JP2015519307A5

JP2015519307A5 -

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Publication number: JP2015519307A5
Authority: JP; Japan
Prior art keywords: compound; amino; ylamino; fluoro; dimethyloctahydroindolizin
Prior art date: 2013-04-04
Legal status : Granted

Application number

JP2015504725A

Other languages

English (en)

Japanese (ja)

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JP6113828B2 (ja

JP2015519307A (ja

Filing date

2013-04-04

Publication date

2016-06-02

2013-04-04 Application filed filed Critical

2013-04-04 Priority claimed from PCT/US2013/035285 external-priority patent/WO2013152198A1/en

2015-07-09 Publication of JP2015519307A publication Critical patent/JP2015519307A/ja

2016-06-02 Publication of JP2015519307A5 publication Critical patent/JP2015519307A5/ja

2017-04-12 Application granted granted Critical

2017-04-12 Publication of JP6113828B2 publication Critical patent/JP6113828B2/ja

Status Expired - Fee Related legal-status Critical Current

2033-04-04 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims 244
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 51
-1 amino, substituted amino Chemical group 0.000 claims 28
YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
125000004043 oxo group Chemical group O=* 0.000 claims 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 claims 8
125000000217 alkyl group Chemical group 0.000 claims 7
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 7
229910052736 halogen Inorganic materials 0.000 claims 7
150000002367 halogens Chemical class 0.000 claims 7
125000000547 substituted alkyl group Chemical group 0.000 claims 7
125000001072 heteroaryl group Chemical group 0.000 claims 6
229910052739 hydrogen Inorganic materials 0.000 claims 6
150000002431 hydrogen Chemical class 0.000 claims 6
239000001257 hydrogen Substances 0.000 claims 6
125000005309 thioalkoxy group Chemical group 0.000 claims 6
125000002252 acyl group Chemical group 0.000 claims 5
125000000266 alpha-aminoacyl group Chemical group 0.000 claims 5
125000004093 cyano group Chemical group *C#N 0.000 claims 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 5
102000003923 Protein Kinase C Human genes 0.000 claims 4
108090000315 Protein Kinase C Proteins 0.000 claims 4
125000003545 alkoxy group Chemical group 0.000 claims 4
125000003118 aryl group Chemical group 0.000 claims 4
201000010099 disease Diseases 0.000 claims 4
208000035475 disorder Diseases 0.000 claims 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
125000005415 substituted alkoxy group Chemical group 0.000 claims 4
PWDDRWHQJQYYAK-MSOLQXFVSA-N 3-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(tetrazol-1-yl)phenoxy]propan-1-ol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=C(OCCCO)C=1N1C=NN=N1 PWDDRWHQJQYYAK-MSOLQXFVSA-N 0.000 claims 3
XHCBBQOBCSQZKL-UHFFFAOYSA-N 7-[[2-[4-cyclopropyl-2-fluoro-5-(4-methyl-5-oxotetrazol-1-yl)anilino]-5-fluoropyrimidin-4-yl]amino]-5,5-dimethyl-1,2,6,7,8,8a-hexahydroindolizin-3-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(NC3CC(C)(C)N4C(=O)CCC4C3)C(F)=CN=2)=C(F)C=C1C1CC1 XHCBBQOBCSQZKL-UHFFFAOYSA-N 0.000 claims 3
ZQACGONEYXBNEW-KGLIPLIRSA-N O1CC(=O)NC2=C1C=CC=C2NC1=NC=C(F)C(N[C@H]2CC(N3CCC[C@H]3C2)(C)C)=N1 Chemical compound O1CC(=O)NC2=C1C=CC=C2NC1=NC=C(F)C(N[C@H]2CC(N3CCC[C@H]3C2)(C)C)=N1 ZQACGONEYXBNEW-KGLIPLIRSA-N 0.000 claims 3
230000000694 effects Effects 0.000 claims 3
150000003573 thiols Chemical class 0.000 claims 3
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 2
VXTYPJFMGAKVJO-UHFFFAOYSA-N 1-[5-[[4-[(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]-5-fluoropyrimidin-2-yl]amino]-2-(oxan-4-yloxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(NC3CC(C)(C)N4CCCC4C3)C(F)=CN=2)=CC=C1OC1CCOCC1 VXTYPJFMGAKVJO-UHFFFAOYSA-N 0.000 claims 2
HIJUKDHGAOXGAM-UHFFFAOYSA-N 1-[5-[[4-[(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]-5-fluoropyrimidin-2-yl]amino]-2-(oxetan-3-yloxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(NC3CC(C)(C)N4CCCC4C3)C(F)=CN=2)=CC=C1OC1COC1 HIJUKDHGAOXGAM-UHFFFAOYSA-N 0.000 claims 2
LDUSGAYKQIOKIX-CTWPCTMYSA-N 1-[5-[[4-[(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]-5-fluoropyrimidin-2-yl]amino]-2-[(3r)-oxolan-3-yl]oxyphenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(NC3CC(C)(C)N4CCCC4C3)C(F)=CN=2)=CC=C1O[C@H]1COCC1 LDUSGAYKQIOKIX-CTWPCTMYSA-N 0.000 claims 2
LDUSGAYKQIOKIX-ACBHZAAOSA-N 1-[5-[[4-[(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]-5-fluoropyrimidin-2-yl]amino]-2-[(3s)-oxolan-3-yl]oxyphenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(NC3CC(C)(C)N4CCCC4C3)C(F)=CN=2)=CC=C1O[C@@H]1COCC1 LDUSGAYKQIOKIX-ACBHZAAOSA-N 0.000 claims 2
MRJRFBFEOKPCKB-CABCVRRESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(2-aminoethoxy)-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCCN MRJRFBFEOKPCKB-CABCVRRESA-N 0.000 claims 2
JFAIVAMGMCTLMH-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1C1CC1 JFAIVAMGMCTLMH-CVEARBPZSA-N 0.000 claims 2
VNLANJHTNDZABY-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methoxyphenyl]-4-methyltetrazol-5-one Chemical compound COC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O VNLANJHTNDZABY-CVEARBPZSA-N 0.000 claims 2
SITBLSOUBBQNAT-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methylphenyl]-4-methyltetrazol-5-one Chemical compound CC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O SITBLSOUBBQNAT-SJORKVTESA-N 0.000 claims 2
VBVITBNLMMIWGW-JAIYHHTPSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(2-hydroxypropoxy)phenyl]-4-methyltetrazol-5-one Chemical compound CC(O)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O VBVITBNLMMIWGW-JAIYHHTPSA-N 0.000 claims 2
HIDRHKGFFJSWEF-MOPGFXCFSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(oxan-4-ylmethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCC1CCOCC1 HIDRHKGFFJSWEF-MOPGFXCFSA-N 0.000 claims 2
DAJYCZLHWNYIPA-SJORKVTESA-N 2-[1-[3-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]phenyl]tetrazol-5-yl]sulfanylethanol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1N1N=NN=C1SCCO DAJYCZLHWNYIPA-SJORKVTESA-N 0.000 claims 2
FCECZAULLRIOJJ-UHFFFAOYSA-N 4-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-1H-pyrimidine-2,4-diamine Chemical compound N1C(N)=NC=CC1(N)C1CC2CCCN2CC1 FCECZAULLRIOJJ-UHFFFAOYSA-N 0.000 claims 2
XMMQZBAIAYQGFP-UHFFFAOYSA-N 4-(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1H-indolizin-7-yl)-1H-pyrimidine-2,4-diamine Chemical compound C1C2CCCN2C(C)(C)CC1C1(N)NC(N)=NC=C1 XMMQZBAIAYQGFP-UHFFFAOYSA-N 0.000 claims 2
AWHZRXVLAQWJLE-MSOLQXFVSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[4,4-bis(methoxymethyl)tetrazolo[5,1-c][1,4]benzoxazin-8-yl]-5-fluoropyrimidine-2,4-diamine Chemical compound C1[C@@H]2CCCN2C(C)(C)C[C@@H]1NC1=NC(NC2=CC=C3OC(C4=NN=NN4C3=C2)(COC)COC)=NC=C1F AWHZRXVLAQWJLE-MSOLQXFVSA-N 0.000 claims 2
OTPWEBUGLWNXLO-SOAGJPPSSA-N 5-[[4-[(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]-5-fluoropyrimidin-2-yl]amino]-2-[(3r)-oxolan-3-yl]oxybenzonitrile Chemical compound C1C2CCCN2C(C)(C)CC1NC(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1O[C@@H]1CCOC1 OTPWEBUGLWNXLO-SOAGJPPSSA-N 0.000 claims 2
OTPWEBUGLWNXLO-MHJFOBGBSA-N 5-[[4-[(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]-5-fluoropyrimidin-2-yl]amino]-2-[(3s)-oxolan-3-yl]oxybenzonitrile Chemical compound C1C2CCCN2C(C)(C)CC1NC(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1O[C@H]1CCOC1 OTPWEBUGLWNXLO-MHJFOBGBSA-N 0.000 claims 2
