JP2010525025A5 - - Google Patents
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- Publication number
- JP2010525025A5 JP2010525025A5 JP2010504692A JP2010504692A JP2010525025A5 JP 2010525025 A5 JP2010525025 A5 JP 2010525025A5 JP 2010504692 A JP2010504692 A JP 2010504692A JP 2010504692 A JP2010504692 A JP 2010504692A JP 2010525025 A5 JP2010525025 A5 JP 2010525025A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- compound
- pyrimidin
- substituted
- alkyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 41
- 125000000217 alkyl group Chemical group 0.000 claims 39
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 34
- 150000002431 hydrogen Chemical class 0.000 claims 24
- -1 -I Chemical group 0.000 claims 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 150000003857 carboxamides Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 3
- GDWVCMUNHLLAQU-UHFFFAOYSA-N 2-[6-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]phenol Chemical compound CS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)O)=C1 GDWVCMUNHLLAQU-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- OJEBBFHEVUJONE-UHFFFAOYSA-N [2-[6-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]phenyl]methanol Chemical compound CS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)CO)=C1 OJEBBFHEVUJONE-UHFFFAOYSA-N 0.000 claims 2
- XTOMHCHXLAXPSD-UHFFFAOYSA-N [3-[[6-(2-ethoxy-5-fluorophenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCOC1=CC=C(F)C=C1C1=CC(NC=2C=C(CS(N)(=O)=O)C=CC=2)=NC=N1 XTOMHCHXLAXPSD-UHFFFAOYSA-N 0.000 claims 2
- NMZQJJULBWUWIJ-UHFFFAOYSA-N [3-[[6-(3-ethoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCOC1=CC=CC(C=2N=CN=C(NC=3C=C(CS(N)(=O)=O)C=CC=3)C=2)=C1 NMZQJJULBWUWIJ-UHFFFAOYSA-N 0.000 claims 2
- FYPVPYOTWMTLIL-UHFFFAOYSA-N [3-[[6-(3-fluorophenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=C(F)C=CC=2)=C1 FYPVPYOTWMTLIL-UHFFFAOYSA-N 0.000 claims 2
- JEKAROVFQXTUPL-UHFFFAOYSA-N [3-[[6-(3-phenylmethoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 JEKAROVFQXTUPL-UHFFFAOYSA-N 0.000 claims 2
- SERSRGJYQZHNME-UHFFFAOYSA-N [3-[[6-(4-fluorophenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=CC(F)=CC=2)=C1 SERSRGJYQZHNME-UHFFFAOYSA-N 0.000 claims 2
- LGFYKPSWAJESAR-UHFFFAOYSA-N [3-[[6-[2-(2-methoxyethoxy)phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COCCOC1=CC=CC=C1C1=CC(NC=2C=C(CS(N)(=O)=O)C=CC=2)=NC=N1 LGFYKPSWAJESAR-UHFFFAOYSA-N 0.000 claims 2
- FNVQNDGVNKTGEI-UHFFFAOYSA-N [3-[[6-[3-(1,2,4-triazol-1-ylmethyl)phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=C(CN3N=CN=C3)C=CC=2)=C1 FNVQNDGVNKTGEI-UHFFFAOYSA-N 0.000 claims 2
- GBAYTJKMNOIBLH-UHFFFAOYSA-N [3-[[6-[3-(diethylaminomethyl)phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCN(CC)CC1=CC=CC(C=2N=CN=C(NC=3C=C(CS(N)(=O)=O)C=CC=3)C=2)=C1 GBAYTJKMNOIBLH-UHFFFAOYSA-N 0.000 claims 2
- ZTGCWIHIQGSMGU-UHFFFAOYSA-N [3-[[6-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound C1CN(C)CCN1CC1=CC=CC(C=2N=CN=C(NC=3C=C(CS(N)(=O)=O)C=CC=3)C=2)=C1 ZTGCWIHIQGSMGU-UHFFFAOYSA-N 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- PLVVQSNGBWUHRU-UHFFFAOYSA-N n-[3-(methylsulfonylmethyl)phenyl]-6-(2-phenylmethoxyphenyl)pyrimidin-4-amine Chemical compound CS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)=C1 PLVVQSNGBWUHRU-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 claims 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims 1
