JP2016515110A5 - - Google Patents
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- Publication number
- JP2016515110A5 JP2016515110A5 JP2015562120A JP2015562120A JP2016515110A5 JP 2016515110 A5 JP2016515110 A5 JP 2016515110A5 JP 2015562120 A JP2015562120 A JP 2015562120A JP 2015562120 A JP2015562120 A JP 2015562120A JP 2016515110 A5 JP2016515110 A5 JP 2016515110A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- alkyl
- ring
- independently selected
- haloalkyl
- 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
- 229910052757 nitrogen Inorganic materials 0.000 claims description 78
- 229910052717 sulfur Inorganic materials 0.000 claims description 74
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 62
- 229910052760 oxygen Inorganic materials 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- 239000003112 inhibitor Substances 0.000 claims description 14
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- -1 tetrahydropyranyl-methyl - Chemical class 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 102100029921 Dipeptidyl peptidase 1 Human genes 0.000 claims description 2
- 101710087078 Dipeptidyl peptidase 1 Proteins 0.000 claims description 2
- 208000027004 Eosinophilic disease Diseases 0.000 claims description 2
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims description 2
- 229940122236 Histamine receptor antagonist Drugs 0.000 claims description 2
- 101000577881 Homo sapiens Macrophage metalloelastase Proteins 0.000 claims description 2
- 101000990902 Homo sapiens Matrix metalloproteinase-9 Proteins 0.000 claims description 2
- 102100027998 Macrophage metalloelastase Human genes 0.000 claims description 2
- 102100030412 Matrix metalloproteinase-9 Human genes 0.000 claims description 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 2
- 108050000258 Prostaglandin D receptors Proteins 0.000 claims description 2
- 102100024218 Prostaglandin D2 receptor 2 Human genes 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 230000003454 betamimetic effect Effects 0.000 claims description 2
- 239000000812 cholinergic antagonist Substances 0.000 claims description 2
- 239000003246 corticosteroid Substances 0.000 claims description 2
- 229940121647 egfr inhibitor Drugs 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 244000000010 microbial pathogen Species 0.000 claims description 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 239000003073 chemokine receptor CCR9 antagonist Substances 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 102100022718 Atypical chemokine receptor 2 Human genes 0.000 description 1
- GYLMCBOAXJVARF-UHFFFAOYSA-N C(C1)C2CNC1C2 Chemical compound C(C1)C2CNC1C2 GYLMCBOAXJVARF-UHFFFAOYSA-N 0.000 description 1
- KPUSZZFAYGWAHZ-UHFFFAOYSA-N C(C1)C2CNC1CC2 Chemical compound C(C1)C2CNC1CC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 description 1
- LKDJYZBKCVSODK-UHFFFAOYSA-N C(C1)C2NC1CNC2 Chemical compound C(C1)C2NC1CNC2 LKDJYZBKCVSODK-UHFFFAOYSA-N 0.000 description 1
- DJWDAKFSDBOQJK-UHFFFAOYSA-N C(C1)C2NCC1NC2 Chemical compound C(C1)C2NCC1NC2 DJWDAKFSDBOQJK-UHFFFAOYSA-N 0.000 description 1
- UKHJNJFJCGBKSF-UHFFFAOYSA-N C1C2NCC1NC2 Chemical compound C1C2NCC1NC2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N C1CCNCC1 Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N C1NCCNC1 Chemical compound C1NCCNC1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N C1NCc2ccccc12 Chemical compound C1NCc2ccccc12 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- SFLGSKRGOWRGBR-UHFFFAOYSA-N C1OCc2c1cccc2 Chemical compound C1OCc2c1cccc2 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N C1c2ccccc2NC1 Chemical compound C1c2ccccc2NC1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 description 1
- 101000716070 Homo sapiens C-C chemokine receptor type 9 Proteins 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13159242.0 | 2013-03-14 | ||
| EP13159242 | 2013-03-14 | ||
| EP13170006.4 | 2013-05-31 | ||
| EP13170006 | 2013-05-31 | ||
| PCT/EP2014/054827 WO2014140091A1 (en) | 2013-03-14 | 2014-03-12 | Substituted 2-aza-bicyclo[2.2.2]octane-3-carboxylic acid (benzyl-cyano-methyl)-amides inhibitors of cathepsin c |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016515110A JP2016515110A (ja) | 2016-05-26 |
| JP2016515110A5 true JP2016515110A5 (enExample) | 2017-04-13 |
| JP6441831B2 JP6441831B2 (ja) | 2018-12-19 |
Family
ID=50390052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015562120A Active JP6441831B2 (ja) | 2013-03-14 | 2014-03-12 | カテプシンｃの置換２−アザ−ビシクロ［２．２．２］オクタン−３−カルボン酸（ベンジル−シアノ−メチル）−アミド阻害剤 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US8877775B2 (enExample) |
