NZ573352A - Substituted carboxamides as group i metabotropic receptor antagonists - Google Patents
Substituted carboxamides as group i metabotropic receptor antagonistsInfo
- Publication number
- NZ573352A NZ573352A NZ573352A NZ57335207A NZ573352A NZ 573352 A NZ573352 A NZ 573352A NZ 573352 A NZ573352 A NZ 573352A NZ 57335207 A NZ57335207 A NZ 57335207A NZ 573352 A NZ573352 A NZ 573352A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- formula
- phenyl
- mmol
- preparation
- Prior art date
Links
- 150000003857 carboxamides Chemical class 0.000 title description 8
- 239000003512 metabotropic receptor antagonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 208000002193 Pain Diseases 0.000 claims abstract description 45
- 230000036407 pain Effects 0.000 claims abstract description 35
- -1 carboxamide compound Chemical class 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 239000003814 drug Substances 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000001246 bromo group Chemical group Br* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 8
- 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
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- LXZFJIRPRVGCDF-PRHODGIISA-N (1r,2r)-n-[3-(4-chlorophenyl)-4-methyl-1,2-thiazol-5-yl]-2-methylcyclopropane-1-carboxamide Chemical compound C[C@@H]1C[C@H]1C(=O)NC1=C(C)C(C=2C=CC(Cl)=CC=2)=NS1 LXZFJIRPRVGCDF-PRHODGIISA-N 0.000 claims description 2
- LRVAFLGRKGZXGK-HTRCEHHLSA-N (1r,2r)-n-[4-bromo-3-(3,4-dichlorophenyl)-1,2-thiazol-5-yl]-2-methylcyclopropane-1-carboxamide Chemical compound C[C@@H]1C[C@H]1C(=O)NC1=C(Br)C(C=2C=C(Cl)C(Cl)=CC=2)=NS1 LRVAFLGRKGZXGK-HTRCEHHLSA-N 0.000 claims description 2
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 2
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 165
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
- 238000002360 preparation method Methods 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 46
- 239000000203 mixture Substances 0.000 description 39
- 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 38
- 238000003756 stirring Methods 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- 239000002253 acid Substances 0.000 description 25
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 18
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 18
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- 229910000027 potassium carbonate Inorganic materials 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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- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
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- 229910002027 silica gel Inorganic materials 0.000 description 14
- 230000001684 chronic effect Effects 0.000 description 13
- 235000015320 potassium carbonate Nutrition 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 11
- 208000000094 Chronic Pain Diseases 0.000 description 10
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 10
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 10
- 230000002757 inflammatory effect Effects 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- AYEGPMGNMOIHDL-QWWZWVQMSA-N (1r,2r)-2-methylcyclopropane-1-carboxylic acid Chemical compound C[C@@H]1C[C@H]1C(O)=O AYEGPMGNMOIHDL-QWWZWVQMSA-N 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
- AYEGPMGNMOIHDL-UHFFFAOYSA-N 2-methylcyclopropane-1-carboxylic acid Chemical compound CC1CC1C(O)=O AYEGPMGNMOIHDL-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
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- 230000000694 effects Effects 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
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- 239000000725 suspension Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- VCSKFTJGUYAXOC-CHDUMGHJSA-N (2s)-2-amino-3-phenylpropan-1-ol;(1r,2r)-2-methylcyclopropane-1-carboxylic acid Chemical compound C[C@@H]1C[C@H]1C(O)=O.OC[C@@H](N)CC1=CC=CC=C1 VCSKFTJGUYAXOC-CHDUMGHJSA-N 0.000 description 7
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- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-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
- 239000010410 layer Substances 0.000 description 7
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- 230000004044 response Effects 0.000 description 7
