JPWO2020203609A5 - - Google Patents
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- Publication number
- JPWO2020203609A5 JPWO2020203609A5 JP2021511897A JP2021511897A JPWO2020203609A5 JP WO2020203609 A5 JPWO2020203609 A5 JP WO2020203609A5 JP 2021511897 A JP2021511897 A JP 2021511897A JP 2021511897 A JP2021511897 A JP 2021511897A JP WO2020203609 A5 JPWO2020203609 A5 JP WO2020203609A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- pyrrolidin
- pyridin
- acetamide
- group
- 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.)
- Ceased
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- -1 cyclic amine Chemical group 0.000 claims 80
- 125000005843 halogen group Chemical group 0.000 claims 75
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 72
- 125000003545 alkoxy group Chemical group 0.000 claims 62
- 125000001072 heteroaryl group Chemical group 0.000 claims 56
- 125000001424 substituent group Chemical group 0.000 claims 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 47
- 125000004432 carbon atom Chemical group C* 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 40
- 125000003277 amino group Chemical group 0.000 claims 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 33
- 125000000217 alkyl group Chemical group 0.000 claims 28
- 125000005842 heteroatom Chemical group 0.000 claims 24
- 125000004429 atom Chemical group 0.000 claims 21
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims 18
- 125000004122 cyclic group Chemical group 0.000 claims 17
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 17
- 239000003814 drug Substances 0.000 claims 17
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 15
- 208000003251 Pruritus Diseases 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 239000001301 oxygen Substances 0.000 claims 12
- 239000011593 sulfur Chemical group 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 125000004754 (C2-C12) dialkylamino group Chemical group 0.000 claims 10
- 125000003282 alkyl amino group Chemical group 0.000 claims 10
- 238000011282 treatment Methods 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 239000004480 active ingredient Substances 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004434 sulfur atom Chemical group 0.000 claims 8
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 7
- 150000001721 carbon Chemical group 0.000 claims 7
- 238000011321 prophylaxis Methods 0.000 claims 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000004442 acylamino group Chemical group 0.000 claims 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 150000004292 cyclic ethers Chemical class 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 229910052805 deuterium Inorganic materials 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 3
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- LZCCUHNVFCXSDQ-OXJNMPFZSA-N (2S)-2-[4-(2-methylpropyl)phenyl]-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]propanamide Chemical compound C(C(C)C)C1=CC=C(C=C1)[C@@H](C(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C LZCCUHNVFCXSDQ-OXJNMPFZSA-N 0.000 claims 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 230000000742 histaminergic effect Effects 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims 2
- VPKVOGHPYSBCSB-GDBMZVCRSA-N (2R)-2-(4-bromophenyl)-2-hydroxy-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound BrC1=CC=C(C=C1)[C@H](C(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)O VPKVOGHPYSBCSB-GDBMZVCRSA-N 0.000 claims 1
- LZCCUHNVFCXSDQ-OXQOHEQNSA-N (2R)-2-[4-(2-methylpropyl)phenyl]-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]propanamide Chemical compound C(C(C)C)C1=CC=C(C=C1)[C@H](C(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C LZCCUHNVFCXSDQ-OXQOHEQNSA-N 0.000 claims 1
- NNYAHVBESXJVRT-IUODEOHRSA-N (2R)-2-[4-(trifluoromethyl)phenyl]-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]propanamide Chemical compound FC(C1=CC=C(C=C1)[C@H](C(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F)C)(F)F NNYAHVBESXJVRT-IUODEOHRSA-N 0.000 claims 1
