NO323841B1 - Kinolon-2(1H)-on derivater, fremgangsmate for deres fremstilling, medisinsk produkt samt farmasoytisk preparat. - Google Patents
Kinolon-2(1H)-on derivater, fremgangsmate for deres fremstilling, medisinsk produkt samt farmasoytisk preparat. Download PDFInfo
- Publication number
- NO323841B1 NO323841B1 NO19981141A NO981141A NO323841B1 NO 323841 B1 NO323841 B1 NO 323841B1 NO 19981141 A NO19981141 A NO 19981141A NO 981141 A NO981141 A NO 981141A NO 323841 B1 NO323841 B1 NO 323841B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- quinolone
- thieno
- ethyl
- piperazinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 229940127554 medical product Drugs 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- -1 4- (thieno [3,2-c] pyridin-4-yl) -piperazin-1-yl group Chemical group 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- RVGRTFBJOXMFAX-UHFFFAOYSA-N 4-piperazin-1-ylthieno[3,2-c]pyridine Chemical compound C1CNCCN1C1=NC=CC2=C1C=CS2 RVGRTFBJOXMFAX-UHFFFAOYSA-N 0.000 claims description 8
- ABERUOJGWHYBJL-UHFFFAOYSA-N (4-fluorophenyl)-piperidin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1CCNCC1 ABERUOJGWHYBJL-UHFFFAOYSA-N 0.000 claims description 5
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- OHOAILOYEDMLGG-UHFFFAOYSA-N 4-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-6-methoxy-1h-quinolin-2-one Chemical compound C12=CC(OC)=CC=C2NC(=O)C=C1CCN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 OHOAILOYEDMLGG-UHFFFAOYSA-N 0.000 claims 1
- XBDOVZHTWHOLLW-UHFFFAOYSA-N 6-chloro-1-methyl-4-[2-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)ethyl]quinolin-2-one Chemical compound C=1C(=O)N(C)C2=CC=C(Cl)C=C2C=1CCN(CC1)CCN1C1=NC=CC2=C1C=CS2 XBDOVZHTWHOLLW-UHFFFAOYSA-N 0.000 claims 1
- TXPOQTMXPOWTJH-UHFFFAOYSA-N 6-chloro-4-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-1-methylquinolin-2-one Chemical compound C=1C(=O)N(C)C2=CC=C(Cl)C=C2C=1CCN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 TXPOQTMXPOWTJH-UHFFFAOYSA-N 0.000 claims 1
- RKJKREPLDPCKKP-UHFFFAOYSA-N 6-fluoro-1-methyl-4-[2-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)ethyl]quinolin-2-one Chemical compound C=1C(=O)N(C)C2=CC=C(F)C=C2C=1CCN(CC1)CCN1C1=NC=CC2=C1C=CS2 RKJKREPLDPCKKP-UHFFFAOYSA-N 0.000 claims 1
- HHIOQLDBIQXLIC-UHFFFAOYSA-N 6-hydroxy-1-methyl-4-[2-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)ethyl]quinolin-2-one Chemical compound C=1C(=O)N(C)C2=CC=C(O)C=C2C=1CCN(CC1)CCN1C1=NC=CC2=C1C=CS2 HHIOQLDBIQXLIC-UHFFFAOYSA-N 0.000 claims 1
- QPKORTUBOTVXPA-UHFFFAOYSA-N 6-methyl-4-[2-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)ethyl]-1h-quinolin-2-one Chemical compound C12=CC(C)=CC=C2NC(=O)C=C1CCN(CC1)CCN1C1=NC=CC2=C1C=CS2 QPKORTUBOTVXPA-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- 239000000203 mixture Substances 0.000 description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
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- 239000000047 product Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
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- 239000000243 solution Substances 0.000 description 20
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- 239000012074 organic phase Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 13
- 235000017557 sodium bicarbonate Nutrition 0.000 description 13
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
