IL125358A - History - 5,2 Diphenyl 5H-Thiazole [3, -2a] Pyrimidine-6-alkanone, their preparation and pharmaceutical preparations containing them - Google Patents
History - 5,2 Diphenyl 5H-Thiazole [3, -2a] Pyrimidine-6-alkanone, their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL125358A IL125358A IL12535898A IL12535898A IL125358A IL 125358 A IL125358 A IL 125358A IL 12535898 A IL12535898 A IL 12535898A IL 12535898 A IL12535898 A IL 12535898A IL 125358 A IL125358 A IL 125358A
- Authority
- IL
- Israel
- Prior art keywords
- ethyl
- dichlorophenyl
- signifies
- dimethylamino
- thiazolo
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 4
- MWIPVPMCHOVYNY-UHFFFAOYSA-N 2,5-diphenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine Chemical compound C1(=CC=CC=C1)C1=CN2C(=NC=CC2C2=CC=CC=C2)S1 MWIPVPMCHOVYNY-UHFFFAOYSA-N 0.000 title description 2
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- -1 -N(R13)2 Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 8
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 36
- 239000003814 drug Substances 0.000 claims description 13
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- 238000000034 method Methods 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 7
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- 206010034010 Parkinsonism Diseases 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 5
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- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 208000030507 AIDS Diseases 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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- 206010010904 Convulsion Diseases 0.000 claims description 3
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- HCWRFJOJHNPZPF-UHFFFAOYSA-N 5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid Chemical compound C1C(=CN=C2N1C=CS2)C(=O)O HCWRFJOJHNPZPF-UHFFFAOYSA-N 0.000 claims 1
- 208000029028 brain injury Diseases 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims 1
- 239000003512 metabotropic receptor antagonist Substances 0.000 abstract 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 50
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- 230000015572 biosynthetic process Effects 0.000 description 27
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- 238000002425 crystallisation Methods 0.000 description 25
- 230000008025 crystallization Effects 0.000 description 25
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 22
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- LWFQGLZKTGSAQC-UHFFFAOYSA-N 2-(dimethylamino)ethyl 3-oxobutanoate Chemical compound CN(C)CCOC(=O)CC(C)=O LWFQGLZKTGSAQC-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- 239000002775 capsule Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 7
- SBGGMBXBFORWLM-UHFFFAOYSA-N Cl.Cl.N1=CN=C(C=C1)C(=O)O Chemical compound Cl.Cl.N1=CN=C(C=C1)C(=O)O SBGGMBXBFORWLM-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 229910002027 silica gel Inorganic materials 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- YFYNOWXBIBKGHB-FBCQKBJTSA-N (1s,3r)-1-aminocyclopentane-1,3-dicarboxylic acid Chemical compound OC(=O)[C@]1(N)CC[C@@H](C(O)=O)C1 YFYNOWXBIBKGHB-FBCQKBJTSA-N 0.000 description 2
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 2
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- STZVYGHXFHSRFU-UHFFFAOYSA-N 1-[2-(2,6-dichlorophenyl)-5-(4-methoxyphenyl)-7-methyl-5h-[1,3]thiazolo[3,2-a]pyrimidin-6-yl]ethanone Chemical compound C1=CC(OC)=CC=C1C1C(C(C)=O)=C(C)N=C2SC(C=3C(=CC=CC=3Cl)Cl)=CN21 STZVYGHXFHSRFU-UHFFFAOYSA-N 0.000 description 1
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- CKVXTNVSISIPQR-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-(2,6-dichlorophenyl)-5-(2-methoxyphenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate dihydrobromide Chemical compound Br.Br.COC1=CC=CC=C1C1C(C(=O)OCCN(C)C)=C(C)N=C2SC(C=3C(=CC=CC=3Cl)Cl)=CN21 CKVXTNVSISIPQR-UHFFFAOYSA-N 0.000 description 1
