NO300135B1 - Heterocyklisk substituerte 2-acylamino-5-tiazoler, og mellomprodukter for fremstilling derav - Google Patents

Heterocyklisk substituerte 2-acylamino-5-tiazoler, og mellomprodukter for fremstilling derav Download PDF

Info

Publication number: NO300135B1
Authority: NO; Norway
Prior art keywords: group; alkyl; constitutes; formula; phenyl
Prior art date: 1991-06-05

Application number

NO922215A

Other languages

English (en)

Norwegian (no)

Other versions

NO922215D0 (no

NO922215L (no

Inventor

Robert Boigegrain

Roger Brodin

Danielle Gully

Jean-Charles Molimard

Dominique Olliero

Original Assignee

Sanofi Elf

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.)

1991-06-05

Filing date

1992-06-04

Publication date

1997-04-14

1992-06-04 Application filed by Sanofi Elf filed Critical Sanofi Elf

1992-06-04 Publication of NO922215D0 publication Critical patent/NO922215D0/no

1992-12-07 Publication of NO922215L publication Critical patent/NO922215L/no

1997-04-14 Publication of NO300135B1 publication Critical patent/NO300135B1/no

Links

125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title description 13
239000000543 intermediate Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 54
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 6
125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 3
-1 phenyl carbon Chemical compound 0.000 claims description 21
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims 1
125000003118 aryl group Chemical group 0.000 abstract description 4
150000001412 amines Chemical class 0.000 abstract description 3
125000004103 aminoalkyl group Chemical group 0.000 abstract description 2
125000005842 heteroatom Chemical group 0.000 abstract 2
229910052760 oxygen Inorganic materials 0.000 abstract 2
229910052717 sulfur Inorganic materials 0.000 abstract 2
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000005242 carbamoyl alkyl group Chemical group 0.000 abstract 1
125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
125000003884 phenylalkyl group Chemical group 0.000 abstract 1
KGFYHTZWPPHNLQ-AWEZNQCLSA-N rivaroxaban Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 KGFYHTZWPPHNLQ-AWEZNQCLSA-N 0.000 abstract 1
125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 86
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
239000000203 mixture Substances 0.000 description 35
239000000243 solution Substances 0.000 description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
239000012074 organic phase Substances 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
238000000034 method Methods 0.000 description 24
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 21
IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 19
239000002253 acid Substances 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
229940107137 cholecystokinin Drugs 0.000 description 16
101800001982 Cholecystokinin Proteins 0.000 description 15
102100025841 Cholecystokinin Human genes 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 14
239000011734 sodium Substances 0.000 description 13
HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
239000002585 base Substances 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000000047 product Substances 0.000 description 10
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 description 9
239000003480 eluent Substances 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
KXHBYSRUWPZBMF-UHFFFAOYSA-N 1-acetylindole-2-carboxylic acid Chemical compound C1=CC=C2N(C(=O)C)C(C(O)=O)=CC2=C1 KXHBYSRUWPZBMF-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
239000005557 antagonist Substances 0.000 description 8
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108010052343 Gastrins Proteins 0.000 description 7
239000007853 buffer solution Substances 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
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TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 6
102000005962 receptors Human genes 0.000 description 6
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238000010992 reflux Methods 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000010908 decantation Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
108010089335 Cholecystokinin A Receptor Proteins 0.000 description 4
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102100034927 Cholecystokinin receptor type A Human genes 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
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210000003169 central nervous system Anatomy 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
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SYYLBTHATZNOSE-UHFFFAOYSA-N 1-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]indole-2-carboxylic acid Chemical compound C1=CC=C2N(CC(=O)OC(C)(C)C)C(C(O)=O)=CC2=C1 SYYLBTHATZNOSE-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
YUMHQQUMURQNOP-UHFFFAOYSA-N 5-benzyl-4-(2,4-dimethoxyphenyl)-1,3-thiazol-2-amine Chemical compound COC1=CC(OC)=CC=C1C1=C(CC=2C=CC=CC=2)SC(N)=N1 YUMHQQUMURQNOP-UHFFFAOYSA-N 0.000 description 3
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238000005727 Friedel-Crafts reaction Methods 0.000 description 3
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WOAKYNXITKJPIU-UHFFFAOYSA-N 1-(2-amino-4-phenyl-1,3-thiazol-5-yl)ethyl adamantane-1-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)OC(C)C=1SC(N)=NC=1C1=CC=CC=C1 WOAKYNXITKJPIU-UHFFFAOYSA-N 0.000 description 2
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
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MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005309 thioalkoxy group Chemical group 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1

