m, 2H), 2.35 (s, 6H)

HPLC (reversed): Rt. (Rain) = 7.43

MS (APCI, m / z): 474 (M + 1) + Example 534: 1-(4-pyridinyl)-1 · _ (2- (3,5-dimethoxyanilino). 6-{2- [1- (4-Pyridinyl) ethyshi-4-pyrimidinyl) hydrazone HPLC (reversed): Rt. (Min) = 3.39 MS (APCI, m / z): 4'98 (M + 1) + Example 535: 1- (4-pyridinyl) -1-ethanone N_ [6- {2- [1- (4_pyridinyl) ethylidene] ] Hydrazino} -2- (4-Toluidino) -4-pyrimidinyl] hydrazone

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) (5ppm: 9.95 (s, 2H), 8.65-8.67 (m, 5H), 7.79-7.83 (m, 6H), 7.07-7.10 (m, 2H) , 6.68 (s, 1H), 2.34 (s, 6H), 2.27 (s, 3H)

 HPLC (reversed): Rt. (Min) = 3.04

MS (APCI, m / z) : 452 (M + l) + 0 Example 536: 1 - (4-pyridinyl) one 1-ethanone N - (2-(2-Furuoro - 5 Mechiruaniri Roh) -6 - {2- [1- (4-Pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydra

Ή-NMR spectrum (270 MHz, DMSO- d ₆ ) 5ppm: 10.06 (brs, 2H), 8.64 (d, 4H, J = 6.1 Hz), 8.07 (m, 1H), 7.72-7.79 (m, 5H), 7.09 (dd, 1H, J-8.4 Hz, 11.0 Hz), 6.85 (m, 1H), 6.73 (s, 1H), 2.33 (s, 9H)

HPLC (reversed): Rt. (Min) = 3.10

MS (APCI, m / z): 470 (M + 1) + Example 537: tri (4-pyridinyl) -triethanone N- (2- (2,3-difluoroalirino) -6- {2- [ 1- (4-Pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριη: 10.11 (s, 2H), 8.66 (d, 4H, J = .6 Hz ), 8.11-8.16 (m, 2H), 7.78 (d, 4H, J = 4.6 Hz), 7.07-7.19 (m, 2 H), 6,76 (s, 1H)

 HPLC (reversed): Rt. (Min) = · 3.10

MS (APCI, m / z): 474 (M + 1) + Example 538: 1- (4-Pyridinyl)-1-ethanone N- (2- (4-Kuguchiguchi-2-fluoroanilino) -6- {2- [4- (4-pyridinyl) ethylidene] hydrazino 4-pyrimidinyl) hydra Dzong

_NMR spectrum _{(270 MHz, DMSO- d 6)} δρριη: 10.10 (s, 2H), 8.64 (d, 4H, J = 5.3 Hz), 8.37 (i, 1H, J = 8.5 Hz), 7.99 (s, 1H) , 7.77 (d, 4H, J = 5.3 Hz), 7.45 (dd, 1H, J = 2.0 Hz, 10.6 Hz), .7.23 (d, 1H, J = 8.8 Hz), 6.75 (s, 1H), 2.34 (s, 6H)

 HPLC (reversed): Rt. (Min) = 3.32

MS (APCI, m / z): 490 (M + 1) + Example 539: tri (4-pyridinyl) -1-ethanone N- (2- (2,3-dihydro-1H-indoletrito) Le) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Ή-NMR spectrum (270 MHz, DMSO- d ₆ ) 5ppm: 10.12 (s, 2H), 8.76 (d, 1H, J = 7.4 Hz), 8.65 (d, 4H, J = 6.1 Hz), 7.80 (dd, 4H, J = 1.5 Hz, 4.6 Hz), 7.19 (t, 2H, J = 7.1 Hz), 6.89 (t, 1H, J = 7.1 Hz), 6.73 (s, 1H), 4.22 (ί, 2H, J = 8.6 Hz), 3.15 (t, 2H, J = 8.6 Hz), 2.37

HPLC (reversed): Rt. (Min) = 3.33

MS (APCI, m / z): 464 (M + 1) + Example 540: l- (4_pyridinyl) -1-ethanone N- (2- (3,4-difluoroalirino) -6- {2 -[1- (4-Pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

'Η-band R spectrum (270 MHz, DMS0-d ₆ ) δ ppm: 10.03 (s, 2H), 9.09 (s, 1H),

8.64 (dd, 4H, J = 1.4 Hz, 4.7 Hz), 8.45 (brs, 1H), 7.80 (dd, 4H, J = 1.

4 Hz, 4.7 Hz), 7.55-7.45 (ni, 1H), 7.29 (q, 1H, J = 9.8 Hz), 6.71 (s, 1

H), 2.36 (s, 6H)

HPLC (reversed): Rt. (Min) = 3.18

MS (APCI, m / z): 474 (M + l) +. Example 541: 1- (4-pyridinyl) -1-N- (2- (2,4-difluoroalilino) -6- {2- [tri (4-pyridinyl τ: 1: r-4-pyrimidinyl) Hydrazone -NMR spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 10.03 (s, 2H), 8.64 (dd, 4H, J = 1.5 Hz, 4.6 Hz), 8.15 (q, 1H, J = 8.9 Hz), 7.95 (s, 1H), 7.76 (dd, 4H, J = 1.5 Hz, 4.6 Hz), 7.29 (t, 1H, J = 8.9 Hz), 7.05 (t, 1H, J = 8.9 Hz), 6.72 (s, 1H), 2.32 (s, 6H)

HPLC (reversed): Rt. (Min) = 3.06

MS (APCI, m / z): 474 (M + 1) + Example 542: 1- (4_pyridinyl) -1 -ethanone N- (2- (3-fluoroalirinino) -6- {2- [ 1- (4-pyridinyl) Echiriden] hydrazino} -4 - pyrimidinyl) hydrazone ¾ - field R spectrum _{(270 MHz, DMSO- d 6)} δρρπι: 10.03 (s, 2H), 9.07 (s, 1H), 8.64 (dd , 4H, J = 1.4 Hz, 4.7 Hz), 8.21 (d, 1H, J = 11.7 Hz), 7.81 (dd, 4H, J = 1.4 Hz, 4.7 Hz), 7.58 (d, 1H, J = 7.8 Hz) , 7.26 (q, 1H, J = 7.6 Hz), 6.75-6.63 (m, 2H), 2.36 (s, 6H)

HPLC (reversed): Rt. (Min) = 3.10

MS (APCI, m / z): 456 (M + 1) + Example 543: 1- (4-pyridinyl) -toluene non-N- (2- (4-fluoroalirino) -6_ {2-[ 1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone ¾-band R spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 9.96 (s, 2H), 8.85 (s, 1H), 8 65 (d, 4H, J = 6.1 Hz), 7.97 (dd, 2H, J = 5.1 Hz, 8.9 Hz), 7.78 (d, 4H, J = 6.1 Hz), 7.09 (t, 2H, J = 8.8 Hz) ), 6.70 (s, 1H), 2.35 (s, 6H) HPLC (reversed): Rt. (Min) = 3.01

MS (APCI, m / z): 456 (M + l) +. Example 544: Tri (4-pyridinyl) -1-ethanone N- (2- (5-chloro-2-fluoroalumino)-6- {2-[(tri (4-pyridyl) ethylidene] hydrazinoto 4- Pyrimidinyl) hydrazone.

-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 10.16 (s, 2H), 8.63 (d, 4H, J = 6.1 Hz), 8.55 (brs, 1H), 7.94 (s, 1H), 7.80 (dd , 4H, J = 1.2 Hz, 4.8 Hz), 7.29 (dd, 1H, J = 8.7 Hz, 10.7 Hz), 7.10-7.00 (m, 1H), 6.75 (s, 1H), 2.34 (s, 6H)

 HPLC (reversed): Rt. (Rain) = 3.29

MS (APCI, m / z): 490 (M + l) +. Example 545: 1_ (4-pyridinyl) -1-ethanone N- [6- {2- [tri (4-pyridinyl) ethylidene] hydrazino} -2- (2,4,5-tritrifluoroanilino) -4 -Pyrimidinyl] hydrazones

Ή-NMR spectrum (270 MHz, DMSO- d ₆ ) 6 ρπι: 10.16 (s, 2H), 8.70 (brs, 1H), 8.64 (dd, 4H, J = 1.5 Hz, 4.6 Hz), 7.97 (s, 1H ), 7.79 (dd, 4H, J = 1.5 Hz, 4.6 Hz), 7.65-7.53 (m, 1H), 6.74 (s, 1H), 2.34 (s, 6H)

HPLC (reversed): Rt. (Min) = 3.26

MS (APCI, m / z): 492 (M + l) +. Example 546: Tri (4-pyridinyl) -1-propanone N- (2-anilino-6- {2- [1- (4-pyridinyl) -pyrididene] hydrazino} -4-pyrimidinyl) hydrazone

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) άριη: 10.16 (s, 2H), 8.77 (m, 1H), 8.66 (d, 4H, J = 5.9 Hz), 7.98 (d, 2H, 7.8 Hz) ), 7.80 (d, 4H, J = 5.9 Hz), 7.29 (t, 2H, J = 7.8 Hz), 6.93 (t, 1H, J = 7.3 Hz), 6.72 (s, 1H), 2.92- 2.95 (m, 4H), 1.07-1.17 (m, 6H)

HPLC (reversed): Rt. (Min) = 3.19

MS (APCI, m / z): 466 (M + l) +. Example 547

Tri (4-pyridinyl) -1-ethanone N- (2_ (2-fluoro-3-chlorochlorolinylino) -1 6— {2— [tri (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

2- (Fluoro-3-chlorophenylamino) -4,6-dihydrazinopyrimidine derivative (0.1 mmol) was dissolved in ethanol (1 ml), and 4-acetylpyridine (0.66 ml, 0.1 tmol) was added. After the addition, the mixture was stirred for 18 hours. After removing the solvent under reduced pressure, the remaining An ethyl acetate-jetil ether solution was added to the residue and suspended. The precipitated solid was crushed and collected by filtration to obtain the desired product (31 mg, 63%).

 MS (APCI, m / z): 490 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.31. Example 548

 1- (4-pyridinyl) -1 -ethanone N- (2-methylthio-6- {2- [tri (4-pyridinyl) ethylidene] hydrazino} -4- 4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 547, followed by purification to obtain the desired product (195 mg, 83%).

 MS (APCI, m / z): 393 (M + l) +

 HPLC (reversed): Rt. (Min) = 2.74. Example 549

1- (4_pyridinyl) -1-ethanone N- (2-phenyl-6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (25 mg, 60 mg). MS (APCI, ra / z): 423 (M + l) +

HPLC (reversed): Rt. (Min) = 3.24. Example 550

 1_ (4-pyridinyl) _1-ethanone N- (2- (pyridine-3-yl) -6- {2- [tri (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (36 mg, 86 mg). ¾-NMR spectrum (270 MHz, DMSO-d ₆ ) <5 ppm: 10.56 (brs, 2H), 9.54 (brs, 1 H), 8.72-8.63 (m, 6H), 7.81 (d, 4H, J = 6.2 Hz) ), 7.57 (dd, 1H, J = 4.6,

(7.8 Hz), 7.17 (s, 1H), 2.40 (s, 6H)

MS (APCI, m / z): 424 (M + l) +

HPLC (reversed): Rt. (Min) = 2.62. Example 551

 1- (4-pyridinyl) -triethanone N- (2- (4-tolyl) -methyl) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (34 mg, 76 mg). MS (APCI, m / z): 451 (M + D +

HPLC (reversed): Rt. (Min) = 3.16. Example 552

1- (4-pyridinyl) -1 -ethanone N- (2- (2-naphthylenyl) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (21 mg, 45%). MS (APCI, m / z): 473 (M + l) +

HPLC (reversed): Rt. (Min) = 3.79. Example 553

 1- (4-pyridinyl)-1-ethanone N- (2- (4-isopropylanilino) -6- {2- [tri (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (495 mg, 60%).

 MS (APCI, m / z): 480 (M + D +

 HPLC (reversed): Rt. (Min) = 3.36. Example 554

 1- (4-Pyridinyl) -1-ethanone N- (2_ (4-methoxyanilino) -6- {2- [2- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 547 and purification was performed to obtain the desired product (146 mg, 79%).

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) <5 ppm: 9.90 (s, 2H), 8.64 (dd, 4H, J TJP03 / 05216

199

= 1.6 Hz, 4.6 Hz), 8.57 (s, 1H), 7.84 (d, 2H, J = 9.2 Hz), 7.78 (dd, 4 H, J = 1.6 Hz, 4.6 Hz), 6.86 (d, 2H, J = 9.2 Hz), 6.67 (s, 1H), 3.74 (s,

3H), 2.34 (s, 6H)

MS (APCI, m / z): 468 (M + D +

HPLC (reversed): Rt. (Min) = 2.79. Example 555

Tri (4-pyridinyl) -1 -ethanone N_ (2- (4-trifluoromethoxyanilino) -6_ {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 547, followed by purification to obtain the desired product (301 mg, 32 mg). MS (APCI, m / z): 522 (M + D +

HPLC (reversed): Rt. (Min) = 3.42. Example 556

1- (4-pyridinyl)-1-ethanone N- (2- (4-methylthioanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (709 mg, 77%).

 MS (APCI, m / z): 484 (M + l) +

HPLC (reversed): Rt. (Min) = 3.08 _o Example 557

 1- (4-pyridinyl) + ethanone N- (2- (4-dimethylaminoazirino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Example 5 Reaction was carried out in the same manner as in '47, followed by purification to obtain the desired product (340 mg, 78%). MS (APCI, m / z): 481 (M + l) +

HPLC (reversed): Rt. (Min) = 2.42. Example 558 Tri- (4-pyridinyl) -triethanone N- (2- (2-fluoroalanilino) -5-methyl-6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (98 mg, 72%). Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) <5 ppm: 9.11 (s, 2H), 8.81 (t, 1H, J = 8.1 Hz), 8.63 (dd, 4H, J = 1.6 Hz, 4.6 Hz), 7.96 (s, 1H), 7.80 (dd, 4H, J = 1.6 Hz, 4.6 Hz), 7.26-7.15 (m, 2H), 7.06-6.99 (m, 1H), 2.36 (s, 6H), 2.30 ( s, 3H)

MS (APCI, m / z): 470 (M + D +

HPLC (reversed): Rt. (Min) = 2.69. Example 559

Tri (4-pyridinyl) -triethanone N- (2- (3-bromoanilino) -6- {2- [tri (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were conducted in the same manner as in Example 547, to obtain the desired product (44 mg, 92%). I - picture R spectrum _{(270 MHz, DMS0-d 6} ) δρριη: 10.03 (brs, 2H), 9.01 (s, 1H), 8.65 (d, 4H, J = 5.9 Hz), 8.14 (d, 1H, J = 8.1 Hz), 8.08 (s, 1H), 7.80 (d, 4H, J = 5.9 Hz), 7.23 (t, 1H, J = 8.1 Hz), 7.08 (d, 1H, J = 8.1 Hz), 6.72 ( s, 1H), 2.36 (s, 6H)

 MS (APCI, m / z): 516 '(M + l) +

 HPLC (reversed): Rt. (Min) = 3.31. Example 560

 1- (4-pyridinyl) -1 -ethanone N- (2- (4-promoanilino) -6- {2_ [1- (4-pyridinyl) ethylidene] hydrazino} -4--4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (37 mg, 64%). 'H-NMR spectrum (270 MHz, DMSO-d ₆ ) ^ ppm: 10.01 (brs, 2H), 9.01 (s, 1H), 8.65 (d, 4H, J = 6.2 Hz), 7.97 (d, 2H, J = 8.9 Hz), 7.79 (d, 4H, J = 6.2 Hz), 7.41 (d, 2H, J = 8.9 Hz), 6.72 (s, 1H), 2.36 (s, 6H)

MS (APCI, m / z): 516 (M + D + HPLC (reversed): Rt. (Min) = 3.46. Example 561

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (3-Promo-Nilino) -6- {2- [tri (4-methanesulfonylphenyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

 2- (3-Promophenylamino) 1,4,6-dihydrazinopyrimidine derivative (0.1 mmol) is dissolved in ethanol (1 ml), and 4-methanesulfonylacedophenone (59 mg, 0.3 bandol) is dissolved in ethanol (1 ml). After the addition, the mixture was stirred for 18 hours. The precipitated solid was pulverized and collected by filtration to obtain the desired product (57 mg, 87%).

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) (5 ppm: 9.97 (brs, 2H), 9.01 (s, 1H), 8.18-8.07 (m, 2H), 8.10 (d, 4H, J = 8.4 Hz ), 7.97 (d, 4H, J = 8.4 Hz), 7.23 (t, 1H, J = 7.8 Hz), 7.08 (d, 1H, J = 7.8 Hz), 6.68 (s, 1H), 3.26 (s, 6H ), 2.40 (s, 6H)

 MS (APCI, m / z): 670 (M + D +

 HPLC (reversed): Rt. (Min) = 4.42. Example 562

 ■ tri (4-methanesulfonylphenyl) -triethanone N- (2- (4-promoanilino) -6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (57 rag, 87%). Ή-band R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 9.94 (brs, 2H), 9.01 (s, 1H), 8.09 (d, 4H, J = 8.6 Hz), 7.97 (d, 4H, J = 8.6 Hz), 7.97 (d, 2H, J = 8.6 Hz), 7.41 (d, 2H, J = 8.6 Hz), 6.68 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H) )

 MS (APCI, m / z): 670 (M + l) + '

HPLC (reversed): Rt. (Min) = 4.56. 03 05216

202 Example 563

 1- (4-pyridinyl) -1-ethanone N- (2- (indane-5-yl-amino) -1-6-{2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (24 mg, 50%). MS (APCI, ffl / z): 478 (M + l) +

 HPLC (reversed): Ri. (Min) = 3.26. Example 564

Tri (4-pyridinyl) -triethanone N- (2- (3,4-dihydro-1H- 1,5-benzodioxepin-1 7-amino) -6- {2- [1- (4-pyridinyl) ethylidene ] Hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 547 and purification was performed to obtain the desired product (33 mg, 64%). MS (APCI, m / z): 510 (M + D +

HPLC (reversed): Rt. (Min) = 3.05. Example 565

 1_ (4-pyridinyl) _1-ethanone N- (2- (3,4-dimethylanilino) -6- {2- [2- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 547 and purification was carried out to obtain the desired product (29 mg, 63%). MS (APCI, m / z): 466 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.23. Example 566

Tri (4-pyridinyl) -triethanone N- (2- (3-trifluoromethyl-4-methoxyanilino) -6- {2-[(tri (4-pyridinyl) ethylidene] hydrazinoto 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (11 mg, 20 mg). MS (APCI, m / z): 536 (M + D +

HPLC (reversed): Rt. (Min) = 3.39. Example 567

Tri (4-methanesulfoerphenyl) -triethanone N- (2- (indane-5-yl-amino) -6- {2- [1- (4- (4-methylsulfonylphenyl) ethylidene] hydrazino) } -4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561, to obtain the desired product (28 mg, 45 °). MS (APCI, m / z): 632 (M + D +

HPLC (reversed): Rt. (Min) = 4.31. Example 568

Tri (4-methanesulfonylphenyl) -triethanone N- (2- (3,4-dimethylanilino) -6_ {2- [tri (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561, to obtain the desired product (18 mg, 29%). MS (APCI, m / z): 620 (M + D +

HPLC (reversed): Rt. (Min) = 4.25. Example 569

 1- (4-methanesulfonylphenyl) -triethanone N- (2- (3-trifluoromethyl-4-methoxyanilino) -6- {2- [2- (tri (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (52 rag, 75 °). MS (APCI, m / z): 690 (M + l

HPLC (reversed): Rt. (Min) = 4.37 Example 570

1_ (4-Methanesulfonylphenyl) -triethanone N- (2- (quinoline-6-ylamino) -6--methanesulfonylphenyl) ethylidene] hydrazino}-4-pyrimidino Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (35 mg, 55 °). Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρηι: 10.01 (brs, 2H), 9.25 (s, 1H), 8.84 (brs, 1H), 8.71 (d, 1H, J = 4.2 Hz), 8.22 (d, 1H, J = 8.6 Hz), 8.12 (d, 4H, J = 8.4 Hz), 7.99 (d, 4H, J = 8. Hz), 7.93-7.88 (m, 2H), 7.45 (dd, 1H, J = 4.2, 8.6 Hz), 6.73 (s, 1H), 3.28 (s, 6H), 2.44 (s, 6H) MS (APCI, m / z): 643 (M + l

HP C (reversed): Rt. (In in) = 3.72 Example 571

Tri (4-methanesulfonylphenyl) -1-ethanone (3,4-difluoroanilino) -6- {2- [1- (4-methylsulfonylphenyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (45 mg, 71%). Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) δρριιι: 9.98 (brs, 2H), 9.10 (s, 1H), 8.58-8.42 (m, 1H), 8.10 (d, 4H, J = 8.6 Hz), 7.97 (d, 4H, J = 8.6 Hz), 7.53-7.48 (m, 1H), 7.35-7.24 (m, 1H), 6.66 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H)

 MS (APCI, m / z): 628 (M + D +

HPLC (reversed): Rt. (Min) = 4.59 Example 572

1- (4_pyridinyl)-1-ethanone N- (2- (3-trifluoromethyl- 4-fluoroalilino) -6- {2- [2- [1- (4-pyridinyl) ethylidene] hydrazino} -4- Pyrimidinyl) hine The reaction and purification were conducted in the same manner as in Example 547 to obtain the desired product (21 mg, 41¾). _C MS (APCI, m / z): 524 (M + D +

HPLC (reversed): Rt. (Min) = 3.52. Example 573 l- (4-pyridinyl) -1 -ethanone-(2- (3,5-difluoroalirino) -6- {2- [2- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (19 mg, 40 mg).

Ή-NMR spectrum _{(270 MHz, DMS0 - d 6} ) <5ppm: 10.09 (brs, 2H), 9.29 (s, 1H), 8.64 (d, 4H, 6.2 Hz), 7.84-7.80 (m, 6H), 6.72 (s, 1H), 6.72-6.65 (m, 1

H), 2.36 (s, 6H)

MS (APCI, m / z): 474 (M + D +

 HPLC (reversed): Rt. (Min) = 3.31 Example 574

 1- (4-pyridinyl) -triethanone N- (2- (3-fluoro-4-methylanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4_pyrimigel) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (32 mg, 69%). 'Η-Band R spectrum (270 MHz, DMS0-d ₆ ) δ pp: 10.02 (brs, 2H), 8.94 (s, 1H), 8.64 (d, 4H, J = 6.2 Hz), 8.18-8.06 (m, 1H), 7.81 (d, 4H, J = 6.2 Hz), 7.48 (d, 1H, J = 8.4 Hz), 7.12 (t, 1H, J = 8.4 Hz), 6.69 (s, 1H), 2.35 (s, 6H), 2.19 (s, 3H)

MS (APCI, m / z): 470 (M + l) +

HPLC (reversed): Rt. (Rain) = 3.29 Example 575

 1- (4-Methanesulfonylphenyl) -triethanone N_ (2- (3-Trifluoromethyl-4-1fluoroarilino) -6- {2- [tri (4-methylsulfonylphenyl) ethylidene] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (66 mg, 98%). MS (APCI, m / z): 678 (M + D +

HPLC (reversed): Rt. (Min) = 4.59 Example 576 Tri (4-methanesulfonylphenyl) -1-ethanone N- (2- (3,5-difluoroallylino)-6- {2- [1- (4- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (46 mg, 73%). Awakening: R spectrum le _{(270 MHz, DMS0-d 6} ) <5 pm: 10.03 (brs, 2H), 9.29 (s, 1H), 8.12 (d, 4H, J = 8.6 Hz), 7.96 (d, 4H , J = 8.6 Hz), 7.85 (d, 2H, J = 9.2 Hz), 6.74-6.67 (m, 1H), 6.67 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H) MS. (APCI, ni / z): 628 (M + D +

HPLC (reversed): Rt. (Min) = 4.56 Example 577

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (3-fluoro-4-methylanilino) -6- {2- [2- (tri (4-methanesulfonylphenyl) ethylidene] hydrazinoto 4-pyrimidinyl) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (41 mg, 66 mg). -NMR spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 9.95 (brs, 2H), 8.93 (s, 1H), 8.20-8.10 (m, 1H), 8.11 (d, 4H, J = 8.6 Hz), 7.97 (d, 4H, J = 8.6 Hz), 7.46 (d, 1H, J = 8.9 Hz), 7.12 (t, 1H, J-8.9 Hz), 6.64 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H), 2.19 (s, 3H)

MS (APCI, ni / z): 624 (M + l) +

 HPLC (reversed): Rt. (Min)-4.31. Example 578

Tri (4-pyridinyl)-1-ethanone N- (2- (quinoline-6-yl-1-amino)-6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (33 rag, 67 °). - NMR spectrum _{(270 MHz, DMS0 - d 6} ) δ ρω: 10.08 (brs, 2H), 9.26 (s, 1H), 8.85-8.80 (m, 1H), 8.72-8.67 (m, 1H), 8.64 (d , 4H, J = 5.9 Hz), 8.20-8.27 (m, 1H), 7.93-7.88 (m, 2H), 7.82 (d, 4H, J = 5.9 Hz), 7.47 (dd, 1H, J = 4.3, 8.1 Hz),, 6.79 (s, 1H), 2.40 (s, 6H)

MS (APCI, m / z): 489 (M + l) +

HPLC (reversed): Rt. (Rain) = 2.58 Example 579

Tri (4-pyridinyl) -1-ethanone N- (2- (4-phenoxyanilino) -6- {2- [tri (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was conducted in the same manner as in Example 547, and purification was performed to obtain the desired product (60 mg, 36%). MS (APCI, m / z): 530 (M + D +

HPLC (reversed): Rt. (Min) = 3.43 Example 580

1- (4-Pyridinyl) -1-i-ethanone _N- (2-anilinol 5-methyl-6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (441 mg, 86%).

Ή- Hokusatsu R spectrum _{(270 MHz, DMS0 - d 6} ) <5 pm: 9.00 (s, 2H), 8.97 (s, 1H), 8. 64 (dd, 4H, J = 1.6 Hz, 4.6 Hz), 8.14 (d, 2H, J = 7.6 Hz), 7.84 (dd, 4H, J = 1.6 Hz, 4.6 Hz), 7.26 (t, 2H, J = 7.6 Hz), 6.91 (t, 1H, J = 7.6 Hz) , 2.37 (s, 6H), 2.28 (s, 3H)

MS (APCI, m / z): 452 (M + l) +

HPLC (reversed): Rt. (Min) = 2.61 Example 581

Tri (4-pyridinyl) -triethanone N- (2_ (3,4-dichloroanilino) _6-{2- [tri (4-pyridinyl) ethylidene] hydrazino}-4-pyrimidinyl) hydrazone

Reaction and purification were conducted in the same manner as in Example 547, to obtain the desired product (36 mg, 71%). -NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 10.06 (brs, 2H), 9.19 (s, 1Η), 8.65 (d, 4H, J = 6.2 Hz), 8.32 (brs, 1H), 8.00 ( d, 1H, J = 8.9 Hz), 7. 80 (d, 4H, J = 6.2 Hz), 7.47 (d, 1H, J = 8.9 Hz), 6.74 (s, 1H), 2.36 (s, 6H)

 MS (APCI, m / z): 506 (M + D +

HPLC (reversed): Rt. (Inin) = 3.40 Example 582,

1- (4-Pyridinyl) -triethanone-(2- (3- (4-pyridinyl) ethylidene] hydrazino} Ripourinylanilino) -6- {2- [4- (Pyridinyl) ethylidene] hydrazino} -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (57 mg, 95%). MS (APCI, m / z): 599 (M + l) +

HPLC (reversed): Rt. (Min) = 2.47. Example 583

1- (4-pyridinyl) -1 -ethanone N- (2- (pifenyl-3-ylamino) -6- {2- [di (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (38 mg, 75%). MS (APCI, m / z): 514 (M + l) +

HPLC (reversed): Rt. (Min) = 3.45 Example 584

l- (4-pyridinyl) -triethanone N- (2- (3-chloroanilino) -6_ {2- [tri-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (32 mg, 68%). R spectrum (270 MHz, DMSO- d ₆ ) δ ριιι: 10.04 (brs, 2H), 9.04 (s, 1H), 8.65 (d, 4H, J = 6.5 Hz), 8.08 (brs, 1H), 8.00 ( d, 1H, J = 8.1 Hz), 7.81 (d, 4H, J = 6.5 Hz), 7.29 (t, 1H, J = 8.1 Hz), 6.95 (d, 1H, J = 8.1 Hz), 6.72 ( s, 1H), 2.36 (s, 6H)

MS (APCI, 'm / z): 472 (M + l HPLC (reversed): Rt. (Min) = 3.12 Example 585

 1- (4-Pyridinyl) -1-ethanone N- (2- (3-Methylanilino) -6- {2- [2- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimigel) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (27 mg, 60 mg). Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) δ ριη: 9.97 (brs, 2H), 8.67 (s, 1Η), 8.65 (d, 4H, J = 6.2 Hz), 7.91 (d, 1H, J = 7.8 Hz), 7.79 (d, 4H, J = 6.

2 Hz), 7.61 (s, 1H), 7.16 (t, 1H, J = 7.8 Hz), 6.74 (d, 1H, J =, 7.8 Hz), 6.70 (s, 1H), 2.35 (s, 6H), 2.31 (s, 3H)

 MS (APCI, m / z): 452 (MH) +

 HPLC (reversed): Rt. (Min) = 2.98. Example 586

卜 (4-pyridinyl) -1-ethanone N- (2- (3-methoxyanilino) -6- {2- [卜 (4-pyridinyl) ethylidene] hydrazino} -4--pyrimidinyl) hydrazone

The reaction was carried out in the same manner as in Example 547, followed by purification to obtain the desired product (46 mg, 99%). ^! H-picture R spectrum (270 MHz, DMSO-d ₆ ) δ ριιι: 9.96 (brs, 2H), 8.82-8.75 (m, 1Η), 8.64 (dd, 4H, J = 1.6, 4.6 Hz), 7.79 ( dd, 4H, J = 1.6, 4.6 Hz), 7.61-7.58 (m, 2H), 7.17 (t, 1H, J = 7.8 Hz), 6.69 (s, 1H), 6.52-6.48 (m, 1H) , 3.76 (s, 3H), 2.35 (s, 6H)

MS (APCI, m / z): 468 (M + D +

HPLC (reversed): Rt. (Min) = 2..86. Example 587

1- ₍₄ -pyridinyl) -triethanone N- (2- (3-trifluoromethylanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547, and the desired product was obtained quantitatively. '' MS (APCI, m / z): 506 (M + l) + HPLC (reversed): Ri. (Min) = 3.35. Example 588

 1- (4-pyridinyl) -triethanone N- (2- (3-tert-butylanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 547, followed by purification to obtain the desired product (35 mg, 71%). MS (APCI, m / z): 494 (M + l) +

HPLC (reversed): Rt. (Min) = 3.47 Example 589

 1- (4-Pyridinyl) -1-ethanone N- (2- (3-trifluoromethoxyanilino) _6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (29 mg, 58%). MS (APCI, m / z): 522 (M + l) +

HPLC (reversed): Rt. (Min) = 3.40 Example 590

 1- (4-pyridinyl)-1-ethanone N- (2-phenylthiomethyl-6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (42 mg, 89%). MS (APCI, m / z): 469 (M + D +

HPLC (reversed): Rt. (Min) = 3.04 Example 591

Tri (4-pyridinyl) -triethanone N_ (2-phenoxymethyl-6- {2- [1_ (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (37 mg, 82%). MS (APCI, m / z): 453 (M + D +

HPLC (reversed): Rt. (Min) = 2.90 Example 592: 1- (4-pyridinyl) -1-ethanone N- (2- (2-methylthioanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone The reaction and purification were conducted in the same manner as in Example 509 to obtain the desired product.

Ή-NMR spectrum (270 MHz, CD30D, TMS) d 8.74 (d, 4H, J = 6.5 Hz), 8.22

(d, 4H, J = 6.5 Hz), 7.95-7.85 (m, 1H), 7.51-7.45 (m, 1H), 7.35-7.29 (m, 2H), 6.84 (s, 1H), 2.47 (s, 3H ), 2.34 (s, 6H)

HPLC (reversed): Rt. (Min) = 3.06

MS (APCI, m / z): 484 (M + l) +. Example 593

 1- (4-Pyridinyl) 1ethanone N- (2- (3-Diitroarilino) — 6— {2— [1- (4-Pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

'IHiMR spectrum _{(270 MHz, DMSO- d 6)} δρρηι: 10.06 (s, 2H), 9.39 (s, 1H), 8.82-8.73 (m, 1H), 8.64 (dd, 4H, J = 1.6, 4.6 Hz) , 8.57-8.55 (m, 1H), 7.82-7.73 (m, 5H), 7.56 (t, 1H, J = 8.1 Hz), 6.75 (s, 1H), 2.36 (s, 6H) MS (APCI, m / z): 483 (M + l) +

HPLC (reversed): Rt. (Min) = 3.02 Example 594

 1- (4-pyridinyl)-1-ethanone N- (2- (3-phenoxyanilino) -6- {2- [2- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 'to give the desired product (16 mg, 30 mg). MS (APCI, m / z): 530 (MH) +

HPLC (reversed): Rt. (Min) = 3.55 Example 595

Tri (4-pyridinyl)-1-ethanone N- (2- (3-methylthioanilino) -6- {2- [1- (4-pi Lysinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (19 mg, 40 mg). '11 - 11 scan Bae spectrum _{(270 ¾1, DMS0 - d 6} ) <5 pm: 9.99 (brs, 2H), 8.83 (s, 1H), 8.65 (d, 4H, J = 6.2 Hz), 7.95 (d, 1H, J = 8.1 Hz), 7.82 (d, 4H, J = 6.2 Hz), 7.71 (s, 1H), 7.22 (t, 1H, J = 8.1 Hz), 6.81 (d, 1H, J = 8.1 Hz), 6.71 (s, 1H), 2.48 (s, 3H), 2.35 (s, 6H)

MS (APCI, m / z): 484 (M + l) +

HPLC (reversed): Rt. (Min) = 3.08 Example 596

 1- (4-pyridinyl) -triethanone N- (2- (3-trifluoromethylthioanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone The reaction was carried out in the same manner as in Example 547, followed by purification to obtain the desired product (49 mg, 91%). MS (APCI, m / z): 538 (M + D +

HPLC (reversed): Rt. (Min) = 3.55 Example 597

Tri (4-methanesulfonylphenyl) -1-ethanone N- (2- (3,4-dichloroanilino) -6- {2- [1- (4-methylsulfonylphenyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z) 660 (M + l) +

HPLC (reversed): Rt. (Min) = 4.81. Example 598

l- (4-methanesulfonylphenyl) -triethanone N- (2- (3-methoxycarbonylanilino) -6- {2- [tri (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pi Limidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product. MS (APCI, ra / z): 650 (M + D +

HPLC (reversed): Rt. (Rain) = 3.35 Example 599

卜 (4-Methanesulfonylphenyl)-thoethanone N- (2- (biphenyl-2-ylamino)-6- {2- [2- [1- (4- methanesulfonylphenyl) ethylidene] hydrazino 4_ Pirimi Ginirile) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 668 (M + D +

HPLC (reversed): Rt. (Min) = 4.51 Example 600

Tri (4-methylsulfonylphenyl) -triethanone N- (2- (3-chloroanilino) -6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

E - negation R spectrum _{(270 MHz, DMSO- d 6)} <5ppm: 9.96 (s, 2H), 9.02 (s, 1H), 8. 82-8.73 (m, 1H), 8.12-8.09 (m, 5H) , 7.98-7.95 (m, 5H), 7.28 (t, 1H, J = 8.1 Hz), 6.93 (dd, 1H, J = 1.4, 8.9 Hz), 6.67 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H)

 MS (APCI, ra / z): 626 (M + l

 HPLC (reversed): Rt. (Min) = 4.34 Example 601

G- (4-methylsulfonylphenyl) -1-ethanone N- (2- (3-methylalanilino) -6- {2- [tri (4-methylsulfonylphenyl) ethylidene] hydrazino}- 4-Pyrimidinyl) The reaction was conducted in the same manner as in Example 561, and the product was purified to obtain the desired product.

lH - NMR spectrum _{(270 MHz, DMSO- d 6)} ά ρπι: 9.91 (brs, 2H), 8.66 (s, 1H), 8.10 (d, 4H, J = 8.6 Hz), 7.97 (d, 4H, J = 8.6 Hz), 7.93 (d, 1H, J = 8.1 Hz), 7.60 (s, 1H), 7.17 (t, 1H , J = 8.1 Hz), 6.74 (d, 1H, J = 8.1 Hz),

6.65 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H), 2.30 (s, 3H)

MS (APCI, m / z): 606 (M + l) +

HPLC (reversed): Rt. (Min) = 4.06 Example 602

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (3-Methoxyanilino) -6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino 4-pyrimidini Example 561 The reaction was carried out in the same manner as described above, followed by purification to obtain the desired product.

MS (APCI, m / z): 622 则 +

HPLC (reversed): Rt. (Min) = 4.00. Example 603

 1- (4-Methanesulfonylphenyl)-1-ethanone N- (2- (3-trifluoromethyladilino) -6- {2- [1- (4-methylsulfonylphenyl) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 660 (M + D +

HPLC (reversed): Rt. (Min) = 4.55 Example 604

 1- (4-methanesulfonylphenyl) -triethanone N- (2- (3-tert-butylanilino) -6- {2- [1- [4- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidi Nil) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 648 (M + D +

HPLC (reversed): Rt. (Min) = 4.47 Example 605

Tri (4-methanesulfoylphenyl) -1-ethanone N- (2- (3, -trifluoromethoxyanilino) -6- {2- [2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino 4_ Pyrimidinirile) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 676 (M + l) +

HPLC (reversed): Rt. (Min) = 4.60 Example 606

 1- (4-Mesulfonylphenyl) -1 -ethanone N- (2-phenylthiomethyl-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazon

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 623 (M + D +

HPLC (reversed): Rt. (Min) = 4.54 Example 607

 1- (4-Mesulfonylphenyl) -triethanone N- (2-phenoxymethyl-6- {2- [1- [4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 607 (M + l) +

HPLC (reversed):. Rt ( min) = 4. 45 0 Example 608

1- (4-Methanesulfonylphenyl)-1-ethanone N- (2- (3-ditroarilino) -6- {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή-NMR spectrum (270 MHz, DMSO- d ₆ ) δ pm: 10.02 (brs, 2H), 9.40 (s, 1H), 8.75 (d, 1H, J = 8.4 Hz), 8.58 (s, 1H), 8.10 (d, 4H, J = 8.6 Hz), 7.97 (d, 4H, J = 8.6 Hz), 7.76 (d, 1H, J = 8.4 Hz), 7.57 (t, 1H, J = 8. Hz) , 6.71 (s, 1H), 3.27 (s, 6H), 2.41 (s, 6H)

MS (APCI, m / z): 637 (M + D +

HPLC (reversed): Rt. (Min) = 4.37 Example 609

1- (4-Methanesulfonylphenyl) -1 -ethanone N- (2- (3-phenoxyanilino) -6- {2- [1- (4-methylsulfonylphenyl) ethylidene] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 684 (M + D +

HPLC (reversed): Rt. (Min) = 4.57 Example 610

 1- (4-Methanesulfonylphenyl) -1-ethanone N- (2- (3-Methylthioanilino) -6- {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino.}-4 _Pyrimidine) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 638 (Mll) l

HPLC (reversed): Rt. (Min) = 4.18 Example 611

 1- (4-Methanesulfonylphenyl) -1 -ethanone N- (2- (3-trifluoromethylthioanilino) -6- {2- [1- (4-methylsulfonylphenyl) ethylidene ] Hydrazino}-4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product. MS (APCI, m / z): 692 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.77 Example 612

 1- (4-pyridinyl) -triethanone N- (2- (4-n-propylanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (68 mg, 24%). MS (APCI, m / z): 480 (M + l) +

HPLC (reversed): Rt. (Min) = 3.44 Example 613

 1- (4-pyridinyl) -triethanone N- (2- (4-n-octylanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (116 mg, 43 mg).

 MS (APCI, m / z): 550 (M + l) +

HPLC (reversed): Rt. (Min) = 4.36 Example 614

l- (4-pyridinyl)-1-ethanone N-(2- (4- sec-butylanilino)-6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 547 and purification was performed to obtain the desired product (94 mg, 45%). MS (APCI, m / z): 494 (M + 1) +

HPLC (reversed): Rt. (Min) = 3.56 Example 615

 1- (4-Pyridinyl) _1-ethanone N- (2_ (4-ethoxyanilino) -6- {2_ [2- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

The reaction was carried out in the same manner as in Example 547, followed by purification to obtain the desired product (83 mg, 49%). MS (APCI, m / z): 482 (M + D +

HPLC (reversed): Rt. (Min) = 3.06 Example 616

1- (4-Pyridinyl) -1-ethanone N- (2- (4-chloroazirino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 547, followed by purification to obtain the desired product (125 mg, 87.8%). '

Ή-丽 R spectrum (270 MHz, D S0-d ₆ ) δ ρπι: 9.98 (s, 2H), 8.98 (s, 1H), 8.65 (dd, 4H, J = 1.6 Hz, 4.6 Hz), 8.02 (d, 2H, J-8.9 Hz), 7.79 (dd, 4H, J = 1.6 Hz, 4.6 Hz), 7.28 (d, 2H, J = 8.9 Hz), 6.72 (s, 1H), 2.36 (s, 6H )

 MS (APCI, m / z): 472 (M + l) +

HPLC (reversed): Rt. (Min) = 3.27 Example 617

l- (4-pyridinyl)-1-ethanone N- (2- (4_n-hexyloxyanilino) -6- {2- [1_ (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 547 and purification was performed to obtain the desired product (107 mg, 64%).

 MS (APCI, m / z): 538 (M + D +

HPLC (reversed): Rt. (Min) = 3.80. Example 618

1- (4-Methanesulfonylphenyl) -triethanone N- (2- (4-n-propylanilino) -6- {2- [1- (4-Mesulfonylphenyl) ethylidene] hydrazino} -4 -Pirimi Gini Re) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (133 mg, 88 mg). MS (APCI, m / z): 634 (M + D +

HPLC (reversed): Rt. (Min) = 4.39 Example 619

1- (4-Methanesulfoerphenyl) -1-ethanone N- (2- (4-n-octylanilino)-6- {2-[((4-methanesulfonylphenyl) ethylidene] hydrazinoto 4-pyrimidinyl) ) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (46 mg, 44 °). MS (APCI, m / z): 704 (M + l) +

HPLC (reversed): Rt. (Min) = 5.35 Example 620

U- (4-methylsulfonylphenyl)-1-ethanone N- (2- (4-sec-butylanilino) -6- {2- [1- (4- (4-methanesulfoerphenyl) ethylidene] hydrazino} -4 -Pirimidi Nirile) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (101 mg, 64%).