- YBUSTOFPJHHLMT-IEBWSBKVSA-N (2R)-2-amino-2-(4-cyclopropylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N[C@@H](C(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C1=CC=C(C=C1)C1CC1 YBUSTOFPJHHLMT-IEBWSBKVSA-N 0.000 claims 1
- VPKVOGHPYSBCSB-ZBFHGGJFSA-N (2S)-2-(4-bromophenyl)-2-hydroxy-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound BrC1=CC=C(C=C1)[C@@H](C(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)O VPKVOGHPYSBCSB-ZBFHGGJFSA-N 0.000 claims 1
- NNYAHVBESXJVRT-SWLSCSKDSA-N (2S)-2-[4-(trifluoromethyl)phenyl]-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]propanamide Chemical compound FC(C1=CC=C(C=C1)[C@@H](C(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F)C)(F)F NNYAHVBESXJVRT-SWLSCSKDSA-N 0.000 claims 1
- YBUSTOFPJHHLMT-MJGOQNOKSA-N (2S)-2-amino-2-(4-cyclopropylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N[C@H](C(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C1=CC=C(C=C1)C1CC1 YBUSTOFPJHHLMT-MJGOQNOKSA-N 0.000 claims 1
- FULNBZLGNRIJOJ-OAQYLSRUSA-N (3R)-3-[[2-(4-cyclopropylphenyl)acetyl]amino]-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidine-3-carboxylic acid Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C(=O)O FULNBZLGNRIJOJ-OAQYLSRUSA-N 0.000 claims 1
- FULNBZLGNRIJOJ-NRFANRHFSA-N (3S)-3-[[2-(4-cyclopropylphenyl)acetyl]amino]-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidine-3-carboxylic acid Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C(=O)O FULNBZLGNRIJOJ-NRFANRHFSA-N 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- UEKNQFNCZJPSAM-CQSZACIVSA-N 2-(1,3-benzothiazol-6-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound S1C=NC2=C1C=C(C=C2)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F UEKNQFNCZJPSAM-CQSZACIVSA-N 0.000 claims 1
- ODDFUUBIMQZXAL-CYBMUJFWSA-N 2-(1,3-benzothiazol-6-yl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound S1C=NC2=C1C=C(C=C2)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F ODDFUUBIMQZXAL-CYBMUJFWSA-N 0.000 claims 1
- LSGYWQJRNIUKTD-CYBMUJFWSA-N 2-(1,3-benzoxazol-2-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound O1C(=NC2=C1C=CC=C2)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F LSGYWQJRNIUKTD-CYBMUJFWSA-N 0.000 claims 1
- OOVQKJUMFKRLMP-CQSZACIVSA-N 2-(1,3-benzoxazol-5-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound O1C=NC2=C1C=CC(=C2)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F OOVQKJUMFKRLMP-CQSZACIVSA-N 0.000 claims 1
- YKWNPMLBFDSVMJ-CYBMUJFWSA-N 2-(1,3-benzoxazol-5-yl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound O1C=NC2=C1C=CC(=C2)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F YKWNPMLBFDSVMJ-CYBMUJFWSA-N 0.000 claims 1
- QBUNBZHEMDUBAH-CQSZACIVSA-N 2-(1-methylbenzotriazol-5-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CN1N=NC2=C1C=CC(=C2)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F QBUNBZHEMDUBAH-CQSZACIVSA-N 0.000 claims 1
- RRJBTCMSUVFRBX-CYBMUJFWSA-N 2-(1-methylbenzotriazol-5-yl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CN1N=NC2=C1C=CC(=C2)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F RRJBTCMSUVFRBX-CYBMUJFWSA-N 0.000 claims 1
- AVTYUBHTTUSXBC-CYBMUJFWSA-N 2-(1-methylindazol-5-yl)-N-[(3R)-1-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyrrolidin-3-yl]acetamide Chemical compound CN1N=CC2=CC(=CC=C12)CC(=O)N[C@H]1CN(CC1)C=1SC=C(N=1)C(F)(F)F AVTYUBHTTUSXBC-CYBMUJFWSA-N 0.000 claims 1
- PZBPBSYCDRYNTI-MRXNPFEDSA-N 2-(1-methylindazol-5-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CN1N=CC2=CC(=CC=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F PZBPBSYCDRYNTI-MRXNPFEDSA-N 0.000 claims 1
- GPVHDOMJDQMNJY-OAHLLOKOSA-N 2-(1-methylindazol-5-yl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CN1N=CC2=CC(=CC=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F GPVHDOMJDQMNJY-OAHLLOKOSA-N 0.000 claims 1
- OMYGTVFSCLMLKL-QGZVFWFLSA-N 2-(1-methylindol-5-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CN1C=CC2=CC(=CC=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F OMYGTVFSCLMLKL-QGZVFWFLSA-N 0.000 claims 1
- PEKZEWPWXPGKLJ-MRXNPFEDSA-N 2-(1-methylindol-5-yl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CN1C=CC2=CC(=CC=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F PEKZEWPWXPGKLJ-MRXNPFEDSA-N 0.000 claims 1
