OA11571A - PyrroloÄ2,3-düpyrimidine compounds. - Google Patents
PyrroloÄ2,3-düpyrimidine compounds. Download PDFInfo
- Publication number
- OA11571A OA11571A OA1200000348A OA1200000348A OA11571A OA 11571 A OA11571 A OA 11571A OA 1200000348 A OA1200000348 A OA 1200000348A OA 1200000348 A OA1200000348 A OA 1200000348A OA 11571 A OA11571 A OA 11571A
- Authority
- OA
- OAPI
- Prior art keywords
- alkyl
- aryl
- pyrrolo
- alkoxy
- heteroaryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 93
- 108010019421 Janus Kinase 3 Proteins 0.000 claims abstract description 33
- 102000006500 Janus Kinase 3 Human genes 0.000 claims abstract description 33
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 208000006673 asthma Diseases 0.000 claims abstract description 11
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 10
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 10
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 10
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 10
- 208000024799 Thyroid disease Diseases 0.000 claims abstract description 10
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 10
- 230000001363 autoimmune Effects 0.000 claims abstract description 10
- 201000011510 cancer Diseases 0.000 claims abstract description 10
- 206010025135 lupus erythematosus Diseases 0.000 claims abstract description 10
- 208000011231 Crohn disease Diseases 0.000 claims abstract description 9
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 9
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 9
- 208000032839 leukemia Diseases 0.000 claims abstract description 9
- 210000000056 organ Anatomy 0.000 claims abstract description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 135
- -1 (CpC^alkyl Chemical group 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 241000124008 Mammalia Species 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 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 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 206010052779 Transplant rejections Diseases 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 7
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims description 7
- 201000006417 multiple sclerosis Diseases 0.000 claims description 7
- 206010003645 Atopy Diseases 0.000 claims description 6
- 201000004624 Dermatitis Diseases 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 6
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000005936 piperidyl group Chemical group 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 4
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 210000000987 immune system Anatomy 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 125000005256 alkoxyacyl group Chemical group 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 2
- YAJAWZHVCVQZIW-UHFFFAOYSA-N 4-piperidin-1-yl-5-(trifluoromethyl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C=12C(C(F)(F)F)=CNC2=NC=NC=1N1CCCCC1 YAJAWZHVCVQZIW-UHFFFAOYSA-N 0.000 claims description 2
- XMDULOSPOORHTJ-UHFFFAOYSA-N 5-(2-methylpyridin-4-yl)-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=NC(C)=CC(C=2C3=C(N4CCCCC4)N=CN=C3NC=2)=C1 XMDULOSPOORHTJ-UHFFFAOYSA-N 0.000 claims description 2
- WZFLNSVJMWZIGG-UHFFFAOYSA-N 5-(3-methylphenyl)-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2C3=C(N4CCCCC4)N=CN=C3NC=2)=C1 WZFLNSVJMWZIGG-UHFFFAOYSA-N 0.000 claims description 2
- CIPYWMYUPREAMJ-UHFFFAOYSA-N 5-ethynyl-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C=12C(C#C)=CNC2=NC=NC=1N1CCCCC1 CIPYWMYUPREAMJ-UHFFFAOYSA-N 0.000 claims description 2
- LCTMPEQAHUTSGO-UHFFFAOYSA-N 5-fluoro-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C=12C(F)=CNC2=NC=NC=1N1CCCCC1 LCTMPEQAHUTSGO-UHFFFAOYSA-N 0.000 claims description 2
- 101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 claims description 2
- 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 235000001508 sulfur Nutrition 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- YWTBBNIUCJYYNU-UHFFFAOYSA-N 2-[3-ethyl-4-[2-hydroxyethyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclopentyl]propan-2-ol Chemical compound CCC1CC(C(C)(C)O)CC1N(CCO)C1=NC=NC2=C1C=CN2 YWTBBNIUCJYYNU-UHFFFAOYSA-N 0.000 claims 1
- VIXNVCQFOFBIJM-UHFFFAOYSA-N 2-[3-ethyl-4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclopentyl]propan-2-ol Chemical compound CCC1CC(C(C)(C)O)CC1N(C)C1=NC=NC2=C1C=CN2 VIXNVCQFOFBIJM-UHFFFAOYSA-N 0.000 claims 1
