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PE68599A1 - PROTEASE INHIBITORS - Google Patents

PROTEASE INHIBITORS

Info

Publication number
PE68599A1
PE68599A1 PE1998000303A PE00030398A PE68599A1 PE 68599 A1 PE68599 A1 PE 68599A1 PE 1998000303 A PE1998000303 A PE 1998000303A PE 00030398 A PE00030398 A PE 00030398A PE 68599 A1 PE68599 A1 PE 68599A1
Authority
PE
Peru
Prior art keywords
compound
refers
formula
aryl
alkyl
Prior art date
Application number
PE1998000303A
Other languages
Spanish (es)
Inventor
Scott Kevin Thompson
Daniel Frank Veber
Stacie Marie Halbert
Richard Mcculloch Keenan
Renee Louis Desjarlais
Kevin James Duffy
Evelyne Michaud
Original Assignee
Smithkline Beecham Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp
Publication of PE68599A1 publication Critical patent/PE68599A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/22—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
    • C07C335/26—Y being a hydrogen or a carbon atom, e.g. benzoylthioureas
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/285—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

SE REFIERE A UN COMPUESTO DERIVADO DE ARIL Y HETEROARIL TIAZOLO DE FORMULA I, SU SAL O SOLVATO; DONDE R1 ES UN ANILLO AROMATICO O HETEROAROMATICO CON 1-4 N, O o S; R2 Y R3 SON H, ALQUILO C1-C8. ARILO, ARIL-ALQUILO C1-C8 o HETEROARILO; R4 ES UN ANILLO AROMATICO, HETEROAROMATICO CON 1-4 N, O Y S o UNA AMINA; "W", "X" E "Y" SON CH, N, S Y O; Y ADEMAS a)CUANDO W ES N, X ES O E "Y" ES CH, R4 NO ES Ph; b)CUANDO R4 ES PIRIDINILO, R1 NO ES TIAZOLILO SUSTITUIDO CON CO2R. TAMBIEN SE REFIERE A UN COMPUESTO DE FORMULA II DONDE R7 ES H, -OPh, -CH(CH3)2 Y PhNHCO-; R8 ES H, CH3, -OCH3; R9 ES H, -CH2CH(CH3), Br, ENTRE OTROS. TAMBIEN SE REFIERE A UN COMPUESTO DE FORMULA III, DONDE: R10 ES PhNHCO Y (4-Py)CH2O-; R11 ES -OCH2CH2CH3 Y -OCH2CH3; R12 ES H, -CH2OCH2CH3, -CH2OCH3, ENTRE OTROS; TAMBIEN SE REFIERE A UN COMPUESTO DE FORMULA IV, DONDE R13 A R18 SON ALQUILO C1-C8, ALQUIL C1-C8-ETER, ARILO, ENTRE OTROS. UN COMPUESTO PREFERIDO ES N-[2-(2-BENCILOXIFENIL)TIAZOL-4-ILCARBONIL]-N`-(4-FENOXIFENIL)HIDRAZIDA. EL COMPUESTO I INHIBE A UNA CISTEINA PROTEASA COMO LA CATEPSINA K O UNA SERINA PROTEASA, PUDIENDO SER UTIL PARA TRATAR UNA ENFERMEDAD CARACTERIZADA POR PERDIDA OSEA COMO LA OSTEOPOROSIS, PERIODONTITIS, GINGIVITIS O TRATAR UNA ENFERMEDAD CARACTERIZADA POR UNA DEGRADACION EXCESIVA DE CARTILAGO O MATRIZ COMO OSTEOARTRITIS, ARTRITIS REUMATOIDEIT REFERS TO A COMPOUND DERIVED FROM ARIL AND HETEROARIL TIAZOLO FROM FORMULA I, ITS SALT OR SOLVATE; WHERE R1 IS AN AROMATIC OR HETEROAROMATIC RING WITH 1-4 N, O or S; R2 AND R3 ARE H, ALKYL C1-C8. ARYL, ARYL-C1-C8-ALKYL or HETEROARYL; R4 IS AN AROMATIC, HETEROAROMATIC RING WITH 1-4 N, O AND S or AN AMINE; "W", "X" E "Y" ARE CH, N, S Y O; AND ALSO a) WHEN W IS N, X IS O E "Y" IS CH, R4 IS NOT Ph; b) WHEN R4 IS PIRIDINYL, R1 IS NOT THIAZOLYL SUBSTITUTED WITH CO2R. IT ALSO REFERS TO A COMPOUND OF FORMULA II WHERE R7 IS H, -OPh, -CH (CH3) 2 AND PhNHCO-; R8 IS H, CH3, -OCH3; R9 IS H, -CH2CH (CH3), Br, AMONG OTHERS. IT ALSO REFERS TO A COMPOUND OF FORMULA III, WHERE: R10 IS PhNHCO AND (4-Py) CH2O-; R11 IS -OCH2CH2CH3 AND -OCH2CH3; R12 IS H, -CH2OCH2CH3, -CH2OCH3, AMONG OTHERS; IT ALSO REFERS TO A COMPOUND OF FORMULA IV, WHERE R13 TO R18 ARE ALKYL C1-C8, RENT C1-C8-ETER, ARYL, AMONG OTHERS. A PREFERRED COMPOUND IS N- [2- (2-BENZLOXIFENIL) THIAZOL-4-ILCARBONIL] -N`- (4-PENOXIFENIL) HYDRAZIDE. COMPOUND I INHIBITS A CYSTEINE PROTEASE LIKE CATECHPSINE K OR A SERINE PROTEASE, MAY BE USEFUL TO TREAT A DISEASE CHARACTERIZED BY LOSS OF OSEA LIKE OSTEOPOROSIS, PORIGIAR DISEASE, GINGIVITIS OR TREATMENT OF A CHARACTERISTIC DISEASE RHEUMATOID ARTHRITIS

