CA2333629A1 - Furopyridine derivatives and their therapeutical use - Google Patents
Furopyridine derivatives and their therapeutical use Download PDFInfo
- Publication number
- CA2333629A1 CA2333629A1 CA002333629A CA2333629A CA2333629A1 CA 2333629 A1 CA2333629 A1 CA 2333629A1 CA 002333629 A CA002333629 A CA 002333629A CA 2333629 A CA2333629 A CA 2333629A CA 2333629 A1 CA2333629 A1 CA 2333629A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridine
- carboxylic acid
- amide
- alkyl
- methoxyfuro
- 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
- 230000001225 therapeutic effect Effects 0.000 title claims abstract description 6
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical class C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 184
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 7
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims abstract description 5
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims abstract description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 5
- 230000005764 inhibitory process Effects 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 70
- -1 heterocyclo Chemical group 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 150000001408 amides Chemical class 0.000 claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
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- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
- ISIQAMHROGZHOV-UHFFFAOYSA-N 3,5-dichloropyridin-4-amine Chemical compound NC1=C(Cl)C=NC=C1Cl ISIQAMHROGZHOV-UHFFFAOYSA-N 0.000 claims description 10
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- 125000003545 alkoxy group Chemical group 0.000 claims description 8
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- 125000001424 substituent group Chemical group 0.000 claims description 6
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
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- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 3
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
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- 239000003937 drug carrier Substances 0.000 claims description 3
- CCAJLYNVQAPNDK-UHFFFAOYSA-N furo[2,3-c]pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CN=CC2=C1C=CO2 CCAJLYNVQAPNDK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- FMOKVKNOLGASDQ-UHFFFAOYSA-N 2-acetyl-7-methoxy-n-(3-methylpyridin-4-yl)furo[2,3-c]pyridine-4-carboxamide Chemical compound C1=2C=C(C(C)=O)OC=2C(OC)=NC=C1C(=O)NC1=CC=NC=C1C FMOKVKNOLGASDQ-UHFFFAOYSA-N 0.000 claims description 2
- UUZUZXKIHFCSMM-UHFFFAOYSA-N 2-acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid Chemical compound COC1=NC=C(C(O)=O)C2=C1OC(C(C)=O)=C2 UUZUZXKIHFCSMM-UHFFFAOYSA-N 0.000 claims description 2
- OVRQXTOABUYRBP-UHFFFAOYSA-N 2-ethyl-7-methoxy-n-(3-methoxypyridin-4-yl)furo[2,3-c]pyridine-4-carboxamide Chemical compound C1=NC(OC)=C2OC(CC)=CC2=C1C(=O)NC1=CC=NC=C1OC OVRQXTOABUYRBP-UHFFFAOYSA-N 0.000 claims description 2
- MXZUIDYEQFPNEH-UHFFFAOYSA-N 2-ethyl-7-methoxy-n-(3-methylpyridin-4-yl)furo[2,3-c]pyridine-4-carboxamide Chemical compound C1=NC(OC)=C2OC(CC)=CC2=C1C(=O)NC1=CC=NC=C1C MXZUIDYEQFPNEH-UHFFFAOYSA-N 0.000 claims description 2
- OATQEIAUQAVLFI-UHFFFAOYSA-N 7-methoxy-2-(4-methoxy-1-methylpiperidin-4-yl)furo[2,3-c]pyridine-4-carboxylic acid Chemical compound O1C=2C(OC)=NC=C(C(O)=O)C=2C=C1C1(OC)CCN(C)CC1 OATQEIAUQAVLFI-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
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- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 206010027175 memory impairment Diseases 0.000 claims description 2
- JESCGEWQDVNBSE-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxamide Chemical compound C1=NC(OC)=C2OC(CC)=CC2=C1C(=O)NC1=C(Cl)C=NC=C1Cl JESCGEWQDVNBSE-UHFFFAOYSA-N 0.000 claims description 2
