CA2465711A1 - Aminopyrimidines and pyridines - Google Patents
Aminopyrimidines and pyridines Download PDFInfo
- Publication number
- CA2465711A1 CA2465711A1 CA002465711A CA2465711A CA2465711A1 CA 2465711 A1 CA2465711 A1 CA 2465711A1 CA 002465711 A CA002465711 A CA 002465711A CA 2465711 A CA2465711 A CA 2465711A CA 2465711 A1 CA2465711 A1 CA 2465711A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- cycloalkyl
- hydrogen
- aryl
- alkylamino
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000005005 aminopyrimidines Chemical class 0.000 title abstract description 4
- 150000003222 pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 8
- 230000002503 metabolic effect Effects 0.000 claims abstract description 6
- 230000003211 malignant effect Effects 0.000 claims abstract description 5
- 229910052770 Uranium Inorganic materials 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 141
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- 239000001257 hydrogen Substances 0.000 claims description 125
- -1 halo (C1-C6) alkyl Chemical group 0.000 claims description 122
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 101
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 83
- 239000000203 mixture Substances 0.000 claims description 67
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 52
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
- 125000004442 acylamino group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000006413 ring segment Chemical group 0.000 claims description 13
- 125000005518 carboxamido group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 239000000543 intermediate Substances 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 3
- 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 claims description 3
- 229940125708 antidiabetic agent Drugs 0.000 claims description 3
- 239000003472 antidiabetic agent Substances 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
- 229960000485 methotrexate Drugs 0.000 claims description 3
- 229960001967 tacrolimus Drugs 0.000 claims description 3
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims description 3
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 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 claims description 2
- 229930105110 Cyclosporin A Natural products 0.000 claims description 2
- 108010036949 Cyclosporine Proteins 0.000 claims description 2
- 102000019223 Interleukin-1 receptor Human genes 0.000 claims description 2
- 108050006617 Interleukin-1 receptor Proteins 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229960002537 betamethasone Drugs 0.000 claims description 2
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229960001265 ciclosporin Drugs 0.000 claims description 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 2
- 229930182912 cyclosporin Natural products 0.000 claims description 2
- 229960003957 dexamethasone Drugs 0.000 claims description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 2
- 229960000890 hydrocortisone Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229960004618 prednisone Drugs 0.000 claims description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 2
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims description 2
- 229940044551 receptor antagonist Drugs 0.000 claims description 2
- 239000002464 receptor antagonist Substances 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 229960002930 sirolimus Drugs 0.000 claims description 2
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims description 2
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 13
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 10
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 4
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- XYRQRKKEOQCOAD-UHFFFAOYSA-N CC1(NC(=CC(=N1)C=NNC(N)=S)C=1N(C=NC1)C)NC(C)(C)C Chemical compound CC1(NC(=CC(=N1)C=NNC(N)=S)C=1N(C=NC1)C)NC(C)(C)C XYRQRKKEOQCOAD-UHFFFAOYSA-N 0.000 claims 1
- YGHLAYYCPHWUFW-UHFFFAOYSA-N CC1(NC(=CC(=N1)C=NNC(N)=S)C=1N(C=NC1)C)NC1CC1 Chemical compound CC1(NC(=CC(=N1)C=NNC(N)=S)C=1N(C=NC1)C)NC1CC1 YGHLAYYCPHWUFW-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- HIHTUKFRUKMHGB-UHFFFAOYSA-N O1CCC(CC1)CC1(NC(=CC(=N1)C=NNC(N)=S)C=1N(C=NC1)C)NC1CC1 Chemical compound O1CCC(CC1)CC1(NC(=CC(=N1)C=NNC(N)=S)C=1N(C=NC1)C)NC1CC1 HIHTUKFRUKMHGB-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 229940124623 antihistamine drug Drugs 0.000 claims 1
- UZMZVDOOVXLRID-UHFFFAOYSA-N azanylidyne-(nitrosulfonylamino)methane Chemical compound [O-][N+](=O)S(=O)(=O)NC#N UZMZVDOOVXLRID-UHFFFAOYSA-N 0.000 claims 1
- 229940111134 coxibs Drugs 0.000 claims 1
- 229960001810 meprednisone Drugs 0.000 claims 1
- PIDANAQULIKBQS-RNUIGHNZSA-N meprednisone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)CC2=O PIDANAQULIKBQS-RNUIGHNZSA-N 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 abstract description 10
- 239000003112 inhibitor Substances 0.000 abstract description 10
- 102000020233 phosphotransferase Human genes 0.000 abstract description 10
- 150000003927 aminopyridines Chemical class 0.000 abstract description 2
- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 126
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 235000019439 ethyl acetate Nutrition 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 31
- 150000002431 hydrogen Chemical group 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 27
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- 201000010099 disease Diseases 0.000 description 25
