NO312833B1 - Indazolkarboksamider, fremgangsmåte for fremstilling derav, anvendelse av forbindelsene samt farmasöytiske preparaterinneholdende disse - Google Patents
Indazolkarboksamider, fremgangsmåte for fremstilling derav, anvendelse av forbindelsene samt farmasöytiske preparaterinneholdende disse Download PDFInfo
- Publication number
- NO312833B1 NO312833B1 NO19974221A NO974221A NO312833B1 NO 312833 B1 NO312833 B1 NO 312833B1 NO 19974221 A NO19974221 A NO 19974221A NO 974221 A NO974221 A NO 974221A NO 312833 B1 NO312833 B1 NO 312833B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- compound
- mmol
- indazole
- piperidinyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 82
- 150000001875 compounds Chemical class 0.000 title claims description 75
- 238000000034 method Methods 0.000 title claims description 33
- DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical class C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 title abstract description 4
- 230000008569 process Effects 0.000 title description 8
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000011282 treatment Methods 0.000 claims abstract description 17
- -1 1-piperazinyl Chemical group 0.000 claims description 39
- 125000001624 naphthyl group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 8
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 6
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000005073 adamantyl group Chemical class C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
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- 125000003545 alkoxy group Chemical group 0.000 claims description 2
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- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
- QEZYDSSGVBTNBH-UHFFFAOYSA-N n-[2-[4-(adamantane-1-carbonylamino)piperidin-1-yl]ethyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN1CCC(NC(=O)C23CC4CC(CC(C4)C2)C3)CC1 QEZYDSSGVBTNBH-UHFFFAOYSA-N 0.000 claims 2
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- FEDKTGOMGVYEHB-UHFFFAOYSA-N benzyl n-[1-[2-[(1-propan-2-ylindazole-3-carbonyl)amino]ethyl]piperidin-4-yl]carbamate Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN(CC1)CCC1NC(=O)OCC1=CC=CC=C1 FEDKTGOMGVYEHB-UHFFFAOYSA-N 0.000 claims 1
- KHGJIEFWRMMWSG-UHFFFAOYSA-N n-[2-(4-acetamidopiperidin-1-yl)ethyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN1CCC(NC(C)=O)CC1 KHGJIEFWRMMWSG-UHFFFAOYSA-N 0.000 claims 1
- HMNUTMYCGLRBNS-UHFFFAOYSA-N n-[2-[4-[(3-hydroxyadamantane-1-carbonyl)amino]piperidin-1-yl]ethyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN1CCC(NC(=O)C23CC4(O)CC(CC(C4)C2)C3)CC1 HMNUTMYCGLRBNS-UHFFFAOYSA-N 0.000 claims 1
- MIDLORDGBDNOLV-UHFFFAOYSA-N n-[2-[4-[(4-hydroxyadamantane-1-carbonyl)amino]piperidin-1-yl]ethyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN1CCC(NC(=O)C23CC4CC(CC(C4O)C3)C2)CC1 MIDLORDGBDNOLV-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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
- C07D401/12—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 chain containing hetero atoms as chain links
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40511995A | 1995-03-16 | 1995-03-16 | |
| US08/485,956 US5654320A (en) | 1995-03-16 | 1995-06-07 | Indazolecarboxamides |
| PCT/US1996/003551 WO1996033713A1 (en) | 1995-03-16 | 1996-03-14 | Indazolecarboxamides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO974221D0 NO974221D0 (no) | 1997-09-12 |
