BG106695A - 2,4-диаминопиримидинови съединения, полезни като антисупресанти - Google Patents

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Publication number

BG106695A

BG106695A BG106695A BG10669502A BG106695A BG 106695 A BG106695 A BG 106695A BG 106695 A BG106695 A BG 106695A BG 10669502 A BG10669502 A BG 10669502A BG 106695 A BG106695 A BG 106695A

Authority

BG

Bulgaria

Prior art keywords

alkyl

aryl

heteroaryl

dihydro

amino

Prior art date

1999-11-30

Links

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• Global Dossier
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• 239000003018 immunosuppressive agent Substances 0.000 title abstract 2
• 229960003444 immunosuppressant agent Drugs 0.000 title 1
• YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 121
• 238000000034 method Methods 0.000 claims abstract description 39
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 30
• 238000011282 treatment Methods 0.000 claims abstract description 29
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 28
• 150000003839 salts Chemical class 0.000 claims abstract description 24
• 230000001225 therapeutic effect Effects 0.000 claims abstract description 15
• 206010020751 Hypersensitivity Diseases 0.000 claims abstract description 14
• 208000026935 allergic disease Diseases 0.000 claims abstract description 13
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 12
• 206010052779 Transplant rejections Diseases 0.000 claims abstract description 11
• 230000007815 allergy Effects 0.000 claims abstract description 8
• 230000008901 benefit Effects 0.000 claims abstract description 5
• 239000012453 solvate Substances 0.000 claims abstract description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 4
• 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims abstract description 3
• -1 sulfonyl- Chemical group 0.000 claims description 381
• 125000000217 alkyl group Chemical group 0.000 claims description 184
• 125000001072 heteroaryl group Chemical group 0.000 claims description 164
• 125000003118 aryl group Chemical group 0.000 claims description 115
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 65
• 210000001744 T-lymphocyte Anatomy 0.000 claims description 54
• 125000004442 acylamino group Chemical group 0.000 claims description 54
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 46
• 125000002252 acyl group Chemical group 0.000 claims description 41
• 125000003545 alkoxy group Chemical group 0.000 claims description 38
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
• 241000124008 Mammalia Species 0.000 claims description 28
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
• 125000005843 halogen group Chemical group 0.000 claims description 26
• 125000004423 acyloxy group Chemical group 0.000 claims description 25
• 125000003282 alkyl amino group Chemical group 0.000 claims description 25
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
• 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 23
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 23
• 230000028993 immune response Effects 0.000 claims description 23
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
• 201000010099 disease Diseases 0.000 claims description 19
• 230000001404 mediated effect Effects 0.000 claims description 19
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 17
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 16
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 15
• 230000004913 activation Effects 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 14