- SJSMUPKKIMCBBS-QGZVFWFLSA-N 2-(1-methylindol-6-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CN1C=CC2=CC=C(C=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F SJSMUPKKIMCBBS-QGZVFWFLSA-N 0.000 claims 1
- DMCXFLDVGDIGND-MRXNPFEDSA-N 2-(1-methylindol-6-yl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CN1C=CC2=CC=C(C=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F DMCXFLDVGDIGND-MRXNPFEDSA-N 0.000 claims 1
- GZTUUSYRKFBHFB-OAHLLOKOSA-N 2-(1H-indazol-5-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N1N=CC2=CC(=CC=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F GZTUUSYRKFBHFB-OAHLLOKOSA-N 0.000 claims 1
- LWTAJQJKURCXRK-CQSZACIVSA-N 2-(1H-indazol-5-yl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N1N=CC2=CC(=CC=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F LWTAJQJKURCXRK-CQSZACIVSA-N 0.000 claims 1
- WDCMNIKAOSIDDV-OAHLLOKOSA-N 2-(1H-indazol-6-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N1N=CC2=CC=C(C=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F WDCMNIKAOSIDDV-OAHLLOKOSA-N 0.000 claims 1
- ZWLTZMHTKJIZJW-OAHLLOKOSA-N 2-(1H-indol-3-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N1C=C(C2=CC=CC=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F ZWLTZMHTKJIZJW-OAHLLOKOSA-N 0.000 claims 1
- KUBWBZVJIVYMJX-CYBMUJFWSA-N 2-(1H-indol-6-yl)-N-[(3R)-1-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyrrolidin-3-yl]acetamide Chemical compound C1CN(C[C@@H]1NC(=O)CC2=CC3=C(C=C2)C=CN3)C4=NC(=CS4)C(F)(F)F KUBWBZVJIVYMJX-CYBMUJFWSA-N 0.000 claims 1
- HYAJJHXRHJFLGX-MRXNPFEDSA-N 2-(1H-indol-6-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N1C=CC2=CC=C(C=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F HYAJJHXRHJFLGX-MRXNPFEDSA-N 0.000 claims 1
- JMRYBIAHYOZVEE-OAHLLOKOSA-N 2-(1H-indol-6-yl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N1C=CC2=CC=C(C=C12)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F JMRYBIAHYOZVEE-OAHLLOKOSA-N 0.000 claims 1
- ZPWLOGVIFZZCLF-UHFFFAOYSA-N 2-(1H-indol-6-yl)-N-[1-[5-(trifluoromethyl)pyridin-3-yl]azetidin-3-yl]acetamide Chemical compound N1C=CC2=CC=C(C=C12)CC(=O)NC1CN(C1)C=1C=NC=C(C=1)C(F)(F)F ZPWLOGVIFZZCLF-UHFFFAOYSA-N 0.000 claims 1
- NSGRXAGFCLBDJX-OAHLLOKOSA-N 2-(2-methyl-1,3-benzoxazol-5-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CC=1OC2=C(N=1)C=C(C=C2)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F NSGRXAGFCLBDJX-OAHLLOKOSA-N 0.000 claims 1
- NQDSQROBNPQLHJ-CQSZACIVSA-N 2-(2-methyl-1,3-benzoxazol-5-yl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound CC=1OC2=C(N=1)C=C(C=C2)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F NQDSQROBNPQLHJ-CQSZACIVSA-N 0.000 claims 1
- URQSNDHORQQCIO-OAHLLOKOSA-N 2-(3,5-dichlorophenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound ClC=1C=C(C=C(C=1)Cl)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F URQSNDHORQQCIO-OAHLLOKOSA-N 0.000 claims 1
- GFDAZZJDQIASOM-OAHLLOKOSA-N 2-(3-chloro-5-fluorophenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound ClC=1C=C(C=C(C=1)F)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F GFDAZZJDQIASOM-OAHLLOKOSA-N 0.000 claims 1
- WBQFHLKLXPTQAK-QGZVFWFLSA-N 2-(4-acetamidophenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C(C)(=O)NC1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F WBQFHLKLXPTQAK-QGZVFWFLSA-N 0.000 claims 1
- NHAJTAPXLSYLTJ-OAHLLOKOSA-N 2-(4-aminophenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound NC1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F NHAJTAPXLSYLTJ-OAHLLOKOSA-N 0.000 claims 1
- ZJAJGUYNDWCAQZ-OAHLLOKOSA-N 2-(4-bromophenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound BrC1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F ZJAJGUYNDWCAQZ-OAHLLOKOSA-N 0.000 claims 1
- UFLHOFAWYWPGRQ-LJQANCHMSA-N 2-(4-cyclopropylphenyl)-2-methyl-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]propanamide Chemical compound C1(CC1)C1=CC=C(C=C1)C(C(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)(C)C UFLHOFAWYWPGRQ-LJQANCHMSA-N 0.000 claims 1