- HEAJUANBUMTMLB-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-(2,6-dichlorophenyl)-5-(3-methoxyphenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC(C2C(=C(C)N=C3SC(=CN32)C=2C(=CC=CC=2Cl)Cl)C(=O)OCCN(C)C)=C1 HEAJUANBUMTMLB-UHFFFAOYSA-N 0.000 description 1
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- WKDUTWRAYQMOMU-UHFFFAOYSA-N 2-(dimethylamino)ethyl 5-(4-chlorophenyl)-2-(2,6-dichlorophenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate dihydrochloride Chemical compound Cl.Cl.CN(C)CCOC(=O)C1=C(C)N=C2SC(C=3C(=CC=CC=3Cl)Cl)=CN2C1C1=CC=C(Cl)C=C1 WKDUTWRAYQMOMU-UHFFFAOYSA-N 0.000 description 1
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- GHRZHMVROFKPDR-UHFFFAOYSA-N 7-benzyl-2-(2,6-dichlorophenyl)-5-(4-methoxyphenyl)-5h-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1C(C(O)=O)=C(CC=2C=CC=CC=2)N=C2SC(C=3C(=CC=CC=3Cl)Cl)=CN21 GHRZHMVROFKPDR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Addiction (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97112324 | 1997-07-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL125358A0 IL125358A0 (en) | 1999-03-12 |
| IL125358A true IL125358A (en) | 2002-09-12 |
Family
ID=8227080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12535898A IL125358A (en) | 1997-07-18 | 1998-07-15 | History - 5,2 Diphenyl 5H-Thiazole [3, -2a] Pyrimidine-6-alkanone, their preparation and pharmaceutical preparations containing them |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US5958931A (cs) |
| EP (1) | EP0891978B1 (cs) |
| JP (1) | JP3100573B2 (cs) |
| KR (1) | KR100296837B1 (cs) |
| CN (1) | CN1102596C (cs) |
| AR (1) | AR016129A1 (cs) |
| AT (1) | ATE214704T1 (cs) |
| AU (1) | AU738207B2 (cs) |
| BR (1) | BR9802482A (cs) |
| CA (1) | CA2243234C (cs) |
| CO (1) | CO5210884A1 (cs) |
| CZ (1) | CZ288944B6 (cs) |
| DE (1) | DE69804273T2 (cs) |
| DK (1) | DK0891978T3 (cs) |
| ES (1) | ES2172840T3 (cs) |
| HR (1) | HRP980398B1 (cs) |
| HU (1) | HUP9801587A3 (cs) |
| ID (1) | ID21824A (cs) |
| IL (1) | IL125358A (cs) |
| MA (1) | MA26520A1 (cs) |
| NO (1) | NO310512B1 (cs) |
| NZ (1) | NZ330988A (cs) |
| PE (1) | PE97499A1 (cs) |
| PL (1) | PL190218B1 (cs) |
| PT (1) | PT891978E (cs) |
| RU (1) | RU2197493C2 (cs) |
| SI (1) | SI0891978T1 (cs) |
| TR (1) | TR199801367A3 (cs) |
| TW (1) | TW523518B (cs) |
| UY (1) | UY25095A1 (cs) |
| YU (1) | YU29798A (cs) |
| ZA (1) | ZA986250B (cs) |
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| EP1074549B1 (en) * | 1999-08-06 | 2003-11-19 | F. Hoffmann-La Roche Ag | Tetrahydro-benzo(d)azepines and their use as antagonists at metabotropic glutamate receptors |
| EA006486B1 (ru) * | 2001-01-31 | 2005-12-29 | Х. Лундбекк А/С | Применение антагонистов рецептора gal3 при лечении депрессии и/или тревоги и соединения, полезные в таких способах |
| EP1408042A4 (en) * | 2001-06-14 | 2005-02-02 | Banyu Pharma Co Ltd | NEW ISOXAZOLOPYRIDONE DERIVATIVES AND THEIR USE |
| US7329662B2 (en) * | 2003-10-03 | 2008-02-12 | Hoffmann-La Roche Inc. | Pyrazolo-pyridine |
| KR100847160B1 (ko) * | 2004-06-21 | 2008-07-17 | 에프. 호프만-라 로슈 아게 | 피라졸로 피리미딘 유도체 |
| SI1761541T1 (sl) * | 2004-06-21 | 2008-06-30 | Hoffmann La Roche | Derivati pirazolo-pirimidina |
| JP4708438B2 (ja) | 2005-02-11 | 2011-06-22 | エフ．ホフマン−ラ ロシュ アーゲー | ｍＧｌｕＲ２アンタゴニストとしてのピラゾロピリミジン誘導体 |
| PL1863818T3 (pl) | 2005-03-23 | 2010-08-31 | Hoffmann La Roche | Pochodne acetylenylo-pirazolo-pirymidyny jako antagoniści MGLUR2 |
| UA90707C2 (en) * | 2005-04-06 | 2010-05-25 | Астразенека Аб | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
| AR053347A1 (es) * | 2005-04-06 | 2007-05-02 | Astrazeneca Ab | Derivados de [1,3]tiazolo[4,5-d]pirimidin-2(3h)-ona 5,7-sustituidos |
| AU2006298829B2 (en) | 2005-09-27 | 2011-03-03 | F. Hoffmann-La Roche Ag | Oxadiazolyl pyrazolo-pyrimidines as mGluR2 antagonists |
