CA3053781A1 - Benzopyran and naphalene derivatives and their uses as calium channel inhibitors - Google Patents
Benzopyran and naphalene derivatives and their uses as calium channel inhibitors Download PDFInfo
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- CA3053781A1 CA3053781A1 CA3053781A CA3053781A CA3053781A1 CA 3053781 A1 CA3053781 A1 CA 3053781A1 CA 3053781 A CA3053781 A CA 3053781A CA 3053781 A CA3053781 A CA 3053781A CA 3053781 A1 CA3053781 A1 CA 3053781A1
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- ethyl
- compound
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- methyl
- fluoro
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- 239000003112 inhibitor Substances 0.000 title description 12
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 274
- 238000000034 method Methods 0.000 claims abstract description 61
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 58
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 55
- 201000010099 disease Diseases 0.000 claims abstract description 35
- 108010029485 Protein Isoforms Proteins 0.000 claims abstract description 20
- 102000001708 Protein Isoforms Human genes 0.000 claims abstract description 20
- 201000011510 cancer Diseases 0.000 claims abstract description 20
- 102000038650 voltage-gated calcium channel activity Human genes 0.000 claims abstract description 19
- 108091023044 voltage-gated calcium channel activity Proteins 0.000 claims abstract description 19
- 230000000694 effects Effects 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims description 113
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 112
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 89
- -1 N,N-dimethylaminoethyl Chemical group 0.000 claims description 84
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 63
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 34
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 208000035475 disorder Diseases 0.000 claims description 23
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
- 102000003691 T-Type Calcium Channels Human genes 0.000 claims description 19
- 108090000030 T-Type Calcium Channels Proteins 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 101000932804 Homo sapiens Voltage-dependent T-type calcium channel subunit alpha-1H Proteins 0.000 claims description 12
- 102100025482 Voltage-dependent T-type calcium channel subunit alpha-1H Human genes 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 230000002062 proliferating effect Effects 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 230000001413 cellular effect Effects 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- 208000032612 Glial tumor Diseases 0.000 claims description 8
- 206010018338 Glioma Diseases 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 208000005017 glioblastoma Diseases 0.000 claims description 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 201000002528 pancreatic cancer Diseases 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 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 description 2
- 230000009286 beneficial effect Effects 0.000 claims 3
- PGYUQGFDDASGEV-ZJJOJAIXSA-N CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3)N(CCN5CCCC5)C(=O)O)C=C(C=C2)F Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3)N(CCN5CCCC5)C(=O)O)C=C(C=C2)F PGYUQGFDDASGEV-ZJJOJAIXSA-N 0.000 claims 1
