JP2020505454A5 - - Google Patents
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- Publication number
- JP2020505454A5 JP2020505454A5 JP2019559413A JP2019559413A JP2020505454A5 JP 2020505454 A5 JP2020505454 A5 JP 2020505454A5 JP 2019559413 A JP2019559413 A JP 2019559413A JP 2019559413 A JP2019559413 A JP 2019559413A JP 2020505454 A5 JP2020505454 A5 JP 2020505454A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- methyl
- pyrimidin
- pyrido
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 = O Chemical group 0.000 claims 174
- 125000000217 alkyl group Chemical group 0.000 claims 126
- 125000000753 cycloalkyl group Chemical group 0.000 claims 60
- 125000005843 halogen group Chemical group 0.000 claims 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 50
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 48
- 125000003118 aryl group Chemical group 0.000 claims 38
- 150000003839 salts Chemical class 0.000 claims 36
- 239000012453 solvate Substances 0.000 claims 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 32
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000001188 haloalkyl group Chemical group 0.000 claims 24
- QZILSYOEHMXZBE-UHFFFAOYSA-N pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=N1 QZILSYOEHMXZBE-UHFFFAOYSA-N 0.000 claims 20
- 229910052799 carbon Inorganic materials 0.000 claims 19
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 17
- 125000004429 atom Chemical group 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 208000015181 infectious disease Diseases 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 claims 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- FOBJIQQKXWVAFW-IKJXHCRLSA-N (3R)-3-methyl-4-[4-[2-[2-(trifluoromethyl)phenyl]azetidin-1-yl]pyrido[2,3-d]pyrimidin-2-yl]morpholine Chemical compound C[C@H]1N(CCOC1)C=1N=C(C2=C(N=1)N=CC=C2)N1C(CC1)C1=C(C=CC=C1)C(F)(F)F FOBJIQQKXWVAFW-IKJXHCRLSA-N 0.000 claims 2
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 2
- 241000238631 Hexapoda Species 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- LYXZTYXDCZQKSS-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine-2,4-diamine Chemical compound C1=CC=NC2=NC(N)=NC(N)=C21 LYXZTYXDCZQKSS-UHFFFAOYSA-N 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims 2
- PSYGVOQINLFTHK-UHFFFAOYSA-N pyrimido[4,5-d]pyrimidin-4-amine Chemical compound C1=NC=C2C(N)=NC=NC2=N1 PSYGVOQINLFTHK-UHFFFAOYSA-N 0.000 claims 2
- QIZMFTNGJPBSBT-UHFFFAOYSA-N thieno[3,2-d]pyrimidin-4-amine Chemical compound NC1=NC=NC2=C1SC=C2 QIZMFTNGJPBSBT-UHFFFAOYSA-N 0.000 claims 2
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 claims 2
- MIBBXEPYCSETKJ-JBZHPUCOSA-N (3R)-3-methyl-4-[4-[2-[2-(trifluoromethyl)pyridin-3-yl]azetidin-1-yl]pyrido[2,3-d]pyrimidin-2-yl]morpholine Chemical compound C[C@H]1N(CCOC1)C=1N=C(C2=C(N=1)N=CC=C2)N1C(CC1)C=1C(=NC=CC=1)C(F)(F)F MIBBXEPYCSETKJ-JBZHPUCOSA-N 0.000 claims 1
