JP2011510026A5 - - Google Patents
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- Publication number
- JP2011510026A5 JP2011510026A5 JP2010543359A JP2010543359A JP2011510026A5 JP 2011510026 A5 JP2011510026 A5 JP 2011510026A5 JP 2010543359 A JP2010543359 A JP 2010543359A JP 2010543359 A JP2010543359 A JP 2010543359A JP 2011510026 A5 JP2011510026 A5 JP 2011510026A5
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- alkyl
- heterocycloalkyl
- compound
- group
- 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.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 claims 62
- 125000000217 alkyl group Chemical group 0.000 claims 61
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 55
- 125000001072 heteroaryl group Chemical group 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims 43
- -1 amidoalkyl Chemical group 0.000 claims 32
- 125000003545 alkoxy group Chemical group 0.000 claims 25
- 125000004104 aryloxy group Chemical group 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 25
- 239000001257 hydrogen Substances 0.000 claims 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 25
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 21
- 150000002367 halogens Chemical class 0.000 claims 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims 11
- 238000000034 method Methods 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims 9
- 125000004434 sulfur atom Chemical group 0.000 claims 9
- 150000002148 esters Chemical group 0.000 claims 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 229940126062 Compound A Drugs 0.000 claims 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- 102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 claims 2
- 108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 229940122344 Peptidase inhibitor Drugs 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 239000011975 tartaric acid Substances 0.000 claims 2
- 235000002906 tartaric acid Nutrition 0.000 claims 2
- XRSFPEFHACEZSM-UHFFFAOYSA-N 2,3,3a,4,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-5-one Chemical compound C1NCC2CC(=O)CC21 XRSFPEFHACEZSM-UHFFFAOYSA-N 0.000 claims 1
- XNCOCTMVJVBMKU-UHFFFAOYSA-N FC(C(=O)O)(F)F.N=1C(C=CC1)=O Chemical compound FC(C(=O)O)(F)F.N=1C(C=CC1)=O XNCOCTMVJVBMKU-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000005543 phthalimide group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- LGHAAAIUUYWURJ-UHFFFAOYSA-N tert-butyl 1h-pyrrole-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=CN1 LGHAAAIUUYWURJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200810004727 CN101230059B (zh) | 2007-01-23 | 2008-01-23 | 双环氮杂烷类衍生物、其制备方法及其在医药上的用途 |
| CN200810004727.1 | 2008-01-23 | ||
| PCT/CN2008/071014 WO2009094866A1 (en) | 2008-01-23 | 2008-05-20 | Dicycloazaalkane derivates, preparation processes and medical uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011510026A JP2011510026A (ja) | 2011-03-31 |
| JP2011510026A5 true JP2011510026A5 (enExample) | 2011-06-30 |
| JP5438028B2 JP5438028B2 (ja) | 2014-03-12 |
Family
ID=40921930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010543359A Expired - Fee Related JP5438028B2 (ja) | 2008-01-23 | 2008-05-20 | アザビシクロオクタンの誘導体、その製造方法及びそのジペプチジルペプチダーゼｉｖの阻害剤としての用途 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8304411B2 (enExample) |
| EP (1) | EP2246347B1 (enExample) |
| JP (1) | JP5438028B2 (enExample) |
| KR (1) | KR101469306B1 (enExample) |
| BR (1) | BRPI0822143A2 (enExample) |
| CA (1) | CA2712352C (enExample) |
| MX (1) | MX2010008049A (enExample) |
| RU (1) | RU2487866C2 (enExample) |
| WO (1) | WO2009094866A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102174007B (zh) * | 2011-03-11 | 2013-06-12 | 成都博天化工有限责任公司 | [2-(2-氰基-吡咯烷-1-基)-2-氧代-乙基]-氨基甲酸叔丁基酯的工业化制备方法 |
| WO2013091539A1 (zh) | 2011-12-21 | 2013-06-27 | 江苏恒瑞医药股份有限公司 | 吡咯并六元杂芳环类衍生物、其制备方法及其在医药上的应用 |