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 13
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 13
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 10
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• 210000000987 immune system Anatomy 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 9
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 9
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
• 229910052805 deuterium Inorganic materials 0.000 claims description 8
• HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical compound C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 7
• 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
• HYTIPJFUWHYQON-UHFFFAOYSA-N 3,4-dihydro-1h-quinoxalin-2-one Chemical compound C1=CC=C2NC(=O)CNC2=C1 HYTIPJFUWHYQON-UHFFFAOYSA-N 0.000 claims description 5
• YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims description 5
• 206010042971 T-cell lymphoma Diseases 0.000 claims description 5
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 5
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
• 125000005110 aryl thio group Chemical group 0.000 claims description 5
• 230000001363 autoimmune Effects 0.000 claims description 5
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims description 4
• OZMQDKBUQORDIY-UHFFFAOYSA-N 6,7-dihydro-5h-[1,4]oxazino[3,2-e][1,2,4]triazine Chemical compound N1=CN=C2NCCOC2=N1 OZMQDKBUQORDIY-UHFFFAOYSA-N 0.000 claims description 4
• XOKMRXSMOHCNIX-UHFFFAOYSA-N 6-methyl-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(C)=CC=C21 XOKMRXSMOHCNIX-UHFFFAOYSA-N 0.000 claims description 4
• 201000004624 Dermatitis Diseases 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 208000000389 T-cell leukemia Diseases 0.000 claims description 4
• 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims description 4
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
• YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 claims description 4
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 230000033077 cellular process Effects 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 208000035475 disorder Diseases 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 4
• 206010025135 lupus erythematosus Diseases 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 3
• LYLJNZURWKWPIE-UHFFFAOYSA-N 4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)-n-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1CCC2=CC(C)=CC=C2N1C(N=1)=CC=NC=1NC1=CC=NN1C LYLJNZURWKWPIE-UHFFFAOYSA-N 0.000 claims description 3
• JJZFSQSMMSNIBX-UHFFFAOYSA-N 4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)-n-(3,4,5-trimethoxyphenyl)pyrimidin-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C=CN=2)N2C3=CC=C(C)C=C3CCC2)=C1 JJZFSQSMMSNIBX-UHFFFAOYSA-N 0.000 claims description 3
• CIWMFPQUMQBZQD-UHFFFAOYSA-N 4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)-n-(4-phenoxyphenyl)pyrimidin-2-amine Chemical compound C1CCC2=CC(C)=CC=C2N1C(N=1)=CC=NC=1NC(C=C1)=CC=C1OC1=CC=CC=C1 CIWMFPQUMQBZQD-UHFFFAOYSA-N 0.000 claims description 3
• ZDXWLBAKKLILBZ-UHFFFAOYSA-N 4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)-n-(5-methyl-1h-pyrazol-3-yl)pyrimidin-2-amine Chemical compound N1C(C)=CC(NC=2N=C(C=CN=2)N2C3=CC=C(C)C=C3CCC2)=N1 ZDXWLBAKKLILBZ-UHFFFAOYSA-N 0.000 claims description 3
• BKYRQBWAUMNUGT-UHFFFAOYSA-N 4-methyl-n-[4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)pyrimidin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2N=C(C=CN=2)N2C3=CC=C(C)C=C3CCC2)=N1 BKYRQBWAUMNUGT-UHFFFAOYSA-N 0.000 claims description 3
