JPWO2019182924A5 - - Google Patents
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- Publication number
- JPWO2019182924A5 JPWO2019182924A5 JP2020550114A JP2020550114A JPWO2019182924A5 JP WO2019182924 A5 JPWO2019182924 A5 JP WO2019182924A5 JP 2020550114 A JP2020550114 A JP 2020550114A JP 2020550114 A JP2020550114 A JP 2020550114A JP WO2019182924 A5 JPWO2019182924 A5 JP WO2019182924A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrrolo
- amino
- azaspiro
- pyrimidin
- 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
- -1 dehydrogen Chemical class 0.000 claims 112
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 235000019000 fluorine Nutrition 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- YCQNXZAQYYNQTH-UHFFFAOYSA-N 2-methyl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=NC=C2C=CNC2=N1 YCQNXZAQYYNQTH-UHFFFAOYSA-N 0.000 claims 3
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 3
- 125000005038 alkynylalkyl group Chemical group 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- KDOUHIDUYPIERE-UHFFFAOYSA-N (1-methylpyrazol-3-yl)-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]methanone Chemical compound CN(C1CC2(CN(C2)C(=O)C2=NN(C=C2)C)C1)C=1C2=C(N=CN=1)NC=C2 KDOUHIDUYPIERE-UHFFFAOYSA-N 0.000 claims 1
- PWXMZODMDSDALW-UHFFFAOYSA-N (2-chloro-4-ethynylphenyl)-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]methanone Chemical compound ClC1=C(C=CC(=C1)C#C)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C PWXMZODMDSDALW-UHFFFAOYSA-N 0.000 claims 1
- VTSWOGVBFUOALQ-UHFFFAOYSA-N (3-chloro-4-ethynylphenyl)-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]methanone Chemical compound ClC=1C=C(C=CC=1C#C)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C VTSWOGVBFUOALQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- NWQMLXUIWUYHSD-UHFFFAOYSA-N 1-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]-3-methylsulfonylpropan-1-one Chemical compound CN(C1CC2(C1)CN(C2)C(=O)CCS(C)(=O)=O)C1=NC=NC2=C1C=CN2 NWQMLXUIWUYHSD-UHFFFAOYSA-N 0.000 claims 1
- BYISEBGOLCFZQT-UHFFFAOYSA-N 1-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]cyclopropane-1-carbonitrile Chemical compound CN(C1CC2(CN(C2)C(=O)C2(CC2)C#N)C1)C=1C2=C(N=CN=1)NC=C2 BYISEBGOLCFZQT-UHFFFAOYSA-N 0.000 claims 1
- PZIDCZRIHGNHPD-UHFFFAOYSA-N 1-methylbenzimidazole-5-carbaldehyde Chemical compound O=CC1=CC=C2N(C)C=NC2=C1 PZIDCZRIHGNHPD-UHFFFAOYSA-N 0.000 claims 1
- ZHIJLYUJVZKCDE-UHFFFAOYSA-N 2,2,2-trifluoroethyl 9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxylate Chemical compound CN(C1CCC2(CCN(CC2)C(=O)OCC(F)(F)F)CC1)C=1C2=C(N=CN=1)NC=C2 ZHIJLYUJVZKCDE-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- VWKRQZISFUNTGH-UHFFFAOYSA-N 2,3-dichloro-4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound ClC1=C(C#N)C=CC(=C1Cl)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C VWKRQZISFUNTGH-UHFFFAOYSA-N 0.000 claims 1
- JPRZCHJAVZPIMR-UHFFFAOYSA-N 2,3-difluoro-4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1F)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C JPRZCHJAVZPIMR-UHFFFAOYSA-N 0.000 claims 1
- IPSDQRYFGZNDAI-UHFFFAOYSA-N 2,3-difluoro-5-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound FC1=C(C#N)C=C(C=C1F)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C IPSDQRYFGZNDAI-UHFFFAOYSA-N 0.000 claims 1
- LZTVLJMNGXVCJP-UHFFFAOYSA-N 2,5-difluoro-4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound FC1=C(C#N)C=C(C(=C1)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C)F LZTVLJMNGXVCJP-UHFFFAOYSA-N 0.000 claims 1
- NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 claims 1
- WJZIPMQUKSTHLV-UHFFFAOYSA-N 2-ethyldecanoic acid Chemical compound CCCCCCCCC(CC)C(O)=O WJZIPMQUKSTHLV-UHFFFAOYSA-N 0.000 claims 1
- ZKVWEDANSGSWPD-UHFFFAOYSA-N 2-fluoro-5-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound FC1=C(C#N)C=C(C=C1)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C ZKVWEDANSGSWPD-UHFFFAOYSA-N 0.000 claims 1
- OXQAFIPYGXVTEI-UHFFFAOYSA-N 2-methyl-4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound CC1=C(C#N)C=CC(=C1)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C OXQAFIPYGXVTEI-UHFFFAOYSA-N 0.000 claims 1
- TVBKULHUOUDGIL-UHFFFAOYSA-N 3,5-difluoro-4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound FC=1C=C(C#N)C=C(C=1C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C)F TVBKULHUOUDGIL-UHFFFAOYSA-N 0.000 claims 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 claims 1
- UYAIPRMOKFAMMH-UHFFFAOYSA-N 3-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]-3-oxopropanenitrile Chemical compound CN(C1CC2(CN(C2)C(CC#N)=O)C1)C=1C2=C(N=CN=1)NC=C2 UYAIPRMOKFAMMH-UHFFFAOYSA-N 0.000 claims 1
- YPBRWUQWYVFATN-UHFFFAOYSA-N 3-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound CN(C1CC2(CN(C2)C(=O)C=2C=C(C#N)C=CC=2)C1)C=1C2=C(N=CN=1)NC=C2 YPBRWUQWYVFATN-UHFFFAOYSA-N 0.000 claims 1
- NDUWLZCWAXNXLO-UHFFFAOYSA-N 3-[9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carbonyl]benzonitrile Chemical compound CN(C1CCC2(CCN(CC2)C(=O)C=2C=C(C#N)C=CC=2)CC1)C=1C2=C(N=CN=1)NC=C2 NDUWLZCWAXNXLO-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- JFZIQIRABHLLKM-UHFFFAOYSA-N 3-fluoro-4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound FC=1C=C(C#N)C=CC=1C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C JFZIQIRABHLLKM-UHFFFAOYSA-N 0.000 claims 1
- GAUWBTAIXVUZLY-UHFFFAOYSA-N 3-fluoro-4-[9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carbonyl]benzonitrile Chemical compound FC=1C=C(C#N)C=CC=1C(=O)N1CCC2(CC1)CCC(CC2)N(C=1C2=C(N=CN=1)NC=C2)C GAUWBTAIXVUZLY-UHFFFAOYSA-N 0.000 claims 1
- RSVWDCQCHSMMND-UHFFFAOYSA-N 3-fluoro-5-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound FC=1C=C(C#N)C=C(C=1)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C RSVWDCQCHSMMND-UHFFFAOYSA-N 0.000 claims 1
- BSQKBHXYEKVKMN-UHFFFAOYSA-N 3-methylthiophene-2-carbaldehyde Chemical compound CC=1C=CSC=1C=O BSQKBHXYEKVKMN-UHFFFAOYSA-N 0.000 claims 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 1
- GEDPIBRYKFZQSE-UHFFFAOYSA-N 4,4,4-trifluoro-1-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]butan-1-one Chemical compound FC(CCC(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C)(F)F GEDPIBRYKFZQSE-UHFFFAOYSA-N 0.000 claims 1
- BLZMXOQDHLRLNE-UHFFFAOYSA-N 4-[2-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]-2-oxoethyl]benzonitrile Chemical compound CN(C1CC2(CN(C2)C(CC2=CC=C(C#N)C=C2)=O)C1)C=1C2=C(N=CN=1)NC=C2 BLZMXOQDHLRLNE-UHFFFAOYSA-N 0.000 claims 1
- DICQZGXPVOZSBT-UHFFFAOYSA-N 4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]-4-oxobutanenitrile Chemical compound CN(C1CC2(CN(C2)C(CCC#N)=O)C1)C=1C2=C(N=CN=1)NC=C2 DICQZGXPVOZSBT-UHFFFAOYSA-N 0.000 claims 1
- JMMCTEYNTCZHTP-UHFFFAOYSA-N 4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzenesulfonamide Chemical compound CN(C1CC2(CN(C2)C(=O)C2=CC=C(C=C2)S(=O)(=O)N)C1)C=1C2=C(N=CN=1)NC=C2 JMMCTEYNTCZHTP-UHFFFAOYSA-N 0.000 claims 1