| EP (1) | EP2970252B1 (enExample) |
| JP (1) | JP6441831B2 (enExample) |
| WO (1) | WO2014140091A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2668166C1 (ru) | 2013-12-17 | 2018-09-27 | Стелла Фарма Корпорейшн | Способ получения 2-фтор-4-бороно-l-фенилаланина и вещества-предшественника 2-фтор-4-бороно-l-фенилаланина |
| NO2699580T3 (enExample) | 2014-01-24 | 2018-02-24 | ||
| HUE047208T2 (hu) * | 2014-09-12 | 2020-04-28 | Boehringer Ingelheim Int | A katepszin-C spirociklikus inhibitorai |
| ES2912276T3 (es) * | 2015-04-07 | 2022-05-25 | Ela Pharma Ltd | Composiciones para tratar y/o prevenir necrosis celular o tisular que seleccionan como diana específicamente catepsina C y/o CELA1 y/o CELA3A y/o enzimas estructuralmente relacionadas con las mismas |
| PT3758708T (pt) | 2018-03-01 | 2025-02-13 | Astrazeneca Ab | Composições farmacêuticas compreendendo (2s)-{(1,s)-1-ciano-2-[4-(3-metil-2-oxo-2,3-di-hidro-1,3-benzoxazol-5-il)fenil]etil}-1,4-oxazepano-2-carboxamida |
| CA3106269A1 (en) | 2018-07-17 | 2020-01-23 | Insmed Incorporated | Certain (2s)-n-[(1s)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamides for treating lupus nephritis |
| CN110452139B (zh) * | 2019-08-23 | 2021-07-09 | 黄河三角洲京博化工研究院有限公司 | 一种2-甲基-3-溴-6-甲砜基苯腈的制备方法 |
| AU2021314104A1 (en) | 2020-07-20 | 2023-01-19 | Insmed, Inc. | Methods for extracting neutrophil serine proteases and treating dipeptidyl peptidase 1-mediated conditions |
| CN114159446A (zh) | 2020-09-11 | 2022-03-11 | 中国科学院上海营养与健康研究所 | 组织蛋白酶c抑制剂在治疗肿瘤转移中的应用 |
| TWI834476B (zh) * | 2022-01-27 | 2024-03-01 | 禾榮科技股份有限公司 | 中間體、其製備方法和製備藥物的方法 |
| US20230234973A1 (en) * | 2022-01-27 | 2023-07-27 | Heron Neutron Medical Corp. | Intermediate, preparing method thereof, and method of preparing drug |
| JP2026503035A (ja) | 2023-01-06 | 2026-01-27 | インスメッド インコーポレイテッド | 新規な可逆性ｄｐｐ１阻害剤及びその用途 |
| CN121511233A (zh) * | 2023-06-27 | 2026-02-10 | 海思科医药集团股份有限公司 | 一种dpp1抑制剂中间体及其制备方法及在医药中的用途 |
| WO2025162472A1 (en) | 2024-01-31 | 2025-08-07 | Insmed Incorporated | Linear dipeptidyl peptidase 1 inhibitors and uses thereof |
| WO2026148258A2 (en) | 2025-01-03 | 2026-07-09 | Insmed Incorporated | Dipeptidyl peptidase 1 inhibitors and uses thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4125727A (en) | 1976-10-18 | 1978-11-14 | American Cyanamid Company | Method of preparing imidazoisoindolediones |
| ATE339404T1 (de) * | 1999-12-24 | 2006-10-15 | Hoffmann La Roche | Nitrilderivate als cathepsin k hemmer |
| US6960597B2 (en) | 2000-06-30 | 2005-11-01 | Orth-Mcneil Pharmaceutical, Inc. | Aza-bridged-bicyclic amino acid derivatives as α4 integrin antagonists |
| DE60229114D1 (en) | 2001-03-02 | 2008-11-13 | Axys Pharm Inc | Cathepsincystein-proteasehemmer |
| WO2004110988A1 (en) | 2003-06-18 | 2004-12-23 | Prozymex A/S | Protease inhibitors |
| TW200528440A (en) | 2003-10-31 | 2005-09-01 | Fujisawa Pharmaceutical Co | 2-cyanopyrrolidinecarboxamide compound |
| US20060223846A1 (en) * | 2005-03-08 | 2006-10-05 | Dyatkin Alexey B | Aza-bridged-bicyclic amino acid derivatives as alpha4 integrin antagonists |
| WO2009047829A1 (ja) | 2007-10-12 | 2009-04-16 | Fujitsu Limited | Ｉｐ電話自動試験システム及び方法 |
| US7902181B2 (en) * | 2007-12-12 | 2011-03-08 | Astrazeneca Ab | Compounds 010 |
| EA201190235A1 (ru) | 2009-05-07 | 2012-05-30 | Астразенека Аб | Замещенные 1-цианоэтилгетероциклилкарбоксамидные соединения 750 |
| WO2010142985A1 (en) * | 2009-06-10 | 2010-12-16 | Astrazeneca Ab | Substituted n-[1-cyano-2-(phenyl)ethyl]piperidin-2-ylcarboxmide compounds 761 |
| WO2011154677A1 (en) * | 2010-06-09 | 2011-12-15 | Astrazeneca Ab | Substituted n-[1-cyano-2-(phenyl)ethyl] 1-aminocycloalk-1-ylcarboxamide compounds - 760 |
| WO2012119941A1 (en) | 2011-03-04 | 2012-09-13 | Prozymex A/S | Peptidyl nitrilcompounds as peptidase inhibitors |
| US8999975B2 (en) | 2011-09-19 | 2015-04-07 | Boehringer Ingelheim International Gmbh | Substituted N- [1-cyano-2- (phenyl) ethyl] -2-azabicyclo [2.2.1] heptane-3-carboxamide inhibitors of cathepsin C |
-
2014
- 2014-03-12 EP EP14713395.3A patent/EP2970252B1/en active Active
- 2014-03-12 JP JP2015562120A patent/JP6441831B2/ja active Active
- 2014-03-12 WO PCT/EP2014/054827 patent/WO2014140091A1/en not_active Ceased
- 2014-03-12 US US14/205,867 patent/US8877775B2/en active Active
- 2014-09-11 US US14/483,217 patent/US9073869B2/en active Active
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