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)
- Indole Compounds (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 |
|---|---|---|---|
| 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
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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 |
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| CNB008031398A Expired - Fee Related CN1289499C (zh) | 1999-01-29 | 2000-01-28 | 吡嗪并(氮杂)吲哚衍生物 |
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|---|---|
| US (4) | US6800627B1 (enExample) |
| 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 |
| CN1277828C (zh) * | 2000-07-31 | 2006-10-04 | 霍夫曼-拉罗奇有限公司 | 哌嗪衍生物 |
| SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
| DE60139021D1 (de) | 2000-11-20 | 2009-07-30 | Biovitrum Ab Publ | Piperazinylpyrazinverbindungen als antagonisten des serotonin-5-ht2-rezeptors |
| JP2005506280A (ja) * | 2000-12-20 | 2005-03-03 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | アリールおよびアミノアリール置換セロトニン受容体アゴニストおよびアンタゴニストリガンド |
| GB0106177D0 (en) | 2001-03-13 | 2001-05-02 | Hoffmann La Roche | Piperazine derivatives |
| EP1392658A4 (en) | 2001-06-01 | 2004-10-13 | Alcon Inc | NOVEL FUSED INDAZOLES AND INDOLES AND THEIR USE IN THE TREATMENT OF GLAUCOMES |
| WO2002098400A1 (en) | 2001-06-01 | 2002-12-12 | Alcon, Inc. | Novel arylaminopropane analogues and their use for the treatment of glaucoma |
| DK1392292T3 (da) | 2001-06-01 | 2006-05-29 | Alcon Inc | Pyranoindazoler og deres anvendelse til behandling af glaukom |
| 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 |
| EP1513831B1 (en) | 2002-06-19 | 2010-01-06 | Biovitrum AB (publ) | Novel compounds, their use and preparation |
| AU2003300915B2 (en) | 2002-12-13 | 2008-08-28 | Alcon, Inc. | Novel benzopyran analogs and their use for the treatment of glaucoma |
| US7405210B2 (en) | 2003-05-21 | 2008-07-29 | Osi Pharmaceuticals, Inc. | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase |
| DE602004028122D1 (de) * | 2003-05-21 | 2010-08-26 | Prosidion Ltd | Pyrrolopyridin-2-carbonsäuren als hemmer der glycogenphosphorylase |
| GB0314967D0 (en) | 2003-06-26 | 2003-07-30 | Hoffmann La Roche | Piperazine derivatives |
| WO2005053688A1 (en) | 2003-11-26 | 2005-06-16 | Alcon, Inc. | Substituted furo[2,3-g] indazoles 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 |
| 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 |
| EP2400300A1 (en) | 2004-08-25 | 2011-12-28 | Takeda Pharmaceutical Company Limited | Method of screening preventives/remedies for stress urinary incontinence |
| WO2006062839A1 (en) | 2004-12-08 | 2006-06-15 | Alcon, Inc. | Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma |
| CN101171252B (zh) * | 2005-05-03 | 2011-06-01 | 霍夫曼-拉罗奇有限公司 | 作为5-ht2配体的四环氮杂吡嗪并二氢吲哚类化合物 |
| UA95788C2 (en) | 2005-12-15 | 2011-09-12 | Ф. Хоффманн-Ля Рош Аг | Fused pyrrole derivatives |
| US7351708B2 (en) | 2005-12-16 | 2008-04-01 | Hoffmann-La Roche Inc. | Pyrrolo [2,3-b] pyridine derivatives |
| WO2007132841A1 (ja) | 2006-05-16 | 2007-11-22 | Takeda Pharmaceutical Company Limited | 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 |
| US8207165B2 (en) | 2008-03-28 | 2012-06-26 | 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 |
| JPWO2011071136A1 (ja) | 2009-12-11 | 2013-04-22 | 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 |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
| MX2022004739A (es) * | 2019-10-31 | 2022-07-19 | Holosmedic | Compuesto novedoso y composicion farmaceutica para prevencion o tratamiento de cancer que comprende el mismo. |
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 |
Family Cites Families (7)
| 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 |
| GB9819033D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Ltd | Chemical compounds VI |
| GB9819035D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Res Ltd | Chemical compounds VII |
| 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 |
| 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 DK DK00901240T patent/DK1147110T3/da active
- 2000-01-28 CN CNB2006100710947A patent/CN100418968C/zh not_active Expired - Fee Related
- 2000-01-28 US US09/890,186 patent/US6800627B1/en not_active Expired - Fee Related
- 2000-01-28 PT PT00901240T patent/PT1147110E/pt unknown
- 2000-01-28 JP JP2000596009A patent/JP2002535408A/ja active Pending
- 2000-01-28 ES ES00901240T patent/ES2199132T3/es not_active Expired - Lifetime
- 2000-01-28 CA CA002359034A patent/CA2359034A1/en not_active Abandoned
- 2000-01-28 KR KR1020017009583A patent/KR100633375B1/ko not_active Expired - Fee Related
- 2000-01-28 DE DE60002554T patent/DE60002554T2/de not_active Expired - Fee Related
- 2000-01-28 TR TR2001/02161T patent/TR200102161T2/xx unknown
- 2000-01-28 AT AT00901240T patent/ATE239731T1/de not_active IP Right Cessation
- 2000-01-28 EP EP00901240A patent/EP1147110B1/en not_active Expired - Lifetime
- 2000-01-28 WO PCT/GB2000/000244 patent/WO2000044753A1/en not_active Ceased
- 2000-01-28 CN CNB008031398A patent/CN1289499C/zh not_active Expired - Fee Related
- 2000-01-28 AU AU21196/00A patent/AU758685B2/en not_active Ceased
- 2000-01-28 MX MXPA01007643A patent/MXPA01007643A/es not_active IP Right Cessation
- 2000-01-28 BR BR0008979-6A patent/BR0008979A/pt not_active Application Discontinuation
-
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 |
|---|---|
| PT1147110E (pt) | 2003-09-30 |
| JP2002535408A (ja) | 2002-10-22 |
| KR100633375B1 (ko) | 2006-10-16 |
| KR20010101873A (ko) | 2001-11-15 |
| US7145009B2 (en) | 2006-12-05 |
| ZA200106202B (en) | 2002-07-29 |
| AU758685B2 (en) | 2003-03-27 |
| CN1289499C (zh) | 2006-12-13 |
| DK1147110T3 (da) | 2003-09-01 |
| CA2359034A1 (en) | 2000-08-03 |
| DE60002554T2 (de) | 2004-03-25 |
| TR200102161T2 (tr) | 2002-05-21 |
| EP1147110A1 (en) | 2001-10-24 |
| AU2119600A (en) | 2000-08-18 |
| EP1147110B1 (en) | 2003-05-07 |
| DE60002554D1 (de) | 2003-06-12 |
| US6800627B1 (en) | 2004-10-05 |
| US20040039200A1 (en) | 2004-02-26 |
| CN1837207A (zh) | 2006-09-27 |
| CN1337963A (zh) | 2002-02-27 |
| ATE239731T1 (de) | 2003-05-15 |
| ES2199132T3 (es) | 2004-02-16 |
| US20040092525A1 (en) | 2004-05-13 |
| US20060160816A1 (en) | 2006-07-20 |
| BR0008979A (pt) | 2002-02-05 |
| GB9902047D0 (en) | 1999-03-17 |
| MXPA01007643A (es) | 2003-06-24 |
| WO2000044753A1 (en) | 2000-08-03 |
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