- OKEQLCCGZRYWNG-UHFFFAOYSA-N 4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]cyclohexan-1-one Chemical compound CN(C1CC2(CN(C2)C(=O)C2CCC(CC2)=O)C1)C=1C2=C(N=CN=1)NC=C2 OKEQLCCGZRYWNG-UHFFFAOYSA-N 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- GORVKYKEYCQOMR-UHFFFAOYSA-N 5-fluoro-2-methyl-4-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carbonyl]benzonitrile Chemical compound FC=1C(=CC(=C(C#N)C=1)C)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C GORVKYKEYCQOMR-UHFFFAOYSA-N 0.000 claims 1
- JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
- RCSIOFWAUFWXMM-UHFFFAOYSA-N N-(2-ethylsulfonyl-2-azaspiro[3.3]heptan-6-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C(C)S(=O)(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C RCSIOFWAUFWXMM-UHFFFAOYSA-N 0.000 claims 1
- WXXYIUCRGXQTIQ-UHFFFAOYSA-N N-(3-methoxyphenyl)-9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxamide Chemical compound COC=1C=C(C=CC=1)NC(=O)N1CCC2(CC1)CCC(CC2)N(C=1C2=C(N=CN=1)NC=C2)C WXXYIUCRGXQTIQ-UHFFFAOYSA-N 0.000 claims 1
- DCVLNAFSEGHRSD-UHFFFAOYSA-N N-(4-cyanophenyl)-9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxamide Chemical compound C(#N)C1=CC=C(C=C1)NC(=O)N1CCC2(CC1)CCC(CC2)N(C=1C2=C(N=CN=1)NC=C2)C DCVLNAFSEGHRSD-UHFFFAOYSA-N 0.000 claims 1
- IDHQIVCHWLXHEJ-UHFFFAOYSA-N N-(5-fluoro-1,3-thiazol-2-yl)-9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxamide Chemical compound FC1=CN=C(S1)NC(=O)N1CCC2(CC1)CCC(CC2)N(C=1C2=C(N=CN=1)NC=C2)C IDHQIVCHWLXHEJ-UHFFFAOYSA-N 0.000 claims 1
- MWFZEGBBWGJGPE-UHFFFAOYSA-N N-(5-methoxypyrazin-2-yl)-9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxamide Chemical compound COC=1N=CC(=NC=1)NC(=O)N1CCC2(CC1)CCC(CC2)N(C=1C2=C(N=CN=1)NC=C2)C MWFZEGBBWGJGPE-UHFFFAOYSA-N 0.000 claims 1
- HALYKECWLOUIFT-UHFFFAOYSA-N N-(5-methoxypyridin-2-yl)-9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxamide Chemical compound COC=1C=CC(=NC=1)NC(=O)N1CCC2(CC1)CCC(CC2)N(C=1C2=C(N=CN=1)NC=C2)C HALYKECWLOUIFT-UHFFFAOYSA-N 0.000 claims 1
- PSCQQIWXFNPLPN-UHFFFAOYSA-N N-(5-methylpyrazin-2-yl)-9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxamide Chemical compound CN(C1CCC2(CCN(CC2)C(=O)NC2=NC=C(N=C2)C)CC1)C=1C2=C(N=CN=1)NC=C2 PSCQQIWXFNPLPN-UHFFFAOYSA-N 0.000 claims 1
- LBGAWZULJFMLJK-UHFFFAOYSA-N N-(6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-N-methyl-3-propylsulfonyl-3-azaspiro[5.5]undecan-9-amine Chemical compound N1=CN=C(C2=C1NCC2)N(C1CCC2(CCN(CC2)S(=O)(=O)CCC)CC1)C LBGAWZULJFMLJK-UHFFFAOYSA-N 0.000 claims 1
- SBJVNDZLFROZPP-UHFFFAOYSA-N N-(6-methoxypyridin-2-yl)-9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxamide Chemical compound COC1=CC=CC(=N1)NC(=O)N1CCC2(CC1)CCC(CC2)N(C=1C2=C(N=CN=1)NC=C2)C SBJVNDZLFROZPP-UHFFFAOYSA-N 0.000 claims 1
- FGFBDNHPJMDHEB-UHFFFAOYSA-N N-methyl-9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxamide Chemical compound CNC(=O)N1CCC2(CC1)CCC(CC2)N(C=1C2=C(N=CN=1)NC=C2)C FGFBDNHPJMDHEB-UHFFFAOYSA-N 0.000 claims 1
- JXRUFSJHYPIPGT-UHFFFAOYSA-N [4-(1-methylpyrazol-3-yl)phenyl]-[6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]methanone Chemical compound CN1N=C(C=C1)C1=CC=C(C=C1)C(=O)N1CC2(C1)CC(C2)N(C=1C2=C(N=CN=1)NC=C2)C JXRUFSJHYPIPGT-UHFFFAOYSA-N 0.000 claims 1
- XZLVYKRCLBOZJX-UHFFFAOYSA-N [6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptan-2-yl]-pyrazin-2-ylmethanone Chemical compound CN(C1CC2(CN(C2)C(=O)C2=NC=CN=C2)C1)C=1C2=C(N=CN=1)NC=C2 XZLVYKRCLBOZJX-UHFFFAOYSA-N 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 1
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 1
