JP2010516635A5 - - Google Patents
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- Publication number
- JP2010516635A5 JP2010516635A5 JP2009545800A JP2009545800A JP2010516635A5 JP 2010516635 A5 JP2010516635 A5 JP 2010516635A5 JP 2009545800 A JP2009545800 A JP 2009545800A JP 2009545800 A JP2009545800 A JP 2009545800A JP 2010516635 A5 JP2010516635 A5 JP 2010516635A5
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- heterocycloalkyl
- group
- alkyl
- heteroaryl
- 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
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- 125000003118 aryl group Chemical group 0.000 claims description 107
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 103
- 125000000217 alkyl group Chemical group 0.000 claims description 99
- 125000001072 heteroaryl group Chemical group 0.000 claims description 89
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 72
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000004104 aryloxy group Chemical group 0.000 claims description 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 38
- 150000001735 carboxylic acids Chemical group 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 37
- -1 cycloalkoxyl Chemical group 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002148 esters Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- DWTGOKLGTPRPDS-UHFFFAOYSA-N OS(=O)(=O)C(F)(F)F.C1NCC2C1CC(C2)=O Chemical compound OS(=O)(=O)C(F)(F)F.C1NCC2C1CC(C2)=O DWTGOKLGTPRPDS-UHFFFAOYSA-N 0.000 claims description 2
- SAOWVLRYNSDGEF-UHFFFAOYSA-N OS(=O)(=O)C(F)(F)F.N1=CC=CC1=O Chemical compound OS(=O)(=O)C(F)(F)F.N1=CC=CC1=O SAOWVLRYNSDGEF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 239000005457 ice water Substances 0.000 claims description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- GGNDIMLSSMWKDR-UHFFFAOYSA-N tert-butyl 5-oxo-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate Chemical compound C1C(=O)CC2CN(C(=O)OC(C)(C)C)CC21 GGNDIMLSSMWKDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 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
- 239000002253 acid Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- BKHDYBMGEZPELT-UHFFFAOYSA-N 1-(2-aminoacetyl)pyrrolidine-2-carbonitrile;hydrochloride Chemical compound Cl.NCC(=O)N1CCCC1C#N BKHDYBMGEZPELT-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 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
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 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
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 26
- 150000002431 hydrogen Chemical class 0.000 description 23
- 125000004103 aminoalkyl group Chemical group 0.000 description 6
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 0 **(C1)[Ts]C(C2)C1*C2O Chemical compound **(C1)[Ts]C(C2)C1*C2O 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200710004330.8 | 2007-01-23 | ||
| CNA2007100043308A CN101230058A (zh) | 2007-01-23 | 2007-01-23 | 双环氮杂烷类衍生物、其制备方法及其在医药上的用途 |
| PCT/CN2007/070990 WO2008089636A1 (en) | 2007-01-23 | 2007-10-30 | Derivatives of azabicyclo octane, the method of making them and the uses thereof as inhibitors of dipeptidyl peptidase iv |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010516635A JP2010516635A (ja) | 2010-05-20 |
| JP2010516635A5 true JP2010516635A5 (show.php) | 2013-12-05 |
| JP5424256B2 JP5424256B2 (ja) | 2014-02-26 |
Family
ID=39644101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009545800A Expired - Fee Related JP5424256B2 (ja) | 2007-01-23 | 2007-10-30 | 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 (11)
| Country | Link |
|---|---|
| US (1) | US8178575B2 (show.php) |
| EP (1) | EP2133077B1 (show.php) |
| JP (1) | JP5424256B2 (show.php) |
| KR (1) | KR101482159B1 (show.php) |
| CN (2) | CN101230058A (show.php) |
| AU (1) | AU2007345133B8 (show.php) |
| BR (1) | BRPI0719650A2 (show.php) |
| CA (1) | CA2673164C (show.php) |
| MX (1) | MX2009007765A (show.php) |
| RU (1) | RU2447063C2 (show.php) |