- MIBBXEPYCSETKJ-KNVGNIICSA-N (3S)-3-methyl-4-[4-[2-[2-(trifluoromethyl)pyridin-3-yl]azetidin-1-yl]pyrido[2,3-d]pyrimidin-2-yl]morpholine Chemical compound C[C@@H]1N(CCOC1)C=1N=C(C2=C(N=1)N=CC=C2)N1C(CC1)C=1C(=NC=CC=1)C(F)(F)F MIBBXEPYCSETKJ-KNVGNIICSA-N 0.000 claims 1
- LTUUBEKEKYEENZ-UHFFFAOYSA-N 1-[3-[[2-[benzyl(methyl)amino]thieno[3,2-d]pyrimidin-4-yl]amino]propyl]pyrrolidin-2-one Chemical compound C(C1=CC=CC=C1)N(C=1N=C(C2=C(N=1)C=CS2)NCCCN1C(CCC1)=O)C LTUUBEKEKYEENZ-UHFFFAOYSA-N 0.000 claims 1
- HQIHDLVHGCISAU-UHFFFAOYSA-N 1-[4-[[2-(trifluoromethyl)pyridin-3-yl]methylamino]pyrido[2,3-d]pyrimidin-2-yl]piperidine-3-carbonitrile Chemical compound FC(F)(F)c1ncccc1CNc1nc(nc2ncccc12)N1CCCC(C1)C#N HQIHDLVHGCISAU-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- DGIGXQPVYLINMR-UHFFFAOYSA-N 2-(2,2-difluoro-7-azaspiro[3.5]nonan-7-yl)-N-[[2-(trifluoromethyl)phenyl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC1(CC2(C1)CCN(CC2)C=1N=C(C2=C(N=1)N=CC=C2)NCC1=C(C=CC=C1)C(F)(F)F)F DGIGXQPVYLINMR-UHFFFAOYSA-N 0.000 claims 1
- KBTGTOATUNIFBJ-UHFFFAOYSA-N 2-(2,2-difluoro-7-azaspiro[3.5]nonan-7-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC1(CC2(C1)CCN(CC2)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)F KBTGTOATUNIFBJ-UHFFFAOYSA-N 0.000 claims 1
- HIYRDTACFTZPPL-UHFFFAOYSA-N 2-(2,2-difluoro-7-azaspiro[3.5]nonan-7-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine methanesulfonic acid Chemical compound CS(O)(=O)=O.FC(F)(F)c1ncccc1CNc1nc(nc2ncccc12)N1CCC2(CC(F)(F)C2)CC1 HIYRDTACFTZPPL-UHFFFAOYSA-N 0.000 claims 1
- HPQVEIBUEHTUHQ-UHFFFAOYSA-N 2-(2,2-dimethylmorpholin-4-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound CC1(OCCN(C1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)C HPQVEIBUEHTUHQ-UHFFFAOYSA-N 0.000 claims 1
- FOZCVWCXFJGOSK-UHFFFAOYSA-N 2-(2-cyclopropylmorpholin-4-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1(CC1)C1OCCN(C1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F FOZCVWCXFJGOSK-UHFFFAOYSA-N 0.000 claims 1
- NPHCDYCEBRGRAJ-UHFFFAOYSA-N 2-(2-oxa-5-azabicyclo[4.1.0]heptan-5-yl)-N-[[2-(trifluoromethyl)phenyl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C12OCCN(C2C1)C=1N=C(C2=C(N=1)N=CC=C2)NCC1=C(C=CC=C1)C(F)(F)F NPHCDYCEBRGRAJ-UHFFFAOYSA-N 0.000 claims 1
- ZWYMUQNEZWMNIY-UHFFFAOYSA-N 2-(3,3-difluoropyrrolidin-1-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC1(CN(CC1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)F ZWYMUQNEZWMNIY-UHFFFAOYSA-N 0.000 claims 1
- BJGZUWGCEWQJOH-UHFFFAOYSA-N 2-(3,3-dimethylmorpholin-4-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound CC1(C)COCCN1C1=NC(NCC2=CC=CN=C2C(F)(F)F)=C2C=CC=NC2=N1 BJGZUWGCEWQJOH-UHFFFAOYSA-N 0.000 claims 1
- VSIOREROFNYHHU-UHFFFAOYSA-N 2-(3-cyclopropylmorpholin-4-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1(CC1)C1COCCN1C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F VSIOREROFNYHHU-UHFFFAOYSA-N 0.000 claims 1