• IDAICLIJTRXNER-UHFFFAOYSA-N 5,6,7,8-tetrahydropteridine Chemical compound C1=NC=C2NCCNC2=N1 IDAICLIJTRXNER-UHFFFAOYSA-N 0.000 claims description 3
• NXQRMQIYCWFDGP-UHFFFAOYSA-N 5-fluoro-2,3-dihydro-1h-indole Chemical compound FC1=CC=C2NCCC2=C1 NXQRMQIYCWFDGP-UHFFFAOYSA-N 0.000 claims description 3
• BBIXEFQXHLVIPU-UHFFFAOYSA-N 6,7-dihydro-5h-pyrimido[4,5-b][1,4]oxazine Chemical compound C1=NC=C2NCCOC2=N1 BBIXEFQXHLVIPU-UHFFFAOYSA-N 0.000 claims description 3
• FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 claims description 3
• 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
• 208000010668 atopic eczema Diseases 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000000466 oxiranyl group Chemical group 0.000 claims description 3
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 238000011321 prophylaxis Methods 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000005493 quinolyl group Chemical group 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
• 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 2
• SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 claims description 2
• OTNXVGCVSNNWJP-UHFFFAOYSA-N 1-[4-(2,3-dihydro-1,4-benzoxazin-4-yl)pyrimidin-2-yl]-3-(2-ethoxyethyl)urea Chemical compound CCOCCNC(=O)NC1=NC=CC(N2C3=CC=CC=C3OCC2)=N1 OTNXVGCVSNNWJP-UHFFFAOYSA-N 0.000 claims description 2
• DOWDDIAXGSDKRE-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2h-1,5-naphthyridin-1-yl)pyrimidin-2-yl]-3-ethylurea Chemical compound CCNC(=O)NC1=NC=CC(N2C3=CC=CN=C3CCC2)=N1 DOWDDIAXGSDKRE-UHFFFAOYSA-N 0.000 claims description 2
• MRXFZNCDSQPGQQ-UHFFFAOYSA-N 1-cyclopentyl-n-[4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)pyrimidin-2-yl]indol-6-amine Chemical compound C1CCC2=CC(C)=CC=C2N1C(N=1)=CC=NC=1NC(C=C12)=CC=C1C=CN2C1CCCC1 MRXFZNCDSQPGQQ-UHFFFAOYSA-N 0.000 claims description 2
• LTWFBZQFHPDLNU-UHFFFAOYSA-N 2,3-dihydro-1h-pyrido[2,3-b][1,4]oxazine Chemical compound C1=CC=C2NCCOC2=N1 LTWFBZQFHPDLNU-UHFFFAOYSA-N 0.000 claims description 2
• AMSFZNPHLRKOIB-UHFFFAOYSA-N 2,3-dihydro-1h-pyrido[3,4-b][1,4]oxazine Chemical compound N1=CC=C2NCCOC2=C1 AMSFZNPHLRKOIB-UHFFFAOYSA-N 0.000 claims description 2
• ZFFYPGZDXUPKNK-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NCCC2=C1 ZFFYPGZDXUPKNK-UHFFFAOYSA-N 0.000 claims description 2
• JKWQHCSGMTWRIQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NCCC2=N1 JKWQHCSGMTWRIQ-UHFFFAOYSA-N 0.000 claims description 2
• UPZFJNRJKUKWGW-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[3,2-c]pyridine Chemical compound N1=CC=C2NCCC2=C1 UPZFJNRJKUKWGW-UHFFFAOYSA-N 0.000 claims description 2
• LIYRUQGPJLCBCT-UHFFFAOYSA-N 2-[[5-[[4-(2,3-dihydro-1,4-benzoxazin-4-yl)pyrimidin-2-yl]amino]pyridin-2-yl]-methylamino]ethanol Chemical compound C1=NC(N(CCO)C)=CC=C1NC1=NC=CC(N2C3=CC=CC=C3OCC2)=N1 LIYRUQGPJLCBCT-UHFFFAOYSA-N 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• YBBLSBDJIKMXNQ-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzothiazine Chemical compound C1=CC=C2NCCSC2=C1 YBBLSBDJIKMXNQ-UHFFFAOYSA-N 0.000 claims description 2
• TTXQBUSUPRNFFS-UHFFFAOYSA-N 3,4-dihydro-2h-pyridazino[4,5-b][1,4]thiazine Chemical compound N1=NC=C2NCCSC2=C1 TTXQBUSUPRNFFS-UHFFFAOYSA-N 0.000 claims description 2
• ZBGZYJMISPILCN-UHFFFAOYSA-N 3-chloro-n-[4-(4-methyl-3-oxo-2h-quinoxalin-1-yl)pyrimidin-2-yl]benzamide Chemical compound C12=CC=CC=C2N(C)C(=O)CN1C(N=1)=CC=NC=1NC(=O)C1=CC=CC(Cl)=C1 ZBGZYJMISPILCN-UHFFFAOYSA-N 0.000 claims description 2
