NO324934B1 - Pyrrolo[2,3-d]pyramidinforbindelser som immunosuppresive midler - Google Patents

Info

Publication number

NO324934B1

NO324934B1 NO20026030A NO20026030A NO324934B1 NO 324934 B1 NO324934 B1 NO 324934B1 NO 20026030 A NO20026030 A NO 20026030A NO 20026030 A NO20026030 A NO 20026030A NO 324934 B1 NO324934 B1 NO 324934B1

Authority

NO

Norway

Prior art keywords

methyl

alkyl

amino

pyrrolo

pyrimidin

Prior art date

2000-06-26

Links

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• 239000003018 immunosuppressive agent Substances 0.000 title description 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
• 229960003444 immunosuppressant agent Drugs 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims description 135
• 150000001875 compounds Chemical class 0.000 claims description 122
• -1 hydroxy, amino Chemical group 0.000 claims description 86
• 150000003839 salts Chemical class 0.000 claims description 36
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 32
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 24
• 108010019421 Janus Kinase 3 Proteins 0.000 claims description 24
• 102000006500 Janus Kinase 3 Human genes 0.000 claims description 24
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 19
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 15
• 125000004442 acylamino group Chemical group 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
• 229910052805 deuterium Inorganic materials 0.000 claims description 14
• JHQOCEWOJAFCTJ-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidine-1-carboxylic acid Chemical compound CC1CCN(C(O)=O)CC1N(C)C1=NC=NC2=C1C=CN2 JHQOCEWOJAFCTJ-UHFFFAOYSA-N 0.000 claims description 13
• 125000003282 alkyl amino group Chemical group 0.000 claims description 13
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 12
• 125000002252 acyl group Chemical group 0.000 claims description 10
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 10
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 208000035475 disorder Diseases 0.000 claims description 9
• 125000004423 acyloxy group Chemical group 0.000 claims description 8
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 7
• 102000001253 Protein Kinase Human genes 0.000 claims description 7
• 208000006673 asthma Diseases 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 230000005764 inhibitory process Effects 0.000 claims description 7
• 108060006633 protein kinase Proteins 0.000 claims description 7
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 208000023275 Autoimmune disease Diseases 0.000 claims description 6
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 6
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 208000024799 Thyroid disease Diseases 0.000 claims description 6
• 206010052779 Transplant rejections Diseases 0.000 claims description 6
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 201000008937 atopic dermatitis Diseases 0.000 claims description 6
• 230000001363 autoimmune Effects 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 208000032839 leukemia Diseases 0.000 claims description 6
• 206010025135 lupus erythematosus Diseases 0.000 claims description 6
• 201000006417 multiple sclerosis Diseases 0.000 claims description 6
• 210000000056 organ Anatomy 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 6
• 238000002689 xenotransplantation Methods 0.000 claims description 6
• RDGVREXPTVNIOZ-UHFFFAOYSA-N (3-hydroxypyrrolidin-1-yl)-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]methanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)N1CCC(O)C1 RDGVREXPTVNIOZ-UHFFFAOYSA-N 0.000 claims description 5
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 5
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 210000000987 immune system Anatomy 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• KNRLJPBXCVZFKC-UHFFFAOYSA-N 1-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-2-(tetrazol-1-yl)ethanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)CN1C=NN=N1 KNRLJPBXCVZFKC-UHFFFAOYSA-N 0.000 claims description 4
• YXPJSLNLGWWFQK-UHFFFAOYSA-N 4-[[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]methyl]benzenesulfonamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1CC1=CC=C(S(N)(=O)=O)C=C1 YXPJSLNLGWWFQK-UHFFFAOYSA-N 0.000 claims description 4
• BXLOTZYFEBJGFO-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-(1,2-oxazol-3-yl)piperidine-1-carboxamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC=1C=CON=1 BXLOTZYFEBJGFO-UHFFFAOYSA-N 0.000 claims description 4
• 208000011231 Crohn disease Diseases 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
• 125000005157 alkyl carboxy group Chemical group 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000001769 aryl amino group Chemical group 0.000 claims description 4
• 125000005110 aryl thio group Chemical group 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• WCEMRCSQVJUUEL-UHFFFAOYSA-N 2-cyclopropyl-1-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]ethanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)CC1CC1 WCEMRCSQVJUUEL-UHFFFAOYSA-N 0.000 claims description 3
• XLWYJSMYNALODL-UHFFFAOYSA-N 3-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidine-1-carbonyl]cyclopentan-1-one Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)C1CCC(=O)C1 XLWYJSMYNALODL-UHFFFAOYSA-N 0.000 claims description 3
• TXZVMZALSHPMNV-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-(1,3-thiazol-2-yl)piperidine-1-carboxamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=NC=CS1 TXZVMZALSHPMNV-UHFFFAOYSA-N 0.000 claims description 3
• XZXYNRDSRVDEFY-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-(3-methyl-1,2-thiazol-5-yl)piperidine-1-carboxamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=CC(C)=NS1 XZXYNRDSRVDEFY-UHFFFAOYSA-N 0.000 claims description 3
• JNDULUJHHAKHFI-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-(4-methylsulfonylphenyl)piperidine-1-carboxamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=CC=C(S(C)(=O)=O)C=C1 JNDULUJHHAKHFI-UHFFFAOYSA-N 0.000 claims description 3
• BAMSJXFWGUSAPN-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-(4-nitrophenyl)piperidine-1-carboxamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=CC=C([N+]([O-])=O)C=C1 BAMSJXFWGUSAPN-UHFFFAOYSA-N 0.000 claims description 3
• MNZUYWZVJCMTLM-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-(4-sulfamoylphenyl)piperidine-1-carboxamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1 MNZUYWZVJCMTLM-UHFFFAOYSA-N 0.000 claims description 3
• KSZRXZRZFBENAS-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-[4-(methylsulfamoyl)phenyl]piperidine-1-carboxamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1NC(=O)N1CC(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CC1 KSZRXZRZFBENAS-UHFFFAOYSA-N 0.000 claims description 3
• HIOUMGNWXIKDEL-UHFFFAOYSA-N 4-methyl-n-(3-methyl-1,2-oxazol-4-yl)-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidine-1-carboxamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=CON=C1C HIOUMGNWXIKDEL-UHFFFAOYSA-N 0.000 claims description 3
• NHFAFANWNRBBTO-UHFFFAOYSA-N 5-[2-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-2-oxoethyl]-1,3-thiazolidine-2,4-dione Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)CC1SC(=O)NC1=O NHFAFANWNRBBTO-UHFFFAOYSA-N 0.000 claims description 3
• IGNOXKOLEZVMMV-UHFFFAOYSA-N [4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-(oxolan-3-yl)methanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)C1CCOC1 IGNOXKOLEZVMMV-UHFFFAOYSA-N 0.000 claims description 3
• IKJVHXOXTUJMHW-UHFFFAOYSA-N cyclopentyl-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]methanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)C1CCCC1 IKJVHXOXTUJMHW-UHFFFAOYSA-N 0.000 claims description 3
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• WYAWBXYGRGZLTM-UHFFFAOYSA-N n-methyl-n-[4-methyl-1-(5-nitropyridin-2-yl)piperidin-3-yl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C1=CC=C([N+]([O-])=O)C=N1 WYAWBXYGRGZLTM-UHFFFAOYSA-N 0.000 claims description 3
• 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 2
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