- VJOSCYDZFIBYAT-UHFFFAOYSA-N 2-(3-methylmorpholin-4-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pteridin-4-amine Chemical compound CC1COCCN1C1=NC2=NC=CN=C2C(=N1)NCC=1C(=NC=CC=1)C(F)(F)F VJOSCYDZFIBYAT-UHFFFAOYSA-N 0.000 claims 1
- IZFVCNUAPFSNCO-UHFFFAOYSA-N 2-(3-methylmorpholin-4-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound CC1COCCN1C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F IZFVCNUAPFSNCO-UHFFFAOYSA-N 0.000 claims 1
- BEPMXTLHIUWPMV-UHFFFAOYSA-N 2-(4-azaspiro[2.5]octan-4-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1CC11N(CCCC1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F BEPMXTLHIUWPMV-UHFFFAOYSA-N 0.000 claims 1
- IKQOFRDCWPKREY-UHFFFAOYSA-N 2-(4-chloropiperidin-1-yl)-N-[[2-(trifluoromethyl)phenyl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound ClC1CCN(CC1)C=1N=C(C2=C(N=1)N=CC=C2)NCC1=C(C=CC=C1)C(F)(F)F IKQOFRDCWPKREY-UHFFFAOYSA-N 0.000 claims 1
- LPKJXRDLAZOPDN-UHFFFAOYSA-N 2-(4-chloropiperidin-1-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound ClC1CCN(CC1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F LPKJXRDLAZOPDN-UHFFFAOYSA-N 0.000 claims 1
- VTANMRGWCFNHEW-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-N-[[2-(trifluoromethyl)phenyl]methyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound CN1CCN(CC1)C=1N=C(C2=C(N=1)C=CS2)NCC1=C(C=CC=C1)C(F)(F)F VTANMRGWCFNHEW-UHFFFAOYSA-N 0.000 claims 1
- BWCACWWRNMNRIH-UHFFFAOYSA-N 2-(5-azaspiro[3.4]octan-5-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC(F)(F)C1=NC=CC=C1CNC1=C2C=CC=NC2=NC(=N1)N1CCCC11CCC1 BWCACWWRNMNRIH-UHFFFAOYSA-N 0.000 claims 1
- XMLRHJQAWDAPKV-UHFFFAOYSA-N 2-(6-oxa-3-azabicyclo[3.1.1]heptan-3-yl)-N-[[2-(trifluoromethyl)phenyl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C12CN(CC(O1)C2)C=1N=C(C2=C(N=1)N=CC=C2)NCC1=C(C=CC=C1)C(F)(F)F XMLRHJQAWDAPKV-UHFFFAOYSA-N 0.000 claims 1
- VLOCLNONKBHOOK-UHFFFAOYSA-N 2-(6-oxa-3-azabicyclo[3.1.1]heptan-3-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C12CN(CC(O1)C2)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F VLOCLNONKBHOOK-UHFFFAOYSA-N 0.000 claims 1
- WGUJCAKXTGWEHY-UHFFFAOYSA-N 2-(azetidin-1-yl)-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC(F)(F)c1ncccc1CNc1nc(nc2ncccc12)N1CCC1 WGUJCAKXTGWEHY-UHFFFAOYSA-N 0.000 claims 1
- DOLUKLMIYKUBQO-QWHCGFSZSA-N 2-[(2R,3S)-2,3-dimethylmorpholin-4-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C[C@H]1OCCN([C@H]1C)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F DOLUKLMIYKUBQO-QWHCGFSZSA-N 0.000 claims 1
- IVLIEAXYCYEPEM-UEWDXFNNSA-N 2-[(2S)-2,6-dimethylmorpholin-4-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound CC1O[C@H](CN(C1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)C IVLIEAXYCYEPEM-UEWDXFNNSA-N 0.000 claims 1
- UGEVPNPRKWOSOO-STQMWFEESA-N 2-[(2S,5S)-2,5-dimethylmorpholin-4-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C[C@@H]1OC[C@@H](N(C1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)C UGEVPNPRKWOSOO-STQMWFEESA-N 0.000 claims 1