| WO (1) | WO2008089636A1 (show.php) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8304411B2 (en) | 2008-01-23 | 2012-11-06 | Jiangsu Hansoh Pharmaceutical Co., Ltd. | Dicycloazaalkane derivates, preparation processes and medical uses thereof |
| CN101919851B (zh) * | 2009-06-09 | 2012-02-08 | 江苏恒瑞医药股份有限公司 | 治疗哺乳动物包括人2型糖尿病的药物组合物 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| SI2796460T1 (sl) * | 2011-12-21 | 2018-10-30 | Jiangsu Hengrui Medicine Co. Ltd | Pirolni šestčlenski derivat heteroarilnega obroča, postopek priprave zanj in medicinske uporabe le-tega |
| CN102827063B (zh) * | 2012-08-14 | 2014-06-25 | 华东师范大学 | 一种氮杂双环[3.3.0]辛烷衍生物的合成方法 |
| CN102827064B (zh) * | 2012-08-14 | 2014-01-29 | 华东师范大学 | 一种氮杂双环[3.3.0]辛烷衍生物的合成方法 |
| CN103709150B (zh) * | 2012-10-09 | 2017-06-30 | 江苏豪森药业集团有限公司 | 托西酸贝格列汀晶型及其制备方法和用途 |
| WO2014064215A1 (en) | 2012-10-24 | 2014-05-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | TPL2 KINASE INHIBITORS FOR PREVENTING OR TREATING DIABETES AND FOR PROMOTING β-CELL SURVIVAL |
| US9540324B2 (en) * | 2013-09-26 | 2017-01-10 | Luc Therapeutics, Inc. | Selective octahydro-cyclopenta[C] pyrrole negative modulators of NR2B |
| ES2805743T3 (es) | 2015-03-24 | 2021-02-15 | Inst Nat Sante Rech Med | Método y composición farmacéutica para uso en el tratamiento de la diabetes |
| TWI771342B (zh) | 2016-11-23 | 2022-07-21 | 大陸商江蘇恆瑞醫藥股份有限公司 | 吡咯并六員雜芳環類衍生物的製備方法及中間體 |
| CN118063442A (zh) | 2017-10-20 | 2024-05-24 | 范德比尔特大学 | 毒蕈碱性乙酰胆碱受体m4的拮抗剂 |
| KR20200081424A (ko) | 2017-10-31 | 2020-07-07 | 반더빌트유니버시티 | 무스카린성 아세틸콜린 수용체 m4의 길항제 |
| MX2020006128A (es) | 2017-12-15 | 2020-09-21 | Praxis Biotech LLC | Inhibidores de la proteina de activacion de fibroblastos. |
| KR20200116945A (ko) | 2018-02-02 | 2020-10-13 | 반더빌트유니버시티 | 무스카린성 아세틸콜린 수용체 m4의 길항제 |
| JP2022514352A (ja) | 2018-12-21 | 2022-02-10 | プラクシス バイオテック エルエルシー | 線維芽細胞活性化タンパク質の阻害剤 |
| CN111620816B (zh) * | 2020-05-27 | 2023-06-02 | 上海赛默罗生物科技有限公司 | 螺桨烷类衍生物、其制备方法、药物组合物和用途 |
Family Cites Families (15)
| 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 |
| US6395767B2 (en) * | 2000-03-10 | 2002-05-28 | Bristol-Myers Squibb Company | Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method |
| 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 |
| KR101078505B1 (ko) * | 2003-03-14 | 2011-10-31 | 오노 야꾸힝 고교 가부시키가이샤 | 질소 함유 복소환 유도체 및 이들을 유효 성분으로 하는약제 |
| GB0307856D0 (en) * | 2003-04-04 | 2003-05-14 | Novartis Ag | Organic compounds |
| ATE421322T1 (de) * | 2003-04-04 | 2009-02-15 | Novartis Pharma Gmbh | Chinolin-2-on-derivate zur behandlung von erkankungen der atemwege |
| US7381738B2 (en) * | 2004-02-19 | 2008-06-03 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7288563B2 (en) * | 2004-02-19 | 2007-10-30 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| EP1778688A1 (en) * | 2004-07-22 | 2007-05-02 | Glaxo Group Limited | Antibacterial agents |
| DE602005027861D1 (de) * | 2004-09-03 | 2011-06-16 | Athersys Inc | Trizyklische heteroaryl-piperazine, pyrrolidine und azetidine als serotonin-rezeptor-modulatoren |
| 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 |
-
2007
- 2007-01-23 CN CNA2007100043308A patent/CN101230058A/zh active Pending
- 2007-10-30 KR KR1020097017567A patent/KR101482159B1/ko not_active Expired - Fee Related
- 2007-10-30 EP EP07817181.6A patent/EP2133077B1/en active Active
- 2007-10-30 BR BRPI0719650-4A patent/BRPI0719650A2/pt not_active IP Right Cessation
- 2007-10-30 RU RU2009124304/04A patent/RU2447063C2/ru not_active IP Right Cessation
- 2007-10-30 MX MX2009007765A patent/MX2009007765A/es active IP Right Grant
- 2007-10-30 JP JP2009545800A patent/JP5424256B2/ja not_active Expired - Fee Related
- 2007-10-30 WO PCT/CN2007/070990 patent/WO2008089636A1/zh not_active Ceased
- 2007-10-30 CA CA2673164A patent/CA2673164C/en not_active Expired - Fee Related
- 2007-10-30 AU AU2007345133A patent/AU2007345133B8/en not_active Ceased
- 2007-10-30 US US12/518,259 patent/US8178575B2/en not_active Expired - Fee Related
-
2008
- 2008-01-23 CN CN2010102292364A patent/CN101914092B/zh not_active Expired - Fee Related
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