- WDAUSACOYODRSK-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-(3-hydroxyphenyl)pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C1=CC(=CC=C1)O WDAUSACOYODRSK-GOSISDBHSA-N 0.000 claims 1
- JGUQINLVZPLNPD-LJQANCHMSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-(3-methoxyphenyl)pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C1=CC(=CC=C1)OC JGUQINLVZPLNPD-LJQANCHMSA-N 0.000 claims 1
- QDHXLFUMPOPBIM-QGZVFWFLSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-(4,6-dimethoxypyrimidin-2-yl)pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C1=NC(=CC(=N1)OC)OC QDHXLFUMPOPBIM-QGZVFWFLSA-N 0.000 claims 1
- FIBPMHMDNDUSAZ-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-(6-fluoro-1,3-benzothiazol-2-yl)pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1SC2=C(N=1)C=CC(=C2)F FIBPMHMDNDUSAZ-GOSISDBHSA-N 0.000 claims 1
- ZKDQIHPIYXNTRB-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[1-oxido-5-(trifluoromethyl)pyridin-1-ium-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=[N+](C=C(C=1)C(F)(F)F)[O-] ZKDQIHPIYXNTRB-GOSISDBHSA-N 0.000 claims 1
- UDQOIFRFBNWBSQ-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[2-methoxy-5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C(=NC=C(C=1)C(F)(F)F)OC UDQOIFRFBNWBSQ-GOSISDBHSA-N 0.000 claims 1
- IGYOXCAZOJDHFE-LJQANCHMSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[3-fluoro-5-(trifluoromethyl)phenyl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C1=CC(=CC(=C1)C(F)(F)F)F IGYOXCAZOJDHFE-LJQANCHMSA-N 0.000 claims 1
- DCWCNBNASRYUAL-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[4-(2,2,2-trifluoroethoxy)pyridin-2-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C1=NC=CC(=C1)OCC(F)(F)F DCWCNBNASRYUAL-GOSISDBHSA-N 0.000 claims 1
- UYKYFTVSMYWYCX-OAHLLOKOSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[4-(trifluoromethyl)-1,3-oxazol-2-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1OC=C(N=1)C(F)(F)F UYKYFTVSMYWYCX-OAHLLOKOSA-N 0.000 claims 1
- FVHIXHPRCIZKGI-OAHLLOKOSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1SC=C(N=1)C(F)(F)F FVHIXHPRCIZKGI-OAHLLOKOSA-N 0.000 claims 1
- AVCGLFMLHQVAEE-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[4-(trifluoromethyl)pyridin-2-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C1=NC=CC(=C1)C(F)(F)F AVCGLFMLHQVAEE-GOSISDBHSA-N 0.000 claims 1
- AOJYOXHDAAIYRF-QGZVFWFLSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[4-fluoro-3-(trifluoromethyl)phenyl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C1=CC(=C(C=C1)F)C(F)(F)F AOJYOXHDAAIYRF-QGZVFWFLSA-N 0.000 claims 1
- WZDPLGIQDDSJME-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[5-(2,2,2-trifluoroethoxy)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)OCC(F)(F)F WZDPLGIQDDSJME-GOSISDBHSA-N 0.000 claims 1
- GBPIFKFAFYSFGE-HXUWFJFHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[5-(2-hydroxypropan-2-yl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(C)(C)O GBPIFKFAFYSFGE-HXUWFJFHSA-N 0.000 claims 1
- YKAKRPRSCQNXCY-LJQANCHMSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]piperidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CCC1)C=1C=NC=C(C=1)C(F)(F)F YKAKRPRSCQNXCY-LJQANCHMSA-N 0.000 claims 1
- GJEJGSQANGCSNV-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F GJEJGSQANGCSNV-GOSISDBHSA-N 0.000 claims 1
- KGHHDCQUISGCFL-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)OCC(F)(F)F KGHHDCQUISGCFL-GOSISDBHSA-N 0.000 claims 1
- KODNMVFTSUSOOH-QGZVFWFLSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-2-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C1=NC(=CC=C1)C(F)(F)F KODNMVFTSUSOOH-QGZVFWFLSA-N 0.000 claims 1
- FOPYXEVCXRPIIO-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]piperidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CCC1)C=1C=NC(=CC=1)C(F)(F)F FOPYXEVCXRPIIO-GOSISDBHSA-N 0.000 claims 1
- QBEZUDILBMAIMQ-QGZVFWFLSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F QBEZUDILBMAIMQ-QGZVFWFLSA-N 0.000 claims 1
- IRGGAUGMRGRZBO-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[6-methyl-5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=C(C=1)C(F)(F)F)C IRGGAUGMRGRZBO-GOSISDBHSA-N 0.000 claims 1
