JP2016529264A5 - - Google Patents
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- Publication number
- JP2016529264A5 JP2016529264A5 JP2016537144A JP2016537144A JP2016529264A5 JP 2016529264 A5 JP2016529264 A5 JP 2016529264A5 JP 2016537144 A JP2016537144 A JP 2016537144A JP 2016537144 A JP2016537144 A JP 2016537144A JP 2016529264 A5 JP2016529264 A5 JP 2016529264A5
- Authority
- JP
- Japan
- Prior art keywords
- disease
- phenyl
- oxazole
- carboxylic acid
- acid amide
- 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
- 150000001875 compounds Chemical class 0.000 claims 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 16
- 201000010099 disease Diseases 0.000 claims 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 claims 7
- 102100032028 Non-receptor tyrosine-protein kinase TYK2 Human genes 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 230000002401 inhibitory effect Effects 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 3
- 206010052779 Transplant rejections Diseases 0.000 claims 3
- 208000024908 graft versus host disease Diseases 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- -1 hydroxy, amino Chemical group 0.000 claims 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 108010010057 TYK2 Kinase Proteins 0.000 claims 2
- 102000015774 TYK2 Kinase Human genes 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 238000003745 diagnosis Methods 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- KUMWERTZYYEHSV-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-5-(4-methylsulfonylanilino)-1,3-oxazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=C(F)C=2)F)O1 KUMWERTZYYEHSV-UHFFFAOYSA-N 0.000 claims 1
- VSESJZFXWMRDNW-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-5-(4-methylsulfonylanilino)-1,3-oxazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=CC=2Cl)Cl)O1 VSESJZFXWMRDNW-UHFFFAOYSA-N 0.000 claims 1
- GPSWUDJBYRLTRW-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-5-[4-(morpholine-4-carbonyl)anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2Cl)Cl)OC=1NC(C=C1)=CC=C1C(=O)N1CCOCC1 GPSWUDJBYRLTRW-UHFFFAOYSA-N 0.000 claims 1
- LPYWGQFKWKJYDB-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-5-[4-[(1-methylpiperidin-4-yl)carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=CC=2Cl)Cl)O1 LPYWGQFKWKJYDB-UHFFFAOYSA-N 0.000 claims 1
- OLKSZFBBMNHFRV-CQSZACIVSA-N 2-(2,6-dichlorophenyl)-5-[4-[[(3r)-piperidin-3-yl]carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2Cl)Cl)OC=1NC(C=C1)=CC=C1C(=O)N[C@@H]1CCCNC1 OLKSZFBBMNHFRV-CQSZACIVSA-N 0.000 claims 1
- OLKSZFBBMNHFRV-AWEZNQCLSA-N 2-(2,6-dichlorophenyl)-5-[4-[[(3s)-piperidin-3-yl]carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2Cl)Cl)OC=1NC(C=C1)=CC=C1C(=O)N[C@H]1CCCNC1 OLKSZFBBMNHFRV-AWEZNQCLSA-N 0.000 claims 1
- VAWFTMZJZHXRFN-UHFFFAOYSA-N 2-(2,6-difluorophenyl)-5-(4-ethylsulfonylanilino)-1,3-oxazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=CC=2F)F)O1 VAWFTMZJZHXRFN-UHFFFAOYSA-N 0.000 claims 1
- HEDPDFHTQKEORT-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-5-[4-(morpholine-4-carbonyl)anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2F)Cl)OC=1NC(C=C1)=CC=C1C(=O)N1CCOCC1 HEDPDFHTQKEORT-UHFFFAOYSA-N 0.000 claims 1
- BGJWNODSJDKPEG-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-5-[4-[(1-methylpiperidin-4-yl)carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=CC=2F)Cl)O1 BGJWNODSJDKPEG-UHFFFAOYSA-N 0.000 claims 1
- XJIZKYUARXWFSC-CQSZACIVSA-N 2-(2-chloro-6-fluorophenyl)-5-[4-[[(3r)-piperidin-3-yl]carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2F)Cl)OC=1NC(C=C1)=CC=C1C(=O)N[C@@H]1CCCNC1 XJIZKYUARXWFSC-CQSZACIVSA-N 0.000 claims 1
- XJIZKYUARXWFSC-AWEZNQCLSA-N 2-(2-chloro-6-fluorophenyl)-5-[4-[[(3s)-piperidin-3-yl]carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2F)Cl)OC=1NC(C=C1)=CC=C1C(=O)N[C@H]1CCCNC1 XJIZKYUARXWFSC-AWEZNQCLSA-N 0.000 claims 1
- 208000026872 Addison Disease Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 206010008909 Chronic Hepatitis Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 1
- 206010013774 Dry eye Diseases 0.000 claims 1
- 206010073306 Exposure to radiation Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 206010019755 Hepatitis chronic active Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 claims 1
- 208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 210000004100 adrenal gland Anatomy 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000009285 allergic inflammation Effects 0.000 claims 1
- 150000001408 amides Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 230000006020 chronic inflammation Effects 0.000 claims 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 150000002222 fluorine compounds Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 206010023332 keratitis Diseases 0.000 claims 1