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- 238000003756 stirring Methods 0.000 description 12
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- 238000003818 flash chromatography Methods 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 9
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- IWUSEHGANVYEQR-UHFFFAOYSA-N (2,6-dioxo-3h-pyran-4-yl) acetate Chemical compound CC(=O)OC1=CC(=O)OC(=O)C1 IWUSEHGANVYEQR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZBNXJBFROPBBCC-UHFFFAOYSA-N 4-(2-chloroethyl)-6-methoxy-1h-quinolin-2-one Chemical compound N1C(=O)C=C(CCCl)C2=CC(OC)=CC=C21 ZBNXJBFROPBBCC-UHFFFAOYSA-N 0.000 description 3
- UOSXHELVDCMRDP-UHFFFAOYSA-N 4-(2-chloroethyl)-6-nitro-1h-quinolin-2-one Chemical compound N1C(=O)C=C(CCCl)C2=CC([N+](=O)[O-])=CC=C21 UOSXHELVDCMRDP-UHFFFAOYSA-N 0.000 description 3
- FCEKDEBSESGRDL-UHFFFAOYSA-N 4-(2-hydroxyethyl)-1-methyl-2-oxoquinoline-6-carbonitrile Chemical compound C1=C(C#N)C=C2C(CCO)=CC(=O)N(C)C2=C1 FCEKDEBSESGRDL-UHFFFAOYSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
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- NZVXGVBWKLNEDV-UHFFFAOYSA-N 2-(6-cyano-1-methyl-2-oxoquinolin-4-yl)acetic acid Chemical compound C1=C(C#N)C=C2C(CC(O)=O)=CC(=O)N(C)C2=C1 NZVXGVBWKLNEDV-UHFFFAOYSA-N 0.000 description 2
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- ATMXJULQABHEMJ-UHFFFAOYSA-N methyl 2-(6-chloro-1-methyl-2h-quinolin-4-yl)acetate Chemical compound C1=C(Cl)C=C2C(CC(=O)OC)=CCN(C)C2=C1 ATMXJULQABHEMJ-UHFFFAOYSA-N 0.000 description 2
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- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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Landscapes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9510815A FR2738822B1 (fr) | 1995-09-15 | 1995-09-15 | Derives de 4-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)quinolein-2(1h)-one, leur preparation et leur application en therapeutique |
| FR9511083A FR2739100B1 (fr) | 1995-09-21 | 1995-09-21 | Derives de 4-(omega-(4-(4-fluorobenzoyl)piperidin-1-yl)- alkyl)quinolein-2(1h)-one, leur preparation et leur application en therapeutique |
| PCT/FR1996/001401 WO1997010238A1 (fr) | 1995-09-15 | 1996-09-12 | Derives de quinolein-2(1h)-one comme antagonistes de la serotonine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO981141D0 NO981141D0 (no) | 1998-03-13 |
| NO981141L NO981141L (no) | 1998-05-15 |
| NO323841B1 true NO323841B1 (no) | 2007-07-09 |
Family
ID=26232206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19981141A NO323841B1 (no) | 1995-09-15 | 1998-03-13 | Kinolon-2(1H)-on derivater, fremgangsmate for deres fremstilling, medisinsk produkt samt farmasoytisk preparat. |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5958924A (ru) |
| EP (1) | EP0850235B1 (ru) |
| JP (1) | JP3335362B2 (ru) |
| KR (1) | KR100422850B1 (ru) |
| CN (1) | CN1094490C (ru) |
| AR (1) | AR003996A1 (ru) |
| AT (1) | ATE187172T1 (ru) |
| AU (1) | AU715879B2 (ru) |
| BG (1) | BG63779B1 (ru) |
| BR (1) | BR9610579A (ru) |
| CA (1) | CA2228038C (ru) |
| CO (1) | CO4750663A1 (ru) |
| CZ (1) | CZ288149B6 (ru) |
| DE (1) | DE69605430T2 (ru) |
| DK (1) | DK0850235T3 (ru) |
| EE (1) | EE04116B1 (ru) |
| ES (1) | ES2142089T3 (ru) |
| GR (1) | GR3032618T3 (ru) |
| HK (1) | HK1014868A1 (ru) |
| HU (1) | HU222745B1 (ru) |