ICJQVSAYHUGWMQ-RJBLSPETSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(1,1,2,2-tetradeuterio-2-hydroxyethoxy)benzonitrile Chemical compound C1=C(C#N)C(OC([2H])([2H])C([2H])(O)[2H])=CC=C1NC1=NC=C(F)C(N[C@H]2CC(C)(C)N3CCC[C@H]3C2)=N1 ICJQVSAYHUGWMQ-RJBLSPETSA-N 0.000 claims 2
VWAMICUZLIDILJ-UHFFFAOYSA-N 5-fluoro-2-n-[4-fluoro-3-(5-methyltetrazol-1-yl)phenyl]-4-n-(5,5,8-trimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)pyrimidine-2,4-diamine Chemical compound CC1C2CCCN2C(C)(C)CC1NC(C(=CN=1)F)=NC=1NC(C=1)=CC=C(F)C=1N1N=NN=C1C VWAMICUZLIDILJ-UHFFFAOYSA-N 0.000 claims 2
JKWWNCXYPDZBEU-OLZOCXBDSA-N 5-n-[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]-6-fluoro-2-n-methyl-1,3-benzoxazole-2,5-diamine Chemical compound C1[C@@H]2CCCN2C(C)(C)C[C@@H]1NC1=NC(NC=2C=C3N=C(OC3=CC=2F)NC)=NC=C1F JKWWNCXYPDZBEU-OLZOCXBDSA-N 0.000 claims 2
229940126657 Compound 17 Drugs 0.000 claims 2
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 2
125000004442 acylamino group Chemical group 0.000 claims 2
125000004423 acyloxy group Chemical group 0.000 claims 2
125000000033 alkoxyamino group Chemical group 0.000 claims 2
125000004104 aryloxy group Chemical group 0.000 claims 2
150000001540 azides Chemical class 0.000 claims 2
239000012472 biological sample Substances 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
125000004181 carboxyalkyl group Chemical group 0.000 claims 2
150000003840 hydrochlorides Chemical class 0.000 claims 2
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 2
MCOMGGLTFKWEOA-UHFFFAOYSA-N oxazepin-4-ol Chemical compound O1N=CC(=CC=C1)O MCOMGGLTFKWEOA-UHFFFAOYSA-N 0.000 claims 2
125000005255 oxyaminoacyl group Chemical group 0.000 claims 2
125000003107 substituted aryl group Chemical group 0.000 claims 2
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
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
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
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
OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-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
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
VPYYHGPTUNNIPM-UHFFFAOYSA-N 1-[2-cyclopropyl-4-fluoro-5-[[5-fluoro-4-[(5,5,8-trimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]pyrimidin-2-yl]amino]phenyl]-4-methyltetrazol-5-one Chemical compound CC1C2CCCN2C(C)(C)CC1NC(C(=CN=1)F)=NC=1NC(C(=C1)F)=CC(N2C(N(C)N=N2)=O)=C1C1CC1 VPYYHGPTUNNIPM-UHFFFAOYSA-N 0.000 claims 1
JVDSTZXFZUGLAF-UHFFFAOYSA-N 1-[2-cyclopropyl-5-[2-[4-[2-(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)hydrazinyl]-5-fluoropyrimidin-2-yl]hydrazinyl]-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NNC=2N=C(NNC3CC(C)(C)N4CCCC4C3)C(F)=CN=2)=C(F)C=C1C1CC1 JVDSTZXFZUGLAF-UHFFFAOYSA-N 0.000 claims 1
YMPMUCHDYTYALL-UHFFFAOYSA-N 1-[2-cyclopropyl-5-[[4-[(3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]-5-fluoropyrimidin-2-yl]amino]-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(NC3CC4N(C(CC4)(C)C)CC3)C(F)=CN=2)=C(F)C=C1C1CC1 YMPMUCHDYTYALL-UHFFFAOYSA-N 0.000 claims 1
IEGMICGTLJXRTN-CABCVRRESA-N 1-[3-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]phenyl]-2h-tetrazol-5-one Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1N1N=NNC1=O IEGMICGTLJXRTN-CABCVRRESA-N 0.000 claims 1
LECGFLMTZXWVKM-CABCVRRESA-N 1-[3-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]phenyl]-2h-tetrazole-5-thione Chemical class N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1N1N=NN=C1S LECGFLMTZXWVKM-CABCVRRESA-N 0.000 claims 1
VDWXALTYAMHPDS-SJORKVTESA-N 1-[3-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]phenyl]-4-(2-hydroxyethyl)tetrazol-5-one Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1N1N=NN(CCO)C1=O VDWXALTYAMHPDS-SJORKVTESA-N 0.000 claims 1
LDBVTSFNEALJDF-SJORKVTESA-N 1-[3-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]phenyl]-4-(oxetan-3-yl)tetrazol-5-one Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1N(C1=O)N=NN1C1COC1 LDBVTSFNEALJDF-SJORKVTESA-N 0.000 claims 1
HRJQIEYESSEMGH-KVJCIMDZSA-N 1-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(tetrazol-1-yl)phenoxy]propan-2-ol Chemical compound CC(O)COC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1C=NN=N1 HRJQIEYESSEMGH-KVJCIMDZSA-N 0.000 claims 1
UFQPPSMJKRZPBN-CVEARBPZSA-N 1-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(trifluoromethyl)phenyl]azetidin-3-ol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C(F)(F)F)=CC=C1N1CC(O)C1 UFQPPSMJKRZPBN-CVEARBPZSA-N 0.000 claims 1
HTLXZMBFPMJVHV-HOTGVXAUSA-N 1-[4-[[4-[[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(difluoromethoxy)phenyl]azetidin-3-ol Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1OC(F)F)=CC=C1N1CC(O)C1 HTLXZMBFPMJVHV-HOTGVXAUSA-N 0.000 claims 1
CQWAILPSZVCBCM-OAGGEKHMSA-N 1-[5-[[4-[[(2r,7r,8ar)-2-fluoro-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4C[C@H](F)C[C@H]4C3)C(F)=CN=2)=C(F)C=C1C1CC1 CQWAILPSZVCBCM-OAGGEKHMSA-N 0.000 claims 1
RRKBAAMUKUDNPY-BZUAXINKSA-N 1-[5-[[4-[[(2r,7r,8ar)-2-hydroxy-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4C[C@H](O)C[C@H]4C3)C(F)=CN=2)=C(F)C=C1C1CC1 RRKBAAMUKUDNPY-BZUAXINKSA-N 0.000 claims 1
CQWAILPSZVCBCM-PMPSAXMXSA-N 1-[5-[[4-[[(2r,7s,8ar)-2-fluoro-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@@H]3CC(C)(C)N4C[C@H](F)C[C@H]4C3)C(F)=CN=2)=C(F)C=C1C1CC1 CQWAILPSZVCBCM-PMPSAXMXSA-N 0.000 claims 1
CQWAILPSZVCBCM-XHSDSOJGSA-N 1-[5-[[4-[[(2s,7r,8ar)-2-fluoro-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4C[C@@H](F)C[C@H]4C3)C(F)=CN=2)=C(F)C=C1C1CC1 CQWAILPSZVCBCM-XHSDSOJGSA-N 0.000 claims 1
MRPPCAXBPQTACM-OLZOCXBDSA-N 1-[5-[[4-[[(7R,8aS)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1H-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-4-fluoro-2-hydroxyphenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)=C(F)C=C1O MRPPCAXBPQTACM-OLZOCXBDSA-N 0.000 claims 1
RSYAOTAOWSFUSI-JCGOAIGOSA-N 1-[5-[[4-[[(7R,8aS)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1H-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(1,1,2,2-tetradeuterio-2-hydroxyethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound [2H]C([2H])(O)C([2H])([2H])Oc1cc(F)c(Nc2ncc(F)c(N[C@@H]3C[C@@H]4CCCN4C(C)(C)C3)n2)cc1-n1nnn(C)c1=O RSYAOTAOWSFUSI-JCGOAIGOSA-N 0.000 claims 1
YFDNDTKEMZBVNX-CVEARBPZSA-N 1-[5-[[4-[[(7R,8aS)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1H-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(2-methoxyethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound COCCOC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O YFDNDTKEMZBVNX-CVEARBPZSA-N 0.000 claims 1
XHWCBFSCZUJKQJ-KBZJNTCOSA-N 1-[5-[[4-[[(7S,8aS)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1H-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(1-deuterio-3-hydroxycyclobutyl)oxyphenyl]-4-methyltetrazol-5-one Chemical compound [2H]C1(CC(O)C1)Oc1ccc(Nc2ncc(F)c(N[C@H]3CCN4[C@@H](CCC4(C)C)C3)n2)cc1-n1nnn(C)c1=O XHWCBFSCZUJKQJ-KBZJNTCOSA-N 0.000 claims 1
KXTUEBXYMDBGJS-HUUCEWRRSA-N 1-[5-[[4-[[(7r,8ar)-2,2-difluoro-5,5-dimethyl-1,3,6,7,8,8a-hexahydroindolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CC(F)(F)C[C@H]4C3)C(F)=CN=2)=C(F)C=C1C1CC1 KXTUEBXYMDBGJS-HUUCEWRRSA-N 0.000 claims 1
FPSFRDVHTGFKDS-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)=C(F)C=C1C1CC1 FPSFRDVHTGFKDS-CVEARBPZSA-N 0.000 claims 1
DHXBBYDGQZQXKU-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-4-fluoro-2-(2-hydroxy-2-methylpropoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)=C(F)C=C1OCC(C)(C)O DHXBBYDGQZQXKU-CVEARBPZSA-N 0.000 claims 1