- KZFHVFNIUNFSQA-GOSISDBHSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-[8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=C(C=2N(C=1)C=CN=2)C(F)(F)F KZFHVFNIUNFSQA-GOSISDBHSA-N 0.000 claims 1
- DGNZKRPILAMJRK-XZATXCMXSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-1-oxido-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-1-ium-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1C[N+](CC1)(C=1C=NC=C(C=1)C(F)(F)F)[O-] DGNZKRPILAMJRK-XZATXCMXSA-N 0.000 claims 1
- RDVHYCWUHMDSPC-OAQYLSRUSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-3-(hydroxymethyl)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)CO RDVHYCWUHMDSPC-OAQYLSRUSA-N 0.000 claims 1
- NTCCROWNPYDEMU-JOCHJYFZSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-3-(methoxymethyl)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)COC NTCCROWNPYDEMU-JOCHJYFZSA-N 0.000 claims 1
- MWJAAADSQFNRAI-JOCHJYFZSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-3-ethyl-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)CC MWJAAADSQFNRAI-JOCHJYFZSA-N 0.000 claims 1
- MTKMKAINCDMKGY-OAQYLSRUSA-N 2-(4-cyclopropylphenyl)-N-[(3R)-3-methyl-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C MTKMKAINCDMKGY-OAQYLSRUSA-N 0.000 claims 1
- UEQGNNJSNSWTCW-IFXJQAMLSA-N 2-(4-cyclopropylphenyl)-N-[(3R,5S)-5-methyl-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN([C@H](C1)C)C=1C=NC=C(C=1)C(F)(F)F UEQGNNJSNSWTCW-IFXJQAMLSA-N 0.000 claims 1
- RDVHYCWUHMDSPC-NRFANRHFSA-N 2-(4-cyclopropylphenyl)-N-[(3S)-3-(hydroxymethyl)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)CO RDVHYCWUHMDSPC-NRFANRHFSA-N 0.000 claims 1
- NTCCROWNPYDEMU-QFIPXVFZSA-N 2-(4-cyclopropylphenyl)-N-[(3S)-3-(methoxymethyl)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)COC NTCCROWNPYDEMU-QFIPXVFZSA-N 0.000 claims 1
- MWJAAADSQFNRAI-QFIPXVFZSA-N 2-(4-cyclopropylphenyl)-N-[(3S)-3-ethyl-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)CC MWJAAADSQFNRAI-QFIPXVFZSA-N 0.000 claims 1
- ABOCAGWOALKSGE-OALUTQOASA-N 2-(4-cyclopropylphenyl)-N-[(3S,4S)-4-fluoro-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(C[C@@H]1F)C=1C=NC=C(C=1)C(F)(F)F ABOCAGWOALKSGE-OALUTQOASA-N 0.000 claims 1
- XQXIPYNCILAXQX-OALUTQOASA-N 2-(4-cyclopropylphenyl)-N-[(3S,4S)-4-hydroxy-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(C[C@@H]1O)C=1C=NC=C(C=1)C(F)(F)F XQXIPYNCILAXQX-OALUTQOASA-N 0.000 claims 1
- LVSOSABREAYEMP-INIZCTEOSA-N 2-(4-cyclopropylphenyl)-N-[(7R)-5-[4-(trifluoromethyl)-1,3-thiazol-2-yl]-5-azaspiro[2.4]heptan-7-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC11CC1)C=1SC=C(N=1)C(F)(F)F LVSOSABREAYEMP-INIZCTEOSA-N 0.000 claims 1
- DLFMWJNHUIWGNU-FQEVSTJZSA-N 2-(4-cyclopropylphenyl)-N-[(7R)-5-[5-(trifluoromethyl)pyridin-3-yl]-5-azaspiro[2.4]heptan-7-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC11CC1)C=1C=NC=C(C=1)C(F)(F)F DLFMWJNHUIWGNU-FQEVSTJZSA-N 0.000 claims 1
- ZCZFCKLLZQNWKY-FQEVSTJZSA-N 2-(4-cyclopropylphenyl)-N-[(7R)-5-[6-(trifluoromethyl)pyridin-3-yl]-5-azaspiro[2.4]heptan-7-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC11CC1)C=1C=NC(=CC=1)C(F)(F)F ZCZFCKLLZQNWKY-FQEVSTJZSA-N 0.000 claims 1
- JQZPHDDVBSZXAG-UHFFFAOYSA-N 2-(4-cyclopropylphenyl)-N-[1-[4-(trifluoromethyl)phenyl]azetidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)NC1CN(C1)C1=CC=C(C=C1)C(F)(F)F JQZPHDDVBSZXAG-UHFFFAOYSA-N 0.000 claims 1
- CNINSVNNTDQRRX-UHFFFAOYSA-N 2-(4-cyclopropylphenyl)-N-[1-[4-fluoro-3-(trifluoromethyl)phenyl]azetidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)NC1CN(C1)C1=CC(=C(C=C1)F)C(F)(F)F CNINSVNNTDQRRX-UHFFFAOYSA-N 0.000 claims 1
- LBBOFFGLAFIYJI-UHFFFAOYSA-N 2-(4-cyclopropylphenyl)-N-[3-(trifluoromethyl)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C1(CC1)C1=CC=C(C=C1)CC(=O)NC1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C(F)(F)F LBBOFFGLAFIYJI-UHFFFAOYSA-N 0.000 claims 1
- OECQJPPJRWGBNE-CQSZACIVSA-N 2-(4-hydroxyphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound OC1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F OECQJPPJRWGBNE-CQSZACIVSA-N 0.000 claims 1
- ZCVJXKSSDBZYOK-OAHLLOKOSA-N 2-(4-morpholin-4-ylphenyl)-N-[(3R)-1-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyrrolidin-3-yl]acetamide Chemical compound O1CCN(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1SC=C(N=1)C(F)(F)F ZCVJXKSSDBZYOK-OAHLLOKOSA-N 0.000 claims 1
