RU2005140090A - Способ синтеза гетероциклических соединений - Google Patents
Способ синтеза гетероциклических соединений Download PDFInfo
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- RU2005140090A RU2005140090A RU2005140090/04A RU2005140090A RU2005140090A RU 2005140090 A RU2005140090 A RU 2005140090A RU 2005140090/04 A RU2005140090/04 A RU 2005140090/04A RU 2005140090 A RU2005140090 A RU 2005140090A RU 2005140090 A RU2005140090 A RU 2005140090A
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- 238000000034 method Methods 0.000 title claims 10
- 230000015572 biosynthetic process Effects 0.000 title 1
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000001301 oxygen Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- BGCPLWWYPZAURQ-UHFFFAOYSA-N 5-[[5-chloro-2-(2,2,6,6-tetramethylmorpholin-4-yl)pyrimidin-4-yl]amino]-3-(3-hydroxy-3-methylbutyl)-1-methylbenzimidazol-2-one Chemical group ClC=1C(=NC(=NC=1)N1CC(OC(C1)(C)C)(C)C)NC1=CC2=C(N(C(N2CCC(C)(C)O)=O)C)C=C1 BGCPLWWYPZAURQ-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004177 carbon cycle Methods 0.000 claims 1
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
-
- 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
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- 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
- C07C335/14—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of rings other than 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
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- 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
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- 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
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
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- 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
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (9)
1. Способ получения гетероциклов формулы I,
в которой Х представляет собой серу, кислород или NR5,
причем R5 представляет собой водород или (С1-С4)-алкил;
m и о независимо друг от друга равны нулю, 1 или 2;
А представляет собой фенил, нафтил или гетероарил, все из которых могут быть замещены 1, 2, 3, 4 или 5 остатками R11,
причем R11 независимо друг от друга выбраны из группы, состоящей из (С1-С4)-алкила, F, Cl, Br, I, CN, NO2, OH, O(С1-С4)-алкила, СОО(С1-С4)-алкила, причем атомы водорода в алкильных остатках полностью или частично могут быть замещены атомами фтора; или (С1-С4)-алкил, (С2-С5)-алкенил, (С2-С5)-алкинил, (С3-С8)-циклоалкил, (С4-С8)-циклоалкенил,
причем указанные остатки независимо друг от друга могут быть замещены (С1-С4)-алкилом или (С3-С6)-циклоалкилом, и причем атомы водорода в алкильных, алкенильных, алкинильных, циклоалкильных и циклоалкенильных остатках полностью или частично могут быть замещены атомами фтора;
R14, R15, R16 и R17 независимо друг от друга представляют собой водород, F или (С1-С4)-алкил,
причем атомы водорода в алкильных остатках полностью или частично могут быть замещены атомами фтора; или
R14 и R16 вместе образуют связь, и
R15 и R17 вместе с обоими атомами углерода, с которыми они соединены, образуют ароматический углеродный шестичленный цикл, в котором один или два атома углерода могут быть заменены на азот, или тиофеновый цикл,
причем ароматический углеродный шестичленный цикл и тиофеновый цикл могут быть замещены 1, 2, 3 или 4 остатками R7,
причем R7 независимо друг от друга выбраны из группы, состоящей из (С1-С4)-алкила, F, Cl, Br, I, CN, NO2, OH, O(С1-С4)-алкила и СОО(С1-С4)-алкила, причем атомы водорода в алкильных остатках полностью или частично могут быть замещены атомами фтора; или
R14 и R16 независимо друг от друга представляют собой водород или (С1-С4)-алкил,
причем атомы водорода в алкильных остатках полностью или частично могут быть замещены атомами фтора; и
R15 и R17 вместе с обоими атомами углерода, с которыми они соединены, образуют насыщенный 5-, 6-, 7- или 8-членный углеродный цикл, в котором один или два атома углерода независимо друг от друга могут быть заменены на О, S, NH и N(C1-C4)-алкил и которые могут быть замещены 1, 2, 3, 4, 5 или 6 остатками R8,
причем R8 независимо друг от друга выбраны из группы, состоящей из (С1-С4)-алкила, О(С1-С4)-алкила, СОО(С1-С4)-алкила, причем атомы водорода в алкильных остатках полностью или частично могут быть замещены атомами фтора;
R10, R11, R12 и R13 независимо друг от друга представляют собой водород, F или (C1-C4)-алкил,
причем атомы водорода в алкильных остатках полностью или частично могут быть замещены атомами фтора;
причем либо А, либо цикл, образованный из R15 и R17, при m, равном нулю, представляет собой ароматическую циклическую систему, либо оба они представляют собой ароматические циклические системы; и
причем исключаются соединения, в которых А представляет собой незамещенный фенил или (С1-С4)-алкил, Х представляет собой кислород, R14 и R15 независимо друг от друга представляют собой водород, (С1-С4)-алкил или бензил, R16 и R17 представляют собой водород, и m и о равны нулю;
а также их таутомеров и их солей,
отличающийся тем, что
а) изотиоцианат формулы II взаимодействием с первичным амином формулы III превращают в тиомочевину формулы IV, и
b) тиомочевину формулы IV взаимодействием с сульфохлоридом R6SO2Cl в присутствии основания переводят в соединение формулы I, причем в соединениях формул II, III и IV A, X, n, m и R10 по R17 имеют значения, определенные в формуле I, и
R6 представляет собой (С1-С4)-алкил, трифторметил или фенил, который незамещен или замещен метилом, трифторметилом, F, Cl, Br или полимерным носителем.
2. Способ по п.1, в котором реакцию проводят в одном реакторе.
3. Способ по п.1 и/или 2, в котором стадии а) и b) независимо друг от друга проводят непрерывно или периодически.
4. Способ по п.1 и/или 2, где Х представляет собой кислород или NR5.
5. Способ по п.1 и/или 2, где Х представляет собой NR5.
6. Способ по п.1 и/или 2, где А представляет собой фенил, тиенил или изоксазолил, которые могут быть замещены, как указано в п.1.
7. Способ по п.1 и/или 2, где R6 представляет собой фенил или п-метилфенил.
8. Способ по п.1 и/или 2, где на стадии b) введенное основание представляет собой гидроксид натрия или гидроксид калия.
9. Способ получения соединения формулы I, определенного в п.1,
отличающийся тем, что тиомочевину формулы IV с помощью сульфохлорида R6SO2Cl в присутствии основания переводят в соединение формулы I
причем А, Х, о, m, R6 и R10 по R17 имеют значения, как определено в п.1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10323701.1 | 2003-05-22 | ||
| DE10323701A DE10323701A1 (de) | 2003-05-22 | 2003-05-22 | Verfahren zur Synthese heterocyclischer Verbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005140090A true RU2005140090A (ru) | 2006-04-20 |
| RU2346936C2 RU2346936C2 (ru) | 2009-02-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005140090/04A RU2346936C2 (ru) | 2003-05-22 | 2004-05-10 | Способ синтеза гетероциклических соединений |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1631552B1 (ru) |
| JP (1) | JP2007502311A (ru) |
| KR (1) | KR20060013676A (ru) |
| CN (1) | CN1795178A (ru) |
| AR (1) | AR044544A1 (ru) |
| AU (1) | AU2004240716A1 (ru) |
| BR (1) | BRPI0410565A (ru) |
| CA (1) | CA2526646A1 (ru) |
| CL (1) | CL2004001156A1 (ru) |
| DE (1) | DE10323701A1 (ru) |