AWBHALPAYVXPAL-CABCVRRESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-4-fluoro-2-(2-hydroxyethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)=C(F)C=C1OCCO AWBHALPAYVXPAL-CABCVRRESA-N 0.000 claims 1
HTSLJDMDEMNGEP-JAIYHHTPSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-4-fluoro-2-(2-hydroxypropoxy)phenyl]-4-methyltetrazol-5-one Chemical compound CC(O)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)C=C1N1N=NN(C)C1=O HTSLJDMDEMNGEP-JAIYHHTPSA-N 0.000 claims 1
HTSLJDMDEMNGEP-XHSDSOJGSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-4-fluoro-2-[(2s)-2-hydroxypropoxy]phenyl]-4-methyltetrazol-5-one Chemical compound C[C@H](O)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)C=C1N1N=NN(C)C1=O HTSLJDMDEMNGEP-XHSDSOJGSA-N 0.000 claims 1
UXXQMRDQKHHTEK-BBWFWOEESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-4-fluoro-2-[(2s)-2-methoxypropoxy]phenyl]-4-methyltetrazol-5-one Chemical compound CO[C@@H](C)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)C=C1N1N=NN(C)C1=O UXXQMRDQKHHTEK-BBWFWOEESA-N 0.000 claims 1
IGAANKJZCYFVQM-DVKDBIPTSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(1,4-dioxan-2-ylmethoxy)-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCC1OCCOC1 IGAANKJZCYFVQM-DVKDBIPTSA-N 0.000 claims 1
AYKYNMLUJYMTOD-YSPPHNQVSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(2,3-dihydroxypropoxy)-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCC(O)CO AYKYNMLUJYMTOD-YSPPHNQVSA-N 0.000 claims 1
NIUNOKKILDDXJQ-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(2-hydroxyethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=CC=C1OCCO NIUNOKKILDDXJQ-SJORKVTESA-N 0.000 claims 1
AYKYNMLUJYMTOD-OWCLPIDISA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-[(2r)-2,3-dihydroxypropoxy]-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OC[C@H](O)CO AYKYNMLUJYMTOD-OWCLPIDISA-N 0.000 claims 1
JPJHGCNSYBGKQJ-MOPGFXCFSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-[2-(diethylamino)ethoxy]-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound CCN(CC)CCOC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O JPJHGCNSYBGKQJ-MOPGFXCFSA-N 0.000 claims 1
DBJAVKKLRILSIN-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-[2-(dimethylamino)ethoxy]-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound CN(C)CCOC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O DBJAVKKLRILSIN-SJORKVTESA-N 0.000 claims 1
VIUMVNLYLZGPMY-RTWAWAEBSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-[4-(oxetan-3-yl)piperazin-1-yl]phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=CC=C1N1CCN(C2COC2)CC1 VIUMVNLYLZGPMY-RTWAWAEBSA-N 0.000 claims 1
DIBPQHOPOFDJIP-OLZOCXBDSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-bromo-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1Br DIBPQHOPOFDJIP-OLZOCXBDSA-N 0.000 claims 1
NMZYPNYNOCKYOS-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-ethenyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1C=C NMZYPNYNOCKYOS-CVEARBPZSA-N 0.000 claims 1
QLFDTSGRRHTPAW-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-ethyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound CCC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O QLFDTSGRRHTPAW-CVEARBPZSA-N 0.000 claims 1
MKUXZIVTVWDJFC-CABCVRRESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methoxyphenyl]-2h-tetrazol-5-one Chemical compound COC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NNC1=O MKUXZIVTVWDJFC-CABCVRRESA-N 0.000 claims 1
IFXOWFMPASNIHV-MSOLQXFVSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methoxyphenyl]-4-(2-hydroxy-2-methylpropyl)tetrazol-5-one Chemical compound COC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(CC(C)(C)O)C1=O IFXOWFMPASNIHV-MSOLQXFVSA-N 0.000 claims 1
NZFDRBYUDMGIMU-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methoxyphenyl]-4-(2-hydroxyethyl)tetrazol-5-one Chemical compound COC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(CCO)C1=O NZFDRBYUDMGIMU-SJORKVTESA-N 0.000 claims 1
GAZDVEPTZVODIV-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methoxyphenyl]-4-(oxetan-3-yl)tetrazol-5-one Chemical compound COC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N(C1=O)N=NN1C1COC1 GAZDVEPTZVODIV-SJORKVTESA-N 0.000 claims 1
MLBBRZXTASACOG-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methylphenyl]-2h-tetrazol-5-one Chemical compound CC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NNC1=O MLBBRZXTASACOG-CVEARBPZSA-N 0.000 claims 1
VTTZBKSZYLYKMO-MOPGFXCFSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methylphenyl]-4-(2-hydroxy-2-methylpropyl)tetrazol-5-one Chemical compound CC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(CC(C)(C)O)C1=O VTTZBKSZYLYKMO-MOPGFXCFSA-N 0.000 claims 1
WQRDIEJQTCEGHC-MSOLQXFVSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methylphenyl]-4-(2-hydroxyethyl)tetrazol-5-one Chemical compound CC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(CCO)C1=O WQRDIEJQTCEGHC-MSOLQXFVSA-N 0.000 claims 1
RJRYGUYWFUAVBS-MSOLQXFVSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methylphenyl]-4-(oxetan-3-yl)tetrazol-5-one Chemical compound CC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N(C1=O)N=NN1C1COC1 RJRYGUYWFUAVBS-MSOLQXFVSA-N 0.000 claims 1
VMAOEDCJABWXBK-DMJDIKPUSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(1-hydroxyethyl)phenyl]-4-methyltetrazol-5-one Chemical compound CC(O)C1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O VMAOEDCJABWXBK-DMJDIKPUSA-N 0.000 claims 1
KEWWCXJSVKMSKB-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(2-fluoro-2-methylpropoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCC(C)(C)F KEWWCXJSVKMSKB-CVEARBPZSA-N 0.000 claims 1
COSMFIFRYYAXRF-CABCVRRESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(2-fluoroethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCCF COSMFIFRYYAXRF-CABCVRRESA-N 0.000 claims 1
RSYAOTAOWSFUSI-CABCVRRESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(2-hydroxyethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCCO RSYAOTAOWSFUSI-CABCVRRESA-N 0.000 claims 1
PPLQXWLAQKLJMY-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(2-hydroxyethyl)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1CCO PPLQXWLAQKLJMY-CVEARBPZSA-N 0.000 claims 1
XEHHETQZLHRHFY-MOPGFXCFSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(2-morpholin-4-ylethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCCN1CCOCC1 XEHHETQZLHRHFY-MOPGFXCFSA-N 0.000 claims 1
WSEGUELEIBKHRX-FKTKBCEVSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(2-oxooxolan-3-yl)oxyphenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OC1C(=O)OCC1 WSEGUELEIBKHRX-FKTKBCEVSA-N 0.000 claims 1
DSJDTYYVDJDUBW-NTCUHZHNSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(3,3,3-trifluoro-2-hydroxypropoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCC(O)C(F)(F)F DSJDTYYVDJDUBW-NTCUHZHNSA-N 0.000 claims 1
XDMBZOIYMOYKSK-XNIRIUNOSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(3-hydroxycyclobutyl)oxyphenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OC1CC(O)C1 XDMBZOIYMOYKSK-XNIRIUNOSA-N 0.000 claims 1
SNQYVACNZUUNLD-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(3-hydroxyprop-1-ynyl)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1C#CCO SNQYVACNZUUNLD-SJORKVTESA-N 0.000 claims 1
CVBYXRJFBCJMHS-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(3-hydroxypropyl)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1CCCO CVBYXRJFBCJMHS-SJORKVTESA-N 0.000 claims 1
