CA2176127A1 - Procedes permettant de traiter ou de prevenir les pathologies associees aux peptides amylo?dogenes - Google Patents
Procedes permettant de traiter ou de prevenir les pathologies associees aux peptides amylo?dogenesInfo
- Publication number
- CA2176127A1 CA2176127A1 CA002176127A CA2176127A CA2176127A1 CA 2176127 A1 CA2176127 A1 CA 2176127A1 CA 002176127 A CA002176127 A CA 002176127A CA 2176127 A CA2176127 A CA 2176127A CA 2176127 A1 CA2176127 A1 CA 2176127A1
- Authority
- CA
- Canada
- Prior art keywords
- ethoxy
- benzoyl
- phenyl
- benzo
- methoxyphenyl
- 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.)
- Abandoned
Links
- 230000003942 amyloidogenic effect Effects 0.000 title claims abstract description 22
- 108010048112 Amyloidogenic Proteins Proteins 0.000 title claims abstract description 21
- 102000009091 Amyloidogenic Proteins Human genes 0.000 title claims abstract description 21
- 238000011282 treatment Methods 0.000 title claims abstract description 14
- 230000002265 prevention Effects 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title abstract description 47
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 60
- -1 dihydronaphthalenes Chemical class 0.000 claims abstract description 34
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 10
- 208000035475 disorder Diseases 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 8
- 201000010374 Down Syndrome Diseases 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 194
- 239000000203 mixture Substances 0.000 claims description 132
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 238000002360 preparation method Methods 0.000 claims description 55
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 42
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 40
- 125000005605 benzo group Chemical group 0.000 claims description 38
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000003870 2-(1-piperidinyl)ethoxy group Chemical group [*]OC([H])([H])C([H])([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 239000001257 hydrogen Chemical group 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 238000009472 formulation Methods 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- VVTOZHSGDQNHDR-UHFFFAOYSA-N [2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 VVTOZHSGDQNHDR-UHFFFAOYSA-N 0.000 claims description 4
- PEJPCPSPGMHTQW-UHFFFAOYSA-N [6-butylsulfonyl-2-(4-butylsulfonylphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(S(=O)(=O)CCCC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(S(=O)(=O)CCCC)C=C2S1 PEJPCPSPGMHTQW-UHFFFAOYSA-N 0.000 claims description 4
- JCDOLTDJNBOLLR-UHFFFAOYSA-N [6-methoxy-2-(4-methoxyphenyl)-1-benzofuran-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(OC)C=C2O1 JCDOLTDJNBOLLR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- BUTBEWXLQVDMBT-UHFFFAOYSA-N [6-pentylsulfonyl-2-(4-pentylsulfonylphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(S(=O)(=O)CCCCC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(S(=O)(=O)CCCCC)C=C2S1 BUTBEWXLQVDMBT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- RDFQQLFSBGBRFL-UHFFFAOYSA-N [1-ethyl-6-methoxy-2-(4-methoxyphenyl)indol-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C12=CC=C(OC)C=C2N(CC)C(C=2C=CC(OC)=CC=2)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 RDFQQLFSBGBRFL-UHFFFAOYSA-N 0.000 claims description 2
- ROHAVRDFSZPOLD-UHFFFAOYSA-N [2-(4-butylsulfonylphenyl)-6-hydroxy-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(S(=O)(=O)CCCC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 ROHAVRDFSZPOLD-UHFFFAOYSA-N 0.000 claims description 2