| IL (1) | IL172009A0 (ru) |
| MX (1) | MXPA05012153A (ru) |
| NO (1) | NO20055991L (ru) |
| NZ (1) | NZ543692A (ru) |
| RU (1) | RU2346936C2 (ru) |
| TW (1) | TW200505870A (ru) |
| WO (1) | WO2004103976A2 (ru) |
| ZA (1) | ZA200508430B (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2545903T3 (es) | 2003-06-30 | 2015-09-16 | Sumitomo Chemical Company, Limited | Compuestos de urea asimétricos y procedimiento para producir compuestos asimétricos por reacción de adición asimétrica de conjugado usando dichos compuestos como catalizador |
| JP2010507664A (ja) * | 2006-10-25 | 2010-03-11 | 武田薬品工業株式会社 | ベンズイミダゾール化合物 |
| CA3053196A1 (en) * | 2017-02-24 | 2018-08-30 | Iroa Technologies, Llc | Iroa metabolomics workflow for improved accuracy, identification and quantitation |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2636732A1 (de) * | 1976-08-14 | 1978-02-16 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylamino- imidazoline- (2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben |
| DE10163239A1 (de) | 2001-12-21 | 2003-07-10 | Aventis Pharma Gmbh | Substituierte Imidazolidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie enthaltendes Medikament |
| DE10224892A1 (de) | 2002-06-04 | 2003-12-18 | Aventis Pharma Gmbh | Substituierte Thiophene, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
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2003
- 2003-05-22 DE DE10323701A patent/DE10323701A1/de not_active Withdrawn
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2004
- 2004-05-10 JP JP2006529766A patent/JP2007502311A/ja not_active Abandoned
- 2004-05-10 WO PCT/EP2004/004955 patent/WO2004103976A2/de not_active Ceased
- 2004-05-10 RU RU2005140090/04A patent/RU2346936C2/ru not_active IP Right Cessation
- 2004-05-10 NZ NZ543692A patent/NZ543692A/en unknown
- 2004-05-10 CA CA002526646A patent/CA2526646A1/en not_active Abandoned
- 2004-05-10 BR BRPI0410565-6A patent/BRPI0410565A/pt not_active IP Right Cessation
- 2004-05-10 MX MXPA05012153A patent/MXPA05012153A/es active IP Right Grant
- 2004-05-10 KR KR1020057022334A patent/KR20060013676A/ko not_active Ceased
- 2004-05-10 EP EP04731903.3A patent/EP1631552B1/de not_active Expired - Lifetime
- 2004-05-10 CN CNA2004800141786A patent/CN1795178A/zh active Pending
- 2004-05-10 AU AU2004240716A patent/AU2004240716A1/en not_active Abandoned
- 2004-05-19 CL CL200401156A patent/CL2004001156A1/es unknown
- 2004-05-20 AR ARP040101751A patent/AR044544A1/es not_active Application Discontinuation
- 2004-05-20 TW TW093114184A patent/TW200505870A/zh unknown
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2005
- 2005-10-18 ZA ZA200508430A patent/ZA200508430B/en unknown
- 2005-11-16 IL IL172009A patent/IL172009A0/en unknown
- 2005-12-16 NO NO20055991A patent/NO20055991L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060013676A (ko) | 2006-02-13 |
| ZA200508430B (en) | 2007-12-27 |
| WO2004103976A2 (de) | 2004-12-02 |
| EP1631552A2 (de) | 2006-03-08 |
| CN1795178A (zh) | 2006-06-28 |
| BRPI0410565A (pt) | 2006-06-20 |
| NO20055991L (no) | 2006-02-14 |
| JP2007502311A (ja) | 2007-02-08 |
| AR044544A1 (es) | 2005-09-21 |
| RU2346936C2 (ru) | 2009-02-20 |
| DE10323701A1 (de) | 2004-12-23 |
| CL2004001156A1 (es) | 2005-03-28 |
| CA2526646A1 (en) | 2004-12-02 |
| NZ543692A (en) | 2009-04-30 |
| EP1631552B1 (de) | 2013-07-03 |
| MXPA05012153A (es) | 2006-08-18 |
| TW200505870A (en) | 2005-02-16 |
| IL172009A0 (en) | 2011-08-01 |
| AU2004240716A1 (en) | 2004-12-02 |
| WO2004103976A3 (de) | 2005-02-10 |
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| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20110511 |