BDJKZYQBQLSRML-CZKGODDJSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(3-phenylmethoxycyclobutyl)oxyphenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OC1CC(OCC=2C=CC=CC=2)C1 BDJKZYQBQLSRML-CZKGODDJSA-N 0.000 claims 1
XPMFITJGZVFVNF-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(oxan-4-yloxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OC1CCOCC1 XPMFITJGZVFVNF-SJORKVTESA-N 0.000 claims 1
SGAWXOINZRUAHZ-GARXDOFDSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(oxetan-2-ylmethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCC1OCC1 SGAWXOINZRUAHZ-GARXDOFDSA-N 0.000 claims 1
NGQLXQUPIYIQGA-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-(oxetan-3-ylmethoxy)phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCC1COC1 NGQLXQUPIYIQGA-SJORKVTESA-N 0.000 claims 1
QIESGLGAMPXIEE-OAGGEKHMSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-[(2r)-1-hydroxypropan-2-yl]oxyphenyl]-4-methyltetrazol-5-one Chemical compound OC[C@@H](C)OC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O QIESGLGAMPXIEE-OAGGEKHMSA-N 0.000 claims 1
YTWWCSDRAJHZBV-OAGGEKHMSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-[(2r)-2-fluoropropoxy]phenyl]-4-methyltetrazol-5-one Chemical compound C[C@@H](F)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O YTWWCSDRAJHZBV-OAGGEKHMSA-N 0.000 claims 1
DMNOXFBJPGWPLO-ZACQAIPSSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-[(2r)-3-hydroxy-2-methylpropoxy]phenyl]-4-methyltetrazol-5-one Chemical compound OC[C@@H](C)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O DMNOXFBJPGWPLO-ZACQAIPSSA-N 0.000 claims 1
YTWWCSDRAJHZBV-XHSDSOJGSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-[(2s)-2-fluoropropoxy]phenyl]-4-methyltetrazol-5-one Chemical compound C[C@H](F)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O YTWWCSDRAJHZBV-XHSDSOJGSA-N 0.000 claims 1
XQXKNFTVHWDBBI-BBWFWOEESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-[(2s)-2-methoxypropoxy]phenyl]-4-methyltetrazol-5-one Chemical compound CO[C@@H](C)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O XQXKNFTVHWDBBI-BBWFWOEESA-N 0.000 claims 1
KXZXVBZTQFGGQP-SJORKVTESA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-[(3-methyloxetan-3-yl)methoxy]phenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCC1(C)COC1 KXZXVBZTQFGGQP-SJORKVTESA-N 0.000 claims 1
WHKQTJGESNASRF-IXDOHACOSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-[(3r)-oxolan-3-yl]oxyphenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1O[C@H]1COCC1 WHKQTJGESNASRF-IXDOHACOSA-N 0.000 claims 1
WHKQTJGESNASRF-IKGGRYGDSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-[(3s)-oxolan-3-yl]oxyphenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1O[C@@H]1COCC1 WHKQTJGESNASRF-IKGGRYGDSA-N 0.000 claims 1
URMRVFQNASQIQK-MSOLQXFVSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-[2-(2-methoxyethoxy)ethoxy]phenyl]-4-methyltetrazol-5-one Chemical compound COCCOCCOC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O URMRVFQNASQIQK-MSOLQXFVSA-N 0.000 claims 1
FJBPBBUHADXTHW-KGLIPLIRSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-methoxyphenyl]-4-methyltetrazol-5-one Chemical compound COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O FJBPBBUHADXTHW-KGLIPLIRSA-N 0.000 claims 1
NIAPQRFFZKSUBZ-CVEARBPZSA-N 1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-4-fluoro-2-propan-2-yloxyphenyl]-4-methyltetrazol-5-one Chemical compound CC(C)OC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN(C)C1=O NIAPQRFFZKSUBZ-CVEARBPZSA-N 0.000 claims 1
KXTUEBXYMDBGJS-LSDHHAIUSA-N 1-[5-[[4-[[(7s,8ar)-2,2-difluoro-5,5-dimethyl-1,3,6,7,8,8a-hexahydroindolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@@H]3CC(C)(C)N4CC(F)(F)C[C@H]4C3)C(F)=CN=2)=C(F)C=C1C1CC1 KXTUEBXYMDBGJS-LSDHHAIUSA-N 0.000 claims 1
JFAIVAMGMCTLMH-JKSUJKDBSA-N 1-[5-[[4-[[(7s,8ar)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorophenyl]-4-methyltetrazol-5-one Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@@H]3CC(C)(C)N4CCC[C@@H]4C3)C(F)=CN=2)=C(F)C=C1C1CC1 JFAIVAMGMCTLMH-JKSUJKDBSA-N 0.000 claims 1
JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims 1
AOKKGXXYBPBKDR-UHFFFAOYSA-N 1-methyl-2h-tetrazol-5-one Chemical compound CN1N=NN=C1O AOKKGXXYBPBKDR-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
BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 claims 1
QTMAZYGAVHCKKX-UHFFFAOYSA-N 2-[(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]propane-1,3-diol Chemical compound NC1=NC=NC2=C1C(Br)=CN2COC(CO)CO QTMAZYGAVHCKKX-UHFFFAOYSA-N 0.000 claims 1
NEDOHBXLGMQSTE-FQZXCLDYSA-N 2-[1-[3-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]phenyl]tetrazol-5-yl]sulfanyl-3-aminopropan-1-ol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1N1N=NN=C1SC(CN)CO NEDOHBXLGMQSTE-FQZXCLDYSA-N 0.000 claims 1
WWWLUWIVMXIHCY-SJORKVTESA-N 2-[1-[3-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]phenyl]tetrazol-5-yl]sulfanylpropane-1,3-diol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1N1N=NN=C1SC(CO)CO WWWLUWIVMXIHCY-SJORKVTESA-N 0.000 claims 1
OEDSOUVBWXYGOW-MSOLQXFVSA-N 2-[1-[5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methylphenyl]tetrazol-5-yl]sulfanylethanol Chemical compound CC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN=C1SCCO OEDSOUVBWXYGOW-MSOLQXFVSA-N 0.000 claims 1
XMMPEYGIVYNXBJ-NCEMTQIISA-N 2-[4-[[4-[[(7R,8aS)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1H-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methoxyphenoxy]-1,1,2,2-tetradeuterioethanol Chemical compound [2H]C([2H])(O)C([2H])([2H])Oc1ccc(Nc2ncc(F)c(N[C@@H]3C[C@@H]4CCCN4C(C)(C)C3)n2)cc1OC XMMPEYGIVYNXBJ-NCEMTQIISA-N 0.000 claims 1
VQLNPCVENYOMSA-SJORKVTESA-N 2-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-2-(tetrazol-1-yl)phenoxy]ethanol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)Cl)=NC=1NC(C=1)=CC=C(OCCO)C=1N1C=NN=N1 VQLNPCVENYOMSA-SJORKVTESA-N 0.000 claims 1
FNFXYCZPEYBTFZ-MOPGFXCFSA-N 2-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(5-cyclopropyltetrazol-1-yl)phenoxy]ethanol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=C(OCCO)C=1N1N=NN=C1C1CC1 FNFXYCZPEYBTFZ-MOPGFXCFSA-N 0.000 claims 1
MCQSXCUZQCQCKC-SJORKVTESA-N 2-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(tetrazol-1-yl)phenoxy]ethanol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=C(OCCO)C=1N1C=NN=N1 MCQSXCUZQCQCKC-SJORKVTESA-N 0.000 claims 1
JGXNSQJJWYRMBO-CVEARBPZSA-N 2-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(trifluoromethyl)phenoxy]ethanol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCCO)C(C(F)(F)F)=C1 JGXNSQJJWYRMBO-CVEARBPZSA-N 0.000 claims 1
HOYRVZXVOKKECL-CVEARBPZSA-N 2-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-chlorophenoxy]ethanol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCCO)C(Cl)=C1 HOYRVZXVOKKECL-CVEARBPZSA-N 0.000 claims 1
ZGONEAOARUJJOU-CVEARBPZSA-N 2-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-fluorophenoxy]ethanol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCCO)C(F)=C1 ZGONEAOARUJJOU-CVEARBPZSA-N 0.000 claims 1
XMMPEYGIVYNXBJ-SJORKVTESA-N 2-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methoxyphenoxy]ethanol Chemical compound C1=C(OCCO)C(OC)=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C1 XMMPEYGIVYNXBJ-SJORKVTESA-N 0.000 claims 1
ONDZJWHTUNKMBW-MSOLQXFVSA-N 2-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methylphenoxy]ethanol Chemical compound C1=C(OCCO)C(C)=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C1 ONDZJWHTUNKMBW-MSOLQXFVSA-N 0.000 claims 1