| WO2014000629A1 (zh) | 2012-06-25 | 2014-01-03 | 广东东阳光药业有限公司 | 六氢并环戊二烯衍生物、其制备方法及其在医药上的应用 |
| CN104030967B (zh) * | 2013-03-05 | 2018-01-02 | 连云港恒运药业有限公司 | 一种dpp‑iv抑制剂的中间体、其制备方法和通过其制备dpp‑iv抑制剂的方法 |
| US9540324B2 (en) | 2013-09-26 | 2017-01-10 | Luc Therapeutics, Inc. | Selective octahydro-cyclopenta[C] pyrrole negative modulators of NR2B |
| JO3579B1 (ar) | 2014-09-26 | 2020-07-05 | Luc Therapeutics Inc | مُعدِلات تفاغرية سالبة لمستقبل nr2b من المركب n-ألكيل أريل-5-أوكسي أريل-ثامن هيدرو-خماسي الحلقة [c] بيرول |
| US20170301620A1 (en) * | 2016-04-15 | 2017-10-19 | International Business Machines Corporation | Structure and process for metal cap integration |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5280028A (en) * | 1992-06-24 | 1994-01-18 | G. D. Searle & Co. | Benzimidazole compounds |
| US5736550A (en) * | 1994-05-18 | 1998-04-07 | Nisshin Flour Milling Co., Ltd. | Pyrimidine derivatives |
| TW492957B (en) | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
| US6110949A (en) | 1999-06-24 | 2000-08-29 | Novartis Ag | N-(substituted glycyl)-4-cyanothiazolidines, pharmaceutical compositions containing them and their use in inhibiting dipeptidyl peptidase-IV |
| ATE370943T1 (de) | 2001-06-27 | 2007-09-15 | Smithkline Beecham Corp | Fluoropyrrolidine als dipeptidyl-peptidase inhibitoren |
| US6861440B2 (en) * | 2001-10-26 | 2005-03-01 | Hoffmann-La Roche Inc. | DPP IV inhibitors |
| HUP0200849A2 (hu) | 2002-03-06 | 2004-08-30 | Sanofi-Synthelabo | N-aminoacetil-2-ciano-pirrolidin-származékok, e vegyületeket tartalmazó gyógyszerkészítmények és eljárás előállításukra |
| TW200401635A (en) * | 2002-07-23 | 2004-02-01 | Yamanouchi Pharma Co Ltd | 2-Cyano-4-fluoropyrrolidine derivative or salt thereof |
| GB0307856D0 (en) * | 2003-04-04 | 2003-05-14 | Novartis Ag | Organic compounds |
| CA2521271C (en) * | 2003-04-04 | 2011-01-04 | Novartis Ag | Quinoline-2-one-derivatives for the treatment of airways diseases |
| CA2557275C (en) * | 2004-02-27 | 2012-06-05 | Kyorin Pharmaceutical Co., Ltd. | Bicyclo derivative |
| FR2870538B1 (fr) * | 2004-05-19 | 2006-07-14 | Servier Lab | Nouveaux derives de pyrrolidines et de thiazolidines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US20070270417A1 (en) * | 2004-07-22 | 2007-11-22 | Glaxo Group Limited | Antibacterial Agents |
| WO2006028961A2 (en) * | 2004-09-03 | 2006-03-16 | Athersys, Inc. | Tricyclic heteroaryl piperazines, pyrrolidines and azetidines as serotonin receptor modulators |
| WO2007029086A2 (en) * | 2005-09-05 | 2007-03-15 | Ranbaxy Laboratories Limited | Derivatives of 3-azabicyclo[3.1.0]hexane as dipeptidyl peptidase-iv inhibitors |
| CN101050194B (zh) | 2006-04-05 | 2013-08-21 | 上海恒瑞医药有限公司 | 双环辛烷类衍生物、其制备方法及其在医药上的用途 |
| CN101230058A (zh) * | 2007-01-23 | 2008-07-30 | 上海恒瑞医药有限公司 | 双环氮杂烷类衍生物、其制备方法及其在医药上的用途 |
| CN101230059B (zh) | 2007-01-23 | 2011-08-17 | 上海恒瑞医药有限公司 | 双环氮杂烷类衍生物、其制备方法及其在医药上的用途 |
-
2008
- 2008-05-20 CA CA2712352A patent/CA2712352C/en not_active Expired - Fee Related
- 2008-05-20 BR BRPI0822143A patent/BRPI0822143A2/pt not_active IP Right Cessation
- 2008-05-20 EP EP08748620.5A patent/EP2246347B1/en not_active Not-in-force
- 2008-05-20 US US12/863,964 patent/US8304411B2/en not_active Expired - Fee Related
- 2008-05-20 RU RU2010128972/04A patent/RU2487866C2/ru not_active IP Right Cessation
- 2008-05-20 WO PCT/CN2008/071014 patent/WO2009094866A1/zh not_active Ceased
- 2008-05-20 JP JP2010543359A patent/JP5438028B2/ja not_active Expired - Fee Related
- 2008-05-20 MX MX2010008049A patent/MX2010008049A/es active IP Right Grant
- 2008-05-20 KR KR1020107018542A patent/KR101469306B1/ko not_active Expired - Fee Related
-
2012
- 2012-09-14 US US13/619,138 patent/US8415349B2/en not_active Expired - Fee Related
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