- KACLPRAVVJRTKQ-IUDBTDONSA-N CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3)N(CCOC)C(=O)O)C=C(C=C2)F Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3)N(CCOC)C(=O)O)C=C(C=C2)F KACLPRAVVJRTKQ-IUDBTDONSA-N 0.000 claims 1
- MUTYKRZQUIELTH-ZJJOJAIXSA-N CCN(CC)CCN(C(=O)O)[C@@]1(CCC2=C([C@@H]1C(C)C)C=CC(=C2)F)CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3 Chemical compound CCN(CC)CCN(C(=O)O)[C@@]1(CCC2=C([C@@H]1C(C)C)C=CC(=C2)F)CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3 MUTYKRZQUIELTH-ZJJOJAIXSA-N 0.000 claims 1
- HNRWFXOJXHBBEU-CYTLCNBWSA-N [(1R,2R)-2-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] morpholine-4-carboxylate Chemical compound CC(C)[C@@H]1C2=C(CC[C@]1(CCN(C)CCCC1=NC3=C(C)C=CC(C)=C3N1)OC(=O)N1CCOCC1)C=C(F)C=C2 HNRWFXOJXHBBEU-CYTLCNBWSA-N 0.000 claims 1
- HBMQEVIYJYANIK-ZQAZVOLISA-N [(1S,2S)-2-[2-[2-[1-(1H-benzimidazol-2-yl)cyclopropyl]ethyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] morpholine-4-carboxylate Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC1(CC1)C1=NC3=CC=CC=C3N1)OC(=O)N1CCOCC1)C=C(F)C=C2 HBMQEVIYJYANIK-ZQAZVOLISA-N 0.000 claims 1
- QXTDJAVLEBMRMO-XCZPVHLTSA-N [(1S,2S)-2-[2-[3-(1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-methylcarbamate Chemical compound N1C2=C(N=C1CCCN(CC[C@@]1([C@H](C3=CC=C(C=C3CC1)F)C(C)C)OC(=O)NC)C)C=CC=C2 QXTDJAVLEBMRMO-XCZPVHLTSA-N 0.000 claims 1
- SFIKITTVBPYPRG-YZNIXAGQSA-N [(1S,2S)-2-[2-[3-(4,7-dimethoxy-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-methylcarbamate Chemical compound CNC(=O)O[C@]1(CCN(C)CCCC2=NC3=C(OC)C=CC(OC)=C3N2)CCC2=C(C=CC(F)=C2)[C@@H]1C(C)C SFIKITTVBPYPRG-YZNIXAGQSA-N 0.000 claims 1
- SSNFLHSDRULAEG-DHIFEGFHSA-N [(1S,2S)-2-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N,N-dimethylcarbamate Chemical compound N1C2=C(N=C1CCCN(CC[C@@]1([C@H](C3=CC=C(F)C=C3CC1)C(C)C)OC(=O)N(C)C)C)C(C)=CC=C2C SSNFLHSDRULAEG-DHIFEGFHSA-N 0.000 claims 1
- XSOCXUJWAGDABV-YZNIXAGQSA-N [(1S,2S)-2-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-methylcarbamate Chemical compound CNC(=O)O[C@]1(CCN(C)CCCC2=NC3=C(C)C=CC(C)=C3N2)CCC2=C(C=CC(F)=C2)[C@@H]1C(C)C XSOCXUJWAGDABV-YZNIXAGQSA-N 0.000 claims 1
- HNRWFXOJXHBBEU-ZQAZVOLISA-N [(1S,2S)-2-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] morpholine-4-carboxylate Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC1=NC3=C(C)C=CC(C)=C3N1)OC(=O)N1CCOCC1)C=C(F)C=C2 HNRWFXOJXHBBEU-ZQAZVOLISA-N 0.000 claims 1
- CLXHMYPWWWNRKP-YZNIXAGQSA-N [(1S,2S)-2-[2-[3-(4-chloro-7-methoxy-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N,N-dimethylcarbamate Chemical compound N1C2=C(N=C1CCCN(CC[C@@]1([C@H](C3=CC=C(F)C=C3CC1)C(C)C)OC(=O)N(C)C)C)C(OC)=CC=C2Cl CLXHMYPWWWNRKP-YZNIXAGQSA-N 0.000 claims 1
- QOYMIFRPTIARMA-IZEXYCQBSA-N [(1S,2S)-2-[2-[3-[4,6-bis(trifluoromethyl)-1H-benzimidazol-2-yl]propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] morpholine-4-carboxylate Chemical compound C1=C(C=C(C2=C1NC(=N2)CCCN(CC[C@@]1([C@H](C2=CC=C(F)C=C2CC1)C(C)C)OC(=O)N1CCOCC1)C)C(F)(F)F)C(F)(F)F QOYMIFRPTIARMA-IZEXYCQBSA-N 0.000 claims 1
- PRAYESAWARLJBE-ZQAZVOLISA-N [(1S,2S)-2-[2-[[3-(1H-benzimidazol-2-yl)-3-methylbutyl]-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-[2-(dimethylamino)ethyl]carbamate Chemical compound N1C2=C(N=C1C(CCN(CC[C@@]1([C@H](C3=C(C=C(F)C=C3)CC1)C(C)C)OC(=O)NCCN(C)C)C)(C)C)C=CC=C2 PRAYESAWARLJBE-ZQAZVOLISA-N 0.000 claims 1
