CN100418968C - 吡嗪并(氮杂)吲哚衍生物 - Google Patents
吡嗪并(氮杂)吲哚衍生物 Download PDFInfo
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- CN100418968C CN100418968C CNB2006100710947A CN200610071094A CN100418968C CN 100418968 C CN100418968 C CN 100418968C CN B2006100710947 A CNB2006100710947 A CN B2006100710947A CN 200610071094 A CN200610071094 A CN 200610071094A CN 100418968 C CN100418968 C CN 100418968C
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- Prior art keywords
- indole
- chloro
- mixture
- acid
- added
- Prior art date
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- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 10
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims abstract description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
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- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 29
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 15
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 12
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- 239000011777 magnesium Substances 0.000 description 4
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- RZLJPKOTDCNITI-UHFFFAOYSA-N methyl 1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-2,3-dihydroindole-2-carboxylate Chemical compound C1=CC=C2N(C(=O)C(C)NC(=O)OC(C)(C)C)C(C(=O)OC)CC2=C1 RZLJPKOTDCNITI-UHFFFAOYSA-N 0.000 description 4
- GWPMWXHPXNFEDW-UHFFFAOYSA-N methyl 6-chloro-2,3-dihydro-1h-indole-2-carboxylate Chemical compound C1=C(Cl)C=C2NC(C(=O)OC)CC2=C1 GWPMWXHPXNFEDW-UHFFFAOYSA-N 0.000 description 4
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
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- DLOFYLZHQBTQQA-UHFFFAOYSA-N ethyl 6-chloro-1h-pyrrolo[2,3-b]pyridine-2-carboxylate Chemical compound C1=C(Cl)N=C2NC(C(=O)OCC)=CC2=C1 DLOFYLZHQBTQQA-UHFFFAOYSA-N 0.000 description 3
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- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical class [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- GCZDLZHMAMLSJF-UHFFFAOYSA-N pyrazino[1,2-a]indole Chemical class C1=CN=CC2=CC3=CC=CC=C3N21 GCZDLZHMAMLSJF-UHFFFAOYSA-N 0.000 description 3
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- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 3
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 3
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Landscapes
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- Anesthesiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9902047.1 | 1999-01-29 | ||
| GBGB9902047.1A GB9902047D0 (en) | 1999-01-29 | 1999-01-29 | Chemical compounds XI |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CNB008031398A Division CN1289499C (zh) | 1999-01-29 | 2000-01-28 | 吡嗪并(氮杂)吲哚衍生物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1837207A CN1837207A (zh) | 2006-09-27 |
| CN100418968C true CN100418968C (zh) | 2008-09-17 |
Family
ID=10846774
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100710947A Expired - Fee Related CN100418968C (zh) | 1999-01-29 | 2000-01-28 | 吡嗪并(氮杂)吲哚衍生物 |
| CNB008031398A Expired - Fee Related CN1289499C (zh) | 1999-01-29 | 2000-01-28 | 吡嗪并(氮杂)吲哚衍生物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB008031398A Expired - Fee Related CN1289499C (zh) | 1999-01-29 | 2000-01-28 | 吡嗪并(氮杂)吲哚衍生物 |
Country Status (18)
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|---|---|
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| EP (1) | EP1147110B1 (enExample) |
| JP (1) | JP2002535408A (enExample) |
| KR (1) | KR100633375B1 (enExample) |
| CN (2) | CN100418968C (enExample) |
| AT (1) | ATE239731T1 (enExample) |
| AU (1) | AU758685B2 (enExample) |
| BR (1) | BR0008979A (enExample) |
| CA (1) | CA2359034A1 (enExample) |
| DE (1) | DE60002554T2 (enExample) |
| DK (1) | DK1147110T3 (enExample) |
| ES (1) | ES2199132T3 (enExample) |
| GB (1) | GB9902047D0 (enExample) |
| MX (1) | MXPA01007643A (enExample) |
| PT (1) | PT1147110E (enExample) |
| TR (1) | TR200102161T2 (enExample) |
| WO (1) | WO2000044753A1 (enExample) |
| ZA (1) | ZA200106202B (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6960579B1 (en) | 1998-05-19 | 2005-11-01 | Alcon Manufacturing, Ltd. | Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders |
| FR2799757B1 (fr) * | 1999-10-15 | 2001-12-14 | Adir | Nouveaux derives polycycliques azaindoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2002010169A1 (en) * | 2000-07-31 | 2002-02-07 | F. Hoffmann-La Roche Ag | Piperazine derivatives |
| SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
| JP4204315B2 (ja) | 2000-11-20 | 2009-01-07 | ビオヴィトルム・アクチボラゲット（プブリクト） | セロトニン５−ｈｔ２レセプターのアンタゴニストとしてのピペラジニルピラジン化合物 |
| HUP0303316A2 (hu) * | 2000-12-20 | 2004-01-28 | Bristol-Myers Squibb Pharma Company | Aril- és amino-aril-szubsztituált szerotoninreceptor agonista és antagonista ligandumok és ezeket tartalmazó gyógyszerkészítmények |
| GB0106177D0 (en) * | 2001-03-13 | 2001-05-02 | Hoffmann La Roche | Piperazine derivatives |
| ATE318821T1 (de) | 2001-06-01 | 2006-03-15 | Alcon Inc | Pyranoindazole und ihre verwendung in der glaukombehandlung |
| CA2447156A1 (en) | 2001-06-01 | 2002-12-12 | Alcon, Inc. | Novel fused indazoles and indoles and their use for the treatment of glaucoma |
| AU2002259312B2 (en) | 2001-06-01 | 2007-01-04 | Alcon, Inc. | Novel arylaminopropane analogues and their use for the treatment of glaucoma |
| US6825198B2 (en) | 2001-06-21 | 2004-11-30 | Pfizer Inc | 5-HT receptor ligands and uses thereof |
| TW593302B (en) | 2001-12-20 | 2004-06-21 | Alcon Inc | Novel benzodifuranimidazoline and benzofuranimidazoline derivatives and their use for the treatment of glaucoma |
| GB0202015D0 (en) | 2002-01-29 | 2002-03-13 | Hoffmann La Roche | Piperazine Derivatives |
| BR0311970A (pt) | 2002-06-19 | 2005-03-29 | Biovitrum Ab | Novos compostos, seu uso e preparação |
| BR0316775A (pt) | 2002-12-13 | 2005-11-01 | Alcon Inc | Novos análogos de benzopirano e seu uso para o tratamento de glaucoma |
| EP1636224B1 (en) * | 2003-05-21 | 2010-07-14 | Prosidion Limited | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phoshorylase |
| US7405210B2 (en) | 2003-05-21 | 2008-07-29 | Osi Pharmaceuticals, Inc. | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase |
| GB0314967D0 (en) * | 2003-06-26 | 2003-07-30 | Hoffmann La Roche | Piperazine derivatives |
| US7476687B2 (en) | 2003-11-26 | 2009-01-13 | Alcon, Inc. | Substituted furo[2,3-g]indazoles for the treatment of glaucoma |
| AR046890A1 (es) | 2003-12-15 | 2005-12-28 | Alcon Inc | [1,4] oxazino [2,3-g] indazoles sustituidos para el tratamiento del glaucoma. |
| US7129257B1 (en) | 2003-12-15 | 2006-10-31 | Alcon, Inc. | Pyrazolo[3,4- e]benzoxazoles for the treatment of glaucoma |
| US7338972B1 (en) | 2003-12-15 | 2008-03-04 | Alcon, Inc. | Substituted 1-alkylamino-1H-indazoles for the treatment of glaucoma |
| JP5173190B2 (ja) | 2004-08-25 | 2013-03-27 | 武田薬品工業株式会社 | 腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法 |
| WO2006062839A1 (en) | 2004-12-08 | 2006-06-15 | Alcon, Inc. | Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma |
| CA2609634C (en) * | 2005-05-03 | 2011-02-01 | F. Hoffmann-La Roche Ag | Tetracyclic azapyrazinoindolines as 5-ht2 ligands |
| UA95788C2 (en) | 2005-12-15 | 2011-09-12 | Ф. Хоффманн-Ля Рош Аг | Fused pyrrole derivatives |
| BRPI0619985A2 (pt) | 2005-12-16 | 2011-10-25 | Hoffmann La Roche | compostos, processo para a sua manufatura, composições farmacêuticas, métodos para o tratamento e/ou prevenção de enfermidades que estão associadas com a modulação de receptores de h3, de obesidade e de diabetes do tipo ii em um ser humano ou animal e usos dos compostos |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| EP2254886B1 (en) * | 2008-03-28 | 2016-05-25 | Nerviano Medical Sciences S.r.l. | 3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| WO2011071136A1 (ja) | 2009-12-11 | 2011-06-16 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| US20130267500A1 (en) | 2010-09-01 | 2013-10-10 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| MX363662B (es) * | 2012-10-08 | 2019-03-27 | Centro De Investig Y De Estudios Avanzados Del I P N Star | Métodos para incrementar la sensibilidad a insulina mediante agonistas de receptores serotonérgicos 5-ht2. |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| JP6217561B2 (ja) * | 2014-08-21 | 2017-10-25 | 信越化学工業株式会社 | 新規オニウム塩化合物及びレジスト組成物並びにパターン形成方法 |