| IL (1) | IL123600A (ru) |
| NO (1) | NO323841B1 (ru) |
| NZ (1) | NZ318436A (ru) |
| PL (1) | PL184808B1 (ru) |
| RU (1) | RU2167874C2 (ru) |
| SI (1) | SI0850235T1 (ru) |
| SK (1) | SK282222B6 (ru) |
| TR (1) | TR199800464T1 (ru) |
| UA (1) | UA44332C2 (ru) |
| WO (1) | WO1997010238A1 (ru) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR199800464T1 (xx) * | 1995-09-15 | 1998-05-21 | Synthelabo | Serotonin antagonistleri olarak kinolein-2(1H)-on t�revleri |
| FR2761067B1 (fr) * | 1997-03-20 | 1999-04-23 | Synthelabo | Derives de quinolein-2-(1h)-one, leur preparation et leur application en therapeutique |
| FR2761071B1 (fr) * | 1997-03-20 | 1999-12-03 | Synthelabo | Derives de quinolein-2(1h)-one et de dihydroquinolein-2(1h)- one, leur preparation et leur application en therapeutique |
| FR2797874B1 (fr) * | 1999-08-27 | 2002-03-29 | Adir | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CA2398388A1 (en) * | 2000-01-20 | 2001-07-26 | Koji Kato | Novel piperidine compound and pharmaceutical thereof |
| FR2812548B1 (fr) * | 2000-08-01 | 2002-09-20 | Sanofi Synthelabo | Utilisation de derives de quinolein-2(1h)-one ou un de leurs sels pharmaceutiquement acceptable pour la preparation d'un medicament destine au traitement de l'insuffisance renale |
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| TWI320783B (en) | 2005-04-14 | 2010-02-21 | Otsuka Pharma Co Ltd | Heterocyclic compound |
| TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| FR2909670B1 (fr) * | 2006-12-12 | 2010-07-30 | Sanofi Aventis | Derive fluore de quinoleine-2(1h)-one,son procede de preparation et son utilisation comme intermediaire de synthese |
| 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 |
| UA100126C2 (en) | 2007-09-14 | 2012-11-26 | Аддекс Фарма С.А. | 1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h, 1'h-[1, 4'] bipyridinyl-2'-ones |
| PT2200985E (pt) | 2007-09-14 | 2011-07-21 | Ortho Mcneil Janssen Pharm | 4-(aril-x-fenil)-1h-piridin-2-onas 1,3-dissubstituídas |
| AU2009289784B2 (en) | 2008-09-02 | 2012-03-22 | Addex Pharma S.A. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| DK2344471T3 (da) * | 2008-10-02 | 2013-10-07 | Taisho Pharmaceutical Co Ltd | 7-piperidinalkyl-3,4-dihydroquinolon-derivat |
| BRPI0921333A2 (pt) | 2008-11-28 | 2015-12-29 | Addex Pharmaceuticals Sa | derivados de indol e benzoxazina como moduladores de receptores de glutamato metabotrópicos |
| BRPI1010831A2 (pt) | 2009-05-12 | 2016-04-05 | Addex Pharmaceuticals Sa | derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2 |
| 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 |
| EP2649069B1 (en) | 2010-11-08 | 2015-08-26 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| ES2536433T3 (es) | 2010-11-08 | 2015-05-25 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2 |
| 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 |
| 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 |
| HUE045610T2 (hu) | 2014-01-21 | 2020-01-28 | Janssen Pharmaceutica Nv | 2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait vagy ortosztérikus agonistáit tartalmazó kombinációk és alkalmazásuk |
| MX2016009471A (es) | 2014-01-21 | 2016-10-13 | Janssen Pharmaceutica Nv | Combinaciones que comprenden agonistas ortostericos o moduladores alostericos positivos del receptor glutamatergico metabotropico de subtipo 2 y su uso. |