- LXQJMLNXGNYWBH-YZNIXAGQSA-N [(1S,2S)-2-[2-[[3-(1H-benzimidazol-2-yl)-3-methylbutyl]-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-methylcarbamate Chemical compound CNC(O[C@]1([C@H](C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCC(C)(C)C1=NC2=C(N1)C=CC=C2)=O LXQJMLNXGNYWBH-YZNIXAGQSA-N 0.000 claims 1
- LRGPLTNKGUXPEO-ZQAZVOLISA-N [(1S,2S)-2-[2-[[3-(1H-benzimidazol-2-yl)-3-methylbutyl]-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] morpholine-4-carboxylate Chemical compound N1(CCOCC1)C(=O)O[C@]1([C@H](C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCC(C)(C)C1=NC2=C(N1)C=CC=C2 LRGPLTNKGUXPEO-ZQAZVOLISA-N 0.000 claims 1
- UQEWPONYQOCCOI-NHZFLZHXSA-N [(1S,2S)-2-[2-[[4-(2-amino-3,6-dimethylanilino)-4-oxobutyl]-ethylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] morpholine-4-carboxylate Chemical compound CCN(CCCC(=O)NC1=C(N)C(C)=CC=C1C)CC[C@]1(CCC2=C(C=CC(F)=C2)[C@@H]1C(C)C)OC(=O)N1CCOCC1 UQEWPONYQOCCOI-NHZFLZHXSA-N 0.000 claims 1
- VTCZTGXVSPLLLC-BDYUSTAISA-N [(3R,4S)-3-[2-[3-(1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-7-fluoro-4-propan-2-yl-2,4-dihydrochromen-3-yl] N-methylcarbamate Chemical compound CNC(O[C@]1(COC2=CC(=CC=C2[C@@H]1C(C)C)F)CCN(C)CCCC1=NC2=C(N1)C=CC=C2)=O VTCZTGXVSPLLLC-BDYUSTAISA-N 0.000 claims 1
- FBIMVMYXHNLFCQ-SVEHJYQDSA-N [(3R,4S)-3-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-7-fluoro-4-propan-2-yl-2,4-dihydrochromen-3-yl] N-methylcarbamate Chemical compound CNC(=O)O[C@@]1(CCN(C)CCCC2=NC3=C(C)C=CC(C)=C3N2)COC2=CC(F)=CC=C2[C@@H]1C(C)C FBIMVMYXHNLFCQ-SVEHJYQDSA-N 0.000 claims 1
- VTCZTGXVSPLLLC-AHKZPQOWSA-N [(3S,4S)-3-[2-[3-(1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-7-fluoro-4-propan-2-yl-2,4-dihydrochromen-3-yl] N-methylcarbamate Chemical compound CNC(O[C@@]1(COC2=CC(=CC=C2[C@@H]1C(C)C)F)CCN(C)CCCC1=NC2=C(N1)C=CC=C2)=O VTCZTGXVSPLLLC-AHKZPQOWSA-N 0.000 claims 1
- FBIMVMYXHNLFCQ-ABYGYWHVSA-N [(3S,4S)-3-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-7-fluoro-4-propan-2-yl-2,4-dihydrochromen-3-yl] N-methylcarbamate Chemical compound CNC(O[C@@]1(COC2=CC(=CC=C2[C@@H]1C(C)C)F)CCN(C)CCCC1=NC2=C(N1)C(=CC=C2C)C)=O FBIMVMYXHNLFCQ-ABYGYWHVSA-N 0.000 claims 1
- HBMQEVIYJYANIK-UHFFFAOYSA-N [2-[2-[2-[1-(1H-benzimidazol-2-yl)cyclopropyl]ethyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] morpholine-4-carboxylate Chemical compound N1(CCOCC1)C(=O)OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCC1(CC1)C1=NC2=C(N1)C=CC=C2 HBMQEVIYJYANIK-UHFFFAOYSA-N 0.000 claims 1
- XTXUUZVLJSRTMQ-UHFFFAOYSA-N [2-[2-[3-(4,7-dimethoxy-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-(2-methoxyethyl)carbamate Chemical compound COCCNC(OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCCC1=NC2=C(N1)C(=CC=C2OC)OC)=O XTXUUZVLJSRTMQ-UHFFFAOYSA-N 0.000 claims 1
- SFIKITTVBPYPRG-UHFFFAOYSA-N [2-[2-[3-(4,7-dimethoxy-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-methylcarbamate Chemical compound CNC(=O)OC1(CCN(C)CCCc2nc3c(OC)ccc(OC)c3[nH]2)CCc2cc(F)ccc2C1C(C)C SFIKITTVBPYPRG-UHFFFAOYSA-N 0.000 claims 1
- SSNFLHSDRULAEG-UHFFFAOYSA-N [2-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N,N-dimethylcarbamate Chemical compound CN(C(OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCCC1=NC2=C(N1)C(=CC=C2C)C)=O)C SSNFLHSDRULAEG-UHFFFAOYSA-N 0.000 claims 1