CUDCIIIEKCVLTD-HOTGVXAUSA-N 2-[4-[[4-[[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(difluoromethoxy)phenoxy]ethanol Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCCO)C(OC(F)F)=C1 CUDCIIIEKCVLTD-HOTGVXAUSA-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
NHKUNOAILIMEGP-XMKPYSNPSA-N 2-[[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(trifluoromethyl)anilino]methyl]-3-chloropropanamide Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(NCC(CCl)C(N)=O)C(C(F)(F)F)=C1 NHKUNOAILIMEGP-XMKPYSNPSA-N 0.000 claims 1
PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-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
NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 claims 1
WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims 1
NNRKOTVOYJLNEQ-LUPKZBJLSA-N 3-[4-[[4-[[(7S,8aS)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1H-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-chlorophenoxy]-3-deuteriocyclobutan-1-ol Chemical compound [H][C@@]12CCC(C)(C)N1CC[C@@H](C2)NC1=C(F)C=NC(NC2=CC(Cl)=C(OC3([2H])CC(O)C3)C=C2)=N1 NNRKOTVOYJLNEQ-LUPKZBJLSA-N 0.000 claims 1
ITDLXRDXBJEYDM-DVKDBIPTSA-N 3-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(tetrazol-1-yl)phenoxy]propane-1,2-diol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=C(OCC(O)CO)C=1N1C=NN=N1 ITDLXRDXBJEYDM-DVKDBIPTSA-N 0.000 claims 1
IAWHWJPTSFYWRO-KGLIPLIRSA-N 3-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-5-fluoro-2-(4-methyl-5-oxotetrazol-1-yl)phenoxy]-2-oxopropanoic acid Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OCC(=O)C(O)=O IAWHWJPTSFYWRO-KGLIPLIRSA-N 0.000 claims 1
LMHFXLYMMUYZKL-VYMRPNJYSA-N 3-[4-[[4-[[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(difluoromethoxy)phenoxy]cyclobutan-1-ol Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1OC(F)F)=CC=C1OC1CC(O)C1 LMHFXLYMMUYZKL-VYMRPNJYSA-N 0.000 claims 1
LQZYGKYSNUSUPP-IRXDYDNUSA-N 3-[4-[[4-[[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(difluoromethoxy)phenoxy]propan-1-ol Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCCCO)C(OC(F)F)=C1 LQZYGKYSNUSUPP-IRXDYDNUSA-N 0.000 claims 1
MYTBMDGUVASBIE-VYMRPNJYSA-N 3-[4-[[4-[[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(trifluoromethyl)phenoxy]cyclobutan-1-ol Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C(F)(F)F)=CC=C1OC1CC(O)C1 MYTBMDGUVASBIE-VYMRPNJYSA-N 0.000 claims 1
NNRKOTVOYJLNEQ-VYMRPNJYSA-N 3-[4-[[4-[[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-chlorophenoxy]cyclobutan-1-ol Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1Cl)=CC=C1OC1CC(O)C1 NNRKOTVOYJLNEQ-VYMRPNJYSA-N 0.000 claims 1
NRIZOVPQKMPULJ-SJORKVTESA-N 3-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)Cl)=NC=1NC1=CC=CC(C#N)=C1 NRIZOVPQKMPULJ-SJORKVTESA-N 0.000 claims 1
NFVUHUZDBRWATB-JKSUJKDBSA-N 3-[[4-[[(7s,8ar)-2,2-difluoro-5,5-dimethyl-1,3,6,7,8,8a-hexahydroindolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound C1=CC=C(C#N)C(C)=C1NC1=NC=C(F)C(N[C@@H]2CC(C)(C)N3CC(F)(F)C[C@H]3C2)=N1 NFVUHUZDBRWATB-JKSUJKDBSA-N 0.000 claims 1
USRIPHLDZDKOHR-AFFIPYLWSA-N 4-N-[(7S,8aS)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1H-indolizin-7-yl]-2-N-[3-chloro-4-(1-deuterio-3-phenylmethoxycyclobutyl)oxyphenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound [2H]C1(CC(C1)OCc1ccccc1)Oc1ccc(Nc2ncc(F)c(N[C@H]3CCN4[C@@H](CCC4(C)C)C3)n2)cc1Cl USRIPHLDZDKOHR-AFFIPYLWSA-N 0.000 claims 1
YLVJYBNHEAABJQ-OGQIYBCISA-N 4-[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-chlorophenoxy]piperidin-3-ol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1Cl)=CC=C1OC1CCNCC1O YLVJYBNHEAABJQ-OGQIYBCISA-N 0.000 claims 1
MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 claims 1
SWWIBEDKJRWWTJ-SJORKVTESA-N 4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-2-[2-fluoro-4-(2-fluoroethoxy)-5-(4-methyl-5-oxotetrazol-1-yl)anilino]pyrimidine-5-carbonitrile Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(C#N)=CN=2)=C(F)C=C1OCCF SWWIBEDKJRWWTJ-SJORKVTESA-N 0.000 claims 1
IPDNXEBPZBRHFI-NXHRZFHOSA-N 4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-2-[2-fluoro-4-[(2r)-2-hydroxypropoxy]-5-(4-methyl-5-oxotetrazol-1-yl)anilino]pyrimidine-5-carbonitrile Chemical compound C[C@@H](O)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(C#N)=CN=2)C=C1N1N=NN(C)C1=O IPDNXEBPZBRHFI-NXHRZFHOSA-N 0.000 claims 1
WODZHGUIZZEDRM-JQHSSLGASA-N 4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-2-[2-fluoro-4-[(2s)-2-fluoropropoxy]-5-(4-methyl-5-oxotetrazol-1-yl)anilino]pyrimidine-5-carbonitrile Chemical compound C[C@H](F)COC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(C#N)=CN=2)C=C1N1N=NN(C)C1=O WODZHGUIZZEDRM-JQHSSLGASA-N 0.000 claims 1
OOGVOIGJTLEYKZ-CABCVRRESA-N 4-[[4-[[(7R,8aS)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1H-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(5-cyclopropyltetrazol-1-yl)-5-fluorophenol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C(=CC=1O)F)=CC=1N1N=NN=C1C1CC1 OOGVOIGJTLEYKZ-CABCVRRESA-N 0.000 claims 1
FEMNSKHMPWTPHC-CABCVRRESA-N 4-[[4-[[(7R,8aS)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1H-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(tetrazol-1-yl)phenol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=C(O)C=1N1C=NN=N1 FEMNSKHMPWTPHC-CABCVRRESA-N 0.000 claims 1
UQVSEWRVTPZKIS-CABCVRRESA-N 4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-chloro-n-methylbenzamide Chemical compound C1=C(Cl)C(C(=O)NC)=CC=C1NC1=NC=C(F)C(N[C@H]2CC(C)(C)N3CCC[C@H]3C2)=N1 UQVSEWRVTPZKIS-CABCVRRESA-N 0.000 claims 1
PYLCVIJJKWPMAD-CABCVRRESA-N 4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C1 PYLCVIJJKWPMAD-CABCVRRESA-N 0.000 claims 1
BELKJKUODGXTKO-CABCVRRESA-N 4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-5-fluoro-2-(4-methyl-5-oxotetrazol-1-yl)benzonitrile Chemical compound O=C1N(C)N=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1C#N BELKJKUODGXTKO-CABCVRRESA-N 0.000 claims 1
XWQVQSXLXAXOPJ-QNGMFEMESA-N 4-[[[6-[5-chloro-2-[[4-[[(2r)-1-methoxypropan-2-yl]amino]cyclohexyl]amino]pyridin-4-yl]pyridin-2-yl]amino]methyl]oxane-4-carbonitrile Chemical compound C1CC(N[C@H](C)COC)CCC1NC1=CC(C=2N=C(NCC3(CCOCC3)C#N)C=CC=2)=C(Cl)C=N1 XWQVQSXLXAXOPJ-QNGMFEMESA-N 0.000 claims 1
GVCLNACSYKYUHP-UHFFFAOYSA-N 4-amino-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]pyrimidine-5-carbothioamide Chemical compound C1=NC(N)=C2C(C(=S)N)=CN(COCCO)C2=N1 GVCLNACSYKYUHP-UHFFFAOYSA-N 0.000 claims 1
GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 claims 1
WKEZTKWVWOCIOX-UHFFFAOYSA-N 4-n-(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)-2-n-(4,4-dimethyltetrazolo[5,1-c][1,4]benzoxazin-8-yl)-5-fluoropyrimidine-2,4-diamine Chemical compound O1C(C)(C)C2=NN=NN2C2=CC(NC=3N=C(C(=CN=3)F)NC3CC(N4CCCC4C3)(C)C)=CC=C21 WKEZTKWVWOCIOX-UHFFFAOYSA-N 0.000 claims 1
XLRKAEAQGYVMRK-HUUCEWRRSA-N 4-n-[(7r,8ar)-2,2-difluoro-5,5-dimethyl-1,3,6,7,8,8a-hexahydroindolizin-7-yl]-2-n-[4-cyclopropyl-2-fluoro-5-(tetrazol-1-yl)phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CC(F)(F)C[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C(=C1)F)=CC(N2N=NN=C2)=C1C1CC1 XLRKAEAQGYVMRK-HUUCEWRRSA-N 0.000 claims 1
LSHPMCNEHBDCDX-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-(2,2-dimethyl-1,3-benzodioxol-5-yl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1[C@@H]2CCCN2C(C)(C)C[C@@H]1NC1=NC(NC2=CC=C3OC(OC3=C2)(C)C)=NC=C1F LSHPMCNEHBDCDX-CVEARBPZSA-N 0.000 claims 1
QCBZCWVHYBHLTR-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-(3,5-dimethoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C1 QCBZCWVHYBHLTR-CVEARBPZSA-N 0.000 claims 1