| KR20180114910A (ko) | 2016-02-05 | 2018-10-19 | 데날리 테라퓨틱스 인크. | 수용체-상호작용 단백질 키나제 1의 억제제 |
| WO2018107060A1 (en) | 2016-12-09 | 2018-06-14 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| CN108707109A (zh) * | 2018-08-29 | 2018-10-26 | 常州沃腾化工科技有限公司 | 一种2-甲氧基-4-三氟甲基吡啶-3-磺酰氯的制备方法 |
| US11999750B2 (en) | 2022-01-12 | 2024-06-04 | Denali Therapeutics Inc. | Crystalline forms of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydropyrido [3,2-B][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1278792C (en) * | 1985-05-06 | 1991-01-08 | Joseph P. Yevich | Antipsychotic fused-ring pyridinylpiperazine derivatives |
| KR910006138B1 (ko) * | 1986-09-30 | 1991-08-16 | 에자이 가부시끼가이샤 | 환상아민 유도체 |
| FR2644786B1 (fr) * | 1989-03-21 | 1993-12-31 | Adir Cie | Nouveaux derives fluoro-4 benzoiques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| TR199800464T1 (xx) * | 1995-09-15 | 1998-05-21 | Synthelabo | Serotonin antagonistleri olarak kinolein-2(1H)-on t�revleri |
-
1996
- 1996-09-12 TR TR1998/00464T patent/TR199800464T1/xx unknown
- 1996-09-12 CN CN96198333A patent/CN1094490C/zh not_active Expired - Fee Related
- 1996-09-12 JP JP51170797A patent/JP3335362B2/ja not_active Expired - Fee Related
- 1996-09-12 SI SI9630151T patent/SI0850235T1/xx unknown
- 1996-09-12 DK DK96931112T patent/DK0850235T3/da active
- 1996-09-12 SK SK346-98A patent/SK282222B6/sk not_active IP Right Cessation
- 1996-09-12 ES ES96931112T patent/ES2142089T3/es not_active Expired - Lifetime
- 1996-09-12 KR KR10-1998-0701920A patent/KR100422850B1/ko not_active IP Right Cessation
- 1996-09-12 AR ARP960104322A patent/AR003996A1/es active IP Right Grant
- 1996-09-12 DE DE69605430T patent/DE69605430T2/de not_active Expired - Lifetime
- 1996-09-12 BR BR9610579A patent/BR9610579A/pt not_active Application Discontinuation
- 1996-09-12 CA CA002228038A patent/CA2228038C/en not_active Expired - Fee Related
- 1996-09-12 PL PL96325467A patent/PL184808B1/pl not_active IP Right Cessation
- 1996-09-12 EE EE9800089A patent/EE04116B1/xx not_active IP Right Cessation
- 1996-09-12 AU AU69919/96A patent/AU715879B2/en not_active Ceased
- 1996-09-12 US US09/011,482 patent/US5958924A/en not_active Expired - Lifetime
- 1996-09-12 AT AT96931112T patent/ATE187172T1/de active
- 1996-09-12 EP EP96931112A patent/EP0850235B1/fr not_active Expired - Lifetime
- 1996-09-12 RU RU98106501/04A patent/RU2167874C2/ru not_active IP Right Cessation
- 1996-09-12 HU HU9802940A patent/HU222745B1/hu not_active IP Right Cessation
- 1996-09-12 CZ CZ1998786A patent/CZ288149B6/cs not_active IP Right Cessation
- 1996-09-12 CO CO96048698A patent/CO4750663A1/es unknown
- 1996-09-12 IL IL12360096A patent/IL123600A/en not_active IP Right Cessation
- 1996-09-12 UA UA98031235A patent/UA44332C2/uk unknown
- 1996-09-12 WO PCT/FR1996/001401 patent/WO1997010238A1/fr active IP Right Grant
- 1996-09-12 NZ NZ318436A patent/NZ318436A/xx not_active IP Right Cessation
-
1998
- 1998-03-11 BG BG102316A patent/BG63779B1/bg unknown
- 1998-03-13 NO NO19981141A patent/NO323841B1/no not_active IP Right Cessation
- 1998-12-30 HK HK98119241A patent/HK1014868A1/xx not_active IP Right Cessation
-
2000
- 2000-02-09 GR GR20000400317T patent/GR3032618T3/el unknown
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Legal Events
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| MM1K | Lapsed by not paying the annual fees |