BG107236A - ПИРОЛО[2,3-d] ПИРИМИДИНОВИ СЪЕДИНЕНИЯ КАТО ИМУНОДЕПРЕСИВНИ СРЕДСТВА - Google Patents

ПИРОЛО[2,3-d] ПИРИМИДИНОВИ СЪЕДИНЕНИЯ КАТО ИМУНОДЕПРЕСИВНИ СРЕДСТВА Download PDF

Info

Publication number: BG107236A
Authority: BG; Bulgaria
Prior art keywords: methyl; alkyl; amino; pyrimidin; pyrrolo
Prior art date: 2000-06-26

Application number

BG107236A

Other languages

Bulgarian (bg)

English (en)

Inventor

Todd Blumenkopf

Mark Flanagan

Michael MUNCHHOF

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.)

2000-06-26

Filing date

2002-10-31

Publication date

2003-09-30

2002-10-31 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2003-09-30 Publication of BG107236A publication Critical patent/BG107236A/bg

Links

CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 9
229940125721 immunosuppressive agent Drugs 0.000 title description 2
239000003018 immunosuppressive agent Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 149
108010019421 Janus Kinase 3 Proteins 0.000 claims abstract description 25
102000006500 Janus Kinase 3 Human genes 0.000 claims abstract description 25
102000001253 Protein Kinase Human genes 0.000 claims abstract description 7
108060006633 protein kinase Proteins 0.000 claims abstract description 7
-1 nitro-C 1 -C 6 alkyl Chemical group 0.000 claims description 156
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 111
125000000217 alkyl group Chemical group 0.000 claims description 83
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 59
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 53
150000003839 salts Chemical class 0.000 claims description 34
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
125000001072 heteroaryl group Chemical group 0.000 claims description 24
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
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 22
125000003118 aryl group Chemical group 0.000 claims description 22
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
125000003277 amino group Chemical group 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
125000003282 alkyl amino group Chemical group 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 14
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 14
125000004442 acylamino group Chemical group 0.000 claims description 13
201000010099 disease Diseases 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 11
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 10
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
229910052805 deuterium Inorganic materials 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
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 7
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
230000005764 inhibitory process Effects 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
208000023275 Autoimmune disease Diseases 0.000 claims description 5
206010009900 Colitis ulcerative Diseases 0.000 claims description 5
206010028980 Neoplasm Diseases 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 5
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 5
208000010928 autoimmune thyroid disease Diseases 0.000 claims description 5
201000011510 cancer Diseases 0.000 claims description 5
206010012601 diabetes mellitus Diseases 0.000 claims description 5
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 5
206010025135 lupus erythematosus Diseases 0.000 claims description 5
201000006417 multiple sclerosis Diseases 0.000 claims description 5
210000000056 organ Anatomy 0.000 claims description 5
206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000011231 Crohn disease Diseases 0.000 claims description 4
206010012434 Dermatitis allergic Diseases 0.000 claims description 4
206010052779 Transplant rejections Diseases 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000001769 aryl amino group Chemical group 0.000 claims description 4
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 4
125000005110 aryl thio group Chemical group 0.000 claims description 4
201000008937 atopic dermatitis Diseases 0.000 claims description 4
208000010668 atopic eczema Diseases 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
210000000987 immune system Anatomy 0.000 claims description 4
208000032839 leukemia Diseases 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
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 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
125000006528 (C2-C6) alkyl group Chemical group 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
229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
239000002260 anti-inflammatory agent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 2
JTRGLKTYLIFFTR-UHFFFAOYSA-N 2-[4-[[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidine-1-carbonyl]amino]phenyl]acetic acid Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=CC=C(CC(O)=O)C=C1 JTRGLKTYLIFFTR-UHFFFAOYSA-N 0.000 claims description 2
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 2
WQXRYEVRJRVDSK-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-(4-methyl-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(C)=CS1 WQXRYEVRJRVDSK-UHFFFAOYSA-N 0.000 claims description 2
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 2
BIZBPVFLUUDEQH-UHFFFAOYSA-N [4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-(1,3-thiazolidin-3-yl)methanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)N1CCSC1 BIZBPVFLUUDEQH-UHFFFAOYSA-N 0.000 claims description 2
RONMOMUOZGIDET-UHFFFAOYSA-N [4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-pyrrolidin-1-ylmethanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)N1CCCC1 RONMOMUOZGIDET-UHFFFAOYSA-N 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
LRIZCRLAGSEHSM-UHFFFAOYSA-N n,n,4-trimethyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidine-1-carboxamide Chemical compound CC1CCN(C(=O)N(C)C)CC1N(C)C1=NC=NC2=C1C=CN2 LRIZCRLAGSEHSM-UHFFFAOYSA-N 0.000 claims description 2
GHYWHYHXKQASKQ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)piperidine-1-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)N1CCCCC1 GHYWHYHXKQASKQ-UHFFFAOYSA-N 0.000 claims description 2
PJIDNSQIATYRAD-UHFFFAOYSA-N n-(6-cyanopyridin-3-yl)-4-methyl-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=CC=C(C#N)N=C1 PJIDNSQIATYRAD-UHFFFAOYSA-N 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 9
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims 2
125000005157 alkyl carboxy group Chemical group 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims 1
125000006530 (C4-C6) alkyl group Chemical group 0.000 claims 1
HJWUCTNLSFICSW-UHFFFAOYSA-N 2-[2-[[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidine-1-carbonyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=NC(CC(O)=O)=CS1 HJWUCTNLSFICSW-UHFFFAOYSA-N 0.000 claims 1
JAUIMPSXWZMZOR-UHFFFAOYSA-N 2-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-1,3-thiazol-5-amine Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C1=NC=C(N)S1 JAUIMPSXWZMZOR-UHFFFAOYSA-N 0.000 claims 1
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 1
HHNBSQGOZVNGPL-UHFFFAOYSA-N N-(1,3-thiazol-2-yl)piperidine-1-carboxamide Chemical compound S1C(=NC=C1)NC(=O)N1CCCCC1 HHNBSQGOZVNGPL-UHFFFAOYSA-N 0.000 claims 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
229920001577 copolymer Chemical group 0.000 claims 1
JPWQXLMZEXLCHO-UHFFFAOYSA-N n-[4-(methylsulfamoyl)phenyl]piperidine-1-carboxamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1NC(=O)N1CCCCC1 JPWQXLMZEXLCHO-UHFFFAOYSA-N 0.000 claims 1
YDALXWLQBQYZST-UHFFFAOYSA-N n-benzyl-n,4-dimethyl-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)N(C)CC1=CC=CC=C1 YDALXWLQBQYZST-UHFFFAOYSA-N 0.000 claims 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
238000000034 method Methods 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
239000000203 mixture Substances 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
238000002360 preparation method Methods 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 20
239000002253 acid Substances 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 13
239000000047 product Substances 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 10
108010036949 Cyclosporine Proteins 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 10
239000002904 solvent Substances 0.000 description 10
108010002350 Interleukin-2 Proteins 0.000 description 9
102000000588 Interleukin-2 Human genes 0.000 description 9
239000002585 base Substances 0.000 description 9
230000000903 blocking effect Effects 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
239000010410 layer Substances 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 6
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 6
230000001419 dependent effect Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000000651 prodrug Substances 0.000 description 6
229940002612 prodrug Drugs 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000000443 aerosol Substances 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
AXWBJJJQRJBTMI-UHFFFAOYSA-N n-methyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CNC1=NC=NC2=C1C=CN2 AXWBJJJQRJBTMI-UHFFFAOYSA-N 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
230000035755 proliferation Effects 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
PEHVGBZKEYRQSX-UHFFFAOYSA-N 7-deaza-adenine Chemical compound NC1=NC=NC2=C1C=CN2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 description 4
229930105110 Cyclosporin A Natural products 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
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Classifications