WKEZTKWVWOCIOX-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-(4,4-dimethyltetrazolo[5,1-c][1,4]benzoxazin-8-yl)-5-fluoropyrimidine-2,4-diamine Chemical compound O1C(C)(C)C2=NN=NN2C2=CC(NC=3N=C(C(=CN=3)F)N[C@H]3CC(N4CCC[C@H]4C3)(C)C)=CC=C21 WKEZTKWVWOCIOX-CVEARBPZSA-N 0.000 claims 1
RHLVUQXMRHZMBF-KGLIPLIRSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[2,6-difluoro-3-methoxy-5-(5-methyltetrazol-1-yl)phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound FC=1C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C(OC)=CC=1N1N=NN=C1C RHLVUQXMRHZMBF-KGLIPLIRSA-N 0.000 claims 1
FRGCSWMHZSRXOH-SJORKVTESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[3-(5-cyclopropyltetrazol-1-yl)-4-fluorophenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=C(F)C=1N1N=NN=C1C1CC1 FRGCSWMHZSRXOH-SJORKVTESA-N 0.000 claims 1
VQNIXNJLJHWSHQ-MSOLQXFVSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[3-(difluoromethoxy)-4-piperidin-4-yloxyphenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1OC(F)F)=CC=C1OC1CCNCC1 VQNIXNJLJHWSHQ-MSOLQXFVSA-N 0.000 claims 1
WGNNMPNATYJUGM-PPULILFRSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[3-chloro-4-[(3s,4s)-3-fluoropiperidin-4-yl]oxyphenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1Cl)=CC=C1O[C@H]1CCNC[C@@H]1F WGNNMPNATYJUGM-PPULILFRSA-N 0.000 claims 1
QGDQXLUWKVXUOF-SJORKVTESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[4-chloro-3-(5-cyclopropyltetrazol-1-yl)phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=C(Cl)C=1N1N=NN=C1C1CC1 QGDQXLUWKVXUOF-SJORKVTESA-N 0.000 claims 1
WMEYYVIXYKYZRI-SJORKVTESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[5-(5-cyclopropyltetrazol-1-yl)-2-fluoro-4-(oxetan-3-yloxy)phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C(=C1)F)=CC(N2C(=NN=N2)C2CC2)=C1OC1COC1 WMEYYVIXYKYZRI-SJORKVTESA-N 0.000 claims 1
FSNAENBGXFHEJM-MSOLQXFVSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[5-(5-cyclopropyltetrazol-1-yl)-2-fluoro-4-propan-2-yloxyphenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound CC(C)OC1=CC(F)=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN=C1C1CC1 FSNAENBGXFHEJM-MSOLQXFVSA-N 0.000 claims 1
AFNLLFCNDPBODP-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[5-(5-cyclopropyltetrazol-1-yl)-2-fluorophenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C(=CC=1)F)=CC=1N1N=NN=C1C1CC1 AFNLLFCNDPBODP-CVEARBPZSA-N 0.000 claims 1
KYSPUNNHXOKRMC-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-chloro-2-n-(3,4,5-trimethoxyphenyl)pyrimidine-2,4-diamine Chemical class COC1=C(OC)C(OC)=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)=C1 KYSPUNNHXOKRMC-CVEARBPZSA-N 0.000 claims 1
SYMRBIIUFGGBDM-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-chloro-2-n-(3,5-dimethoxyphenyl)pyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)=C1 SYMRBIIUFGGBDM-CVEARBPZSA-N 0.000 claims 1
YEOKQWWKXRQYRB-SJORKVTESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-chloro-2-n-[4-methyl-3-(tetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound CC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(Cl)=CN=2)C=C1N1C=NN=N1 YEOKQWWKXRQYRB-SJORKVTESA-N 0.000 claims 1
METAQSSLDNXOEC-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-(3,4,5-trimethoxyphenyl)pyrimidine-2,4-diamine Chemical class COC1=C(OC)C(OC)=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C1 METAQSSLDNXOEC-CVEARBPZSA-N 0.000 claims 1
ISCXKFXOPIJVFT-CABCVRRESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[2-fluoro-3-methoxy-5-(5-methyltetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C=1C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C(OC)=CC=1N1N=NN=C1C ISCXKFXOPIJVFT-CABCVRRESA-N 0.000 claims 1
RWGKCGWOYIOHLQ-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[2-fluoro-5-(5-methyltetrazol-1-yl)-4-(oxetan-3-yloxy)phenyl]pyrimidine-2,4-diamine Chemical compound CC1=NN=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OC1COC1 RWGKCGWOYIOHLQ-CVEARBPZSA-N 0.000 claims 1
UVZFWCHTWOMTKW-CABCVRRESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[2-fluoro-5-[5-(methylamino)tetrazol-1-yl]-4-(oxetan-3-yloxy)phenyl]pyrimidine-2,4-diamine Chemical compound CNC1=NN=NN1C1=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=C1OC1COC1 UVZFWCHTWOMTKW-CABCVRRESA-N 0.000 claims 1
OYGSHDQOXXNZJL-CABCVRRESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[2-fluoro-5-methoxy-3-(5-methyltetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C=1C(OC)=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C(F)C=1N1N=NN=C1C OYGSHDQOXXNZJL-CABCVRRESA-N 0.000 claims 1
DRCXNJBQRNGYEM-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[3-(5-methylsulfanyltetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound CSC1=NN=NN1C1=CC=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C1 DRCXNJBQRNGYEM-CVEARBPZSA-N 0.000 claims 1
IPVMQWOBFJQJGA-JTISZYJISA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[3-(5-methylsulfinyltetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound CS(=O)C1=NN=NN1C1=CC=CC(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)=C1 IPVMQWOBFJQJGA-JTISZYJISA-N 0.000 claims 1
UALCKRLAAIOHDP-CVEARBPZSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[3-(5-methylsulfonyltetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1N1N=NN=C1S(C)(=O)=O UALCKRLAAIOHDP-CVEARBPZSA-N 0.000 claims 1
MBGNFLKVPXQVNZ-SJORKVTESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[3-[5-(oxetan-3-ylsulfanyl)tetrazol-1-yl]phenyl]pyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1N1N=NN=C1SC1COC1 MBGNFLKVPXQVNZ-SJORKVTESA-N 0.000 claims 1
ABSLCBMJYOGQPB-MSOLQXFVSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-(2-methoxyethoxy)-3-(tetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound COCCOC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1C=NN=N1 ABSLCBMJYOGQPB-MSOLQXFVSA-N 0.000 claims 1
ZJFUXKIDMCZPJL-MOPGFXCFSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-[(3-methyloxetan-3-yl)methoxy]-3-(tetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C=1C=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C(N2N=NN=C2)C=1OCC1(C)COC1 ZJFUXKIDMCZPJL-MOPGFXCFSA-N 0.000 claims 1
NIUSHXNLFDJTKR-AAYSFUBESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-[(3r,4r)-3-fluoro-1-(oxetan-3-yl)piperidin-4-yl]oxy-3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound C([C@H]([C@@H](C1)F)OC2=CC=C(C=C2C(F)(F)F)NC=2N=C(C(=CN=2)F)N[C@H]2CC(N3CCC[C@H]3C2)(C)C)CN1C1COC1 NIUSHXNLFDJTKR-AAYSFUBESA-N 0.000 claims 1
GENCTRCNSUVNAB-ZRAXVTTISA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C(F)(F)F)=CC=C1O[C@@H]1CCNC[C@H]1F GENCTRCNSUVNAB-ZRAXVTTISA-N 0.000 claims 1
GENCTRCNSUVNAB-PPULILFRSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-[(3s,4s)-3-fluoropiperidin-4-yl]oxy-3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C(F)(F)F)=CC=C1O[C@H]1CCNC[C@@H]1F GENCTRCNSUVNAB-PPULILFRSA-N 0.000 claims 1
BSPJCXJLHIGROG-UXHICEINSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-[1-(oxetan-3-yl)piperidin-4-yl]oxy-3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C(F)(F)F)=CC=C1OC(CC1)CCN1C1COC1 BSPJCXJLHIGROG-UXHICEINSA-N 0.000 claims 1
NGWWOKPVETWNQA-UXHICEINSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-[2-(2-methoxyethoxy)ethoxy]-3-(tetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound COCCOCCOC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1C=NN=N1 NGWWOKPVETWNQA-UXHICEINSA-N 0.000 claims 1