 MS (APCI, m / z): 648 (M + D +

HPLC (reversed): Rt. (Min) = 4.55 Example 621

 1- (4-Methanesulfonylphenyl) -toluenone N- (2- (4-Chloroanilino) -6- {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (57 mg, 49%). Ή- 丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.92 (s, 2H), 8.98 (s, 1H), 8.09 (d, 4H, J = 8.6 Hz), 8.02 (d, 2H) , J = 8.9 Hz), 7.97 (d, 4H, J = 8.6 Hz), 7.29 (d, 2H, J = 8.6 Hz), 6.67 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H ) MS (APCI, m / z): 626 (M + D + 6

220

HPLC (reversed): Rt. (Min) = 4.34 Example 622

 1- (4-Methanesulfonylphenyl) _1_ethanone N- (2- (4-Benzylanilino) -6-{2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino 4-pyrimidini) V ) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (39 nig, 36 °). MS (APCI, m / z): 682 (M + D +

HPLC (reversed): Rt. (Min) = 4.62. Example 623

G (4-pyridinyl) -1ethanone N- (2- (3,5-ditert-butylanilino) -6- {2- [1- (4- (pyridinylyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 550 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.09 Example 624

 1- (4-pyridinyl) -toethanone N- (2- (3-methyl-4-isopropylanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 494 (M + l) +

HPLC (reversed): Rt. (Min) = 3.55 Example 625

 1- (4-pyridinyl) -triethanone N- (2- (4-cyclohexylalanilino) -6- {2-[(4- (pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 520 (Mil) + HPLC (reversed): Rt. (Min) = 3.73 Example 626

 1- (4-Pyridinyl) -1-ethanone- (2- (3,5-dimethylanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 466 (M + l '

HPLC (reversed): Rt. (Min) = 3.25 Example 627

1- ₍₄ - pyridinyl) - Bok ethanone _N - ₍₂ - (fluoren-2-Iruamino) - ₆ - - (4 - pyridinyl) Echiriden] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 526 (M + 1) +

HPLC (reversed): Rt. (Min) = 3.58. Example 628

 1- (4-Pyridinyl) -1 -ethanone N-(2- (3-Chloro-4-trimethyl thioanilino) _6 {2- [Tri (4-pyridinyl) ethylidene] hydrazino} hydrimidino

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 572 (M + D +

HPLC (reversed): Rt. (Min) = 3.92 Example 629

 1- (4-Methanesulfonylphenyl)-1-ethanone N- (2- (4-cyclohexylanilino)-6- {2- [2- (4- (4-methanesulfoylphenyl) ethylidene] hydrazino-4- Pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product. MS (APCI, m / z): 674 (M + l) +

HPLC (reversed): Rt. (Min) = 4.76 Example 630,

1- (4-Methanesulfonylphenyl) -1-ethanone N_ (2- (3,5-dimethylanilino) -6- {2- [1- (4- (methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidini J)) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 620 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.21 Example 631

 1- (4-pyridinyl) -triethanone N- (2- (4-isopropoxyililino) -6- {2-[(4- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 496 (M + D +

HPLC (reversed): Rt. (Min) = 3.15 Example 632

 1- (4-Pyridinyl) -1-ethanone N- (2- (4--2-troarilino) -6- {2-[[(4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (13 mg, 68%). MS (APCI, m / z).: 483 (M + l) l

HPLC (reversed): Rt. (Min) = 3.25. Example 633

 Tri (4-pyridinyl) -1-ethanone N- (2- (4-benzilanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (55 mg, 36 mg). MS (APCI, m / z): 528 (M + D +

 HPLC (reversed): Rt. (Rain) = 3.53 Example 634

 1- (4-Methanesulfonylphenyl)-1-ethanone N- (2- (4-Ethoxyanilino) -6- {2_ [1- (4-methanesulfoerphenyl) ethylidene] hydrazino} -4-Pyrimidini Reaction and purification were carried out in the same manner as in 56 1 to obtain the desired product (34 rag, 29¾): MS (APCI, m / z): 636 (M + l) +

HPLC (reversed): Rt. (Min) = 4.12 Example 635

l- (4-Methanesulfonylphenyl) -triethanone N- (2- (4-n-hexyloxyanilino) -6- {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazinoto 4-pyrimitone Jinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (53 mg, 44%). MS (APCI, m / z): 692 (M + l) +

HPLC (reversed): Rt. (Min) = 2.81 Example 636

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (3,5-di-tert-butylanilino) -6- {2- [1- (4-methylsulfonylphenyl) Ethylidene] hydrazino} -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 704 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.91 Example 637

1- (4-Mesulfonylphenyl) _1-ethanone N- (2- (3-Methyl-4-isopro Pyruanilino) -6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 648 (M + l) +

HPLC (reversed): Rt. (Min) = 4.46. Example 638

 1- (4-pyridyl) -1-ethanone Ν- (2τ (4- {2- [1- (4-pyridyl) ethylidene] hydrazino} -anilino) -6- {2- [1-(4-pyridyl) ) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 599 (M + l

HPLC (reversed): Rt. (Min) = 2.49 Example 639

 1- (4-pyridyl) -triethanone N- (2- (3-chloro-4-trifluoromethoxyanilino) -6- {2- [tri (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydra Reacted and purified in the same manner as in Example 474 to obtain the desired product.

MS (APCI, m / z): 556 (M + l) +

HPLC (reversed): Rt. (Min) = 3.86 Example 640

Tri (4-methanesulfonylphenyl) -triethanone N- (2- (3-chloro-1--4-methoxymethoxyanilino) -6- {2- [tri (4-methanesulfonylphenyl) ethylidene ] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 710 (M + l) +

HPLC (reversed): Rt. (Min) = 5.28 Example 641

Tri (4-pyridyl)-1-ethanone N- (2- (3-fluoro-4-methoxyanilino) -6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 486 (M + D +

HPLC (reversed): Ri. (Min) = 3.0391 Example 642

1- (4-Methanesulfonylphenyl)-1-ethanone N_ (2- (3-fluoro-4-methoxymethoxylinilino)-6- {2_ [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4 -Pirimigel) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 640 (M + l

HPLC (reversed): Rt. (Min) = 4.22. Example 643

 1- (4-methanesulfonylphenyl) -triethanone N- (2_ (2-methoxyanilino) -5-methyl-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ppm: 9.18 (brs, 2H), 9.13 (d, 1H, J = 8.1 Hz), 8.14 (d, 4H, J = 8.6 Hz), 7.99 (d , 4H, J = 8.6 Hz), 7.41

(s, 1H), 7.06-6.92 (m, 3H), 3.91 (s, 3H), 3.27 (s, 6H), 2.41 (s, 6H), 2.32 (s, 3H)

 MS (APCI, m / z): 636 (M + D +

HPLC (reversed): Rt. (Min) = 3.78 Example 644 Tri (4-methanesulfoylphenyl) -triethanone N- (2- (2-methoxyanilino) -5-n-propyl-1-6-[2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) (5 ppm: 9.15-9.10 (m, 1H), 9.11 (brs, 2H), 8.13 (d, 4H, J = 8.6 Hz), 8.00 (d, 4H , J = 8.6 Hz), 7.42 (brs, 1 H), 7.10-6.90 (m, 3H), 3.91 (s, 3H), 3.28 (s, 6H), 2.98-2.88 (m, 2H), 2.66 (s, 6H), 2.41 (s, 3H), 1.68-1.55 (m, 2H), 0.99 (t, 3H, J = 7.3 Hz) MS (APCI, m / z): 664 (M + l) +

HPLC (reversed): Rt. (Min) = 4.04 Example 645

l- (4-Methanesulfonylphenyl) -triethanone N- (2- (2-methoxy-5-methylanilino) -1-6- [2_ [1- (4-methanesulfonylphenyl) ethylidene] hydrazino}-4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 636 (M + l) +

HPLC (reversed): Rt. (Min) = 4.07 Example 646

 1- (4-Methanesulfonylphenyl) -toluenenon-N- (2- (2-methoxy-5-phenylanilino) -1-6- {2- [toluene (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 698 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.47 Example 647.

1- (4-Mesulfurphenyl)-1-ethanone N- (2- (2-methoxy-5-tert 6- {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino}-4-pyrimigyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 678 (M + D +

HPLC (reversed): Rt. (Min) = 4.47. Example 648

Tri (4-methanesulfonylphenyl) -triethanone N- (2_ (2-methoxy-5-trifluoromethylarino)) 6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino}- 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 678 (M + D +

HPLC (reversed): Rt. (Min) = 4.72 Example 649

Tri (4-methanesulfoerphenyl) -triethanone N- (2- (2-fluoro-4- (1-methylanilino))-6_ {2- [1- (4-methanesulfoerphenyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

'Η- 丽 R spectrum (270 MHz, DMSO-d ₆ ) δρρπι: 9.99 (s, 2H), 8.20-8.16 (m, 4H), 8.13-8.06 (m, 4H), 7.98-7.95 (m, 2H ), 7.72 (s, 1H), 7.08-6.98 (m, 1H), 6.67 (s, 1H), 3.26 (s, 6H), 2.37 (s, 6H), 2.31 (s, 3H)

MS (APCI, m / z): 624 (M + D +

HPLC (reversed): Rt. (Min) = 4.11 Example 650

l- (4-Methanesulfonylphenyl) -toluenenon- (2- (2,6-difluoroallylino) -1 6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino 4-Pyrimidinyl) hydrazone PT / JP03 / 05216

The reaction and purification were conducted in the same manner as in Example 561 to obtain the desired product.

MS (APCI, / z): 628 (M + D +

HPLC (reversed): Rt. Din) = 3.94 Example 651

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (2,3,4-trifluoraline) -1 6- {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (25 mg, 39%). Ή-NMR spectrum (270 z, DMS0-d ₆ ) δ ριιι: 9.99 (s, 2H), 8.28 (s, 1H), 8.06 (d, 4H, J = 8.6 Hz), 7.96 (d, 4H) , J = 8.6 Hz), 7.90-7.88 (m, 1H), 7.29-7.25 (m, 1H), 6.69 (s, 1H), 3.26 (s, 6H), 2.37 (s, 6H)

MS (APCI, m / z): 646 (M + D +

HPLC (reversed): Rt. (Min) = 4.36 Example 652

 1- (4-Methanesulfoerpheel) -toethanone N- (2- (2-Methoxyanilino) -1 5 1-benzyl-6 {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino}-4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 712 (M + D +

HPLC (reversed): Rt. (Min) = 4.23. Example 653

Tri (4-methanesulfonylphenyl) -triethanone N- (2- (4-methylanilino) -6_ {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριη: 9.89 (brs, 2H), 8.66 (s, 1H), 0305216

229

8.09 (d, 4H, J = 8.6 Hz), 7.97 (d, 4H, J = 8.6 Hz)> 7.84 (d, 2H, J = 8.4 Hz), 7.08 (d, 2H, J = 8.4 Hz), 6.64 (s, 1H), 3.27 (s, 6H), 2.36 (s, 6H), 2.27 (s, 3H)

MS (APCI, ra / z): 606 (M + l

HPLC (reversed): Rt. (Min) = 4.01 Example 654,

Tri (4-methanesulfoelfenyl) -1-ethanone N- (2- (2-fluoro-5-methylanilino) -1-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino}- 4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 624 (M + D + '

HPLC (reversed): Rt. (Min) = 4.16 Example 655

l- (4-Methanesulfonylphenyl) -1-ethanone N- (2- (2-fluoro-4-chloroanilino) -1-6- (2- [1- (4-methansulfonylphenyl) ethylidene) ] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

〖H-丽 R spectrum (270 MHz, DMS0-d ₆ ) <5ppm: 10.05 (brs, 2H), 8.38 (t, 1H, J = 8.6 Hz), 8.18 (d, 1H, J = 8.6 Hz), 8.07 (d, 4H, J = 8.6 Hz), 7.97 (d, 4H, J = 8.6 Hz), 7.46 (d, 1H, J = 10.8 Hz), 7.24 (d, 1H, J = 8.6 Hz), 6.70 ( s, 1H), 3.26 (s, 6H), 2.38 (s, 6H)

MS (APCI, m / z): 644 (M + lH ',

HPLC (reversed): Rt. (Min) = 4.45 Example 656

Tri (4-methanesulfonylphenyl) -triethanone N- (2- (2,3-difluoroallylino) -1- 6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4 -Pili Mind lily) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 628 (M + D +

HPLC (reversed): Rt. (Min) = 4.38 Example 657

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (2-phenylethylamino) -1-6- (2- [1- [4- (4-methanesulfonylphenyl) ethylidene] hydrazino) 4-pyrimidinizore) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 620 (M + D +

HPLC (reversed): Rt. (Min) = 3.99. Example 658

l- (4-Methanesulfonylphenyl) -triethanone N- (2- (hexylhexylamino) -1- 6- {2- [1_ (4_methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinifure) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 598 (M + l) +

HPLC (reversed): Rt. (Min) = 4.03 Example 659

Tri (4-methanesulfonylphenyl) -1-ethanone N- (2-piberidyl-6- {2-[{(4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 584 (M + l) +

HPLC (reversed): Rt. (Min) = 3.91 Example 660

 1- (4-Methanesulfonylphenyl) -triethanone N- (2-pyrrolidyl-1-6- {2- [1- (4-methylsulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 570 (M + D +

HPLC (reversed): Rt. (Min) = 3.59 Example 661

Tri (4-methanesulfonylphenyl) -triethanone N- (2- (2-fluoro-3-chloroanilino) -1-6- (2- [1-(4-methanesulfophenyl)) ethylidene] hydrazino 4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 644 (M + D +

HPLC (reversed): Rt. (Min) = 4.45 Example 662

 1- (4-Methanesulfonylphenyl) -toluenenon-N- (2-methylthio-1-6-(2- [1- (4-methansulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazo N

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 547 (M + D +

HPLC (reversed): Rt. (Min) = 4.46. Example 663

1- (4-Methanesulfonylphenyl) -triethanone N- (2-phenyl 6- {2_ [1- (4-methansulfonylphenyl) ethylidene] hydrazino-4-pyrimidinyl) hydrazone Example 5 61 The reaction was carried out in the same manner as in 1, followed by purification to obtain the desired product. MS (APCI, m / z): 577 (M + l) + HPLC (reversed): Rt. (Min) = 4.88 Example 664

Tri (4-methanesulfoylphenyl) -triethanone N- (2- (pyridine-1-yl) -1-6-[2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazinoto 4-pyrimidinyl) Hydrazone.

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

'H-NMR spectrum (270 MHz, DMSO-d ₆ ) δ ρπι: 10.50 (brs, 2H), 9.55 (brs, 1

H>, 8.75-8.60 (m, 2H), 8.18 (d, 4H, J = 8.6 Hz), 7.99 (d, 4H, J = 8.6 Hz), 7.60-7.50 (m, 1H), 7.12 (s, 1H), 3.26 (s, 6H), 2.44 (s, 6H)

 MS (APCI, ra / z): 578 (M + 1) +

 HPLC (reversed): Rt. (Min) = 3.78 Example 665

ί- (4-Methanesulfonylphenyl) -triethanone Ν_ (2_ (4-tolylmethyl) -1-6- {2-[(4- (methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 605 (M + D +

HPLC (reversed): Rt. (Min) = 4.17 Example 666

 1- (4-Methanesulfonylphenyl) -triethanone N-C2- (Naphthyl-1-yl) -6- {2- [1- (4-Methanesulfonylphenyl) edylidene] hydrazino} -4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 627 (M + D +

HPLC (reversed): Rt. (Min) = 5.62 Example 667

 1- (4-Methanesulfonylphenyl)-1-ethanone N- (2- (2-ethoxylanilino) -1 6- {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino 4-pyrimidinyl ) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (27 mg, 42%). Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριη: 10.22 (s, 2H), 8.95-8.88 (m, 1H), 8.09 (d, 4H, J = 8.6 Hz), 7.97 (d , 4H, J = 8.6 Hz), 7.43 (s, 1H), 7.04-6.90 (m, 3H), 6.69 (s, 1H), 4.14 (q, 2H, J = 6.8 Hz), 3.26 (s, 6H) , 2.40 (s, 6H), 1.42 (t, 3H, J = 6.8 Hz)

MS (APCI, m / z): 636 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.10. Example 668

 1- (4-Pyridyl) -triethanone N- (2- (2-Methyl-1-41-fluoroalirino) -1-6- {2- [1- (4-Pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

'Η- 丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.96 (brs, 2H), 8.64 (d, 4H, J = 5.9 Hz), 7.79 (s, 1H), 7.75 (d, 4H, J = 5.9 Hz), 7.75-7.68 (m, 1H), 7.11-6.95 (m, 2H), 6.68 (s, 1H), 2.31 (s, 6H, 2.26 (s, 3H)

MS (APCI, m / z): 470 (M + D +

 HPLC (reversed): Rt. (Min) = 2.90 Example 669

 1- (4-Methanesulfonylphenyl)-1-ethanone N- (2_ (2-methyl-4_fluoroanilino) -1- 6- {2- [1- (4-Mesulfonylphenyl) ethylidene] hydrazino } -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) δ ρπι: 9.90 (brs, 2H), 8.06 (d, 4H, J = 8.4 Hz), 7.95 (d, 4H, J = 8.4 Hz), 7.77 (s , 1H), 7.77-7.71 (m, 1H), 7.11-6.98 (m, 2H), 6.64 (s, 1H), 3.25 (s, 6H), 2.35 (s, 6H), 2.27 (s, 3H)

 MS (APCI, m / z): 624 (M + l) l

 HPLC (reversed): Rt. (Min) = 4.06'Example 670

 1- (4-pyridyl) -triethanone N- (2- (4-carboxymethylanilino) -1- 6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (13 mg, 61%). MS (APCI, m / z): 496 (M + l) +

 HPLC (reversed): Rt. (Min) = 2.59 Example 671

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (2,4-difluoroanilino) -1- 6- {2-[(4- (4-methanesulfoelfenylyl) ethylidene] hydrazino) 4-Pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 561, followed by purification to obtain the desired product (34 mg, 61%).

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δριη: 9.96 (s, 2H), 8.24-8.15 (m, 1

H), 8.06 (d, 4H, J = 8.6 Hz), 7.95 (d, 4H, J = 8.6 Hz), 7.32-7.23 (m, 1H), 7.09-7.02 (m, 1H), 6.67 (s, 1H), 3.24 (s, 6H), 2.35 (s, 6H)

 MS (APCI, m / z): 628 (M + D +

 HPLC (reversed): Rt. (Min) = 4.31'Example 672

l- (4-methanesulfonylphenyl) -1-ethanone N- (2- (3-fluorosulfonylphenyl) -1-6-{2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4 -Pyrimidini lire) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (40 mg, 81%). Ή - NMR spectrum _{(270 MHz, DMS0 - d 6} ) δ ριη: 9.97 (s, 2H), 9.06 (s, 1H), 8. 30-8.20 (m, 1H), 8.12 (d, 4H, J = 8.6 Hz), 7.97 (d, 4H, J = 8.6 Hz), 7.60-7.55 (m, 1H), 7.32-7.23 (m, 1H), 6.75-6.68 (m, 1H), 6.66 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H)

MS (APCI, m / z): 610 (M + l) +

HPLC (reversed): Rt. (Min) = 4.37. Example 673

U- (4-methylsulfonylphenyl)-1-ethanone N- (2- (4-fluoroanilino) -1 6- {2- [1_ (4-methanesulfonylphenyl) ethylidene] hydrazino}-4- Pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (22 mg, 48 mg). Image R spectrum _{(270 MHz, DMS0 - d 6} ) δρριη: 9.90 (s, 2H), 8.84 (s, 1H), 8.

09 (d, 4H, J = 8.8 Hz), 8.01-7.95 (m, 6H), 7.13-7.06 (m, 2H), 6.66 (s,

1H), 3.26 (s, 6H), 2.39 (s, 6H)

 MS (APCI, m / z): 610 (M + D +

 HPLC (reversed): Rt. (Min) = 4.22 Santan Example 674, 'Tri (4-methanesulfonylphenyl) -triethanone N- (2- (2,4,5-trifluoroalinylino) -1- {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino} -4-Pirimigel) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (35 mg, 71%). 'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 10.10 (s, 2H), 8.75 (brs, 1Η), 8.08 (d, 4H, J = 8.7 Hz), 8.03-7.93 (m, 5H) '7.62-7.52 (m, 1H), 6.68 (s, -1H), 3.24 (s, 6H), 2.37 (s, 6H)

MS (APCI, m / z): 646 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.65 Example 675 PT / JP03 / 05216

236 tri (4-methanesulfonylphenyl) -triethanone N- (2- (2-fluoro-5-chloroanilino) -1- 6- {2- [1- (4-methylsulfonylphenyl) ethylidene] hydrazino } -4-Pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (31 mg, 87%). 'H-NMR spectrum _{(270 MHz, DMS0-d 6} ) (5 pm: 10.10 (s, 2H), 8.57 (brs, 1H), 8.09 (d, 4H, J = 8.7 Hz), 8.00-7.92 (m, 5H), 7.31-7.23 (m, 1H), 7.08-7. 03 On, 1H), 6.69 (s, 1H), 3.24 (s, 6H), 2.37 (s, 6H)

MS (APCI, m / z): 644 (M + D +

HPLC (reversed): Rt. (Min) = 4.66 Example 676

Tri (4-methanesulfonylphenyl) -triethanone N- (2- (4-phenoxyanilino) -1-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino 4_pyrimidi Nil) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (1 mg, 11%). MS (APCI, m / z): 684 (M + D +

HPLC (reversed): Rt. (Min) = 4.68 Example 677

1- (4-Methanesulfonylphenyl) -triethanone N- (2- (4-Trifluoromethoxyanilino) -1-6- (2- [tri (4-methanesulfoylphenyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (2 mg, 21%). MS (APCI, m / z): 676 (M + l

HPLC (reversed): Rt. (Min) = 4.69. Example 678

1- (4-Methanesulfonylphenyl) -1 -ethanone N- (2- (4-Methylthioanilino) -1-6- {2- [2- (4- (4-methylsulfonylphenyl) ethylidene] hydrazino}- 4-pyrimidi 0305216

237 Nil) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (17 rag, 71 °). MS (APCI, m / z) 638 (M + D +

 HPLC (reversed): Rt. (Min) = 4.29 Example 679

 1- (4-Methanesulfoelpheel) -triethanone N- (2- (2-fluoroanilino) -1-5-methyl-6- {2- [2- (1- (4-methylsulfonylphenyl) ethylidene] hydrazino}- 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

 MS (APCI, m / z): 624 (M + D +

 HPLC (reversed): Rt. (Min) = 3.98

'' Example 680

 Tri (4-methanesulfonylphenyl) -1-ethanone N- (2-anilino-5-methyl-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 The reaction was carried out in the same manner as in Example 56 1, and purification was performed to obtain the desired product (4 mg, 12%). MS (APCI, m / z): 606 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.87 Example 681

 4- (2-methanesulfonylphenyl) -1-ethanonone N- (2- (2-fluoroarilino) -1 6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561, to obtain the desired product (40 mg, 89%). 'H-NMR spectrum _{(270 MHz, DMS0-d 6} ) δ ριη: 10.03 (s, 2H), 8.49-8.43 (m, 1H), 8.07 (d, 4H, J = 8.8 Hz), 7.96 (d, 4H , J = 8.8 Hz), 7.82 (d, 1H, J = 2.1 Hz), 7.26-7.16 (m, 1H), 7.08-7.00 (m, 1H), 6.68 (s, 1H), 3.24 (s, 6H), 2.37 (s, 6H)

MS (APCI, m / z): 610 (M + l) +

HPLC (reversed): Rt. (Min) = 4.13 Example 682

Tri (4-sulfamoylofenyl) -Triethanonone N- (2-anilino-1- 6- {2-[(4-Sulfamoylofenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone Examples 561 and The reaction was carried out in the same manner and purified to obtain the desired product (38 mg, 64%). iH-NMR spectrum (270 MHz, DMS0_d ₆ ) δρρι: 9.78 (s, 2H), 8.79 (s, 1H), 8.05-8.00 (m, 6H), 8.07 (d, 4H, J = 8,9 Hz) ), 7.40 (s, 4H), 7.27 (t, 2H, J = 8.4 Hz), 6.92 (t, 1H, J = 7.0 Hz), 6.57 (s, 1H), 2.38 (s, 6H)

MS (APCI, m / z): 594 (M + D +

HPLC (reversed): Rt. (Min) = 3.59. Example 683

l- (4-Sulfamoyl-phenyl) -triethanone N- (2- (3,5-difluoroallino) -1-6- {2- [1- (4-Sulfamoylofenyl) ethylidene] hydrazino}- 4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (19 mg, 30 mg). Ή-Awake R spectrum (270 MHz, DMS0-d ₆ ) δρρηι: 9.91 (s, 2H), 9.30 (s, 1H), 8.05 (d, 4H, J = 8.6 Hz), 7.87-7.84 (m, 6H), 7.41 (s, 4H), 6.72-6.65 (m, 1H), 6.59 (s, 1H), 2.39 (s, 6H)

MS (APCI, m / z): 630 (M + D +

HPLC (reversed): Rt. (Min)-4.12 Example 684

 1- (4-pyridyl) -triethanone N- (2- (2-fluoro-4-methoxyanilino) -1-6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (36 mg, 70%). ^l H - NMR spectrum _{(270 MHz, DMS0-d 6} ) δ ριη: 9.96 (s, 2H), 8.62 (dd, 4H, J = 1.3 Hz, 4.6 Hz), 7.91-7.78 (m, 1H), 7.75 ( dd, 4H, J = 1.3 Hz, 4.6 Hz, 6.88 (dd, 1H, J = 2.8 Hz, 12.5 Hz), 6.80-6.70 (m, 1H), 6.68 (s, 1H), 3.76 (s, 3H ), 2.30 (s, 6H)

MS (APCI, m / z): 486 (M + l) +

 HPLC (reversed): Rt. (Min) = 2.96 Example 685

 1- (4-pyridyl) -triethanone N- (2- (4-ethylpyranilino) -1- 6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4- 4-pyrimidyl) hydrazone,

 Reaction and purification were conducted in the same manner as in Example 547, to obtain the desired product (22 mg, 41%). MS (APCI, m / z): 466 (M + l) +

HPLC (reversed): Rt. (Min) = 3.26 Example 686

Tri (4-pyridyl) -1_ethanone N- (2- (4-trifluoromethylanilino) -1- 6_ {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (40 mg, 79%). MS (APCI, m / z): 506 (M + D +

HPLC (reversed): Rt. (Min) = 3.53 Example 687

 1- (4-pyridyl)-1-ethanone N- (2- (4-n-butoxyanilino) -1- 6_ {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (26 mg, 31%). MS (APCI, m / z): 510 (M + D +

HPLC (reversed): Rt. (Min) = 3.43. Example 688 （(4_pyridyl) -1 -ethanone N-(2- (4-n-pentyloxyanilino) -1 6_ {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, i / z): 524 (M + D +

HPLC (reversed): Rt. (Min) = 3.66 Example 689

 1- (4-pyridyl)-1-ethanone N- (2- (4-n-butylanilino) -1- 6- {2- [2- (4-pyridyl) ethylidene] hydrazino} -4--4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 494 (M + l

HPLC (reversed): Rt. (Min) = 3.65 Example 690

 1- (4-Methanesulfonylphenyl) -triethanone N- (2_ (2-fluoro-4-methoxianilino) -1- 6_ {2- [1- [4- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (43 mg, 66%). Awake R spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 9.91 (s, 2H), 8.06 (d, 4H, J = 8.4 Hz), 7.96 (d, 4H, J = 8.4 Hz), 7.90-7.85 (m , 1H), 7.76 (s, 1H), 6.89 (dd, 1H, J = 2.6 Hz, 9.9 Hz), 6.76 (d, 1H, J = 9.1 Hz), 6.65 (s, 1H),

3.78 (s, 6H), 3.57 (s, 3H), 2.36 (s, 6H)

MS (APCI, m / z): 640 (M + l) +

HPLC (reversed): Rt. (Min) = 3.97 Example 691

Tri (4-methanesulfonylphenyl) -triethanone N- (2- (4_ethylfuranylino) -1- 6_ {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (33 mg, 45 °). Ή-NMR spectrum _{(270 MHz, DMSO- d 6)} 5 pm:

MS (APCI, m / z): 620 (M + l) +

HPLC (reversed): Rt. (Min) = 4.28 Example 692

 1- (4-Methanesulfonylphenyl) -toluenenon N_ (2- (4-Trifluoromethylanilino) -1-6- (2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazinoto 4_ Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561, to obtain the desired product (49 mg, 74%). MS (APCI, m / z): 660 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.68. Example 693

1- (4-Methanesulfonylphenyl)-1-ethanone N- (2- (4-n-pentyloxyanilino) -1- 6- {2- [1- (4-Methanesulfonylphenyl) ethylidene ] Hydrazino}-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561, to obtain the desired product (38 mg, 60 mg). MS (APCI, m / z): 678 (M + D +

HPLC (reversed): Rt. (Min) = 4.68 Example 694

 1- (4-methanesulfonylphenyl) -triethanone N- (2- (4-n-butylanilino) -1-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidi Two Lille) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561, to obtain the desired product (27 mg, 59%). Ή- 丽 R spectrum (270 MHz, DMSO-d _s ) δ ρριιι: 9.87 (s, 2H), 8.65 (s, 1H), 8.10 (d, 4H, J = 8.6 Hz) , 7.97 (d, 4H, J = 8.6 Hz), 7.83 (d, 2H, J = 8.6 Hz), 7.09 (d, 2H, J = 8.6 Hz), 6 64 (s, 1H), 3.20 (s, 6H), 2.57-2.50 (m, 2H), 2.39 (s, 6H), 1.61-1.50 (m, 2H), 1.39-1.25 (m, 2H), 0.91 (t, 3H, J = 7.3 Hz)

 MS (APCI, m / z): 648 (M + D +

HPLC (reversed): Rt. (Min) = 4.69 Example 695

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (4-Methoxyanilino) -1-6-{2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino}-4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (11 mg, 45 °). MS (APCI, m / z): 622 (M + D +

HPLC (reversed): Rt. (Min) = 3.88 Example 696

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (2-Methoxyanilino) -1-6- [2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone

The reaction was carried out in the same manner as in Example 561, followed by purification to obtain the desired product (6 mg, 19 mg). ¾- Keio R spectrum _{(270 MHz, DMS0-d 6} ) 5ppm: 10.19 (s, 2H), 8.85 (d, 1H, J = 5.9 Hz), 8.09 (d, 4H, J = 8.4 Hz), 7.97 (d , 4H, J = 8.4 Hz), 7.42 (s, 1H), 7.05-6.92 (m, 3H), 6.68 (s, 1H), 3.91 (s, 3H), 3.27 (s, 3H), 2.40 (s, 6H)

 MS (APCI, m / z): 622 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.06. Example 697

1- (4-Metersulfamoylofenyl) -triethanone N- (2-anilino_6-{2- [1- (4-Methylsulfamoyl-phenyl) ethylidene] hydrazino} _4-pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (44 mg, 71%). -NMR spectrum (270 MHz, DMSO- d ₆ ) άρρπι: 9.82 (s, 2H), 8.76 (s, 1H), 8.07-8.00 (m, 6H), 7.81 (d, 4H, J = 8.6 Hz) , 7.45 (q, 2H, J = 4.9 Hz), 7.27 (t, 2H, J = 7.6 Hz), 6.90 (t, 1H, J = 7.3 Hz), 6.61 (s, 1H), 2.45 (d, 6H, J = 4.9 Hz), 2.39 (s, 6H)

MS (APCI, m / z): 622 (M + l) +

HPLC (reversed): Rt. Din) = 4.00. Example 698

Tri (4-dimethylsulfamoylophenyl)-1-ethanone N- (2-anilino-6- {2- [tri (4-dimethylsulfamoyl-phenyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (50 mg, 77 mg). 'Η-wake R spectrum (270 MHz, DMSO- d ₆ ) δ ριη: 9.91 (s, 2H), 8.75 (s, 1H), 8.10 (d, 4H, J = 8.6 Hz), 7.96 (d, 2H, J = 8.6 Hz), 7.77 (d, 4H, J = 8.6 Hz), 7.27 (t, 2H, J = 8.6 Hz), 6.92 (t, 1H, J = 8.6 Hz), 6.70 (s, 1H) ,. 2.65 (s, 12H), 2.40 (s, 6H)

MS (APCI, m / z): 650 (M + l

HPLC (reversed): Rt. (Min) = 4.46. Example 699

 1- (4-methanesulfonylphenyl) -triethanone N- (2- (4-n-butoxyanilino) —6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino 4-pyrimidinyl ) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (26 mg, 20%). MS (APCI, m / z): 664 (M + D +

HPLC (reversed): Rt. (Min) = 4.76 Example 700 Tri (4-pyridyl) -triethanone N- (2- (3,5-dichloroanilino)-6- {2- [tri (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

¾-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 10.09 (brs, 2H), 9.24 (s, 1H), 8.64 (d, 4H, J = 5.9 Hz), 8.09 (brs, 2H), 7.81 (d, 4H, J = 5.9 Hz), 7.06 (brs, 1H), 6.73 (s, 1H), 2.36 (s, 6H)

MS (APCI, m / z): 506 (M + l) +

HPLC (reversed): Rt. (Min) = 3.67 Example 701

 1- (4-Pyridyl) -triethanone N- (2- (3-chloro-1-4-fluoroanilino) -1-6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

Ή- Hokusatsu R spectrum _{(270 MHz, DMSO- d 6)} <5 pm: 10.03 (brs, 2H), 9.04 (s, 1H), 8.65 (d, 4H, J = 6.2 Hz), 8.27-8.20 (m, 1H), 7.97-7.89 (m, 1H), 7.80 (d, 4H, J = 6.2 Hz), 7.29 (t, 1H, 9.2 Hz), 6.72 (s, 1H), 2.36 (s, 6H) MS (APCI , m / z): 490 (MH) +

HPLC (reversed): Rt. (Min) = 3.33 Example 702

Tri (4-pyridyl)-1-ethanone N- (2- (2,3-dihydro-benzo [1,4] dioxin-6-yl-amino)-6- {2- [tri (4-pyridyl) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

Ή- 丽 R spectrum (270 MHz, DMS0-d ₆ ) δριη: 10.01 (brs, 2H), 8.64 (d, 4H, J = 6.2 Hz), 7.82 (d, 4H, J = 6.2 Hz), 7.69 ( brs, 1H), 7.27 (d, 1H, 'J = 8.6 Hz), 6.75 (d, 1H, J = 8.6 Hz), 6.64 (s, 1H), 4.27-4.20 (m, 4H), 2.35 ( s, 6H)

MS (APCI, m / z): 495 (M + D + ' HPLC (reversed): Rt. (Min) = 2.82. Example 703 ^J

Tri (4-methanesulfonylphenyl) -1-ethanone N- (2- (2-methoxy-3_fluoroanilino) -1-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή- 丽 R spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 10.22 (brs, 2H), 8.69 (d, 1H,

J = 8.1 Hz), 8.09 (d, 4H, J = 8.6 Hz), 7.98 (d, 4H, J-8.6 Hz), 7.51 (s, 1H), 7.15-7.07 (m, 1H), 6.91-6.83 ( m, 1H), 6.71 (s, 1H), 3.94 (s, 3H), 3.26 (s, 6H), 2.40 (s, 6H)

MS (APCI, m / z): 640 (M + l) +

HPLC (reversed): Rt. (Min) = 4.33 Example 704

 1- (4-Methanesulfonylphenyl) -1 -ethanone N- (2- (3,5-dichloroanilino) -6- {2- [tri (4-methylsulfonylphenyl) ethylidene] hydrazino } -4-Pyrimidi The reaction and purification were conducted in the same manner as in Example 561 to obtain the desired product.

R spectrum (270 MHz, DMS0-d ₆ ) δ ριιι: 10.03 (brs, 2H), 9.24 (s, 1H), 8.11 (d, 4H, J = 8.4 Hz), 8.10 (brs, 2H), 7.96 (d, 4H, J = 8.4 Hz), 7.06 (brs, 1H), 6.69 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H).

MS (APCI, m / z): 660 (M + 1) +

HPLC (reversed): Rt. (Min) = 5.32 Example 705

l- (4-methanesulfonylphenyl) -triethanone N- (2- (3-chloro-4-1-fluoroanilino) -1-6-{2-[(4-methanesulfonylphenyl) ethylidene] hydrazino} _4-pyrimigel ) Hydrazone Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (48 mg, 75%). ¾-NMR spectrum (270 MHz, DMSO-d ₆ ) άριη: 9.97 (brs, 2H), 9.04 (s, 1H), 8.24-8.18 (m, 1H), 8.10 (d, 4H, J = 8.4 Hz) , 7.98-7.90 (m, 5H), 7.33-7.26 (m, 1H), 6.67 (s, 1H), 3,26 (s, 6H), 2.40 (s, 6H)

MS (APCI, m / z): 644 (M + D +

HPLC (reversed): Rt. (Mill) = 4.60 Example 706

 1- (4-methanesulfonylphenyl) -thuetanone N- (2- (2,3-dihydro-benzo [1,4] dioxin-6-yl-l-amino) — 6- {2_ [1- (4 -Methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

-NMR spectrum (270 MHz, DMSO- d ₆ ) δ ριη: 9.88 (brs, 2H), 8.58 (s, 1H), 8.10 (d, 4H, J = 8.6 Hz), 7.96 (d, 4H, J = 8.6) Hz), 7.70 (brs, 1H), 7.30 (d, 1H, J = 8.9 Hz), 6.74 (d, 1H, J = 8.9 Hz), 6.60 (s, 1H), 4.28-4.

15 (m, 4H), 3.26 (s, 6H), 2.38 (s, 6H)

 MS (APCI, m / z): 650 (M + l

 HPLC (reversed): Rt. (Min) = 4.05. Example 7Q7

 1- (4-pyridyl)-1-ethanone N- (2- (benzo [1,3] dioxo-l-5-yl-amino) '-1- (2- [1- [4- (4-pyridyl) ethylidene) ] Hydrazino} -4-pyrimidinyl) hydrazone The reaction and purification were conducted in the same manner as in Example 547 to obtain the desired product.

Ή-circle R spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.96 (brs, 2H), 8.70 (s, 1H), 8.64 (d, 4H, J = 6.5 Hz), 7.99 (brs, 1H), 7.79 (d, 4H, J = 6.5 Hz), 7.17 (d, 1H, J = 8.6 Hz), 6.81 (d, 1H, J = 8.6 Hz), 6.65 (s, 1H), 5.99 (s, 2H ), 2.34 (s, 6H)

 MS (APCI, m / z): 482 (M + 1) +

HPLC (reversed): Rt. (Min) = 2.91. Example 708

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (Benzo [1,3] dioxol-5-ylamino) _ 6- {2_ Phenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (11 mg, 17%). 'H-NMR spectrum _{(270 MHz, DMS0-d 6} ) ά ριη: 9.90 (brs, 2H), 8.69 (s, 1H), 8.09 (d, 4H, J = 8.6 Hz), 7.96 (d, 4H, J -8.6 Hz), 7.91 (brs, 1H), 7.22 (d, 1H, J = 8.4 Hz), 6.81 (d, 1H, J = 8.4 Hz), 6.62 (s, 1H), 5.98 (s, 2H) ), 3.26 (s, 6H), 2.39 (s, 6H)

MS (APCI, m / z): 636 则 +

HPLC (reversed): Rt. (Min) = 4.15. Example 709

1- (4_Phenylsulfonylphenyl) -triethanone N- (2-anilino-6- {2_ [tri (4-phenylsulfophenyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 716 (M + D +

HPLC (reversed): Rt. (Min) = 4.89. Example 710

 1_ (4-Ethylsulfonylphenyl)-1-ethanone N- (2-anilino-1-6- [2- [1- (4-ethylsulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as for 561 to give the desired product.