Classifications

- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon 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
- C07D277/08—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- 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
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P35/00—Antineoplastic agents
- 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
- 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
- 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
- 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
- C07D417/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Epidemiology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO922215A 1991-06-05 1992-06-04 Heterocyklisk substituerte 2-acylamino-5-tiazoler, og mellomprodukter for fremstilling derav NO300135B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9106814A FR2677356B1 (fr)	1991-06-05	1991-06-05	Derives heterocycliques d'acylamino-2 thiazoles-5 substitues, leur preparation et compositions pharmaceutiques en contenant.

Publications (3)

Publication Number	Publication Date
NO922215D0 NO922215D0 (no)	1992-06-04
NO922215L NO922215L (no)	1992-12-07
NO300135B1 true NO300135B1 (no)	1997-04-14

Family

ID=9413505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO922215A NO300135B1 (no)	1991-06-05	1992-06-04	Heterocyklisk substituerte 2-acylamino-5-tiazoler, og mellomprodukter for fremstilling derav

Country Status (23)

Country	Link
US (2)	US5314889A (xx)
EP (1)	EP0518731B1 (xx)
JP (1)	JP3199451B2 (xx)
KR (1)	KR100222309B1 (xx)
AT (1)	ATE170186T1 (xx)
AU (1)	AU650754B2 (xx)
BR (2)	BR9202156A (xx)
CA (1)	CA2070526A1 (xx)
CZ (1)	CZ289003B6 (xx)
DE (1)	DE69226729T2 (xx)
ES (1)	ES2121575T3 (xx)
FI (1)	FI922589A7 (xx)
FR (1)	FR2677356B1 (xx)
HU (1)	HU221312B1 (xx)
IE (1)	IE921814A1 (xx)
IL (1)	IL102004A (xx)
MX (1)	MX9202662A (xx)
NO (1)	NO300135B1 (xx)
NZ (1)	NZ243009A (xx)
RU (1)	RU2059637C1 (xx)
TW (1)	TW202448B (xx)
UA (1)	UA26899C2 (xx)
ZA (1)	ZA923981B (xx)

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JP2008509923A (ja) *	2004-08-13	2008-04-03	ジェネンテック・インコーポレーテッド	Ａｔｐ利用酵素のチアゾールベースのインヒビター
FR2876692B1 (fr) *	2004-10-19	2007-02-23	Sanofi Aventis Sa	Derives de 2-amido-4-phenylthiazole, leur preparation et leur application en therapeutique
JP4774995B2 (ja) *	2005-01-12	2011-09-21	アステラス製薬株式会社	アシルアミノチアゾール誘導体を有効成分とする医薬組成物
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US20100280023A1 (en) *	2005-06-23	2010-11-04	Kyowa Hakko Kogyo Co., Ltd.	Thiazole derivatives
HUE034666T2 (hu)	2005-08-02	2018-02-28	Kyowa Hakko Kirin Co Ltd	Szer alvászavar kezelésére és/vagy megelõzésére
US20070203153A1 (en) *	2005-11-08	2007-08-30	Astellas Pharma Inc.	Compositions and methods for treating thrombocytopenia
FR2895989B1 (fr) *	2006-01-06	2010-04-30	Sanofi Aventis	Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique
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TWI443102B (zh)	2008-03-31	2014-07-01	Genentech Inc	苯并哌喃及苯并氧呯ｐｉ３ｋ抑制劑化合物及其使用方法
US20110166112A1 (en) *	2009-08-14	2011-07-07	Eisai, Inc.	Method for stimulating platelet production
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1991
- 1991-06-05 FR FR9106814A patent/FR2677356B1/fr not_active Expired - Fee Related
1992
- 1992-05-26 IL IL102004A patent/IL102004A/xx not_active IP Right Cessation
- 1992-05-28 AU AU17279/92A patent/AU650754B2/en not_active Ceased
- 1992-05-29 US US07/889,910 patent/US5314889A/en not_active Expired - Fee Related
- 1992-06-01 TW TW081104270A patent/TW202448B/zh active
- 1992-06-01 ZA ZA923981A patent/ZA923981B/xx unknown
- 1992-06-03 NZ NZ243009A patent/NZ243009A/en unknown
- 1992-06-03 EP EP92401518A patent/EP0518731B1/fr not_active Expired - Lifetime
- 1992-06-03 AT AT92401518T patent/ATE170186T1/de not_active IP Right Cessation
- 1992-06-03 ES ES92401518T patent/ES2121575T3/es not_active Expired - Lifetime
- 1992-06-03 DE DE69226729T patent/DE69226729T2/de not_active Expired - Fee Related
- 1992-06-04 CA CA002070526A patent/CA2070526A1/en not_active Abandoned
- 1992-06-04 FI FI922589A patent/FI922589A7/fi not_active Application Discontinuation
- 1992-06-04 HU HU9201870A patent/HU221312B1/hu not_active IP Right Cessation
- 1992-06-04 JP JP14415092A patent/JP3199451B2/ja not_active Expired - Fee Related
- 1992-06-04 NO NO922215A patent/NO300135B1/no not_active IP Right Cessation
- 1992-06-04 CZ CS19921693A patent/CZ289003B6/cs not_active IP Right Cessation
- 1992-06-04 RU SU5011874/04A patent/RU2059637C1/ru not_active IP Right Cessation
- 1992-06-04 MX MX9202662A patent/MX9202662A/es not_active IP Right Cessation
- 1992-06-05 BR BR929202156A patent/BR9202156A/pt not_active Application Discontinuation
- 1992-06-05 KR KR1019920009859A patent/KR100222309B1/ko not_active Expired - Fee Related
- 1992-07-01 IE IE181492A patent/IE921814A1/en not_active IP Right Cessation
1993
- 1993-06-15 UA UA93002939A patent/UA26899C2/uk unknown
1994
- 1994-03-03 US US08/205,408 patent/US5380736A/en not_active Expired - Fee Related
1997
- 1997-05-12 BR BR1100786-9A patent/BR1100786A/pt active IP Right Grant

