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 | 2013-03-14 | ||
| EP13159242.0 | 2013-03-14 | ||
| EP13170006 | 2013-05-31 | ||
| EP13170006.4 | 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 (OSRAM) | 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 (OSRAM) |
| EP (1) | EP2970252B1 (OSRAM) |
| JP (1) | JP6441831B2 (OSRAM) |
| WO (1) | WO2014140091A1 (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3085687B1 (en) | 2013-12-17 | 2020-06-17 | Stella Pharma Corporation | Production method for 2-fluoro-4-borono-l-phenylalanine, and precursor of 2-fluoro-4-borono-l-phenylalanine |
| NO2699580T3 (OSRAM) | 2014-01-24 | 2018-02-24 | ||
| KR102510588B1 (ko) * | 2014-09-12 | 2023-03-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 카텝신 c의 스피로사이클릭 억제제 |
| JP2018515597A (ja) | 2015-04-07 | 2018-06-14 | イーエルエイ ファーマ リミテッドＥｌａ Ｐｈａｒｍａ Ｌｔｄ | カテプシンｃおよび／またはｃｅｌａ１および／またはｃｅｌａ３ａおよび／またはそれらに構造的に関連する酵素を特異的に標的とする細胞および／または組織壊死の処置および／または防止のための組成物 |
| AU2019228717C1 (en) | 2018-03-01 | 2025-01-09 | Astrazeneca Ab | Pharmaceutical compositions comprising (2S)-N-{(1S)-1-cyano-2-[4-(3-methyl-2- oxo-2,3-dihydro-1,3-benzoxazol-5-yl)phenyl]ethyl}-1,4-oxazepane-2-carboxamide |
| 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 |
| CA3181285A1 (en) | 2020-07-20 | 2022-01-27 | Jessica BASSO | Methods for extracting neutrophil serine proteases and treating dipeptidyl peptidase 1-mediated conditions |
| 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 |
| CN120584108A (zh) | 2023-01-06 | 2025-09-02 | 英斯梅德股份有限公司 | 新型可逆dpp1抑制剂及其用途 |
| WO2025002093A1 (zh) * | 2023-06-27 | 2025-01-02 | 西藏海思科制药有限公司 | 一种dpp1抑制剂中间体及其制备方法及在医药中的用途 |
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 |
| CN1240681C (zh) * | 1999-12-24 | 2006-02-08 | 霍夫曼-拉罗奇有限公司 | 作为组织蛋白酶k抑制剂的腈衍生物 |
| US6960597B2 (en) | 2000-06-30 | 2005-11-01 | Orth-Mcneil Pharmaceutical, Inc. | Aza-bridged-bicyclic amino acid derivatives as α4 integrin antagonists |
| US7012075B2 (en) | 2001-03-02 | 2006-03-14 | Merck & Co., Inc. | Cathepsin cysteine protease inhibitors |
| EP1638925A1 (en) | 2003-06-18 | 2006-03-29 | Prozymex A/S | Protease inhibitors |
| TW200528440A (en) | 2003-10-31 | 2005-09-01 | Fujisawa Pharmaceutical Co | 2-cyanopyrrolidinecarboxamide compound |
| WO2006096807A1 (en) * | 2005-03-08 | 2006-09-14 | Janssen Pharmaceutica N.V. | Aza-bridged-bicyclic amino acid derivatives as alpha 4 integrin antagonists |
| JP5240201B2 (ja) | 2007-10-12 | 2013-07-17 | 富士通株式会社 | Ｉｐ電話自動試験システム及び方法 |
| JP2011506421A (ja) * | 2007-12-12 | 2011-03-03 | アストラゼネカ・アクチエボラーグ | ペプチジルニトリル類およびジペプチジルペプチダーゼｉ阻害剤としてのその使用 |
| EP2427445A1 (en) | 2009-05-07 | 2012-03-14 | AstraZeneca AB | Substituted 1-cyanoethylheterocyclylcarboxamide compounds 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 US US14/205,867 patent/US8877775B2/en active Active
- 2014-03-12 WO PCT/EP2014/054827 patent/WO2014140091A1/en not_active Ceased
- 2014-03-12 EP EP14713395.3A patent/EP2970252B1/en active Active
- 2014-03-12 JP JP2015562120A patent/JP6441831B2/ja active Active
- 2014-09-11 US US14/483,217 patent/US9073869B2/en active Active
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