'H-NMR spectrum _{(270 MHz, DMS0-d 6} ) <5ppm: 9.93 (s, 2H), .8.77 (s,' 1H), 8. 11 (d, 4H, J = 8.4 Hz), 8.00-7.91 (m, 6H), 7.28 (t, 2H, J = 7.8 Hz), 6.94-6.90 (m, 1H), 6.66 (s, 1H), 3.38-3.30 (m, 4H), 2.40 (s, 6H ), 1.14 (t, 6H, J = 7.3 Hz) MS (APCI, m / z): 620 (M + l

 HPLC (reversed): Rt. (Min) = 4.35. Example 711

 3-U, 6-bis- [N'-a-pyridine-4-yl-ethylidene) -hydrazino] -pyrimidine-2-ylamino} -N-hexyl-N-methyl-benzamide

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 579 (M + l) +

HPLC (reversed): Rt. (Min) = 3.58. Example 712

 1- (4-pyridyl) -triethanone N- (2- (3- (1,1,1,2,2-tetrafluoroethoxy) anilino) -1-6- (2- [1- (4-pyridyl) ) Ethylidene] hydrazino} -4-pyrimidinyl) hydra The reaction and purification were conducted in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 554 (M + D +

HPLC (reversed): Rt. (Min) = 3.52. Example 713

 4- {4,6-bis- [Ν '-(1- (4-methanesulfoerphenyl) -ethylidene) -hydrazino] -pyrimidine-2-ylamino} _Ν-phenyl-Ν-methyl-benzamide

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 725 (M + l) +

HPLC (reversed): Rt. (Min) = 4.28 Example 714 '

4-{4,6-bis- [Ν '-(1- (4-methanesulfonylphenyl) -ethylidene) -hydrazino] -pyrimidine-2-ylamino} -Ν-hexyl_ -methyl-benzamide

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product. 5216

249

MS (APCI, m / z): 733 (M + D +

HPLC (reversed): Rt. (Min) = 4.61 Example 715

1- (4-methanesulfonylphenyl) -triethanone N- (2- (3- (1,1,2,2-tetrafluoromouth ethoxy) anilino) -1-6- (2- [1_ (4-methanesulfonylphenyl) Enil) ethylidene] hi. Drazino}-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product. '' MS (APCI, m / z): 708 (M + l

HPLC (reversed): Rt. (Min) = 4.69 Example 716

 1- (4-methansulfonylphenyl)-1-ethanone N- (2- (1H-indazo-1-yl 6-yl) amino)-6- {2- [1- Sulfonylphenyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 632 (M + 1) +

HPLC (reversed): Rt. (Min) = 3.67 Example 717

 3_ {4, 6-bis- [Ν '-(1-pyridine-4-yl-ethylidene) -hydrazino] -pyrimidine-2-ylamino} -Ν, Ν-dimethyl-benzamide

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 509 (M + l) +

HPLC (reversed): Rt. (Min) = 2.73. Example 718

1- (4-pyridyl) -triethanone N- (2- (1H-indazo-1-yl-6-yl) amino) -1- 6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 478 (M + l

HPLC (reversed): Rt. (Min) = 3.78 Example 719

 1- (4-pyridyl) -1-ethanone N- (2- (1-methanesulfonyl 2,3-dihydro-1H-indole-6-yl) -amino) -1-6- (2- [1- ( 4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 557 (M + lH

 HPLC (reversed): Rt. (Min) = 2.93 Example 720

Tri (4-methanesulfonylphenyl) -triethanone Ν- (2-α-methanesulfonyl 2,3-dihydro-1H-indole-6-yl) -amino) -1- 6- {2- [1- (4-- Methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 711 (M + D +

HPLC (reversed): Rt. (Min) = 4.07 Example 721

Tri (4-methanesulfonylphenyl) -triethanone N- (2- (1H-indazol-5-yl) amino) -1-6- (2- [tri (4-methylsulfonylphenyl)) Ethylidene] hydrazino} -4-Pyrimidinylyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 632 (M + D +

HPLC (reversed): Rt. (Min) = 3.67 Example 722 4-{4,6-bis- [Ν '-(1- (4-pyridyl) -ethylidene) -hydrazino] -pyrimidine-2-ylamino} -Ν-phenyl-Ν-methyl-benzamide

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 571 (M + D +

HPLC (reversed): Rt. (Min) = 3.16. Example 723

 4- {4,6-bis- [Ν '-(1- (4-pyridyl) -ethylidene) -hydrazino] -pyrimidine-2-ylamino} -Ν-hexyl-Ν-methyl-benzamide

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 579 (M + l) +

HPLC (reversed): Rt. (Min) = 3.52, Example 724.

3- {4,6-bis- [Ν'-a-pyridine-4-yl-ethylidene) -hydrazino] -pyrimidine-2-ylamino N, N-dimethyl-benzenesulfonamide

 The reaction was carried out in the same manner as in Example 547, followed by purification to obtain the desired product.

MS (APCI, m / z): 545 (M + l) +

HPLC (reversed): Rt. (Min) = 3.07 Example 725

 3- {4,6-bis- [Ν '-(1- (4-Methanesulfonylphenyl) -ethylidene) -hydrazino] -pyrimidine-2-ylamino} -N-hexyl-N-methyl-benzamide

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 733 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.70 Example 726

3-{4,6-bis- [Ν'- (4- (4-methanesulfoerphenyl) -ethylidene) -hydrazide [No] -Pyrimidine-2-ylaminobutane, N, N-dimethyl-benzenesulfonamide, reacted in the same manner as in Example 561, and purified to obtain the desired product.

MS (APCI, m / z): 699 (M + l) l

HPLC (reversed): Rt. (Min) = 4.28 Example m

 1- (4-Methanesulfonylphenyl)-1-ethanone N- (2- (3,4,5-trifluorofluoro-2-lino) -6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino } -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (31 mg, 48 mg).

'H-NMR spectrum _{(270 MHz, DMSO- d 6)} δρριη: 10.04 (brs, 2Η) ·, 9.26 (s, 1H), 8.11 (d, 4H, J = 8.4 Hz), 8.09-7.98 (m, 2H ), 7.96 (d, 4H, J = 8.4 Hz), 6.67 (s, 1H), 3.26 (s, 6H), 2.40 (s, 6H)

MS (APCI, m / z): 646 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.93. Example 728

 1- (4-Pyridyl) -triethanone N- (2- (3,4,5-Trifluoroalirino) -6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

'H-picture R spectrum (270 MHz, DMSO-d ₆ ) δ ριη: 10.10 (brs, 2H), 9.26 (s, 1H), 8.64 (d, 4H, J' = 6.2 Hz), 8.08-7.95 (m , 2H), 7.80 (d, 4H, J = 6.2 Hz), 6.72 (s, 1H), 2.36 (s, 6H) ''

MS (APCI, m / z): 492 (M + D +

 HPLC (reversed): Rt. (Min) = 3.40 Example 729

1- (4-pyrrolidine-1 1-sulfonylphenyl) -ethanone N- (2-anilino-6- {2 -[l- (4-Pyrrolidine-1-1-sulfofenphenino-4-pyrimigel) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product

MS (APCI, m / z): 7024 (Mil) +

HPLC (reversed): Rt. (Min) = 4.90 Example 730

Uru (4-Merino

ドラ ジノ } -4-ピリミジニル）ヒドラゾン —6- {2-

Dorazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Awake R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 9.82 (brs, 2H), 8.78 (s, 1H), 8.05 (d, 4H, J = 8.6 Hz), 8.01 (d, 2H, J = 7.6 Hz) ), 7.84 (d, 4H, J = 8.6 Hz), 7.74 (brs, 2H), 7.27 (t, 2H, J = 7.6 Hz), 6.92 (t, 1H, J = 7.6 Hz), 6.6Ό (s, 1H), 3.38-3.28 (m, 4H), 3.16 (s, 6H), 2.96 (ί, 4H, J = 5.7 Hz), 2.39 (s, 6H)

MS (APCI, m / z): 710 (M + D +

HPLC (reversed): Rt. (Min) = 4.21 Example 731

l- (4-Methoxycarbonylmethylsulfamoylphenyl) -triethanone N- (2-anilino-6- {2- [1- (4-Methoxycarbonylmethylsulfamoylenyl) ethylidene] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 738 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.22 Example 732

1- (4-azetidine-1-sulfonylphenyl)-1-ethanone N- (2-anilino-1 6_ {2 -[U- (4-azetidine-1-1-sulfoerfenino-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, ni / z): 674 (M + D +

HPLC (reversed): Rt. (Min) = 4.63. Example 733

 1- (4-n-propylsulfamoylenyl) -1--1-ethanone N- (2-anilino-6- {2- [1- (4-n-propylsulfamoylenyl) ethylidene] hydrazino } -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

H-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριη: 9.81 (s, 2H), 8.78 (s, 1H), 8.06-7.98 (in, 7H), 7.82 (d, 4H, J = 8.4 Hz), 7.61-7.59 (m, 1H), 7.27 (t, 2H, J = 7.3 Hz), 6.92 (i, 1H, J = 7.3 Hz), 6.59 (s, 1H), 2.75-2.71 (m, 4H), 2.38 (s, 6H), 1.42-1.32 (m, 4H), 0.79 (t, 6H, J = 7.3 Hz)

MS (APCI, m / z): 678 (M + D +

HPLC (reversed): Rt. (Min) = 4.78. Example 734

1- (4-Cyclopropylsulfamoylenyl) -triethanone N- (2-anilino-1

6- {2- [1- (4-Cyclopropylsulfamoyl-phenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (43 mg, 64 mg).

H-NMR spectrum (270 MHz, DMS0-d ₆ ) (5 ppm: 9.83 (s, 2H), 8.80 (s, 1Η), 8.07 (d, 4H, J = 8.4 Hz), 8.02-7.92 (ηι, 4H) , 7.84 (d, 4H, J = 8.4 Hz),

7.7 (t, 2H, J = 7.8 Hz), 6.92 (t, 1H, J = 7.8 Hz), 6.60 (s, 1H), 2.39

(s, 6H), 2.20-2.10 (m, 2H), 0.53-0.44 (m, 4H), 0.40-0.35 (m, 4H)

 MS (APCI, m / z): 674 (M + D +

HPLC (reversed): Rt. (Min) = 4.55. Example 735

 1- (4-methylsulfamoylenyl) -triethanone N- (2- (2,4,5-trifluorofluorolinilino) -6- {2- [1- (4-methylsulfamoylofyl) Nyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (25 mg, 37%). H-NMR spectrum (270 MHz, DMS0-d ₆ ) 5 pm: 10.05 (s, 2H), 8.86-8.82 (m,

1H), 8.05 (d, 4H, J = 8.6 Hz), 7.94 (brs, 2H), 7.80 (d, 4H, J = 8.6 Hz), 7.65-7.46 (m, 2H), 6.65 (s, 1H) , 2.45 (d, 6H, J = 4.6 Hz), 2.38 (s,

6H)

 MS (APCI, m / z): 676 (M + l) +

 HPLC (reversed): Ri. (Min)-4.57. '' Example 736

 1- (4-Methylsulfamoyl-phenyl) -triethanone N- (2- (2-fluoroanilino) -1-6- (2- [tri (4-methylsulfamoyl-phenyl) ethylidene] hydrazino} -4

-Pyrimidinyl) hydrazone

 Reaction and purification were conducted in the same manner as in Example 561, to obtain the desired product (22 mg, 34%).

H-NMR spectrum (270 MHz, DMS0-) άρριη: 9.97 (s, 2H), 8.48 (t, 1H, J = 6.8 Hz), 8.04 (d, 4H, J = 8.6 Hz), 7.83-7.77 (m, 5H), 7.46 (brs, 2H), 7.26-7.16 (m, 2H), 7.08-7.03 (m, 1H), 6.65 (s, 1H), 2.46 (s, 6H), 2.37 (s, 6H)

 MS (APCI, m / z): 640 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.12. Example 737

l- (4-i-Phenyl) -triethanone N- (2- (2-fluoradilino) _6- {2-[(2- (4-mi-phenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (56 mg, 84 mg). H-NMR spectrum (270 MHz, DMSO-d ₆ ) ρριη: 10.05 (s, 2H), 8.45-8.38 (m,

1H), 8.10-8.02 (m, 5H), 7.77 (d, 4H, J = 8.4 Hz), 7.22-7.06 (m, 3H), 6.74 (s, 1H), 2.65 (s, 12H), 2.38 (s, 6H)

MS (APCI, m / z): 668 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.69. Example 738

 1- (4-pyridyl) -triethanone N- (2- (2,4-methoxy-5-chloroanilino)-6- {2- [tri (4-pyridyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 532 (M + D +

HPLC (reversed): Rt. (Min) = 3.14 Example 739

 1- (4_Methanesulfoerphenyl) -triethanone ^ (2- (2,4_methoxy-5-hydroxyanilino) -6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino } -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 686 (M + D +

 HPLC (reversed): Rt. (Min) = 4.23 Example 740

 1- (4-Pyridyl) -toluene non-N- (2- (2,4-dimethylanilino) -1-6- {2- [toluene (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (23 mg, 61%). MS (APCI, m / z): 466 (M + D +

HPLC (reversed): Rt. (Min) = 2.99 05216

257 Example 741

Tri- (4-pyridyl) -triethanone N- (2- (2-methyl-3-fluoroalirino) -1- 6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (1 mg, 10 mg). MS (APCI, m / z): 470 (M + l

 HPLC (reversed): Rt. (Min) -3.02 Example 742

l- (4-pyridyl) -triethanone N- (2- (2-methyl-5-fluoroalirino) -6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (2 mg, 13%). MS (APCI, m / z): 470 (M + lH

HPLC (reversed): Rt. (Min) = 3.08. Example 743

 1- (4-Methanesulfonylphenyl) -1-ethanone N- (2- (2,4-dimethylanilino) — 6- {2- [tri (4-methylsulfonylphenyl) ethylidene] hydrazino } -4-Pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (9 mg, 18%). -丽 R spectrum (270 MHz, DMS0-d ₆ ) δρρηι: 9.87 (s, 2H), 8.05 (d, 4H, J = 8.5 Hz), 7.94 (d, 4H, J = 8.5 Hz), 7.67-7.60 ( m, 2H), 7.01 (s, 1H), 6.97 (s, 1H), 6.62 (s, 1H), 3.24 (s, 6H), 2.33 (s, 6H), 2.26 (s, 3H), 2.2 1 (s, 3H)

 MS (APCI, m / z): 620 (M + l) +

HPLC (reversed): Rt. (Min) = 4.22 Example 744

1- (4-methylsulfonylphenyl)-1-ethanone N- (2- (2-methyl-4-methoxyanilino) -1-6- (2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} _Four 5216

258

-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (7 mg, 21%). MS (APCI, m / z): 636 (M + l) l

HPLC (reversed): Rt. (Min) = 4.00 Example 745

 1- (4-Pyridyl) -toethanone N- (2- (2,3-Dimethylanilino) -1-6- (2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 466 (M + 1) +

 HPLC (reversed): Rt. (Min) = 2.94 Example 746

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (2-methyl-3-fluoroanilino) -1- 6- {2_ [tri (4-methylsulfonylphenyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 624 (M + l) +

HPLC (reversed): Rt. (Min) = 4.05 Example 747

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (2-Methyl-5-fluoroanilino) -1-6- {2_ [Tri (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-Pyrimidinyl ) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to give the desired product (3 mg, 17%). 'Η- 丽 R spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 10.09 (s, 2H), 8.34 (d, 1H, J = 10.5 Hz), 8.10 (d, 4H, J = 8.8 Hz), 7.96 (d, 4H, J = 8.8 Hz), 7.51 (s, 1H), 7.20 (t, m, J = 7.6 Hz), 6.77 (dt, 1H, J = 2.9 Hz, 8.4 Hz), 6.67 ( s, 1H), 3.26 (s, 6H), 2.38 (s, 6H), 2.26 (s, 3H) MS (APCI, m / z): 624 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.10. Example 748

l- (4_methanesulfonylphenyl) -triethanone N- (2- (2-methyl-4-chloroanilino) -1-6- {2- [tri (4-methanesulfonylphenyl) ethylidene] hydrazino}-4- Pyrimidinile) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 640 (M ++

HPLC (reversed): Rt. (Min) = 4.22 Example 749

 1- (4_Methanesulfonylphenyl) -1-ethanone N- (2- (2-methylanilino) -1-6- [2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidini Le) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (6 mg, 44 mg). E - negation R spectrum _{(270 MHz, DMSO- d 6)} δρρηι: 9.94 (s, 2H), 8.07 (d, 4H, J = 8.4 Hz), 8.00-7.90 (m, 5H), 7.65 (s, 1H) , 7.25-7.15 (m, 2H), 7.00 (t, 1H, J = 7.7 Hz), 6.65 (s, 1H), 3.26 (s, 6H), 2.36 (m, 6H), 2.27 (s, 3 H)

 MS (APCI, m / z): 606 (M + D +

HPLC (reversed): Rt. (Min) = 3.74 Example 750

1- (4-Power-rubumoylmethylsulfamoylenyl) -toethanone N- (2-anilino-1-6- (2- (1- (4-power-rubumoylmethylsulfamoylofenyl)) ethylidene ] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 708 (M + l 0305216

260

HPLC (reversed): Rt. (Inin) = 3.43. Example 751

Tri (4-ethylsulfamoylfurenyl) -triethanone N- (2-anilino-6- {2- [tri (4-ethylsulfamoyl-phenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) δ ριη: 9.82 (s, 2H), 8.78 (s, 1H), 8.06-7.98 (m, 6H), 7.83 (d, 4H, J = 8.4) Hz), 7.58 (t, 1H, J = 5.1 Hz), 7.27 (t, 2H, J = 7.6 Hz), 6.94-6.62 (m, 1H), 6.59 (s, 1H), 2.82 (q, 4H , J = 7.0 Hz), 2.38 (s, 6H), 0.98 (t, 6H, J = 7.0 Hz)

MS-(APCI, m / z): 650 (M + D +

HPLC (reversed): Rt. (Min) = 4.28. Example 752

 1- (4-pyridyl) -triethanone N_ (2- (3-fluoro-4-bromoazirino) -1 6_ {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

-NMR spectrum (270 MHz, DMSO-d ₆ ) δ ρπι: 10.07 (brs, 2H), 9.26 (s, 1H), 8.64 (d, 4H, J = 6.2 Hz), 8.50-8.40 (m, 1H), 7.80 (d, 4H, J = 6.2 Hz), 7.53-7.47 (m, 2H), 6.72 (s, 1H), 2.36 (s, 6H)

MS (APCI, m / z): 534 (M + D +

HPLC (reversed): Rt. (Rain) = 3.47. Example 753 '

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (3-fluoro-4-bromoanilino) -1 6- {2- [tri (4-methanesulfonylphenyl) ethylidene] hydrazino}-4- Pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product. ^l H-NMR spectrum (270 MHz, DMSO-d ₆ ) δρριη: 10.01 (brs, 2H), 9.26 (s, 1H), 8.55-8.45 (m, 1H), 8.11 (d, 4H, J = 8.6 Hz) , 7.97 (d, 4H, J = 8.6 Hz), 7.53-7.48 (m, 2H), 3.26 (s, 6H), 2.41 (s, 6H)

 MS (APCI, m / z): 688 (M + l) +

HPLC (reversed): Rt. (Min) = 4.86 Example 754

l- (4-pyridyl)-1-ethanone N- (2-tenilino-5-benzyl-6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

Ή-Band R spectrum (270 MHz, DMSO- d ₆ ) 6ppm: 9.10 (s, 1H), 8.88 (brs, 2H), 8.55 (d, 4H, J = 6.2 Hz), 8.16 (d, 2H, J = 8.1 Hz), 7.66 (d, 4H, J = 6.

2 Hz), 7.35-7.27 (m, 5H), 7.27 (t, 2H, J = 8.1 Hz), 6.92 (t, 1H, J = 8.

1 Hz), 4.36 (brs, 2H), 2.15 (s, 6H)

MS (APCI, m / z): 528 (M + D +

 HPLC (reversed): Rt. (Min) = 3.22 Example 755

Tri (4-methanesulfonylphenyl) -triethanone N- (2-anilino-5-benzyl-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

'H-NMR spectrum (270 MHz, DMSO-d ₆ ) <5 ppm: 9.10 (s, 1H), 8.85 (brs, 2H), 8.16 (d, 2H, J = 8.1 Hz), 7.98 (d, 4H, J = 8.4 Hz), 7.88 (d, 4H, J = 8.4 Hz), 7.45-7.28 (m, 5H), 7.28 (t, 2H, J = 8.1 Hz), 6.94 (t, 1H, J = 8. 1 Hz), 4.36 (brs, 2H), 3.25 (s, 6H), 2.20 (s, 6H)

MS (APCI, m / z): 682 (M + l) +

HPLC (reversed): Rt. (Min) = 4.34 Example 756

Tri- (4-methanesulfophenyl) -triethanone N- (2- (3-fluoro-4-trifluoromethylmethylarino) -1 6- {2- [1- (4-methylsulfoerphenyl) ethylidene ] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, / z): 678 (M + l) +

HPLC (reversed): Rt. (Min) = 5.24 Example 757

U- (4-pyridyl) -1-ethanone N- (2- (3-fluoro-4-1-trifluoromethylanilino) -1 6- {2- [U- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydra Zon

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 524 (M + 1) +

HPLC (reversed): Rt. (Min) = 3.85. Example 758

 1- (4-Trifluoromethylsulfonylphenyl) -1 -ethanone N- (2-anilinol 6- {2- [1- (4-trifluoromethanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 700 (M + D +

HPLC (reversed): Rt. (Min) = 5.94 Example 759

 1- (4-Methylsulfamoylphenyl) -triethanone N- (2- (2-Methyl-15-fluoroanilino) -1-6- (2- [1- (4-Methylsulfamoylphenyl) ethylidene) ] Hydrazino}-4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (41 mg, 83%). MS (APCI, m / z): 654 (M + D +

HPLC (reversed): Rt. (Min) = 4.15 Example 760

l- (4-Ethylsulfamoylphenyl) -triethanone N- (2- (2-methyl-5-fluoroanilino) -1-6- (2- [1- (4-ethylsulfamoylphenyl) ethylidene] Hydrazino} -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (27 mg, 51%). MS (APCI, m / z): 682 (M + D +

HPLC (reversed): Rt. (Min) = 4.45 Example 761

 1- (4-pyridyl) -1-ethanone N- (2-anilino-5_ethoxy-6- {2- [4- (4-pyridyl) ethylidene] hydrazino} -4--4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

醒 -wake R spectrum (270 MHz, DMSO- d ₆ ) δ ριη: 9.18 (brs, 2H), 9.13 (s, 1H), 8.65 (d, 4H, J-6.2 Hz), 8.14 (d, 2H, J 7.8 Hz), 7.84 (d, 4H, J = 6.

2 Hz), 7.27 (t, 2H, J = 7.8 Hz), 6.91 (t, 1H, J = 7.8 Hz), 3.98 (q, 2H, J = 7.0 Hz), 2.37 (s, 6H), 1.40 (t , 3H, J = 7.0 Hz)

MS (APCI, m / z): 482 (M + l) +

 HPLC (reversed): Rt. (Min) = 2.07 Example 762

 1- (4-methylsulfamoylofenyl) -triethanone N- (2- (2-methoxyanilino) -1-5-methyl-6- {2- [1- (4-methylsulfamoylofenyl) ethylidene ] Hid Radino} -4-pyrimidini

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 666 (M + l) +

HPLC (reversed): Rt. (Min) = 4.14 Example 763

l- (4-Methylsulfamoylphenyl)-1-ethanone- (2- (2-methoxyanilino) -1-5-propyl-6- {2- [1- (4-methylsulfamoylylenyl) ) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

'H-NMR spectrum _{(270 MHz, DMSO- d 6)} δ ριη: 9.15-9.08 (m, 1H), 9.07 (brs, 2H), 8.09 (d, 4H, J = 8.4 Hz), 7.84 (d, 4H , J = 8.4 Hz), 7.55-7.48 (m, 2H), 7.41 (s, 1H), 7.10-6.85 On, 3H), 3.91 (s, 3H), 2.97-2.87 (m, 2H), 2.45 (d , 6H, J = 4.9 Hz), 2.40 (s, 6H), 1.70-1.55 (m, 2H), 0.98 (t, 3H, J = 7.3 Hz)

MS (APCI, m / z): 694 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.38 Example 764

 1- (4-Methylsulfamoylofenyl) -toluenone N- (2- (2-Methoxy-5-methylanilino) -1-6- {2- [1- (4-methylsulfamoyl-phenyl) ) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 666 (M + D +

 HPLC (reversed): Rt. (Min) = 4.40. Example 765

U- (4-methylsulfamoylophenyl)-1-ethanone N- (2- (2-ethoxyanilino)-1- {2- [卜 (4-methylsulfamoylophenylyl) ethylidene] Hydrazino 4 -pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

-Awake R spectrum (270 MHz, DMSO- d ₆ ) (5 pm: 10.14 (brs, 2H), 8.96-8.88 (m, 1H), 8.06 (d, 4H, J = 8.4 Hz), 7.82 (d, 4H) , J = 8.4 Hz), 7.48-7.38 (m, 3H), 7.04-6.88 (m, 3H), 6.65 (s, 1H), 4.14 (q, 2H, J = 7.0 Hz), 2.46 (d, 6H, J = 4.6 Hz), 2.39 (s, 6H), 1.42 (t, 3H, J = 7.0, Hz)

MS (APCI, m / z): 666 (Mll) +

HPLC (reversed): Rt. (Min) = 4.42 Example 766

l- (4-Methylsulfamoylene) -1--1-ethanone N- (2- (2-methoxy-5-phenylanilino) -1-6- (2- [1- (4-methylsulfamoylofyl) Enil) ethylidene] hydrazino}-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 728 (M + l) +

HPLC (reversed): Rt. (Min) = 4.81 Example 767

Tri (4-methylsulfamoylofenyl) -triethanone N- (2- (2-methoxy-5-t-butylanilino)-6- {2- [1- (4-methylsulfamoylofenyl) ethylide N] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 708 (M + D +

HPLC (reversed): Rt. (Min) = 4.88 Example 768

Tri (4-methylsulfamoylofenyl) -triethanone N- (2- (2-methoxy-5-trifluoromethylanilino) -1-6- {2- [1- (4-methylsulfa Moylufenyl) e tyriden] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 720 (M + l) +

HPLC (reversed): Rt. (Min) = 4.89 Example 769

 1- (4-methylsulfamoylofenyl) -triethanone N- (2- (2-fluoro-4--4-methylylanilino)-6- {2- [1- (4-methylsulfamoylofenyl) ethylidene ] Hydrazino}-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) 5 pm: 9.91 (brs, 2H), 8.17 (t, 1H, J = 8.4 Hz), 8.04 (d, 4H, J = 8.6 Hz), 7.81 (d , 4H, J = 8.6 Hz), 7.71 (brs, 1H), 7.50-7.40 (m, 2H), 7.10-6.94 (m, 2H), 6.63 (s, 1H), 2.46 (br s, 6H), 2.37 (s, 6H), 2.31 (s, 3H)

MS (APCL m / z): 654 (Mll) +

 HPLC (reversed): Rt. (Min) = 4.40 'Example 770

Tri (4-methylsulfamoylofenyl) -triethanone N- (2- (2,6-difluora nilino) -1-6- {2- [1- (4-methylsulfamoyl-phenyl) ethylidene] hydrazino } -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 658 (M + D +

HPLC (reversed): Rt. (Min) = 4.20. Example 771

 1- (4-Methylsulfamoyl-phenyl) -triethanone N- (2_ (2,3,4-trifluoroalumino) -1-6- {2- [tri (4-methylsulfamoyl-phenyl) ethylidene ] Hyd Radino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (19 rag, 28%). E -丽R spectrum _{(270 MHz, DMS0 - d 6} ) <5 pm: 9.92 (s, 2H), 8.28 (s, 1H), 8.

02 (d, 4H, J = 8.4 Hz), 7.91-7.89 (m, 1H), 7.80 (d, 4H, J = 8.4 Hz), 7.47-7.45 (m, 2H), 7.28-7.24 (m, 1H), 6.64 (s, 1H), 2.45 (d, 6H, J = 4.9 Hz), 2.36 (s, 6H) MS (APCI, m / z): 676 (M + l

 HPLC (reversed): Rt. (Min) = 4.59. Example m

1- (4-Methylsulfamoylofenyl)-1-ethanone N-(2- (4-Methylanilino) -1- 6_ {2_ [1- (4-Methylsulfamoyl-phenyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 636 (M + l) +

HPLC (reversed): Rt. (Min) = 4.33. Example m

 1- (4-methylsulfamoylofenyl) -triethanone N- (2- (2-fluoro-5-methylanilino) -6-{2- [1- (4-methylsulfamoyl-phenyl) ethylidene] h Drazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

'H-NMR spectrum _{(270 MHz, DMS0 - d 6} ) <5ppm: 9.96 (brs, 2H), 8.14 (t, 1H, J = 8.4 Hz), 8.04 (d, 4H, J = 8.4 Hz), 7.80 ( d, 4H, J = 8.4 Hz), 7.70 (brs, 1H), 7.52-7.42 (m, 2H), 7.09 (dd, 1H, J = 8.4, 11.1 Hz), 8.87-6.80 (m, 1H), 6.64 (s, 1H), 2.45 (brs, 6H), 2.37 (s, 6H), 2.33 (s, 3H) MS (APCI, m / z): 654 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.39. Example 774

1- (4-Methylsulfamoylofenyl) -1 -ethanone N- (2- (2-Fluoro-4-cyclooctane) — 6- {2- [1- (4-Methylsulfamoyl-1 Phenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were conducted in the same manner as in Example 561, to obtain the desired product (43 mg, 64%). Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.97 (s, 2H), 8.42 (t, 1H, J = 8.9 Hz), 8.03 (d, 4H, J = 8.4 Hz), 7.97 (s, 2H), 7.81 (d, 4H, J = 8.4 Hz), 7.47-7.44 (in, 2H), 7.22 (d, 1H) , J = 9.5 Hz), 6.65 (s, 1H), 2.45 (d, 6H, J = 4.6 Hz), 2.37 (s, 6H)

MS (APCI, m / z): 674 (M + 1) +,

HPLC (reversed): Rt. (Min) = 4.70. Example 775

 1- (4-Methylsulfamoyl-phenyl) -triethanone N- (2- (2-phenylethylamino) 1-6- {2- [1- (4-Methylsulfamoyl-phenyl)

No} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (

MS (APCI, m / z): 650 (M + D +

HPLC (reversed): Rt. (Min) = 4.33. Example 776

 1_ (4-Methylsulfamoylofenyl) -Torenonon N- (2- (2-Fluoro-3-co-mouth Loirino) 1 6- {2- [1- (4-Methylsulfamoyl-) Phenyl) ethylidene] hydrazino} -4-pyrimidini J レ) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 674 (M + l) +

HPLC (reversed): Rt. (Min) = 4.78 Example 777

 1- (4-Methylsulfamoylofenyl) -triethanone N_ (2-phenyl-6- {2- [1- (4-Methylsulfamoylofenyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή-NMR spectrum, Torr (270 MHz, DMSO-d ₆ ) 5 ppm: 10.30 (brs, 2H), 8.48-8.40 (m, 2H), 8.07 (d, 4H, J = 8.6 Hz), 7.83 (d , 4H, J = 8.6 Hz), 7.60-7.35 (i, 5H), 7.04 (s, 1H), 2.47 (brs, 6H), 2.43 (s, 6H)

MS (APCI, m / z) 607 (M + D +

HPLC (reversed) Rt. (Min) = 5.15 Example 778

 1- (4-methylsulfamoyl-phenyl)-1-ethanone N- (2- (4-tolylmethyl) -1-6- (2- [1- (4-methylsulfamoylofenyl) ethylidene] Hydrazino} -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z) 635 (M + D +

 HPLC (reversed) Rt. (Min) = 4.38. Example 779

 1- (4-Methylsulfamoyl-1-phenyl) -triethanone N- (2- (2-naphthyl) -6- {2- [2- (1- (4-methylsulfamoylofenyl) ethylidene] hydrazino} -4 -Pirimi zinile) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z) 657 (M + 1) +

HPLC (reversed) Rt. (Min) = 6.02 Example 780

 1- (4-methylsulfamoylofenyl) -ethanone N- (2- (3,4-dichloroanilino) -1-6- (2- [1- (4-methylsulfamoylofenyl)

-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z) 690 (M + D +

HPLC (reversed) Rt. (Min) = 4.97 Example 781 5216

270

1- (4-methylsulfamoylofenyl) -triethanone N- (2- (3-biphenylamino) -1-6- {2- [tri (4-methylsulfamoylofenyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, ffl / z): 698 (M + l) +

 HPLC (reversed): Ri. (Min) = 4.74 Example 782 ■

 1- (4-Methylsulfamoylofenyl) -triethanone N- (2- (3-chloroanilino) -1-6- {2- [2- (4-methylsulfamoylofenyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή-丽 R spectrum (270 MHz, DMS0-d ₆ ) δρρηι: 9.89 (brs, 2H), 9.03 (s, 1H), 8.14 (brs, 1H), 8.07 (d, 4H, J = 8.6 Hz), 7.96 (d, 1H, J = 8.1 Hz), 7.81 (d, 4H, J = 8.6 Hz), 7.52-7.2 (m, 2H), 7.28 (t, 2H, J = 8.1 Hz), 6. 94 (d, 1H, J = 8.1 Hz), 6.63 (s, 1H), 2.45 (d, 6H, J = 4.3 Hz), 2.39 (s, 6H)

 MS (APCI, lii / z): 656 (M + l) i

HPLC (reversed): Ri. (Min) = 4.55 Example 783

Tri (4-methylsulfamoylniphenyl) -triethanone N- (2- (3-methylanilino) -1- 6_ {2- [tri (4-methylsulfamoylunophenyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 636 (M + l

HPLC (reversed): Rt. (Min) = 4.32. Example 784 卜 (4-Methylsulfamoylofenyl) -1 -ethanone N- (2- (3-Methoxyanilino) —6- {2- [卜 (4-Methylsulfamoyl-phenyl) ethylidene] hydrazino}-4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 652 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.23. Example 785

 1- (4-Methylsulfamoyl-1-phenyl) -triethanone N- (2- (3-Trifluorometylarilino) -1-6- (2- [1- (4-Methylsulfamoylofenyl) ethylidene] h Drazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 690 (M + l) +

HPLC (reversed): Rt. (Min) = 4.70. Example 786

U- (4-methylsulfamoyl-phenyl) -toluene non-N- (2- (3-t-butylylanilino) -1-6- (2- [1- (4-Methylsulfamoylofenyl) ethylidene] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 678 (M + l) +

HPLC (reversed): Rt. (Min) = 4.37 Example 787

1- (4-methylsulfamoylofenyl) -triethanone- (2- (3-trifluoromethyloxyanilino) —6- {2- [1- (4-methylsulfamoylofenyl) ethylidene] hydrazino} -4 -Pyrimidinile) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 706 (M + l) + HPLC (reversed) Rt. (Min) = 4.97 Example 788

 1- (4-methylsulfamoylofenyl) -triethanone N- (2-phenylthiomethyl-1-6- [2-[(4-methylsulfamoylofenyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z) 653 (M + D +

HPLC (reversed) Rt. (Min) = 4.48. Example 789

 1- (4-Methylsulfamoylofenyl) -triethanone N_ (2_phenoxymethyl-6- {2- [1- (4-methylsulfamoylofenyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z) 637 (M + l) +

HPLC (reversed) Rt. (Min) = 4.776 Example 790

 1- (4-Methylsulfamoylofenyl)-1-ethanone N- (2- (3-nitroanilino) -1-6- (2- [1- (4-Methylsulfamoylofenyl) ethylidene] Hydrazino} -4 -pyrimidinyl) hydrazone

The reaction was conducted in the same manner as in Example 561, and purification was performed to obtain the desired product (46 mg, 69%). Ή-丽 R spectrum (270 MHz, DMS0-d ₆ ) δρρπι 9.93 (s, 2H), 9.39 (s, 1H), 8.72 (d, 1H, J = 8.4 Hz), 8.05 (d, 4H, J = 8.4 Hz), 7.71 (d, 4H, J-8. Hz), 7.77-7.73 (m, 1H), 7.58-7.45 (m, 2H), 6.66 (s, 1H), 2.45 (d, 6H, J

= 4.9 Hz), 2.40 (s, 6H)

MS (APCI, m / z) 667 (M + 1) +

HPLC (reversed) Rt. (Min) = 4.84 Example 791

 1- (4-Methylsulfamoylofenyl) -triethanone N-C2- (3-phenoxyanilino) 1 6- {2- [1- (4-Methylsulfamoylofenyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone-Reaction was carried out in the same manner as in Example 56 1, followed by purification to obtain the desired product.

MS (APCI, m / z): 714 (M + l) +

HPLC (reversed): Rt. (Min) = 4.90 Example 792

l- (4-Methylsulfamoylofenyl) -1 -ethanone N- (2- (3-methylthioanilino) — 6_ {2- [1- (4-Methylsulfamoylofenyl) ethylidene] hydrazino } -4-pyrimidinylile) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 668 (M + D +

HPLC (reversed): Rt. (Min) = 4.79 Example 793

l- (4-methylsulfamoylofenyl) -1-ethanone N- (2- (3-trifluoromethylthiothioanilino) — 6- {2- [2- (4- (4-methylsulfamoylofenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 722 (M + l) +

HPLC (reversed): Rt. (Min) = 4.66. Example 794

1- (4-methylsulfamoylophenyl) -1- ethanone N- (2- (3- (N-hexyl-1-N-methylcarbamoyl) anilino) -1-6- {2- [1- (4 -Methylsulfamoyl-phenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 763 (M + 1) +

HPLC (reversed): Rt. (Min) = 4.89 Example 795

Tri (4-methylsulfamoyl-phenyl) _1-ethanone N- (2- (4- {N-hexyl-1-N-methylcarbamoyl} anilino) -1 6- {2- [1- (4-methylsulfamoyl- Phenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 763 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.83 Example 796

 1- (4-Methylsulfamoyl-1-phenylyl) -triethanone N- (2- (3-tetrafluoroethoxyethoxylinino) -1-6- (2-D- (4-methylsulfamoyl-phenyl) ethylidene ] Hydrazino}-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 738 (M + D +

HPLC (reversed): Rt. (Min) = 4.43 Example 797

Tri (4-methanesulfonylphenyl) -2,2,2-trifluoro-1-ethanone N- (2-anilino-6- {2- [1- [4- (4-methanesulfonylphenyl) -2,2 2-trifluoroethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 700 (M + l) +

HPLC (reversed): Rt. (Min) = 5.55 Example 798 1- (4-Methanesulfonylphenyl)-1-ethanone N- (2-anilino-5-ethoxy-1 6- {2-[((4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

-NMR spectrum (270 MHz, DMS0 ~ d ₆ ) δ ρπι: 9.14 (brs, 3H), 8.18 (d, 4H, J = 8.6 Hz), 8.18 (d, 2H, J = 8.1 Hz), 8.00 (d, 4H, J = 8.6 Hz), 7.28 (t, 2H, J = 8.1 Hz), 6.93 (t, 1H, J = 8.1 Hz), 4.01 (q, 2H, J = 7.0 Hz), 3.28 (s, 6H) , 2.42 (s, 6H), 1.42 (t, 3H, J = 7.0 Hz)

MS (APCI, m / z): 636 (M + l

HPLC (reversed): Rt. (Min) = 3.90. Example 799

 1- (4-methylsulfamoylofenyl) -triethanone N- (2-anilinol-5_ethoxy-1-6- (2-[(4-methylsulfamoylofenyl) ethylidene] hydrazino} -4-pyrimidinyl ) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή-wake R spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.10 (s, 2H), 8.17-8.08 (m, 7 H), 7.84 (d, 4H, J = 8.4 Hz), 7.55-7.47 ( q, 2H, J = 4.6 Hz), 7.25 (t, 2H, J = 7.6 Hz), 6.92 (t, 1H, J = 7.6 Hz), 3.99 (q, 2H, J = 7.0 Hz), 2.4 5 ( d, 6H, J = 4.6 Hz), 2.41 (s, 6H), 1.41 (t, 3H, J = 7.0 Hz)

MS (APCI, m / z): 666 (M + l) +

HPLC (reversed): Rt. (Min) = 3.91. Example 800

l- (4-pyridyl) -triethanone N- (2- (3-methyl-4-fluoroarylanilino) -6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) 5 pm: 9.97 (brs, 2H), 8.74 (s, 1H), 8.65 (d, 4H, J = 6.2 Hz), 7.90-7.80 (m, 1H) , 7.79 (d, 4H, J = 6.2 Hz), 7.78-7.70 (m, 1H), 7.01 (dd, 1H, J = 9.2, 9.2 Hz), 6.70 (s, 1H), 2.35 (s, 6H), 2.24 (s, 3H) ''

 MS (APCI, m / z): 470 (Mil) +

 HPLC (reversed): Rt. (Min) = 3.01. Example 801

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (3-Methyl-4-1-fluoroanilino) -6- {2-[(4- (4-Methanesulfonylphenyl) ethylidene] hydrazinoto 4-pyrimidinyl) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

-NMR spectrum _{(270 MHz, DMS0-d 6} ) δ ριιι: 9.91 (brs, 2H), 8.73 (s, 1H), 8.09 (d, 4H, J = 8.4 Hz), 7.97 (d, 4H, J = 8.4 Hz), 7.91-7.84 (m, 1H), 7.75-7.70 (m, 1H), 7.02 (dd, 1H, J = 9.2, 9.2 Hz), 6.65 (s, 1H), 3.26

(s, 6H), 2.39 (s, 6H), 2.24 (s, 3H)

MS (APCI, m / z): 624 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.03 Example 802

 1- (4-Methylsulfo τmoylphenyl)-1-ethanone Ν- (2- (3-Methyl-14-fluoroanilino)-6_ {2- [1- (4-Methylsulfamoylphenyl) ethylidene] hydra Zino}-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

¾- 丽! Spectrum (270 MHz, DMS0-d ₆ ) δ ρηι: 9.83 (brs, 2H), 8.74 (s, 1H), 8.15 (d, 4H, J = 8.4 Hz), 7.92-7.70 (m, 2H ), 7.81 (d, 4H, J-8.4 Hz), 7.48 (q, 2H, J = 4.9 Hz), 7.01 (dd, 1H, J = 9.2, 9.2 Hz), 6.61 (s, 1H), 2.46 (d , 6H, J = 4.9 Hz), 2.39 (s, 6H), 2.24 (s, 3H)

MS (APCI, m / z): 654 (M + l) +

HPLC (reversed): Rt. (Min) = 4.04. Example 803

 1- (4-Methylsulfamoylphenyl)-1-ethanone N- (2- (3,5-difluoroallylino) -6- {2- [tri (4-methylsulfamoylphenyl) ethylidene] Hydrazino}-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Awake R spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 9.96 (brs, 2H), 9.29 (s, 1H), 8.08 (d, 4H, J = 8.4 Hz), 7.90-7.85 (m, 2H), 7.80 (d, 4H, J = 8.4 Hz), 7.52-7.40 (m, 1H), 6.72-6.62 (m, 2H), 6.62 (s, 1H), 2.49-2.44 (m, 6H), 2.39 (s, 6H )

 MS (APCI, m / z): 658 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.53. Example 804

Tri (4-methylsulfamoylphenyl)-1-ethanone N-(2- (3,4,5-tritrifluoroanilino) -6- {2- [1- (4-methylsulfamoylphenyl)) ethylidene ] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ριιι: 9.97 (brs, 2H), 9.26 (s, 1H), 8.10-8.01 (m, 6H), 7.81 (d, 4H, J = 8.4 Hz), 7.53-7.45 (m, 2H), 6.63 (s, 1H), 2.45 (d, 6H, J = 4.1 Hz), 2.40 (s, 6H)

MS (APCI, m / z): 676 (M + l) +

HPLC (reversed): Rt. (Min) = 4.67. Example 805

1- (4-Methylsulfamoylphenyl) -1_ethanone N_ (2-anilino-5-benzyl-6_ {2- [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 712 (M + l) + TJP03 / 05216

278

HPLC (reversed): Rt. (Min) = 4.43 _c Example 806

 1- (4-ethanesulfonylphenyl) -1_ethanone N- (2- (2-methyl-5-fluoroanilino) -6- {2- [tri (4-ethanesulfonylphenyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (18 mg, 36%). MS (APCI, m / z): 652 (M + D +

HPLC (reversed): Rt. (Min) = 4.44 ₀ Example 807

 1- (4-methylsulfamoylphenyl) -thuetanone- (2- (3-bromoanilino)

-6- {2- [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino}-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή-Band R spectrum (270 MHz, DMSO- d ₆ ) δρριη: 9.89 (brs, 2H), 9.01 (s, 1H), 8.16-8.07 (m, 2H), 8.06 (d, 4H, J-8.4 Hz) , 7.81 (d, 4H, J = 8.4 Hz), 7.53-7.44 (m, 2H), 7.22 (t, 1H, J = 8.1 Hz), 7.08 (d, 1H, J = 8.1 Hz), 6.63 (s, 1H), 2.45 (d, 6H, J = 3.2 Hz), 2.38 (s, 6H)

 MS (APCI, m / z): 700 (M + D +

 HPLC (reversed): Rt. (Min) = 4,34. Example 808

1- (4-; enyl) -triethanone N- (2- (4-bromoanilino)

-6- {2- [1- (4-enyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 9.87 (brs, 2H), 9.01 (s, 1H), 8.05 (d, 4H, J = 8.4 Hz), 7.99 (d, 2H, J = 8.9 Hz), 7.82 (d, 4H, J = 8. 4 Hz), 7.52-7.48 (ra, 2H), 7.40 (d, 2H, J = 8.9 Hz), 6.63 (s, 1H), 2.45

(brs, 6H), 2.39 (s, 6H)

 MS (APCI, m / z): 700 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.30. Example 809

l- (4-Methylsulfamoylphenyl)-1-ethanone N- (2- (3,4-difluoroalinoline) -6- {2- [1- (4-methylsulfamoylphenyl) ) Ethylidene] hydrazino} 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

'H-NMR spectrum (270 MHz, DMSO-d ₆ ) δρριη: 9.91 (brs, 2H), 9.10 (s, 1H), 8.65-8.50 (m, 1H), 8.07 (d, 4H, J = 8.4 Hz) , 7.81 (d, 4H, J = 8.4 Hz), 7.52-7.46 (m, 3H), 7.34-7.24 (m, 1H), 6.62 (s, 1H), 2.45 (d, 6H, J = 5.