OBOIQQBQMJFUJD-SJORKVTESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-methoxy-3-[5-(oxetan-3-yloxy)tetrazol-1-yl]phenyl]pyrimidine-2,4-diamine Chemical compound COC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN=C1OC1COC1 OBOIQQBQMJFUJD-SJORKVTESA-N 0.000 claims 1
QQZNAVJIGQFEBH-SJORKVTESA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-methyl-3-(5-methylsulfonyltetrazol-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound CC1=CC=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C1N1N=NN=C1S(C)(=O)=O QQZNAVJIGQFEBH-SJORKVTESA-N 0.000 claims 1
OSABAYROLNNTLM-MSOLQXFVSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-[4-piperidin-4-yloxy-3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C(F)(F)F)=CC=C1OC1CCNCC1 OSABAYROLNNTLM-MSOLQXFVSA-N 0.000 claims 1
BQOCFPOOIYMRIQ-MSOLQXFVSA-N 4-n-[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-5-fluoro-2-n-spiro[oxane-4,4'-tetrazolo[5,1-c][1,4]benzoxazine]-8'-ylpyrimidine-2,4-diamine Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1N2N=NN=C22)=CC=C1OC12CCOCC1 BQOCFPOOIYMRIQ-MSOLQXFVSA-N 0.000 claims 1
XLRKAEAQGYVMRK-LSDHHAIUSA-N 4-n-[(7s,8ar)-2,2-difluoro-5,5-dimethyl-1,3,6,7,8,8a-hexahydroindolizin-7-yl]-2-n-[4-cyclopropyl-2-fluoro-5-(tetrazol-1-yl)phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@@H]1CC(N2CC(F)(F)C[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C(=C1)F)=CC(N2N=NN=C2)=C1C1CC1 XLRKAEAQGYVMRK-LSDHHAIUSA-N 0.000 claims 1
WKEZTKWVWOCIOX-JKSUJKDBSA-N 4-n-[(7s,8ar)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-(4,4-dimethyltetrazolo[5,1-c][1,4]benzoxazin-8-yl)-5-fluoropyrimidine-2,4-diamine Chemical compound O1C(C)(C)C2=NN=NN2C2=CC(NC=3N=C(C(=CN=3)F)N[C@@H]3CC(N4CCC[C@@H]4C3)(C)C)=CC=C21 WKEZTKWVWOCIOX-JKSUJKDBSA-N 0.000 claims 1
PQRBREMTEGTKOZ-WXDAQCLHSA-N 4-n-[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[3-(difluoromethoxy)-4-(2,6-dimethylmorpholin-4-yl)phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound C1C(C)OC(C)CN1C(C(=C1)OC(F)F)=CC=C1NC1=NC=C(F)C(N[C@@H]2C[C@H]3N(C(CC3)(C)C)CC2)=N1 PQRBREMTEGTKOZ-WXDAQCLHSA-N 0.000 claims 1
ZMEXZTXJCBLOBA-ROUUACIJSA-N 4-n-[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[3-(difluoromethoxy)-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1OC(F)F)=CC=C1N(C1)CC21COC2 ZMEXZTXJCBLOBA-ROUUACIJSA-N 0.000 claims 1
NFQZRUDMOBHDII-HOTGVXAUSA-N 4-n-[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[3-(difluoromethoxy)-4-(oxetan-3-yloxy)phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1OC(F)F)=CC=C1OC1COC1 NFQZRUDMOBHDII-HOTGVXAUSA-N 0.000 claims 1
NRECFMLBMQIJOJ-GJZGRUSLSA-N 4-n-[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[3-(difluoromethoxy)-4-methoxyphenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(OC(F)F)C(OC)=CC=C1NC1=NC=C(F)C(N[C@@H]2C[C@H]3N(C(CC3)(C)C)CC2)=N1 NRECFMLBMQIJOJ-GJZGRUSLSA-N 0.000 claims 1
IQPBHWOCHCAHDJ-ROUUACIJSA-N 4-n-[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[3-(difluoromethoxy)-4-morpholin-4-ylphenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1OC(F)F)=CC=C1N1CCOCC1 IQPBHWOCHCAHDJ-ROUUACIJSA-N 0.000 claims 1
USRIPHLDZDKOHR-HHLXFHKQSA-N 4-n-[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[3-chloro-4-(3-phenylmethoxycyclobutyl)oxyphenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1Cl)=CC=C1OC(C1)CC1OCC1=CC=CC=C1 USRIPHLDZDKOHR-HHLXFHKQSA-N 0.000 claims 1
GQKJYLNNJNAJFZ-ROUUACIJSA-N 4-n-[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-2-n-[4-cyclopropyl-2-fluoro-5-[5-(oxetan-3-yl)tetrazol-1-yl]phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C(=C1)F)=CC(N2C(=NN=N2)C2COC2)=C1C1CC1 GQKJYLNNJNAJFZ-ROUUACIJSA-N 0.000 claims 1
SZGIVHKLVAZLTN-UHFFFAOYSA-N 5-[[4-[(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]-5-fluoropyrimidin-2-yl]amino]-2-(oxan-4-yloxy)benzonitrile Chemical compound C1C2CCCN2C(C)(C)CC1NC(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1OC1CCOCC1 SZGIVHKLVAZLTN-UHFFFAOYSA-N 0.000 claims 1
HXCAJWLILGGKGO-UHFFFAOYSA-N 5-[[4-[(5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl)amino]-5-fluoropyrimidin-2-yl]amino]-2-(oxetan-3-yloxy)benzonitrile Chemical compound C1C2CCCN2C(C)(C)CC1NC(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1OC1COC1 HXCAJWLILGGKGO-UHFFFAOYSA-N 0.000 claims 1
XNUYXBDRLBGYMB-YADHBBJMSA-N 5-[[4-[[(7R,8aS)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1H-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(2-oxa-7-azaspiro[3.5]nonan-7-yl)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1N(CC1)CCC21COC2 XNUYXBDRLBGYMB-YADHBBJMSA-N 0.000 claims 1
CFZKOMYDWQHBLK-QINBWVTOSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]-(2,3-dihydroxypropyl)amino]-5-fluoropyrimidin-2-yl]amino]-2-(2,3-dihydroxypropoxy)benzonitrile Chemical compound OCC(O)CN([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCC(O)CO)C(C#N)=C1 CFZKOMYDWQHBLK-QINBWVTOSA-N 0.000 claims 1
QMQZDDGVFSWTCT-FWZRCDJUSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-2-(2-hydroxypropoxy)benzonitrile Chemical compound C1=C(C#N)C(OCC(O)C)=CC=C1NC1=NC=C(Cl)C(N[C@H]2CC(C)(C)N3CCC[C@H]3C2)=N1 QMQZDDGVFSWTCT-FWZRCDJUSA-N 0.000 claims 1
AWFGFVKKCHFGFU-SJORKVTESA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-2-cyclopropyl-4-fluorobenzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)Cl)=NC=1NC(C(=C1)F)=CC(C#N)=C1C1CC1 AWFGFVKKCHFGFU-SJORKVTESA-N 0.000 claims 1
PZBXTNIBWYOZPO-MOPGFXCFSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-2-cyclopropylbenzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)Cl)=NC=1NC(C=C1C#N)=CC=C1C1CC1 PZBXTNIBWYOZPO-MOPGFXCFSA-N 0.000 claims 1
MNJXEDXRUHXILB-MSOLQXFVSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-chloropyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound C1=C(C#N)C(C)=CC=C1NC1=NC=C(Cl)C(N[C@H]2CC(C)(C)N3CCC[C@H]3C2)=N1 MNJXEDXRUHXILB-MSOLQXFVSA-N 0.000 claims 1
UVOHNSFOXZUUQH-PDYHCXRVSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(1,4-dioxan-2-ylmethoxy)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1OCC1COCCO1 UVOHNSFOXZUUQH-PDYHCXRVSA-N 0.000 claims 1
SBLWIAGIZGVPQB-YTYFACEESA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(2,3-dihydroxypropoxy)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCC(O)CO)C(C#N)=C1 SBLWIAGIZGVPQB-YTYFACEESA-N 0.000 claims 1
ICJQVSAYHUGWMQ-MSOLQXFVSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(2-hydroxyethoxy)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCCO)C(C#N)=C1 ICJQVSAYHUGWMQ-MSOLQXFVSA-N 0.000 claims 1
NSRYLKCUATVCMT-FWZRCDJUSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(2-hydroxypropoxy)benzonitrile Chemical compound C1=C(C#N)C(OCC(O)C)=CC=C1NC1=NC=C(F)C(N[C@H]2CC(C)(C)N3CCC[C@H]3C2)=N1 NSRYLKCUATVCMT-FWZRCDJUSA-N 0.000 claims 1
VJNVZCKXESHMCK-MOPGFXCFSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(2-methoxyethoxy)benzonitrile Chemical compound C1=C(C#N)C(OCCOC)=CC=C1NC1=NC=C(F)C(N[C@H]2CC(C)(C)N3CCC[C@H]3C2)=N1 VJNVZCKXESHMCK-MOPGFXCFSA-N 0.000 claims 1
YNCLNQFBHKIYPL-MOPGFXCFSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(3-hydroxypropoxy)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCCCO)C(C#N)=C1 YNCLNQFBHKIYPL-MOPGFXCFSA-N 0.000 claims 1
BNPMCFWBDWYWEA-UXHICEINSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(4-hydroxypiperidin-1-yl)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1N1CCC(O)CC1 BNPMCFWBDWYWEA-UXHICEINSA-N 0.000 claims 1
QRXLQYSKFBGJAA-RTWAWAEBSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(4-methylpiperazin-1-yl)benzonitrile Chemical compound C1CN(C)CCN1C(C(=C1)C#N)=CC=C1NC1=NC=C(F)C(N[C@H]2CC(C)(C)N3CCC[C@H]3C2)=N1 QRXLQYSKFBGJAA-RTWAWAEBSA-N 0.000 claims 1