- LIRXDTIOUUGHAD-UHFFFAOYSA-N [2-(4-chlorophenyl)-1-oxo-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(Cl)=CC=C1C(S(C1=CC=CC=C11)=O)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 LIRXDTIOUUGHAD-UHFFFAOYSA-N 0.000 claims description 2
- ZWLCVOFWYYZDLF-UHFFFAOYSA-N [2-(4-hydroxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 ZWLCVOFWYYZDLF-UHFFFAOYSA-N 0.000 claims description 2
- OQUWGQXCYVDBCY-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[6-methoxy-2-(4-methoxyphenyl)-1-benzofuran-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN(C)C)=CC=2)C2=CC=C(OC)C=C2O1 OQUWGQXCYVDBCY-UHFFFAOYSA-N 0.000 claims description 2
- UGXIVUAIHKSJPN-UHFFFAOYSA-N [6-butylsulfonyl-2-(4-butylsulfonylphenyl)-1-benzothiophen-3-yl]-[4-(3-piperidin-1-ylpropoxy)phenyl]methanone Chemical compound C1=CC(S(=O)(=O)CCCC)=CC=C1C1=C(C(=O)C=2C=CC(OCCCN3CCCCC3)=CC=2)C2=CC=C(S(=O)(=O)CCCC)C=C2S1 UGXIVUAIHKSJPN-UHFFFAOYSA-N 0.000 claims description 2
- RGYQIOOSBFCBCU-UHFFFAOYSA-N [6-butylsulfonyl-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=C(O)C=CC=1C=1SC2=CC(S(=O)(=O)CCCC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 RGYQIOOSBFCBCU-UHFFFAOYSA-N 0.000 claims description 2
- KLDDBCNMLWXGSD-UHFFFAOYSA-N [6-hydroxy-2-(4-hydroxyphenyl)-1-benzofuran-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2O1 KLDDBCNMLWXGSD-UHFFFAOYSA-N 0.000 claims description 2
- HEXLJTVUDDKDOS-UHFFFAOYSA-N [6-methoxy-2-(4-methoxyphenyl)-1-benzofuran-3-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(OC)C=C2O1 HEXLJTVUDDKDOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- PXIYAHHRGDULQZ-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[4-[(4-chlorophenyl)carbamoyl]phenyl]-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophene-6-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=C(C2=C(C3=CC=C(C=C3S2)C(=O)NC=2C=CC(Cl)=CC=2)C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C=C1 PXIYAHHRGDULQZ-UHFFFAOYSA-N 0.000 claims description 2
- VRNHFNDTPNOMBL-UHFFFAOYSA-N n-methyl-2-[4-(methylcarbamoyl)phenyl]-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophene-6-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(C(=O)NC)C=C2S1 VRNHFNDTPNOMBL-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- DWQHXHINSNUITH-UHFFFAOYSA-N (6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 DWQHXHINSNUITH-UHFFFAOYSA-N 0.000 claims 1
- UXCMHGFKLPQEIY-UHFFFAOYSA-N 3-[4-(2-piperidin-1-ylethoxy)benzoyl]-n-propan-2-yl-2-[4-(propan-2-ylcarbamoyl)phenyl]-1-benzothiophene-6-carboxamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(C(=O)NC(C)C)C=C2S1 UXCMHGFKLPQEIY-UHFFFAOYSA-N 0.000 claims 1
- DFFQPZGSIJARKY-UHFFFAOYSA-N [1-ethyl-6-hydroxy-2-(4-methoxyphenyl)indol-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C12=CC=C(O)C=C2N(CC)C(C=2C=CC(OC)=CC=2)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 DFFQPZGSIJARKY-UHFFFAOYSA-N 0.000 claims 1
- VMLOZOVWOJFVFI-UHFFFAOYSA-N [2-(4-chlorophenyl)-1-oxo-1-benzothiophen-3-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(Cl)=CC=C1C(S(C1=CC=CC=C11)=O)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 VMLOZOVWOJFVFI-UHFFFAOYSA-N 0.000 claims 1
- UAUVDTRIPPZZCC-UHFFFAOYSA-N [2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=CC=C2S1 UAUVDTRIPPZZCC-UHFFFAOYSA-N 0.000 claims 1
- SEZLKRUKAYSYCE-UHFFFAOYSA-N [2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=CC=C2S1 SEZLKRUKAYSYCE-UHFFFAOYSA-N 0.000 claims 1
