JP2020529987A5 - - Google Patents
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- JP2020529987A5 JP2020529987A5 JP2020505224A JP2020505224A JP2020529987A5 JP 2020529987 A5 JP2020529987 A5 JP 2020529987A5 JP 2020505224 A JP2020505224 A JP 2020505224A JP 2020505224 A JP2020505224 A JP 2020505224A JP 2020529987 A5 JP2020529987 A5 JP 2020529987A5
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- JP
- Japan
- Prior art keywords
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- pharmaceutically acceptable
- acceptable salt
- alkyl
- compound according
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000013078 crystal Substances 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims description 28
- 206010009887 colitis Diseases 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 208000015943 Coeliac disease Diseases 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 201000004624 Dermatitis Diseases 0.000 claims description 6
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 201000007241 cutaneous T cell lymphoma Diseases 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 6
- 201000005962 mycosis fungoides Diseases 0.000 claims description 6
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 6
- 208000009137 Behcet syndrome Diseases 0.000 claims description 5
- 239000012275 CTLA-4 inhibitor Substances 0.000 claims description 5
- 229940045513 CTLA4 antagonist Drugs 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 206010058838 Enterocolitis infectious Diseases 0.000 claims description 5
- 206010064212 Eosinophilic oesophagitis Diseases 0.000 claims description 5
- 229940076838 Immune checkpoint inhibitor Drugs 0.000 claims description 5
- 102000037984 Inhibitory immune checkpoint proteins Human genes 0.000 claims description 5
- 108091008026 Inhibitory immune checkpoint proteins Proteins 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 201000000708 eosinophilic esophagitis Diseases 0.000 claims description 5
- 208000009326 ileitis Diseases 0.000 claims description 5
- 239000012274 immune-checkpoint protein inhibitor Substances 0.000 claims description 5
- 208000027139 infectious colitis Diseases 0.000 claims description 5
- 210000004698 lymphocyte Anatomy 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QPEJAHMNOVMSOZ-UHFFFAOYSA-N 2-azaspiro[3.3]heptane Chemical compound C1CCC21CNC2 QPEJAHMNOVMSOZ-UHFFFAOYSA-N 0.000 claims description 2
- DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical compound C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims 2
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims 2
- 238000011257 definitive treatment Methods 0.000 claims 1
- -1 1,2 - difluoro ethyl Chemical group 0.000 description 33
- 239000000243 solution Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 3
- 206010067472 Organising pneumonia Diseases 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 201000009805 cryptogenic organizing pneumonia Diseases 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 230000000414 obstructive effect Effects 0.000 description 3
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- KKGNNTRMDRNYDJ-SMMXGFFBSA-N (E)-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enoic acid Chemical compound CN1CCC[C@@H]1\C=C\C(O)=O KKGNNTRMDRNYDJ-SMMXGFFBSA-N 0.000 description 2
- 0 *CC(CCCCCCN*I)IC(c1c(*)[n]nc1)=*C(c(cc1*)ccc1O)=I Chemical compound *CC(CCCCCCN*I)IC(c1c(*)[n]nc1)=*C(c(cc1*)ccc1O)=I 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- 201000003883 Cystic fibrosis Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 239000007821 HATU Substances 0.000 description 2
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 229960000556 fingolimod Drugs 0.000 description 2
- KKGQTZUTZRNORY-UHFFFAOYSA-N fingolimod Chemical compound CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 KKGQTZUTZRNORY-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
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- 229960003433 thalidomide Drugs 0.000 description 2
- QLJYLJGYIDIJPT-VIFPVBQESA-N (2s)-3-(4-aminophenyl)-2-methoxypropanoic acid Chemical compound CO[C@H](C(O)=O)CC1=CC=C(N)C=C1 QLJYLJGYIDIJPT-VIFPVBQESA-N 0.000 description 1