1 Hz), 2.39 (s, 6H)

MS (APCI, m / z): 658 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.26. Example 810

 1- (4-Methylsulfamoylphenyl)-1-ethanone N- (2- (3-fluoro-4-methylthiarilino) -6- {2- [1- (4-methylsulfamoylphenyl) ) Ethylidene] hydrazino}-4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product. .

'H-NMR spectrum _{(270 MHz, DMSO- d 6)} <5 pm:. 9.88 (brs, 2H), 8.93 (s, 1H), 8.07 (d, 4H, J = 8.6 Hz), 7.84-7.78 (m , 1H), 7.80 (d, 4H, J '= 8.6 Hz), 7.52-7.40 (m, 3H), 7.15-7.05 (m, 1H), 6.60 (s, 1H), 2.44 (brs, 6H), 2 . 39 (s, 6H), 2.19 (s, 3H)

MS (APCI, m / z): 654 (M + D +

HPLC (reversed): Rt. (Min) = 4.20. ' Example 811

 1_ (4-Methanesulfinylphenyl) -1 -ethanone N- (2-anilino-6- {2- [1- (4-Methanesulfenylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazo In

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 560 (M + l) +

HPLC (reversed): Rt. (Min) = 3.38 Example 812

卜 (4-pyridyl) -1 -ethanone N-(2-anilino-5-anilino-6- {2- [卜 (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 529 (M + l) +

HPLC (reversed): Rt. (Min) = 3.18 Example 813

 1- (4-Methanesulfonylphenyl) -triethanone N- (2-anilino-5-anilino-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} _4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 683 (M + D +

HPLC (reversed): Rt. (Min) = 4.42 Example 814

Tri-α-methanesulfonyl 1H-pyrrol-3-yl) -triethanone Ν- (2-anilino-6- {2- [1- (trimethansulfonyl 1H-pyrrol-3-yl) ethylidene) ] Hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 570 (M + l) + HPLC (reversed): Rt. (Min) = 4.05. Example 815

 1- (4_ethanesulfonyl 2,3-dichlorophenyl) -triethanone N- (2-anilino-6- {2- [1- (4-ethanesulfonyl 2,3-dichlorophenyl) ethylidene] hydrazino 4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561, and the desired product was obtained as a mixture. MS (APCI, m / z): 756 (M + D +

HPLC (reversed): Rt. (Min) = 5.17 and 5.38 Example 816

 1- (trimethanesulfonyl 1H-pyrrole-3_yl)-1-ethanone N- (2- (3-fluora nilino) -6-{2-[1_ (1-methanesulfonyl 1H-pyrrolyl-3) -Zino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 588 (M + l) +

HPLC (reversed): Rt. (Min) = 4.48 Example 817

Tri (4-benzenesulfinylphenyl) -toluenenon-N- (2-anilino-6- {2-[(4- (benzenesulfinylphenyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 684 (+ D +

HPLC (reversed): Rt. (Min) = 4.66 Example 818

Tri (4_pyridyl) -1 -ethanone N- (2-anilino-5-methoxy-6- {2- [1- (4-pyridyl

•-4-Pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 468 (M + D +

HPLC (reversed): Rt. (Min) = 2.72 Example 819

 1- (4-methylsulfonylphenyl) -triethanone N- (2-anilinol 5 _methoxy-6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino}-4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 622 (M + l) +

 HPLC (reversed): Rt. (Min) = 3.95. Example 820

 1- (4-pyridyl) -triethanone N- (2- (2,2-difluoro-benzo [1,3] dioxol-5-yl) -6- {2- [1- (4-pyridyl) [Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 518 (M + l) +

HPLC (reversed): Rt. (Min) = 3.40 Example 821

l- (4-Methanesulfonylphenyl) -triethanone N- (2- (2,2-difluoro-benzo [1,3] dioxol-5-yl) -6- {2- [1- (4 -Mesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 672 (M + l) +

HPLC (reversed): Rt. (Min) = 4.64 Example 822 1- (4-Methylsulfamoylphenyl) -toethanone N- (2- (2,2-difluoro-benzo [1,3] dioxol-5-yl) -6- {2- [1 -(4-Methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 702 (M + D +

 HPLC (reversed): Rt. (Min) = 4.65 Example 823

1_ ₍₄ _ cyclopropyl sulfamoyl Hue sulfonyl) - Bok ethanone _N-(2 - ₍₂ one Furuoro Anirino) -6- {2- [Bok (4-cyclopropyl-sulfamoyl Hue sulfonyl) Echiriden] arsenide Drazino} -4-pyrimidini) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ppm: 9.96 (brs, 2H), 8.53-8.45 (m, 1H), 8.05 (d, 4H, J-8.6 Hz), 7.91 (brs, 1H) , 7.84 (d, 4H, J = 8.6 Hz), 7.77 (brs, 1H), 7.26-7.13 (m, 2H), 7.10-7.00 (m, 1H), 6.64 (s, 1H), 2.38 (s, 6H), 2.23-2.10 (m, 2H), 0.54-0.46 (m, 4H), 0.44-0.34 (m, 4H) MS (APCI, m / z): 692 (M + D +

HPLC (reversed): Rt. (Min) = 4.58 Example 824

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (1-andrenyl) -6- {2-methansulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (39 mg, 81%). 'Η-band R spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 10.07 (s, 2H), 8.78 (d, 1H, J = 8.4 Hz), 8.11 (d, 4H, J = 8.5 Hz), 7.98 ( d, 4H, J: 8.5 Hz), 7.20 (t, 2H, J = 5.7 Hz), 6.90 (t, 1H, J = 7.4 Hz), 6.68 (s, 1H), 4.22 (t, 2 H, J = 8.7 Hz), 3.27 (s, 6H), 3.15 (t, 2H, J = 8.7 Hz), 2.42 (s, 6H) MS (APCI, m / z): 618 (M + l HPLC (reversed): Rt. (Min) = 5.09. Example 825

Tri (4-methylsulfamoylphenyl) -triethanone N- (2-anilino-5-methoxy-6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4-pi Limidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριη: 9.21 (brs, 2H), 9.09 (s, 1H), 8.14 (d, 2H, J = 7.6 Hz), 8.12 (d, 4H, 8.1 Hz) , 7.84 (d, 4H, J = 8.1 Hz), 7.56-7.47 (m, 2H), 7.25 (t, 2H, J = 7.6 Hz), 6.92 (t, 1H, J = 7.6 Hz), 3.78 ( s, 3H), 2.45 (d, 6H, J = 4.3 Hz), 2.42 (s, 6H)

MS (APCI, m / z): 652 (M + D +

HPLC (reversed): Rt. (Min) = 3.98. Example 826

 1- (4-Methylsulfamoylphenyl) -toethanone-(2- (3_Fluoroanilino) -6- {2- [2- (1- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4 -Pirimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (31 mg, 49 °). Ή -Awake R spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.92 (s, 2H), 9.09 (s, 1H),

8.33 (d, 1H, 11.1 Hz), 8.08 (d, 4H, J = 8.5 Hz), 7.81 (d, 4H, J = 8.

5 Hz), 7.57-7.45 (m, 3H), 7.26 (q, 1H, J = 8.1 Hz), 6.76 (t, 1H, J = 8.

1 Hz), 6.62 (s, 1H), 2.45 (d, 6H, J = 4.9 Hz), 2.39 (s, 6H)

 MS (APCI, m / z): 640 (M + D +

HPLC (reversed): Rt. (Min) = 4.29. Example 827

l- (4-Methylsulfamoylphenyl) -triethanone N- (2- (4-fluorosulfoylphenyl) -6- {2- [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino}- 4-pi 0305216

285 Limidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (7 mg, 13%).

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) (5 ppm: 9.84 (brs, 2H), 8.87 (s, 1H), 8.10 (d, 4H, J = 8.1 Hz), 8.06-7.97 (m, 2H) , 7.82 (d, 4H, J = 8.1 Hz), 7.48 (q, 2H, J = 5.1 Hz), 7.09 (dd, 2H, J = 8.9, 8.9 Hz), 6.62 (s, 1H), 2.46 (d, 6H, J = 5.1 Hz), 2.39 (s, 6H)

 MS (APCI, m / z): 640 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.09. Example 828

 1- (4-Methylsulfamoylphenyl) -1 -ethanone N- (2- (benzo [1,3] dioxol-5-yl-amino) -6- {2- [1- (4- Methylsulfamoylphenyl) ethylidene] hydrazino} _4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (21 mg, 32%). Ή-wake R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 9.83 (brs, 2H), 8.69 (s, 1H),

8.05 (d, 4H, J = 8.4 Hz), 7.96 (brs, 1H), 7.81 (d, 4H, J = 8.4 Hz), 7.48 (brs, 2H), 7.21 (d, 1H, J = 8.4 Hz ), 6.81 (d, 1H, J = 8.4 Hz), 6.57

(s, 1H), 5.98 (s, 2H), 2.45 (brs, 6H), 2.38 (s, 6H)

 MS (APCI, m / z): 666 (Mll) +

 HPLC (reversed): Rt. (Min) = 4.01. Example 829

 1- (4-pyridyl) -triethanone N- (2- (3,5-dimethoxyanilino) -6- {2- [tri (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product (13 mg, 26%). -Band R spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 9.97 (brs, 2H), 8.73 (s, 1H),

8.64 (d, 4H, J = 6.2 Hz), 7.80 (d, 4H, J = 6.2 Hz), 7.51 (s, 2H), 6.69

(s, 1H), 6.11 (s, 1H), 2.35 (s, 6H)

MS (APCI, m / z): 498 (M + l) + HPLC (reversed): Rt. (Min) = 3.03. Example 830

 1- (4-Methanesulfonylphenyl) -triethanone N- (2- (3,5-dimethoxyanilino) -6- {2- [tri (4-methanesulfoerphenyl) ethylidene] hydrazino} -4-pyrimino Jinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 652 (M + D +

HPLC (reversed): Rt. (Min) = 4.09 Example 831

Tri (4-methylsulfamoylphenyl) -triethanone N_ (2- (3,5-dimethoxyanilino) -6- {2- [1- [4- (4-methylsulfamoylphenyl) ethylidene] hydrazino 4-pyrimidinyl ) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 682 (M + D +

HPLC (reversed): Rt. (Min) = 4.14 Example 832

 1- (4-pyridyl) -1 1-ethanone N- (2- (3,4,5-trimethoxyanilino) -6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 528 (M + D +

HPLC (reversed): Rt. (Min) = 2.82 Example 833

1_ (4-Methanesulfonylphenyl) -triethanone N- (2- (3,4,5-trimethoxyanilino) -6- {2- [1- [4-Methanesulfonylphenyl: • 4-pyrimigere) Hydrazone Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product

MS (APCI, m / z): 682 (M + D +

HPLC (reversed): Rt. (Min) = 3.88 Example 834

Tri (4-methylsulfamoylphenyl) -triethanone N_ (2- (3,4,5-trimethoxyanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethyli '

ノ} -4-pyrimidinile) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 712 (M + l

HPLC (reversed): Rt. (Min) = 3.90. Example 835

 1-(4-Methylsulfamoylphenyl) -triethanone-(2- (2,4-difluoroalinylino) -6_ {2- [1_ (4-methylsulfamoylphenyl) ethylidene] hydrazino 4 -Pyrimidinile) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (40 rag, 64 °). -R spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 9.90 (s, 2H), 8.26-8.17 (m,

1H), 8.03 (d, 4H, J = 8.6 Hz), 7.92 (s, 1H), 7.81 (d, 4H, J = 8.6 Hz), 7.46 (d, 2H, J = 4.3 Hz), 7.33-7.25 ( m, 1H), 7.09-7.01 (m, 1H), 6.63 (s, m), 2.46 (d, 6H, J = 3.5 Hz), 2.36 (s, 6H)

 MS (APCI, m / z): 658 (M + lH

 HPLC (reversed): Rt. (Min) = 4.34. Example 836

 1- (4-phenyl) -1-ethanone N- (2- (2-methoxyanilino) -6- {2- [1- (44-pyrimidinyl) hydrazone ·

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product. 'H-NMR spectrum (270 MHz, DMSO-d ₆ ) <5 pm: 10.11 (brs, 2H), 8.82-8.92 (m, 1H), 8.06 (d, 4H, J = 8.6 Hz), 7.82 (d, 4H, J = 8.6 Hz), 7.50-7.39 (m, 3H), 7.05-6.93 (m, 3H), 6.64 (s, 1H), 3.91 (s, 3H), 2.46 (brs, 6H), 2.39 (s , 6H)

MS (APCI, m / z): 652 (M + D +

 HPLC (reversed): Ri. (Min) = 4.03. Example 837

l- (4-Acetylsulfamoylphenyl) -1-ethanone N- (2-anilino-6- {2-Cl (4-acetylsulfamoylphenyl) ethylidene] hydrazino} _4-pyrimidinyl) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 678 (M + D +

HPLC (reversed): Rt. (Min) = 4.33. Example 838

 1- (4-Methylsulfamoylphenyl) -1-ethanone-(2- (2-Fluoro-5-octaluminirino) -6- {2- [1- (4-Methylsulfamoylphenyl) ) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

The reaction was carried out in the same manner as in Example 561, followed by purification to obtain the desired product (17 mg, 46 mg). 'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 10.05 (s, 2H), 8.64 (brs, 1,), 8.06 (d, 4Η, J = 8.4 Hz), 7.91 (d, 1H, J = 2.4 Hz), 7.80 (d, 4H, J = 8.4 Hz), 7.48 (brs, 2H), 7.29 (dd, 1H, J = 8.8, 10.9 Hz), 7.09-7.04 (m, 1H), 6.66 ( s, 1H), 2.45 (s, 6H), 2.38 (s, 6H)

MS (APCI, m / z): 674 (M + D +

 HPLC (reversed): Rt. (Min) = 4.87. Example 839

1- (4-methylsulfamoylphenyl)-1-ethanone N- (2- (4-chloroanilino) -6- {2- [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561, to obtain the desired product (42 mg, 63%). Ή-NMR spectrum _{(270 MHz, DMS0-d 6} ) δ ριη: 9.86 (s, 2H), 9.00 (s, 1H), 8.55 (d, 4H, J - 8.6 Hz), 8.03 (d, 2H, J = 8.6 Hz), 7.81 (d, 4H, J = 8.6 Hz), 7.47 (brs, 2H), 7.28 (d, 2H, J = 8.6 Hz), 6.23 (s, 1H), 2.46 (s, 6H) , 2.39 (s, 6H),

MS (APCI, m / z): 656 (M + l

HPLC (reversed): Rt. (Rain) = 4.91. Example 840

 1- (4-Methylsulfamoylphenyl) -1-ethanone N- (2- (1-Indolinyl) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino 4 -Pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561, to obtain the desired product (16 mg, 30%). 'H-NMR spectrum (270 MHz, DMSO- d ₆ ) δ ριη: 9.99 (s, 2H), 8.79 (d, 1H, J

= 7.6 Hz), 8.07 (d, 4H, J = 8.6 Hz), 7.82 (d, 4H, J = 8.6 Hz), 7.47 (dd, 2H, J = 5.1 Hz, 10.0 Hz), 7.18 (t, 2H, J = 8.0 Hz), 6.89 (t, 1H, J =

6.8 Hz), 6.63 (s, 1H), 4.22 (t, 2H, J = 8.6 Hz), 3.14 (t, 2H, J = 8.6 Hz), J.46 (d, 6H, J = 4.9 Hz), 2.40 (s, 6H)

MS (APCI, m / z): 648 (M + lH

HPLC (reversed): Rt. (Min) = 5.50. Example 841

 1- (4-Methylsulfamoylphenyl) -triethanone N- (2-anilino-5-methyl-6- {2_ [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino 4-pyrimidinyl) Hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (32 mg, 60%). MS (APCI, m / z): 636 (M + D + HPLC (reversed): Rt. (Min) = 4.09 Example 842

 1- (4-Methylsulfamoylphenyl) -triethanone N- (2- (4-Methoxyanilino) -6- {2- [tri (4-methylsulfamoylphenyl) ethylidene] hydrazino 4-pyrimigel ) Hydrazone,

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (11 mg, 45%). Ή-NMR spectrum _{(270 MHz, DMSO- d 6)} δρριη: 9.78 (s, 2H), 8.59 (s, 1H), 8.05 (d, 4H, J = 8.6 Hz), 7.86 (d, 2H, J = 9.2 Hz), 7.81 (d, 4H, J = 8.6 Hz), 7.50-7.45 (m, 2H), 6.86 (d, 2H, J = 9.2 Hz), 6.57 (s, 1H), 3.74 (s, 3H) ), 2.45 (s, 6H, J = 4.6 Hz), 2.38 (s, 6H)

MS (APCI, m / z): 652 (M + D +

HPLC (reversed): Rt. (Min) = 4.09 Example.843

 1- (4-methylsulfamoylphenyl) -triethanone N- (2- (4-methylthioanilino)-6- {2-[(trimethyl-4-sulfamoylphenyl) ethylidene] hydrazino}- 4-Pirimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (7 rag, 32%). MS (APCI, m / z): 668 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.80. Example 844

 1- (4-Methylsulfamoylphenyl)-1-ethanone N- (2- (2-Fluoro-4-methoxyanilino) -6- {2- [tri (4-methylsulfamoylphenyl) ethylidene ] Hyd Radino} -4 -Pyrimidinile) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (22 mg, 74%). Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) 5 ppm: 9.84 (s, 2H), 8.02 (d, 4H, J = 8.5 Hz), 7.94-7.88 (m, 1H), 7.80 (d, 4H, J = 8.5 Hz), 7.76 (s, 1H), 7.45 (brs, 2H), 6.89 (dd, 1H, J = 2.8, 12.6 Hz), 6.76 (dd, 1H, J = 2., 8.4 Hz), 6.60 (s, 1H), 3.78 (s, 3H), 2.45 (s, 6H), 2.35 (s, 6H)

MS (APCI, m / z): 670 (M + l

HPLC (reversed): Rt. (Min) = 4.40. Example 845

 1- (4-Methylsulfamoylphenyl) -1-ethanone N- (2- (4-ethylsulfamoylphenyl)-6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4 -Pyridinidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (29 mg, 56 °). MS (APCI, m / z): 650 (M + lH

HPLC (reversed): Rt. (Min) = 4.61. Example 846

1- (4-methylsulfamoylphenyl) -1-ethanone N-C2- (4-trifluoromethylylanilino) -6- {2- [1- (4- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (51 mg, 75 mg). MS (APCI, m / z): 690 (M + D +

HPLC (reversed): Rt. (Min) = 4.98'Example 847

Tri- (4-pyridyl) -triethanone N- (2- (3-methoxy-4-fluoroalumino) -6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were conducted in the same manner as in Example 547, to obtain the desired product (4 mg, 12%). MS (APCI, m / z): 486 (M + D +

HPLC (reversed): Rt. (Min) = 3.11 Example 848 l- (4-Methanesulfonylphenyl) -triethanone N- (2- (3-Methoxy-1-fluoroanilino)-6- {2- [1- (4-Methanesulfonylphenyl) ethylidene] hydrazino}- 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to give the desired product (32 mg, 67%). MS, (APCI, m / z): 640 (M + D +

 HPLC (reversed): Rt. (Min) = 4.25. Example 849

Tri (4-methylsulfamoylphenyl) -triethanone N- (2- (3-methoxy-141-fluoroalilino) -6_ {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydra Zino} -4-pyrimidinylile) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (11 mg, 23%). -Image R spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 8.38 (brs, 1H), 8.09 (brs, 2

H), 7.83 (d, 4H, J = 8.4 Hz), 7.65-7.55 (m, 5H), 7.47 (brs, 2H), 7.25-7.18 (m, 1H), 6.63 (s, 1H), 3.90 (s, 3H), 2.46 (d, 6H, J = 3.8 Hz), 2.43

(s, 6H)

 MS (APCI, m / z): 670 (M + l) +

 HPLC (reversed): Rt. (Min) = 4.28. Example 850

l- (4-methylsulfamoylphenyl)-1-ethanone N- (2 (4-dimethylaminoanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethyl)

4-Pirimigel) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 665 (M + 1) +

 HPLC (reversed): Rt. (Min) = 4.19. Example 851

(4-Methylsulfamoylfuel) -1-Ethanone N- (2- (2,4-dimethylanily 5216

293 no) -6-{2-[4- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4- 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 650 (M + D +

HPLC (reversed): Rt. (Min) = 4.37 Example 852

Tri (4-methylsulfamoylphenyl) -1-ethanone N- (2- (2-methyl-4-methoxyanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, ffl / z): 666 (M + l) +

HPLC (reversed): Rt. (Min) = 4.06 Example 853

Tri (4-methylsulfamoylphenyl) -1-ethanone N- (2_ (4_n-pentyloxy) -4-pyrimidinylyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 708 (M) +

 HPLC (reversed): Rt. (Min) = 4.65 Example 854

 1- (4-Methylsulfamoylphenyl) -triethanone N- (2- (4-ethoxyethoxylinino) -6- {2- [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino } -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 666 (M + l

HPLC (reversed): Rt. (Min) = 4.18. Example 855

 1- (4-Methylsulfamoylphenyl) -triethanone-(2- (4- (1-Methyl-sulfone pill) anilino) _6-{2- [Tri (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 678 (MH

HPLC (reversed): Rt. (Min) = 4.84 Example 856

 1- (4-methylsulfamoylphenyl) -triethanone N- (2- (4-benzylanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (8 mg, 12%). MS (APCI, m / z): 712 (M + D +

HPLC (reversed): Rt. (Min) = 4.95 Example 857

 1- (4-Methylsulfamoylphenyl) -triethanone N- (2- (4-n-hexyloxyanilino) -6- {2- [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino } -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 722 (M + l) +

HPLC (reversed): Rt. (Min) = 5.23 Example 858

1- (4-'enyl) -toethanone N (2- (2-fluoroanilino) -6- {2- [l- (4-enyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (80 mg, 60 mg). Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) άριη: 9.96 (s, 2H), 8.49 (t, 1H, J = 7.8 Hz), 8.03 (d, 4H, J = 8.8 Hz), 7.82 (d , 4H, J = 8.8 Hz), 7.79 (d, 1H, J = 2.2 Hz), 7.58 (brs, 2H), 7.27-7.15 (m, 2H), 7.09-7.00 (m, 1H), 6.64 (s, 1H), 2.83 (q, 4H, J = 7.3 Hz), 2.37 (s, 6H), 0.98 (t, 6H, J = 7.3 Hz)

 MS (APCI, m / z): 668 (M + D +

 HPLC (reversed): Rt. (Min) = 4.39. Example 859

 1- (4-Ethylsulfamoylphenyl)-1-ethanone N- (2- (3-fluoroallylino) -6- {2- [1- (4-ethylsulfamoylphenyl) ethylidene ] Hydrazino 4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product (69 mg, 52%). Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) ppm: 9.91 (s, 2H), 9.09 (s, 1H), 8.33 (d, lH, J = 14.0 Hz), 8.07 (d, 4H, J = 8.5) Hz), 7.82 (d, 4H, J = 8.5 Hz), 7.60-7.53 On, 3H), 7.26 (q, 1H, J = 7.8 Hz), 6.71 (t, 1H, J = 7.

2 Hz), 6.60 (s, 1H), 2.82 (q, 4H, J-7.3 Hz), 2.39 (s, 6H), 0.98 (t, 6 H, J = 7.3 Hz)

MS (APCI, m / z): 668 (M + l) l

 HPLC (reversed): Rt. (Min) = 4.59. Example 860

4- (2-methanesulfoelfenyl) -1-ethanone N_ (2- (2,3-dimethylanilino) -1-6- {2- [1- (4-methylsulfonylphenyl) ethylidene] hydrazino} -4- Pyrimidi Nirile) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 620 (M + l) +

HPLC (reversed): Rt. (Min) = 4.1U Example 861

 1- (4-methanesulfonylphenyl) -triethanone N- (2- (2-ethylfuranylino) -6- {2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 620 (M + l) +

HPLC (reversed): Rt. (Min) = 4.10 Example 862

 1- (4-Pyridyl) -1 -ethanone N- (2- (2-Methyl-4-methoxyanilino) ■ 6- {2- [1- (4-Pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 482 (M + l) +

HPLC (reversed): Rt. (Min) = 2.75 Example 863

l- (4-pyridyl) -1-ethanone N- (2- (2-ethylanilino) -1-6- (2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product. ,

MS (APCI, m / z): 466 (M + l) +

HPLC (reversed): Rt. (Min) = 2.98 Example 864

1- (4-pyridyl) -triethanone N- (2- (2-methyl-14-chloroanilino) -1- 6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 486 (M + l) +

HPLC (reversed): Rt. (Min) = 3.15. Example 865

 1- (4-pyridyl) -triethanone N- (2- (2-methyl-5-methoxyanilino) -1-6-(2- [1- (4-pyridyl) ethylidene] hydrazino 4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product.

MS (APCI, m / z): 482 (M + l

HPLC (reversed): Rt. (Min) = 2.85 Example 866

1- (4-Methanesulfonylphenyl) -triethanone N_ (2- (2-Methyl-5-methoxyanilino) _6-{2- [1- (4-Mesulfonylphenyl) ethylidene] hydrazino}- 4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 636 (M + D +

HPLC (reversed): Rt. (Min) = 3.92 Example 867

Tri (4-methanesulfonylphenyl) -triethanone N- (2- (3-ethoxylanilino) -1-6- [2- [1- (4-methanesulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) Hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 636 (Mil) I

HPLC (reversed): Rt. (Min) = 4.11 Example 868

 1_ (4-pyridyl) -triethanone N- (2- (2-fluoro-4-ethoxyethoxylinilino) -1-6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

Reaction and purification were carried out in the same manner as in Example 547 to obtain the desired product. , MS (APCI, m / z): 500 (M + D + 03 05216

298

HPLC (reversed): Rt. (Min) = 3.12 Example 869

 -(4-Methylsulfamoylphenyl) -1 -ethanone N- (2- (2-Fluoro-4-ethoxyanilino) -6- {2- [2- (4- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 684 (M + D +

HPLC (reversed): Rt. (Min) = 4.20. Example 870

2- (4-methylsulfamoylphenyl) -1-enothanone N- (2- (4-n-propylanilino) -1-6- (2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino } -4-Pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z) 664 (Mil) i

HPLC (reversed): Rt. (Min) = 4.78 Example 871

 1- (4-Methylsulfamoylphenyl) -triethanone N- (2- (3-difluoromethoxycyanilino)-6- {2- [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone

 Reaction and purification were carried out in the same manner as in Example 561 to obtain the desired product.

MS (APCI, m / z): 688 (M + D +

HPLC (reversed): Rt. (Min) = 4.50 Example 872

Reference Example 61 2-Phenylamino-1,4,6-dihydrazinopyrimidine (23 mg, 0.1 reference volume) synthesized in 1 was mixed with ethanol (1 ml) and 4-acetylpyridine (0.017 ml, (0.15 mmol), and the mixture was heated under reflux for 15 hours. To the reaction system was further added 4-acetyl-N-methyl-benzenesulfonamide (32 mg, 0.15 methylol) synthesized in Reference Example 298, and the mixture was heated under reflux for 15 hours. When the crude reaction system was analyzed by LCMS, a peak containing MS (APCI, m / z) 530 was detected. Reference example 1

 N- (2,6-Dicyclopyrimidine-4-yl) _ (2-methoxypheninole) amine

2,4,6_Triclomouth pyrimidine (9.9 g, 54 mmol) was dissolved in acetone-water (3: 2, v / v, 150 ml), and 2-methoxyaniline (108 t ol) was added. Was heated to reflux for 18 hours. After the reaction solution was cooled to room temperature, the precipitated crystals were collected by filtration. This solid was washed with water, ethanol, and an ether solvent, and the obtained solid was further purified by recrystallization. The (ethanol-ether) solid was dried under reduced pressure to obtain the desired product (12.2 g, 84%). , Ϊ́-ΝΜΙ spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 9.74 (s, 1H), 7.60 (brs, 1H), 7.01-7.23 (m, 2H), 6.99 (dt, 1H, J = 1.3 Hz , 7.4 Hz), 6.72 (brs, 1H) 3.8 3 (s, 3H) ''

 HPLC (revesed): Rt. (Min) = 5.29

 MS (APCI, m / z): 270 (M + l) +. Reference example 2

 N- (2,6-dihydrazinopyrimidine-4-yl)-(2-methoxyphenyl) amine

 Hydrazine monohydrate (2 ml) was added to N- (2,6-dichloropyrimidine-4-irile)-(2-methoxyphenyl) amine (270 mg, 1 mol) produced in Reference Example 1. At 90 ° C

Stir for 1 hour. The reaction system was cooled to room temperature, water was added to the reaction solution, and the precipitated solid was collected by filtration. The obtained solid was washed with water and ethyl acetate, and dried under reduced pressure to obtain the desired product (138 mg, 53%).

'Η- 丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 7.96 (dd, 1H, J = 1.7 Hz, 7.6 Hz), 7.52 (s, 1H), 7.38 (s, 1H), 7.21 (s , 1H), 6.87-7.03 (m, 4H), 5.57 (s, 1H), 4.05 (brs, 3H), 3.82 (s, 3H) 6

300

HPLC (revesed): Rt. (Min) = 2.51

MS (APCI, m / z): 262 (M + l) +. Reference Example 3 'N- (2,6-dichloropyrimidine-4-yl) -phenylamine

 Dissolve 2,4,6-trichloropyrimidine (9.9 g, 54 mol) in acetone-water (3: 2, v / v, 150 ml), add 2-methoxyaniline (108 mmol), and react Was heated to reflux for 18 hours. After the reaction solution was cooled to room temperature, the precipitated crystals were collected by filtration. This solid was washed with water, ethanol, and a ether solvent, and the obtained solid was further purified by recrystallization. The (ether-ethanol) solid was dried under reduced pressure to obtain the desired product.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 10.30 (s, 1H), 7.54 (d, 2H, J =

(6.8 Hz), 7.40 (t, 2H, J = 7.6 Hz), 7.15 (t, 1H, J = 7.8), 6.76 (s, 1H) HPLC (revesed): Rt. (Min) = 5.06

MS (APCI, m / z): 240 (M + l) +. Reference example 4

 N- (2,6-dihydrazinopyrimidine-4-yl)-(phenyl) amine

 N- (2,6-Dichloropyrimidin-4-yl) -phenylamine (109 liters) prepared in Reference Example 3 was dissolved in ethanol (50 ml), and hydrazine monohydrate (50 ml) was dissolved. And stirred at 90 ° C. for 18 hours. The reaction system was cooled to room temperature, water was added to the reaction solution, and the precipitated solid was collected by filtration. The obtained solid was washed with water and ethyl acetate, and dried under reduced pressure to obtain the desired product (16.5 g, 66%).

-丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 8.70 (s, 1H), 7.62 (d, 2H, J = 7.8 Hz), 7.36 (s, 1H), 7.20 (t, 3H, J = (7.9 Hz), 6.86 (t, 1H, J = 7.3 Hz), 5.53 (s, 1H), 4.10 (brs, 4H) HPLC (revesed): Rt. (Min) = 2.23

MS (APCI, m / z): 232 (M) +. Reference example 5 N- (2,6-dichloropyrimidine-4-yl)-(2-methoxyphenyl) ether

2-Methoxyphenol (0.26 ml, 2.4 mmol) was dissolved in acetone (10 ml), and potassium carbonate (415 mg, 3 mmol) was added. After addition of 2,4,6-trichloropyrimidine (366 mg, 2 mol), the reaction solution was stirred for 20 hours at room temperature. After the solvent was distilled off under reduced pressure, ethyl acetate was added, and the organic layer was washed three times with water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was recrystallized from ethyl acetate to give (2,6-dichloropyrimidine-4-yl)-(2-methoxyphenyl) ether ( 542 mg, 85%) as a solid. To this solid (88 mg, 0.32 ml) was added hydrazine monohydrate (1 ml), and the mixture was stirred at 60 ° C for 3 hours. The reaction system was cooled to room temperature, water was added to the reaction solution, and the precipitated solid was collected by filtration. The obtained solid was washed with water and ethyl acetate, and dried under reduced pressure to obtain the desired product (24 mg, 24%).

HPLC (revesed): Ri. (Min) = 2.32

MS (APCI, m / z): 263 (M + l) +. Reference example 6

 4, 6-dihydrazino-2-cyclopropylpyrimidine

 Phosphorus oxychloride (1 ml) was added to 4,6-dihydroxy-2-cyclopropylpyrimidine, and the mixture was stirred at 100 ° C for 6 hours. After completion of the reaction, the reaction mixture was distilled off under reduced pressure. The residue was dissolved in ethyl acetate and washed with a phosphate buffer (PH 7.0) and water. After concentration, the residue was purified by silica gel column chromatography to obtain 4,6-dioct-2-cyclopropylpyrimidine. To this was added a solution of hydrazine monohydrate-ethanol (4: 1, v / v, 3 ml), and the mixture was stirred at 90 ° C for 1 hour. The reaction system was cooled to room temperature, water was added to the reaction solution, and the precipitated solid was pulverized and collected by filtration. The obtained solid was washed with water and ethyl acetate, and dried under reduced pressure to obtain the desired product (202 mg, 56%).

HPLC (revesed): Rt. (Min) = 2.50

 MS (APCI, m / z): 181. Reference Example 7

2- (2-methoxyphenylamino) -4,6-dihydroxypyrimidine 2-Methoxyphenyldanidine hydrochloride (6.0 g, 30 fractions) was dissolved in ethanol (100 ml), and sodium ethoxide (21 w, 49 ml, 150 mmol) was added. Getyl malonate (18.4 ml, 90 mmol) was added to the reaction system, and the mixture was heated under reflux for 15 hours. After the reaction, the reaction was stopped with acetic acid, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with water. After concentrating the organic layer, ether was added, and the precipitated solid was pulverized, filtered, and washed again with ether to obtain the desired product (4.0 g, 57).

-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρι: 10.82 (brs, 2H), 8.41-8.38 (m, 2H), 7.07-6.89 (m, 3H), 4.83 (s, 1H), 3.88 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.47

MS (APCI, ra / z): 234. Reference Example 8

 2- (2-methoxyphenylamino) -4,6-dichloropyrimidine

 Phosphorus oxychloride (10 ml) was added to 2- (2-methoxyphenylamino) -4,6-dihydroxypyrimidine produced in Reference Example 7, and the mixture was stirred at 100 ° C for 6 hours. After completion of the reaction, the reaction mixture was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with a phosphate buffer (PH 7.0) and water. After concentration, the residue was purified by silica gel column chromatography to obtain the desired product (4.34 g, 94%).

¾-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 10.82 (brs, 2H), 8.41-8.38 (m,

2H), 7.07-6.89 (m, 3H), 4.83 (s, 1H), 3.88 (s, 3H)

 HPLC (revesed): Rt. (Min) = 6.60

 MS (APCI, m / z): 270. Reference Example 9

 2- (2-methoxyphenylamino) -4,6-dihydrazinovirimidine

2- (2-Methoxyphenylamino) -4,6-dichloropyrimidine (4.34 g, 16 ol) prepared in Reference Example 8 was added to hydrazine monohydrate-ethanol (2: 1, v / v, 15 ml). The solution was added and stirred at 90 for 2 hours. Cool the reaction system to room temperature, add water to the reaction solution, and precipitate The obtained solid was filtered and filtered. The obtained solid was washed with water and ethyl acetate, and dried under reduced pressure to obtain the desired product (3.75 g, 89%).

'1!-1 spectrum (270 ¾1, DMS0-d ₆ ) δ ριη: 8.62-8.58 (m, 1H), 7.43 (s, 2H), 7.05 (s, 1H), 6.96-6.93 (m, 1H ), 6.86-6.82 (m, 2H), 5.59 (s, 1H), 4.10 (brs, 4H), 3.85 (s, 3H)

 HPLC (revesed): Rt. (Min) = 2.56

 MS (APCI, m / z): 262. · Reference Example 10

2- (2-methoxy-5-methylphenylamino) -4,6-dihydroxypyrimidine

 2-Methoxy-5-methylaniline hydrochloride (11 g, 80 iimiol) was dissolved in ethanol (60 ml). Cyanamide (6.7 g, 160 ol) was added, and the mixture was heated under reflux for 20 hours. After the solvent was distilled off under reduced pressure, a mixed solvent of ether and ethyl acetate was added, and the precipitated solid (14.4 g) was filtered. A part (6.47 g) of this solid was dissolved in ethanol (150 ml), and sodium ethoxide (21 ml, 49 ml, 150 mmol) was added. To this reaction system was added methyl malonate (18.4 ml, 90 nrniol), and the mixture was heated under reflux for 15 hours. After the reaction, the reaction was stopped with acetic acid and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with water. After concentrating the organic layer, ether was added, and the precipitated solid was pulverized, filtered and washed again with ether to obtain the desired product (5.05 g, 57%).

HPLC (revesed): Rt. (Min) = 2.86

MS (APCI, m / z): 248. Reference Example 11

 2- (2-methoxy-5-methylphenylamino) -4,6-dichloropyrimidine

 The 2- (2-methoxy-5-methylphenylamino) -4,6-dihydroxypyrimidine (5.05 g, 20.4 mmol) produced in Reference Example 10 was reacted and purified in the same manner as in Reference Example 8, and purified. The desired product (5.0 g, 84) was obtained.

1H-NMR (270 MHz, DMS0, TMS) d

HPLC (revesed): Rt. (Min) = 7.20 MS (APCI, m / z): 284. Reference Example 12

 2- (2-methoxy-5_methylphenylamino) -4,6-dihydrazinopyrimidine

 The 2- (2-methoxy-5-methylphenylamino) -4,6-dichloropyrimidine (5 g, 17.6 mmol) produced in Reference Example 11 was reacted and purified in the same manner as in Reference Example 9. The desired product (4 g, 83%) was obtained.

NMR spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 8.44 (s, 1H), 7.51 (brs, 2H), 8.10-8.08 (m, 1H), 6.82 (d, 1H, J = 8.4 Hz), 6.62 (d, 1H, J = 8.4 Hz), 5.58 (s, 1H), 3.81 (s, 3H), 2.25 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.85

MS (APCI, m / z): 276. Reference Example 13

2- (2,4-dimethylphenylinamino) -4,6-dihydroxypyrimidine

 2,4-Dimethylaniline hydrochloride (0.618 ml, 5 mmol) was dissolved in ethanol (4 ml), and after adding cyanamide (420 mg, 10 mmol), the mixture was heated under reflux for 18 hours. After evaporating the solvent under reduced pressure, the residue was dissolved in water and the aqueous phase was washed three times with ether. After the aqueous phase was concentrated by distillation under reduced pressure, the residue was azeotropically dehydrated three times with dry ethanol. This was dissolved again in ethanol (20 ml), and sodium ethoxide (21 wt%, 9.3 ml, 25 mmol) was added. Getyl malonate (2.3 ml, 15 mmol) was added to the reaction system, and the mixture was heated under reflux for 15 hours. Then, the reaction was stopped with acetic acid and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with water. After concentrating the organic phase, ether was added to the residue, and the precipitated solid was pulverized, filtered, and washed again with ether to obtain the desired product.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 10.55 (brs, 2H), 8.00 (brs, 1H), 7.52 (d, 1H, J = 7.8 Hz), 6.97-7.03 (m, 2H), 4.76 (s, 1H), 2.25 (s, 3H), 2.17 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.65 MS (APCI, m / z): 232. Reference Example 14

 2- (2,4-dimethylphenylamino) -4,6-dihydrazinopyrimidine

 Phosphorus oxychloride (2 ml) was added to 2- (2,4-dimethylphenylamino) -4,6-dihydroxypyrimidine (1 ol) prepared in Reference Example 13 and stirred at 100 ° C for 6 hours. did. After completion of the reaction, the reaction mixture was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with a phosphate buffer (pH 7.0) and water. After concentration, a residue obtained after purification by silica gel column chromatography 1 was added with a hydrazine monohydrate-ethanol (2: 1, v / V, 3 ml) solution, and the mixture was stirred at 95 ° C for 2 hours. The reaction system was cooled to room temperature, water was added to the reaction solution, and the precipitated solid was filtered and filtered. The obtained solid was washed with water and ethyl acetate and dried under reduced pressure to obtain the desired product.