- IMBSHSZGBQNYTE-GOSISDBHSA-N 2-(4-morpholin-4-ylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound O1CCN(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F IMBSHSZGBQNYTE-GOSISDBHSA-N 0.000 claims 1
- ARQOYDRPKZEWHR-QGZVFWFLSA-N 2-(4-morpholin-4-ylphenyl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound O1CCN(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F ARQOYDRPKZEWHR-QGZVFWFLSA-N 0.000 claims 1
- QDAMZTMTOZBFMT-CQSZACIVSA-N 2-(4-nitrophenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F QDAMZTMTOZBFMT-CQSZACIVSA-N 0.000 claims 1
- LULZTENTLUNLIM-GOSISDBHSA-N 2-(4-piperazin-1-ylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N1(CCNCC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F LULZTENTLUNLIM-GOSISDBHSA-N 0.000 claims 1
- JRDAHZLQLICUJD-MRXNPFEDSA-N 2-(4-propan-2-ylphenyl)-N-[(3R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]pyrrolidin-3-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=NC=1)C(F)(F)F JRDAHZLQLICUJD-MRXNPFEDSA-N 0.000 claims 1
- FGQQCDJWWXODAR-OAHLLOKOSA-N 2-(4-propan-2-ylphenyl)-N-[(3R)-1-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyrrolidin-3-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1SC=C(N=1)C(F)(F)F FGQQCDJWWXODAR-OAHLLOKOSA-N 0.000 claims 1
- RHTXGAUOHUASKP-GOSISDBHSA-N 2-(4-propan-2-ylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F RHTXGAUOHUASKP-GOSISDBHSA-N 0.000 claims 1
- XMISBVRVHJYGGM-QGZVFWFLSA-N 2-(4-propan-2-ylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyrimidin-2-yl]pyrrolidin-3-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C1=NC=C(C=N1)C(F)(F)F XMISBVRVHJYGGM-QGZVFWFLSA-N 0.000 claims 1
- AXZHHLIDHMWWRZ-MRXNPFEDSA-N 2-(4-propan-2-ylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)thiophen-2-yl]pyrrolidin-3-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1SC(=CC=1)C(F)(F)F AXZHHLIDHMWWRZ-MRXNPFEDSA-N 0.000 claims 1
- QDAJPCRCVXEEJB-QGZVFWFLSA-N 2-(4-propan-2-ylphenyl)-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F QDAJPCRCVXEEJB-QGZVFWFLSA-N 0.000 claims 1
- RHTXGAUOHUASKP-SFHVURJKSA-N 2-(4-propan-2-ylphenyl)-N-[(3S)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)N[C@@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F RHTXGAUOHUASKP-SFHVURJKSA-N 0.000 claims 1
- HWTZZDJFLFFNOC-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)-N-[1-[5-(trifluoromethyl)pyridin-3-yl]azetidin-3-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)NC1CN(C1)C=1C=NC=C(C=1)C(F)(F)F HWTZZDJFLFFNOC-UHFFFAOYSA-N 0.000 claims 1
- XMGKPQYXTUBDER-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)-N-[1-[5-(trifluoromethyl)pyridin-3-yl]piperidin-4-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)NC1CCN(CC1)C=1C=NC=C(C=1)C(F)(F)F XMGKPQYXTUBDER-UHFFFAOYSA-N 0.000 claims 1
- GCXGNXIPPLZIFS-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)-N-[1-[6-(trifluoromethyl)pyridin-3-yl]azetidin-3-yl]acetamide Chemical compound C(C)(C)C1=CC=C(C=C1)CC(=O)NC1CN(C1)C=1C=NC(=CC=1)C(F)(F)F GCXGNXIPPLZIFS-UHFFFAOYSA-N 0.000 claims 1
- OWUQMUIISZFFSC-QGZVFWFLSA-N 2-(4-pyrazol-1-ylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N1(N=CC=C1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F OWUQMUIISZFFSC-QGZVFWFLSA-N 0.000 claims 1
- VEAPPNOMOUEGIF-GOSISDBHSA-N 2-(4-pyrrolidin-1-ylphenyl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound N1(CCCC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F VEAPPNOMOUEGIF-GOSISDBHSA-N 0.000 claims 1
- XISORIBOUVOTSR-CYBMUJFWSA-N 2-(6-chloro-1,3-benzoxazol-2-yl)-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound ClC1=CC2=C(N=C(O2)CC(=O)N[C@H]2CN(CC2)C=2C=NC=C(C=2)C(F)(F)F)C=C1 XISORIBOUVOTSR-CYBMUJFWSA-N 0.000 claims 1
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- DBASRTFKIQKQLP-CQSZACIVSA-N 2-[2-fluoro-4-(trifluoromethyl)phenyl]-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F DBASRTFKIQKQLP-CQSZACIVSA-N 0.000 claims 1
- FNXYWPKNZNKUOR-CYBMUJFWSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound FC=1C=C(C=CC=1C(F)(F)F)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F FNXYWPKNZNKUOR-CYBMUJFWSA-N 0.000 claims 1