- KSELABKNBIUMGG-YGBAREPYSA-N (2z,3ar,4r,5r,6as)-3,3-difluoro-4-[(e,3r,4r)-3-hydroxy-4-(3-methylphenyl)pent-1-enyl]-2-[4-(2h-tetrazol-5-yl)butylidene]-4,5,6,6a-tetrahydro-3ah-cyclopenta[b]furan-5-ol Chemical compound O([C@H]1C[C@@H](O)[C@@H]([C@H]1C1(F)F)/C=C/[C@@H](O)[C@H](C)C=2C=C(C)C=CC=2)\C1=C/CCCC=1N=NNN=1 KSELABKNBIUMGG-YGBAREPYSA-N 0.000 description 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- MVGWUTBTXDYMND-QGZVFWFLSA-N 2-[(3r)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C([C@@H]1CC(=O)O)CC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 MVGWUTBTXDYMND-QGZVFWFLSA-N 0.000 description 1
- CAOTVXGYTWCKQE-UHFFFAOYSA-N 3-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)-1-adamantanecarboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCC=4C=CN=CC=4)CC2CC3C1 CAOTVXGYTWCKQE-UHFFFAOYSA-N 0.000 description 1
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| WO2018004306A1 (en) | 2016-06-30 | 2018-01-04 | Daewoong Pharmaceutical Co., Ltd. | Pyrazolopyrimidine derivatives as kinase inhibitor |
| EP3509572A4 (en) | 2016-09-08 | 2020-05-13 | Synergistic Therapeutics, LLC | TOPICAL FORMULATION FOR HAIR GROWTH |
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| KR102032418B1 (ko) * | 2017-06-15 | 2019-10-16 | 한국화학연구원 | 접합 피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 포함하는 브루톤티로신 키나제 활성 관련 질환의 예방 또는 치료용 약학적 조성물 |
| BR112020002265A2 (pt) | 2017-08-01 | 2020-07-28 | Theravance Biopharma R&D Ip, Llc | compostos pirazólicos e triazólicos bicíclicos como inibidores de jak quiinase |
| US10981906B2 (en) | 2017-11-03 | 2021-04-20 | Aclaris Therapeutics, Inc. | Substituted pyrrolopyridine JAK inhibitors and methods of making and using the same |
| KR102577241B1 (ko) | 2017-12-28 | 2023-09-11 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 아미노-플루오로피페리딘 유도체 |
| IL275207B (en) | 2017-12-28 | 2022-09-01 | Daewoong Pharmaceutical Co Ltd | An oxy-fluoropiperidine derivative as a kinase inhibitor |
| KR102577242B1 (ko) | 2017-12-28 | 2023-09-11 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 아미노-메틸피페리딘 유도체 |
| JP2022518741A (ja) * | 2019-01-23 | 2022-03-16 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | ＪＡＫキナーゼ阻害剤としてのイミダゾ［１，５－ａ］ピリジン、１，２，４－トリアゾロ［４，３－ａ］ピリジンおよびイミダゾ［１，５－ａ］ピラジン |
| US11471442B2 (en) * | 2020-05-14 | 2022-10-18 | Theravance Biopharma R&D Ip, Llc | Administration of gut-selective JAK3 inhibitor |
-
2018
- 2018-07-31 BR BR112020002265-9A patent/BR112020002265A2/pt not_active Application Discontinuation
- 2018-07-31 US US16/050,227 patent/US10392368B2/en active Active
- 2018-07-31 TW TW107126579A patent/TW201920150A/zh unknown
- 2018-07-31 SG SG11202000602YA patent/SG11202000602YA/en unknown
- 2018-07-31 JP JP2020505224A patent/JP7098716B2/ja active Active
- 2018-07-31 EA EA202090413A patent/EA038912B1/ru unknown
- 2018-07-31 MY MYPI2020000251A patent/MY200629A/en unknown
- 2018-07-31 WO PCT/US2018/044508 patent/WO2019027960A1/en not_active Ceased
- 2018-07-31 AU AU2018312349A patent/AU2018312349A1/en not_active Abandoned
- 2018-07-31 KR KR1020207005956A patent/KR20200036004A/ko not_active Withdrawn
- 2018-07-31 UA UAA202001352A patent/UA125318C2/uk unknown
- 2018-07-31 MX MX2020001170A patent/MX2020001170A/es unknown
- 2018-07-31 AR ARP180102151 patent/AR112348A1/es unknown
- 2018-07-31 CN CN201880050675.3A patent/CN111032646B/zh not_active Expired - Fee Related
- 2018-07-31 PE PE2020000171A patent/PE20201028A1/es unknown
- 2018-07-31 EP EP18755621.2A patent/EP3652169A1/en not_active Withdrawn
- 2018-07-31 MA MA049570A patent/MA49570A/fr unknown
- 2018-07-31 CA CA3069990A patent/CA3069990A1/en not_active Abandoned
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2019
- 2019-06-28 US US16/456,179 patent/US10538513B2/en active Active
- 2019-11-19 US US16/688,109 patent/US10968205B2/en not_active Expired - Fee Related
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2020
- 2020-01-14 IL IL272031A patent/IL272031A/en unknown
- 2020-01-27 PH PH12020500201A patent/PH12020500201A1/en unknown
- 2020-01-28 ZA ZA2020/00561A patent/ZA202000561B/en unknown
- 2020-01-31 CL CL2020000283A patent/CL2020000283A1/es unknown
- 2020-02-11 CO CONC2020/0001469A patent/CO2020001469A2/es unknown
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2021
- 2021-02-22 US US17/249,128 patent/US20220119369A1/en not_active Abandoned
- 2021-03-17 JP JP2021043173A patent/JP2021098751A/ja not_active Withdrawn
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