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims 1
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 claims 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims 1
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 claims 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims 1
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 claims 1
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP2007003608 | 2007-04-24 | ||
| EPPCT/EP2007/003608 | 2007-04-24 | ||
| EP07106951 | 2007-04-25 | ||
| EP07106951.2 | 2007-04-25 | ||
| PCT/EP2008/055017 WO2008129080A1 (en) | 2007-04-24 | 2008-04-24 | 4, 6-disubstituted aminopyrimidine derivatives as inhibitors of protein kinases |
Publications (3)
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005047266A1 (en) | 2003-11-14 | 2005-05-26 | Lorus Therapeutics Inc. | Aryl imidazoles and their use as anti-cancer agents |
| CA2789200C (en) * | 2010-03-22 | 2020-05-26 | Lead Discovery Center Gmbh | Pharmaceutically active disubstituted triazine derivatives |
| CA2826464C (en) | 2011-03-02 | 2020-07-28 | Lead Discovery Center Gmbh | Pharmaceutically active disubstituted triazine derivatives |
| CN103562184B (zh) * | 2011-03-02 | 2016-04-27 | 利德探索中心有限公司 | 药学活性的二取代的吡啶衍生物 |
| CA2833288A1 (en) * | 2011-04-19 | 2012-10-26 | Bayer Intellectual Property Gmbh | Substituted 4-aryl-n-phenyl-1,3,5-triazin-2-amines |
| TW201636330A (zh) | 2011-05-24 | 2016-10-16 | 拜耳知識產權公司 | 含有硫醯亞胺基團之４－芳基－ｎ－苯基－１，３，５－三氮雜苯－２－胺 |
| EP2527332A1 (en) | 2011-05-24 | 2012-11-28 | Bayer Intellectual Property GmbH | 4-Aryl-N-phenyl-1,3,5-triazin-2-amines containing a sulfoximine group as CDK9 inhibitors |
| EP2755948B1 (en) | 2011-09-16 | 2016-05-25 | Bayer Intellectual Property GmbH | Disubstituted 5-fluoro pyrimidine derivatives containing a sulfoximine group |
| JP5982490B2 (ja) * | 2011-09-16 | 2016-08-31 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 二置換５−フルオロ−ピリミジン |
| WO2013059634A1 (en) | 2011-10-20 | 2013-04-25 | The Regents Of The University Of California | Use of cdk9 inhibitors to reduce cartilage degradation |
| JP6639231B2 (ja) * | 2012-08-23 | 2020-02-05 | ヴィロスタティクス・ソチエタ・ア・レスポンサビリタ・リミタータＶｉｒｏＳｔａｔｉｃｓ ｓｒｌ | 新規な４，６−二置換アミノピリミジン誘導体 |
| JP2015536311A (ja) | 2012-10-18 | 2015-12-21 | バイエル ファーマ アクチエンゲゼルシャフト | スルホン基を含有する４−（オルト）−フルオロフェニル−５−フルオロピリミジン−２−イルアミン |
| US9708293B2 (en) | 2012-10-18 | 2017-07-18 | Bayer Pharma Aktiengesellschaft | N-(pyridin-2-yl)pyrimidin-4-amine derivatives containing a sulfone group |
| ES2595222T3 (es) | 2012-10-18 | 2016-12-28 | Bayer Pharma Aktiengesellschaft | Derivados de 5-fluoro-N-(piridin-2-il)piridin-2-amina que contienen un grupo sulfona |
| EP2920153B1 (en) * | 2012-11-15 | 2017-02-01 | Bayer Pharma Aktiengesellschaft | 4-(ortho)-fluorophenyl-5-fluoropyrimidin-2-yl amines containing a sulfoximine group |
| TW201418243A (zh) | 2012-11-15 | 2014-05-16 | Bayer Pharma AG | 含有磺醯亞胺基團之ｎ－（吡啶－２－基）嘧啶－４－胺衍生物 |