- DTOKARZKAYFVFE-UHFFFAOYSA-N [2-(4-methoxyphenyl)-1-benzothiophen-3-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=CC=C2S1 DTOKARZKAYFVFE-UHFFFAOYSA-N 0.000 claims 1
- RXTALSIUEQVTBJ-UHFFFAOYSA-N [2-(4-methoxyphenyl)-1-benzothiophen-3-yl]-[4-(3-piperidin-1-ylpropoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C=2C=CC(OCCCN3CCCCC3)=CC=2)C2=CC=CC=C2S1 RXTALSIUEQVTBJ-UHFFFAOYSA-N 0.000 claims 1
- CTCDPDLDXQMVHI-UHFFFAOYSA-N [4-[2-(diethylamino)ethoxy]phenyl]-[2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(=O)C1=C(C=2C=CC(O)=CC=2)SC2=CC=CC=C12 CTCDPDLDXQMVHI-UHFFFAOYSA-N 0.000 claims 1
- VPNDIBNQEWHOOO-UHFFFAOYSA-N [4-[2-(diethylamino)ethoxy]phenyl]-[2-(4-methoxyphenyl)-1-benzothiophen-3-yl]methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(=O)C1=C(C=2C=CC(OC)=CC=2)SC2=CC=CC=C12 VPNDIBNQEWHOOO-UHFFFAOYSA-N 0.000 claims 1
- DDKPDPUZGNMJQR-UHFFFAOYSA-N [4-[2-(diethylamino)ethoxy]phenyl]-[2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(=O)C1=C(C=2C=CC(OC)=CC=2)CCC2=CC=CC=C12 DDKPDPUZGNMJQR-UHFFFAOYSA-N 0.000 claims 1
- NUGMASFBOWUCCG-UHFFFAOYSA-N [4-[2-(diethylamino)ethoxy]phenyl]-[6-hydroxy-2-(4-hydroxyphenyl)-1-benzofuran-3-yl]methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(=O)C1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC=C12 NUGMASFBOWUCCG-UHFFFAOYSA-N 0.000 claims 1
- QTWMDADOCIWMCJ-UHFFFAOYSA-N [4-[2-(diethylamino)ethoxy]phenyl]-[6-methoxy-2-(4-methoxyphenyl)-1-benzofuran-3-yl]methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(=O)C1=C(C=2C=CC(OC)=CC=2)OC2=CC(OC)=CC=C12 QTWMDADOCIWMCJ-UHFFFAOYSA-N 0.000 claims 1
- LZRVYDUXPBPSJL-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1C(=O)C1=C(C=2C=CC(O)=CC=2)SC2=CC=CC=C12 LZRVYDUXPBPSJL-UHFFFAOYSA-N 0.000 claims 1
- SDHGXWSAXQECTD-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[2-(4-methoxyphenyl)-1-benzothiophen-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN(C)C)=CC=2)C2=CC=CC=C2S1 SDHGXWSAXQECTD-UHFFFAOYSA-N 0.000 claims 1
- MBYVDLPFKVKFSH-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C1=CC=C(OCCN(C)C)C=C1 MBYVDLPFKVKFSH-UHFFFAOYSA-N 0.000 claims 1
- WKLPUFDPOWRQHW-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[6-hydroxy-2-(4-hydroxyphenyl)-1-benzofuran-3-yl]methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1C(=O)C1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC=C12 WKLPUFDPOWRQHW-UHFFFAOYSA-N 0.000 claims 1
- KRHFIZQFYADCRO-UHFFFAOYSA-N [4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-[2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]methanone Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1C(=O)C1=C(C=2C=CC(O)=CC=2)SC2=CC=CC=C12 KRHFIZQFYADCRO-UHFFFAOYSA-N 0.000 claims 1
- WDIONCKZCVBMKG-UHFFFAOYSA-N [4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-[2-(4-methoxyphenyl)-1-benzothiophen-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN(C(C)C)C(C)C)=CC=2)C2=CC=CC=C2S1 WDIONCKZCVBMKG-UHFFFAOYSA-N 0.000 claims 1
- XHDXDYFMIWMSNC-UHFFFAOYSA-N [4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-[2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C1=CC=C(OCCN(C(C)C)C(C)C)C=C1 XHDXDYFMIWMSNC-UHFFFAOYSA-N 0.000 claims 1
- KXZSAUJSSPFLEK-UHFFFAOYSA-N [4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-[6-hydroxy-2-(4-hydroxyphenyl)-1-benzofuran-3-yl]methanone Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1C(=O)C1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC=C12 KXZSAUJSSPFLEK-UHFFFAOYSA-N 0.000 claims 1