- SASXLRNIYRKHAE-UHFFFAOYSA-N 4-(2,3,3a,4,5,6,7,7a-octahydroindol-1-yl)-5-chloro-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CC2CCCCC2N1C1=C2C(Cl)=CNC2=NC=N1 SASXLRNIYRKHAE-UHFFFAOYSA-N 0.000 claims 1
- BHEXESBBAOCUEW-UHFFFAOYSA-N 4-(3,3-dimethylpiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1C(C)(C)CCCN1C1=NC=NC2=C1C=CN2 BHEXESBBAOCUEW-UHFFFAOYSA-N 0.000 claims 1
- SDCGYRLQORKUBU-UHFFFAOYSA-N n',n'-dimethyl-n-[[3-(4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl]methyl]ethane-1,2-diamine Chemical compound CN(C)CCNCC1=CC=CC(C=2C3=C(N4CCCCC4)N=CN=C3NC=2)=C1 SDCGYRLQORKUBU-UHFFFAOYSA-N 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 abstract description 4
- 239000003112 inhibitor Substances 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 206010012438 Dermatitis atopic Diseases 0.000 abstract 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 abstract 1
- 201000008937 atopic dermatitis Diseases 0.000 abstract 1
- 206010012601 diabetes mellitus Diseases 0.000 abstract 1
- 238000000034 method Methods 0.000 description 55
- 238000002844 melting Methods 0.000 description 46
- 230000008018 melting Effects 0.000 description 46
- 239000000203 mixture Substances 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 21
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 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 9
- 108010036949 Cyclosporine Proteins 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 229940093499 ethyl acetate Drugs 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- VPQAQEOATKTJSK-UHFFFAOYSA-N piperidine;pyrimidine Chemical compound C1CCNCC1.C1=CN=CN=C1 VPQAQEOATKTJSK-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 210000001744 T-lymphocyte Anatomy 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 102000004388 Interleukin-4 Human genes 0.000 description 5
- 108090000978 Interleukin-4 Proteins 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
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- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 4
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- POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 description 3
- WWNAKDRFVWZIMY-UHFFFAOYSA-N 1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CCCN1C1=NC=NC2=C1C=CN2 WWNAKDRFVWZIMY-UHFFFAOYSA-N 0.000 description 3
- BPTCCCTWWAUJRK-UHFFFAOYSA-N 4-chloro-7h-pyrrolo[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=CN2 BPTCCCTWWAUJRK-UHFFFAOYSA-N 0.000 description 3
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- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
- 229940077388 benzenesulfonate Drugs 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229960001265 ciclosporin Drugs 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
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- 229960003444 immunosuppressant agent Drugs 0.000 description 3
- 230000001861 immunosuppressant effect Effects 0.000 description 3
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- 229910052763 palladium Inorganic materials 0.000 description 3
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- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
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- 229940032147 starch Drugs 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
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- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
- A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8988698P | 1998-06-19 | 1998-06-19 |
Publications (1)
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|---|---|
| OA11571A true OA11571A (en) | 2004-07-01 |
Family
ID=22220084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200000348A OA11571A (en) | 1998-06-19 | 1999-06-14 | PyrroloÄ2,3-düpyrimidine compounds. |
Country Status (46)
Families Citing this family (168)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| EP1065207A1 (en) * | 1999-07-02 | 2001-01-03 | Aventis Pharma Deutschland GmbH | Naphthyridine derivatives, processes for their preparation, their use, and pharmaceutical compositions comprising them |
| DE60039059D1 (de) | 1999-10-07 | 2008-07-10 | Amgen Inc | Triazin-kinase-hemmer |
| DE19948417A1 (de) * | 1999-10-07 | 2001-04-19 | Morphochem Ag | Imidazol-Derivate und ihre Verwendung als Arzneimittel |