Awake R spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 7.60 (d, 1H, J = 8.1 Hz), 7.43- 7.50 (m, 3H), 6.88-6.94 (m, 2H), 5.53 (s, 1H), 5.20 (s, 3H), 2.22 (s, 3H), 2.16 (s, 3H)

 HPLC (revesed): Rt. (Min) = 2.69

MS (APCI, m / z): 260. Reference Example 15

2- (2-ethoxyphenylamino) -4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 2-ethoxydiphosphate hydrochloride (5 mmol) in the same manner as in Reference Example 13 for purification.

R spectrum (270 MHz, DMS0-d ₆ ) (5 ppm: 8.39 (d, 1H, J = 8.2 Hz), 6.86-7.03 "(m, 3H), 4.77 (s, 1H), 4.10 (q, 2H, J = 6.9 Hz), 3.28 (brs.3H), 1.39 (t, 3H, J-6.9 Hz)

 HPLC (revesed): Rt. (Min) = 2.82

MS (APCI, m / z): 248. Reference Example 16 2- (2-ethoxypheniramino) _4,6-dihydrazinopyrimidine

The 2- (2-ethoxyphenylamino) -4,6-dihydroxypyrimidine (1 tmol) produced in Reference Example 15 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. Was. NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 8.63 (dd, 1H, J = 2.2 Hz, 7.5 Hz), 7.46 (brs, 2H), 7.06 (s, 1H9, 6.78-6.95 (m , 3H), 5.63 (s, 1H), 4.06 -4.14 On, 6H), 1.39 (t, 3H, J-6.9 Hz)

HPLC (revesed): Rt. (Min) = 2.73

MS (APCI, m / z): 276 ₀ Reference example 17

 2- (2-methylphenylamino) -4,6-dihydroxypyrimidine

 Reaction was carried out in the same manner as in Reference Example 13 from 2-methylaniline hydrochloride (5 t ol) to give the desired product. ,

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ppm: 7.68 (d, 1H, J = 7.8 Hz), 7.03- 7.23 (m, 3H), 4.74 (s, 1H), 2.22 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.27

MS (APCI, m / z): 218. Reference Example 18

 2- (2-methylphenylamino) -4,6-dihydrazinopyrimidine

 The 2- (2-methylphenylamino) -4,6-dihydroxypyrimidine (1 irnnol) produced in Reference Example 17 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. HPLC (revesed): Rt. (Min) = '2.47

MS (APCI, m / z): 246 ₀ Reference example 19

 2- (3,5-dimethoxyphenylamino) -4,6-dihydroxypyrimidine

Reaction from 3,5-dimethoxyaniline hydrochloride (5 mmol) in the same manner as in Reference Example 13. And purified to give the desired product.

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 7.93 (d, 1H, J = 8.7 Hz), 6.60 (s, 1H), 6.44 (dd, 1H, J = 2.6 Hz, 8.7 Hz), 4.54 (brs, 1H), 3.81 (s, 3H), 3.75 (s, 3H)

HPLC (revesed): t. (Min) = 2.40

MS (APCI, m / z): 264. Reference Example 20

 2- (3,5-dimethoxyphenylamino) -4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting with 2- (3,5-dimethoxyphenylamino) -4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 19 in the same manner as in Reference Example 14 and purifying it. .

 MS (APCI, m / z): 292. Reference Example 21

 2- (2-methoxy-5-phenylphenylamino) -4,6-dihydroxypyrimidine ''

The desired product was obtained from 2-methoxy-5-phenylaniline hydrochloride (5 mmol) in the same manner as in Reference Example 13.

-Thigh R spectrum (270 MHz, DMS0-d ₆ ) (5 ppm: 8.55 (brs, 1H), 7.64 (d, 2H, J = 7.1 Hz), 7.42 (t, 2H, J = 7.5 Hz), 7.28-7.32 (m, 2H), 7.10 (d, 1H, J = 8.4 Hz), 4.70 (brs, 1H), 3.90 (s, 3H)

HPLC (revesed): Rt. (Min) = 3.70

MS (APCI, m / z): 310. Reference example

2- (2-methoxy-5-phenyl-phenylamino) -4,6-dihydrazinopyrimidine 2- (2-methoxy-5-phenylphenylamino) -4,6-dihydride prepared in Reference Example 21 The reaction was carried out from roxypyrimidine (1 mmol) in the same manner as in Reference Example 14 and purification was performed to obtain the desired product. „～ ™

 PCT / JP03 / 05216

308

HPLC (revesed): Rt. (Min) = 3.37

MS (APCI, m / z): 338. Reference Example 23

 2- (2-methoxy-5-tert-butylphenylamino) -4,6-dihydroxypyrimidine.

 The desired product was obtained by reacting with 2-methoxy-5-tert-butylaniline hydrochloride (5 mmol) in the same manner as in Reference Example 13 for purification.

iH-NMR spectrum (270 MHz, DMSO-d ₆ ) <5 ppm: 8.27 (s, 1H), 6.92-7.04 (m, 2H), 4.83 (s, 1H), 3.83 (s, 3H), 1.27 (s, 9H)

HPLC (revesed): Rt. (Min) = 3.65

MS (APCI, m / z): 290. Reference Example 24

 2- (2-methoxy-5-tert-butyl-phenylamino) -4,6-dihydrazinopyrimidine 2- (2-methoxy-5-tert-butylphenylamino) -4, prepared in Reference Example 23 The desired product was obtained by reacting and purifying 6-dihydroxypyrimidine (1 bandol) in the same manner as in Reference Example 14.

, ¾-band R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 8.62 (s, 1H), 7.38 (s, 2H), 7.0 3 (s, 1H), 6.83 (s, 2H), 5.56 (s, 1H), 4.11 (s, 4H), 3.82 (s, 3H), 1.27 (s, 9H)

 HPLC (revesed): Rt. (Min) = 3.37

 MS (APCI, m / z): 318. Reference Example 25

 2- (2-fluoromethyl-5-trifluoromethylphenylamino) -4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 2-fluoro-5-trifluoromethyladiline hydrochloride (5 mmol) in the same manner as in Reference Example 13 for purification.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριιι: 8.22 (brs, 1H), 7.36-7.45 (m, 2 H), 4.52 (brs. IH)

 HPLC (revesed): Rt. (Min) = 3.45

 MS (APCI, m / z): 290. Reference Example 26

 2- (2-fluoro-5-trifluoromethylphenylamino) -4,6-dihydrazinopyrimidine

 The 2- (2-fluoro-5-trifluoromethylphenylamino) -4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 25 was reacted and purified in the same manner as in Reference Example 14, and purified. The desired product was obtained.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δριιιι: 8.77 (d, IH, J = 7.1 Hz), 7.88 (brs, IH), 7.28-7.45 (m, 4H), 5.67 (s, IH), 4.12 (brs, 4H)

HPLC (revesed): Rt. (Min) = 2.95

MS (APCI, m / z): 318. Reference Example 27

 2- (2-fluorophenylamino) -4,6-dihydroxypyrimidine

 The desired product (361 mg, 33%) was obtained by reacting with 2_fluoradiphosphoric acid hydrochloride (5 mmol) in the same manner as in Reference Example 13 for purification.

¾-image R spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 8.24 (s, IH), 6.97-7.29 (m, 3H), 4.81 (s, IH)

HPLC (revesed): Rt. (Min) = 2.46

MS (APCI, m / z): 222. Reference Example 28

 2- (2-fluorophenylamino) -4,6-dihydrazinopyrimidine

The desired product was obtained by reacting with 2- (2-7 phenylamino) -4,6-dihydroxypyrimidine (1 thiol) produced in Reference Example 27 by reacting in the same manner as in Reference Example 14. . TJP03 / 05216

310,

'Η-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 8.34 (t, 1H, J = 8.4 Hz), 7.40 (m, 3H), 7.04-7.18 (m, 2H), 6.90-6.95 (m , 1H), 5.61 (s, 1H), 4.09 (brs, 4H)

 HPLC (revesed): Rt. (Min) = 2.31

MS (APCI, m / z): 250. Reference Example 29

 2- (2-Fluoro + methylphenylamino)-4,6-dihydroxypyrimidine

 The desired product was obtained by reacting and purifying 2-fluoro-4-methylaniline hydrochloride (5-bandol) in the same manner as in Reference Example 13.

Ή-NMR spectrum (270 MHz, DMSO-d ₆ ) δ ppm: 8.04 (s, 1H), 6.96-7.11 (m, 2H), 4.82 (s, 1H), 2.29 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.82

MS (APCI, m / z): 236. Reference Example 30

 2- (2-Fluoro mouth-4-methylphenylamino)-4, 6-dihydrazinopyrimidine

 The 2- (2-fluoro-4-methylphenylamino) -4,6-dihydroxypyrimidine (one t-ol) produced in Reference Example 29 was reacted and purified in the same manner as in Reference Example 14, and purified. I got something.

lH-wake R spectrum (270 MHz, DMSO- d ₆ ) δ ppm: 8.10 (t, 1H, J = 8.4 Hz), 7.36 (brs, 3H), 6.96 (d, 1H, J-12.2 Hz), 6.87 ( d, 1H, J = 8.3 Hz), 5.59 (s, 1H), 4.08 (brs, 4H), 2.25 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.61

MS (APCI, m / z): 264. Reference Example 31

 2- (2,6-difluorophenylamino) -4,6-dihydroxypyrimidine

Reaction from 2, 6-difluoroaniline hydrochloride (5 mmol) in the same manner as in Reference Example 13. And purified to give the desired product.

-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 10.67 (brs, 1H), 7.02-7.24 (m, 5H), 4.60 (s, 1H)

HPLC (revesed): Rt. (Min) = 2.30

MS (APCI, m / z): 240. Reference Example 32

 2- (2,6-difluorophenylamino) -4,6-dihydrazinopyrimidine

 The 2- (2,6-difluorophenylamino) -4,6-dihydroxypyrimidine (1 ol) produced in Reference Example 31 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. Was.

¾-丽 R spectrum (270 MHz, DMS0-d ₆ ) d pm: 7.76 (s, 1H), 7.15-7.23 (m, 3H), 7.04 (t, 2H, J = 8.1 Hz), 5.56 (s, 1H ), 3.99 (s, 4H)

HPLC (revesed): Rt. (Min) = 2.06

MS (APCI, m / z): 268. Reference Example 33

 2- (2,3,4-trifluorophenylamino) _4,6-dihydroxypyrimidine

 The desired product was obtained by reaction from 2,3,4-trifluoraniline hydrochloride (5 benzyl) by reaction in the same manner as in Reference Example 13.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) (5 pm: 10.40 (brs, 2H), 7.78 (s, 1H), 7.23-7.33 On, 1H), 4.82 (s, 1H) '

HPLC (revesed): Rt. (Min) = 2.95

MS (APCI, m / z): 258. Reference example 34

 2- (2,3,4-trifluoro-phenylamino) -4,6-dihydrazinopyrimidine

The 2- (2,3,4-trifluoromethylphenylamino) -4,6-dihydroxypyrimidine (one t-ol) produced in Reference Example 33 was reacted and purified in the same manner as in Reference Example 14, and purified. I got

-丽! 1 spectrum (270 ¾1, DMS0-d ₆ ) δ ριη: 7.87-7.94 (m, 2H), 7.11-7.35 (m, 4H), 5.62 (s, 1H)

HPLC (revesed): Rt. (Min) = 2.65

MS (APCI, m / z): 286. Reference Example 35

 2- (2,5-difluoro mouth phenylamino) -4,6-dihydroxypyrimidine

 2,5-Difluoraniline (0.4 ml, 4 liters) was dissolved in ethanol (2 ml), and 1H-pyrazole-tricarpoxyamidine hydrochloride (586 mg, 4 liters) was added to this solution and the solution was added for 15 hours Heated to reflux. After evaporating the solvent under reduced pressure, the residue was dissolved in water and the aqueous phase was washed three times with ether. After concentration of the aqueous phase by distillation under reduced pressure, the residue was azeotropically dehydrated three times with dry ethanol. This was dissolved again in ethanol (20 ml), and sodium ethoxide (21 wt¾, 9.3 ml, 25 删 ol) was added. Getyl malonate (2.3 ml, 15 mL) was added to the reaction system, and the mixture was heated under reflux for 15 hours. The reaction was stopped with acetic acid, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with water. After concentrating the organic phase, ether was added to the residue, and the precipitated solid was pulverized and then collected by filtration and washed again with ether to obtain the desired product (221 rag, 23%).

HPLC (revesed): Rt. (Min) '= 2.35

MS (APCI, m / z): 240. Reference Example 36

 2- (2,5-difluorophenylamino) -4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting 2- (2,5-difluorophenylamino) -4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 35 by reacting in the same manner as in Reference Example 14 to obtain the desired product.

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 8.55-8.45 (m, 1H), 7.52 (brs, 2 H), 7.23-7.15 (m, 1H), 5.69 (s, 1H), 4.19-4.10 (brs, 4H)

HPLC (revesed): Rt. (Min) = 2.53 MS (APCI, m / z): 268. Reference Example 37

 2- (2-fluoro-5-methylphenylamino) -4,6-dihydroxypyrimidine

 The desired product (363 mg, 39%) was obtained by reacting and purifying 2-fluoro-5-methylaniline (4 mmol) in the same manner as in Reference Example 35.

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) dppm: 10.67 (brs, 2H), 8.59 (brs, 1H), 8.11 (d, 1H, J = 8.3 Hz), 7.13 (dd, 1H, J = 8.3) Hz, 11.2 Hz), 6.89 (m, 1H), 4.87 (s, 1H), 2.30 (s, 3H)

HPLC (revesed): Rt. (Min) = 3.04

 MS (APCI, m / z): 236. Reference example 38 '

 2- (2-fluoro-5_methylphenylamino) -4,6-dihydrazinopyrimidine

 The 2- (2-fluoro-5-methylphenylamino) -4,6-dihydroxypyrimidine (1 t-ol) produced in Reference Example 37 was reacted and purified in the same manner as in Reference Example 14, and purified. The desired product (140 mg, 53%) was obtained.

丽 R spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 8.18 (d, 1H, J = 6.1 Hz), 7.38-

7.30 (m, 3H), 7.00 (dd, 1H, J = 8.6 Hz, 11.6 Hz), 6.70 (m, 1H), 5.61 (s, 1H), 4.09 (s, 4H), 2.27 (s, 3H)

 HPLC (revesed): Rt. (Min) = 2.64

 MS (APCI, m / z): 264. Reference example 39

2_ (2-Fluoro-4-phenylamino)-4,6-dihydroxypyrimidine

 The desired product (289 mg, 28%) was obtained by reacting and purifying 2-fluoro-4-chloroaniline (4 marl ol) in the same manner as in Reference Example 35.

Ή-band R spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 11.10-10.40 (brs, 2H), 8.70 (br s, 1H), 8.33 (t, 1H, J = 9.2 Hz), 7.51 (dd, 1H) , 2.7 Hz, 10.8 Hz), 4.90 (s, 1H),

 HPLC (revesed): Rt. (Min) = 3.33

MS (APCI, m / z): 256. Reference example 40

 2- (2-Fluoro-4-chlorophenylamino) -4,6-dihydrazinopyrimidine

 The 2- (2-fluoro-4_chlorophenylamino) _4,6-dihydroxypyrimidine (1 bandol) produced in Reference Example 39 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (47 mg, 17%).

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 8.37 (t, 1H, J = 8.9 Hz), 7.6 (s, 1H), 7.38-7.32 (m, 3H), 7.11 (d, 1H, J = 8.7 Hz), 5.61 (s, 1H), 4.09 (s, 4H)

 HPLC (revesed): Rt. (Min) = 2.78

MS (APCI, m / z): 284. Reference Example 41

 2- (2,3-difluorophenylamino) -4,6-dihydroxypyrimidine

 The desired product (500 mg, 51%) was obtained by reaction from 2,3-difluoroaniline (4 mmol) in the same manner as in Reference Example 35 and purification.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 11.10-10.60 (brs, 2H), 8.80 (s,

1H), 8.06-8.03 (m, 1H), 7.19-7.09 (m, 2H), 4.92 (s, 1H)

HPLC (revesed): Rt. (Min) = 2.96

MS (APCI, m / z): 240. Reference Example 42

 2- (2,3-difluoro-phenylamino)-4,6-dihydrazinopyrimidine

The 2- (2,3-difluorophenylamino) -4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 41 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product, mg, 57 mg. %). ¾ - image R spectrum _{(270 MHz, DMS0-d 6} ) δρρπι: 8.08 (t, 1H, J = 7.3 Hz), 7.80 (s, 1H), 7.39 (s, 2H), 7.04 (dd, 1H, J = 8.4 Hz, 16.7 Hz), 6.95 (dd, 1H, J = 8.4 Hz, 16.7 Hz), 5.63 (s, 1H), 4.09 (s, 4H)

HPLC (revesed): Rt. (Min) = 2.49

MS (APCI, m / z): 268. Reference Example 43

 2- (3,4-difluorophenylamino) -4,6-dihydroxypyrimidine

 Reaction and purification were carried out in the same manner as in Reference Example 35 from 3,4-difluoroaniline (5 mmol) to obtain the desired product (756 mg; 63%).

'H-NMR spectrum _{(270 MHz, DMS0-d 6} ) <5 pm: 10.78 (brs, 2H), 9.08 (brs, 1H), 8.14-8.00 (ni, 1H), 7.35 (q, 1H, J = 6.4 Hz), 7.26 (brs, 1H), 4.99 (s, 1H)

 HPLC (revesed): Rt. (Min) = 2.91

MS (APCI, m / z): 240. Reference example 44

 2- (3,4-difluorophenylamino) -4,6-dihydrazinopyrimidine

 The 1- (3,4-difluorophenylamino) -4,6-dihydroxypyrimidine (1.88 mmol) produced in Reference Example 43 was reacted in the same manner as in Reference Example 14 and purified to give the desired product (320 mg). , 64%).

Ή- 丽 R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 8.77 (s, 1H), 8.22-8.12 (m, 1H), 7.39 (brs, 3H), 7.18 (q, 1H, J = 9.7 Hz) , 5.63 (s, 1H), 4.09 (brs, 4H) HPLC (revesed): Rt. (Min) = 2.58

MS (APCI, m / z): 268. Reference example 45

 2- (2,4-difluorophenylamino) -4,6-dihydroxypyrimidine

The reaction was carried out in the same manner as in Reference Example 35 from 2,4-difluoroaniline (5 mmol) and purified. To give the desired product (525 mg, 44).

ΉNMR spectrum (270 MHz, DMS0-d ₆ ) <5ppm: 10.74 (brs, 2H), 8.57 (brs, 1H), 8.21-8.10 (m, 1H), 7.40-7.28 (m, 1H), 7.13- 7.03 (m, 1H), 4.87 (s, 1H) HPLC (revesed): Rt. (Min) = 2.60

MS (APCI, m / z): 240. Reference Example 46

 2-(2,4-difluoro-phenylamino) -4,6-dihydrazinopyrimidine

 The 2- (2,4-difluoromouth phenylamino) -4,6-dihydroxypyrimidine (1.67 ol) produced in Reference Example 45 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (207 mg). , 46%).

¾-NMR spectrum (270 MHz, DMS0-d ₆ ) ^ ppm: 8.22-8.10 (m, 1H), 7.57 (s, 1H), 7.33 (s, 2H), 7.23-7.13 (m, 1H), 6.99- 6.89 (in, 1H), 5.60 (s, 1H), 4.06 (brs, 4H)

HPLC (revesed): Rt. (Min) = 2.41

MS (APCI, m / z): 268. Reference Example 47

 2- (3-fluorophenylamino) -4,6-dihydroxypyrimidine

 Reaction and purification were performed in the same manner as in Reference Example 35 from 3-fluoroaniline (5 mmol) to obtain the desired product (718 mg, 65%).

'Η-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρηι: 10.76 (brs, 2H), 9.07 (brs, 1H), 7.86 (dd, 1H, J-2.1 Hz, 14.2 Hz), 7.36-7.20 (m , 2H), 6.82 (dt, 1H, J = 2.1 Hz, 8.3 Hz), 4.98 (s, 1H)

HPLC (revesed): Rt. (Min) = 2.74

MS (APCI, m / z): 222. Reference example 48 '

2- (3-fluorophenylamino) -4,6-dihydrazinopyrimidine The 2- (3-fluorophenylamino) -4,6-dihydroxypyrimidine (2.26 mol) produced in Reference Example 47 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (392 mg). , 70%).

-NMR spectrum (270 MHz, DMS0-d ₆ ) 5 pm: 8.76 (s, 1H), 7.92 (dt, 1H, J = 2.2 Hz, 13.0 Hz), 7.45 (dd, 1H, J = 1.1 Hz, 8.3 Hz ), 7.37 (s, 2H), 7.1

5 (q, 1H, J = 7.7 Hz), 6.57 (dt, 1H, J = 2.2 Hz, 8.3 Hz), 5.64 (s, 1H), 4.10 (brs, 4H)

 HPLC (revesed): Rt. (Min) = 2.47

 MS (APCI, m / z): 250. Reference 49

 2- (4-fluorophenylamino) -4,6-dihydroxypyrimidine

 The desired product (760 mg, 69%) was obtained by reacting with 4-fluoroaniline (5 minol) in the same manner as in Reference Example 35 for purification.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρηι: 7.70-7.63 (m, 2H), 7.20-7.10 (m, 2H), 4.87 (s, 1H)

HPLC (revesed): Rt. (Min) = 2.42

MS (APCI, m / z): 222. Reference example 50

 2- (4-fluorophenylamino) -4,6-dihydrazinopyrimidine

 The 2- (4-fluorophenylamino) -4,6'-dihydroxypyrimidine (1.81 benzyl) produced in Reference Example 49 was reacted and purified in the same manner as in Reference Example 14 to give the desired product. (208 mg, 46%).

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 8.55 (s, 1H), 7.85-7.77 (m, 2H), 7.29 (s, 2H), 7.03-6.92 (m, 2H), 5.59 ( s, 1H), 4.08 (brs, 4H)

HPLC (revesed): Rt. (Min) = 2.34

MS (APCI, m / z): 250. Reference Example 51

 2- (2-fluoro-5-chlorophenylamino)-4,6-dihydroxypyrimidine

 The desired product (343 mg, 27%) was obtained by reacting and purifying 2-fluoro-5-chloroaniline (5-bandol) in the same manner as in Reference Example 35. .

-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 8.81 (brs, 1H), 8.53 (dd, 1H, J = 2.6 Hz, 7.2 Hz), 7.33 (dd, 1H, J = 8.8 Hz, 11.1 Hz) ), 7.16-7.10 (m, 1H), 4.94 (s, 1H)

HPLC (revesed): Rt. (Min) = 3.17

MS (APCI, m / z): 256. Reference Example 52

 2- (2-fluoro-5-chlorophenylamino) -4,6-dihydrazinopyrimidine, prepared in Reference Example 51, 2- (2-fluoro-5-chlorophenylamino) -4,6-dihydroxy The compound was reacted and purified from pyrimidine (0.98 tmol) in the same manner as in Reference Example 14 to obtain the desired product (195 mg, 70%).

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρηι: 8.53-8.47 (m, 1H), 7.60 (s, 1H), 7.47 (s, 2H), 7.19 (dd, 1H, J = 8.7 Hz, 11.1 Hz), 6.96-6.89 (m, 1H), 5.67 (s, 1H), 4.11 (s, 4H)

HPLC (revesed): Rt. (Min) = 2.87

MS (APCI, m / z): 284. Reference Example 53

 2- (2, 4, 5-trifluorophenylamino)-4, 6-dihydroxypyrimidine

 Reaction and purification were conducted in the same manner as in Reference Example 35 from 2,4,5-trifluoraniline (5 mmol) to obtain the desired product (522 mg, 41%).

Ή-丽 R spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 10.87 (brs, 2H), 8.78 (brs, 1H), 8.63-8.50 (m, 1H), 7.72-7.60 (m, 1H), 4.92 ( s, 1H)

HPLC (revesed): Rt. (Min) = 3.03

MS (APCI, m / z): 258. Reference example 54

 2- (2,4,5-trifluorophenylamino) -4,6-dihydrazinopyrimidine

 The 2- (2,4,5-trifluorophenylamino) -4,6-dihydroxypyrimidine (1.56 tmol) produced in Reference Example 53 was reacted and purified in the same manner as in Reference Example 14, and purified. (262 mg, 59%).

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) dppm: 8.63-8.51 (m, 1H), 7.65 (s, 1H), 7.54-7.42 (m, 3H), 5.66 (s, 1H), 4.11 ( s, 4H)

HPLC (revesed): Rt. (Min) = 2.76

MS (APCI, m / z): 286. Reference Example 55

 2- (2-methoxyphenylamino) -4,6-dihydroxy-5-methylpyrimidine

 2-Methoxyphenyldanidine hydrochloride (403 mg, 2 mmol) was dissolved in ethanol (5 ml), and sodium ethoxide (21 wt%, 3.24 ml, 10 mol ol) was added. To this reaction system was added methyl malonic acid getyl ester (1 nil, 6 mmol), and the mixture was heated under reflux for 18 hours. After the reaction, the reaction was stopped with acetic acid, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with water. After concentrating the organic layer, ether was added, and the precipitated solid was pulverized, collected by filtration and washed again with ether to obtain the desired product (287 mg, 58%).

Ή- 丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ρηι: 10.85-10.40 (brs, 2H), 8.49 (d, 1H, J = 8.1 Hz), 8.26 (s, 1H), 7.05-6.88 (m , 3H), 3.87 (s, 3H), 1.69 (s, 3H)

 HPLC (revesed): Rt. (Min) = 2.73

MS (APCI, m / z): 248. Reference Example 56

 2- (2-methoxyphenylamino) -4,6-dihydrazino-5-methylpyrimidine

2- (2-methoxyphenylamino) _4,6-dihydroxy-5- produced in Reference Example 55 The product was purified from methylpyrimidine (a mmol) by reaction in the same manner as in Reference Example 14 to give the desired product (196 mg, 71%).

-! Spectrum (270 MHz, DMS0-d ₆ ) ^ ppm: 8.60 (d, 1H, J = 7.3 Hz), 7.23 (s, 2H), 6.98-6.82 (m, 3H), 4.18 (brs, 4H ), 3.87 (s, 3H), 1.69 (s, 3H) HPLC (revesed): Rt. (Min) = 2.40

 MS (APCI, m / z): 276. '' Reference Example 57

 2- (2-Methoxyphenylamino)-4,6-dihydroxy-5-propylpyrupyrimidine Dissolve 2-methoxyphenylguanidine hydrochloride (403 mg, 2 mmol) in ethanol (5 ml) Then, sodium ethoxide (lwt%, 3.24 ml, 10 mmol) was added. To this reaction system was added propylmalonic acid getyl ester (1.23 ml, 6 mmol), and the mixture was heated under reflux for 18 hours. After the reaction, the reaction was stopped with acetic acid, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with water. After concentrating the organic layer, ether was added, and the precipitated solid was collected in a powder frame, filtered, and washed again with ether to obtain the desired product (291 mg, 53%).

Ή-ΝΜΙ spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 8.50 (d, 1H, J = 7.8 Hz), 7.09-6.88 (m, 3H), 3.87 (s, 3H), 2.19 (t, 1H, J = 6.8 Hz), 1.71 (t, 1H, J = 9.2 Hz), 1.42-1.15 (m, 2H), 0.87-0.80 (m, 3H)

HPLC (revesed): Rt. (Min) = 3.42

MS (APCI, m / z): 276. Reference Example 58

 2- (2-methoxyphenylamino) -4,6-dihydrazino-5-propylpyrimidine

 The 2- (2-methoxyphenylamino) -4,6-dihydroxy-5-propylpyrimidine (1 benzyl) produced in Reference Example 57 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (120 mg, 40%).

'Η-wake R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 8.62-8.59 (m, 1H), 7.36 (s, 2H), 7.03-6.85 (m, 3H), 4.33 (brs, 4H), 3.87 (s, 3H), 2.20 (t, 1H, J = 7.6 Hz), 1.30-1.27 (m, 1H), 0.90-0.85 (m, 3H)

HPLC (revesed): Rt. (Min) = 2.75

MS (APCI, m / z): 304. Reference example 59

 2-phenylamino-4,6-dihydroxypyrimidine

 The reaction product was purified from aniline hydrochloride (14.6 ml, 160 bandol) in the same manner as in Reference Example 13 to obtain the desired product (16 g, 49%).

E - field R spectrum _{(270 MHz, DMS0-d 6} ) δρριη: 10.60 (brs, 2H), 8.85 (brs, 1H), 7.62 (d, 2H, J = 7.8 Hz), 7.34-7.27 (m, 2H) , 7.03 (t, 1H, J = 7.0 Hz), 4.88 (s, 1H)

HPLC (revesed): Rt. (Min) = 2.25

MS (APCI, m / z): 204. Reference Example 60

 2-phenylamino-4,6-dichloropyrimidine

 To the 2-phenylamino-4,6-dihydroxypyrimidine (10.1 g, 50 hall) prepared in Reference Example 59 was added oxychloride phosphorus (15 ml), and the mixture was stirred at 100 ° C for 6 hours. After completion of the reaction, the reaction mixture was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with a phosphate buffer (PH 7.0) and water. After drying over anhydrous sodium sulfate and evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (methylene chloride) to obtain the desired product (10.3 g, 86%). ,

¾-image R spectrum (270 MHz, DMS0-d ₆ ) <5ppm: 10.41 (s, 1H), 7.65 (d, 2H, J = 8.6 Hz), 7.35 (t, 2H, J = 7.6 Hz), 7.18 ( s, 1H), 7.06 (t, 1H, J = 7.3 Hz)

 HPLC (revesed): Rt. (Min) = 5.83

MS (APCI, m / z): 240. Reference Example 61 2-phenylamino-4,6-dihydrazinopyrimidine

 The 2-phenylamino-4,6-dichloropyrimidine (13.2 benzyl) produced in Reference Example 60 was reacted and purified in the same manner as in Reference Example 9 to obtain the desired product (2.32 g, 76%).

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 8.47 (s, 1H), 7.79 (d, 2H, J = 7.8 Hz), 7.27 (s, 2H), 7.15 (2H, J = 7.6 Hz ), 6.79 (t, 1H, J = 5.4 Hz), 5.59 (s, 1H), 4.07 (brs, 4H)

HPLC (revesed): Rt. (Min) = 2.35

MS (APCI, m / z): 232. Reference Example 62

 2- (2-phenylethylamino) -4,6-dihydroxypyrimidine

 The reaction product was purified from 2-phenylethylamine (5 thighol) in the same manner as in Reference Example 35 to obtain the desired product.

¾-Band R spectrum (270 MHz, DMS0-d ₆ ) <5ppm: 10.66 (brs, 2H), 7.34-7.19 (m,

5H), 6.45 (brs, 1H), 4.61 (s, 1H), 2.79 (dd, 2H, J = 6.8 Hz, 12.7 Hz),

2.80 (t, 2H, J-7.3 Hz)

 HPLC (revesed): Rt. (Min) = 2.72

 MS (APCI, m / z): 232. Reference Example 63

 2- (2-Phenylethylamino) -4,6-dihydrazinovirimidine

The 2- (2-phenylethylamino) -4,6-dihydroxypyrimidine (1 i iol) produced in Reference Example 62 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. Was. ¾-Band R spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 7.31-7.18 (m, 5H), 7.05 (brs, 2 H), 5.86 (m, 1H), 5.38 (s, 1H), 3.99 ( brs, 4H), 3.39-3.36 (m, 2H), 2.77

(t, 2H, J = 8.1 Hz)

HPLC (revesed): Rt. (Min) = 2.62

MS (APCI, m / z): 260. Reference Example 64

 2- (cyclohexylamino) -4,6-dihydroxypyrimidine

 The desired product was obtained by reacting and purifying cyclohexylamine (5-dragon) in the same manner as in Reference Example 35.

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) άρριη: 10.70-9.70 (brs, 2H), 6.42-6.40 (m, 1H), 4.58 (s, 1H), 3.60-3.50 (m, 1H) , 1.91-1.37 (m, 4H), 1.32-1.16 (m, 6H)

 HPLC (revesed): Rt. (Min) = 2.51

MS (APCI, m / z): 210. Reference example 65

 2- (cyclohexylamino) -4,6-dihydrazinovirimidine

 The desired product was obtained by reacting with 2- (cyclohexylamino) -4,6-dihydroxypyrimidine (1 bandol ol) produced in Reference Example 64 by reacting in the same manner as in Reference Example 14.

Ή- 丽 R spectrum (270 MHz, DMS0-d ₆ ) άρρπι: 6.99 (brs, 2H), 5.57 (d, 1H, J

= 8.4 Hz), 5.35 (s, 1H), 3.96 (brs, 4H), 3.65-3.62 (m, 1H), 1.82-1.53

(m, 4H), 1.26-1.06 (m, 6H)

 HPLC (revesed): Rt. (Min) = 2.49

MS (APCI, m / z): 238. Reference Example 66

₂ Ichipipe Rijino - _4, 6 - dihydroxypyrimidine

 The target product was obtained by reaction and purification from piperidine (5 tmol) in the same manner as in Reference Example 35.

匪 -band R spectrum (270 MHz, DMS0-d ₆ ) άρριη: 10.54 (brs, 2H), 4.68 (s, 1H9, 3.58-3.56 (m, 4H), 1.57-1.48 (m, 6H)

HPLC (revesed): Rt. (Min) = 2.00

MS (APCI, m / z): 196. Reference Example 67

 2-piridino-4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting the 2-piperidino-4,6-dihydroxypyrimidine (1 mmo 1) produced in Reference Example 66 by reacting in the same manner as in Reference Example 14, and purifying it.

^ -NMR spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 7.05 (s, 2H), 5.36 (s, 1H), 3.97 (brs, 4H), 3.59 (t, 4H, J = 5.4 Hz), 1.56 -1.54 (m, 2H), 1.43-1.41 (m, 4H)

 HPLC (revesed): Rt. (Min) = 1.96

MS (APCI, m / z): 224. Participants 68

 2-piperidino-4,6-dihydroxypyrimidine

 The product was reacted with pyrrolidine (5 mmol) in the same manner as in Reference Example 35 and purified to obtain the desired product.

'Η-wake R spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 4.58 (s, 1Η), 3.38 (m, 4H), 1.8 6-1.82 (m, 4H)

 HPLC (revesed): Rt. (Min) = 1.08

MS (APCI, m / z): 182. Reference Example 69

 2-pyridino-4,6-dihydrazinopyrimidine

 The 2-pyrrolidino-4,6-dihydroxypyrimidine (1 mmo 1) produced in Reference Example 68 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product.

-Band R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 7.05 (s, 2H), 5.39 (s, 1H), 3.3 9-3.34 (m, 4H), 1.84-1.79 (m, 4H)

HPLC (revesed): Rt. (Min) = 1.53

MS (APCI, m / z): 210. Reference example 70

 2- (4-methylphenylamino) -4,6-dihydroxypyrimidine

 Reaction and purification were carried out in the same manner as in Reference Example 35 from 4-methylaniline (four fold) to obtain the desired product (363 mg, 39 »).

-NMR spectrum (270 MHz, DMS0-d ₆ ) 6ppm: 8.68 (brs, 1H), 7.48 (d, 2H, J = 8.4 Hz), 7.12 (d, 2H, J = 8.4 Hz), 4.84 (s, 1H) ), 2.26 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.80

MS (APCI, m / z): 218. Reference Example 71

 2- (4-methylphenylamino) -4,6-dihydrazinopyrimidine

The desired product was obtained by reacting 2- (4-methylphenylamino) -4,6-dihydroxypyrimidine (1 tmol) produced in Reference Example 70 by reacting in the same manner as in Reference Example 14. Was. '11 - 1 scan Bae spectrum _{(270 ¾1112, DMS0-d 6} ) 5ppm: 8.36 (s, 1H), 7.67 (d, 2H, J = 8.4 Hz), 7. 4 (s, 2H), 6.96 (d, 2H, J = 8.4 Hz), 5.56 (s, 1H), 4.07 (s, 4H), 2.21 (s. 3H)

HPLC (revesed): Rt. (Min) = 2.60

MS (APCI, m / z): 246. Reference Example 72

 2- (N-phenyl-N-methylamino) -4,6-dihydroxypyrimidine

 The desired product (350 mg, 49%) was obtained by reacting with N-phenyl-N-methyldanidine hydrochloride (610 mg, 3.3 orchid ol) in the same manner as in Reference Example 7 for purification. ,

HPLC (revesed): Rt. (Min) = 2.34

MS (APCI, m / z): 218. Reference Example 73

 2- (N-phenyl-N-methylamino) -4,6-dihydrazinopyrimidine

2- (N-phenyl-N-methylamino) -4,6-dihydroxypyri produced in Reference Example 72 Reaction and purification were carried out in the same manner as in Reference Example 14 from midine (1.14 mmol) to obtain the desired compound (0.

16 g, 40%).

 HPLC (revesed): Rt. (Min) = 2.35

 MS (APCI, m / z): 246. Reference example 74

 2- (2-methoxyphenylamino) -4,6-dihydroxy-5-benzylpyrimidine

 The reaction product was purified from 2-methoxyphenyldanidine hydrochloride (400 mg, 2 mmol) and benzylmalonic acid diethyl ester (1.39 ml, 6 mmol) in the same manner as in Reference Example 55, and purified to obtain the desired product (0.46 g, 71%). ).

HPLC (revesed): Rt. (Min) = 3.77

MS (APCI, m / z): 324. Reference Example 75

2- (2-methoxyphenylamino) -4,6-dihydrazino-5-benzylpyrimidine

 The 2_ (2-methoxyphenylamino) -4,6-dihydroxy-5-benzylpyrimidine (0.24 g, 0.67 mol) produced in Reference Example 74 was reacted and purified in the same manner as in Reference Example 14, and purified. (0.2 g, 39%).

¾ -Awake R spectrum (270 MHz, DMS0-d ₆ ) (5 pm: 8.62 (dd, 1H, J = 1.4 Hz, 7.6 Hz), 7.33 (s, 2H), 7.27-7.11 (m, 7H), 6.99-6.84 (m, 3H), 4.18 (s, 4H), 3.87 (s, 3H), 3.68 (s, 2H)

HPLC (revesed): Rt. (Min) = 3.30

MS (APCI, m / z): 352. Reference Example 76

 2- (2-methoxyphenylamino) -4,6-dihydroxy-5-ethylpyrimidine

The product was purified from 2-methoxyphenyldanidine hydrochloride (400 mg, 2 mmol) by reacting with ethyl ethyl malonate (1.14 ml, 6 Miol) in the same manner as in Reference Example 55 to obtain the desired product (0.34 g, 65). I got HPLC (revesed): Rt. (Min) = 3.20

MS (APCI, m / z): 262. Reference Example 77

2- (2-methoxyphenylamino) -4,6-dihydrazino-5-ethylpyrimidine

 The 2- (2-methoxyphenylamino) -4,6-dihydroxy-5-ethylpyrimidine (0.36 g, 1.21 mmol) produced in Reference Example 76 was reacted and purified in the same manner as in Reference Example 14, and purified. (0.23 g, 61%).

HPLC (revesed): Rt. (Min) = 2.49

MS (APCI, m / z): 290. Reference 78

 2- (indrin-1-yl) -4,6-dihydroxypyrimidine

 The obtained product was reacted and purified from indoline (8.5 wol) in the same manner as in Reference Example 35 to obtain the desired product (a. 54 g, 79%).

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 8.44 (d, 1H, J = 8.1 Hz), 7.16 (brs, 2H), 6.90 (brs, 1H), 5.09 (s, 1H), 4.12 (t, 2H, J = 8.6 Hz), 3.16 (t, 2H, J = 8.6 Hz)

HPLC (revesed): Rt. (Min) = 2.97

MS (APCI, m / z): 230. Reference Example 79

 2- (Indolin_1-yl) -4,6-dihydrazinopyrimidine

 The 2- (indrin-1-yl) -4,6-dihydroxypyrimidine (0.57 dish ol) produced in Reference Example 78 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (75 mg). , 51).

1H-NMR (270 MHz, CD30D, TMS) d 8.28 (d, 1H, J = 8.4 Hz), 7.20-7.12 (m, 2H), 6.87 (t, 1H, J = 7.8 Hz), 5.53 (s, 1H ), 4.17 (t, 2H, J = 8.7 Hz), 3.13 (t, 2H, J-8.7 Hz) HPLC (revesed): Rt. (Min) = 2.46

MS (APCI, m / z): 258. Reference Example 80

2- (2-methylthiophene: inylamino)-4, 6-dihydroxypyrimidine

 The obtained product was reacted with 2-methylthioaniline (5 mmol) in the same manner as in Reference Example 35 and purified to obtain the desired product (44 mg, 4%).

iH-NMR spectrum (270 MHz, DMSO-d ₆ ) δρριη: 7.84 (d, 1H, J = 7.6 Hz), 7.40 (d, 1H, J = 7.1 Hz), 7.26-7.13 (m, 1H), 4.82 ( s, 1H)

HPLC (revesed): Rt. (Min) = 2.67

MS (APCI, m / z): 250. Reference 81

 2-(2-methylthiophenenylamino) -4,6-dihydrazinopyrimidine

 The 2- (2-methylthiophenenylamino) -4,6-dihydroxypyrimidine (1 tmol) produced in Reference Example 80 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. .

HPLC (revesed): Rt. (Min) = 2.51

MS (APCI, m / z): 278. Reference Example 82

 2- (3-pyridylamino) -4,6-dihydroxypyrimidine

 The obtained product was reacted with 3-aminopyridine (5 mmol) in the same manner as in Reference Example 35 and purified to obtain the desired product (361 mg, 35%).

删 R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 8.91 (s, 1H), 8.22 (d, 1H, J = 8.4 Hz), 8.16 (d, -1H, J = 4.6 Hz), 7.32-7.25 ( m, 1H), 4.87 (s, 1H) HPLC (revesed): Rt. (min) = 0.87

MS (APCI, m / z): 205 _o P Rank 脑 16

329 Reference example 83

 2- (3-pyridyluramino) -4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting 2- (3-pyridylamino) -4,6-dihydroxypyrimidine (1 ol) produced in Reference Example 82 by reacting in the same manner as in Reference Example 14 to obtain the desired product.

HPLC (revesed): Rt. (Min) = 0.95

MS (APCI, m / z): 233. Reference Example 84

 2- (2-chlorophenylamino) -4,6-dihydroxypyrimidine

 The desired product was obtained by reacting and purifying 2-chloroaniline (5 ol) in the same manner as in Reference Example 35.

