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

2,4-диаминопиримидинови съединения, полезни като антисупресанти Download PDF

Info

Publication number: BG106695A
Authority: BG; Bulgaria
Prior art keywords: alkyl; aryl; heteroaryl; dihydro; amino
Prior art date: 1999-11-30

Application number

BG106695A

Other languages

Bulgarian (bg)

English (en)

Inventor

Todd Blumenkopf

Eileen Mueller

Eric ROSKAMP

Original Assignee

Pfizer Products Inc.

Priority date (The priority date 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 date listed.)

1999-11-30

Filing date

2002-05-13

Publication date

2002-12-29

2002-05-13 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2002-12-29 Publication of BG106695A publication Critical patent/BG106695A/bg

Links

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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- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Dermatology (AREA)
Hematology (AREA)
Neurology (AREA)
Endocrinology (AREA)
Rheumatology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Physical Education & Sports Medicine (AREA)
Oncology (AREA)
Transplantation (AREA)
Pain & Pain Management (AREA)
Obesity (AREA)
Orthopedic Medicine & Surgery (AREA)
Hospice & Palliative Care (AREA)
Emergency Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

BG106695A 1999-11-30 2002-05-13 2,4-диаминопиримидинови съединения, полезни като антисупресанти BG106695A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US16822499P	1999-11-30	1999-11-30
PCT/IB2000/001628 WO2001040215A1 (fr)	1999-11-30	2000-11-09	Composes de 2,4-diaminopyrimidine utilises comme immunodepresseurs

Publications (1)

Publication Number	Publication Date
BG106695A true BG106695A (bg)	2002-12-29

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ID=22610621

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG106695A BG106695A (bg)	1999-11-30	2002-05-13	2,4-диаминопиримидинови съединения, полезни като антисупресанти

Country Status (33)

