EA014233B1 - Замещенные карбоксамиды - Google Patents
Замещенные карбоксамиды Download PDFInfo
- Publication number
- EA014233B1 EA014233B1 EA200870516A EA200870516A EA014233B1 EA 014233 B1 EA014233 B1 EA 014233B1 EA 200870516 A EA200870516 A EA 200870516A EA 200870516 A EA200870516 A EA 200870516A EA 014233 B1 EA014233 B1 EA 014233B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- compound
- mmol
- synthesis
- mixture
- Prior art date
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- 150000003857 carboxamides Chemical class 0.000 title description 4
- -1 carboxamide compound Chemical class 0.000 claims abstract description 61
- 208000002193 Pain Diseases 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 230000036407 pain Effects 0.000 claims abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 140
- 150000001875 compounds Chemical class 0.000 claims description 91
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 2
- ATQVBSVAXDRWFW-HBMCJLEFSA-N [(1r)-2-(4-hydroxyphenyl)-1-[[(2s)-1-[[(2s)-3-methyl-2-(methylamino)butanoyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]ethyl]phosphonic acid Chemical compound C([C@@H](C(=O)NC(=O)[C@H](C(C)C)NC)N[C@@H](CC=1C=CC(O)=CC=1)P(O)(O)=O)C1=CC=CC=C1 ATQVBSVAXDRWFW-HBMCJLEFSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 230000008520 organization Effects 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 94
- 230000015572 biosynthetic process Effects 0.000 description 78
- 238000003786 synthesis reaction Methods 0.000 description 77
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
- 239000000203 mixture Substances 0.000 description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 44
- 238000000034 method Methods 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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- 102000005962 receptors Human genes 0.000 description 19
- 108020003175 receptors Proteins 0.000 description 19
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 16
- 229910052794 bromium Inorganic materials 0.000 description 16
- 239000003480 eluent Substances 0.000 description 16
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 15
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 239000012267 brine Substances 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 230000001684 chronic effect Effects 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 102100040396 Transcobalamin-1 Human genes 0.000 description 12
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- 239000012071 phase Substances 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 11
- 230000008025 crystallization Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- STVVMTBJNDTZBF-UHFFFAOYSA-N -2-Amino-3-phenyl-1-propanol Natural products OCC(N)CC1=CC=CC=C1 STVVMTBJNDTZBF-UHFFFAOYSA-N 0.000 description 9
- AYEGPMGNMOIHDL-UHFFFAOYSA-N 2-methylcyclopropane-1-carboxylic acid Chemical compound CC1CC1C(O)=O AYEGPMGNMOIHDL-UHFFFAOYSA-N 0.000 description 9
- 208000000094 Chronic Pain Diseases 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 208000004296 neuralgia Diseases 0.000 description 9
- 208000021722 neuropathic pain Diseases 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 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 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
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- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 238000010521 absorption reaction Methods 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 6
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- 230000002757 inflammatory effect Effects 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- MBRXSOUHUFBPQC-RFPWEZLHSA-N (6s,8s,9r,10s,11s,13s,14s,16r,17s)-9-chloro-6,11-difluoro-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,11,12,14,15,16,17-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(Cl)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1F MBRXSOUHUFBPQC-RFPWEZLHSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000006478 transmetalation reaction Methods 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