| EP2928878B1 (en) * | 2012-11-15 | 2016-11-02 | Bayer Pharma Aktiengesellschaft | 5-fluoro-n-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfoximine group |
| EP3016945B1 (en) | 2013-07-04 | 2017-05-03 | Bayer Pharma Aktiengesellschaft | Sulfoximine substituted 5-fluoro-n-(pyridin-2-yl)pyridin-2-amine derivatives and their use as cdk9 kinase inhibitors |
| US20150104392A1 (en) | 2013-10-04 | 2015-04-16 | Aptose Biosciences Inc. | Compositions, biomarkers and their use in the treatment of cancer |
| AR098394A1 (es) | 2013-11-25 | 2016-05-26 | Lilly Co Eli | Inhibidores de dgat2 (diacilglicerol o-aciltransferasa 2) |
| CA2942119A1 (en) | 2014-03-13 | 2015-09-17 | Bayer Pharma Aktiengesellschaft | 5-fluoro-n-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfone group |
| CN106414412B (zh) | 2014-04-01 | 2019-06-21 | 拜耳医药股份有限公司 | 含有磺酰二亚胺基团的二取代的5-氟嘧啶衍生物 |
| US10383873B2 (en) | 2014-04-04 | 2019-08-20 | Memorial Sloan-Kettering Cancer Center | Method and kits for identifying of CDK9 inhibitors for the treatment of cancer |
| CA2945237C (en) | 2014-04-11 | 2022-09-06 | Ulrich Lucking | Novel macrocyclic compounds |
| EP3206749B1 (en) | 2014-10-14 | 2021-09-08 | The Regents of the University of California | The cdk9 and brd4 inhibitors flavopiridol and jq1 to inhibit cartilage inflammation |
| WO2016059011A1 (en) | 2014-10-16 | 2016-04-21 | Bayer Pharma Aktiengesellschaft | Fluorinated benzofuranyl-pyrimidine derivatives containing a sulfone group |
| JP6671359B2 (ja) | 2014-10-16 | 2020-03-25 | バイエル ファーマ アクチエンゲゼルシャフト | スルホキシイミン基を含むフッ素化ベンゾフラニル−ピリミジン誘導体 |
| EP3274338A1 (en) | 2015-03-24 | 2018-01-31 | Bayer Pharma Aktiengesellschaft | Use of 4-(4-fluoro-2-methoxyphenyl)-n-{3-[(s-methylsulfonimidoyl)methyl]phenyl}-1,3,5-triazin-2-amine for treating multiple myeloma |
| EP3273963A1 (en) | 2015-03-24 | 2018-01-31 | Bayer Pharma Aktiengesellschaft | Use of 4-(4-fluoro-2-methoxyphenyl)-n-{3-[(s-methylsulfonimidoyl)methyl]phenyl}-1,3,5-triazin-2-amine for treating lymphomas |
| WO2016150902A1 (en) | 2015-03-24 | 2016-09-29 | Bayer Pharma Aktiengesellschaft | Use of 4-(4-fluoro-2-methoxyphenyl)-n-{3-[(s-methylsulfonimidoyl)methyl]phenyl}-1,3,5-triazin-2-amine for treating gastric cancers |
| US9845331B2 (en) | 2015-06-29 | 2017-12-19 | Astrazeneca Ab | Chemical compounds |
| WO2017055196A1 (en) | 2015-09-29 | 2017-04-06 | Bayer Pharma Aktiengesellschaft | Novel macrocyclic sulfondiimine compounds |
| CN108368129B (zh) | 2015-10-08 | 2021-08-17 | 拜耳医药股份有限公司 | 改性大环化合物 |
| WO2017060322A2 (en) | 2015-10-10 | 2017-04-13 | Bayer Pharma Aktiengesellschaft | Ptefb-inhibitor-adc |
| US20180015153A1 (en) | 2016-07-16 | 2018-01-18 | Florida State University Research Foundation, Inc. | Compounds and methods for treatment and prevention of flavivirus infection |
| CA3057891A1 (en) | 2017-03-28 | 2018-10-04 | Bayer Aktiengesellschaft | Novel ptefb inhibiting macrocyclic compounds |
| ES2900199T3 (es) | 2017-03-28 | 2022-03-16 | Bayer Ag | Novedosos compuestos macrocíclicos inhibidores de PTEFB |
| WO2019075011A1 (en) | 2017-10-10 | 2019-04-18 | Florida State University Research Foundation, Inc. | EMETIC COMPOUNDS FOR THE TREATMENT AND PREVENTION OF FLAVIVIRUS INFECTION |
| CA3081261A1 (en) | 2017-10-30 | 2019-05-09 | Aptose Biosciences Inc. | Aryl imidazoles for the treatment of cancer |
| MA51820A (fr) | 2018-02-13 | 2021-05-19 | Bayer Ag | Utilisation de 5-fluoro-4-(4-fluoro-2-méthoxyphényl)-n-(4-[(s-méthylsulfonimidoyl)méthyl]pyridin-2-yl)pyridin-2-amine pour traiter un lymphome diffus à grandes cellules b |
| WO2020235672A1 (ja) * | 2019-05-23 | 2020-11-26 | 国立大学法人京都大学 | アルツハイマー病のための医薬組成物 |
| US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9319568D0 (en) | 1993-09-22 | 1993-11-10 | Euro Celtique Sa | Pharmaceutical compositions and usages |
| HUP0300382A3 (en) | 2000-03-29 | 2006-11-28 | Cyclacel Ltd | 2-substituted 4-heteroaryl-pyrimidines and their use in the treatmetn of proliferative disorders and pharmaceutical compositions containing the compounds |
| CA2441733A1 (en) | 2001-03-29 | 2002-10-10 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases |
| GB0205693D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| US20040106647A1 (en) | 2002-06-28 | 2004-06-03 | Schneider Michael D. | Modulators of Cdk9 as a therapeutic target in cardiac hypertrophy |
| US7576085B2 (en) | 2002-09-23 | 2009-08-18 | Schering Corporation | Imidazopyrazines as cyclin dependent kinase inhibitors |
| US7419984B2 (en) * | 2002-10-17 | 2008-09-02 | Cell Therapeutics, Inc. | Pyrimidines and uses thereof |
| JP2006507302A (ja) | 2002-10-30 | 2006-03-02 | メルク エンド カムパニー インコーポレーテッド | キナーゼ阻害剤 |
| US20070161637A1 (en) | 2003-07-22 | 2007-07-12 | Neurogen Corporation | Substituted pyridin-2-ylamine analogues |
| JP2007500179A (ja) | 2003-07-30 | 2007-01-11 | サイクラセル・リミテッド | キナーゼ阻害剤としての２−アミノフェニル−４−フェニルピリミジン |
| EP1678147B1 (en) * | 2003-09-15 | 2012-08-08 | Lead Discovery Center GmbH | Pharmaceutically active 4,6-disubstituted aminopyrimidine derivatives as modulators of protein kinases |
| EP1709007A1 (en) | 2004-01-22 | 2006-10-11 | Altana Pharma AG | N-4-(6-(heteo)aryl-pyrimidin-4-ylaminophenyl)-benzenesulfonamides as kinase inhibitors |
| TW200614993A (en) | 2004-06-11 | 2006-05-16 | Akzo Nobel Nv | 4-phenyl-pyrimidine-2-carbonitrile derivatives |
| EP1901747A2 (en) * | 2005-05-25 | 2008-03-26 | Ingenium Pharmaceuticals AG | Pyrimidine-based cdk inhibitors for treating pain |
| US8389521B2 (en) * | 2007-04-24 | 2013-03-05 | Ingenium Pharmaceuticals Gmbh | Inhibitors of protein kinases |
| US8436007B2 (en) * | 2007-04-24 | 2013-05-07 | Ingenium Pharmaceuticals Gmbh | Inhibitors of protein kinases |
| US8507511B2 (en) * | 2007-04-24 | 2013-08-13 | Ingenium Pharmaceuticals Gmbh | Inhibitors of protein kinases |
-
2008
- 2008-04-24 EP EP08749710A patent/EP2137166B1/en not_active Not-in-force
- 2008-04-24 US US12/451,039 patent/US8507498B2/en not_active Expired - Fee Related
- 2008-04-24 JP JP2010504692A patent/JP5566880B2/ja not_active Expired - Fee Related
- 2008-04-24 WO PCT/EP2008/055017 patent/WO2008129080A1/en not_active Ceased
-
2013
- 2013-08-12 US US13/964,814 patent/US20130338147A1/en not_active Abandoned
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