• MJKCEYKWMUYHCC-UHFFFAOYSA-N 3-cyano-n-[4-(7-methoxy-2,3,4,5-tetrahydro-1-benzazepin-1-yl)pyrimidin-2-yl]benzamide Chemical compound C1CCCC2=CC(OC)=CC=C2N1C(N=1)=CC=NC=1NC(=O)C1=CC=CC(C#N)=C1 MJKCEYKWMUYHCC-UHFFFAOYSA-N 0.000 claims description 2
• YDFLWMZZUDUZSP-UHFFFAOYSA-N 4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)-n-(6-morpholin-4-ylpyridin-3-yl)pyrimidin-2-amine Chemical compound C1CCC2=CC(C)=CC=C2N1C(N=1)=CC=NC=1NC(C=N1)=CC=C1N1CCOCC1 YDFLWMZZUDUZSP-UHFFFAOYSA-N 0.000 claims description 2
• RESLQPCPXRNZEV-UHFFFAOYSA-N 4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)-n-phenylpyrimidin-2-amine Chemical compound C1CCC2=CC(C)=CC=C2N1C(N=1)=CC=NC=1NC1=CC=CC=C1 RESLQPCPXRNZEV-UHFFFAOYSA-N 0.000 claims description 2
• FDPXDNMKJARKDN-UHFFFAOYSA-N 4-benzyl-3-n-[4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)pyrimidin-2-yl]-1h-pyrazole-3,5-diamine Chemical compound C1CCC2=CC(C)=CC=C2N1C(N=1)=CC=NC=1NC1=NNC(N)=C1CC1=CC=CC=C1 FDPXDNMKJARKDN-UHFFFAOYSA-N 0.000 claims description 2
• OXNZWCYNCDWCJA-UHFFFAOYSA-N 4-methyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2C(C)CCNC2=C1 OXNZWCYNCDWCJA-UHFFFAOYSA-N 0.000 claims description 2
• PWFXESTVPWRTTI-UHFFFAOYSA-N 5,6,7,8-tetrahydropyrido[2,3-b]pyrazine Chemical compound C1=CN=C2CCCNC2=N1 PWFXESTVPWRTTI-UHFFFAOYSA-N 0.000 claims description 2
• MWCDUUXVWLNERN-UHFFFAOYSA-N 5-[[4-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)pyrimidin-2-yl]amino]-1,3-dihydrobenzimidazol-2-one Chemical compound C1=C2NC(=O)NC2=CC(NC=2N=CC=C(N=2)N2C3=CC=C(C=C3CCC2)C)=C1 MWCDUUXVWLNERN-UHFFFAOYSA-N 0.000 claims description 2
• XDQBRWLQHZVTKL-UHFFFAOYSA-N 6,7-dihydro-5h-[1,4]oxazino[2,3-d]triazine Chemical compound N1=NC=C2NCCOC2=N1 XDQBRWLQHZVTKL-UHFFFAOYSA-N 0.000 claims description 2
• PRPMXLNAVXTDQS-UHFFFAOYSA-N 6,7-dihydro-5h-pyridazino[3,4-b][1,4]oxazine Chemical compound N1=CC=C2NCCOC2=N1 PRPMXLNAVXTDQS-UHFFFAOYSA-N 0.000 claims description 2
• QYFIDSDMVGCTHS-UHFFFAOYSA-N 6,7-dihydro-5h-pyridazino[3,4-b][1,4]thiazine Chemical compound N1=CC=C2NCCSC2=N1 QYFIDSDMVGCTHS-UHFFFAOYSA-N 0.000 claims description 2
• GKMCSBGMOFNEFK-UHFFFAOYSA-N 6,7-dihydro-5h-pyrimido[4,5-b][1,4]thiazine Chemical compound C1=NC=C2NCCSC2=N1 GKMCSBGMOFNEFK-UHFFFAOYSA-N 0.000 claims description 2
• LMAYDNVIKBCSLP-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NCCC2=N1 LMAYDNVIKBCSLP-UHFFFAOYSA-N 0.000 claims description 2
• JVGAECUUHSRREW-UHFFFAOYSA-N 7,8-dihydro-6h-[1,4]oxazino[3,2-d]triazine Chemical compound N1=NN=C2NCCOC2=C1 JVGAECUUHSRREW-UHFFFAOYSA-N 0.000 claims description 2
• UCJLLMLOHWXKRP-UHFFFAOYSA-N 7,8-dihydro-6h-pyridazino[4,3-b][1,4]thiazine Chemical compound C1=NN=C2NCCSC2=C1 UCJLLMLOHWXKRP-UHFFFAOYSA-N 0.000 claims description 2
• VJYKVOPUYLLKLO-UHFFFAOYSA-N 7,8-dihydro-6h-pyrimido[5,4-b][1,4]oxazine Chemical compound N1=CN=C2NCCOC2=C1 VJYKVOPUYLLKLO-UHFFFAOYSA-N 0.000 claims description 2
• WVEIRFXVLXAKLS-UHFFFAOYSA-N 7-chloro-1,2,3,4-tetrahydroquinoline Chemical compound C1CCNC2=CC(Cl)=CC=C21 WVEIRFXVLXAKLS-UHFFFAOYSA-N 0.000 claims description 2
• NLSDMOYGCYVCFC-UHFFFAOYSA-N 8-chloro-1,2,3,4-tetrahydroquinoline Chemical compound C1CCNC2=C1C=CC=C2Cl NLSDMOYGCYVCFC-UHFFFAOYSA-N 0.000 claims description 2
• YIIPMCFBCZKCFB-UHFFFAOYSA-N 8-methyl-1,2,3,4-tetrahydroquinoline Chemical compound C1CCNC2=C1C=CC=C2C YIIPMCFBCZKCFB-UHFFFAOYSA-N 0.000 claims description 2
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
• LPCWKMYWISGVSK-UHFFFAOYSA-N bicyclo[3.2.1]octane Chemical compound C1C2CCC1CCC2 LPCWKMYWISGVSK-UHFFFAOYSA-N 0.000 claims description 2
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