-
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81183906P | 2006-06-08 | 2006-06-08 | |
| PCT/US2007/070572 WO2008103185A2 (en) | 2006-06-08 | 2007-06-07 | Substituted carboxamides as group i metabotropic receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200870516A1 EA200870516A1 (ru) | 2009-06-30 |
| EA014233B1 true EA014233B1 (ru) | 2010-10-29 |
Family
ID=39673278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200870516A EA014233B1 (ru) | 2006-06-08 | 2007-06-07 | Замещенные карбоксамиды |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US7960419B2 (enExample) |
| EP (1) | EP2076502B1 (enExample) |
| JP (1) | JP5108878B2 (enExample) |
| KR (1) | KR101051559B1 (enExample) |
| CN (1) | CN101466691B (enExample) |
| AT (1) | ATE509921T1 (enExample) |
| AU (1) | AU2007347428B2 (enExample) |
| BR (1) | BRPI0712862A2 (enExample) |
| CA (1) | CA2652074C (enExample) |
| CR (1) | CR10410A (enExample) |
| CY (1) | CY1111588T1 (enExample) |
| DK (1) | DK2076502T3 (enExample) |
| EA (1) | EA014233B1 (enExample) |
| EC (1) | ECSP088939A (enExample) |
| ES (1) | ES2362949T3 (enExample) |
| HR (1) | HRP20110436T1 (enExample) |
| IL (1) | IL195632A (enExample) |
| MA (1) | MA30620B1 (enExample) |
| MX (1) | MX2008015485A (enExample) |
| MY (1) | MY148084A (enExample) |
| NO (1) | NO341474B1 (enExample) |
| NZ (1) | NZ573352A (enExample) |
| PL (1) | PL2076502T3 (enExample) |
| PT (1) | PT2076502E (enExample) |
| RS (1) | RS51818B (enExample) |
| SI (1) | SI2076502T1 (enExample) |
| TN (1) | TNSN08506A1 (enExample) |
| UA (1) | UA95480C2 (enExample) |
| WO (1) | WO2008103185A2 (enExample) |
| ZA (1) | ZA200809111B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0804685D0 (en) | 2008-03-13 | 2008-04-16 | Univ Edinburgh | Therapeutic compounds and their use |
| MX2010010781A (es) | 2008-04-04 | 2010-12-14 | Lilly Co Eli | 3-indazolil-4-piridilisotiazoles. |
| EP2443113A1 (en) * | 2009-06-15 | 2012-04-25 | The University Of Edinburgh | Amido-isothiazole compounds and their use as inhibitors of 11beta-hsd1 for the treatment of metabolic syndrome and related disorders |
| JP5779181B2 (ja) | 2009-09-16 | 2015-09-16 | ザ ユニバーシティ オブ エディンバラ | （４−フェニル−ピペリジン−１−イル）−［５−（１ｈ−ピラゾール−４−イル）−チオフェン−３−イル］−メタノン化合物及びそれらの使用 |
| EP2563780B1 (en) | 2010-04-29 | 2015-05-06 | The University Of Edinburgh | 3,3-disubstituted-(8-aza-bicyclo[3.2.1]oct-8-yl)-[5-(1h-pyrazol-4-yl)-thiophen-3-yl]-methanones as inhibitors of 11(beta)-hsd1 |
| DK2921489T3 (en) | 2012-11-13 | 2017-10-16 | Nissan Chemical Ind Ltd | 2-pyridone-RELATED |
| AU2017329677A1 (en) | 2016-09-23 | 2019-04-18 | Bayer Aktiengesellschaft | N 3 -cyclically substituted thienouraciles and use thereof |
| CN117567266B (zh) * | 2023-11-07 | 2024-06-14 | 康龙化成手性医药技术(宁波)有限公司 | 一种制备2-甲基环丙羧酸的方法 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0129407A2 (en) * | 1983-06-20 | 1984-12-27 | Eli Lilly And Company | Improvements in and relating to (3-aryl-5-isothiazolyl)ureas |
| EP0640597A1 (de) * | 1993-08-24 | 1995-03-01 | BASF Aktiengesellschaft | Acylamino-substituierte Isoxazol- bzw. Isothiazolderivate, Verfahren zu deren Herstellung und ihre Verwendung |
| WO1995012587A1 (en) * | 1993-11-03 | 1995-05-11 | H. Lundbeck A/S | 5-arylisoxazol-4-yl-substituted 2-amino carboxylic acid compounds |
| RU2001135711A (ru) * | 1999-05-28 | 2003-09-10 | Нихон Байер Агрохем К.К. | Изотиазолкарбоксамиды и их применение в качестве бактерицидных средств |
| EA004935B1 (ru) * | 1998-06-04 | 2004-10-28 | Пфайзер Продактс Инк. | Производные изотиазола, применимые в качестве противораковых агентов |
| WO2005113534A2 (en) * | 2004-05-12 | 2005-12-01 | Schering Corporation | Cxcr1 and cxcr2 chemokine antagonists |