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BG107236A 2000-06-26 2002-10-31 ПИРОЛО[2,3-d] ПИРИМИДИНОВИ СЪЕДИНЕНИЯ КАТО ИМУНОДЕПРЕСИВНИ СРЕДСТВА BG107236A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US21428700P	2000-06-26	2000-06-26
PCT/IB2001/000975 WO2002000661A1 (en)	2000-06-26	2001-06-05	PYRROLO[2,3-d]PYRIMIDINE COMPOUNDS AS IMMUNOSUPPRESSIVE AGENTS

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BG107236A true BG107236A (bg)	2003-09-30

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US (4)	US6696567B2 (ja)
EP (2)	EP1294724B1 (ja)
JP (1)	JP4068958B2 (ja)
KR (1)	KR100516419B1 (ja)
CN (1)	CN100351253C (ja)
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AR (1)	AR029279A1 (ja)
AT (2)	ATE423120T1 (ja)
AU (1)	AU784297C (ja)
BG (1)	BG107236A (ja)
BR (1)	BR0111561A (ja)
CA (1)	CA2412560C (ja)
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CZ (1)	CZ20023993A3 (ja)
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PT (1)	PT1294724E (ja)
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UA (1)	UA74370C2 (ja)
WO (1)	WO2002000661A1 (ja)
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ZA (1)	ZA200210275B (ja)