Also Published As

Publication number	Publication date
FR2677356A1 (fr)	1992-12-11
UA26899C2 (uk)	1999-12-29
ES2121575T3 (es)	1998-12-01
AU650754B2 (en)	1994-06-30
IL102004A0 (en)	1992-12-30
NZ243009A (en)	1995-05-26
DE69226729T2 (de)	1999-05-06
CS169392A3 (en)	1992-12-16
HK1012397A1 (en)	1999-07-30
BR9202156A (pt)	1993-02-02
EP0518731B1 (fr)	1998-08-26
CZ289003B6 (cs)	2001-10-17
NO922215D0 (no)	1992-06-04
EP0518731A1 (fr)	1992-12-16
FR2677356B1 (fr)	1995-03-17
FI922589A0 (fi)	1992-06-04
IL102004A (en)	1997-04-15
AU1727992A (en)	1992-12-10
JP3199451B2 (ja)	2001-08-20
US5380736A (en)	1995-01-10
IE921814A1 (en)	1992-12-16
NO922215L (no)	1992-12-07
BR1100786A (pt)	2000-03-14
US5314889A (en)	1994-05-24
HU221312B1 (en)	2002-09-28
RU2059637C1 (ru)	1996-05-10
KR100222309B1 (ko)	1999-10-01
JPH05155871A (ja)	1993-06-22
TW202448B (xx)	1993-03-21
KR930000492A (ko)	1993-01-15
MX9202662A (es)	1992-12-31
FI922589A7 (fi)	1992-12-06
HUT75870A (en)	1997-05-28
ZA923981B (en)	1993-12-01
ATE170186T1 (de)	1998-09-15
CA2070526A1 (en)	1992-12-06
DE69226729D1 (de)	1998-10-01
HU9201870D0 (en)	1992-08-28

Publication	Publication Date	Title
NO300135B1 (no)	1997-04-14	Heterocyklisk substituerte 2-acylamino-5-tiazoler, og mellomprodukter for fremstilling derav
KR0147281B1 (ko)	1998-08-17	헤테로사이클릭 치환된 아실아미노티아졸 그 제조방법 및 그 화합물을 포함하는 약학적 조성물
US6380230B1 (en)	2002-04-30	Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them
AU644054B2 (en)	1993-12-02	Benzoisothiazole and benzoisoxazole-3-carboxamides
NO310619B1 (no)	2001-07-30	Acetamidderivater og farmasöytisk preparat inneholdende disse
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