| WO2006033005A2 (en) * | 2004-09-23 | 2006-03-30 | Pfizer Products Inc. | Thrombopoietin receptor agonists |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19542372A1 (de) * | 1995-11-14 | 1997-05-15 | Bayer Ag | Acylierte 5-Aminoisothiazole |
| JP3411262B2 (ja) * | 1999-08-20 | 2003-05-26 | 萬有製薬株式会社 | 新規スピロ化合物 |
| JP2005501073A (ja) * | 2001-08-06 | 2005-01-13 | フアルマシア・イタリア・エツセ・ピー・アー | キナーゼ阻害薬活性を有するアミノイソオキサゾール誘導体 |
| EP1667983A4 (en) * | 2003-09-23 | 2010-07-21 | Merck Sharp & Dohme | PYRAZOL MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS |
-
2007
- 2007-06-07 PL PL07873705T patent/PL2076502T3/pl unknown
- 2007-06-07 SI SI200730695T patent/SI2076502T1/sl unknown
- 2007-06-07 DK DK07873705.3T patent/DK2076502T3/da active
- 2007-06-07 NZ NZ573352A patent/NZ573352A/en not_active IP Right Cessation
- 2007-06-07 EP EP07873705A patent/EP2076502B1/en active Active
- 2007-06-07 HR HR20110436T patent/HRP20110436T1/hr unknown
- 2007-06-07 KR KR1020087029772A patent/KR101051559B1/ko not_active Expired - Fee Related
- 2007-06-07 MX MX2008015485A patent/MX2008015485A/es active IP Right Grant
- 2007-06-07 JP JP2009514523A patent/JP5108878B2/ja not_active Expired - Fee Related
- 2007-06-07 ES ES07873705T patent/ES2362949T3/es active Active
- 2007-06-07 UA UAA200813907A patent/UA95480C2/uk unknown
- 2007-06-07 AU AU2007347428A patent/AU2007347428B2/en not_active Ceased
- 2007-06-07 RS RS20110336A patent/RS51818B/sr unknown
- 2007-06-07 US US12/300,415 patent/US7960419B2/en active Active
- 2007-06-07 PT PT07873705T patent/PT2076502E/pt unknown
- 2007-06-07 CA CA2652074A patent/CA2652074C/en not_active Expired - Fee Related
- 2007-06-07 AT AT07873705T patent/ATE509921T1/de active
- 2007-06-07 EA EA200870516A patent/EA014233B1/ru not_active IP Right Cessation
- 2007-06-07 CN CN2007800211890A patent/CN101466691B/zh not_active Expired - Fee Related
- 2007-06-07 BR BRPI0712862-2A patent/BRPI0712862A2/pt not_active IP Right Cessation
- 2007-06-07 WO PCT/US2007/070572 patent/WO2008103185A2/en not_active Ceased
- 2007-06-07 MY MYPI20084973A patent/MY148084A/en unknown
- 2007-10-29 CR CR10410A patent/CR10410A/es unknown
-
2008
- 2008-10-23 ZA ZA200809111A patent/ZA200809111B/xx unknown
- 2008-12-01 IL IL195632A patent/IL195632A/en not_active IP Right Cessation
- 2008-12-02 NO NO20085028A patent/NO341474B1/no not_active IP Right Cessation
- 2008-12-03 EC EC2008008939A patent/ECSP088939A/es unknown
- 2008-12-05 TN TNP2008000506A patent/TNSN08506A1/en unknown
-
2009
- 2009-01-06 MA MA31553A patent/MA30620B1/fr unknown
-
2011
- 2011-06-24 CY CY20111100600T patent/CY1111588T1/el unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0129407A2 (en) * | 1983-06-20 | 1984-12-27 | Eli Lilly And Company | Improvements in and relating to (3-aryl-5-isothiazolyl)ureas |
| EP0640597A1 (de) * | 1993-08-24 | 1995-03-01 | BASF Aktiengesellschaft | Acylamino-substituierte Isoxazol- bzw. Isothiazolderivate, Verfahren zu deren Herstellung und ihre Verwendung |
| WO1995012587A1 (en) * | 1993-11-03 | 1995-05-11 | H. Lundbeck A/S | 5-arylisoxazol-4-yl-substituted 2-amino carboxylic acid compounds |
| EA004935B1 (ru) * | 1998-06-04 | 2004-10-28 | Пфайзер Продактс Инк. | Производные изотиазола, применимые в качестве противораковых агентов |
| RU2001135711A (ru) * | 1999-05-28 | 2003-09-10 | Нихон Байер Агрохем К.К. | Изотиазолкарбоксамиды и их применение в качестве бактерицидных средств |
| WO2005113534A2 (en) * | 2004-05-12 | 2005-12-01 | Schering Corporation | Cxcr1 and cxcr2 chemokine antagonists |
| WO2006033005A2 (en) * | 2004-09-23 | 2006-03-30 | Pfizer Products Inc. | Thrombopoietin receptor agonists |
Non-Patent Citations (2)
| Title |
|---|
| J. GOERDELER, H.W. POHLAND: "5-Amino-isothiazole", ANGEW. CHEM., vol. 72, no. 2, 1960, pages 77-77, XP002492022, tab. 1 * |
| J. GOERDELER, H.W. POHLAND: "Darstellung und Oxidation einiger beta-Amino-thiocrotonamide", CHEMISCHE BERICHTE, vol. 94, 1961, pages 2950-2959, XP002492021, page 2957 * |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): RU |