JQTRJMHNEYMEPT-RTWAWAEBSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(4-methylsulfonylpiperazin-1-yl)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1N1CCN(S(C)(=O)=O)CC1 JQTRJMHNEYMEPT-RTWAWAEBSA-N 0.000 claims 1
IFRJFBXWXJEMGW-PKTZIBPZSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(4-propan-2-ylpiperazin-1-yl)benzonitrile Chemical compound C1CN(C(C)C)CCN1C(C(=C1)C#N)=CC=C1NC1=NC=C(F)C(N[C@H]2CC(C)(C)N3CCC[C@H]3C2)=N1 IFRJFBXWXJEMGW-PKTZIBPZSA-N 0.000 claims 1
BVVVKFNLNDZQMA-YADHBBJMSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(oxan-4-ylmethoxy)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1OCC1CCOCC1 BVVVKFNLNDZQMA-YADHBBJMSA-N 0.000 claims 1
RBFWJYVUZWEPKC-LFPSWIHMSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(oxetan-2-ylmethoxy)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1OCC1CCO1 RBFWJYVUZWEPKC-LFPSWIHMSA-N 0.000 claims 1
BBZYTNGAOCELNO-UXHICEINSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(oxetan-3-ylmethoxy)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1OCC1COC1 BBZYTNGAOCELNO-UXHICEINSA-N 0.000 claims 1
HXCAJWLILGGKGO-MSOLQXFVSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(oxetan-3-yloxy)benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1OC1COC1 HXCAJWLILGGKGO-MSOLQXFVSA-N 0.000 claims 1
HFQAAMHPIHRWSL-UXHICEINSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-[(3-methyloxetan-3-yl)methoxy]benzonitrile Chemical compound C=1C=C(NC=2N=C(N[C@H]3CC(C)(C)N4CCC[C@H]4C3)C(F)=CN=2)C=C(C#N)C=1OCC1(C)COC1 HFQAAMHPIHRWSL-UXHICEINSA-N 0.000 claims 1
YAERTUBLVQASEC-RTWAWAEBSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-[2-(2-methoxyethoxy)ethoxy]benzonitrile Chemical compound C1=C(C#N)C(OCCOCCOC)=CC=C1NC1=NC=C(F)C(N[C@H]2CC(C)(C)N3CCC[C@H]3C2)=N1 YAERTUBLVQASEC-RTWAWAEBSA-N 0.000 claims 1
NNHWZWYQMZHVDN-SJORKVTESA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-[3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propoxy]benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(OCC(O)(C(F)(F)F)C(F)(F)F)C(C#N)=C1 NNHWZWYQMZHVDN-SJORKVTESA-N 0.000 claims 1
VDRXYXJEMPJMRX-YADHBBJMSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-[4-(oxetan-3-yl)piperazin-1-yl]benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1N(CC1)CCN1C1COC1 VDRXYXJEMPJMRX-YADHBBJMSA-N 0.000 claims 1
AVPWIUXKJZCBQZ-UXHICEINSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-[[3-(hydroxymethyl)oxetan-3-yl]methoxy]benzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1OCC1(CO)COC1 AVPWIUXKJZCBQZ-UXHICEINSA-N 0.000 claims 1
GREQTIDRJDGRIH-CVEARBPZSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-bromobenzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(Br)C(C#N)=C1 GREQTIDRJDGRIH-CVEARBPZSA-N 0.000 claims 1
ZAVOAQGMUOUQMD-CVEARBPZSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-hydroxybenzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC1=CC=C(O)C(C#N)=C1 ZAVOAQGMUOUQMD-CVEARBPZSA-N 0.000 claims 1
CKFZLXIEORWZMB-UXHICEINSA-N 5-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-morpholin-4-ylbenzonitrile Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1N1CCOCC1 CKFZLXIEORWZMB-UXHICEINSA-N 0.000 claims 1
VLEHKZNXPSDDFK-VCAKUFKGSA-N 5-[[4-[[(7s,8as)-3,3-dimethyl-2,5,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(3-hydroxycyclobutyl)oxybenzonitrile Chemical compound N([C@@H]1C[C@@H]2CCC(N2CC1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1C#N)=CC=C1OC1CC(O)C1 VLEHKZNXPSDDFK-VCAKUFKGSA-N 0.000 claims 1
ZBXNFTFKKOSPLD-UHFFFAOYSA-N 5-methylsulfanyl-2h-tetrazole Chemical compound CSC1=NN=NN1 ZBXNFTFKKOSPLD-UHFFFAOYSA-N 0.000 claims 1
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NJIAKNWTIVDSDA-FQEVSTJZSA-N 7-[4-(1-methylsulfonylpiperidin-4-yl)phenyl]-n-[[(2s)-morpholin-2-yl]methyl]pyrido[3,4-b]pyrazin-5-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=CC=C(C=2N=C(NC[C@H]3OCCNC3)C3=NC=CN=C3C=2)C=C1 NJIAKNWTIVDSDA-FQEVSTJZSA-N 0.000 claims 1
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SCJNYBYSTCRPAO-LXBQGUBHSA-N CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 Chemical compound CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 SCJNYBYSTCRPAO-LXBQGUBHSA-N 0.000 claims 1
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LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 claims 1
AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 claims 1
POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 claims 1
230000006044 T cell activation Effects 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
DRBWRJPFNOBNIO-KOLCDFICSA-N [(2r)-1-[(2r)-2-(pyridine-4-carbonylamino)propanoyl]pyrrolidin-2-yl]boronic acid Chemical compound N([C@H](C)C(=O)N1[C@@H](CCC1)B(O)O)C(=O)C1=CC=NC=C1 DRBWRJPFNOBNIO-KOLCDFICSA-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
IRFNXEAXZDNYGA-MOPGFXCFSA-N [3-[[4-[[4-[[(7r,8as)-5,5-dimethyl-2,3,6,7,8,8a-hexahydro-1h-indolizin-7-yl]amino]-5-fluoropyrimidin-2-yl]amino]-2-(tetrazol-1-yl)phenoxy]methyl]oxetan-3-yl]methanol Chemical compound N([C@H]1CC(N2CCC[C@H]2C1)(C)C)C(C(=CN=1)F)=NC=1NC(C=C1N2N=NN=C2)=CC=C1OCC1(CO)COC1 IRFNXEAXZDNYGA-MOPGFXCFSA-N 0.000 claims 1
QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000000304 alkynyl group Chemical group 0.000 claims 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
OTKPPUXRIADSGD-PPRNARJGSA-N avoparcina Chemical compound O([C@@H]1C2=CC=C(C(=C2)Cl)OC=2C=C3C=C(C=2O[C@H]2C([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@H](N)C2)OC2=CC=C(C=C2)[C@@H](O)[C@H](C(N[C@H](C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)C=1C=CC(O)=CC=1)=O)NC(=O)[C@H](NC)C=1C=CC(O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)=CC=1)[C@H]1C[C@@H](N)[C@@H](O)[C@H](C)O1 OTKPPUXRIADSGD-PPRNARJGSA-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
229940126208 compound 22 Drugs 0.000 claims 1
229940125833 compound 23 Drugs 0.000 claims 1
229940125961 compound 24 Drugs 0.000 claims 1
229940125851 compound 27 Drugs 0.000 claims 1
229940125877 compound 31 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
125000000753 cycloalkyl group Chemical group 0.000 claims 1
BFXLJWUGRPGMFU-UHFFFAOYSA-N dipropoxyphosphinothioyl n,n-diethylcarbamodithioate;sulfane Chemical compound S.CCCOP(=S)(OCCC)SC(=S)N(CC)CC BFXLJWUGRPGMFU-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
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230000002401 inhibitory effect Effects 0.000 claims 1
230000005764 inhibitory process Effects 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
230000001404 mediated effect Effects 0.000 claims 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
IHCHOVVAJBADAH-UHFFFAOYSA-N n-[2-hydroxy-4-(1h-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1C2=CC(OC)=CC=C2OCC1C(=O)NC(C(=C1)O)=CC=C1C=1C=NNC=1 IHCHOVVAJBADAH-UHFFFAOYSA-N 0.000 claims 1
LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-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
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
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 claims 1
150000003839 salts Chemical class 0.000 claims 1
KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims 1
125000005017 substituted alkenyl group Chemical group 0.000 claims 1
125000004426 substituted alkynyl group Chemical group 0.000 claims 1
125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
230000002459 sustained effect Effects 0.000 claims 1

JP2015504725A 2012-04-04 2013-04-04 プロテインキナーゼｃ阻害剤およびその使用 Expired - Fee Related JP6113828B2 (ja)