R spectrum (270 MHz, DMS0-d ₆ ) δ ρηι: 8.24 (d, 1H, J = 7.8 Hz), 7.51 (d, 1H, J = 7.8 Hz), 7.35 (t, 1H, J = 7.8) Hz), 7.14 (t, 1H, J = 7.8 Hz), 4.88 (s, 1H)

HPLC (revesed): Rt. (Min) = 2.68

MS (APCI, m / z): 238. Reference Example 85

 2- (2-phenylamino) -4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting with 1- (2-chlorophenylamino) -4,6-dihydroxypyrimidine (1 ol) prepared in Reference Example 84 by reacting in the same manner as in Reference Example 14. HPLC (revesed): Rt. (Min) = 2.51

MS (APCI, m / z): 266. Reference Example 86 'Tripyridine-4-yl-ethanone oxime hydrochloride

Hydroxylamine hydrochloride (695 mg, 10 t ol) was dissolved in dioxane (20 ml), 4-acetylpyridine (1.1 ml, 10 ol) was added, and the mixture was heated under reflux for 2 hours. After the reaction, the precipitated solid is collected by filtration, washed with ethyl acetate and ether, and dried under reduced pressure. The desired product (1.3 g, 76%) was obtained. Reference Example 87

 2- (2-Fluoro-3_chlorophenylamino) -4,6-dihydroxypyrimidine

 The reaction product was purified from 2-fluoro-3-chloroaniline (2.7 iranol) in the same manner as in Reference Example 35 to obtain the desired product (690 mg, 66%).

HPLC (revesed): Rt. (Min) = 3.23

MS (APCI, m / z): 256 (M + l) +. Reference Example 88

 2- (2_Fluoro-3-chlorophenylamino) 1,4,6-dihydrazinopyrimidine.

 The 2- (2-fluoro-3-chloro-phenylamino) -4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 87 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired compound (187 mg, 66%).

HPLC (revesed): Rt. '(Min) = 2.63

MS (APCI, m / z): 284 (M + l) +. Reference example 89

 2-Methylthio-4,6-dihydrazinopyrimidine

 Hydrazine monohydrate-ethanol solution (2: 1, v / v, 1.5 ml) was added to 2-methylthio-1,4,6-dichloropyrimidine (1 ol) and stirred at 100 ° C for 1 hour. After cooling to room temperature, the precipitated solid was powder-framed and collected by filtration to obtain the desired product (123 mg, 66%).

HPLC (revesed): Rt. (Rain) = 1.05

MS (APCI, m / z): 187 (M + l) +. Reference Example 90 2-phenyl-4,6-dihydroxypyrimidine

 Reaction and purification were carried out from phenylamidine hydrochloride (5 benzyl) in the same manner as in Reference Example 7 to obtain the desired product (808 mg, 86%).

HPLC (revesed): Rt. (Min) = 2.38

MS (APCI, m / z): 189 (M + l) +. Reference Example 91

 2-phenyl-4,6-dihydrazinopyrimidine

 The 2-phenyl-4,6-dihydroxypyrimidine (1 tmol) produced in Reference Example 90 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (100 mg, 46 mg).

 HPLC (revesed): Rt. (Min) = 1.99

MS (APCI, m / z): 217 (M + l) +. Reference Example 92

 2- (pyridine-3-yl) -1,4,6-dihydroxypyrimidine

 It was reacted with nicotinamidine (5 mmol) in the same manner as in Reference Example 7 and purified to obtain the desired product (946 mg, 90%).

HPLC (revesed): Rt. (Min) = 1.56

MS (APCI, m / z): 190. Reference 93

 2-(pyridine-3-yl) —4,6-dihydrazinopyrimidine

 The 2- (pyridine-3-yl) -4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 92 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (29 mg, 13%).

HPLC (revesed): Rt. (Min) = 0.80

MS (APCI, m / z): 218. Reference Example 94

 2- (4-Methyl ^ / phenylmethyl) -1,4,6-dihydroxypyrimidine

 It was reacted and purified from 4-methylphenylmethylamidine (5-bandol) in the same manner as in Reference Example 7 to obtain the desired product (1.08 g, 90%).

HPLC (revesed): Rt. (Min) = 2.84

MS (APCI, m / z): 217. Reference Example 95

 2- (4-Methylphenylmethyl) -4,6-dihydrazinopyrimidine

 The 2- (4-monomethylphenylmethyl) -1,4,6-dihydroxypyrimidine (1 ol) produced in Reference Example 94 was reacted in the same manner as in Reference Example 14 and purified to give the target compound (203 mg). , 83¾).

 HPLC (revesed): Rt. (Min) 2.50

MS (APCI, m / z): 245. Reference Example 96

 (2--1-yl) —4 6-Dihydroxypyrimidine

 The target compound (1.19 g, 43%) was obtained by reacting with 2-carboxyamine (5 mmol) in the same manner as in Reference Example 7 and purifying it.

HPLC (revesed): Rt. (Min) = 3.32

MS (APCI, m / z): 239. Reference Example 97

 2- (Naphthalene-1-2-yl) 1-4,6-Dihydrazinopyrimidine

 The 2-((naphthalene-2-yl) -1,4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 96 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (127 mg, 48¾) I got

HPLC (revesed): Rt. (Min)-2.74

MS (APCI, m / z): 267. Reference 98

 2- (4-Isopropylphenylamino) 1,4,6-dihydroxypyrimidine 4-isopropylaniline (5 mmol) was reacted and purified in the same manner as in Reference Example 35 to purify the desired product (931 mg, 76%). ).

HPLC (revesed): Rt. (Min) = 3.42

MS (APCI, m / z): 246. Reference 99

 2- (4-Isopropylphenylamino) 1-4,6-dihydrazinopyrimidine Reference Example 98 2- (4-Isopropylphenylamino) 1-4,6-dihydroxypyrimidine (3. Ummol) ) And purified in the same manner as in Reference Example 14 to give the desired product (469 mg, 55 mg).

 HPLC (revesed): Rt. (Min) = 3.16

MS (APCI, m / z): 274. Reference example 100

 2- (4-methoxyphenylamino) 1,4,6-dihydroxypyrimidine

 The reaction product was purified from 4-methoxyaniline (5 thigh) in the same manner as in Reference Example 35 to obtain the desired product (350 mg, 30 mg).

HPLC (revesed): Rt. (Min)-2.25

MS (APCI, m / z): 234. Reference Example 101

 2- (4-Methoxyphenylamino) 1,4,6-dihydrazinopyrimidine Referenced from 2- (4-methoxyphenylamino) 1.4,6-dihydroxypyrimidine (1.12 mmol) produced in Reference Example 100. The desired product (103 mg, 35 mg) was obtained by reaction and purification in the same manner as in Example 14.

HPLC (revesed): Rt. (Min) = 2.39 JP03 / 05216

334

MS (APCI, m / z): 262. Reference example 10'2

 2- (4-trifluoromethoxyphenylamino) -1,4,6-dihydroxypyrimidine

 4 The reaction and purification were carried out from 1-trifluoromethoxyaniline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (U.0 g, 70%).

HPLC (revesed): Rt. (Min) = 3.52

MS (APCI, m / z): 288. Reference example 1Q3

 2- (4-trifluoromethoxyphenylamino) -1,4,6-dihydrazinopyrimidine

 The 2- (4-trifluoromethoxyphenylamino) -1,4,6-dihydroxypyrimidine (2.88 mmol) produced in Reference Example 102 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired compound ( 562 mg, 62%).

HPLC (revesed): Rt. (Min) = 3.16

MS (APCI, m / z): 316. Reference Example 104

 2- (4-methylthiophenenylamino) -4,6-dihydroxypyrimidine

 It was reacted with 4-methylthioaniline (5 mmol) in the same manner as in Reference Example 35 and purified to obtain the desired product (821 mg, 66%).

HPLC (revesed): Rt. (Min) = 2.93

MS (APCI, m / z): 250. Reference Example 105

2- (4-Methylthiophenenylamino) -1,4,6-dihydrazinopyrimidine 2- (4-methylthiophenenylamino) -1,4,6-di produced in Reference Example 104 The reaction product was purified from hydroxypyrimidine (2.62 mmol) in the same manner as in Reference Example 14 to obtain the desired product (525 mg, 72%).

HPLC (revesed): Rt. (Min) = 2.76

MS (APCI, m / z): 278. Reference Example 106

 2- (4-Dimethylaminophenylamino) 1,4,6-dihydroxypyrimidine 4-dimethylaminoaniline (5 ramol) was reacted and purified in the same manner as in Reference Example 35 to obtain the desired compound (1.2 g, 98%).

HPLC (revesed): Rt. (Min) = 1.58

MS (APCI, m / z): 247. Reference Example 107

 2- (4-Dimethylaminophenylamino) 1,4,6-dihydrazinopyrimidine 2- (4-Dimethylaminophenylamino) 1,4,6-dihydroxypyrimidine prepared in Reference Example 106 ) And purified by the same method as in Reference Example 14 to obtain the desired product (248 mg, 21%).

HPLC (revesed): Rt. (Min) = 1.65

MS (APCI, m / z): 275. Reference Example 108

 2- (2-fluorophenylamino) -1-5-methyl-4,6-dihydroxypyrimidine

 It was reacted with 2-fluoroaniline (3.17 mmol) in the same manner as in Reference Example 35 and purified to obtain the desired product (285 mg, 38%).

HPLC (revesed): Rt. (Min) = 2.78

MS (APCI, m / z): 236. Reference Example 109 2- (2-fluorophenylamino) mono-5-methyl-4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting with 2- (2-fluorophenylamino) -1,5-methyl-4,6-dihydroxypyrimidine produced in Reference Example 108 in the same manner as in Reference Example 14 for purification.

 HPLC (revesed): Rt. (Min) = 2.27

MS (APCI, m / z): 264. Reference Example 110

 2- (3-bromophenylamino) 1,4,6-dihydroxypyrimidine

 The desired product was obtained by reacting and purifying 3-promoline phosphorus in the same manner as in Reference Example 35.

 HPLC (revesed): Rt. (Min) = 3.17

MS (APCI, m / z): 282. Reference Example 111

 2- (3-bromophenylamino) -1,4,6-dihydrazinopyrimidine

 Reference Example 1 The 2- (3-bromophenylamino) 1-4,6-dihydroxypyrimidine (1 t ol) produced in Reference Example 10 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (247 mg, 80%). '

HPLC (revesed): Rt. (Min) = 2.84

MS (APCI, m / z): 310. Reference Example 112

 2- (4-bromophenylamino) 1,4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 4-promoline phosphorus (4 mmol) in the same manner as in Reference Example 35 for purification.

 HPLC (revesed): Rt. (Min) = 3.15

MS (APCI, m / z): 282. TJP03 / 05216

337

Reference example il3

 2- (4-bromophenylamino) 1,4,6-dihydrazinopyrimidine

 Reference Example 1 The 2- (4-bromophenylamino) -1,4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 12 was reacted and purified in the same manner as Reference Example 14 to obtain the desired product (175 mg). , 56¾).

HPLC (revesed): Rt. (Min) = 2.94

MS (APCI, m / z): 310. Reference example 114

 2- (indane-5-yl-amino) 1-4,6-dihydroxypyrimidine

 The desired product (678 mg, 70%) was obtained by reacting with 5-aminoindan (four ol) in the same manner as in Reference Example 35 for purification.

 HPLC (revesed): Rt. (Min) = 3.14

MS (APCI, m / z): 244. Reference Example 115

 21 (indan-5-yl-amino) —4,6 dihydrazinopyrimidine

 Reference Example 1 The 2- (indan-5-yl-amino) 1-4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 14 was reacted and purified in the same manner as in Reference Example 14, and purified. 138 mg, 51%).

HPLC (revesed): Rt. (Min) = 3.12

MS (APCI, m / z): 272. Reference Example 116

 2- (3,4-dihydro-1H-2,1,5-benzodioxepin 1.7-amino) 1-4,6-dihydroxypyrimidine

The target product (636 mg, 58%) was obtained by reacting 3,4-dihydro-2H-1, 5-benzodioxepin-7-amine (4 mmol) by reacting in the same manner as in Reference Example 35. . HPLC (revesed): Rt. (Min) = 2.67

MS (APCI, m / z): 276. Reference Example 117

 2- (3,4-dihydro-1H-2,1,5-benzodioxepin-1-7-amino) 1,4,6-dihydrazinopyrimidine

 Reference Example 11 2- (3,4-dihydro-2H-1,5-benzodioxepin-17-amino) prepared in 16 was used in the same manner as in Reference Example 14 from 1,4-dihydroxypyrimidine (1 thigh ol). The reaction and purification were performed to obtain the desired product (281 mg, 93%).

HPLC (revesed): Rt. (Min) = 2.68

MS (APCI, m / z): 304. Reference Example 118

 2 Reacting with 1,3- (3,4-dimethylphenylamino) -4,6-dihydroxypyrimidine 3,4-dimethylaniline (4) in the same manner as in Reference Example 35, purification was performed to obtain the desired compound ( 301 mg, 33%). .

HPLC (revesed): Rt. (Min) = 3.05

MS (APCI, m / z): 232. Reference Example 119

 2-(, 4-dimethylphenylamino) 1,4,6-dihydrazinopyrimidine Reference Example 1 2- (3,4-dimethylphenylamino) -4,6-dihydroxypyrimidine (1 mmol) and purified in the same manner as in Reference Example 14 to obtain the desired product (112 mg, 43%).

HPLC (revesed): Rt. (Min) = 3.04

MS (APCI, m / z): 260. Reference Example 120

2- (3-trifluoromethyl-4-methoxyphenylamino) 4,6-dihi TJP03 / 05216

339 Droxypyrimidine

 The desired product (312 mg, 26%) was obtained by reacting with 3-trifluoromethyl-4-methoxyaniline (four ol) by reacting it in the same manner as in Reference Example 35.

HPLC (revesed): Rt. (Min) = 3.38

MS (APCI, m / z): 302. Reference Example 121

 2- (3-trifluoromethyl-4-methoxyphenylamino) -4,6-dihydrazinopyrimidine

 Reference Example 1 The 2- (3-trifluoromethyl-4-methoxyphenylamino) -1,4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 20 was reacted and purified in the same manner as in Reference Example 14, and purified. 160 mg, 49%).

HPLC (revesed): Rt. (Min) = 3.11

MS (APCI, m / z): 330. Reference Example 122

 2- (6-quinolylamino) 1,4,6-dihydroxypyrimidine

 The target compound (526 mg, 52%) was obtained by reacting with 6-aminoquinoline (4-dragon) in the same manner as in Reference Example 35 and purifying it.

HPLC (revesed): Rt. (Min) = 1.92

MS (APCI, m / z): 255. Reference Example 123

 2- (6-quinolinylamino) _4, 6-dihydrazinopyrimidine

 The desired product was obtained by reacting with 2- (6-quinolylamino) -4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 122 by reacting in the same manner as in Reference Example 14.

 HPLC (revesed): Rt. (Min) = 1.60

MS (APCI, m / z): 283. Reference Example 124

 2- (3,4-difluorophenylamino) -1,4,6-dihydroxypyrimidine

 Reaction and purification were carried out in the same manner as in Reference Example 35 from 3,4-difluoroaniline (four ol) to obtain the desired product.

—NMR spectrum (270 MHz, DMS0-d ₆ ) δρριη: 10.75 (brs, 2H), 9.07 (s, 1H), 8.11-8.02 (m, 1H), 7.41-7.21 (m, 2H), 4.99 (s, 1H)

HPLC (revesed): Rt. (Min) = 3.11

MS (APCI, m / z): 240. Reference Example 125

 2- (3,4-difluorophenylamino) -1,4,6-dihydrazinopyrimidine

 The 2- (3,4-difluorophenylamino) -4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 124 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. Was.

'Η-image R spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 8.79 (s, 1H), 8.23-8.13 (m, 1H), 7.41 (brs, 3H), 7.23-7.13 (m, 1H) , 5.63 (s, 1H), 4.11 (brs, 4H)

HPLC (revesed): Rt. (Min) = 2.49

MS (APCI, m / z): 268 ₀ Reference example 126

 2- (3-Trifluoromethyl-1-fluorophenylamino) 1,4-dihydroxypyrimidine

 The desired product was obtained by reacting with 3-trifluoromethyl-4-fluoroaniline (4 mmol) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 3.57

MS (APCI, m / z): 290. Reference Example 127

 2- (3-trifluoromethyl-4-fluorophenylamino) 1,4,6-dihydrazinopyrimidine

 The 2- (3-trifluoromethyl-4-fluorophenylamino) -4,6-dihydroxypyrimidine (1 t-ol) produced in Reference Example 126 was reacted and purified in the same manner as in Reference Example 14, and purified. I got something.

HPLC (revesed): Rt. (Min)-3.05 '

MS (APCI, m / z): 318. Reference Example 128

 2- (3,5-difluorophenylamino) -4,6-dihydroxypyrimidine,

 The desired product was obtained by reaction and purification from 3,5-difluoroaniline (4 ol) in the same manner as in Reference Example 35.

¾_NMR spectrum (270 MHz, DMS0-d ₆ ) ά ρπι: 10.99 (brs, 2H), 9.29 (s, 1H), 7.56-7.47 (m, 2H), 6.83-6.74 (m, 1H), 5.12 (s, 1H)

HPLC (revesed): Rt. (Min) = 3.26

MS (APCI, m / z): 240. Reference Example 129

 2- (3,5-difluorophenylamino) -1,4,6-dihydrazinopyrimidine

 Reference Example 1 The 2- (3,5-difluorophenylamino) -1,4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 28 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. Obtained.

Ή- 丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.01 (s, 1H), 7.59 (d, 2H, J = 11.1 Hz), 7.49 (s, 2H), 6.54 (t, 1H, J -11.1 Hz), 5.67 (s, 1H), 4.16 (brs, 4H) HPLC (revesed): Ri. (Min) = 2.64

MS (APCI, m / z): 268. Reference Example 130

 2- (3-Fluoro-4-methylphenylamino) -4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 3-fluoro-4-methylaniline (four ol) in the same manner as in Reference Example 35 and purifying it.

- ^ scan Bae spectrum _{(270 ¾1, DMS0 - d 6} ) ppm:! 8.93 (s, 1H), 7.80-7.74 (m, 1H),

7.21-7.10 (m, 2H), 4.92 (s, 1H), 2.18 (s, 3H)

HPLC (revesed): Rt. (Min) = 3.19

MS (APCI, m / z): 236. Reference Example 131

 2- (3-Fluoro-4-methylphenylamino) 1,4,6-dihydrazinopyrimidine

 Reference Example 1 The 2- (3-fluoro-4-methylphenylamino) -1,4,6-dihydroxypyrimidine (1 dragonol) produced in 30 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. I got

Ή-丽 R spectrum (270 MHz, DMS0-d ₆ ) 5 pm: 8.63 (s, 1H), 7.85 (d, 1H, J = 13.5 Hz), 7.35 (s, 2H), 7.35-7.32 (m, 1H ), 7.01 (t, 1H, J = 8.6 Hz), 5.61 (s, lH), 4.10 (brs, 4H), 2.12 (s, 3H)

HPLC (revesed): Rt. (Min): 2.72

MS (APCI, m / z): 264. Reference Example 132

 2-(4-phenoxyphenylamino) 1,4,6-dihydroxypyrimidine

4 Reacted with 1-phenoxyaniline (5 mmol) in the same manner as in Reference Example 35, followed by purification to obtain the desired product (1.0 g, 68%). HPLC (revesed): Rt. (Min) = 3.59

MS (APCI, m / z): 296. Reference Example 133

 2- (4-phenoxyphenylamino) 1,4-, 6-dihydrazinopyrimidine Reference example from 2- (4-phenoxyphenylamino) -1,4,6-dihydroxypyrimidine produced in Reference Example 132 Reaction and purification were carried out in the same manner as 14 to obtain the desired product.

 HPLC (revesed): Rt. (Min) = 3.27

MS (APCI, m / z): 324. Reference Example 134

 2-phenylamino-4,6-dihydroxy-5-methylpyrimidine

 The desired product (698 mg, 64%) was obtained by reacting and purifying aniline (thigh ol) in the same manner as in Reference Example 35.

 HPLC (revesed): Rt. (Min) = 2.37

MS (APCI, m / z): 218. Reference Example 135

 2-phenylamino-4,6-dihydrazino 5-methylpyrimidine

 Reference Example 1 The 2-phenylamino-4,6-dihydroxy-5-methylpyrimidine (2.99IM01) prepared in 34 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (441 mg, 60%). I got

 HPLC (revesed): Rt. (Min) = 2.10

MS (APCI, m / z): 246. Reference Example 136

2- (3,4-Dichlorophenylamino) reaction with 1,4,6-dihydroxypyrimidine 3,4-dichloroaniline (5 mmol) in the same manner as in Reference Example 35 Purification gave the desired product (652 mg, 48¾).

HPLC (revesed): Rt. (Min) = 2.67

MS (APCI, m / z): 272. Reference Example 137

 2- (3,4-diclophenylamino) 1,4,6-dihydrazinopyrimidine 2- (3,4-diclophenylamino) 1,4,6-dihydroxypyrimidine (prepared in Reference Example 136) (1 mmol) and purified by reacting in the same manner as in Reference Example 14 to obtain the desired product.

HPLC (revesed): Rt. (Min) = 3.06

MS (APCI, m / z): 300. Reference Example 138

 2- (3-Methoxycarbonylphenylamino) -1,4,6-dihydroxypyrimidine

 Reaction and purification were carried out from methyl 3-aminobenzoate (5-bandol) in the same manner as in Reference Example 35 to obtain the desired product (668 mg, 51%).

HPLC (revesed): Rt. (Min) = 3.28

MS (APCI, m / z): 262. Reference Example 139

 2- (3-hydrazinocarbonylphenylamino) 1,4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting with 2- (3-methoxycarbonylphenylamino) -4,6-dihydroxypyrimidine (1 bandol ol) produced in Reference Example 138 in the same manner as in Reference Example 14 for purification. .

 HPLC (revesed): Rt. (Min) = 1.20.

MS (APCI, m / z): 290. Reference Example 140

 2- (3-biphenylamino) -1,4,6-dihydroxypyrimidine

 The reaction product was purified from 3-aminobiphenyl (5 mraol) in the same manner as in Reference Example 35 to give the desired product (784 mg, 56%).

HPLC (revesed): Rt. (Min) = 3.72

MS (APCI, m / z): 280. Reference 141

 2- (3-piphenylamino) 1,4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting the 2- (3-biphenylamino) 1-4,6-dihydroxypyrimidine (1 tmol) produced in Reference Example 140 by reacting in the same manner as in Reference Example 14 to obtain the desired product.

 HPLC (revesed): Rt. (Min) = 3.24

MS (APCI, m / z): 308. Reference example 142

 2- (3-chlorophenylamino) -4,6-dihydroxypyrimidine

 The obtained product was reacted with 3-chloroaniline (5 mmol) in the same manner as in Reference Example 35 and purified to obtain the desired product (579 mg, 49 mg).

'Η-Band R spectrum (270 MHz, DMS0-d ₆ ) δ ppm: 10.80 (brs, 2H), 9.09 (s, 1H), 7.94 (t, 1H, J = 2.4 Hz), 7. 8-7.45 ( m, 1H), 7.31 (t, 1H, J = 8.1 Hz), 7.061-7.03 (m, 1H), 4.98 (s, 1H)

HPLC (revesed): Rt. (Min) = 3.20

MS (APCI, m / z): 238. Reference Example 143

 2 1 (3-phenylamino) 1 4; 6-dihydrazino pyrimidine

The 2- (3-chlorophenylamino) -4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 142 was reacted in the same manner as in Reference Example 14 and purified. 16

346 The desired product was obtained.

'Η-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 8.76 (s, 1H), 7.97-7.96 (m, 1H), 7.74 (dd, 1H, 1.1, 8.4 Hz), 7.37 (brs, 2H ), 7.16 (t, 1H, J = 8.4 Hz), 6.83-6.79 (m, 1H), 5.64 (s, 1H)

HPLC (revesed): Rt. (Min) = 2.75

MS (APCI, m / z): 266. Reference Example 144

 2- (3-Methylphenylamino) _4,6-dihydroxypyrimidine

 The desired product (583 mg, 54%) was obtained from 3-methylaniline (5 mmol) by reacting and purifying in the same manner as in Reference Example 35.

HPLC (revesed): Rt. (Min) = 2.81

MS (APCI, m / z): 218. Reference Example 145

 2- (3-methylphenylamino) -1,4,6-Reference Example 14 from 2- (3-methylphenylamino) -1,4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 144 Reaction and purification were carried out in the same manner as in the above to give the desired product.

HPLC (revesed): Rt. (Min) 2.62

 MS (APCI, m / z): 246. Reference Example 146

 2- (3-Methoxy-phenylamino) 1,4,6-dihydroxypyrimidine

 Reaction and purification were carried out from 3-methoxyaniline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (543 mg, 47%).

Marauder R spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 8.78 (s, 1H), 7.34 (t, 1H, J = 2.4 Hz), 7.21 (t, 1H, J = 8.1 Hz), 7.11-7.07 ( m, 1H), 6.63-6.59 (m, 1H), 4.89 (s, 1H), 3.75 (s, 3H) P Employee 216

347

HPLC (revesed): Rt. (Min) = 2.66

MS (APCI, m / z): 234. Reference Example 147

 2- (3-Methoxy-phenylamino) 1,4-, 6-dihydrazinopyrimidine Referenced from 2- (3-methoxy-phenylamino) -1,4,6-dihydrazinopyrimidine (1 mmol) produced in Reference Example 146 Reaction and purification were carried out in the same manner as in Example 14 to obtain the desired product.

[H - NMR spectrum _{(270 MHz, DMS0-d 6} ) (5ppm: 8.48 (s, 1H), 7.65 (t, 1H, J = 2.4 Hz), 7.30 (s, 2H), 7.24 (d, 1H, J = 8.1 Hz), 7.03 (t, 1H, J = 8.1 Hz), 6.36 (dd, 1H, J = 2.4, 8.1 Hz), 5.59 (s, 1H), 4.10 (brs, 4H), 3.71 (s, 3H)

 HPLC (revesed): Rt. (Min) = 2.40

MS (APCI, m / z): 262. Reference Example 148

 2- (3-trifluoromethylphenylamino) -4,6-dihydroxypyrim

It was reacted and purified from 3-trifluoromethylaniline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (583 mg, 54%).

HPLC (revesed): Rt. (Min) = 3.52

MS (APCI, m / z): 272. Reference Example 149

2- (3-Trifluoromethylphenylamino) 4,6-dihydrazinopyrimid 2- (3-trifluoromethylphenylamino) -4,6-dihydroxypyrimidine prepared in Reference Example 148 (1 mmol) was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. 0305216

348

HPLC (revesed): Rt. (Min) = 3.00

MS (APCI, m / z): 300. Reference Example 150

 2- (3-t-butylphenylamino) 1,4,6-dihydroxypyrimidine

 The reaction product was purified from 3-t-butylylaniline (5 ol) in the same manner as in Reference Example 35 to obtain the desired product (804 mg, 62).

HPLC (revesed): Rt. (Min) = 3.67

MS (APCI, m / z): 260. Reference example 151 '

2- (3-t-butylphenylamino) 1,4,6-dihydrazinopyrimidine Reference example 1 2- (3-t-butylphenylamino) -4,6-dihydroxypyrimidine prepared in 50 (1 mmol) was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product.

HPLC (revesed): Rt. (Min) = 3.24

MS (APCI, m / z): 288. Reference Example 152

 2- (3-trifluoromethoxyphenylamino) -4,6-dihydroxypyrimidine

 Reaction and purification were carried out in the same manner as in Reference Example 35 from 3-trifluoromethoxyaniline (5 benzyl) to obtain the desired product (277 mg, 19%). .

HPLC (revesed): Rt. (Min) = 3.65

MS (APCI, m / z): 288. Reference Example 153

2- (3-trifluoromethoxyphenylamino) 1,4,6-dihydrazinopyrimidine The reaction product was purified from 2- (3-trifluoromethoxyphenylamino) 1-4,6-dihydroxypyrimidine (1 mmol) produced in. 52 in the same manner as in Reference Example 14 to obtain the desired product.

HPLC (revesed): Rt. (Min) = 3.09

MS (APCI, m / z): 316. Reference Example 154

 2-phenylthiomethyl-4,6-dihydroxypyrimidine

 It was reacted with 2-phenylsulfanylacetamidine hydrochloride (5 mmol) in the same manner as in Reference Example 7 and purified to obtain the desired product (966 mg, 82%).

HPLC (revesed): Rt. (Min) = 2.86

MS (APCI, m / z): 235. Reference Example 155

 2-phenylthiomethyl-4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting 2-phenylthiomethyl-4,6-dihydroxypyrimidine (1 bandol) produced in Reference Example 54 in the same manner as in Reference Example 14 and purifying it.

 HPLC (revesed): Rt. (Min) = 2.42

MS (APCI, m / z): 263. Reference Example 156

 2-phenoxymethyl-1,4,6-dihydroxypyrimidine

 Reaction and purification were performed in the same manner as in Reference Example 7 from 2-phenoxyacetamidine hydrochloride (5 mmol) to obtain the desired product (916 mg, 84%).

HPLC (revesed): Rt. (Rain) = 2.86

MS (APCI, m / z): 219. Reference Example 157 2-phenoxymethyl-4,6-dihydrazinopyrimidine

Reference Example 1 2-Phenoxymethyl-4,6-dihydroxypyridine ”(1 ranol) produced in 56 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. _C HPLC (revesed) : Rt. (Min) = 2.35

MS (APCI, m / z): 247 ₀ Reference example 158

 2- (3-ditrophenylamino) 1,4,6-dihydroxypyrimidine

 The desired product (493 mg, 40%) was obtained by reacting with 3-nitroaniline (5 benzyl) in the same manner as in Reference Example 35 for purification.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.36 (s, 1H), 8.58 (t, 1H, J = 2.2 Hz), 8.09 (dd, 1H, J = 2.2, 8.1 Hz), 7.82 (dd, 1H, J = 2.2, 8.1 Hz), 7.57 (s, 1H, J = 8.1 Hz), 5.10 (s, 1H)

HPLC (revesed): Rt. (Min) = 2.89

MS (APCI, m / z): 249. Reference Example 159

 2- (3-nitrophenylamino) 1,4,6-dihydrazinopyrimidine

 Reference Example 1 The desired product was obtained by reacting the 2- (3-diphenylphenylamino) -1,4,6-dihydroxypyrimidine (one t-ol) produced in 58 in the same manner as in Reference Example 14 and purifying it. Was.

¾ -wake R spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 9.15 (s, 1H), 8.81 (t, 1H, J = 2.2 Hz), 8.23 (dd, 1H, J = 2.2, 8.4 Hz), 7.62 (dd, 1H, J = 2.2, 8.4 Hz), 7.46-7.40 (m, 3H), 5.65 (s, 1H), 4.13 (brs, 4H)

HPLC (revesed): Rt. (Min) = 2.48

MS (APCI, m / z): 277. Reference Example 160

2- (3-phenoxyphenylamino) 1,4,6-dihydroxypyrimidine The reaction product was purified from 3-phenoxyaniline (5 faces) in the same manner as in Reference Example 35 to give the desired product (588 ing, 40¾).

HPLC (revesed): Rt. (Min) = 3.69

MS (APCI, m / z): 296. Reference Example 161

 2- (3-phenoxyphenylamino) -4,6-dihydrazinopyrimidine Reference Example 16 2- (3-phenoxyphenylamino) 1,4,6-dihydroxypyrimidine prepared in 60 The target product was obtained by reacting and purifying from 1 bandol) in the same manner as in Reference Example 14.

 HPLC (revesed): Rt. (Min) = 3.22

MS (APCI, m / z): 324. Reference Example 162

 2- (3-Methylthiophenenylamino) 1,4,6-dihydroxypyrimidine

The obtained product was reacted with 3-methylthioaniline (5 mmol) in the same manner as in Reference Example 35 and purified to obtain the desired product (973 mg, 78%).

HPLC (revesed): Rt. (Min) = 2.99

MS (APCI, m / z): 250. Reference example 163 '

 2- (3-methylthiophenenylamino) 1,4,6-dihydrazinopyrimidine Reference Example 16 2- (3-methylthiophenenyl)-4,6, -dihydroxypyrimidine (1 sq.) ol) and purified by reacting in the same manner as in Reference Example 14 to obtain the desired product.

 HPLC (revesed): Rt. (Min) = 2.74

MS (APCI, m / z): 278. Reference Example 164 2- (3-trifluoromethylthio-phenylamino) 1,4,6-dihydroxypyrimidine

 Reaction and purification were performed in the same manner as in Reference Example 35 from 3-trifluoromethylthioaniline (5 mmol) to obtain the desired product (621 mg, 41%).

HPLC (revesed): Rt. (Min) = 3.72

MS (APCI, m / z): 304. Reference Example 165

 2- (3-trifluoromethylthio-phenylamino) 1,4,6-dihydrazino pyrimidine

 Reference Example 1 The 2- (3-trifluoromethylthio-phenylamino) -1,4,6-dihydroxypyrimidine (1 bandol) produced in Reference Example 64 was reacted and purified in the same manner as Reference Example 14 to purify the target compound. Obtained.

HPLC (revesed): Rt. (Min) = 3.20

MS (APCI, m / z): 332; Reference Example 166

 2- (4-n-propylphenylamino) -4,6-dihydroxypyrimidine

Reaction and purification were carried out in the same manner as in Reference Example 35 from 4-n-propylaniline (5-bandol) to obtain the desired product (928 mg, 76%).

 HPLC (revesed): Rt. (Min) = 3.46

 MS (APCI, m / z): 246. , Reference Example 167

 2- (4-n-Propylphenylamino) -4,6-dihydrazinopyrimidine 2- (4-n-propylphenylamino) 1,4,6-dihydroxypyrimidine prepared in Reference Example 1 66 ( 3.27 mmol) and purified according to the same method as in Reference Example 14 to obtain the desired product (894 mg, 100%).

HPLC (revesed): Rt. (Min) = 3.07 MS (APCI, m / z): 274. Reference Example 168

 2- (4-n-octylphenylamino) -4,6-dihydroxypyrimidine 41-n-year-old tylylaniline (5 dragon ol) was reacted in the same manner as in Reference Example 35, purified and purified to obtain the desired product (1.38 g, 88%).

HPLC (revesed): Rt. (Min) = 5.26

MS (APCI, m / z): 316. Reference Example 169

 2- (4-n-year-old tylphenylamino) 1,4,6-dihydrazinopyrimidine 2- (4-n-year-old tylphenylamino) 1,4,6-dihydroxypyrimidine prepared in Reference Example 168 (4.16 bandol) and purified by reaction in the same manner as in Reference Example 14 to obtain the desired product (793 mg, 55%).

HPLC (revesed): Rt. (Min) = 4.25

MS (APCI, m / z): 344. Reference Example 170

 2-(4-sec-Butylphenylamino) 1,4,6-dihydroxypyrimidine 41 See-Butylaniline (5 mniol) Purified by reacting in the same manner as in Reference Example 35 to obtain the desired product (821 mg). , 63%).

HPLC (revesed): Rt. (Min) = 3.73

MS (APCI, m / z): 260. Reference Example 171

2- (4-sec-butylphenylamino) 1,4-, 6-dihydrazinopyrimidine Reference Example 1 2- (4-sec-butylphenylamino) -4,6-dihydroxypyrimidine prepared in 70 3.02 mmol) and purified according to the same method as in Reference Example 14 to obtain the desired product (579 mg, 67%). HPLC (revesed): Rt. (Min) = 3.27

MS (APCI, m / z): 288. Reference Example 172

 2- (4-Ethoxyphenylamino) -1,4-dihydroxypyrimidine

 4 The reaction and purification were carried out from 1-ethoxyaniline (5 tmol) in the same manner as in Reference Example 35 to obtain the desired product (1.01 g, 82 mg).

HPLC (revesed): Rt. (Min) = 2.67

MS (APCI, m / z): 248. Reference Example 173

 2- (4-ethoxyphenylamino) 1,4,6-dihydrazinopyrimidine 2- (4-ethoxyphenylamino) 1,4,6-dihydroxypyrimidine prepared in Reference Example 172 (3.60 thigh 01) ) And purified in the same manner as in Reference Example 14 to obtain the desired product (366 mg, 37%).

HPLC (revesed): Rt. (Min) = 2.56

MS (APCI, m / z): 276 (M + l) +. Reference Example 174

 2- (4-chlorophenylamino) -1,4,6-dihydroxypyrimidine

 4 Reacted and purified from monochloroaniline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (719 mg, 61%).

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 9.00 (s, 1H), 7.68 (dt, 2H, J = 2.6 Hz, 9.1 Hz), 7.35 (dt, 2H, J = 2.6 Hz, 9.1 Hz) ), 4.95 (s, 1H) HPLC (revesed): Rt. (Min) = 3.05

MS (APCI, m / z): 238 (M + l) +. Reference Example 175

2-(4-1-phenylamino) 1, 4, 6-dihydrazinopyrimidine The 2- (4-chlorophenylamino) -1,4,6-dihydroxypyrimidine (2.70 mmol) produced in Reference Example 174 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product (561 mg). , 78¾).

-NMR spectrum (270 MHz, DMS0-d ₆ ) δρριιι: 8.68 (s, 1H), 7.85 (dt, 2H, J = 2.6 Hz, 8.9 Hz), 7.31 (s, 2H), 7.17 (dt, 2H, J = 2.6 Hz, 8.9 Hz), 5.61 (s, 1H), 4.09 (s, 4H)

 HPLC (revesed): Rt. (Min) = 2.70

 MS (APCI, m / z): 266 (M + l) +. Reference Example 176

 2- (4-n-hexyloxyphenylamino) 1,4,6-dihydroxypyrimidine

 The desired product (805 mg, 53%) was obtained by reacting and purifying 4-n-hexyloxyaniline (5 benzyl) in the same manner as in Reference Example 35.

HPLC (revesed): Rt. (Min) = 4.19

MS (APCI, m / z): 304 (M + l) +. Reference Example 177

 2- (4-n-Hexyloxyphenylamino) 1-4,6-dihydrazinopyrimi 2- (4-n-Hexyloxyphenylamino) -4 prepared in Reference Example 176 The target product (640 mg, 84%) was obtained by reacting and purifying from 6,6-dihydroxypyrimidine (2.31 mmol) in the same manner as in Reference Example 14.

HPLC (revesed): Rt. (Min) = 3.71

MS (APCI, m / z): 332 (M + l) +. Reference Example 178

 2- (4-Benzylphenylamino) 1,4,6-dihydroxypyrimidine

4 In the same manner as in Reference Example 35, the reverse reaction was carried out from n-hexyloxyaniline (5 mmol). Reaction and purification yielded the desired product (1.07 g, 73%).

HPLC (revesed): Rt. (Min) = 3.74

MS (APCI, m / z): 294. Reference Example 179

 2- (4-Benzylphenylamino) 1-4,6-dihydrazinopyrimidine 2- (4-n-hexyloxyphenylamino) -4, prepared in Reference Example 178

The desired product (490 mg, 44%) was obtained by reacting and purifying 6-dihydroxypyrimidine (3.45 mmol) in the same manner as in Reference Example 14.

HPLC (revesed): Rt. (Min) = 3.31

MS (APCI, m / z): 322. Reference Example 180

 2- (3,5-di-t-butylphenylamino) 1-4,6-dihydroxypyrim

The desired product was obtained by reaction from 3,5-di-1-butylaniline (4 orchids ol) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 4.51

MS (APCI, m / z): 316. Reference Example 181

 2- (3,5-di-tert-butylphenylamino) -1,4,6-dihydrazinopyrimid 2- (3,5-di-tert-butylphenylamino) -1,4 prepared in Reference Example 180 The desired product was obtained by reacting and purifying 6-dihydroxypyrimidine (1 mmol) in the same manner as in Reference Example 14.

HPLC (revesed): Rt. (Min) = 4.05

MS (APCI, m / z): 344. Reference Example 182

 2- (3-Methyl-4-isopropylphenylamino) -1,4,6-dihydroxypyrimidine.

 The desired product was obtained by reacting and purifying 3-methyl-4-isopropylaniline (four ol) in the same manner as in Reference Example 35.

HPLC (revesed): Rt. (Min) = 3.68

MS (APCI, m / z): 260. Reference Example 183

2- (3-Methyl-4-isopropylphenylamino) 1,4,6-dihydrazino pyrimidine

 Reference Example 18 The 2- (3-methyl-4-isopropylphenylamino) -14,6-dihydroxypyrimidine (1 benzyl) produced in Reference Example 82 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. I got

HPLC (revesed): Rt. (Min) = 3.47

MS (APCI, m / z) 288. Reference example 184 '

 2- (4-hexylhexylphenylamino) 1,4,6-dihydroxypyrimidine 4-cyclohexylaniline (4 benzyl) was reacted in the same manner as in Reference Example 35 and purified to obtain the desired product. .

HPLC (revesed): Rt. (Min) = 4.18

MS (APCI, m / z): 286. Reference Example 185

2- (4-cyclohexylphenylamino) 1-4,6-dihydrazinopyrimidine 2- (4-cyclohexylphenylamino) -1,4,6-dihydroxypyrimidine prepared in Reference Example 184 (one thigh) The reaction product was purified in the same manner as in Reference Example 14 to obtain the desired product. 05216

358

HPLC (revesed): Rt. (Min) = 3.81

MS (APCI, m / z): 314. Reference Example 186

 2- (3,5-dimethylphenylamino) -1,4,6-dihydroxypyrimidine

The desired product was obtained by reaction with 3,5-dimethylaniline (four ol) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 3.14

MS (APCI, m / z): 232. Reference Example 187

 2- (3,5-Dimethylphenylamino) 1,4,6-dihydrazinopyrimidine 2- (3,5-Dimethylphenylamino) 1,4,6-dihydroxypyrimidine prepared in Reference Example 186 ( The same product as in Reference Example 14 was reacted and purified from 1 ol) to obtain the desired product.

HPLC (revesed): Rt. (Min) = 3.04

MS (APCI, ra / z): 260. Reference Example 188

 2- (3,5-dimethylphenylamino) -1,4,6-dihydroxypyrimidine

The desired product was obtained by reacting and purifying 2-aminofluorene (four ol) in the same manner as in Reference Example 35.

HPLC (revesed): Rt. (Min) = 3.71

MS (APCI, m / z): 292. Reference Example 189

 2- (fluorene-1-2-ylamino) -1,4,6-dihydrazinopyrimidine

Reference Example 1 The 2- (3,5-dimethylphenylamino) -4,6-dihydroxypyrimidine (1 ol) produced in 88 was reacted and purified in the same manner as in Reference Example 14. Then, the desired product was obtained.