- CLOSCVOTKUSWOJ-UHFFFAOYSA-N n-(3-chloropyridin-4-yl)-2-ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxamide Chemical compound C1=NC(OC)=C2OC(CC)=CC2=C1C(=O)NC1=CC=NC=C1Cl CLOSCVOTKUSWOJ-UHFFFAOYSA-N 0.000 claims description 2
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- 210000003979 eosinophil Anatomy 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- XPOYYJQVQOMCEL-UHFFFAOYSA-N 2-acetyl-n-(3,5-dichloropyridin-4-yl)-7-methoxyfuro[2,3-c]pyridine-4-carboxamide Chemical compound C1=2C=C(C(C)=O)OC=2C(OC)=NC=C1C(=O)NC1=C(Cl)C=NC=C1Cl XPOYYJQVQOMCEL-UHFFFAOYSA-N 0.000 claims 1
- KBWZNINGQMYRLL-UHFFFAOYSA-N 2-ethyl-7-methoxy-n-(2,4,6-trifluorophenyl)furo[2,3-c]pyridine-4-carboxamide Chemical compound C1=NC(OC)=C2OC(CC)=CC2=C1C(=O)NC1=C(F)C=C(F)C=C1F KBWZNINGQMYRLL-UHFFFAOYSA-N 0.000 claims 1
- HTHCTEPBVMVZEO-UHFFFAOYSA-N 7-(difluoromethoxy)-2-ethyl-n-[2-(trifluoromethyl)phenyl]furo[2,3-c]pyridine-4-carboxamide Chemical compound C1=NC(OC(F)F)=C2OC(CC)=CC2=C1C(=O)NC1=CC=CC=C1C(F)(F)F HTHCTEPBVMVZEO-UHFFFAOYSA-N 0.000 claims 1
- YGQBWCUTYFBTLH-UHFFFAOYSA-N 7-(difluoromethoxy)-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid Chemical compound C1=NC(OC(F)F)=C2OC(CC)=CC2=C1C(O)=O YGQBWCUTYFBTLH-UHFFFAOYSA-N 0.000 claims 1
- AHYNSZBGYURKIP-UHFFFAOYSA-N 7-(difluoromethoxy)-n-(3,5-dimethyl-1,2-oxazol-4-yl)-2-ethylfuro[2,3-c]pyridine-4-carboxamide Chemical compound C1=NC(OC(F)F)=C2OC(CC)=CC2=C1C(=O)NC=1C(C)=NOC=1C AHYNSZBGYURKIP-UHFFFAOYSA-N 0.000 claims 1
- JBHMSHKWKKUOBI-UHFFFAOYSA-N 7-methoxy-2-(methoxymethyl)furo[2,3-c]pyridine-4-carboxylic acid Chemical compound C1=NC(OC)=C2OC(COC)=CC2=C1C(O)=O JBHMSHKWKKUOBI-UHFFFAOYSA-N 0.000 claims 1
- FJACYEGKPUDXGT-UHFFFAOYSA-N 7-methoxy-2-(oxolan-3-yl)furo[2,3-c]pyridine-4-carboxylic acid Chemical compound O1C=2C(OC)=NC=C(C(O)=O)C=2C=C1C1CCOC1 FJACYEGKPUDXGT-UHFFFAOYSA-N 0.000 claims 1
- GAYIUIZSLAYZQD-UHFFFAOYSA-N 7-methoxy-2-pyridin-3-ylfuro[2,3-c]pyridine-4-carboxylic acid Chemical compound O1C=2C(OC)=NC=C(C(O)=O)C=2C=C1C1=CC=CN=C1 GAYIUIZSLAYZQD-UHFFFAOYSA-N 0.000 claims 1
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- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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Landscapes
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9812322.7A GB9812322D0 (en) | 1998-06-08 | 1998-06-08 | Benzofurans and their therapeutic use |
| GB9812322.7 | 1998-06-08 | ||
| GB9820768.1 | 1998-09-23 | ||
| GBGB9820768.1A GB9820768D0 (en) | 1998-09-23 | 1998-09-23 | Heterocyclic compounds and their therapeutic use |
| PCT/GB1999/001791 WO1999064423A1 (en) | 1998-06-08 | 1999-06-07 | Furopyridine derivatives and their therapeutical use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2333629A1 true CA2333629A1 (en) | 1999-12-16 |
Family
ID=26313823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002333629A Abandoned CA2333629A1 (en) | 1998-06-08 | 1999-06-07 | Furopyridine derivatives and their therapeutical use |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6169090B1 (https=) |
| EP (1) | EP1086106B1 (https=) |
| JP (1) | JP2003526601A (https=) |
| AT (1) | ATE247660T1 (https=) |
| AU (1) | AU753897B2 (https=) |
| CA (1) | CA2333629A1 (https=) |
| CO (1) | CO5080802A1 (https=) |
| DE (1) | DE69910568T2 (https=) |
| ES (1) | ES2204171T3 (https=) |
| PE (1) | PE20000734A1 (https=) |
| TW (1) | TW555759B (https=) |
| WO (1) | WO1999064423A1 (https=) |
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| WO2000038683A1 (en) * | 1998-12-23 | 2000-07-06 | Du Pont Pharmaceuticals Company | THROMBIN OR FACTOR Xa INHIBITORS |
| US7217722B2 (en) | 2000-02-01 | 2007-05-15 | Kirin Beer Kabushiki Kaisha | Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same |
| GB0003256D0 (en) * | 2000-02-11 | 2000-04-05 | Darwin Discovery Ltd | Heterocyclic compounds and their therapeutic use |