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- UEGDTXGDZZESGT-MWLCHTKSSA-N benzyl (1r,2r)-2-methylcyclopropane-1-carboxylate Chemical compound C[C@@H]1C[C@H]1C(=O)OCC1=CC=CC=C1 UEGDTXGDZZESGT-MWLCHTKSSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
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- 238000001514 detection method Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 125000002346 iodo group Chemical group I* 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (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 (1)
| Publication Number | Publication Date |
|---|---|
| NZ573352A true NZ573352A (en) | 2011-10-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ573352A NZ573352A (en) | 2006-06-08 | 2007-06-07 | Substituted carboxamides as group i metabotropic receptor antagonists |
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| Country | Link |
|---|---|
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| 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 |
| AR070986A1 (es) | 2008-04-04 | 2010-05-19 | Lilly Co Eli | Compuesto de 3-indazoil-4 -piridilisotiazoles, composicion farmaceutica que lo comprende y su uso para la manufactura de un medicamento util para tratar la ansiedad |
| WO2010146338A1 (en) * | 2009-06-15 | 2010-12-23 | The University Of Edinburgh | Amido-isothiazole compounds and their use as inhibitors of 11beta-hsd1 for the treatment of metabolic syndrome and related disorders |
| DK2477983T3 (en) | 2009-09-16 | 2015-06-29 | Univ Edinburgh | (4-phenyl-piperidin-1-yl) - [5-1H-pyrazol-4-yl) -thiophene-3-yl] -METHANONFORBINDELSER AND THEIR USE |
| BR112012027640B1 (pt) | 2010-04-29 | 2021-08-03 | The University Of Edinburgh | Composto, composição farmacêutica, e, métodos de preparar uma composição farmacêutica, de inibir a função da 11beta-hidroxiesteroide desidrogenase do tipo 1 |
| KR102160841B1 (ko) | 2012-11-13 | 2020-09-28 | 닛산 가가쿠 가부시키가이샤 | 2-피리돈 화합물 |
| SG11201902588PA (en) | 2016-09-23 | 2019-05-30 | Bayer Ag | N3-Cyclically Substituted Thienouracils 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 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL72091A0 (en) * | 1983-06-20 | 1984-10-31 | Lilly Co Eli | N'-substituted(3-aryl 5-isothiazolyl)urea derivatives |
| DE4328425A1 (de) | 1993-08-24 | 1995-03-02 | Basf Ag | Acylamino-substituierte Isoxazol- bzw. Isothiazolderivate, Verfahren zu deren Herstellung und ihre Verwendung |
| DK124393D0 (da) * | 1993-11-03 | 1993-11-03 | Lundbeck & Co As H | Compounds |
| DE19542372A1 (de) * | 1995-11-14 | 1997-05-15 | Bayer Ag | Acylierte 5-Aminoisothiazole |
| UA60365C2 (uk) * | 1998-06-04 | 2003-10-15 | Пфайзер Продактс Інк. | Похідні ізотіазолу, спосіб їх одержання, фармацевтична композиція та спосіб лікування гіперпроліферативного захворювання у ссавця |
| JP3411262B2 (ja) * | 1999-08-20 | 2003-05-26 | 萬有製薬株式会社 | 新規スピロ化合物 |
| NZ530782A (en) * | 2001-08-06 | 2005-11-25 | Pharmacia Italia S | Aminoisoxazole derivatives active as kinase inhibitors |
| US20060281803A1 (en) * | 2003-09-23 | 2006-12-14 | Lindsley Craig W | Pyrazole modulators of metabotropic glutamate receptors |
| CN1984899B (zh) * | 2004-05-12 | 2011-07-27 | 先灵公司 | Cxcr1和cxcr2趋化因子拮抗剂 |
| WO2006033005A2 (en) * | 2004-09-23 | 2006-03-30 | Pfizer Products Inc. | Thrombopoietin receptor agonists |
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2007
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- 2007-06-07 PT PT07873705T patent/PT2076502E/pt unknown
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- 2007-06-07 AT AT07873705T patent/ATE509921T1/de active
- 2007-06-07 MY MYPI20084973A patent/MY148084A/en unknown
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- 2007-06-07 SI SI200730695T patent/SI2076502T1/sl unknown
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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
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- 2008-12-05 TN TNP2008000506A patent/TNSN08506A1/en unknown
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2009
- 2009-01-06 MA MA31553A patent/MA30620B1/fr unknown
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2011
- 2011-06-24 CY CY20111100600T patent/CY1111588T1/el unknown
Also Published As
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