 HPLC (revesed): Rt. (Min) = 3.52

 MS (APCI, m / z): 320. Reference Example 190

 2- (3-Chloro-4-trifluoromethylthiophenenylamino) 1,4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 3-chloromethyl-4-trifluoromethylthioaniline (4 mmol) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 4.20

MS (APCI, m / z): 338. Reference Example 191

 2- (3-chloro-4-1-trifluoromethylthiophenenylamino)-4, 6-dihydrazinopyrimidine

 Reference Example 19 Purification by reacting with 2- (3-chloromethyl-4-trifluoromethylthiophenenylamino) -1,4,6-dihydroxypyrimidine (1 mmol) produced in 90 in the same manner as Reference Example 14 Then, the desired product was obtained.

 HPLC (revesed): Rt. (Min) = 3.75

MS (APCI, m / z): 366. Reference Example 192

 2- (4-Isopropoxyphenylamino) 1,4,6-dihydroxypyrimidine 4-isopropoxydiline (5 ol) was reacted and purified in the same manner as in Reference Example 35 to obtain the desired compound (1 .05 g, 80%).

HPLC (revesed): Rt. (Min) = 2.99

MS (APCI, m / z): 262. Reference Example 193 P Employee 216

360

2- (4-Isopropoxyphenylamino) -1,4,6-dihydrazinopyrimidine. 2- (4-Isopropoxyphenylamino) -1,4,6-dihydroxypyrimidine prepared in Reference Example 192 (3.72 mmol) ) And purified in the same manner as in Reference Example 14 to give the desired product (lllmg, 10¾).

HPLC (revesed): Rt. (Min) = 2.93

MS (APCI, m / z): 290. Reference example 194 '

2- (4-ditrophenylamino) -1,4,6-dihydroxypyrimidine

 4 The reaction product was purified from 12throaline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (19 mg, 2%).

HPLC (revesed): Rt. (Min) = 2.93

MS (APCI, m / z) 249. Reference Example 195

 2- (4-nitrophenylamino) -4,6-dihydrazinopyrimidine

 The 2-((412-trophenylenylamino) -1,4,6-dihydroxypyrimidine (0.5 liio 1) produced in Reference Example 194 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired compound (11 mg, 49%).

HPLC (revesed): Rt. (Min) = 2.45

 MS (APCI, m / z): 277. Reference Example 196

 2- (4-ethoxycarbonylphenylamino) 1,4,6-dihydroxypyrimidine

 The reaction product was purified from ethyl 4-aminobenzoate (5 mmol) in the same manner as in Reference Example 35 to give the desired product (204 mg, 15%).

HPLC (revesed): Rt. (Min) = 3.17

MS (APCI, m / z): 276. 03 05216

361

Reference Example 197

2-({2- [u (4-pi; enylamino) 1 4, 6-dihydrazinopyrimidine

 The 2- (4-ethoxycarbonylphenylamino) -14,6-dihydroxypyrimidine (0 · 46 mmo 1) produced in Reference Example 19 was reacted and purified in the same manner as in Reference Example 14, and purified. The desired product (72 mg, 54 mg) was obtained.

HPLC (revesed): Rt. (Min) = 1.08

MS (APCI, m / z): 290. Reference Example 198

 2- (3-Fluoro-4-methoxyphenylamino) -4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 3-fluoro-4-methoxyaniline (4 mmol) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Ri. (Min) = 2.70

MS (APCI, m / z): 252. Reference Example 199

 2 — (3-Fluoro-4-methoxyphenylamino) 1,4,6-dihydrazinopyrimidine

 The 2- (3-fluoro-4-methoxyphenylamino) 14,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 1 98 was reacted and purified in the same manner as in Reference Example 14 to purify the desired product. Obtained. ·

HPLC (revesed): Rt. (Min) = 2.64

MS (APCI, m / z): 280. Reference example 200

2- (2-Methyl-4-fluorophenylamino) 1,4,6-dihydroxypyri 16

362 Gin

 The desired product was obtained by reacting and purifying 2-methyl-4-fluoroaniline (four ol) in the same manner as in Reference Example 35.

'H-NMR spectrum _{(270 MHz, DMS0-d 6} ) 6 pm: 8.09 (s, 1H), 7.67-7.62 (m, 1H),

7.19-7.00 (m, 2H), 4.78 (s, 1H), 2.22 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.55

MS (APCI, m / z): 236. Reference 201

 2- (2-Methyl-4-fluorophenylamino) -1,4,6-dihydrazinopyrimidine

 The 2- (2-methyl-4-fluorophenylamino) -1,4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 200 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. .

HPLC (revesed): Rt. (Min) = 2.52

 MS (APCI, m / z): 264. ', Reference Example 202

 2- (4-ethoxycarbonylmethylphenylamino) -1,4,6-dihydroxypyrimidine

 The desired product (647 mg, 45 °) was obtained by reacting with 4-aminophenylacetate (5 benzyl) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 2.94

MS (APCI, m / z): 290. Reference Example 203

 2- (4-carboxymethylphenylamino) -4,6-dihydrazinopyrimidine

2- (4-ethoxycarbonylmethylphenylamino) produced in Reference Example 202 It was reacted and purified from -4,6-dihydroxypyrimidine (1 acetyl) in the same manner as in Reference Example 14 to obtain the desired product.

HPLC (revesed): Rt. (Min) = 2.05

MS (APCI, m / z): 290. Reference Example 204

 2- (2-Fluoro-4-methoxyphenylamino) -1,4,6-dihydroxypyrimidine

 The reaction product was purified from 2-fluoro-4-methoxyaniline (one thigh) in the same manner as in Reference Example 35 to obtain the desired product (189 mg, 75 mg).

'H-NMR spectrum (270 MHz, D S0-d ₆ ) δ ρηι: 7.81 (t, 1H, J-9.3 Hz), 6.90 (dd, 1H, J = 2.7 Hz, 12.7 Hz), 6.77-6.72 (m , 1H), 4.78 (s, 1H), 3.74 (s, 3H)

 HPLC (revesed): Rt. (Rain) = 2.50

MS (APCI, m / z): 252. Reference Example 205

 2- (2-fluoro-4-methoxyphenylamino) 1,4,6-dihydrazinopyrimidine

 The 2- (2-fluoro-4-methoxyphenylamino) -4,6-dihydroxypyrimidine (0.41 eol) produced in Reference Example 204 was reacted and purified in the same manner as in Reference Example 14, and purified. Product (82 rag, 72%).

¾ -Awake R spectrum (270 MHz, DMS0-d ₆ ) δρρπι: 7.87 (t, 1H, J = 9.3 Hz), 7.38 (s, 1H), 7.23 (s, 2H), 6.80 (dd, 1H, J = 2.7 Hz, 12.7 Hz), 6.69-6.64 (m, 1H), 5.55 (s, 1H), 4.03 (brs, 4H), 3.73 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.42

MS (APCI, m / z): 280. Reference example 206, P Rank 脑 16

364

2- (4-ethylphenylamino) 1,4,6-dihydroxypyrimidine

 The reaction product was purified from 41-ethylphenylaniline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (492 mg, 43%).

HPLC (revesed): Rt. (Min) = 3.08

MS (APCI, m / z): 232. Reference Example 207

 2-(4-Ethylphenylamino) 1-4, 6-dihydrazinopyrimidine

 The 2- (4-ethylphenylamino) 1-4,6-dihydroxypyrimidine (1.08 mmol) produced in Reference Example 206 was reacted in the same manner as in Reference Example 14 and purified. The desired product (191 mg, 68%) was obtained.

HPLC (revesed): Rt. (Min) = 2.82

MS (APCI, m / z): 260. Reference Example 208

 2- (4-trifluoromethylphenylamino) -4,6-dihydroxypyrimidine

 4 The reaction product was purified from 1-trifluoromethylaniline (5 tmol) in the same manner as in Reference Example 35 to obtain the desired product (472 mg, 35%).

HPLC (revesed): Rt. (Min) = 3.51

MS (APCI, m / z): 272. Reference Example 209

 2- (4,1-trifluoromethylphenylamino) 4,6-dihydrazinopyridine

 The 2- (4-trifluoromethylphenylamino) -14,6-dihydroxypyrimidine (0.63 mmol) produced in Reference Example 208 was reacted and purified in the same manner as in Reference Example 14. Thus, the desired product (119 mg, 63%) was obtained.

HPLC (revesed): Rt. (Min) = 2.95 MS (APCI, m / z): 300. Reference Example 210

 2- (4-n-butoxyphenylamino) -4,6-dihydroxypyrimidine

 4 1 n-Butoxyaniline (5 thighs) was reacted and refined in the same manner as in Reference Example 35 to obtain the desired product (841 rag, 61¾).

HPLC (revesed): Rt. (Min) = 3.52

MS (APCI, m / z): 276. Reference Example 211

 2- (4-n-butoxyphenylamino) 1,4,6-dihydrazinopyrimidine Reference Example 2 2- (4-n-butoxyphenylamino) 1,4,6-dihydroxy prepared in Example 10 The compound was reacted with pyrimidine (1.24 mmol) in the same manner as in Reference Example 14 and purified to obtain the desired product (285 mg, 75%).

HPLC (revesed): Rt. (Min) = 3.31

MS (APCI, m / z): 304. Reference example212

 2 — (4-n-pentyloxyphenylamino) 1-4, 6-dihydroxypyrimidine

 41 The reaction product was purified from n-pentyloxyaniline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (619 mg, 43%).

HPLC (revesed): Rt. (Rain) = 3.87

MS (APCI, m / z): 290. Reference Example 213

 2-(4-n-pentyloxyphenylamino) 1-4,6-dihydrazinopyrimidine

Reference Example 2 2- (4-n-pentyloxyphenylamino) prepared in 1 2-4 P Rank 脑 16

366

6-Dihydroxypyrimidine (1.42 virgin ol) was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product.

HPLC (revesed): Rt. (Min) = 3.51

MS (APCI, m / z): 318. Reference Example 214

 2- (4-n-butylphenylamino) -1,4,6-dihydroxypyrimidine

 Reaction and purification were carried out in the same manner as in Reference Example 35 from 4-n-butylylaniline (5 benzyl) to obtain the desired product (854 mg, 66 mg).

HPLC (revesed): Rt. (Min) = 3.81

MS (APCI, m / z): 260. Reference Example 215

 2- (4-n-butylphenylamino) -1,4,6-dihydrazinopyrimidine

 Reference Example 2 The 2- (4-n-butylphenylamino) 14,6-dihydroxypyrimidine (0.21 mmol) produced in 14 was reacted in the same manner as in Reference Example 14 and purified. Thus, the desired product (51 mg, 85%) was obtained.

HPLC (revesed): Rt. (Min) = 3.49

MS (APCI, m / z): 288. Reference Example 216

 2-1 (3,5-dichloro phenylamino) -1, 4, '6-dihydroxypyrimidine

 The desired product was obtained by reaction with 3,5-dichloroaniline (4 mmol) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 3.74

MS (APCI, m / z): 272. Reference Example 217

2- (3,5-dichloro mouth phenylamino) 1-4,6-dihydrazinopyrimidine PC leakage 216

367 Reference Example 2 2- (3,5-Dichroic phenylamino) 1-4,6-dihydroxypyrimidine (1 t-ol) produced in 16 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. I got

HPLC (revesed): Ri. (Min) = 3.24

MS (APCI, m / z): 300. Reference Example 218

 2- (3-chloro-4-fluorophenylamino) -1,4,6-dihydroxypyrimidine

 The desired product was obtained by reacting and purifying 3-chloro-41-fluoroaniline (4-bandol) in the same manner as in Reference Example 35.

'H-NMR spectrum (270 MHz, DMS0-d ₆ ) ^ m: 10.78 (brs, 2H), 8.99, (s, 1H), 8.05 (d, 1H, J = 6.8 Hz), 7.49 (s, 1H) , 7.37-7.31 (m, 1H), 4.99 (s, 1H)

HPLC (revesed): Rt. (Min) = 3.29-MS (APCI, m / z): 256. Reference Example 219

 2- (3-Chloro-4-fluorophenylamino) -4,6-dihydrazinopyrimi 2- (3-chloro-4-fluorophenylamino) -1,4,6-dihydroxy produced in Reference Example 2 18 The desired product was obtained from pyrimidine (one thigh) by reaction in the same manner as in Reference Example 14 and purification.

-丽 R spectrum (270 MHz, DMS0-d ₆ ) <5 pm: 8.78 (s, 1H), 8.14-8.11 (m, 1H), 7.75-7.69 (m, 1H), 7.40 (s, 2H), 7.20 -7.14 (m, 1H), 5.63 (s, 1H), 4.14 (brs, 4H)

 HPLC (revesed): Rt. (Min) = 2.97

MS (APCI, m / z): 284. Reference Example 220

 2- (2,3-dihydro-benzo [1,4] dioxin-6-yl-lamino) 1,4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 2,3-dihydro-benzo [1,4] dioxin-6-yl-amine (4 ol) in the same manner as in Reference Example 35 for purification.

R-spectrum (270 MHz, DMS0-d ₆ ) δρριιι: 8.59 (s, 1H), 7.29 (s, 1H), 6.39 (d, 1H, J = 8.4 Hz), 6.78 (d, 1H, J = 8.4 Hz), 4.83 (s, 1H), 4.24-4.2 0 (m, 4H)

 HPLC (revesed): Rt. (Min) = 2.45

MS (APCI, / z): 262. '' Reference Example 221

 2- (2,3-dihydro-benzo [1,4] dioxin-6-ylamino) 1-4., 6-dihydrazinopyrimidine

2- (2,3-Dihydro-benzo [1,4] dioxin-6-yl-amino) 1-4,6-dihydroxypyrimidine (1 nimol) prepared in Reference Example 220 was dissolved in methylene chloride (2 ml). Nigoshi, Toryechiruamin (0.7 ml), 2, 4 , to give the 1 hour at room temperature under stirring the ₉ solvent after addition of 6-triisopropylbenzene scan Ruhonirukurorido a (700 mg) was evaporated under reduced pressure, after purification by silica gel column chromatography To the residue obtained was added a solution of hydrazine monohydrate-ethanol (4: 1, v / v, 5 ml), and the mixture was stirred for 10 hours (3 hours at TC). The precipitated solid was pulverized and collected by filtration, and the obtained solid was washed with water and ether, and dried under reduced pressure to obtain the desired product (144 mg, 50%).

Ή-View R spectrum (270 MHz, DMS0-d ₆ ) 5ppm: 8.29 (s, 1H), 7.42 (s, 1H), 7.25 (s, 2H), 7.17 (d, 1H, J = 8.6 Hz), 6.63 (d, 1H, J = 8.6 Hz), 5.55 (s, 1H), 4.19-4.14 (m, 4H), 4.06 (brs, 4H)

HPLC (revesed): Rt. (Min) = 2.34

MS (APCI, m / z): 290. Reference Example 222

 2- (2-Methoxy-3-fluorophenylamino) -4,6-dihydroxypyri

The desired product was obtained by reacting with 2-methoxy-3-fluoroaniline (4-dragon ol) in the same manner as in Reference Example 35 and purifying it.

¾-NMR spectrum (270 MHz, DMS0-d ₆ ) 5 pm: 8.58 (s, IH), 8.33-8.26 (m, IH), 7.12-7.03 (m, IH), 6.98-6.90 (m, IH), 4.89 (s, 1H), 3.88 (s, 3H)

HPLC (revesed): Rt. (Min) = 3.08

MS (APCI, m / z): 252. Reference example m

 2- (2-methoxy-1-3-fluorophenylamino) 1,4,6-dihydrazinopyrimidine

 The reaction was carried out in the same manner as in Reference Example 14 and purified from 2- (2-methoxy-13-fluorophenylamino) -4,6-dihydroxypyrimidine (1 t-ol) produced in Reference Example 2'22. I got something.

NMR-NMR spectrum (270 MHz, DMS0-d ₆ ) (5 pm: 8.43 (d, 1H, J = 8.4 Hz), 8.02 (brs, 2H), 7.86 (brs, IH), 6.99 (dd, IH, J = 8.4, 14.3 Hz), 6.80 (t, IH, J = 8.4 Hz), 5.61 (s, IH), 4.88 (brs, 4H), 3.89 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.80

MS (APCI, m / z): 280. Reference example VIA

 2- (Benzo [1,3] dioxol-5-ylamino) -1,4,6-dihydroxypyrimidine Purified by reacting with benzo [1,3] dioxol-5-ylamine (4 ol) in the same manner as in Reference Example 35. Then, the desired product was obtained.

Ή-wake R spectrum (270 MHz, DMS0-d ₆ ) <5ppm: 8.66 (s, IH), 7.44 (s, IH), 6.8 6 (d, IH, J = 8.4 Hz), 6.82 (d, IH, J = 8.4 Hz), 6.00 (s, 2H), 5.12 (s, IH) HPLC (revesed): Rt. (Min) = 2.35

MS (APCI, m / z): 248. Reference Example 225,2- (2- (benzo [1,3] dioxolyl-5-yl-phenylamino) -4,6-dihydrazinopyrimidine

 The 2- (benzo [1,3] dioxol-5-yl-amino) -1,4,6-dihydroxypyrimidine (one thigh) produced in Reference Example 224 was reacted and purified in the same manner as in Reference Example 221. The target was obtained.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 8.40 (s, 1H), 7.65 (s, 1H), 7.29 (s, 2H), 7.10 (d, 1H, J = 8. Hz) , 6.71 (d, 1H, J = 8.4 Hz), 5.90 (s, 2H), 5.57 (s, 1H), 4.06 (brs, 4H)

HPLC (revesed): Rt. (Min) = 2.26

MS (APCI, m / z): 276. Reference Example 226

 3-amino-N-hexyl-N-methyl-benzamide

 N-Methyl-hexylamine (20 mL, 3.03 ml) was dissolved in pyridine (100 ml), and 3-nitrobenzoyl chloride (22 fractions, .1 g) was added. After stirring at room temperature for 2 hours, the solvent was distilled off, the residue was dissolved in ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate. After collecting and drying the organic layer, the residue was dissolved in methanol (100 ml). 5% Palladium-activated carbon was added, and the mixture was stirred for 1 hour in the presence of hydrogen. The reaction system was filtered through celite and concentrated, and the obtained solid was washed with ether to obtain the desired product (4.6 g, 99%).

HPLC (revesed): Rt. (Min) = 4.21

 MS (APCI, m / z): 235. Reference example

3- {4,6-dihydroxy-pyrimidine-2-yl-amino} -N-hexyl-N-methyl-ben Zuamide

 The target compound (926 mg, 54%) was purified by reacting the 3-amino-1-N-hexyl-N-methyl-benzamide (5 ol) prepared in Reference Example 226 in the same manner as in Reference Example 35. Obtained.

 HPLC (revesed): Rt. (Min) = 3.78

MS (APCI, m / z): 345. Reference Example 228

 3- {4,6-dihydrazino-pyrimidine-2-ylamino} -N-hexyl-N-methyl-benzamide

 Purified by reacting 3- {4,6-dihydroxy-pyrimidine-2-ylamino} -N-hexyl-N-methyl-benzamide (1 ol) prepared in Reference Example 227 in the same manner as Reference Example 14. Then, the desired product was obtained.

HPLC (revesed): Rt. (Min) = 3.27

MS (APCI, m / z): 373. Reference Example 229

 2- (3- (1,1,2,2-'enylamino) 1-4,6-dihydroxypyrimidine

 The target compound (885 mg, 55%) was obtained by reacting with 3- (1,1,2,2-tetrafluoroethoxy) aniline (5-bandol) in the same manner as in Reference Example 35 and purifying it. Was.

HPLC (revesed): Rt. (Min) = 3.64

MS (APCI, m / z): 320. Reference Example 230

 2— '(3- (1,1,2,2-tetrafluoroethoxy) phenylamino) 1,4,6-dihydrazinopyrimidine

Similar to Reference Example 14 from 2- (3- (1,1,2,2-tetrafluoroethoxy) phenylamino) produced in Reference Example 229 from 1,4,6-dihydroxypyrimidine (1 ol) The desired product was obtained by reaction according to the method and purification.

HPLC (revesed): Rt. (Min) = 3.12

MS (APCI, m / z): 348. Reference Example 231

 3-amino-N-phenyl-N-methyl-benzamide

 The N-methyl-aniline (30 mmol, 3.7 g) and 4-nitrobenzoyl chloride (20 mmol, 3.7 g) were reacted and purified in the same manner as in Reference Example 22 to purify the desired compound ( 4. 04 g, 90 was obtained.

HPLC (revesed): Rt. (Min) = 3.57

MS (APCI, m / z): 227. Reference Example 232

 4- (4,6-dihydroxy-pyrimidine-2-ylamino) -N-phenyl-N-methyl-benzamide

 Reference Example 23 The 3-amino-N-phenyl-N-methyl-benzamide (5 ramol) produced in 31 was reacted and purified in the same manner as in Reference Example 35 to give the desired product (640 mg, 38%). Obtained.

 HPLC (revesed): Rt. (Min) = 3.17

MS (APCI, m / z): 337. Reference Example 233

 4- (4,6-dihydrazino-pyrimidine-2-ylamino) -N-phenyl-N-methyl-benzamide

 Reference Example 23 4- (4,6-dihydroxy-pyrimidine-2-ylamino) -N-phenyl-N-methyl-benzamide (1 mmol) produced in 32 was reacted in the same manner as in Reference Example 14 and purified. Then, the desired product was obtained.

HPLC (revesed): Rt. (Min) = 2.78

MS (APCI, m / z): 365. PC Lano 16

373

Reference Example 234

 4-amino-N-hexyl-N-methyl-benzamide

 N-Methyl-aniline (20 mmol, 3.03 g) and 412 trobenzozoyl chloride (22 mmol, .1 g) were reacted in the same manner as in Reference Example 226 and purified to obtain the desired product quantitatively. .

 HPLC (revesed): Rt. (Min) = 4.21

MS (APCI, m / z): 235. Reference Example 235

 4-U, 6-dihydroxy-pyrimidine-2-ylamino} -N-hexyl-N-methyl-benzamide

 The 4-amino-N-hexyl-N-methyl-benzamide (5 mmol) produced in Reference Example 234 was reacted and purified in the same manner as in Reference Example 35 to obtain the desired product (733 mg, 48%). Was.

 HPLC (revesed): Rt. (Min) = 3.68

MS (APCI, m / z): 345. Reference Example 236

4-{4,6-Dihydrazino-pyrimidine-2-ylamino} -N-hexyl-N-methyl-benzamide

 The 4- {4,6-dihydroxy-pyrimidine-2-ylamino} -N-hexyl-N-methyl-benzamide (1 mmol) produced in Reference Example 235 was reacted and purified in the same manner as in Reference Example 14 for purification. The target was obtained.

HPLC (revesed): Rt. (Min) = 3.27

MS (APCI, m / z): 373. Reference Example 237

2-((1H-indazole-6-yl) phenylamino) -4,6-dihydroxy Pyrimidine

 Reaction and purification were carried out in the same manner as in Reference Example 35 from 1H-indazole-6-ylamine (4 mmol) to obtain the desired product.

HPLC (evesed): Rt. (Niin) = 2.22

MS (APCI, m / z): 244. Reference Example 238

 2 — ((1H-indazo-1-yl) phenylamino) 1,4,6-dihydrazino pyrimidine

 The 2-((1H-indazo-l-6-yl) phenylamino) -4,6-dihydroxypyrimidine (1 tmol) produced in Reference Example 237 was reacted and purified in the same manner as in Reference Example 221. I got the target.

HPLC (revesed): Rt. (Min) = 2.16

MS (APCI, m / z): 272. Reference Example 239 '

 3- {4,6-dihydroxy-pyrimidine-2-ylamino} _N, N-dimethyl-benzamide

The desired product was obtained by reacting with 3-amino_N, N-dimethyl-benzamide (5 ml) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 2.31

MS (APCI, m / z): 275 ₀ Reference example 240

 3- {4,6-dihydrazino-pyrimidine-2-ylamino} -N, N-dimethyl-benzamide Reference Example 239 3- (4,6-dihydroxy-pyrimidine-2-ylamino) -N, N- The desired product was obtained by reacting with dimethyl-benzamide (1 benzyl) in the same manner as in Reference Example 14 for purification.

HPLC (revesed): Rt. (Min)-2.13

MS (APCI, m / z): 303. Reference Example 241

 2- (α-methanesulfonyl 2,3-dihydro-1H-indole-6-yl) -phenylamino) 1,4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with trimethansulfonyl 2,3-dihydro-1H-indole-6-ylamine (four ol) in the same manner as in Reference Example 35 and purifying it.

HPLC (revesed): Rt. (Min) = 2.69

MS (APCI, m / z): 323. Reference Example 242

 2-((trimethanesulfonyl 2,3-dihydro-1H-indole-6-yl) -phenylamino) -4,6-dihydrazinopyrimidine

 Reference Example 221 was obtained from 2-((1-methanesulfonyl 2,3-dihydro-1Η-indole-l-6-yl) -phenylamino) produced in Reference Example 241 from 1,4,6-dihydroxypyrimidine (one thigh ol). Reaction and purification were carried out in the same manner as in the above to give the desired product.

HPLC (revesed): Rt. (Min) = 2.61

MS (APCI, m / z): 351. Reference Example 243

 2-((1H-indazole-5-yl) phenylamino) -4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 1H-indazole-5-ylamine (4 bandol ol) in the same manner as in Reference Example 35 and purifying it.

HPLC (revesed): Rt. (Min) = 2.08

MS (APCI, m / z): 244. Reference Example 244

2-((1H-indazole-5-yl) phenylamino) 1,4,6-dihydrazino pyrimidine The 2-((1 H-indazo-1-yl) phenylamino) -1,4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 243 was reacted and purified in the same manner as in Reference Example 221. I got something.

HPLC (revesed): Rt. (Min) = 2.00

MS (APCI, m / z): 272. Reference Example 245

 3- {4,6-dihydroxy-pyrimidine-2-ylamino} _N, N-dimethyl-benzenesulfonamide

 Reaction and purification were carried out in the same manner as in Reference Example 35 from 3-amino-N, N-dimethyl-benzenesulfonamide (5 mmol) to obtain the desired product (773 ig, 50%).

HPLC (revesed): Rt. (Min) = 2.97

MS (APCI, m / z): 311. Reference Example 246

 3-(4,6-Dihydrazino-pyrimidine-2-ylaminolate N, N-dimethyl-benzenesulfonamide

 The 3- {4,6-dihydroxy-pyrimidine-2-ylamino} -N, N-dimethyl-benzenesulfonamide (1 mmol) produced in Reference Example 245 was reacted and purified in the same manner as in Reference Example 14, and purified. The desired product was obtained.

HPLC (revesed): Rt. (Min) = 2.52

MS (APCI, m / z): 339 ₀ Reference example 247

 2- (3,4,5-trifluoroamino) 1,4,6-dihydroxypyrimidine

 The desired product was obtained by reaction and purification from 3,4,5-trifluoraniline (4 marl ol) in the same manner as in Reference Example 35.

¾-image R spectrum (270 MHz, DMS0-d ₆ ) δρριη: 7.72 (dd, 2H, J = 6.5, 10.5 Hz), 5.09 (s, 1H) HPLC (revesed): Rt. (Min) = 3.39

MS (APCI, m / z): 258. Reference Example 248

2- (3,4,5-trifluoroamino) -1,4,6-dihydrazinopyrimidine

 The 2- (3,4,5-trifluoroamino) -1,4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 247 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. Obtained.

Ή-丽 R spectrum (270 MHz, DMS0-d ₆ ) δ ρπι: 8.99 (s, 1H), 7.82-7.76 (m, 2H), 7.56, (s, 2H), 5.67 (s, 1H), 4.26 ( brs, 4H)

HPLC (revesed): Rt. (Min) = 3.03

MS (APCI, m / z): 286. Reference Example 249

 2- (2,4-methoxy-5-chlorophenylamino) 1,4,6-dihydroxypyrimidine

 The desired product was obtained by reaction from 2,4-methoxy-5-chloroaniline (four ol) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 3.09

MS (APCI, m / z): 298. Reference Example 250

 2- (2,4-Methoxy-5-chlorophenylamino) 1,4,6-Dihydrazinopyrimidine

 The 2- (2,4-methoxy-5-chlorophenylamino) produced in Reference Example 249 was reacted and purified from 1,4,6-dihydroxypyrimidine (1 mmol) in the same manner as in Reference Example 14 to obtain the desired product. Obtained.

HPLC (revesed): Rt. (Min) = 3.00

MS (APCI, m / z): 326. PC leakage 216

378

Reference Example 251

 2- (2,4-dimethylphenylamino) -4,6-

 The reaction product was purified from 2,4-dimethylaniline (5 brain ol) in the same manner as in Reference Example 35 to obtain the desired product (490 mg, 42%).

HPLC (revesed): Rt. (Min) = 2.64

MS (APCI, m / z): 232. Reference Example 252

 2- (2,4-dimethylphenylamino) -1,4,6-dihydrazinopyrimidine

 The 2- (2,4-dimethylphenylamino) 1.4,6-dihydroxypyrimidine (1.56 mmol) produced in Reference Example 251 was reacted in the same manner as in Reference Example 14, purified, and purified. 197 mg, 49%).

HPLC (revesed): Rt. (Min) = 2.61.

MS (APCI, m / z): 260. Reference Example 253

 2- (2-Methyl-3-fluorophenylamino) 1,4,6-dihydroxypyrim

The desired product (170 mg, 14 mg) was obtained by reacting and purifying 2-methyl-3-fluoroaniline (5 ol) in the same manner as in Reference Example 35.

HPLC (revesed): Rt. (Min) = 2.58

MS (APCI, m / z): 236. Reference Example 254

2- (2-Methyl-3-fluorophenylamino) 4,6-dihydrazinopyrimi 2- (2-methyl-3-fluorophenylamino) -14,6-dihydroxypyrimidine prepared in Reference Example 253 ( 0.53 mmol) in the same manner as in Reference Example 14. TJP03 / 05216

After purification, the desired product (31 mg, III) was obtained.

HPLC (revesed): i. (Min) = 2.45

MS (APCI, m / z): 264 ₀ Reference example 255

 2- (2-methyl-5-fluorophenylamino) -1,4,6-dihydroxypyrimidine

 It was reacted and purified from 2-methyl-5-fluoroaniline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (228 mg, 19%).

'H-NMR spectrum _{(270 MHz, DMS0-d 6} ) <5 pm: 7.99-7.93 (m, 1H), 7.30-7.15 (m, 1H), 6.87-6.80 (m, 1H), 4.86 (s, 1H ), 2.22 (s, 3H)

HPLC (revesed): Rt. (Min) = 2.70

MS (APCI, m / z): 236 ₀ Reference example 256

 2- (2-methyl-5-fluorophenylamino) 1,6-dihydrazinopyrimidine,

 2- (2-Methyl-5-fluorophenylamino) -4, produced in Reference Example 255

Reaction and purification were carried out from 6-dihydroxypyrimidine (0.81 mmol) in the same manner as in Reference Example 14 to obtain the desired product (46 mg, 22%).

匪 -band R spectrum (270 MHz, DMS0-d ₆ ) dppm: 8.05 (dd, 1H, J = 2.8 Hz, 12.6

Hz), 7,37 (s, 2H), 7.22 (s, 1H), 7.09 (i, 1H, J = 7.7 Hz), 6.61 (di, 1H, J = 3.0 Hz, 8.3 Hz), 5.62 (s, 1H), 2.17 (s, 3H)

 HPLC (revesed): Rt. (Min) = 2.55

MS (APCI, m / z): 264. Reference Example 257.

2- (2-methyl-4-methoxyphenylamino) -4,6-dihydroxypyrim It was reacted and purified from 2-methyl-4-methoxyaniline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (611 mg, 49%).

HPLC (revesed): Rt. (Min) = 2.31

MS (APCI, m / z): 248. Reference Example 258

 2- (2-Methyl-4-methoxyphenylamino) 1,6-dihydrazinopyrimidine 2- (2-methyl-4-methoxyphenylamino) -4,6-dihydroxypyrimidine prepared in Reference Example 257 (1.01) mmol) and purified in the same manner as in Reference Example 14 to obtain the desired product (89 mg, 32%).

HPLC (revesed): Rt. (Min) = 2.36

MS (APCI, m / z): 276. Reference Example 259

 2- (2,3-dimethylphenylamino) -1,4,6-dihydroxypyrimidine

 The desired product (249 mg, 22%) was obtained by reacting with 2,3-dimethylaniline (5-bandol) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 2.55

MS (APCI, m / z): 232. Reference Example 260

 2- (2,3-dimethylphenylamino) 1,4,6-dihydrazinopyrimidine Reference Example 2 2- (2,3-dimethylphenylamino) -4,6-dihydroxypyrimidine prepared in 59 (0.22 cafe ol) and reacted in the same manner as in Reference Example 14 for purification to obtain the desired product.

HPLC (revesed): Rt. (Min) = 2.56

MS (APCI, m / z): 260 (M + l) +. Reference Example 261

 2- (2-Methyl-14-chlorophenylamino) 1,4,6-dihydroxypyrimidine

 Reaction and purification were conducted in the same manner as in Reference Example 35 from 2-methyl-4-chloroaniline (5 mmol) to obtain the desired product (244 mg, 19%).

 HPLC (revesed): Rt. (Min) = 2.971

MS (APCI, m / z): 252 (M + l) +. Reference Example 262

 2- (2-methyl-4-phenylamino) -4,6-dihydrazinopyrimidine

 Reference Example 26 The 2- (2-methyl-4-chlorophenylamino) -1,4,6-dihydroxypyrimidine (0.76 tmol) produced in Reference Example 1 was reacted and purified in the same manner as Reference Example 14 to obtain the desired compound (9 mg, 4%).

HPLC (revesed): Rt. (Min) = 2.76

MS (APCI, m / z): 280 (M + l) +. Reference Example 263

 2- '(3-fluoro- 4-bromophenylamino) 1,4,6-dihydroxypyrimidine

 The desired product was obtained by reacting and purifying 3-fluoro-41-promo-aline (4 ol) in the same manner as in Reference Example 35.

 HPLC (revesed): Rt. (Min) = 3.53

MS (APCI, m / z): 300 (M + l) +. Reference Example 264

 2- (3_fluoro-41-bromophenylamino) 1,4,6-dihydrazinopyrimidine

2- (3-Fluoro-4-bromophenylamino) _4, prepared in Reference Example 263 The desired product was obtained by reacting and purifying 6-dihydroxypyrimidine (1 mmol) in the same manner as in Reference Example 14.

 HPLC (revesed): Rt. (Min) = 3.14

 MS (APCI, m / z): 328 (M + l) +. Reference Example 265

 2-anilino-5-benzyl-4,6-dihydroxypyrimidine

 Reaction and purification were conducted in the same manner as in Reference Example 74 from aniline (4 mmol) to obtain the desired product.

HPLC (revesed): Rt. (Min) = 3.81

MS (APCI, m / z): 294. Reference Example 266

 2-anilino-5-benzyl-1,4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting 2-anilino-5-benzyl-4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 265 by reacting in the same manner as in Reference Example 14 to obtain the desired product.

 HPLC (revesed): Rt. (Min) = 2.91

MS (APCI, m / z): 322. Reference Example 267

 2- (3-fluoro-4-trifluoromethylphenylamino) -1,4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 3-fluoro-4-trifluoromethylaniline (4 ol) in the same manner as in Reference Example 35 for purification.

HPLC (revesed): Rt. (Min) = 3.75

MS (APCI, m / z): 290. Reference Example 268 2- (3-Fluoro-1-trifluoromethylphenylamino) 1,4,6-dihydrazinopyrimidine

 The 2- (3-fluoro-4-trifluoromethylphenylamino) -1,4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 267 was reacted in the same manner as in Reference Example 14 and purified. I got something.

HPLC (revesed): Rt. (Min) = 3.31

MS (APCI, m / z): 318. Reference Example 269

 2-anilino-5-phenyl 2,6-dihydroxypyrimidine

 The desired product was obtained by reacting aniline (4 fractions ol) with phenylmalonic acid getyl ester (12 liters) in the same manner as in Reference Example 35 to purify the product.

¾-NMR spectrum (270 MHz, DMS0-d ₆ ) άρρι: 10.67 (brs, 2H), 8.80 (s, 1H), 7.69 (d, 2H, J = 7.3 Hz), 7.46 (d, 2H, J = 7.6) Hz), 7.34 (i, 2H, J = 7.6 Hz), 7.28 (t, 2H, J = 7.3 Hz), 7.14 (t, 1H, J = 7.6 Hz), 7.06 (t, 1H,

(J = 7.3 Hz)

HPLC (revesed): Rt. (Min) = 3.42

MS (APCI, m / z): 280. Reference Example 270

 2-anilino-5-phenyl-1,4,6-dihydrazinopyrimidine

 The 2-anilino-5-phenyl-4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 269 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product.

圈 -ring R spectrum (270 MHz, DMS0-d ₆ ) <5ppm: 9.03 (s, 1H), 7.87 (d, 2H, J = 7.3 Hz), 7.79-7.18 (m, 7H), 6.88 (t, 1H) , J = 7.3 Hz), 6.23 (s, 2H), 4.4 5 (brs, 4H)

 HPLC (revesed): Rt. (Min) = 2.82

MS (APCI, m / z): 308. Reference Example 271

 2-anilino-5-ethoxy-1,6-dihydroxypyrimidine

 The desired product was obtained by reacting with aniline (4 mmol) and bromomalonic acid getyl ester (12 mmol) in the same manner as in Reference Example 35 for purification.

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) <5 ppm: 10.62 (brs, 2H), 8.60 (s, 1H), 7.60 (d, 2H, J = 7.0 Hz), 7.30 (t, 2H, J = 7.0 Hz), 7.01 (t, 1H, J = 7.0 Hz), 3.81 (q, 2H, J = 7.0 Hz), 1.18 (ί, 3H, J = 7.0 Hz)

HPLC (revesed): Rt. (Min) = 2.72

MS (APCI, m / z): 248. Reference Example 272

 2-anilino-5-ethoxy 4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting with 2-anilino-5-ethoxy-4,6-dihydroxypyrimidine (1 benzyl) produced in Reference Example 271 in the same manner as in Reference Example 14 and purifying it.

¾- 丽 R spectrum (270 MHz, DMS0-d ₆ ) (5 pm: 9.20 (s, 1H), 8.04 (s, 2H), 7.78 (d, 2H, J-8.1 Hz), 7.25 (t, 2H , J = 8.1 Hz), 6.91 (t, 1H, J = 8.1 Hz), 5.86 (brs, 4H), 3.69 (q, 2H, J = 7.0 Hz), 1.28 (t, 3H, J = 7.0 Hz) HPLC (revesed): Rt. (Min) = 2.51

MS (APCI, m / z): 276. Reference Example 273

 2- (3-Methyl-4 monofluorophenylamino) 1,4,6-dihydroxypyrimidine

 The desired product was obtained by reacting and purifying 3-methyl-4-fluoroaniline (4 mmol) in the same manner as in Reference Example 35.

HPLC (revesed): Rt. (Min) = 2.96

MS (APCI, m / z): 236. Reference Example 274

 2- (3-Methyl-4-fluorophenylamino) 1,4,6-dihydrazinopyrimidine

 Reference Example 27 The 2- (3-methyl-4-fluorophenylamino) 14,6-dihydroxypyrimidine (1 t-ol) produced in 73 was reacted and purified in the same manner as in Reference Example 14 to purify it. I got something.

HPLC (revesed): Rt. (Min) = 2.96

MS (APCI, m / z): 264ο Reference example 275

 2-anilino-5-anilino_4,6-dihydroxypyrimidine

 The desired product was obtained by reacting aniline (4 mmol) with anilinomalonate getyl ester (12 ol) in the same manner as in Reference Example 35 to purify the product.

HPLC (revesed): Rt. (Min) = 3.41

MS (APCI, m / z): 295. Reference Example 276.

2-anilino 5-anilino 4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting the 2-anilino-5-anilino-14,6-dihydroxypyrimidine (1 ol) produced in Reference Example 27 5 in the same manner as in Reference Example 14 and purifying it.

 HPLC (revesed): Rt. (Min) = 2.85

MS (APCI, m / z): 323. Reference Example 277

 2-anilino-5-methoxy-4,6-dihydroxypyrimidine

The desired product was obtained by reacting aniline (4 ratio 1) and methoxymalonic acid dimethyl ester (12 mmol) in the same manner as in Reference Example 35 to purify the product. HPLC (revesed): Rt. (Min) = 2.38

MS (APCI, m / z): 234. Reference Example 278

2-anilino-5-methoxy-4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting 2-anilino-5-methoxy-4,6-dihydroxypyrimidine (1 thigh) produced in Reference Example 277 by reacting in the same manner as in Reference Example 14.

 HPLC (revesed): Rt. (Min) = 2.38

MS (APCI, m / z): 262. Reference Example 279

 2- (2,2-difluoro-benzo [1,3] dioxo-l-5-ylamino) 1-4,6-dihydroxypyrimidine

 The desired product was obtained by reaction with 2,2-difluoro-benzo [1,3] dioxol-5-ylamine (four ol) by reacting in the same manner as in Reference Example 35.

HPLC (revesed): Rt. (Min) = 3.45

MS (APCI, m / z): 284. Reference Example 280

 2- (2,2-difluoro-benzo [1,3] dioxo-l-5-ylamino) 1-4,6-dihydrazinopyrimidine

 In the same manner as in Reference Example 221, the 2- (2,2-difluoro-benzo [1,3] dioxol-5-ylamino) -1,4,6-dihydroxypyrimidine (1 marl ol) produced in Reference Example 279 was obtained. Reaction and purification yielded the desired product.

 HPLC (revesed): Rt. (Min): 2.98

MS (APCI, m / z): 312. Reference Example 281 1-Methanesulfonyl 3-acetylpyrrole

 3-Acetylpyrrole (5 ml, 546 mg) was dissolved in DMF (30 ml), and potassium tobutoxy (5 mg, 561 mg) and methanesulfonyl chloride (7.5 mg, 580 ml) were added. The mixture was stirred at 80 ° C for 18 hours. After evaporating the reaction solvent under reduced pressure, an extraction operation was performed with ethyl acetate-water, and the organic layer was concentrated. The obtained residue was purified by silica gel column chromatography to obtain the desired product (285 mg, 31%).