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HUP0102574A3 (en) *	1998-06-19	2002-01-28	Pfizer Prod Inc	Pyrrolo[2,3-d]pyrimidine compounds
PA8474101A1 (es)	1998-06-19	2000-09-29	Pfizer Prod Inc	Compuestos de pirrolo [2,3-d] pirimidina
ATE494388T1 (de)	1999-01-13	2011-01-15	Univ New York State Res Found	Neues verfahren zum erschaffen von proteinkinase- inhibitoren
NZ518884A (en)	1999-12-10	2004-02-27	Pfizer Prod Inc	Pyrrolo[2,3-d]pyrimidine compounds
US7301023B2 (en) *	2001-05-31	2007-11-27	Pfizer Inc.	Chiral salt resolution
US7005445B2 (en)	2001-10-22	2006-02-28	The Research Foundation Of State University Of New York	Protein kinase and phosphatase inhibitors and methods for designing them
CA2464214C (en) *	2001-10-22	2011-02-08	The Research Foundation Of State University Of New York	Protein kinase and phosphatase inhibitors, methods for designing them, and methods of using them
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Also Published As

Publication number	Publication date
US6962993B2 (en)	2005-11-08
KR100516419B1 (ko)	2005-09-23
PE20020381A1 (es)	2002-05-13
TNSN01095A1 (fr)	2005-11-10
DK1686130T3 (da)	2009-04-06
US20020068746A1 (en)	2002-06-06
CN1439010A (zh)	2003-08-27
MA26917A1 (fr)	2004-12-20
US20050197349A1 (en)	2005-09-08
WO2002000661A1 (en)	2002-01-03
NZ522364A (en)	2004-09-24
HUP0301114A3 (en)	2004-11-29
ES2257410T3 (es)	2006-08-01
HK1054930A1 (en)	2003-12-19
GT200100117A (es)	2002-01-31
IL152771A0 (en)	2003-06-24
EA200201096A1 (ru)	2003-04-24
US7192963B2 (en)	2007-03-20
JP2004501922A (ja)	2004-01-22
KR20030017561A (ko)	2003-03-03
EP1686130A1 (en)	2006-08-02
PT1294724E (pt)	2006-07-31
TWI243820B (en)	2005-11-21
AP1911A (en)	2008-10-30
NO20026030D0 (no)	2002-12-16
SV2002000506A (es)	2002-10-24
ES2318605T3 (es)	2009-05-01
IS2305B (is)	2007-10-15
US20070161666A1 (en)	2007-07-12
EP1294724B1 (en)	2006-04-19
GEP20053541B (en)	2005-06-10
CA2412560C (en)	2008-12-30
ZA200210275B (en)	2003-12-19
NO324934B1 (no)	2008-01-07
SK17342002A3 (sk)	2004-06-08
AU6053801A (en)	2002-01-08
AP2002002695A0 (en)	2002-12-31
DE60118917T2 (de)	2006-11-30
DE60137734D1 (de)	2009-04-02
AU784297B2 (en)	2006-03-02
DZ3359A1 (fr)	2002-01-03
ECSP014105A (es)	2002-01-25
EP1294724A1 (en)	2003-03-26
IS6606A (is)	2002-10-31
HUP0301114A2 (hu)	2003-08-28
EP1686130B1 (en)	2009-02-18
MY127236A (en)	2006-11-30
MXPA03000068A (es)	2003-09-25
BR0111561A (pt)	2003-09-09
EA006153B1 (ru)	2005-10-27
DK1294724T3 (da)	2006-07-17
ATE423120T1 (de)	2009-03-15
EE200200711A (et)	2004-06-15
JP4068958B2 (ja)	2008-03-26
IL152771A (en)	2009-06-15
DOP2001000200A (es)	2003-02-15
AU784297C (en)	2007-01-11
ATE323704T1 (de)	2006-05-15
YU83302A (sh)	2005-09-19
CZ20023993A3 (cs)	2004-02-18
HRP20021000A2 (en)	2005-02-28
CN100351253C (zh)	2007-11-28
AR029279A1 (es)	2003-06-18
US6696567B2 (en)	2004-02-24
OA12292A (en)	2003-11-11
PA8521101A1 (es)	2002-04-25
UA74370C2 (uk)	2005-12-15
SI1294724T1 (sl)	2006-08-31
PL359563A1 (en)	2004-08-23
CA2412560A1 (en)	2002-01-03
US20030220353A1 (en)	2003-11-27
CU23263B7 (es)	2008-03-14
NO20026030L (no)	2002-12-16
DE60118917D1 (de)	2006-05-24

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KR20050086784A (ko)	2005-08-30	이식 거부반응의 치료 방법
JP2007512316A (ja)	2007-05-17	アテローム性動脈硬化症の治療方法
WO2005060972A2 (en)	2005-07-07	Pyrrolo [2,3-d] pyrimidine compounds for treating transplant rejection