- AUZGBEVWHWEWKE-HXUWFJFHSA-N 2-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound O1CCOC11CCN(CC1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F AUZGBEVWHWEWKE-HXUWFJFHSA-N 0.000 claims 1
- MTONJVRCUIAJSY-OAHLLOKOSA-N 2-[4-(2,2,2-trifluoroethoxy)phenyl]-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound FC(COC1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)(F)F MTONJVRCUIAJSY-OAHLLOKOSA-N 0.000 claims 1
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- YUKMCGTVLPDRHT-MDMXATFFSA-N 2-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)phenyl]-N-[(3R)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound C12COCC(CC1)N2C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC(=CC=1)C(F)(F)F YUKMCGTVLPDRHT-MDMXATFFSA-N 0.000 claims 1
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- ZOJGKURWXFLTIR-DUXKGJEZSA-N 2-[4-[(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]phenyl]-N-[(3R)-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]acetamide Chemical compound [C@H]12OC[C@H](N(C1)C1=CC=C(C=C1)CC(=O)N[C@H]1CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C2 ZOJGKURWXFLTIR-DUXKGJEZSA-N 0.000 claims 1
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- HLLXTNSFJAHREN-JOCHJYFZSA-N N-[(3R)-3-methyl-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]-2-(4-morpholin-4-ylphenyl)acetamide Chemical compound C[C@@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)NC(CC1=CC=C(C=C1)N1CCOCC1)=O HLLXTNSFJAHREN-JOCHJYFZSA-N 0.000 claims 1
- SIASAVALYVVZKG-OAQYLSRUSA-N N-[(3S)-3-cyano-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]-2-(4-cyclopropylphenyl)acetamide Chemical compound C(#N)[C@]1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)NC(CC1=CC=C(C=C1)C1CC1)=O SIASAVALYVVZKG-OAQYLSRUSA-N 0.000 claims 1
- MEPMEZVDGUEQLS-SQNIBIBYSA-N O=C([C@@H](C1)[C@H]1C1=NC(C=CC=C2)=C2N1)N[C@H](CC1)CN1C(C=C1)=NC(C=C2)=C1C=C2F Chemical compound O=C([C@@H](C1)[C@H]1C1=NC(C=CC=C2)=C2N1)N[C@H](CC1)CN1C(C=C1)=NC(C=C2)=C1C=C2F MEPMEZVDGUEQLS-SQNIBIBYSA-N 0.000 claims 1
- WGYYRDMJGLHOJG-KBMXLJTQSA-N O=C([C@@H](C1)[C@H]1C1=NC(C=CC=C2)=C2N1)N[C@H](CC1)CN1C1=CC(Br)=CN=C1 Chemical compound O=C([C@@H](C1)[C@H]1C1=NC(C=CC=C2)=C2N1)N[C@H](CC1)CN1C1=CC(Br)=CN=C1 WGYYRDMJGLHOJG-KBMXLJTQSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- MIUQCYLPTIQREX-HSZRJFAPSA-N [(3R)-3-[[2-(4-cyclopropylphenyl)acetyl]amino]-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methyl acetate Chemical compound CC(=O)OC[C@]1(CCN(C1)C2=CN=CC(=C2)C(F)(F)F)NC(=O)CC3=CC=C(C=C3)C4CC4 MIUQCYLPTIQREX-HSZRJFAPSA-N 0.000 claims 1
- MIUQCYLPTIQREX-QHCPKHFHSA-N [(3S)-3-[[2-(4-cyclopropylphenyl)acetyl]amino]-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methyl acetate Chemical compound CC(=O)OC[C@@]1(CCN(C1)C2=CN=CC(=C2)C(F)(F)F)NC(=O)CC3=CC=C(C=C3)C4CC4 MIUQCYLPTIQREX-QHCPKHFHSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229960001340 histamine Drugs 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- MIIPGQCPLJQCSQ-UHFFFAOYSA-N methyl 3-[[2-(4-morpholin-4-ylphenyl)acetyl]amino]-1-[5-(trifluoromethyl)pyridin-3-yl]pyrrolidine-3-carboxylate Chemical compound O1CCN(CC1)C1=CC=C(C=C1)CC(=O)NC1(CN(CC1)C=1C=NC=C(C=1)C(F)(F)F)C(=O)OC MIIPGQCPLJQCSQ-UHFFFAOYSA-N 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 150000004892 pyridazines Chemical class 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
- 229930192474 thiophene Natural products 0.000 claims 1
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| US20250129021A1 (en) * | 2023-09-19 | 2025-04-24 | Interdict Bio, Inc. | Small molecule protein synthesis modulators |
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| DE2831447A1 (de) * | 1978-07-18 | 1980-01-31 | Hoechst Ag | 2-(4-aminopiperidino)-3,4-dihydrochinoline und verfahren zu ihrer herstellung |
| DE69732868T2 (de) * | 1996-11-25 | 2006-04-13 | Toray Industries, Inc. | Mittel gegen Juckreiz |
| JP2002088073A (ja) * | 2000-09-08 | 2002-03-27 | Yamanouchi Pharmaceut Co Ltd | 抗アンドロゲン剤 |
| JP4775259B2 (ja) * | 2004-03-31 | 2011-09-21 | 味の素株式会社 | アニリン誘導体 |