HPLC (revesed): Rt. (Min) = 3.01

MS (APCI, m / z): 188. Reference Example 282

 1-one (4-trifluoromethanesulfonylphenyl) —ethanone

 1- (4-Trifluoromethylthio-phenyl) -ethanone (5 t ol, 1.1 g) was mixed with acetonitrile-tetrachlorodicarbon-water mixture (40 ml, 1: 1: 2, v / v / v ), And ruthenium chloride (10 mg) and sodium periodate (15 liters, 3.2 g) were added, and the mixture was stirred at room temperature for 2 days. After evaporating the reaction solvent under reduced pressure, an extraction operation was performed with ethyl acetate-water, and the organic layer was concentrated. The obtained residue is subjected to silica gel column chromatography.

And purified to give (l.lg, 90%)

HPLC (revesed): Rt. (Min) = 4.58

MS (APCI, m / z): 253ο Reference example 283

 2- (3,4,5-trimethoxyphenylamino) -4,6-dihydroxypyrimidine

 The desired product was obtained by reacting with 3,4,5-trimethoxyaniline (4 mniol) in the same manner as in Reference Example 35 and purifying it.

 HPLC (revesed): Rt. (Min) = 2.51

MS (APCI, m / z): 294. Reference Example 284 2- (3,4,5-trimethoxyphenylamino) 1,4,6-dihydrazinopyrimidine

 The 2- (3,4,5-trimethoxyphenylamino) 1-4,6-dihydroxypyrimidine (1 mmol) produced in Reference Example 283 was reacted and purified in the same manner as in Reference Example 221 to give the desired product. I got

 HPLC (revesed): Rt. (Min) = 2.53

MS (APCI, ni / z): 322. Reference Example 285

2- (3-Methoxy-4-fluorophenylamino) -4,6-dihydroxypyrimidine

 The product was reacted with 3-methoxy-4-fluoroaniline (5 mmol) in the same manner as in Reference Example 35 and purified to obtain the desired product (429 ig, 34%).

Ή-NMR spectrum (270 MHz, DMS0-d ₆ ) δ ριη: 8.81 (s, 1H), 7.47 (dd, 1H, J = 2.0 Hz, 8.0 Hz), 7.17-7.06 (m, 2H), 4.90 (s , 1H), 3.85 (s, 3H)

HPLC (revesed): Ri. (Min) = 2.61

MS (APCI, m / z): 252. Reference Example 286

 2- (3-Methoxy-1-fluorophenylamino) -1,4,6-dihydrazinopyrimidine

 The 2- (3-methoxy-4-fluorophenylamino) -4,6-dihydroxypyrimidine (1.59 mmol) produced in Reference Example 285 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired compound (98 mg, 22%).

-N spectrum (270 MHz, DMS0-d ₆ ) dpp: 8.56 (s, 1H), 7.99-7.96 (m, 1H), 7.36 (s, 2H), 7.10-7.00 (m, 1H), 6.99—6.88 ( m, 1H), 5.56 (s, 1H), 3.79 (s, 3H) HPLC (revesed): Rt. (min) = 2.88

MS (APCI, m / z): 280. Reference Example 287

 2- (2-Ethylphenylamino) -1,4,6-dihydroxypyrimidine

 The desired product (551 mg, 48%) was obtained by reaction from 2-ethylaniline (5 bandol ol) in the same manner as in Reference Example 35 and purification.

HPLC (revesed): Rt. (Min) = 2.60

MS (APCI, m / z): 232. Reference Example 288

 2- (2-Ethylphenylamino) 1,4,6-dihydrazinopyrimidine

 Reference Example 28 The 2- (2-ethylphenylamino) 1.4,6-dihydroxypyrimidine (2.06 η-dish ol) produced in 87 was reacted in the same manner as in Reference Example 14 and purified. Thus, the desired product (70 mg, 13 mg) was obtained.

HPLC (revesed): Rt. (Min) = 2.54

MS (APCI, m / z): 260. Reference Example 289

 2- (2-methyl-5-methoxyphenylamino) -4,6-dihydroxypyrim

It was reacted and purified from 2-methyl-5-methoxyaniline (5 mmol) in the same manner as in Reference Example 35 to obtain the desired product (357 mg, 29%).

HPLC (revesed): Rt. (Min) = 2.51

MS (APCI, m / z): 248 ₀ Reference example 290 '

 2- (2-methyl-5-methoxyphenylamino) 1,4,6-dihydrazinopyrimidine

Reference Example 2 The 2- (2-methyl-5-methoxyphenylamino) -4,6-dihydroxypyrimidine (1.18 imnol) produced in 89 was reacted in the same manner as in Reference Example 14 and purified. I got the target. HPLC (revesed): Rt. (Min) = 2.58

MS (APCI, m / z): 276. Reference Example 291

 2- (3-ethoxyphenylamino) 1,4,6-dihydroxypyrimidine

 The desired product (822 mg, 66%) was obtained by reacting with 3-ethoxyyanine (5-bandol) in the same manner as in Reference Example 35 and purifying it.

HPLC (revesed): Rt. (Min) = 2.91

MS (APCI, m / z): 248. '' Reference Example 292

 2- (3-ethoxyphenylamino) 1,4,6-dihydrazinopyrimidine

 Reference Example 29 The 2- (3-ethoxyphenylamino) -1,4,6-dihydroxypyrimidine (2.75 tmol) produced in Reference Example 1 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired compound ( 90 mg, 12%).

HPLC (revesed): Rt. (Min) = 2.93

MS (APCI, m / z): 276. Reference Example 293

 2- (2-Fluoro-4-ethoxyphenylamino) 1,4,6-dihydroxypyri

Reaction and purification were carried out in the same manner as in Reference Example 35 from 2-fluoro-41-ethoxyaniline (10 mmol) to obtain the desired product (743 mg, 28%).

HPLC (revesed): Rt. (Min) = 2.90

MS (APCI, m / z): 266. Reference Example 294

2- (2-fluoro-41-ethoxyphenylamino) 1,4,6-dihydrazinopyri S-zine The 2- (2-fluoro-41-ethoxyphenylamino) -1,4,6-dihydroxypyrimidine (2.80 R ol) produced in Reference Example 293 was reacted and purified in the same manner as in Reference Example 14 to obtain the desired product. Obtained.

HPLC (revesed): Rt. (Min) = 2.79

MS (APCI, m / z): 294. Reference Example 295

 2- (3-difluoromethoxyphenylamino) -4,6-dihydroxypyrimidine

 It was reacted and purified from 3-difluoromethoxyaniline (5-bandol) in the same manner as in Reference Example 35 to obtain the desired product (310 mg, 23%).

HPLC (revesed): Rt. (Min) = 3.09 '

MS (APCI, m / z): 270. Reference Example 296

 2- (3-difluoromethoxyphenylamino) 1,4,6-dihydrazinopyrimidine

 The desired product was obtained by reacting the 2- (3-difluoromethoxyphenylamino) -1,4,6-dihydroxypyrimidine produced in Reference Example 295 in the same manner as in Reference Example 14 for purification.

 HPLC (revesed): Rt. (Min) = 3.02

MS (APCI, m / z): 298. Reference Example 297

4-Acetylbenzenesulfonyl chloride (2 mmol, 437 mg) was dissolved in dioxane (5 ml), and triethylamine (triple ol, 0.416 ml) and 0.5 M ammonia-dioxane solution (2.4 ol, 4.8 ml) were added. The mixture was stirred at room temperature for 2 hours. After evaporating the reaction solvent under reduced pressure, an extraction operation was performed with ethyl acetate-water, and the organic layer was concentrated. Get PC hiring 216

The residue was purified by recrystallization from ethanol to give the desired product (285 mg, 72%).

 HPLC (revesed): Rt. (Min) = 2.52

MS (APCI, m / z): 200. Reference Example 298

 4-Acetyl-N-methyl-benzenesulfonamide

 The desired product was obtained by reacting and purifying in the same manner as in Reference Example 297.

HPLC (revesed): Rt. (Min) = 3.14

MS (APCI, ra / z): 214. Reference example 299 '

 4-Acetyl-N, N-dimethyl-benzenesulfonamide

 The desired product was obtained by reacting and purifying in the same manner as in Reference Example 297.

HPLC (revesed): Rt. (Min) = 3.68

MS (APCI, m / z): 228. Reference example 300

 1— [4— (Pyrrolidine-1—1sulfonyl) -phenyl] 1ethanone

 The desired product was obtained by reacting and purifying in the same manner as in Reference Example 297.

HPLC (revesed): Rt. (Min) = 4.08

MS (APCI, m / z): 254. Reference Example 301

 4-Acetyl-N-methoxyethyl-benzenesulfonamide

 The desired product was obtained by reacting and purifying in the same manner as in Reference Example 297.

HPLC (revesed): Rt. (Min) = 3.37

MS (APCI, m / z): 258. Reference 302

 4-Acetyl-N-methoxycarbonylmethyl-benzenesulfonamide The reaction was carried out and purified in the same manner as in Reference Example 297 to obtain the desired product.

HPLC (revesed): Rt. (Min) = 3.39

MS (APCI, m / z): 272. Reference Example 303

 1 1 [4— (azetidine 1 1 1 sulfonyl) -phenyl) 1 ethanone

 The desired product was obtained by reacting and purifying in the same manner as in Reference Example 297.

HPLC (revesed): Rt. (Min) = 3.76

MS (APCI, m / z): 240. Reference Example 304

 4 _acetyl-N-n-propyl-benzenesulfonamide

The desired product was obtained by reacting and purifying in the same manner as in Reference Example 297.

HPLC (revesed): Rt. (Min) = 3.96

MS (APCI, m / z): 242. Reference Example 305

 4-Acetyl-N-cyclopropyl-benzenesulfonamide

The desired product was obtained by reacting and purifying in the same manner as in Reference Example 297.

HPLC (revesed): Rt. (Min) = 3.69

MS (APCI, m / z): 240. Reference Example 306

 4-Acetyl-N-ethyl-benzenesulfonamide

The desired product was obtained by reacting and purifying in the same manner as in Reference Example 297.

 HPLC (revesed): Rt. (Rain)-3.58

MS (APCI, m / z): 228 ₀ JP03 / 05216

 394

Reference Example 307

 2,2,2-trifluoro-11- (4-methanesulfoerphenyl) monoethanone 2,2,2-trifluoro-11- (4-methylthiophenyl) monoethanone (5 ramol, 1.1 g) is converted to acetic acid (20 ml), 30% hydrogen peroxide solution (1.4 ml) was added, and the mixture was stirred at 60 ° C for 18 hours. After evaporating the reaction solvent under reduced pressure, an extraction operation was performed with ethyl acetate-water, and the organic layer was concentrated. The obtained residue was added with ether, ground, and filtered to obtain a white solid (1.2 g).

HPLC (revesed): Rt. (Min) = 3.19

MS (APCI, m / z): 253. Test example 1

 Measurement of MLR inhibition

 The test compound was dissolved in dimethyl sulfoxide to a concentration of 10 mg / ml, diluted with a medium, and added to a predetermined concentration. Hemolyzed lymphocytes from humans were prepared from Fibroblasts provided by two different healthy subjects by Ficoll density gradient centrifugation using Ficoll-Paque PLUS (Pharmacia). One of the prepared two types of human blood-dissected lymphocytes was irradiated with 6000 rad X-rays to render them non-proliferative and used as stimulator cells. RPMI medium containing serially diluted test compound, 10% fetal bovine serum, and 5 ηιΜ2 mercaptoethanol, containing 1300000 each of other human blood-disinfected lymphocytes and stimulated cells not irradiated with X-rays The mixture was mixed in 0.2 ml (manufactured by Life Technologies) and cultured in a 96-well round bottom plate (manufactured by Koningu). After 120 hours, [¾] Thymidme (manufactured by Amersham) was added at 25 l / well so that the final radioactivity was 82 kBq / ml, and the cells were further cultured for 16 hours and taken up into cells. The radioactivity was measured using a beta-plate (WALLAC). The 50% inhibitory concentration of each compound was calculated by semi-log plotting the concentration of the compound and the% of the MLR reaction in the absence of the test compound, and the results are shown in Table 1.

【table 1】 16

395 test compound MLR inhibitory activity IC _5. (nM) Example 26.9

 Example 522 1.4

 Example 526 1.0

From the above results, it is clear that the compound of the present invention has an excellent MLR inhibitory action.

Claims

396 Claims General formula (I) (I)

Or the general formula (I I)

 [Where, R ¹ and R ³ are the same or different and are a hydrogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy lower alkyl group, a (mono-lower alkylamino) lower alkyl group, a (g lower alkylamino) lower alkyl group, an aryl An aryl group independently substituted with 1 to 5 groups or an arbitrary group selected from substituent group a, R ² and R ⁴ are the same or different and are independently selected from an aryl group or a substituent group a in which 1 to 5 substituents are independently selected from an aryl group, a heterocyclic group and an arbitrary group selected from a substituent group a Represents 1 to 3 independently substituted heterocyclic groups with any of the following groups; or R ² together with R ¹ and Z or R ⁴ together with R ³ , identical or different, each including the carbon atom to which they are attached, saturated carbocyclic group, saturated heterocyclic group, substituted A saturated carbocyclic group independently substituted with 1 to 5 arbitrary groups selected from group a, or a saturated heterocyclic group independently substituted with 1 to 3 arbitrary groups selected from substituent group a To form A ¹ and A ² are the same or different and each represent a group having the formula —NR ⁷ — (wherein R ⁷ represents a hydrogen atom or a lower alkyl group) or an oxygen atom; R ⁵ is a cycloalkyl group, an aryl group, a heterocyclic group, a lower alkylthio group, a cycloalkyl group independently substituted with 1 to 5 substituents selected from a substituent group a, and a substituent group a An aryl group independently substituted with 1 to 5 groups of any selected group, a heterocyclic group independently substituted with 1 to 3 groups of any group selected from substituent group a, — A group having R ^s , a group having the formula: CH ₂ — E— R ⁸ (wherein  D represents a group having —NH—, an oxygen atom or a sulfur atom,  E represents an oxygen atom, a sulfur atom or a single bond, R ⁸ is a cycloalkyl group, an aryl group, a heterocyclic group, an aralkyl group, a cycloalkyl group independently substituted with 1 to 5 substituents selected from a substituent group a, and a substituent group a Selected from an aryl group independently substituted with 1 to 5 substituents, a heterocyclic group independently substituted with 1 to 3 substituents from any group selected from the substituent group a, or a substituent group a Represents an aralkyl group independently substituted with 1 to 5 arbitrary groups. ) Or the formula—A ³ — NC RSR (where A ³ represents a group having the formula —NR ¹¹ — (wherein R ¹¹ represents a hydrogen atom or a lower alkyl group) or an oxygen atom; R ⁹ is a hydrogen atom, a lower alkyl group, a lower alkoxy lower alkyl group, a (mono-lower alkylamino) lower alkyl group, a (di-lower alkylamino) lower alkyl group, an aryl group or any group selected from substituent group a. Represents an aryl group independently substituted by 1 to 5 groups, R ^{1 ()} is independently an aryl group, a heterocyclic group, or an arbitrary group selected from substituent group a, and is independently an aryl group substituted with 1 to 5 substituents or an arbitrary group selected from substituent group a. Represents 1 to 3 substituted heterocyclic groups, or R ^{1 (1} is an arbitrary group selected from a saturated carbocyclic group, a saturated heterocyclic group, a substituent group a, including a carbon atom to which they are bonded together with R ^9, and independently represents 1 to 5 And independently form a saturated heterocyclic group substituted with 1 to 3 substituted carbon atoms or an arbitrary group selected from substituent group a). R ⁶ is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower Alkyl group, (mono-lower alkylamino) lower alkyl group, (di-lower alkylamino) lower alkyl group, aralkyl group or anilino group,  Substituent group a is a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halogeno lower alkylthio group, a halogeno lower alkyloxy group, a cycloalkyl group, a hydroxy group, a carboxy group, a carboxymethyl group. , Lower alkoxycarbonyl, amino, mono-lower alkylamino, di-lower alkylamino, lower aliphatic acylamino, nitro, cyano, sulfonyl, lower alkylsulfonyl, halogeno lower alkylsulfonyl, arylsulfonyl Group, heterocyclic group sulfonyl group, lower alkylsulfinyl group, arylsulfier group, carbamoyl group, monono lower alkyl group rubamoyl group, G-lower alkyl group rubamoyl group, lower alkyl (aryl) Rubamoyl group, ethylidenehydrazinocarbonyl group, monoruberyloxy group, mono-lower alkyl group rubamoyloxy group, G-lower alkyl group rubamoyloxy group, mono-rubamoylamino group, mono-lower alkyl group rubamoylamino group, Zy lower alkyl group, rubamoylamino group Sulfonylamino group, lower alkylsulfonylamino group, aminosulfonyl group, mono-lower alkylaminosulfonyl group, di-lower alkylaminosulfonyl group, monocycloalkylaminosulfonyl group, mono-lower alkoxylower alkylaminosulfonyl group , Mono lower alkoxycarbonyl lower alkylaminosulfonyl group, Mono force rubamoyl lower alkyl aminosulfonyl group, Mono lower aliphatic acetylaminosulfonyl group, hydroxy (I) A group consisting of a lower alkyl group, an oxo group, an aryl group, an aryloxy group and an aralkyl group. ] Or a pharmacologically acceptable salt thereof, an ester thereof, or another derivative thereof. 2. In Claim 1, A pyrimidine derivative having the general formula (I), a pharmaceutically acceptable salt thereof, an ester or other derivative thereof. 3. In claim 1,  A pyrimidine derivative having the general formula (II), a pharmaceutically acceptable salt thereof, an ester or other derivative thereof. 54. In any one of claims 1 to 3, A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein R ¹ and R ³ are a hydrogen atom. 5. In any one of claims 1 to 3, A pyrimidine derivative or a pharmacologically acceptable salt thereof, wherein R ¹ and R ³ are the same or different and are a lower alkyl group. 6. In any one of claims 1 to 3, A pyrimidine derivative or a pharmacologically acceptable salt thereof, wherein R ¹ and R ³ are the same or different and are each a C ₂ alkyl group.  Fifteen  7. In any one of claims 1 to 3, A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein R ¹ and R ³ are a methyl group. 8. In any one of claims 1 to 3, 20 R ¹ and R ³ are the same or different and are selected from a lower alkoxy lower alkyl group, a (mono-lower alkylamino) lower alkyl group, a (di-lower alkylamino) lower alkyl group, an aryl group and a substituent group a. Is independently substituted with 1 to 5 groups of the formula: 7: a pyrimidine derivative which is a reel group or a pharmaceutically acceptable salt thereof. 25 9. In any one of claims 1 to 3, R ¹ and R ³ are the same or different and are selected from an aryl group or a substituent group a, a pyrimidine derivative which is independently substituted with 1 to 5 aryl groups, or a pharmacologically acceptable derivative thereof. Salt. 10. In any one of claims 1 to 3, R ² is the same or different as R ¹ and / or R ⁴ is the same as or different from R ³ , including the carbon atom to which they are each attached, saturated carbocyclic group, saturated heterocyclic group, substituted A saturated carbocyclic group independently substituted with 1 to 5 arbitrary groups selected from group a or a saturated heterocyclic group independently substituted with 1 to 3 arbitrary groups selected from substituent group a Or a pharmacologically acceptable salt thereof. 1 1. In any one of claims 1 to 3, R ² together with R ¹ and Z or R ⁴ together with R ³ may be the same or different and may each be fused to a benzene ring, including the carbon atom to which they are attached, C ₄ — C ₇ saturated carbocyclic group, 5- to 6-membered saturated heterocyclic group, substituted one to five independently any group selected from substituent group a, which may be condensed with a benzene ring C "C ₇ A pyrimidine derivative or a pharmacologically acceptable salt thereof, which forms a 5- to 6-membered saturated heterocyclic group independently substituted with 1 to 3 saturated carbon ring groups or an arbitrary group selected from substituent group a. 1 2. In any one selected from claims 1 to 3, R ² together with R ¹ and / or in R ⁴ is together with R ^3, same or different, each including a carbon atom to which it we are attached, may be fused with a benzene ring C ₅ - C ₆ saturated carbocyclic group, tetrahydrothiophene ring group, tetrahydropyran ring group, piperidine ring group, benzene ring which is independently substituted with 1 to 5 arbitrary groups selected from substituent group a A condensable C ₅ -C ₆ saturated carbocyclic group or a tetrahydrothiophene ring, a tetrahydropyran ring or a pyridyl group independently substituted with 1 to 3 arbitrary groups selected from a substituent group aぺ A pyrimidine derivative forming a lysine ring group or a pharmacologically acceptable salt thereof. ' 1 3. In any one of claims 1 to 3, R ² may be the same or different as R ¹ and Z or R ⁴ may be the same as or different from R ³ , each including the carbon atom to which they are bonded, and may be fused to a benzene ring C ₅ _ C ₆ saturated carbocyclic group, or a 1 to be five independently substituted with any group selected from substituent group a Further, a pyrimidine derivative or a pharmacologically acceptable salt thereof which forms a C ₅ -C ₆ saturated carbocyclic group which may be condensed with a benzene ring. 1 4. In any one of claims 1 to 3, R ² is together with R ¹ and Z or R ⁴ together with R ³ , identical or different, each including the carbon atom to which they are attached, an indane group, 1, 2, 3, 4-tetrahydro A naphthalene group or an indane or a 1,2,3,4-tetrahydronaphthalene group substituted with 1 to 3 substituents (the substituents are a lower alkoxy group, a lower aliphatic acylamino group, a lower alkylsulfonyl group and a cyano group) Or a pharmacologically acceptable salt thereof. 15. In any one of claims 1 to 3, R ² together with R ¹ and Z or R ⁴ together with R ³ , identical or different, each including the carbon atom to which they are attached, an indane group, 1,2,3,4-tetrahydro A pyrimidine derivative or a pharmacologically acceptable salt thereof which forms an indane or a 1,2,3,4-tetrahydronaphthalene group substituted with 1 to 3 naphthalene groups or lower alkoxy groups. 16. In any one of claims 1 to 9, R ² and R are the same or different and are independently 1 to 5 arbitrary groups selected from an aryl group, a 5- to 6-membered heterocyclic group which may be condensed with a benzene ring, and a substituent group a. A pyrimidine derivative or a 5- or 6-membered heterocyclic group which is independently substituted with 1 to 3 substituted aryl groups or an arbitrary group selected from substituent group a, and which may be condensed with a benzene ring, or Its pharmacologically acceptable salts. 17. In any one of claims 1 to 9, R ² and R ⁴ are the same or different and are C ₆ —. Aryl group, furyl, phenyl, pyrenyl, pyrazolyl, imidazolyl, thiazolyl, bilanyl, pyridyl, 1,3-dioxolanyl or 1,3-dioxanyl group which may be condensed with a benzene ring, • 402 C ₆ — C, which is independently substituted with 1 to 5 arbitrary groups selected from the substituent group a. 1 to 3 independently substituted with an aryl group or an arbitrary group selected from the substituent group a, which may be condensed with a benzene ring, furyl, phenyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, vilanyl A pyrimidine derivative which is a 1,3-dioxolanyl or 1,3-dioxanyl group or a pharmacologically acceptable salt thereof. 18. In any one of claims 1 to 9, R ² and R ⁴ are the same or different and are selected from a phenyl group, a naphthyl group, a thienyl group, a thiazolyl group, a pyridyl group, a quinolyl group, a 1,3-benzodioxolanyl group, and a substituent group a Phenyl, thiazolyl, pyridyl, quinolyl, or phenyl or thiazolyl, pyridyl, quinolyl, or phenyl or naphthyl independently substituted with 1 to 5 arbitrary groups, or 1 to 3 independently substituted with any group selected from substituent group a. A pyrimidine derivative or a pharmacologically acceptable salt thereof, which is a 1,3-benzodioxolar group. 1 9. In any one selected from claims 1 to 9, R ² and R ⁴ are the same or different and are phenyl, naphthyl, phenyl, thiazolyl, pyridyl, quinolyl, 1,3-benzodioxolanyl or 1 to 3 substituents; A phenyl, naphthyl, chenyl, thiazolyl, pyridyl, quinolyl or 1,3-benzodioxolanyl group substituted with a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group, a nitro group , A cyano group, a lower alkoxycarbonyl group, an aliphatic acylamino group, a lower alkylsulfonyl group, an aminosulfonyl group, a mono-lower alkylaminosulfonyl group, a monocycloalkylaminosulfonyl group and a di-lower alkylaminosulfonyl group A pyrimidine derivative or a pharmaceutically acceptable derivative thereof. Salt. 20. In any one of claims 1 to 9, R ² and R ⁴ are the same or different and are phenyl, 2,3,6-trifluorophenyl, 4-methylsulfonylphenyl, 4-ethylsulfonylphenyl, 2,6 Difluorophenyl, 2,3-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2-, 3- or 4-cyanophenyl, 3,4-dimethoxy-6-nitophenyl phenyl, 4-methoxycarbonylphenyl 4-ethoxycarbonylphenyl, 4-acetylacetylaminophenyl, 2-chloro-5-nitrophenyl, 3-hydroxy-6-nitrophenyl, 4-aminosulfonylphenyl, 4-methylaminosulfonylphenyl, 4 -Ethylaminosulfonylphenyl, 4-propylaminosulfonylphenyl, 4-cyclopropylaminosulfonylphenyl, 4-dimethylaminosulfonylphenyl, 2-chloroquinoline-3-yl, pyridine-13-yl , 4-pyridine, pyridine, 2-thiophene, 1,3-benzodioxolan-6-yl, 1,3-benzo 7-yl, 5-nitro-1,3-benzodioxolan 6-yl, 6-two-row 1, 3-benzodioxolan-7-yl, 5-chloro-1,3-benzodioxolan Pyrimidine derivative which is a 6-yl or 6-chloro-1,3-benzo-1,7-benzoyl or 2,4-dimethyl-1,3-thiazo-lu-5-yl group or its pharmacologically acceptable salt. 2 1. In any one of claims 1 to 9, R ² and R ⁴ are the same or different and are phenyl, 4-cyanophenyl, 4-methylsulfonylphenyl, 4-ethylsulfophenyl, 4-acetylaminophenyl, 3,4-dimethoxy-6- 2-trophenyl, 4-aminosulfonylphenyl, 4-methylaminosulfonylphenyl, 4-ethylaminosulfonylphenyl, 4-propylaminosulfonylphenyl, 4-cyclopropylaminosulfonylphenyl, 4-dimethylaminosulfonylphenyl A pyrimidine derivative which is a pyridine-14-yl or thiophene-12-yl group, or a pharmacologically acceptable salt thereof. 22. In any one selected from claims 1 to 21, A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein A ¹ and A ² are groups having one NH—. 404 23. In any one selected from claims 1 to 21, A pyrimidine derivative or a pharmacologically acceptable salt thereof, wherein A ¹ and A ² are oxygen atoms. 2 4. In any one of claims 1 to 23, R ⁵ is independently selected from a cycloalkyl group, an aryl group, a heterocyclic group, and a cycloalkyl group substituted with 1 to 5 arbitrary groups selected from the substituent group a, and a substituent group a A pyrimidine derivative which is a heterocyclic group independently substituted with 1 to 3 aryl groups or 1 to 3 independently substituted with any group selected from substituent group a, or a pharmacologically acceptable derivative thereof; Acceptable salt. 25. In any one of claims 1 to 23, A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein R ⁵ is a cycloalkyl group or a heterocyclic group. 26. In any one of claims 1 to 23, Salt R ⁵ is, C "C _s cycloalkyl group, allowed pyrimidine derivative or a pharmacologically a benzene ring condensed with double heterocyclic group may 5 to 6 membered. 27. In any one of claims 1 to 23, A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein R ⁵ is a cyclopropyl group, an indolyl group or an indolinyl group. 28. In any one of claims 1 to 23, Is a group having the formula D—R ⁸ (wherein R ⁸ has the same meaning as described above) or a pharmacologically acceptable salt thereof. 2 9. In claim 28, D is a pyrimidine derivative or a pharmacologically acceptable salt thereof, which is a group having one NH—. 30. In any one of claims 28 or 29, R ⁸ is C ₆ —. C ₆ —C i which is independently substituted with 1 to 5 arbitrary groups selected from an aryl group, a 5- to 6-membered aromatic heterocyclic group which may be condensed with a benzene ring, and a substituent group a. A pyrimidine derivative, which is a 5- to 6-membered aromatic heterocyclic group which may be condensed with a benzene ring, which is independently substituted with 1 to 3 aryl groups or an arbitrary group selected from the substituent group a, or a pharmacology thereof. Above acceptable salts. . 31. In any one of claims 28 or 29, R ⁸ is C ₆ —C _t . A C ₆ — C _1D aryl group independently substituted with 1 to 3 independently selected from an aryl group, a pyridyl group, a phenyl group, a benzodioxolanyl group, a benzodioxanyl group or a substituent group a. A pyrimidine derivative or a pharmacologically acceptable salt thereof. 32. In any one of claims 28 or 29, R ⁸ represents a phenyl group, a pyridyl group, a phenyl group, a benzodioxolanyl group, a benzodioxanyl group, or a phenyl group substituted with 1 to 3 substituents (the substituents are a halogen atom, a lower alkyl group, A lower alkyl group, a lower alkoxy group, a lower alkylthio group and an aryl group.) Or a pharmacologically acceptable salt thereof. 33. In any one of claims 28 or 29, R ⁸ is phenyl, 2-, 3- or 4-fluorophenyl, 2_, 3_ or 4-chlorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl , 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,3,4-trifluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl 2-, 2-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 21-ethoxyphenyl, 2-methylthiophenyl, 3,5-dimethoxyphenyl, 2 —Fluoro-4-cyclophenyl, 2-fluoro-5-chlorophenyl, 2-fluoro-4-methylphenyl, 2-fluoro-5-methylphenyl, 2-fluoro-5-trifluoromethylphenyl, 2-methoxy-5— Methylphenyl, 2-methoxy-5-t-butylphenyl, 2-fluoro-4-methoxyphenyl, 4-fluoro-3-methoxyphenyl, 2-methoxy-5-phenylphenyl, 1,3-benzodioxolan-1-yl , 1,4-benzodioxane-16-yl or pyridine-3-yl pyrimidine derivatives or their pharmacologically acceptable salt. 3 4. In any one of claims 28 or 29, R ⁸ is a phenyl or 2-methoxyphenyl group pyrimidine derivative or a pharmacologically acceptable salt thereof. 35. In any one selected from claims 1 to 34, R ⁵ is a pyrimidine derivative which is a group having the formula A ³ —N = CR ⁹ R ^{1 ()} (where A ³ , R ⁹ and R ′ ^Q have the same meanings as described above) Or a pharmacologically acceptable salt thereof. 3 6. In claim 35, A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein A ³ is a group having one NH—. . 3 7. In claim 35 or 36, A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein R ⁹ is a methyl group or a hydrogen atom. 38. In any one selected from claims 35 to 37, R ¹⁰ is phenyl, 4-cyanophenyl, 4-methylsulfonylphenyl, 4 Pyrimidine derivatives which are acetylacetylaminophenyl, 3,4-dimethoxy-16-ditrophenyl, pyridin- _4- yl or thiophen-2-yl groups, or pharmaceutically acceptable salts thereof.  39. In any one of claims 1 to 35, R ^1!) Together with R ⁹ are the same or different and each includes a carbon atom to which they are bonded, and is an indane group, a 1,2,3,4-tetrahydronaphthalene group or a lower alkoxy group. Or a pyrimidine derivative or a pharmacologically acceptable salt thereof which forms an indane or a 1,2,3,4-tetrahydrona 'group substituted by 3 or more. 40. In any one of claims 1 to 39, A pyrimidine derivative or a pharmaceutically acceptable salt thereof, wherein R ⁶ is a hydrogen atom. 41. In any one selected from claims 1 to 39, R ⁶ force Lower alkyl group, lower alkoxy group, lower alkoxy lower alkyl group, (mono-lower alkylamino) lower alkyl group, (Gi-lower alkylamino) lower alkyl group or aralkyl group, or a pharmaceutically acceptable pyrimidine derivative. salt. 4 2. In any one of claims 1 to 39, A pyrimidin derivative or a pharmaceutically acceptable salt thereof, wherein R ⁶ is a lower alkyl group, a lower alkoxy group or an aralkyl group. 4 3. In any one of claims 1 to 39, A pyrimidine derivative wherein R ⁶ is a C 1, 1 C ₂ alkyl group, a C, 1 C ₂ alkoxy group or a benzyl group, or a pharmaceutically acceptable salt thereof. 4 4. In claim 1,  卜 (4-pyridinyl)-エ ethanone N- (2- (2-fluoroalirino)-6- {2-[（(4 -pyri -4-pyrimidinyl) hydrazone, 1- (4-pyridinyl) -triethanone N- (2-anilino-6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,  Tri (4-pyridinyl) -1-ethanone N- (2- (3-methoxyanilino) -6- {2- [1- (4-pyridinyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,  1- (4-Methylsulfamoylofenyl) -triethanone N- (2-anilino-1-6- [2- (2- (4-methylsulfamoylofenyl) ethylidene] hydrazino} -4-pyrimiditol (4 -Pyridyl) -triethanone N- (2- (benzo [1,3] dioxol-5-ylamino) -1-6- {2- [1- (4-pyridyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone ,  1- (4-ethylsulfonylphenyl)-1-ethanone N- (2-anilino-6- {2- [1- (4-ethylsulfonylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone  1- (4-cyclopropylsulfamoyl-phenyl) -triethanone N- (2-anilino-1-6-[2- [1- (4-cyclopropylsulfamoylofenyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone,  1- (4-Methylsulfamoylophenyl)-1-ethanone N-(2- (2,4,5-trifluoroalumino) — 6- {2- [tri (4-methylsulfur Moyl-Feninole) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,  1- (4-Methylsulfamoylofenyl) -triethanone N- (2- (2-fluoroallylinyl) _6-{2- [tri (4-methylsulfamoyl-phenyl) ethylidene] hydrazino}- 4-pyrimidinyl) hydrazone,  U- (4-ethylsulfamoylofenyl) -1--ethanone N- (2-anilinol 6- {2-[[(4-ethylsulfamoylofenyl) ethylidene] hydrazino 4-pyrimidi-2-yl) hydrazone,  1- (4-methylsulfamoylofenyl) -triethanone N- (2- (2,3,4-trifluoranilino) -1-6- (2- [1-(4-methylsulfamoyl-phenyl)) Ethylidene] hydrazino} -4-pyrimidinyl) hydrazone, 1- (4-methylsulfamoyl-phenyl) -1 -ethanone N- (2- (2-fluoro-4- 409 chloroanilino) i 6- {2- [1- (4-Methylsulfamoylenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,  1- (4-Methylsulfamoylphenenyl) -triethanone N- (2- (3-methoxyanilino) -1-6- {2- [1- (4-Methylsulfamoyl-phenyl) ethylidene] hydrazino} -4 -Pyrimidinyl) hydrazone,  Tri (4-methylsulfamoyl-phenyl) -triethanone N- (2-anilino-5-ethoxy) 6-- {2- [1- (4-methylsulfamoyl-phenyl) ethylidene] hydrazino} _4- Pyrimidinyl) hydrazone,  1- (4-Methylsulfamoylphenyl) -triethanone N- (2- (3,5-difluora nilino) -6- {2_ [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino} -4-pyrimidinyl) hydrazone,  1- (4-methylsulfamoylphenyl)-1-ethanone N- (2- (3,4,5-trifluoroanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] Hydrazino} -4-pyrimidinyl) hydrazone,  1- (4-Methylsulfamoylphenyl) -triethanone N- (2-anilino-5-benzyl-6- {2- [1- (4-Methylsulfamoylphenyl) ethylidene] hydrazino}-4- Pyrimidinyl) hydrazone,  1- (4-methylsulfamoylphenyl)-1-ethanone N- (2- (3,4-difluoroarilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene ] Hydrazino 4-pyrimidinyl) hydrazone,  1- (4-methylsulfamoylphenyl) -1-ethanone N- (2- (3-fluoranilylimidinyl) hydrazone,  Tri (4-methylsulfamoylphenyl) -triethanone N- (2- (benzo [1,3] dioxole-5-yl-amino) -6- {2- [1- (4-methylsulfamoylphenyl) Enil) ethylidene] hydrazino} -4-pyrimidier) hydrazone,  1- (4-Methylsulfamoylphenyl) -triethanone N- (2- (2,4-difluoroarilino) -6- {2- [1- (4-Methylsulfamoylphenyl) 4-pyrimidinyl) hydrazone, Tri (4-methylsulfamoylphenyl) -triethanone N- (2- (2-methoxyanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino 4-pyrimidinyl ) Hydrazone,  Tri (4-methylsulfamoylphenyl) -triethanone N- (2- (2-fluoro-5-chloroanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] Hydrazino} -4-pyrimidinyl) hydrazone,  1- (4-Methylsulfamoylphenyl) -triethanone N- (2- (4-chloroanilino) -6- {2- [1- (4-methylsulfamoylphenyl) ethylidene] hydrazino} -4- Pyrimidinyl) hydrazone,  1- (4-Methylsulfamoylphenyl) -triethanone N- (2- (2-Fluoro-4-methoxyanilino) -6- {2- [1- (4-Methylsulfamoylphenyl) ethylidene] h Drazino} -4-pyrimidinyl) hydrazone,  1- (4-Methylsulfamoylphenyl) -1-ethanone N- (2- (3-Methoxy-4-fluoroanilino) _6- {2- [tri (4-methylsulfamoylphenyl) ethylidene] hidden Razino} -4-pyrimidinyl) hydrazone and  1- (4-Ethylsulfamoylphenyl) -triethanone N- (2- (3-Fluoroalylino) -6--[1- (4-Ethylsulfamoylphenyl) ethylidene] hydrazino} + Pyrimidinyl) hydrazone Or a pharmacologically acceptable salt thereof, selected from the group consisting of: 45. A pharmaceutical composition comprising, as an active ingredient, the compound according to any one of claims 1 to 44, a pharmacologically acceptable salt thereof, an ester thereof, or another derivative thereof. 46. The pharmaceutical composition according to claim 45, wherein the pharmaceutical composition is a composition for inhibiting a mixed lymphocyte culture reaction. 4 7. The pharmaceutical composition suppresses rejection of grafts in bone marrow transplantation, organ transplantation, etc. or inhibits inflammatory diseases, organ-specific autoimmune diseases, non-organ-specific autoimmune diseases. 46. The pharmaceutical composition according to claim 45, which is a composition for preventing and / or treating allergic diseases. 4 8. Pharmaceutical composition with rheumatoid arthritis, multiple sclerosis, inflammatory bowel disease, diabetes, glomerulonephritis, primary biliary cirrhosis, chronic active hepatitis, pernicious anemia, Hashimoto's thyroiditis, atrophic gastritis, severe The pharmaceutical composition according to claim 45, which is a composition for preventing and treating Z or treating myasthenia, psoriasis, Siedalen syndrome, systemic lupus erythematosus, rhinitis, asthma or atopic dermatitis. 49. The pharmaceutical composition according to claim 45, wherein the pharmaceutical composition is a composition for suppressing cancer cells. 50. The pharmaceutical composition according to claim 45, wherein the pharmaceutical composition is a composition for suppressing cancerous lymphocytes. 51. The pharmaceutical composition according to claim 45, wherein the pharmaceutical composition is a composition for suppressing rejection of a transplant in bone marrow transplantation or organ transplantation, or for preventing and / or treating rheumatoid arthritis. 52. Use of the compound according to any one of claims 1 to 44, a pharmacologically acceptable salt thereof, an ester thereof, or another derivative thereof for producing a pharmaceutical composition. 53. The use according to claim 52, wherein the pharmaceutical composition is a composition for inhibiting a mixed lymphocyte culture reaction. 5 4. The pharmaceutical composition suppresses rejection of grafts in bone marrow transplantation, organ transplantation, etc. or prevents inflammatory diseases, organ-specific autoimmune diseases, non-organ-specific autoimmune diseases or allergic diseases, and Z Or a composition for treatment. Use according to 2. 5 5. Pharmaceutical composition with rheumatoid arthritis, multiple sclerosis, inflammatory bowel disease, diabetes, glomerulonephritis, primary biliary cirrhosis, chronic active hepatitis, pernicious anemia, Hashimoto's thyroiditis, atrophic gastritis, severe 53. The use according to claim 52, which is a composition for the prevention and / or treatment of myasthenia, psoriasis, Siedalen syndrome, systemic lupus erythematosus, rhinitis, asthma or atopic dermatitis. 56. The use according to claim 52, wherein the pharmaceutical composition is a composition for suppressing cancer cells. 57. The use according to claim 52, wherein the pharmaceutical composition is a composition for suppressing cancerous lymphocytes. 58. The use according to claim 52, wherein the pharmaceutical composition is a composition for suppressing rejection of a transplant in bone marrow transplantation, organ transplantation or the like, or for preventing or treating rheumatoid arthritis. 59. Administer a pharmacologically effective amount of the compound according to any one of claims 1 to 44, a pharmaceutically acceptable salt thereof, an ester or other derivative thereof to a warm blooded animal. Bone marrow transplantation · A method for suppressing rejection of transplants in organ transplantation. 60. A pharmacologically effective amount of the compound according to any one of claims 1 to 44, a pharmaceutically acceptable salt thereof, an ester thereof, or another derivative thereof is administered to a warm blooded animal. Prevention and Z or treatment method of the disease. ' 61. The method according to claim 60, wherein the disease is an inflammatory disease, an organ-specific autoimmune disease, a non-organ-specific autoimmune disease, or an allergic disease. 6 2. Disease is rheumatoid arthritis, multiple sclerosis, inflammatory bowel disease, diabetes, glomerulonephritis, primary biliary cirrhosis, chronic active hepatitis, pernicious anemia, Hashimoto's thyroiditis, atrophic gastritis, skeletal muscle The method according to claim 60, which is asthenia, psoriasis, Siedalen syndrome, systemic lupus erythematosus, rhinitis, asthma or atopic dermatitis. 63. The method according to claim 60, wherein the disease is rheumatoid arthritis. 6 4. Administer a pharmacologically effective amount of the compound according to any one of claims 1 to 44, a pharmaceutically acceptable salt thereof, an ester or other derivative thereof to a warm blooded animal. Of inhibiting cancer cells. 65. The method according to claim 64, wherein the cancer cells are cancerous lymphocytes. 66. The method according to any one of claims 59 to 65, wherein the warm-blooded animal is a human.