| WO2019131902A1 (ja) | 2017-12-27 | 2019-07-04 | 武田薬品工業株式会社 | 腹圧性尿失禁および便失禁の治療薬 |
| IL292631A (en) * | 2019-10-31 | 2022-07-01 | Holosmedic | Novel compound and pharmaceutical composition for prevention or treatment of cancer comprising same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0572863A1 (de) * | 1992-06-05 | 1993-12-08 | F. Hoffmann-La Roche Ag | ZNS Pyrazinoindole |
| US5854245A (en) * | 1996-06-28 | 1998-12-29 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792724A (fr) * | 1971-12-16 | 1973-06-14 | Merck Patent Gmbh | Derives de pyrazinoindole et leur procede de preparation |
| TW334423B (en) | 1993-10-22 | 1998-06-21 | Hoffmann La Roche | Tricyclic 1-aminoethylpyrrole-derivatives |
| GB9819032D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Ltd | Chemical compounds IV |
| GB9819019D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Ltd | Chemical compounds II |
| GB9819035D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Res Ltd | Chemical compounds VII |
| GB9819033D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Ltd | Chemical compounds VI |
| GB9918962D0 (en) * | 1999-08-11 | 1999-10-13 | Cerebrus Ltd | Chemical compounds xxii |
-
1999
- 1999-01-29 GB GBGB9902047.1A patent/GB9902047D0/en not_active Ceased
-
2000
- 2000-01-28 DE DE60002554T patent/DE60002554T2/de not_active Expired - Fee Related
- 2000-01-28 AU AU21196/00A patent/AU758685B2/en not_active Ceased
- 2000-01-28 CA CA002359034A patent/CA2359034A1/en not_active Abandoned
- 2000-01-28 WO PCT/GB2000/000244 patent/WO2000044753A1/en not_active Ceased
- 2000-01-28 JP JP2000596009A patent/JP2002535408A/ja active Pending
- 2000-01-28 TR TR2001/02161T patent/TR200102161T2/xx unknown
- 2000-01-28 BR BR0008979-6A patent/BR0008979A/pt not_active Application Discontinuation
- 2000-01-28 KR KR1020017009583A patent/KR100633375B1/ko not_active Expired - Fee Related
- 2000-01-28 EP EP00901240A patent/EP1147110B1/en not_active Expired - Lifetime
- 2000-01-28 US US09/890,186 patent/US6800627B1/en not_active Expired - Fee Related
- 2000-01-28 DK DK00901240T patent/DK1147110T3/da active
- 2000-01-28 ES ES00901240T patent/ES2199132T3/es not_active Expired - Lifetime
- 2000-01-28 MX MXPA01007643A patent/MXPA01007643A/es not_active IP Right Cessation
- 2000-01-28 CN CNB2006100710947A patent/CN100418968C/zh not_active Expired - Fee Related
- 2000-01-28 AT AT00901240T patent/ATE239731T1/de not_active IP Right Cessation
- 2000-01-28 CN CNB008031398A patent/CN1289499C/zh not_active Expired - Fee Related
- 2000-01-28 PT PT00901240T patent/PT1147110E/pt unknown
-
2001
- 2001-07-27 ZA ZA200106202A patent/ZA200106202B/en unknown
-
2003
- 2003-08-05 US US10/633,532 patent/US20040039200A1/en not_active Abandoned
- 2003-10-16 US US10/685,799 patent/US7145009B2/en not_active Expired - Fee Related
-
2006
- 2006-03-14 US US11/374,157 patent/US20060160816A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0572863A1 (de) * | 1992-06-05 | 1993-12-08 | F. Hoffmann-La Roche Ag | ZNS Pyrazinoindole |
| US5854245A (en) * | 1996-06-28 | 1998-12-29 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60002554D1 (de) | 2003-06-12 |
| KR20010101873A (ko) | 2001-11-15 |
| AU758685B2 (en) | 2003-03-27 |
| CN1289499C (zh) | 2006-12-13 |
| EP1147110A1 (en) | 2001-10-24 |
| WO2000044753A1 (en) | 2000-08-03 |
| AU2119600A (en) | 2000-08-18 |
| DK1147110T3 (da) | 2003-09-01 |
| JP2002535408A (ja) | 2002-10-22 |
| US20060160816A1 (en) | 2006-07-20 |
| CA2359034A1 (en) | 2000-08-03 |
| PT1147110E (pt) | 2003-09-30 |
| EP1147110B1 (en) | 2003-05-07 |
| US6800627B1 (en) | 2004-10-05 |
| CN1337963A (zh) | 2002-02-27 |
| ZA200106202B (en) | 2002-07-29 |
| ES2199132T3 (es) | 2004-02-16 |
| KR100633375B1 (ko) | 2006-10-16 |
| MXPA01007643A (es) | 2003-06-24 |
| DE60002554T2 (de) | 2004-03-25 |
| US20040039200A1 (en) | 2004-02-26 |
| US20040092525A1 (en) | 2004-05-13 |
| BR0008979A (pt) | 2002-02-05 |
| TR200102161T2 (tr) | 2002-05-21 |
| US7145009B2 (en) | 2006-12-05 |
| CN1837207A (zh) | 2006-09-27 |
| ATE239731T1 (de) | 2003-05-15 |
| GB9902047D0 (en) | 1999-03-17 |
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