- 229940046731 calcineurin inhibitors Drugs 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims 1
- FJMRXECXSJRKNH-UHFFFAOYSA-N ethyl 6-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-2-azaspiro[3.3]heptane-2-carboxylate Chemical compound CN(C1CC2(CN(C2)C(=O)OCC)C1)C=1C2=C(N=CN=1)NC=C2 FJMRXECXSJRKNH-UHFFFAOYSA-N 0.000 claims 1
- IEZLVROUSQUEJE-UHFFFAOYSA-N ethyl 9-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxylate Chemical compound C(C)OC(=O)N1CCC2(CC1)CCC(CC2)N(C=1C2=C(N=CN=1)NC=C2)C IEZLVROUSQUEJE-UHFFFAOYSA-N 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 1
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 1
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims 1
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 claims 1
- 229960000681 leflunomide Drugs 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 229940124530 sulfonamide Drugs 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862646167P | 2018-03-21 | 2018-03-21 | |
| US62/646,167 | 2018-03-21 | ||
| PCT/US2019/022657 WO2019182924A1 (en) | 2018-03-21 | 2019-03-18 | Jak inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021518379A JP2021518379A (ja) | 2021-08-02 |
| JPWO2019182924A5 true JPWO2019182924A5 (ru) | 2022-03-30 |
| JP7462951B2 JP7462951B2 (ja) | 2024-04-08 |
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| JP2020550114A Active JP7462951B2 (ja) | 2018-03-21 | 2019-03-18 | Ｊａｋ阻害剤 |
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| US (1) | US11365188B2 (ru) |
| EP (1) | EP3768272A4 (ru) |
| JP (1) | JP7462951B2 (ru) |
| CN (1) | CN111936144B (ru) |
| AU (1) | AU2019237991A1 (ru) |
| CA (1) | CA3093706A1 (ru) |
| WO (1) | WO2019182924A1 (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20210141778A (ko) | 2016-06-07 | 2021-11-23 | 자코바이오 파마슈티칼스 컴퍼니 리미티드 | Shp2 억제제로서 유용한 신규한 헤테로환형 유도체 |
| KR20220113545A (ko) | 2017-03-23 | 2022-08-12 | 자코바이오 파마슈티칼스 컴퍼니 리미티드 | Shp2 억제제로서 유용한 신규한 헤테로환형 유도체 |
| US10744136B2 (en) * | 2018-11-05 | 2020-08-18 | Avista Pharma Solutions, Inc. | Sulfonamide derivatives as JAK inhibitors |
| WO2020154350A1 (en) | 2019-01-23 | 2020-07-30 | Theravance Biopharma R&D Ip, Llc | Imidazo[1,5-a]pyridine, 1,2,4-triazolo[4,3-a]pyridine and imidazo[1,5-a]pyrazine as jak inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US9527851B2 (en) | 2011-12-21 | 2016-12-27 | Jiangsu Hengrui Medicine Co., Ltd. | Pyrrole six-membered heteroaryl ring derivative, preparation method thereof, and medicinal uses thereof |
| JP6192839B2 (ja) * | 2013-12-05 | 2017-09-06 | ファイザー・インク | ピロロ［２，３−ｄ］ピリミジニル、ピロロ［２，３−ｂ］ピラジニル、およびピロロ［２，３−ｄ］ピリジニルアクリルアミド |
| WO2015131080A1 (en) | 2014-02-28 | 2015-09-03 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| WO2016024185A1 (en) * | 2014-08-12 | 2016-02-18 | Pfizer Inc. | Pyrrolo[2,3-d]pyrimidine derivatives useful for inhibiting janus kinase |
| CN108349977B (zh) * | 2015-01-20 | 2021-05-25 | 无锡福祈制药有限公司 | Jak抑制剂 |
| WO2018169700A1 (en) * | 2017-03-14 | 2018-09-20 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
-
2019
- 2019-03-18 US US16/979,455 patent/US11365188B2/en active Active
- 2019-03-18 CN CN201980020463.5A patent/CN111936144B/zh active Active
- 2019-03-18 JP JP2020550114A patent/JP7462951B2/ja active Active
- 2019-03-18 EP EP19770607.0A patent/EP3768272A4/en active Pending
- 2019-03-18 CA CA3093706A patent/CA3093706A1/en active Pending
- 2019-03-18 WO PCT/US2019/022657 patent/WO2019182924A1/en unknown
- 2019-03-18 AU AU2019237991A patent/AU2019237991A1/en active Pending
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