| NO974221L NO974221L (no) | 1997-10-27 |
| NO312833B1 true NO312833B1 (no) | 2002-07-08 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19974221A NO312833B1 (no) | 1995-03-16 | 1997-09-12 | Indazolkarboksamider, fremgangsmåte for fremstilling derav, anvendelse av forbindelsene samt farmasöytiske preparaterinneholdende disse |
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|---|---|
| US (2) | US5798367A (ro) |
| EP (1) | EP0732333B1 (ro) |
| JP (1) | JPH11502230A (ro) |
| CN (1) | CN1112923C (ro) |
| AT (1) | ATE203748T1 (ro) |
| AU (1) | AU700842B2 (ro) |
| BR (1) | BR9608223A (ro) |
| CA (1) | CA2215359A1 (ro) |
| DE (1) | DE69614164T2 (ro) |
| DK (1) | DK0732333T3 (ro) |
| EA (1) | EA000699B1 (ro) |
| ES (1) | ES2159345T3 (ro) |
| GR (1) | GR3037029T3 (ro) |
| HU (1) | HU223973B1 (ro) |
| IL (1) | IL117438A (ro) |
| NO (1) | NO312833B1 (ro) |
| NZ (1) | NZ315971A (ro) |
| PL (1) | PL183867B1 (ro) |
| PT (1) | PT732333E (ro) |
| RO (1) | RO119617B1 (ro) |
| SK (1) | SK283924B6 (ro) |
| TR (1) | TR199700956T1 (ro) |
| WO (1) | WO1996033713A1 (ro) |
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| IT1291569B1 (it) * | 1997-04-15 | 1999-01-11 | Angelini Ricerche Spa | Indazolammidi come agenti serotoninergici |
| US5914405A (en) * | 1997-10-07 | 1999-06-22 | Eli Lilly And Company | Process for preparing 3-substituted indazoles |
| US6069152A (en) * | 1997-10-07 | 2000-05-30 | Eli Lilly And Company | 5-HT4 agonists and antagonists |
| EE05054B1 (et) * | 1998-08-21 | 2008-08-15 | Novartis Ag | 5-HT4 agonisti v?i antagonisti peroraalne ravimkoostis ja selle kasutamine meditsiinis |
| CA2340952C (en) | 1998-09-10 | 2009-12-08 | F. Hoffmann-La Roche Ag | Dihydrobenzodioxine carboxamide and ketone derivatives as 5-ht4 receptor antagonists |
| WO2002004411A1 (en) | 2000-07-07 | 2002-01-17 | The Administrators Of The Tulane Educational Fund | Methods for protection of stratified squamous epithelium against injury by noxious substances and novel agents for use therefor |
| US20050032866A1 (en) * | 2000-08-07 | 2005-02-10 | Bonhomme Mireille Marguerite Jeanne | The use of 5ht4 receptor antagonists in the prophylaxis or treatment of certain cardiovascular conditions |
| EP1321142A1 (en) * | 2001-12-21 | 2003-06-25 | Novartis AG | Solid pharmaceutical composition for oral administration of Tegaserod |
| AU2003208711A1 (en) | 2002-02-12 | 2003-09-04 | Akzo Nobel N.V. | 1-arylsulfonyl-3-substituted indole and indoline derivatives useful in the treatment of central nervous system disorders |
| ITMI20030287A1 (it) | 2003-02-18 | 2004-08-19 | Acraf | Indazolammidi dotate di attivita' analgesica metodo, per |
| ITMI20031467A1 (it) * | 2003-07-18 | 2005-01-19 | Acraf | Farmaco attivo nel dolore neuropatico |
| ITMI20031468A1 (it) * | 2003-07-18 | 2005-01-19 | Acraf | Farmaco ativo nel dolore neuropatico |
| SE0401969D0 (sv) * | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Piperidine derivatives |
| DE602006010563D1 (de) | 2005-07-22 | 2009-12-31 | Pfizer | Indazolcarbonsäureamidderivate als agonisten des 5ht4-rezeptors |
| WO2009106980A2 (en) * | 2008-02-29 | 2009-09-03 | Pfizer Inc. | Indazole derivatives |
| GB201511382D0 (en) | 2015-06-29 | 2015-08-12 | Imp Innovations Ltd | Novel compounds and their use in therapy |
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|---|---|---|---|---|