- AKLBSIJIPULMNR-UHFFFAOYSA-N [2-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-[2-(dimethylamino)ethyl]carbamate Chemical compound CN(CCNC(OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCCC1=NC2=C(N1)C(=CC=C2C)C)=O)C AKLBSIJIPULMNR-UHFFFAOYSA-N 0.000 claims 1
- XSOCXUJWAGDABV-UHFFFAOYSA-N [2-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-methylcarbamate Chemical compound CNC(OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCCC1=NC2=C(N1)C(=CC=C2C)C)=O XSOCXUJWAGDABV-UHFFFAOYSA-N 0.000 claims 1
- HNRWFXOJXHBBEU-UHFFFAOYSA-N [2-[2-[3-(4,7-dimethyl-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] morpholine-4-carboxylate Chemical compound N1(CCOCC1)C(=O)OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCCC1=NC2=C(N1)C(=CC=C2C)C HNRWFXOJXHBBEU-UHFFFAOYSA-N 0.000 claims 1
- CLXHMYPWWWNRKP-UHFFFAOYSA-N [2-[2-[3-(4-chloro-7-methoxy-1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N,N-dimethylcarbamate Chemical compound CN(C(OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCCC1=NC2=C(N1)C(=CC=C2OC)Cl)=O)C CLXHMYPWWWNRKP-UHFFFAOYSA-N 0.000 claims 1
- QOYMIFRPTIARMA-UHFFFAOYSA-N [2-[2-[3-[4,6-bis(trifluoromethyl)-1H-benzimidazol-2-yl]propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] morpholine-4-carboxylate Chemical compound N1(CCOCC1)C(=O)OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCCC1=NC2=C(N1)C=C(C=C2C(F)(F)F)C(F)(F)F QOYMIFRPTIARMA-UHFFFAOYSA-N 0.000 claims 1
- RHOFXBMPZHVIIS-UHFFFAOYSA-N [2-[2-[[3-(1H-benzimidazol-2-yl)-3-methylbutyl]-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-(2-methoxyethyl)carbamate Chemical compound COCCNC(OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCC(C)(C)C1=NC2=C(N1)C=CC=C2)=O RHOFXBMPZHVIIS-UHFFFAOYSA-N 0.000 claims 1
- ZXHLFQRZLVJYFT-UHFFFAOYSA-N [2-[2-[[3-(1H-benzimidazol-2-yl)-3-methylbutyl]-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-(2-pyrrolidin-1-ylethyl)carbamate Chemical compound N1(CCCC1)CCNC(OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCC(C)(C)C1=NC2=C(N1)C=CC=C2)=O ZXHLFQRZLVJYFT-UHFFFAOYSA-N 0.000 claims 1
- ZQUBTQKGCHNSGI-UHFFFAOYSA-N [2-[2-[[3-(1H-benzimidazol-2-yl)-3-methylbutyl]-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] N-[2-(diethylamino)ethyl]carbamate Chemical compound C(C)N(CCNC(OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCC(C)(C)C1=NC2=C(N1)C=CC=C2)=O)CC ZQUBTQKGCHNSGI-UHFFFAOYSA-N 0.000 claims 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229960001147 triclofos Drugs 0.000 description 1
- BXDAOUXDMHXPDI-UHFFFAOYSA-N trifluoperazine hydrochloride Chemical compound [H+].[H+].[Cl-].[Cl-].C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 BXDAOUXDMHXPDI-UHFFFAOYSA-N 0.000 description 1
- 229960000315 trifluoperazine hydrochloride Drugs 0.000 description 1
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- 208000022679 triple-negative breast carcinoma Diseases 0.000 description 1
- 229940086984 trisenox Drugs 0.000 description 1
- 201000007423 tubular adenocarcinoma Diseases 0.000 description 1
- 208000022271 tubular adenoma Diseases 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- DTMPGSXFUXZBDK-UHFFFAOYSA-N uldazepam Chemical compound C12=CC(Cl)=CC=C2N=C(NOCC=C)CN=C1C1=CC=CC=C1Cl DTMPGSXFUXZBDK-UHFFFAOYSA-N 0.000 description 1
- 229950004526 uldazepam Drugs 0.000 description 1
