CA2553696A1 - Indazole-carboxamide compounds as 5-ht4 receptor agonists - Google Patents
Indazole-carboxamide compounds as 5-ht4 receptor agonists Download PDFInfo
- Publication number
- CA2553696A1 CA2553696A1 CA002553696A CA2553696A CA2553696A1 CA 2553696 A1 CA2553696 A1 CA 2553696A1 CA 002553696 A CA002553696 A CA 002553696A CA 2553696 A CA2553696 A CA 2553696A CA 2553696 A1 CA2553696 A1 CA 2553696A1
- Authority
- CA
- Canada
- Prior art keywords
- indazole
- carboxylic acid
- amide
- azabicyclo
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 108091005482 5-HT4 receptors Proteins 0.000 title claims abstract description 46
- 239000000018 receptor agonist Substances 0.000 title abstract description 17
- 229940044601 receptor agonist Drugs 0.000 title abstract description 17
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- 150000001875 compounds Chemical class 0.000 claims abstract description 201
- 238000000034 method Methods 0.000 claims abstract description 83
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 34
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- FHUPHXAYPNYFIU-UHFFFAOYSA-N 1-propan-2-ylindazole-3-carboxylic acid Chemical compound C1=CC=C2N(C(C)C)N=C(C(O)=O)C2=C1 FHUPHXAYPNYFIU-UHFFFAOYSA-N 0.000 claims description 120
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 111
- -1 (1S,3R,5R)-8-{2-[3-((S)-2-hydroxypropionylamino)pyrrolidin-1-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl Chemical group 0.000 claims description 92
- 150000001408 amides Chemical class 0.000 claims description 75
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 33
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- IEIAQSWMJMZELU-UHFFFAOYSA-N 5-fluoro-1-propan-2-ylindazole-3-carboxylic acid Chemical compound FC1=CC=C2N(C(C)C)N=C(C(O)=O)C2=C1 IEIAQSWMJMZELU-UHFFFAOYSA-N 0.000 claims description 5
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- SRLYWTDJCHALPO-UHFFFAOYSA-N 1-propylindazole-3-carboxylic acid Chemical compound C1=CC=C2N(CCC)N=C(C(O)=O)C2=C1 SRLYWTDJCHALPO-UHFFFAOYSA-N 0.000 claims description 2
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5044—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics involving specific cell types
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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
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
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- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
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- G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
- G01N2333/705—Assays involving receptors, cell surface antigens or cell surface determinants
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| US8309575B2 (en) | 2004-04-07 | 2012-11-13 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
| ATE431824T1 (de) * | 2004-11-05 | 2009-06-15 | Theravance Inc | Chinolinon-carboxamid-verbindungen |
| ATE441646T1 (de) * | 2004-11-05 | 2009-09-15 | Theravance Inc | 5-ht4-rezeptoragonistenverbindungen |
| WO2006069125A1 (en) * | 2004-12-22 | 2006-06-29 | Theravance, Inc. | Indazole-carboxamide compounds |
| JP2008530225A (ja) * | 2005-02-17 | 2008-08-07 | セラヴァンス， インコーポレーテッド | インダゾール−カルボキサミド化合物の結晶型 |
| WO2006094063A1 (en) * | 2005-03-02 | 2006-09-08 | Theravance, Inc. | Quinolinone compounds as 5-ht4 receptor agonists |
| ATE495171T1 (de) * | 2005-06-07 | 2011-01-15 | Theravance Inc | Benzimidazoloncarbonsäureamidverbindungen als agonisten des 5-ht4-rezeptors |
| WO2007102883A2 (en) * | 2005-10-25 | 2007-09-13 | Smithkline Beecham Corporation | Chemical compounds |
| MY143574A (en) * | 2005-11-22 | 2011-05-31 | Theravance Inc | Carbamate compounds as 5-ht4 receptor agonists |
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| ATE509021T1 (de) * | 2006-02-16 | 2011-05-15 | Theravance Inc | Verfahren zur herstellung von zwischenverbindungen zu 5-ht4-rezeptoragonist- verbindungen |
| KR100812499B1 (ko) * | 2006-10-16 | 2008-03-11 | 이도훈 | 항경련제 |
| WO2008101728A1 (de) * | 2007-02-23 | 2008-08-28 | K.H.S. Pharma Holding Gmbh | Verfahren zur herstellung von azoniaspironortropinestern und von nortropan-3-on verbindungen |
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| CN104271579A (zh) | 2012-05-03 | 2015-01-07 | 诺华股份有限公司 | 作为生长素释放肽受体激动剂的2,7-二氮杂-螺[4,5]癸烷-7-基衍生物的l-苹果酸盐及其结晶 |
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-
2005
- 2005-02-15 TW TW094104343A patent/TW200533348A/zh unknown
- 2005-02-17 CA CA002553696A patent/CA2553696A1/en not_active Abandoned
- 2005-02-17 AR ARP050100560A patent/AR047681A1/es unknown
- 2005-02-17 EP EP05723216A patent/EP1718643A1/en not_active Withdrawn
- 2005-02-17 CN CNA200580005307XA patent/CN1922175A/zh active Pending
- 2005-02-17 BR BRPI0507791-5A patent/BRPI0507791A/pt not_active IP Right Cessation
- 2005-02-17 KR KR1020067019088A patent/KR20060132727A/ko not_active Withdrawn
- 2005-02-17 WO PCT/US2005/005070 patent/WO2005080389A1/en not_active Ceased
- 2005-02-17 AU AU2005214368A patent/AU2005214368A1/en not_active Abandoned
- 2005-02-17 JP JP2006554207A patent/JP2007523175A/ja active Pending
- 2005-02-17 US US11/060,195 patent/US7351704B2/en active Active
- 2005-02-17 RU RU2006133320/04A patent/RU2006133320A/ru not_active Application Discontinuation
-
2006
- 2006-07-25 IL IL177059A patent/IL177059A0/en unknown
- 2006-08-03 ZA ZA200606479A patent/ZA200606479B/en unknown
- 2006-08-18 MA MA29276A patent/MA28435B1/fr unknown
- 2006-09-14 NO NO20064156A patent/NO20064156L/no not_active Application Discontinuation
-
2008
- 2008-02-04 US US12/012,579 patent/US7674908B2/en not_active Expired - Lifetime
-
2010
- 2010-01-19 US US12/689,763 patent/US8044045B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| RU2006133320A (ru) | 2008-03-27 |
| JP2007523175A (ja) | 2007-08-16 |
| US7674908B2 (en) | 2010-03-09 |
| AR047681A1 (es) | 2006-02-01 |
| US7351704B2 (en) | 2008-04-01 |
| US20080146807A1 (en) | 2008-06-19 |
| ZA200606479B (en) | 2008-01-30 |
| MA28435B1 (fr) | 2007-02-01 |
| KR20060132727A (ko) | 2006-12-21 |
| CN1922175A (zh) | 2007-02-28 |
| US20050197335A1 (en) | 2005-09-08 |
| TW200533348A (en) | 2005-10-16 |
| AU2005214368A1 (en) | 2005-09-01 |
| EP1718643A1 (en) | 2006-11-08 |
| NO20064156L (no) | 2006-11-10 |
| US8044045B2 (en) | 2011-10-25 |
| BRPI0507791A (pt) | 2007-07-17 |
| IL177059A0 (en) | 2006-12-10 |
| WO2005080389A1 (en) | 2005-09-01 |
| US20100261716A1 (en) | 2010-10-14 |
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