Country	Link
EP (1)	EP1242403B1 (fr)
JP (1)	JP3955468B2 (fr)
KR (1)	KR20020059826A (fr)
CN (1)	CN1402720A (fr)
AP (1)	AP2002002530A0 (fr)
AT (1)	ATE315036T1 (fr)
AU (1)	AU1047601A (fr)
BG (1)	BG106695A (fr)
BR (1)	BR0015995A (fr)
CA (1)	CA2392971C (fr)
CO (1)	CO5261519A1 (fr)
CZ (1)	CZ20021703A3 (fr)
DE (1)	DE60025385T2 (fr)
EA (1)	EA200200411A1 (fr)
EE (1)	EE200200275A (fr)
ES (1)	ES2253266T3 (fr)
GT (1)	GT200000200A (fr)
HN (1)	HN2000000264A (fr)
HU (1)	HUP0203300A3 (fr)
IL (1)	IL149103A0 (fr)
IS (1)	IS6339A (fr)
MA (1)	MA26846A1 (fr)
MX (1)	MXPA02005350A (fr)
NO (1)	NO20022557D0 (fr)
OA (1)	OA12097A (fr)
PA (1)	PA8506801A1 (fr)
PE (1)	PE20010900A1 (fr)
PL (1)	PL355946A1 (fr)
SV (1)	SV2002000231A (fr)
TN (1)	TNSN00232A1 (fr)
TR (1)	TR200201431T2 (fr)
UY (1)	UY26455A1 (fr)
WO (1)	WO2001040215A1 (fr)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1257546A1 (fr) *	2000-02-17	2002-11-20	Amgen Inc.	Inhibiteurs de kinases
IL154016A0 (en) *	2000-08-31	2003-07-31	Pfizer Prod Inc	Pyrazole derivatives and their use as protein kinase inhibitors
US6660731B2 (en)	2000-09-15	2003-12-09	Vertex Pharmaceuticals Incorporated	Pyrazole compounds useful as protein kinase inhibitors
EP1317450B1 (fr)	2000-09-15	2006-11-22	Vertex Pharmaceuticals Incorporated	Composes de pyrazole utiles comme inhibiteurs de proteine kinase
US7473691B2 (en)	2000-09-15	2009-01-06	Vertex Pharmaceuticals Incorporated	Pyrazole compounds useful as protein kinase inhibitors
NZ526472A (en)	2000-12-21	2004-04-30	Vertex Pharma	Pyrazole compounds useful as protein kinase inhibitors
WO2003030909A1 (fr) *	2001-09-25	2003-04-17	Bayer Pharmaceuticals Corporation	2- et 4-aminopyrimidines n-substituees par un noyau bicyclique utilisees comme inhibiteurs de kinases dans le traitement du cancer
MY141867A (en)	2002-06-20	2010-07-16	Vertex Pharma	Substituted pyrimidines useful as protein kinase inhibitors
DK1532145T3 (da)	2002-08-02	2007-01-15	Vertex Pharma	Pyrazolpræparater der er anvendelige som inhibitorer af GSK-3
DE10237423A1 (de) *	2002-08-16	2004-02-19	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Verwendung von LCK-Inhibitoren für die Behandlung von immunologischen Erkrankungen
US20040204458A1 (en)	2002-08-16	2004-10-14	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Use of Lck inhibitors for treatment of immunologic diseases
BRPI0506839A (pt) *	2004-01-16	2007-06-12	Novartis Ag	composições e métodos para induzir a cardiomiogênese
US20060142348A1 (en) *	2004-10-12	2006-06-29	Decode Chemistry, Inc.	Aryl sulfonamide peri-substituted bicyclics for occlusive artery disease
US20060161001A1 (en) *	2004-12-20	2006-07-20	Amgen Inc.	Substituted heterocyclic compounds and methods of use
PE20060777A1 (es)	2004-12-24	2006-10-06	Boehringer Ingelheim Int	Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas
EP1954277B1 (fr)	2005-11-03	2017-01-18	Vertex Pharmaceuticals Incorporated	Aminopyrimidines utiles en tant qu'inhibiteurs de kinases
TW200804389A (en)	2006-02-14	2008-01-16	Vertex Pharma	Dihydrodiazepines useful as inhibitors of protein kinases
MX2008011661A (es) *	2006-03-16	2008-09-22	Novartis Ag	Compuestos organicos heterociclicos para el tratamiento de melanoma en particular.
US9096546B2 (en)	2007-05-10	2015-08-04	Albany Molecular Research, Inc.	Aryl- and heteroaryl-substituted tetrahydrobenzo-1,4-diazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
BRPI0818338A2 (pt) *	2007-10-16	2015-04-22	Daiichi Sankyo Co Ltd	Composto de pirimidil indolina
SG179206A1 (en)	2009-09-25	2012-04-27	Vertex Pharma	Methods for preparing pyrimidine derivatives useful as protein kinase inhibitors
CA2773827A1 (fr)	2009-09-25	2011-03-31	Vertex Pharmaceuticals Incorporated	Procede pour preparer des derives de pyrimidine utilises en tant qu'inhibiteurs de proteines kinases
TWI513694B (zh) *	2010-05-11	2015-12-21	Amgen Inc	抑制間變性淋巴瘤激酶的嘧啶化合物
KR101708761B1 (ko) *	2012-04-13	2017-02-21	주식회사 머쉬메드	퓨린 유도체 또는 그의 염을 포함하는 아토피성 피부염의 예방 또는 치료용 조성물
EP3055301B1 (fr) *	2013-10-07	2019-11-20	Kadmon Corporation, LLC	Dérivés de (2-(5-isoindolin-2-yl)pyrimidin-4-yl)-amine en tant qu'inhibiteurs de kinase rho pour le traitement de maladies auto-immunes
CN110582489B (zh) *	2017-06-30	2023-10-27	北京泰德制药股份有限公司	Rho相关蛋白激酶抑制剂、包含其的药物组合物及其制备方法和用途
WO2019000682A1 (fr) *	2017-06-30	2019-01-03	北京泰德制药股份有限公司	Inhibiteur de protéine kinase associée à rho, composition pharmaceutique contenant celui-ci, son procédé de préparation et ses applications
US10323023B2 (en)	2017-06-30	2019-06-18	Beijing Tide Pharmaceutical Co., Ltd.	Rho-associated protein kinase inhibitor, pharmaceutical composition comprising the same, as well as preparation method and use thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9523675D0 (en) *	1995-11-20	1996-01-24	Celltech Therapeutics Ltd	Chemical compounds
EP0837063A1 (fr) *	1996-10-17	1998-04-22	Pfizer Inc.	Dérivés de 4-aminoquinazoline
GB9905075D0 (en) *	1999-03-06	1999-04-28	Zeneca Ltd	Chemical compounds