- 201000010666 keratoconjunctivitis Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 238000012216 screening Methods 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 230000007863 steatosis Effects 0.000 claims 1
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2013/068198 WO2015032423A1 (en) | 2013-09-03 | 2013-09-03 | Pharmaceutical compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016529264A JP2016529264A (ja) | 2016-09-23 |
| JP2016529264A5 true JP2016529264A5 (enExample) | 2016-11-04 |
| JP6239118B2 JP6239118B2 (ja) | 2017-11-29 |
Family
ID=49237179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016537144A Active JP6239118B2 (ja) | 2013-09-03 | 2013-09-03 | 医薬化合物 |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JP6239118B2 (enExample) |
| KR (1) | KR102191084B1 (enExample) |
| CN (1) | CN105793245B (enExample) |
| AU (1) | AU2013399913B2 (enExample) |
| BR (1) | BR112016004723B1 (enExample) |
| CA (1) | CA2941824C (enExample) |
| IL (1) | IL244380B (enExample) |
| MX (1) | MX369974B (enExample) |
| RU (1) | RU2652795C2 (enExample) |
| SG (1) | SG11201601503SA (enExample) |
| WO (1) | WO2015032423A1 (enExample) |
| ZA (1) | ZA201602047B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201617871D0 (en) | 2016-10-21 | 2016-12-07 | Sareum Limited | Pharmaceutical compounds |
| WO2019132654A1 (en) * | 2017-12-27 | 2019-07-04 | Erasmus University Medical Center Rotterdam | Methods of treating sarcoidosis |
| WO2020009566A1 (en) * | 2018-07-04 | 2020-01-09 | Erasmus University Medical Center Rotterdam | Methods of treating sarcoidosis |
| GB201816369D0 (en) * | 2018-10-08 | 2018-11-28 | Sareum Ltd | Pharmaceutical compounds |
| WO2020222773A1 (en) | 2019-04-30 | 2020-11-05 | Celgene Corporation | Combination therapies comprising apremilast and tyk2 inhibitors |
| GB202005114D0 (en) | 2020-04-07 | 2020-05-20 | Sareum Ltd | Crystalline Forms of a Pharmaceutical Compound |
| EP3944859A1 (en) | 2020-07-30 | 2022-02-02 | Assistance Publique Hôpitaux de Paris | Method for treating immune toxicities induced by immune checkpoint inhibitors |
| US20240390369A1 (en) | 2021-09-30 | 2024-11-28 | Bristol-Myers Squibb Company | Methods for determining responsiveness to tyk2 inhibitors |
| KR20240111312A (ko) | 2021-10-25 | 2024-07-16 | 카이메라 쎄라퓨틱스 인코포레이티드 | Tyk2 분해제 및 이의 용도 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1497536A (en) * | 1973-12-17 | 1978-01-12 | Lilly Industries Ltd | 2-acylaminooxazoles methods for their preparation and their use |
| PL344004A1 (en) * | 1998-05-05 | 2001-09-10 | Hoffmann La Roche | Pyrazole derivatives as p-38 map kinase inhibitors |
| GB0709031D0 (en) * | 2007-05-10 | 2007-06-20 | Sareum Ltd | Pharmaceutical compounds |
| US8367706B2 (en) | 2007-06-20 | 2013-02-05 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| EP2278969B1 (en) | 2008-04-21 | 2013-02-13 | Merck Sharp & Dohme Corp. | Inhibitors of Janus kinases |
| EP2299816B1 (en) | 2008-06-18 | 2013-11-13 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| EP2310384B1 (en) | 2008-07-09 | 2014-04-09 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| EP2166006A1 (en) * | 2008-09-18 | 2010-03-24 | Dompe' S.P.A. | 2-aryl-propionic acids and derivatives and pharmaceutical compositions containing them |
| GB0820819D0 (en) * | 2008-11-13 | 2008-12-24 | Sareum Ltd | Pharmaceutical compounds |
| US20130096104A1 (en) | 2010-03-17 | 2013-04-18 | Genentech, Inc. | Imidazopyridine compounds, compositions and methods of use |
| US20130143915A1 (en) | 2010-07-01 | 2013-06-06 | Cellzome Limited | Triazolopyridines as tyk2 inhibitors |
| SG11201401342VA (en) | 2011-10-12 | 2014-09-26 | Array Biopharma Inc | 5,7-substituted-imidazo[1,2-c]pyrimidines |
| ES2566205T3 (es) * | 2012-03-02 | 2016-04-11 | Sareum Limited | Inhibidores de quinasa TYK2 |
-
2013
- 2013-09-03 BR BR112016004723-0A patent/BR112016004723B1/pt active IP Right Grant
- 2013-09-03 JP JP2016537144A patent/JP6239118B2/ja active Active
- 2013-09-03 CN CN201380080517.XA patent/CN105793245B/zh active Active
- 2013-09-03 SG SG11201601503SA patent/SG11201601503SA/en unknown
- 2013-09-03 KR KR1020167007925A patent/KR102191084B1/ko active Active
- 2013-09-03 CA CA2941824A patent/CA2941824C/en active Active
- 2013-09-03 AU AU2013399913A patent/AU2013399913B2/en active Active
- 2013-09-03 WO PCT/EP2013/068198 patent/WO2015032423A1/en not_active Ceased
- 2013-09-03 RU RU2016111522A patent/RU2652795C2/ru active
- 2013-09-03 MX MX2016002738A patent/MX369974B/es active IP Right Grant
-
2016
- 2016-03-02 IL IL244380A patent/IL244380B/en active IP Right Grant
- 2016-03-29 ZA ZA2016/02047A patent/ZA201602047B/en unknown