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- 201000005112 urinary bladder cancer Diseases 0.000 description 1
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- 125000005500 uronium group Chemical group 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
- 229940102566 valproate Drugs 0.000 description 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
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- PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 description 1
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- 239000011709 vitamin E Substances 0.000 description 1
- 229960000237 vorinostat Drugs 0.000 description 1
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762459355P | 2017-02-15 | 2017-02-15 | |
| US62/459,355 | 2017-02-15 | ||
| PCT/US2018/018356 WO2018152317A1 (en) | 2017-02-15 | 2018-02-15 | Calcium channel inhibitors |
Publications (1)
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|---|---|
| CA3053781A1 true CA3053781A1 (en) | 2018-08-23 |
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Family Applications (1)
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|---|---|---|---|
| CA3053781A Pending CA3053781A1 (en) | 2017-02-15 | 2018-02-15 | Benzopyran and naphalene derivatives and their uses as calium channel inhibitors |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11130750B2 (enExample) |
| EP (1) | EP3585376A4 (enExample) |
| JP (1) | JP7134178B2 (enExample) |
| KR (1) | KR102642063B1 (enExample) |
| CN (1) | CN110545806A (enExample) |
| AU (1) | AU2018221722B2 (enExample) |
| CA (1) | CA3053781A1 (enExample) |
| WO (1) | WO2018152317A1 (enExample) |
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| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12186296B1 (en) | 2016-07-22 | 2025-01-07 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| UY37341A (es) | 2016-07-22 | 2017-11-30 | Flamel Ireland Ltd | Formulaciones de gamma-hidroxibutirato de liberación modificada con farmacocinética mejorada |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11504347B1 (en) | 2016-07-22 | 2022-11-22 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| AU2020231916B2 (en) | 2019-03-01 | 2025-08-28 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
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-
2018
- 2018-02-15 CA CA3053781A patent/CA3053781A1/en active Pending
- 2018-02-15 KR KR1020197027037A patent/KR102642063B1/ko active Active
- 2018-02-15 US US16/486,399 patent/US11130750B2/en active Active
- 2018-02-15 JP JP2019543998A patent/JP7134178B2/ja active Active
- 2018-02-15 CN CN201880024040.6A patent/CN110545806A/zh active Pending
- 2018-02-15 WO PCT/US2018/018356 patent/WO2018152317A1/en not_active Ceased
- 2018-02-15 EP EP18755079.3A patent/EP3585376A4/en active Pending
- 2018-02-15 AU AU2018221722A patent/AU2018221722B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN110545806A (zh) | 2019-12-06 |
| EP3585376A4 (en) | 2020-11-25 |
| AU2018221722B2 (en) | 2022-02-03 |
| US11130750B2 (en) | 2021-09-28 |
| AU2018221722A1 (en) | 2019-10-03 |
| JP2020507606A (ja) | 2020-03-12 |
| KR102642063B1 (ko) | 2024-03-04 |
| US20200385367A1 (en) | 2020-12-10 |
| KR20190130573A (ko) | 2019-11-22 |
| EP3585376A1 (en) | 2020-01-01 |
| WO2018152317A1 (en) | 2018-08-23 |
| JP7134178B2 (ja) | 2022-09-09 |
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