PE1998000303A 1997-04-25 1998-04-23 PROTEASE INHIBITORS PE68599A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US4490697P 1997-04-25 1997-04-25

Publications (1)

Publication Number Publication Date
PE68599A1 true PE68599A1 (en) 1999-09-26

Family

ID=21934967

Family Applications (1)

Application Number Title Priority Date Filing Date
PE1998000303A PE68599A1 (en) 1997-04-25 1998-04-23 PROTEASE INHIBITORS

Country Status (10)

Country Link
EP (1) EP0977743A1 (en)
JP (1) JP2002501502A (en)
AR (1) AR012603A1 (en)
AU (1) AU7139598A (en)
CA (1) CA2287567A1 (en)
CO (1) CO4950567A1 (en)
MA (1) MA26486A1 (en)
PE (1) PE68599A1 (en)
WO (1) WO1998049152A1 (en)
ZA (1) ZA988479B (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU9110298A (en) * 1998-05-21 1999-12-06 Smithkline Beecham Corporation Protease inhibitors
EP1488791A3 (en) * 1998-09-21 2005-04-06 University Of Florida Research Foundation, Inc. Antimalarial agents
US20030144175A1 (en) 1998-12-23 2003-07-31 Smithkline Beecham Corporation Protease inhibitors
AU1474801A (en) 1999-11-10 2001-06-06 Smithkline Beecham Corporation Protease inhibitors
JP2003513971A (en) 1999-11-10 2003-04-15 スミスクライン・ビーチャム・コーポレイション Protease inhibitor
WO2001034600A1 (en) 1999-11-10 2001-05-17 Smithkline Beecham Corporation Protease inhibitors
CN1416346A (en) 2000-03-21 2003-05-07 史密丝克莱恩比彻姆公司 Peotease inhibitors
KR100962972B1 (en) 2002-07-26 2010-06-09 주식회사유한양행 1-phenylpiperidin-3-one derivatives and preparation method thereof
WO2004050118A1 (en) * 2002-11-29 2004-06-17 Morinaga Milk Industry Co., Ltd. Cysteine protease inhibitor
US20070232586A1 (en) * 2004-04-21 2007-10-04 Kazuyuki Ohmoto Hydrazino-Substituted Heterocyclic Nitrile Compounds and Use Thereof
US8722929B2 (en) 2006-10-10 2014-05-13 Valeant Pharmaceuticals International N-[2-amino-4-(phenylmethoxy)phenyl] amides and related compounds as potassium channel modulators
JP5408434B2 (en) * 2007-07-03 2014-02-05 アステラス製薬株式会社 Amide compounds
US8563566B2 (en) 2007-08-01 2013-10-22 Valeant Pharmaceuticals International Naphthyridine derivatives as potassium channel modulators
US7786146B2 (en) 2007-08-13 2010-08-31 Valeant Pharmaceuticals International Derivatives of 5-amino-4,6-disubstituted indole and 5-amino-4,6-disubstituted indoline as potassium channel modulators
WO2009139373A1 (en) 2008-05-14 2009-11-19 アステラス製薬株式会社 Amide compound
MX2010014461A (en) * 2008-06-24 2011-04-28 Valeant Pharmaceuticals Int Benzyloxy anilide derivatives useful as potassium channel modulators.
WO2010015652A2 (en) * 2008-08-07 2010-02-11 Smithkline Beecham Corporation Thiazole compounds as activators of soluble guanylate cyclase
CN107652200B (en) * 2017-09-07 2019-06-14 陕西科技大学 A kind of method that adopts aromatic hydrazine to synthesize N-aryl secondary aromatic amide
CN113754569B (en) * 2020-06-04 2024-07-02 四川国为制药有限公司 Intermediate compound and preparation method and application thereof

Also Published As

Publication number Publication date
AR012603A1 (en) 2000-11-08
WO1998049152A1 (en) 1998-11-05
AU7139598A (en) 1998-11-24
EP0977743A1 (en) 2000-02-09
CO4950567A1 (en) 2000-09-01
CA2287567A1 (en) 1998-11-05
MA26486A1 (en) 2004-12-20
JP2002501502A (en) 2002-01-15
ZA988479B (en) 1998-10-26

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