2000
- 2000-11-09 TR TR2002/01431T patent/TR200201431T2/xx unknown
- 2000-11-09 CN CN00816506A patent/CN1402720A/zh active Pending
- 2000-11-09 JP JP2001541899A patent/JP3955468B2/ja not_active Expired - Fee Related
- 2000-11-09 BR BR0015995-6A patent/BR0015995A/pt not_active Application Discontinuation
- 2000-11-09 WO PCT/IB2000/001628 patent/WO2001040215A1/fr not_active Ceased
- 2000-11-09 KR KR1020027006941A patent/KR20020059826A/ko not_active Ceased
- 2000-11-09 CZ CZ20021703A patent/CZ20021703A3/cs unknown
- 2000-11-09 MX MXPA02005350A patent/MXPA02005350A/es active IP Right Grant
- 2000-11-09 EE EEP200200275A patent/EE200200275A/xx unknown
- 2000-11-09 ES ES00971650T patent/ES2253266T3/es not_active Expired - Lifetime
- 2000-11-09 OA OA1200200156A patent/OA12097A/en unknown
- 2000-11-09 IL IL14910300A patent/IL149103A0/xx unknown
- 2000-11-09 PL PL00355946A patent/PL355946A1/xx not_active Application Discontinuation
- 2000-11-09 AT AT00971650T patent/ATE315036T1/de not_active IP Right Cessation
- 2000-11-09 CA CA002392971A patent/CA2392971C/fr not_active Expired - Fee Related
- 2000-11-09 EP EP00971650A patent/EP1242403B1/fr not_active Expired - Lifetime
- 2000-11-09 DE DE60025385T patent/DE60025385T2/de not_active Expired - Lifetime
- 2000-11-09 AP APAP/P/2002/002530A patent/AP2002002530A0/en unknown
- 2000-11-09 AU AU10476/01A patent/AU1047601A/en not_active Abandoned
- 2000-11-09 HU HU0203300A patent/HUP0203300A3/hu unknown
- 2000-11-09 EA EA200200411A patent/EA200200411A1/ru unknown
- 2000-11-22 PA PA20008506801A patent/PA8506801A1/es unknown
- 2000-11-23 HN HN2000000264A patent/HN2000000264A/es unknown
- 2000-11-28 UY UY26455A patent/UY26455A1/es not_active Application Discontinuation
- 2000-11-28 PE PE2000001268A patent/PE20010900A1/es not_active Application Discontinuation
- 2000-11-29 GT GT200000200A patent/GT200000200A/es unknown
- 2000-11-29 SV SV2000000231A patent/SV2002000231A/es unknown
- 2000-11-29 TN TNTNSN00232A patent/TNSN00232A1/fr unknown
- 2000-11-30 CO CO00091745A patent/CO5261519A1/es unknown
2002
- 2002-04-12 IS IS6339A patent/IS6339A/is unknown
- 2002-05-13 BG BG106695A patent/BG106695A/bg unknown
- 2002-05-28 MA MA26655A patent/MA26846A1/fr unknown
- 2002-05-29 NO NO20022557A patent/NO20022557D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE60025385T2 (de)	2006-08-24
IS6339A (is)	2002-04-12
TNSN00232A1 (fr)	2005-11-10
AU1047601A (en)	2001-06-12
EA200200411A1 (ru)	2002-10-31
AP2002002530A0 (en)	2002-06-30
GT200000200A (es)	2002-05-23
SV2002000231A (es)	2002-07-16
OA12097A (en)	2006-05-04
ATE315036T1 (de)	2006-02-15
CN1402720A (zh)	2003-03-12
JP3955468B2 (ja)	2007-08-08
UY26455A1 (es)	2001-07-31
NO20022557L (no)	2002-05-29
CO5261519A1 (es)	2003-03-31
BR0015995A (pt)	2002-08-06
ES2253266T3 (es)	2006-06-01
PL355946A1 (en)	2004-05-31
TR200201431T2 (tr)	2002-09-23
CA2392971C (fr)	2008-10-07
KR20020059826A (ko)	2002-07-13
HN2000000264A (es)	2001-05-21
PE20010900A1 (es)	2001-09-08
EP1242403A1 (fr)	2002-09-25
NO20022557D0 (no)	2002-05-29
DE60025385D1 (de)	2006-03-30
IL149103A0 (en)	2002-11-10
HUP0203300A3 (en)	2003-10-28
CA2392971A1 (fr)	2001-06-07
WO2001040215A1 (fr)	2001-06-07
HUP0203300A2 (hu)	2003-02-28
CZ20021703A3 (cs)	2003-06-18
MXPA02005350A (es)	2002-12-11
EE200200275A (et)	2003-10-15
MA26846A1 (fr)	2004-12-20
JP2003515602A (ja)	2003-05-07
EP1242403B1 (fr)	2006-01-04
PA8506801A1 (es)	2002-04-25

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