| US3145215A (en) * | 1961-12-19 | 1964-08-18 | Sterling Drug Inc | Indazole derivatives |
| JP2795460B2 (ja) * | 1988-06-20 | 1998-09-10 | 協和醗酵工業株式会社 | ピラゾロアクリドン誘導体 |
| US5017573A (en) * | 1988-07-29 | 1991-05-21 | Dainippon Pharmaceutical Co., Ltd. | Indazole-3-carboxylic acid derivatives |
| EP0410509A1 (en) * | 1989-07-25 | 1991-01-30 | Duphar International Research B.V | New substituted 1H-indazole-3-carboxamides |
| HU211081B (en) * | 1990-12-18 | 1995-10-30 | Sandoz Ag | Process for producing indole derivatives as serotonin antagonists and pharmaceutical compositions containing the same |
| NZ243993A (en) * | 1991-08-20 | 1994-10-26 | Smithkline Beecham Plc | Pharmaceutical compositions having 5-ht4 receptor antagonist activity and selected compounds having such activity |
| US5552398A (en) * | 1991-09-12 | 1996-09-03 | Smithkline Beecham P.L.C. | Azabicyclic compounds as 5-HT4 receptor antagonists |
| AU4081393A (en) * | 1992-05-23 | 1993-12-30 | Smithkline Beecham Plc | Medicaments for the treatment of anxiety |
| WO1994000113A2 (en) * | 1992-06-27 | 1994-01-06 | Smithkline Beecham Plc | Medicaments containing 5-ht4 receptor antagonists |
| MX9305947A (es) * | 1992-09-29 | 1994-06-30 | Smithkline Beecham Plc | Compuestos antagonistas del receptor 5-ht4, procedimiento para su preparacion y composiciones farmaceuticas que las contienen. |
| TW251287B (ro) * | 1993-04-30 | 1995-07-11 | Nissei Co Ltd | |
| GB9310582D0 (en) * | 1993-05-22 | 1993-07-07 | Smithkline Beecham Plc | Pharmaceuticals |
-
1996
- 1996-03-11 IL IL11743896A patent/IL117438A/en active IP Right Grant
- 1996-03-12 DE DE69614164T patent/DE69614164T2/de not_active Expired - Fee Related
- 1996-03-12 PT PT96301682T patent/PT732333E/pt unknown
- 1996-03-12 EP EP96301682A patent/EP0732333B1/en not_active Expired - Lifetime
- 1996-03-12 AT AT96301682T patent/ATE203748T1/de not_active IP Right Cessation
- 1996-03-12 ES ES96301682T patent/ES2159345T3/es not_active Expired - Lifetime
- 1996-03-12 DK DK96301682T patent/DK0732333T3/da active
- 1996-03-14 WO PCT/US1996/003551 patent/WO1996033713A1/en active IP Right Grant
- 1996-03-14 TR TR97/00956T patent/TR199700956T1/xx unknown
- 1996-03-14 PL PL96322362A patent/PL183867B1/pl not_active IP Right Cessation
- 1996-03-14 SK SK1242-97A patent/SK283924B6/sk unknown
- 1996-03-14 BR BR9608223A patent/BR9608223A/pt not_active IP Right Cessation
- 1996-03-14 HU HU9801386A patent/HU223973B1/hu not_active IP Right Cessation
- 1996-03-14 RO RO97-01719A patent/RO119617B1/ro unknown
- 1996-03-14 JP JP8528690A patent/JPH11502230A/ja not_active Ceased
- 1996-03-14 EA EA199700242A patent/EA000699B1/ru not_active IP Right Cessation
- 1996-03-14 NZ NZ315971A patent/NZ315971A/xx unknown
- 1996-03-14 CN CN96193677A patent/CN1112923C/zh not_active Expired - Fee Related
- 1996-03-14 AU AU68948/96A patent/AU700842B2/en not_active Ceased
- 1996-03-14 CA CA002215359A patent/CA2215359A1/en not_active Abandoned
-
1997
- 1997-01-10 US US08/781,421 patent/US5798367A/en not_active Expired - Fee Related
- 1997-01-10 US US08/782,478 patent/US5817676A/en not_active Expired - Fee Related
- 1997-09-12 NO NO19974221A patent/NO312833B1/no unknown
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2001
- 2001-10-26 GR GR20010401899T patent/GR3037029T3/el not_active IP Right Cessation
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