| AU2005273986A1 (en) * | 2004-08-10 | 2006-02-23 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| US20070004763A1 (en) * | 2005-06-10 | 2007-01-04 | Nand Baindur | Aminoquinoline and aminoquinazoline kinase modulators |
| US8030501B2 (en) | 2006-07-28 | 2011-10-04 | Kaneka Corporation | Process for producing optically active 3-amino nitrogen-containing compounds |
| DE102007018151A1 (de) | 2007-04-16 | 2008-10-23 | Günenthal GmbH | Neue Vanilloid-Rezeptor Liganden und ihre Verwendung zur Herstellung von Arzneimitteln |
| WO2009131196A1 (ja) * | 2008-04-24 | 2009-10-29 | 武田薬品工業株式会社 | 置換ピロリジン誘導体およびその用途 |
| MX2011005954A (es) | 2008-12-05 | 2011-10-11 | Astellas Pharma Inc | Compuesto de 2h-cromeno y su derivado. |
| JP2013028537A (ja) * | 2009-11-11 | 2013-02-07 | Dainippon Sumitomo Pharma Co Ltd | Ｎ−ベンジルアミド誘導体およびそれを含有する医薬組成物 |
| ES2617339T3 (es) * | 2010-12-16 | 2017-06-16 | Calchan Limited | Derivados de pirrolopirimidina inhibidores de ASK1 |
| BR112013021675A2 (pt) | 2011-02-25 | 2016-11-01 | Array Biopharma Inc | compostos de triazolopiridina como inibidores de pim cinase |
| AR085435A1 (es) | 2011-03-17 | 2013-10-02 | Bristol Myers Squibb Co | Inhibidores de pirrolopiridazina jak3 y su uso para el tratamiento de enfermedades inflamatorias y autoinmunes |
| WO2013026914A1 (en) | 2011-08-25 | 2013-02-28 | F. Hoffmann-La Roche Ag | Serine/threonine pak1 inhibitors |
| EP2790705B1 (en) | 2011-12-15 | 2017-12-06 | Novartis AG | Use of inhibitors of the activity or function of pi3k |
| CN104603098B (zh) | 2012-03-30 | 2016-06-29 | 桑多斯股份公司 | 2-(3,4-二氟苯基)环丙胺衍生物和盐的合成 |
| WO2014010748A1 (en) | 2012-07-10 | 2014-01-16 | Shionogi & Co., Ltd. | Cyclopropane derivative having bace1 inhibiting activity |
| EP3391898A3 (en) | 2013-03-13 | 2019-02-13 | President and Fellows of Harvard College | Stapled and stitched polypeptides and uses thereof |
| DK3027615T3 (da) * | 2013-08-02 | 2021-10-25 | Pasteur Institut Korea | Antiinfektionsforbindelser |
| ES2670550T3 (es) * | 2013-10-14 | 2018-05-30 | Eisai R&D Management Co., Ltd. | Derivados de quinolina selectivamente sustituidos |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| NO2721710T3 (https=) | 2014-08-21 | 2018-03-31 | ||
| WO2016095204A1 (en) | 2014-12-19 | 2016-06-23 | Merck Sharp & Dohme Corp. | Pyrrolidine orexin receptor antagonists |
| CN105837577B (zh) * | 2015-02-02 | 2019-01-25 | 四川大学 | 1-(嘧啶-4-基)3-胺基哌啶衍生物及其制备方法和用途 |
| PT3889145T (pt) * | 2015-12-17 | 2024-04-02 | Merck Patent Gmbh | 8-ciano-5-piperidino-quinolinas como antagonistas de tlr7/8 e suas utilizações para tratamento de distúrbios imunitários |
| EP3404021A4 (en) | 2016-01-12 | 2019-09-11 | Nippon Chemiphar Co., Ltd. | VOLTAGE-RELATED T-TYPE CALCIUM CHANNEL INHIBITOR |
| US10973913B2 (en) * | 2016-02-16 | 2021-04-13 | Washington University | JAK inhibitors and uses thereof |
| CN105906545B (zh) | 2016-05-06 | 2018-06-29 | 广州康瑞泰药业有限公司 | 一种合成西他沙星中间体(7s)-5-氮杂螺[2.4]庚烷-7-基氨基甲酸叔丁酯的制备方法 |
| SG11201811023UA (en) * | 2016-06-23 | 2019-01-30 | St Jude Childrens Res Hospital | Small molecule modulators of pantothenate kinases |
| CN107556318B (zh) * | 2017-08-22 | 2020-08-11 | 山东大学 | 一种含哌啶的吡咯并嘧啶类化合物及其制备方法与应用 |
| JP7527967B2 (ja) * | 2017-12-27 | 2024-08-05 | セント ジュード チルドレンズ リサーチ ホスピタル，インコーポレイティド | Ｃａｓｔｏｒに関連する障害を治療する方法 |
| WO2019133635A1 (en) * | 2017-12-27 | 2019-07-04 | St. Jude Children's Research Hospital | Small molecule modulators of pantothenate kinases |
| US20220363667A1 (en) * | 2018-07-17 | 2022-11-17 | Nippon Chemiphar Co., Ltd. | T-type calcium channel blocker |
| CA3108099A1 (en) * | 2018-07-31 | 2020-02-06 | Merck Patent Gmbh | Tlr7/8 antagonists and uses thereof |
-
2020
- 2020-03-26 AU AU2020250468A patent/AU2020250468A1/en not_active Abandoned
- 2020-03-26 EP EP20783736.0A patent/EP3950059A4/en not_active Withdrawn
- 2020-03-26 JP JP2021511897A patent/JPWO2020203609A1/ja not_active Ceased
- 2020-03-26 WO PCT/JP2020/013542 patent/WO2020203609A1/ja not_active Ceased
- 2020-03-26 CA CA3135344A patent/CA3135344A1/en active Pending
- 2020-03-26 US US17/599,271 patent/US20220226299A1/en not_active Abandoned
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