- 239000002904 solvent Substances 0.000 description 22
- 150000001299 aldehydes Chemical class 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 125000003710 aryl alkyl group Chemical group 0.000 description 16
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
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- 125000003884 phenylalkyl group Chemical group 0.000 description 15
- 239000012267 brine Substances 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 238000003786 synthesis reaction Methods 0.000 description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 11
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
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- 125000004438 haloalkoxy group Chemical group 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
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- 125000006239 protecting group Chemical group 0.000 description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
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- 239000003039 volatile agent Substances 0.000 description 5
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 4
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US33831201P | 2001-11-07 | 2001-11-07 | |
| US60/338,312 | 2001-11-07 | ||
| PCT/EP2002/012164 WO2003040131A1 (en) | 2001-11-07 | 2002-10-31 | Aminopyrimidines and pyridines |
Publications (1)
| Publication Number | Publication Date |
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| CA2465711A1 true CA2465711A1 (en) | 2003-05-15 |
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| CA002465711A Abandoned CA2465711A1 (en) | 2001-11-07 | 2002-10-31 | Aminopyrimidines and pyridines |
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| US (2) | US6846828B2 (enExample) |
| EP (1) | EP1444223A1 (enExample) |
| JP (1) | JP2005511608A (enExample) |
| KR (1) | KR20050042062A (enExample) |
| CN (1) | CN1582284A (enExample) |
| AR (1) | AR039554A1 (enExample) |
| BR (1) | BR0213899A (enExample) |
| CA (1) | CA2465711A1 (enExample) |
| MX (1) | MXPA04004166A (enExample) |
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| RU (1) | RU2308455C2 (enExample) |
| WO (1) | WO2003040131A1 (enExample) |
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| CN100441569C (zh) * | 2003-02-24 | 2008-12-10 | 横滨橡胶株式会社 | 化合物和使用了该化合物的组合物 |
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| BRPI0415390A (pt) * | 2003-10-14 | 2006-12-12 | Pharmacia Corp | compostos de pirazinona substituìda para o tratamento da inflamação |
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| SI1809624T1 (sl) * | 2004-08-28 | 2014-02-28 | Astrazeneca Ab | Derivati pirimidinsulfonamida kot modulatorji receptorja kemokina |
| AU2005315392B2 (en) * | 2004-12-17 | 2010-03-11 | Astrazeneca Ab | 4- (4- (imidazol-4-yl) pyrimidin-2-ylamino) benzamides as CDK inhibitors |
| GB0514017D0 (en) * | 2005-07-07 | 2005-08-17 | Ionix Pharmaceuticals Ltd | Chemical compounds |
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| GB2095240A (en) * | 1981-03-05 | 1982-09-29 | Fujisawa Pharmaceutical Co | Dihydropyrimidine derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
| DE59106752D1 (de) | 1990-05-16 | 1995-11-30 | Sulzer Chemtech Ag | Verfahren zur gerichteten fraktionierten Kristallisation. |
| EP0457727A1 (de) * | 1990-05-17 | 1991-11-21 | Ciba-Geigy Ag | Schädlingsbekämpfungsmittel |
| IL106786A (en) * | 1992-09-10 | 1997-02-18 | Basf Ag | Substituted pyridine derivatives and fungicidal compositions containing them |
| JP3398152B2 (ja) * | 1993-10-12 | 2003-04-21 | ブリストル‐マイヤーズ・スクイブ・ファーマ・カンパニー | 1n−アルキル−n−アリールピリミジンアミンおよびその誘導体 |
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| PL366114A1 (en) | 2000-10-26 | 2005-01-24 | Tularik Inc. | Antiinflammation agents |
-
2002
- 2002-10-31 RU RU2004117545/04A patent/RU2308455C2/ru not_active IP Right Cessation
- 2002-10-31 WO PCT/EP2002/012164 patent/WO2003040131A1/en not_active Ceased
- 2002-10-31 BR BR0213899-9A patent/BR0213899A/pt not_active IP Right Cessation
- 2002-10-31 PL PL02370480A patent/PL370480A1/xx not_active Application Discontinuation
- 2002-10-31 CN CNA02822194XA patent/CN1582284A/zh active Pending
- 2002-10-31 KR KR1020047006970A patent/KR20050042062A/ko not_active Withdrawn
- 2002-10-31 MX MXPA04004166A patent/MXPA04004166A/es not_active Application Discontinuation
- 2002-10-31 JP JP2003542177A patent/JP2005511608A/ja active Pending
- 2002-10-31 CA CA002465711A patent/CA2465711A1/en not_active Abandoned
- 2002-10-31 EP EP02785344A patent/EP1444223A1/en not_active Withdrawn
- 2002-11-06 US US10/288,968 patent/US6846828B2/en not_active Expired - Fee Related
- 2002-11-07 AR ARP020104262A patent/AR039554A1/es not_active Application Discontinuation
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2004
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| Publication number | Publication date |
|---|---|
| CN1582284A (zh) | 2005-02-16 |
| JP2005511608A (ja) | 2005-04-28 |
| US7157580B2 (en) | 2007-01-02 |
| AR039554A1 (es) | 2005-02-23 |
| US6846828B2 (en) | 2005-01-25 |
| MXPA04004166A (es) | 2004-07-08 |
| US20050107403A1 (en) | 2005-05-19 |
| KR20050042062A (ko) | 2005-05-04 |
| RU2308455C2 (ru) | 2007-10-20 |
| US20030144303A1 (en) | 2003-07-31 |
| EP1444223A1 (en) | 2004-08-11 |
| PL370480A1 (en) | 2005-05-30 |
| WO2003040131A1 (en) | 2003-05-15 |
| RU2004117545A (ru) | 2005-05-27 |
| BR0213899A (pt) | 2004-08-31 |
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