- PQJLPIIYNBVQMH-KWCCSABGSA-N 2-[(3R)-3,5-dimethylmorpholin-4-yl]-N-[[2-(trifluoromethyl)phenyl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound CC1COC[C@@H](C)N1c1nc(NCc2ccccc2C(F)(F)F)c2cccnc2n1 PQJLPIIYNBVQMH-KWCCSABGSA-N 0.000 claims 1
- AMAWXJQFPPSJBR-GFCCVEGCSA-N 2-[(3R)-3-(difluoromethoxy)pyrrolidin-1-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC(O[C@H]1CN(CC1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)F AMAWXJQFPPSJBR-GFCCVEGCSA-N 0.000 claims 1
- AMAWXJQFPPSJBR-LBPRGKRZSA-N 2-[(3S)-3-(difluoromethoxy)pyrrolidin-1-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC(O[C@@H]1CN(CC1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)F AMAWXJQFPPSJBR-LBPRGKRZSA-N 0.000 claims 1
- RZYQXBXYEZTTKT-UHFFFAOYSA-N 2-[2-(difluoromethyl)morpholin-4-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC(C1OCCN(C1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)F RZYQXBXYEZTTKT-UHFFFAOYSA-N 0.000 claims 1
- GNXJPURPIHZWQY-UHFFFAOYSA-N 2-[2-(trifluoromethoxymethyl)pyrrolidin-1-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC(OCC1N(CCC1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)(F)F GNXJPURPIHZWQY-UHFFFAOYSA-N 0.000 claims 1
- UHQBQBNDQLDHCM-UHFFFAOYSA-N 2-[2-(trifluoromethyl)piperidin-1-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC(C1N(CCCC1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F)(F)F UHQBQBNDQLDHCM-UHFFFAOYSA-N 0.000 claims 1
- KNVXFNFISGXHKG-UHFFFAOYSA-N 2-[3-(fluoromethyl)piperidin-1-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FCC1CN(CCC1)C=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F KNVXFNFISGXHKG-UHFFFAOYSA-N 0.000 claims 1
- PDISQYPXKHPAFH-UHFFFAOYSA-N 2-[3-(trifluoromethoxy)pyrrolidin-1-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC(F)(F)OC1CCN(C1)C1=NC(NCC2=CC=CN=C2C(F)(F)F)=C2C=CC=NC2=N1 PDISQYPXKHPAFH-UHFFFAOYSA-N 0.000 claims 1
- WELZJLZOZPQIFT-UHFFFAOYSA-N 2-[3-(trifluoromethyl)piperidin-1-yl]-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound FC(F)(F)C1CCCN(C1)c1nc(NCc2cccnc2C(F)(F)F)c2cccnc2n1 WELZJLZOZPQIFT-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- JWVZYJOBNNURKC-UHFFFAOYSA-N 2-methyl-N-[[2-(trifluoromethyl)pyridin-3-yl]methyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound CC=1N=C(C2=C(N=1)N=CC=C2)NCC=1C(=NC=CC=1)C(F)(F)F JWVZYJOBNNURKC-UHFFFAOYSA-N 0.000 claims 1
- YWMNMYONCOJLDA-UHFFFAOYSA-N 3-(trifluoromethyl)azetidine Chemical compound FC(F)(F)C1CNC1 YWMNMYONCOJLDA-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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- OSVPKIUXGACABS-UHFFFAOYSA-N N-methyl-N-propan-2-yl-4-[3-[2-(trifluoromethyl)phenyl]morpholin-4-yl]pyrido[2,3-d]pyrimidin-2-amine N-propan-2-yl-4-[3-[2-(trifluoromethyl)phenyl]morpholin-4-yl]pyrido[2,3-d]pyrimidin-2-amine Chemical compound C(C)(C)N(C=1N=C(C2=C(N1)N=CC=C2)N2C(COCC2)C2=C(C=CC=C2)C(F)(F)F)C.C(C)(C)NC=2N=C(C1=C(N2)N=CC=C1)N1C(COCC1)C1=C(C=CC=C1)C(F)(F)F OSVPKIUXGACABS-UHFFFAOYSA-N 0.000 claims 1
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- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
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- 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
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- ZGNXATVKGIJQGC-UHFFFAOYSA-N piperidine-3-carbonitrile Chemical compound N#CC1CCCNC1 ZGNXATVKGIJQGC-UHFFFAOYSA-N 0.000 claims 1
- FPYGYIZVZZXXBO-UHFFFAOYSA-N pyrido[2,3-d]pyrimidin-2-amine Chemical compound C1=CC=NC2=NC(N)=NC=C21 FPYGYIZVZZXXBO-UHFFFAOYSA-N 0.000 claims 1
- DGXAOSOMFMODCF-UHFFFAOYSA-N pyrido[3,2-d]pyrimidin-4-amine Chemical compound C1=CN=C2C(N)=NC=NC2=C1 DGXAOSOMFMODCF-UHFFFAOYSA-N 0.000 claims 1
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| GB201700814D0 (en) * | 2017-01-17 | 2017-03-01 | Liverpool School Tropical Medicine | Compounds |
| PT3814347T (pt) | 2018-06-27 | 2023-07-18 | Bristol Myers Squibb Co | Compostos de naftiridinona úteis como ativadores de células t |
| CN112654621B (zh) | 2018-06-27 | 2024-05-14 | 百时美施贵宝公司 | 可作为t细胞活化剂的经取代萘啶酮化合物 |
| CN109627207A (zh) * | 2018-12-17 | 2019-04-16 | 天津药明康德新药开发有限公司 | 一种3-(二氟甲氧基)哌啶盐酸盐的制备方法 |
| CN109651171A (zh) * | 2019-01-13 | 2019-04-19 | 苏州鹏旭医药科技有限公司 | 依拉戈利及其钠盐的中间体及其盐的制备方法和应用 |
| US12398140B2 (en) | 2019-02-13 | 2025-08-26 | Ptc Therapeutics, Inc. | Substituted pyrrolo [2,3-d]pyrimidines for treating familial dysautonomia |
| EA202192170A1 (ru) | 2019-02-13 | 2021-11-15 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | ТИЕНО[3,2-b]ПИРИДИН-7-АМИНОВЫЕ СОЕДИНЕНИЯ ДЛЯ ЛЕЧЕНИЯ СЕМЕЙНОЙ ВЕГЕТО-СОСУДИСТОЙ ДИСТОНИИ |
| WO2020180768A1 (en) * | 2019-03-01 | 2020-09-10 | Revolution Medicines, Inc. | Bicyclic heteroaryl compounds and uses thereof |
| CN114222741B (zh) * | 2019-05-31 | 2025-12-30 | 奇斯药制品公司 | 作为p2x3抑制剂的吡啶并嘧啶类衍生物 |
| BR112021022099A2 (pt) | 2019-05-31 | 2021-12-28 | Chiesi Farm Spa | Derivados de amino quinazolina como inibidores de p2x3 |
| AR119821A1 (es) | 2019-08-28 | 2022-01-12 | Bristol Myers Squibb Co | Compuestos de piridopirimidinonilo sustituidos útiles como activadores de células t |
| CN115209955A (zh) * | 2019-12-12 | 2022-10-18 | Ptc医疗公司 | 治疗家族性自主神经功能障碍的化合物 |
| CN114846007B (zh) | 2019-12-23 | 2024-11-22 | 百时美施贵宝公司 | 可用作t细胞激活剂的经取代的喹唑啉基化合物 |
| AR120823A1 (es) | 2019-12-23 | 2022-03-23 | Bristol Myers Squibb Co | Compuestos bicíclicos sustituidos útiles como activadores de células t |
| EP4081522A1 (en) | 2019-12-23 | 2022-11-02 | Bristol-Myers Squibb Company | Substituted piperazine derivatives useful as t cell activators |
| TW202208355A (zh) * | 2020-05-04 | 2022-03-01 | 美商安進公司 | 作為骨髓細胞觸發受體2促效劑之雜環化合物及使用方法 |
| WO2022058896A1 (en) * | 2020-09-15 | 2022-03-24 | Cadila Healthcare Limited | Inhibitors of low molecular weight protein tyrosine phosphatase for management of metabolic disorder |
| EP4214204A1 (en) | 2020-09-18 | 2023-07-26 | Bayer Aktiengesellschaft | Pyrido[2,3-d]pyrimidin-4-amines as sos1 inhibitors |
| GB202100635D0 (en) | 2021-01-18 | 2021-03-03 | Liverpool School Tropical Medicine | Compounds and methods for treating or preventing dirofilaria infection in a mammal |
| WO2022171018A1 (zh) * | 2021-02-09 | 2022-08-18 | 苏州泽璟生物制药股份有限公司 | 取代苯并或吡啶并嘧啶胺类抑制剂及其制备方法和应用 |
| US11648254B2 (en) | 2021-03-02 | 2023-05-16 | Kumquat Biosciences Inc. | Substituted pyrido[2,3-d]pyrimidines as inhibitors of Ras pathway signaling |
| EP4074317A1 (en) | 2021-04-14 | 2022-10-19 | Bayer AG | Phosphorus derivatives as novel sos1 inhibitors |
| KR20250004810A (ko) | 2022-04-20 | 2025-01-08 | 컴쿼트 바이오사이언시즈 인크. | 대환식 헤테로환 및 이의 용도 |
| CN115160294B (zh) * | 2022-06-27 | 2023-09-29 | 中山大学 | 一种G9a/GLP共价抑制剂及其制备方法及应用 |
| EP4587439A1 (en) | 2022-09-16 | 2025-07-23 | Bayer Aktiengesellschaft | Sulfone-substituted pyrido[3,4-d]pyrimidine derivatives for the treatment of cancer |
| EP4602049A1 (en) | 2022-10-13 | 2025-08-20 | Bayer Aktiengesellschaft | Sos1 inhibitors |
| TW202430519A (zh) * | 2022-11-28 | 2024-08-01 | 大陸商上海美悅生物科技發展有限公司 | 螺雜環取代的嘧啶類化合物及其製備方法和用途 |
| CN121816352A (zh) * | 2023-07-11 | 2026-04-07 | 泰治疗有限公司 | 包含萘啶或吡啶并吡啶核的化合物作为ptc通读剂 |
| TW202543612A (zh) * | 2024-01-05 | 2025-11-16 | 美商露點治療股份有限公司 | 噻吩并吡啶化合物及其用途 |
| CN119161336B (zh) * | 2024-07-24 | 2025-09-05 | 四川大学 | 一种作为Blimp1抑制剂的小分子化合物及其用途 |
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| PH12012500097A1 (en) * | 2009-07-21 | 2011-01-27 | Shanghai Inst Organic Chem | Potent small molecule inhibitors of autophagy, and methods of use thereof |
| FR2959510B1 (fr) * | 2010-04-28 | 2013-04-26 | Centre Nat Rech Scient | Derives de pyrido[3,2-d]pyrimidine, leurs procedes de preparation et leurs utilisations therapeutiques |
| US20130345249A1 (en) * | 2011-01-15 | 2013-12-26 | The Regents Of The University Of California | Formulations for the prevention and treatment of Wolbachia-related disease |
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| CN110128419A (zh) | 2019-05-17 | 2019-08-16 | 南开大学 | 一类二氟吡唑杂环甲酰胺类衍生物及其制备方法和用途 |
| GB202100635D0 (en) | 2021-01-18 | 2021-03-03 | Liverpool School Tropical Medicine | Compounds and methods for treating or preventing dirofilaria infection in a mammal |
| KR102682408B1 (ko) | 2021-05-12 | 2024-07-05 | 에이치케이이노엔 주식회사 | 신규한 벤조티아졸 유도체, 이의 제조방법 및 이의 간질환 예방 또는 치료 용도 |
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-
2017
- 2017-01-17 GB GBGB1700814.5A patent/GB201700814D0/en not_active Ceased
-
2018
- 2018-01-17 EP EP18721448.1A patent/EP3571204A2/en active Pending
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- 2018-01-17 US US16/478,281 patent/US11518760B2/en active Active
- 2018-01-17 JP JP2019559413A patent/JP7318889B2/ja active Active
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2022
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2023
- 2023-01-16 JP JP2023004747A patent/JP2023052427A/ja not_active Withdrawn
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