| WO2002012189A1 (en) * | 2000-08-09 | 2002-02-14 | Mitsubishi Pharma Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| US8176296B2 (en) | 2000-10-26 | 2012-05-08 | Cypress Semiconductor Corporation | Programmable microcontroller architecture |
| US6724220B1 (en) | 2000-10-26 | 2004-04-20 | Cyress Semiconductor Corporation | Programmable microcontroller architecture (mixed analog/digital) |
| US6479493B1 (en) | 2001-08-23 | 2002-11-12 | Cell Pathways, Inc. | Methods for treatment of type I diabetes |
| MXPA05009921A (es) * | 2003-03-17 | 2005-11-04 | Kyowa Hakko Kogyo Kk | Agentes terapeuticos y/o preventivos para enfermedades cutaneas cronicas. |
| DE10318610A1 (de) * | 2003-04-24 | 2004-11-11 | Elbion Ag | 7-Azaindole und deren Verwendung als Therapeutika |
| US8069436B2 (en) | 2004-08-13 | 2011-11-29 | Cypress Semiconductor Corporation | Providing hardware independence to automate code generation of processing device firmware |
| JP5878327B2 (ja) * | 2011-10-12 | 2016-03-08 | 花王株式会社 | 手洗い用食器洗浄剤組成物 |
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| US4910193A (en) | 1985-12-16 | 1990-03-20 | Sandoz Ltd. | Treatment of gastrointestinal disorders |
| US5559127A (en) | 1992-10-14 | 1996-09-24 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| AU673569B2 (en) | 1992-12-02 | 1996-11-14 | Pfizer Inc. | Catechol diethers as selective PDE-IV inhibitors |
| ATE180780T1 (de) | 1993-08-05 | 1999-06-15 | Hoechst Marion Roussel Inc | 2-(piperidin-4-yl, pyridin-4-yl und tetrahydropyridin-4-yl)-benzofuran-7-carbamat derivate, ihre herstellung und verwendung als acetylcholinesterase inhibitoren |
| JPH07267961A (ja) * | 1994-03-30 | 1995-10-17 | Taisho Pharmaceut Co Ltd | ベンゾフロ［３，２−ｄピリミジン−４−オン誘導体 |
| WO1996036638A1 (en) | 1995-05-19 | 1996-11-21 | Chiroscience Limited | Xanthines and their therapeutic use |
| JPH09108832A (ja) | 1995-10-19 | 1997-04-28 | Mitsubishi Electric Corp | 溶接構造体およびその溶接方法 |
| KR19990071894A (ko) * | 1995-12-05 | 1999-09-27 | 마르크 젠너 | 벤조퓨란 카르복사미드 및 술폰아미드 |
| ES2187775T3 (es) * | 1996-05-15 | 2003-06-16 | Altana Pharma Ag | Imidazopiridinas. |
| CN1219171A (zh) * | 1996-05-20 | 1999-06-09 | 达尔文发现有限公司 | 苯并呋喃甲酰胺及其治疗用途 |
| WO1998007715A1 (en) * | 1996-08-19 | 1998-02-26 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Novel benzofuran-4-carboxamides |
| JP4166296B2 (ja) | 1997-04-25 | 2008-10-15 | 塩野義製薬株式会社 | ドーパミン受容体拮抗作用を有する化合物 |
-
1999
- 1999-06-03 TW TW088109174A patent/TW555759B/zh active
- 1999-06-07 DE DE69910568T patent/DE69910568T2/de not_active Expired - Fee Related
- 1999-06-07 ES ES99955472T patent/ES2204171T3/es not_active Expired - Lifetime
- 1999-06-07 EP EP99955472A patent/EP1086106B1/en not_active Expired - Lifetime
- 1999-06-07 CA CA002333629A patent/CA2333629A1/en not_active Abandoned
- 1999-06-07 AU AU42776/99A patent/AU753897B2/en not_active Ceased
- 1999-06-07 JP JP2000553432A patent/JP2003526601A/ja active Pending
- 1999-06-07 WO PCT/GB1999/001791 patent/WO1999064423A1/en not_active Ceased
- 1999-06-07 AT AT99955472T patent/ATE247660T1/de not_active IP Right Cessation
- 1999-06-08 US US09/328,182 patent/US6169090B1/en not_active Expired - Fee Related
- 1999-06-08 PE PE1999000510A patent/PE20000734A1/es not_active Application Discontinuation
- 1999-06-08 CO CO99035782A patent/CO5080802A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PE20000734A1 (es) | 2000-08-18 |
| AU753897B2 (en) | 2002-10-31 |
| CO5080802A1 (es) | 2001-09-25 |
| DE69910568D1 (de) | 2003-09-25 |
| EP1086106B1 (en) | 2003-08-20 |
| ES2204171T3 (es) | 2004-04-16 |
| ATE247660T1 (de) | 2003-09-15 |
| WO1999064423A1 (en) | 1999-12-16 |
| EP1086106A1 (en) | 2001-03-28 |
| AU4277699A (en) | 1999-12-30 |
| TW555759B (en) | 2003-10-01 |
| JP2003526601A (ja) | 2003-09-09 |
| DE69910568T2 (de) | 2004-06-17 |
| US6169090B1 (en) | 2001-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |