JP2010525025A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
- CZPKDOCUGZUVEL-UHFFFAOYSA-N 1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]-n,n-dimethylmethanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)N(C)C)C=CC=2)=NC=N1 CZPKDOCUGZUVEL-UHFFFAOYSA-N 0.000 claims 1
- VJLQYOHFGHKHAR-UHFFFAOYSA-N 1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]-n-propan-2-ylmethanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NC(C)C)C=CC=2)=NC=N1 VJLQYOHFGHKHAR-UHFFFAOYSA-N 0.000 claims 1
- YCYNZAXHFTZTCR-UHFFFAOYSA-N 1-[[3-[6-[3-(sulfamoylmethyl)anilino]pyrimidin-4-yl]phenyl]methyl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1CC1=CC=CC(C=2N=CN=C(NC=3C=C(CS(N)(=O)=O)C=CC=3)C=2)=C1 YCYNZAXHFTZTCR-UHFFFAOYSA-N 0.000 claims 1
- OLYVSPQOMLJIBX-UHFFFAOYSA-N 1-[[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methylsulfonyl]piperidine-4-carboxamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)N3CCC(CC3)C(N)=O)C=CC=2)=NC=N1 OLYVSPQOMLJIBX-UHFFFAOYSA-N 0.000 claims 1
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 claims 1
- FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 claims 1
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 claims 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims 1
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 claims 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 claims 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 claims 1
- VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 claims 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 claims 1
- BILVKAZBOMIMFA-UHFFFAOYSA-N 6-(2-methoxyphenyl)-n-[3-(methylsulfonylmethyl)phenyl]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=N1 BILVKAZBOMIMFA-UHFFFAOYSA-N 0.000 claims 1
- GBBFCQBVKYMIAV-UHFFFAOYSA-N 6-(2-methoxyphenyl)-n-[3-(morpholin-4-ylsulfonylmethyl)phenyl]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)N3CCOCC3)C=CC=2)=NC=N1 GBBFCQBVKYMIAV-UHFFFAOYSA-N 0.000 claims 1
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 claims 1
- IQZMHLBSLLBUMA-UHFFFAOYSA-N 6-[2-(2-methoxyethoxy)phenyl]-n-[3-(methylsulfonylmethyl)phenyl]pyrimidin-4-amine Chemical compound COCCOC1=CC=CC=C1C1=CC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=N1 IQZMHLBSLLBUMA-UHFFFAOYSA-N 0.000 claims 1
- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 claims 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 claims 1
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 claims 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 claims 1
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 229940126657 Compound 17 Drugs 0.000 claims 1
- 229940126639 Compound 33 Drugs 0.000 claims 1
- 229940127007 Compound 39 Drugs 0.000 claims 1
- RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 claims 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 claims 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 claims 1
- OBRFYRHKQFQFHT-UHFFFAOYSA-N [3-[(6-phenylpyrimidin-4-yl)amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=CC=CC=2)=C1 OBRFYRHKQFQFHT-UHFFFAOYSA-N 0.000 claims 1
- ROHCZDVQWUKBLA-UHFFFAOYSA-N [3-[[2-amino-6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(N)(=O)=O)C=CC=2)=NC(N)=N1 ROHCZDVQWUKBLA-UHFFFAOYSA-N 0.000 claims 1
- IKJUSUAXLZLEDN-UHFFFAOYSA-N [3-[[6-(2,3-dimethoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC(C=2N=CN=C(NC=3C=C(CS(N)(=O)=O)C=CC=3)C=2)=C1OC IKJUSUAXLZLEDN-UHFFFAOYSA-N 0.000 claims 1
- IQWHQUKBMVJFFH-UHFFFAOYSA-N [3-[[6-(2-chlorophenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)Cl)=C1 IQWHQUKBMVJFFH-UHFFFAOYSA-N 0.000 claims 1
- CITCBKKAVRLYPK-UHFFFAOYSA-N [3-[[6-(2-ethoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCOC1=CC=CC=C1C1=CC(NC=2C=C(CS(N)(=O)=O)C=CC=2)=NC=N1 CITCBKKAVRLYPK-UHFFFAOYSA-N 0.000 claims 1
- ZUYTZTSDNVGNIM-UHFFFAOYSA-N [3-[[6-(2-ethylphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCC1=CC=CC=C1C1=CC(NC=2C=C(CS(N)(=O)=O)C=CC=2)=NC=N1 ZUYTZTSDNVGNIM-UHFFFAOYSA-N 0.000 claims 1
- XXGFARXOUAOWST-UHFFFAOYSA-N [3-[[6-(2-fluorophenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)F)=C1 XXGFARXOUAOWST-UHFFFAOYSA-N 0.000 claims 1
- ZHJGXBCMUHGPBX-UHFFFAOYSA-N [3-[[6-(2-hydroxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)O)=C1 ZHJGXBCMUHGPBX-UHFFFAOYSA-N 0.000 claims 1
- DTCVSZXYRKTBCX-UHFFFAOYSA-N [3-[[6-(2-phenylmethoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)=C1 DTCVSZXYRKTBCX-UHFFFAOYSA-N 0.000 claims 1
- SOTKBNIIJQBSDU-UHFFFAOYSA-N [3-[[6-(2-propan-2-yloxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CC(C)OC1=CC=CC=C1C1=CC(NC=2C=C(CS(N)(=O)=O)C=CC=2)=NC=N1 SOTKBNIIJQBSDU-UHFFFAOYSA-N 0.000 claims 1
- WREUWDHHENZLAS-UHFFFAOYSA-N [3-[[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC(F)=CC=C1C1=CC(NC=2C=C(CS(N)(=O)=O)C=CC=2)=NC=N1 WREUWDHHENZLAS-UHFFFAOYSA-N 0.000 claims 1
- YCKTYTNGSMLUBX-UHFFFAOYSA-N [3-[[6-(4-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CC(NC=2C=C(CS(N)(=O)=O)C=CC=2)=NC=N1 YCKTYTNGSMLUBX-UHFFFAOYSA-N 0.000 claims 1
- HWBNNXMWIRXKGZ-UHFFFAOYSA-N [3-[[6-[2-(2-methoxyethoxy)phenyl]-2-methylpyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COCCOC1=CC=CC=C1C1=CC(NC=2C=C(CS(N)(=O)=O)C=CC=2)=NC(C)=N1 HWBNNXMWIRXKGZ-UHFFFAOYSA-N 0.000 claims 1
- IENFUVLVMKHQBM-UHFFFAOYSA-N [3-[[6-[2-(hydroxymethyl)phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)CO)=C1 IENFUVLVMKHQBM-UHFFFAOYSA-N 0.000 claims 1
- IFTAZJOJAZRQIT-UHFFFAOYSA-N [3-[[6-[2-(oxolan-2-ylmethoxy)phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)OCC2OCCC2)=C1 IFTAZJOJAZRQIT-UHFFFAOYSA-N 0.000 claims 1
- QGSRZMLWSFQFBR-UHFFFAOYSA-N [3-[[6-[2-(oxolan-3-yloxy)phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)OC2COCC2)=C1 QGSRZMLWSFQFBR-UHFFFAOYSA-N 0.000 claims 1
- DHNACVIXNXRARP-UHFFFAOYSA-N [3-[[6-[3-(hydroxymethyl)phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=C(CO)C=CC=2)=C1 DHNACVIXNXRARP-UHFFFAOYSA-N 0.000 claims 1
- WLMFWXPMVMFQIK-UHFFFAOYSA-N [3-[[6-[3-(morpholin-4-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(CN3CCOCC3)C=CC=2)=C1 WLMFWXPMVMFQIK-UHFFFAOYSA-N 0.000 claims 1
- OFFCNUCECGWQFN-UHFFFAOYSA-N [3-[[6-[3-(trifluoromethyl)phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=C(C=CC=2)C(F)(F)F)=C1 OFFCNUCECGWQFN-UHFFFAOYSA-N 0.000 claims 1
- SMZRIIOGVDLKCC-UHFFFAOYSA-N [3-[[6-[3-[(dimethylamino)methyl]phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CN(C)CC1=CC=CC(C=2N=CN=C(NC=3C=C(CS(N)(=O)=O)C=CC=3)C=2)=C1 SMZRIIOGVDLKCC-UHFFFAOYSA-N 0.000 claims 1
- YTBYYTAYUDLODS-UHFFFAOYSA-N [3-[[6-[3-[[2-(hydroxymethyl)piperidin-1-yl]methyl]phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=C(CN3C(CCCC3)CO)C=CC=2)=C1 YTBYYTAYUDLODS-UHFFFAOYSA-N 0.000 claims 1
- WFSMTVZJDKCVST-UHFFFAOYSA-N [3-[[6-[3-[[3-(2-hydroxyethyl)piperidin-1-yl]methyl]phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=C(CN3CC(CCO)CCC3)C=CC=2)=C1 WFSMTVZJDKCVST-UHFFFAOYSA-N 0.000 claims 1
- XKVJAVFKZWOSLV-UHFFFAOYSA-N [3-[[6-[3-[[3-(hydroxymethyl)piperidin-1-yl]methyl]phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C=C(CN3CC(CO)CCC3)C=CC=2)=C1 XKVJAVFKZWOSLV-UHFFFAOYSA-N 0.000 claims 1
- KGTMAYUFSMNYER-UHFFFAOYSA-N [3-[[6-[3-[[ethyl(propan-2-yl)amino]methyl]phenyl]pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCN(C(C)C)CC1=CC=CC(C=2N=CN=C(NC=3C=C(CS(N)(=O)=O)C=CC=3)C=2)=C1 KGTMAYUFSMNYER-UHFFFAOYSA-N 0.000 claims 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 claims 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 229940125773 compound 10 Drugs 0.000 claims 1
- 229940125797 compound 12 Drugs 0.000 claims 1
- 229940126543 compound 14 Drugs 0.000 claims 1
- 229940125758 compound 15 Drugs 0.000 claims 1
- 229940126142 compound 16 Drugs 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 229940125810 compound 20 Drugs 0.000 claims 1
- 229940126086 compound 21 Drugs 0.000 claims 1
- 229940126208 compound 22 Drugs 0.000 claims 1
- 229940125833 compound 23 Drugs 0.000 claims 1
- 229940125961 compound 24 Drugs 0.000 claims 1
- 229940125846 compound 25 Drugs 0.000 claims 1
- 229940125851 compound 27 Drugs 0.000 claims 1
- 229940127204 compound 29 Drugs 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 229940125877 compound 31 Drugs 0.000 claims 1
- 229940125878 compound 36 Drugs 0.000 claims 1
- 229940125807 compound 37 Drugs 0.000 claims 1
- 229940127573 compound 38 Drugs 0.000 claims 1
- 229940126540 compound 41 Drugs 0.000 claims 1
- 229940125936 compound 42 Drugs 0.000 claims 1
- 229940125844 compound 46 Drugs 0.000 claims 1
- 229940127271 compound 49 Drugs 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 229940126545 compound 53 Drugs 0.000 claims 1
- 229940127113 compound 57 Drugs 0.000 claims 1
- 229940125900 compound 59 Drugs 0.000 claims 1
- 229940126179 compound 72 Drugs 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 claims 1
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- BIMBZKCJRCFFOT-UHFFFAOYSA-N n,n-diethyl-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCN(CC)S(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)OC)=C1 BIMBZKCJRCFFOT-UHFFFAOYSA-N 0.000 claims 1
- YCJZWBZJSYLMPB-UHFFFAOYSA-N n-(2-chloropyrimidin-4-yl)-2,5-dimethyl-1-phenylimidazole-4-carboxamide Chemical compound CC=1N(C=2C=CC=CC=2)C(C)=NC=1C(=O)NC1=CC=NC(Cl)=N1 YCJZWBZJSYLMPB-UHFFFAOYSA-N 0.000 claims 1
- VEMIRJMLFNMFSE-UHFFFAOYSA-N n-(2-hydroxyethyl)-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]-n-methylmethanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)N(C)CCO)C=CC=2)=NC=N1 VEMIRJMLFNMFSE-UHFFFAOYSA-N 0.000 claims 1
- CWZDNXOQKLTXPF-UHFFFAOYSA-N n-(2-hydroxyethyl)-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NCCO)C=CC=2)=NC=N1 CWZDNXOQKLTXPF-UHFFFAOYSA-N 0.000 claims 1
- ATZHTAVSOHZEPL-UHFFFAOYSA-N n-(2-methoxyethyl)-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COCCNS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)OC)=C1 ATZHTAVSOHZEPL-UHFFFAOYSA-N 0.000 claims 1
- KFLXEXVKVIHKNJ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NCC=3C=CC(Cl)=CC=3)C=CC=2)=NC=N1 KFLXEXVKVIHKNJ-UHFFFAOYSA-N 0.000 claims 1
- DBERNNHTUSEQAG-UHFFFAOYSA-N n-[3-(azepan-1-ylsulfonylmethyl)phenyl]-6-(2-methoxyphenyl)pyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)N3CCCCCC3)C=CC=2)=NC=N1 DBERNNHTUSEQAG-UHFFFAOYSA-N 0.000 claims 1
- CHMFALJBUVEPEZ-UHFFFAOYSA-N n-[3-(methylsulfonylmethyl)phenyl]-6-[2-(oxolan-2-ylmethoxy)phenyl]pyrimidin-4-amine Chemical compound CS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)OCC2OCCC2)=C1 CHMFALJBUVEPEZ-UHFFFAOYSA-N 0.000 claims 1
- NFYFGDJUBLKFRP-UHFFFAOYSA-N n-[3-(methylsulfonylmethyl)phenyl]-6-[2-(oxolan-3-yloxy)phenyl]pyrimidin-4-amine Chemical compound CS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)OC2COCC2)=C1 NFYFGDJUBLKFRP-UHFFFAOYSA-N 0.000 claims 1
- OZCUQUIDFUWXOI-UHFFFAOYSA-N n-[3-[3-(dimethylamino)propylsulfonylmethyl]phenyl]-6-(2-methoxyphenyl)pyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)CCCN(C)C)C=CC=2)=NC=N1 OZCUQUIDFUWXOI-UHFFFAOYSA-N 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 claims 1
- ULOYSLBNBOXTQQ-UHFFFAOYSA-N n-cyclohexyl-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NC3CCCCC3)C=CC=2)=NC=N1 ULOYSLBNBOXTQQ-UHFFFAOYSA-N 0.000 claims 1
- LHPJRIPQMWWHHP-UHFFFAOYSA-N n-cyclopentyl-1-[3-[[6-(2-ethoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCOC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NC3CCCC3)C=CC=2)=NC=N1 LHPJRIPQMWWHHP-UHFFFAOYSA-N 0.000 claims 1
- LCCLFIXXGKGUFH-UHFFFAOYSA-N n-cyclopentyl-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NC3CCCC3)C=CC=2)=NC=N1 LCCLFIXXGKGUFH-UHFFFAOYSA-N 0.000 claims 1
- MZCYXTGSTQINHA-UHFFFAOYSA-N n-cyclopropyl-1-[3-[[6-(2-ethoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCOC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NC3CC3)C=CC=2)=NC=N1 MZCYXTGSTQINHA-UHFFFAOYSA-N 0.000 claims 1
- GGCVALUNBDTFJP-UHFFFAOYSA-N n-cyclopropyl-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NC3CC3)C=CC=2)=NC=N1 GGCVALUNBDTFJP-UHFFFAOYSA-N 0.000 claims 1
- QUOLTJIEELOYSW-UHFFFAOYSA-N n-ethyl-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCNS(=O)(=O)CC1=CC=CC(NC=2N=CN=C(C=2)C=2C(=CC=CC=2)OC)=C1 QUOLTJIEELOYSW-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- QKWMVDDSWVTGKT-UHFFFAOYSA-N n-tert-butyl-1-[3-[[6-(2-ethoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound CCOC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NC(C)(C)C)C=CC=2)=NC=N1 QKWMVDDSWVTGKT-UHFFFAOYSA-N 0.000 claims 1
- LFZHDLVMIDDORW-UHFFFAOYSA-N n-tert-butyl-1-[3-[[6-(2-methoxyphenyl)pyrimidin-4-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(NC=2C=C(CS(=O)(=O)NC(C)(C)C)C=CC=2)=NC=N1 LFZHDLVMIDDORW-UHFFFAOYSA-N 0.000 claims 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 Cc1nc(*)nc(N(*)*)c1* Chemical compound Cc1nc(*)nc(N(*)*)c1* 0.000 description 1
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)
| Publication Number | Publication Date |
|---|---|
| JP2010525025A JP2010525025A (ja) | 2010-07-22 |
| JP2010525025A5 true JP2010525025A5 (index.php) | 2011-06-23 |
| JP5566880B2 JP5566880B2 (ja) | 2014-08-06 |
Family
ID=39745232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010504692A Expired - Fee Related JP5566880B2 (ja) | 2007-04-24 | 2008-04-24 | プロテインキナーゼの阻害剤としての４，６−二置換アミノピリミジン誘導体 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US8507498B2 (index.php) |
| EP (1) | EP2137166B1 (index.php) |
| JP (1) | JP5566880B2 (index.php) |
| WO (1) | WO2008129080A1 (index.php) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8969372B2 (en) | 2003-11-14 | 2015-03-03 | Aptose Boisciences Inc. | Aryl imidazoles and their use as anti-cancer agents |
| EP2550257B1 (en) * | 2010-03-22 | 2016-12-21 | Lead Discovery Center GmbH | Pharmaceutically active disubstituted triazine derivatives |
| WO2012117059A1 (en) * | 2011-03-02 | 2012-09-07 | Lead Discovery Center Gmbh | Pharmaceutically active disubstituted pyridine derivatives |
| CN103582482B (zh) | 2011-03-02 | 2016-10-12 | 利德探索中心有限公司 | 药学活性的二取代的三嗪衍生物 |
| WO2012143399A1 (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 |
| ES2588102T3 (es) | 2011-09-16 | 2016-10-28 | Bayer Intellectual Property Gmbh | Derivados de 5-fluoro-pirimidina disustituidos que contienen un grupo sulfoximina |
| EP2755956B1 (en) * | 2011-09-16 | 2016-05-18 | Bayer Intellectual Property GmbH | 2,4-disubstituted 5-fluoro-pyrimidines as selective cdk9 inhibtors |
| US9498471B2 (en) | 2011-10-20 | 2016-11-22 | The Regents Of The University Of California | Use of CDK9 inhibitors to reduce cartilage degradation |
| SG11201501041VA (en) * | 2012-08-23 | 2015-03-30 | Virostatics Srl | Novel 4,6-disubstituted aminopyrimidine derivatives |
| US9670161B2 (en) | 2012-10-18 | 2017-06-06 | Bayer Pharma Aktiengesellschaft | 5-fluoro-N-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfone group |
| CN105283453B (zh) * | 2012-10-18 | 2018-06-22 | 拜耳药业股份公司 | 含砜基的n-(吡啶-2-基)嘧啶-4-胺衍生物 |
| CA2888381A1 (en) | 2012-10-18 | 2014-04-24 | Bayer Pharma Aktiengesellschaft | 4-(ortho)-fluorophenyl-5-fluoropyrimidin-2-yl amines containing a sulfone group |
| ES2612978T3 (es) | 2012-11-15 | 2017-05-19 | Bayer Pharma Aktiengesellschaft | Derivados de 5-fluoro-n-(piridin-2-il)piridin-2-amina que contienen un grupo sulfoximina |
| 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 |
| US9499492B2 (en) * | 2012-11-15 | 2016-11-22 | Bayer Pharma Aktiengesellschaft | 4-(ortho)-fluorophenyl-5-fluoropyrimidin-2-yl amines containing a sulfoximine group |
| HK1218296A1 (zh) | 2013-07-04 | 2017-02-10 | Bayer Pharma Aktiengesellschaft | 磺亚胺取代的5-氟-n-(吡啶-2-基)吡啶-2-胺衍生物以及其作爲cdk9激酶抑制剂的用途 |
| JP6946000B2 (ja) * | 2013-10-04 | 2021-10-06 | アプトース バイオサイエンシーズ， インコーポレイテッド | がんの治療用組成物及び方法 |
| AR098394A1 (es) | 2013-11-25 | 2016-05-26 | Lilly Co Eli | Inhibidores de dgat2 (diacilglicerol o-aciltransferasa 2) |
| JP2017508757A (ja) | 2014-03-13 | 2017-03-30 | 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５−フルオロ−ｎ−（ピリジン−２−イル）ピリジン−２−アミン誘導体 |
| JP6503372B2 (ja) | 2014-04-01 | 2019-04-17 | バイエル ファーマ アクチエンゲゼルシャフト | スルホンジイミン基を含むジ置換５−フルオロピリミジン誘導体 |
| CA2944727A1 (en) | 2014-04-04 | 2015-10-08 | Memorial Sloan-Kettering Cancer Center | Method and kits for identifying of cdk9 inhibitors for the treatment of cancer |
| KR102383938B1 (ko) | 2014-04-11 | 2022-04-08 | 바이엘 파마 악티엔게젤샤프트 | 신규한 매크로시클릭 화합물 |
| JP6930913B2 (ja) | 2014-10-14 | 2021-09-01 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニアＴｈｅ Ｒｅｇｅｎｔｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｃａｌｉｆｏｒｎｉａ | 炎症を阻害するためのｃｄｋ９及びｂｒｄ４阻害剤の使用法 |
| WO2016059086A1 (en) | 2014-10-16 | 2016-04-21 | Bayer Pharma Aktiengesellschaft | Fluorinated benzofuranyl-pyrimidine derivatives containing a sulfoximine group |
| ES2720525T3 (es) | 2014-10-16 | 2019-07-22 | Bayer Pharma AG | Derivados fluorados de benzofuranil-pirimidina que contienen un grupo sulfona |
| 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 |
| US20180050040A1 (en) | 2015-03-24 | 2018-02-22 | Bayer Pharma Aktiengesellschaft | Use of 4-(4-fluoro-2-methoxyphenyl)-n--1,3,5-triazin-2-amine for treating lymphomas |
| 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 |
| ME03404B (me) | 2015-06-29 | 2020-01-20 | Astrazeneca Ab | Derivati policikličnih amida kao cdk9 inhibitori |
| ES2786552T3 (es) | 2015-09-29 | 2020-10-13 | Bayer Pharma AG | Compuestos de sulfondiimina macrocíclicos nuevos |
| EP3359544B1 (en) | 2015-10-08 | 2020-08-12 | Bayer Pharma Aktiengesellschaft | Novel modified macrocyclic compounds |
| WO2017060322A2 (en) | 2015-10-10 | 2017-04-13 | Bayer Pharma Aktiengesellschaft | Ptefb-inhibitor-adc |
| BR112019000796A2 (pt) | 2016-07-16 | 2019-04-24 | Florida State University Research Foundation, Inc. | compostos e métodos para tratamento e prevenção da infecção flavivirus |
| WO2018177889A1 (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 |
| US11149047B2 (en) | 2017-10-30 | 2021-10-19 | Aptose Biosciences, Inc. | Aryl imidazoles for treatment of cancer |
| IL276437B2 (en) | 2018-02-13 | 2024-03-01 | Bayer Ag | Use of 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-n-{4-[(s-methylsulfonimidoyl)methyl]pyridin-2-yl}pyridin-2-amine for treating diffuse large b-cell lymphoma |
| US20220226341A1 (en) * | 2019-05-23 | 2022-07-21 | Kyoto University | Pharmaceutical Composition for Alzheimer's Disease |
| 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 |
| CN100355751C (zh) | 2000-03-29 | 2007-12-19 | 西克拉塞尔有限公司 | 2－取代的4－杂芳基－嘧啶、其组合物及其用途 |
| ES2292753T4 (es) | 2001-03-29 | 2009-02-16 | Vertex Pharmaceuticals Incorporated | Inhibidores de quinasas n-terminales c-jun (jnk) y otras proteina quinasas. |
| 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 |
| EP1648877A1 (en) | 2003-07-22 | 2006-04-26 | Neurogen Corporation | Substituted pyridin-2-ylamine analogues |
| AU2004261484A1 (en) | 2003-07-30 | 2005-02-10 | Cyclacel Limited | 2-aminophenyl-4-phenylpyrimidines as kinase inhibitors |
| 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 |
| US20090221581A1 (en) * | 2005-05-25 | 2009-09-03 | Philipp Wabnitz | Methods of treating pain |
| US8389521B2 (en) * | 2007-04-24 | 2013-03-05 | Ingenium Pharmaceuticals Gmbh | Inhibitors of protein kinases |
| US8507511B2 (en) * | 2007-04-24 | 2013-08-13 | Ingenium Pharmaceuticals Gmbh | Inhibitors of protein kinases |
| ES2539518T3 (es) * | 2007-04-24 | 2015-07-01 | Astrazeneca Ab | Inhibidores de proteínas quinasas |
-
2008
- 2008-04-24 WO PCT/EP2008/055017 patent/WO2008129080A1/en not_active Ceased
- 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 EP EP08749710A patent/EP2137166B1/en not_active Not-in-force
-
2013
- 2013-08-12 US US13/964,814 patent/US20130338147A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010525025A5 (index.php) | ||
| JP2011502956A5 (index.php) | ||
| JP2004536814A5 (index.php) | ||
| RU2412937C2 (ru) | Соединения трехзамещенного амина и их применение в качестве ингибиторов белка переноса холестерилового эфира (сетр) | |
| HRP20241159T1 (hr) | Heterociklički agonisti za glp-1 | |
| JP2020023577A5 (index.php) | ||
| RU2013148405A (ru) | Ингибиторы киназ | |
| KR20090128478A (ko) | 페닐 아미노 피리미딘 화합물 및 이의 용도 | |
| RU2016115803A (ru) | Замещенные никотинимидные ингибиторы втк, их получение и применение в терапии раковых, воспалительных и аутоиммунных заболеваний | |
| RU2006146985A (ru) | Модуляторы мускариновых рецепторов | |
| HUT67636A (en) | New sulfonylamino-pyrimidines and pharmaceutical compositions containing them | |
| JP2009541268A5 (index.php) | ||
| JP2020529405A5 (index.php) | ||
| RU2007101236A (ru) | Новые гидантоиновые производные для лечения обструктивных заболеваний дыхательных путей | |
| JP2011519854A5 (index.php) | ||
| JP2007504160A5 (index.php) | ||
| JP2013523803A5 (index.php) | ||
| JP2016512844A5 (index.php) | ||
| JP2011523646A5 (index.php) | ||
| RU2009101911A (ru) | Производные пиридина и пиразина в качестве ингибиторов mnk-киназы | |
| JP2017515836A5 (index.php) | ||
| ME02763B (me) | Derivati bipirazola kao inhibitori jak | |
| RU2009133846A (ru) | Новые производные гидантоина в качестве ингибиторов металлопротеиназ | |
| JP2010513272A5 (index.php) | ||
| RU2413726C2 (ru) | Замещенные биарильные аналоги пиперазинилпиридина, их применение в терапии, фармацевтическая композиция, фармацевтический препарат, способы уменьшения проводимости кальция и ингибирования связывания капсаициновых рецепторов |