| AR059898A1 (es) * | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| TW200845978A (en) * | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| EP2200985B1 (en) | 2007-09-14 | 2011-07-13 | Ortho-McNeil-Janssen Pharmaceuticals, Inc. | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
| ES2409215T3 (es) * | 2007-09-14 | 2013-06-25 | Janssen Pharmaceuticals, Inc. | 4-fenil-1H-piridin-2-onas 1-3-disustituidas |
| US9114138B2 (en) | 2007-09-14 | 2015-08-25 | Janssen Pharmaceuticals, Inc. | 1′,3′-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′] bipyridinyl-2′-ones |
| WO2009062676A2 (en) * | 2007-11-14 | 2009-05-22 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| BRPI0918055A2 (pt) | 2008-09-02 | 2015-12-01 | Addex Pharmaceuticals Sa | derivados de 3-azabiciclo[3,1,0]hexila como moduladores de receptores metabotrópicos de glutamato. |
| ES2466341T3 (es) | 2008-10-16 | 2014-06-10 | Janssen Pharmaceuticals, Inc. | Derivados de indol y benzomorfolina como moduladores de receptores de glutamato metabotrópicos |
| WO2010060589A1 (en) | 2008-11-28 | 2010-06-03 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| CN101503414B (zh) * | 2009-03-04 | 2013-10-30 | 沈阳药科大学 | 噻唑并[3,2-b]-1,2,4-三嗪衍生物及其应用 |
| KR101753826B1 (ko) | 2009-05-12 | 2017-07-04 | 얀센 파마슈티칼즈, 인코포레이티드 | 1,２,４―트리아졸로［４,３―ａ］피리딘 유도체 및 신경정신 질환의 치료 또는 예방을 위한 이들의 용도 |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| SG176018A1 (en) | 2009-05-12 | 2011-12-29 | Janssen Pharmaceuticals Inc | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| AU2011328203B2 (en) | 2010-11-08 | 2015-03-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| WO2012062751A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| CN103298810B (zh) | 2010-11-08 | 2016-03-16 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| CN105612162B (zh) * | 2013-10-11 | 2018-08-21 | 豪夫迈·罗氏有限公司 | 作为nmda受体活性的调节剂的噻唑并嘧啶酮类 |
| PT3096790T (pt) | 2014-01-21 | 2019-10-15 | Janssen Pharmaceutica Nv | Combinações compreendendo moduladores alostéricos positivos ou agonistas ortostéricos do recetor glutamatérgico metabotrópico do subtipo 2 e seu uso |
| SMT202100103T1 (it) | 2014-01-21 | 2021-03-15 | Janssen Pharmaceutica Nv | Combinazione comprendente modulatori allosterici postivi del recettore glutammatergico metabotropico sottotipo 2 e loro utilizzo |
| WO2018177970A1 (en) * | 2017-03-31 | 2018-10-04 | Basf Se | Process for preparing chiral 2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium compounds |
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| US3660418A (en) * | 1970-03-16 | 1972-05-02 | Sandoz Ag | Certain 2 3 5 6-tetrahydroimidazo(2 1-b)thiazoles |
| GB1582744A (en) * | 1976-06-04 | 1981-01-14 | Gruenenthal Gmbh | 7h-thiazolo (and 1,3,4-thiadiazolo-)(3,2-a) pyrimidin-7-one-5-carboxylic acids derivatives and medicaments therof |
| SU1169330A1 (ru) * | 1983-11-10 | 1995-11-27 | Институт Тонкой Органической Химии Им.А.Л.Мнджояна | Способ получения 4-п-алкоксифенил-2,6-диоксогексагидропиримидинов |
| HUT42077A (en) * | 1985-06-03 | 1987-06-29 | Squibb & Sons Inc | Process for producing diesters of 2-tioxo- or 2-oxo-pyrimidine-1,5-dicarboxylic acid and 1-acyl-pyrimidine-5-carboxylic acids and esters |
| ZA905407B (en) * | 1989-06-13 | 1991-04-24 | Daiichi Seiyaku Co | Pyrrolo(2,1-b)thiozle derivatives |
| EP0524055A1 (fr) * | 1991-07-19 | 1993-01-20 | Synthelabo | Dérivés d'imidazo[2,1-b]benzothiazole-3-acétamide, leur préparation et leur application en thérapeutique |
| ZA931109B (en) * | 1992-03-04 | 1993-09-22 | Akzo Nv | Tetrahydropyrimidine derivatives. |
| PL182285B1 (pl) * | 1994-08-12 | 2001-12-31 | Lilly Co Eli | Syntetyczne aminokwasy oraz ich estry i srodki farmaceutyczne je zawierajace PL PL PL PL PL PL PL |
| GB9609976D0 (en) * | 1996-05-13 | 1996-07-17 | Lilly Industries Ltd | Pharmaceutical compounds |
| AU3783497A (en) * | 1996-08-09 | 1998-03-06 | Yamanouchi Pharmaceutical Co., Ltd. | Metabotropic glutamate receptor agonists |
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