| SK287188B6 (sk) | 1999-12-10 | 2010-02-08 | Pfizer Products Inc. | Pyrolo [2,3-d]pyrimidínová zlúčenina, jej použitie a farmaceutická kompozícia alebo kombinácia s jej obsahom |
| EP1875900A3 (en) * | 2000-01-24 | 2010-07-21 | Genzyme Corporation | JAK/STAT pathway inhibitors and the use thereof for the treatment of osteoarthritis |
| WO2001052892A2 (en) * | 2000-01-24 | 2001-07-26 | Genzyme Corporation | Jak/stat pathway inhibitors and the uses thereof |
| MY145722A (en) * | 2000-04-27 | 2012-03-30 | Abbott Lab | Diazabicyclic central nervous system active agents |
| CN100351253C (zh) * | 2000-06-26 | 2007-11-28 | 辉瑞产品公司 | 作为免疫抑制剂的吡咯并[2,3－d]嘧啶化合物 |
| US6881737B2 (en) | 2001-04-11 | 2005-04-19 | Amgen Inc. | Substituted triazinyl acrylamide derivatives and methods of use |
| US6864255B2 (en) | 2001-04-11 | 2005-03-08 | Amgen Inc. | Substituted triazinyl amide derivatives and methods of use |
| US7301023B2 (en) | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| AP2003002929A0 (en) * | 2001-06-23 | 2003-12-31 | Aventis Pharma Inc | Pyrrolopyrimidines as protein kinase inhibitors |
| GB0115393D0 (en) * | 2001-06-23 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| GB0119249D0 (en) | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
| US7323469B2 (en) | 2001-08-07 | 2008-01-29 | Novartis Ag | 7H-pyrrolo[2,3-d]pyrimidine derivatives |
| GT200200234A (es) | 2001-12-06 | 2003-06-27 | Compuestos cristalinos novedosos | |
| US6642381B2 (en) * | 2001-12-27 | 2003-11-04 | Hoffman-La Roche Inc. | Pyrimido[5,4-e][1,2,4]triazine-5,7-diamine compounds as protein tyrosine phosphatase inhibitors |
| DK1474425T3 (da) | 2002-01-07 | 2006-09-25 | Eisai Co Ltd | Deazapuriner og anvendelser deraf |
| GB0202679D0 (en) * | 2002-02-05 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| EP1388541A1 (en) * | 2002-08-09 | 2004-02-11 | Centre National De La Recherche Scientifique (Cnrs) | Pyrrolopyrazines as kinase inhibitors |
| JP2006509000A (ja) | 2002-11-26 | 2006-03-16 | ファイザー・プロダクツ・インク | 移植片拒絶反応の処置の方法 |
| US7253166B2 (en) * | 2003-04-22 | 2007-08-07 | Irm Llc | 6-phenyl-7H-pyrrolo[2,3-d]pyrimidine compounds that induce neuronal differentiation in embryonic stem cells |
| US7169918B2 (en) * | 2003-10-27 | 2007-01-30 | Genelabs Technologies, Inc. | Methods for preparing 7-(2′-substituted-β-D-ribofuranosyl)-4-(NR2R3)-5-(substituted ethyn-1-yl)-pyrrolo[2,3-d]pyrimidine derivatives |
| WO2005069865A2 (en) * | 2004-01-13 | 2005-08-04 | Ambit Biosciences Corporation | Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases |
| GB0403606D0 (en) * | 2004-02-18 | 2004-03-24 | Novartis Ag | Organic compounds |
| JP5213229B2 (ja) * | 2004-04-23 | 2013-06-19 | エグゼリクシス， インコーポレイテッド | キナーゼ調節因子および使用方法 |
| CA2571710A1 (en) | 2004-06-24 | 2006-11-02 | Nicholas Valiante | Small molecule immunopotentiators and assays for their detection |
| EP1768982A2 (en) | 2004-06-29 | 2007-04-04 | Amgen Inc. | Pyrolo [2,3-d] pyrimidines that modulate ack1 and lck activity |
| AR050365A1 (es) | 2004-08-02 | 2006-10-18 | Osi Pharm Inc | Compuestos inhibidores de multi- quinasa pirrolopirimidina aril- amino sustituidos. |
| UY29177A1 (es) | 2004-10-25 | 2006-05-31 | Astex Therapeutics Ltd | Derivados sustituidos de purina, purinona y deazapurina, composiciones que los contienen métodos para su preparación y sus usos |
| MY179032A (en) | 2004-10-25 | 2020-10-26 | Cancer Research Tech Ltd | Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors |
| AR054416A1 (es) | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| FR2880626B1 (fr) * | 2005-01-13 | 2008-04-18 | Aventis Pharma Sa | Derives de la purine, compositions les contenant et utilisation |
| US7423043B2 (en) | 2005-02-18 | 2008-09-09 | Lexicon Pharmaceuticals, Inc. | 4-Piperidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine compounds |
| RU2411242C2 (ru) | 2005-05-13 | 2011-02-10 | Айрм, Ллк. | Соединения и композиции в качестве ингибиторов протеинкиназ |
| EP1910358A2 (en) | 2005-07-14 | 2008-04-16 | Astellas Pharma Inc. | Heterocyclic janus kinase 3 inhibitors |
| CN102127078A (zh) | 2005-07-14 | 2011-07-20 | 安斯泰来制药株式会社 | Janus激酶3的杂环类抑制剂 |
| EP2270014A1 (en) | 2005-09-22 | 2011-01-05 | Incyte Corporation | Azepine inhibitors of janus kinases |
| KR20080063809A (ko) * | 2005-09-30 | 2008-07-07 | 버텍스 파마슈티칼스 인코포레이티드 | 야누스 키나아제의 억제제로서 유용한 데아자퓨린 |
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