- PFQKWRCZNBMEQN-UHFFFAOYSA-N [4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-[6-methoxy-2-(4-methoxyphenyl)-1-benzofuran-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN(C(C)C)C(C)C)=CC=2)C2=CC=C(OC)C=C2O1 PFQKWRCZNBMEQN-UHFFFAOYSA-N 0.000 claims 1
- BAZWLFUEIINVTH-UHFFFAOYSA-N [6-butylsulfonyl-2-(4-butylsulfonylphenyl)-1-benzothiophen-3-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(S(=O)(=O)CCCC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(S(=O)(=O)CCCC)C=C2S1 BAZWLFUEIINVTH-UHFFFAOYSA-N 0.000 claims 1
- WDCPJTSXWJFXGJ-UHFFFAOYSA-N [6-hexylsulfonyl-2-(4-hexylsulfonylphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(S(=O)(=O)CCCCCC)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(S(=O)(=O)CCCCCC)C=C2S1 WDCPJTSXWJFXGJ-UHFFFAOYSA-N 0.000 claims 1
- RJPCXHINTJKOPW-UHFFFAOYSA-N [6-hydroxy-2-(4-hydroxyphenyl)-1-benzofuran-3-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(O)C=C2O1 RJPCXHINTJKOPW-UHFFFAOYSA-N 0.000 claims 1
- FMNWSASOWARPII-UHFFFAOYSA-N [6-methoxy-2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC(OC)=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 FMNWSASOWARPII-UHFFFAOYSA-N 0.000 claims 1
- 150000001907 coumarones Chemical class 0.000 abstract description 11
- 150000002790 naphthalenes Chemical class 0.000 abstract description 5
- 206010044688 Trisomy 21 Diseases 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 188
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
- 239000011541 reaction mixture Substances 0.000 description 70
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 64
- 229940093499 ethyl acetate Drugs 0.000 description 62
- 235000019439 ethyl acetate Nutrition 0.000 description 62
- 239000003921 oil Substances 0.000 description 59
- 235000019198 oils Nutrition 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
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- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
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- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
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- CBQVOBIZPAFTDN-UHFFFAOYSA-N phenyl 4-(2-pyrrolidin-1-ylethoxy)benzoate Chemical compound C=1C=C(OCCN2CCCC2)C=CC=1C(=O)OC1=CC=CC=C1 CBQVOBIZPAFTDN-UHFFFAOYSA-N 0.000 description 1
- GJLNWLVPAHNBQN-UHFFFAOYSA-N phenyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OC1=CC=CC=C1 GJLNWLVPAHNBQN-UHFFFAOYSA-N 0.000 description 1
- BNZYBNYNPXKWCM-UHFFFAOYSA-N phenyl 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC1=CC=CC=C1 BNZYBNYNPXKWCM-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- 150000003141 primary amines Chemical group 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 1
- 125000005470 propylenyl group Chemical group 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
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- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 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 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 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
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Procédés permettant de traiter ou de prévenir les dysfonctionemments physiologiques associés à un peptide amyloïdogène, selon lesquels on administre une série d'indoles de benzothiophènes, de benzofurannes, de dihydronaphtalènes, de naphtalènes substitués ou leurs sels ou solvates pharmaceutiquement acceptables. Sont également décrits des procédés permettant de traiter ou de prévenir la maladie d'Alzeimer ou le syndrome de Down, qui consistent à administrer ces mêmes benzofurannes ou benzothiophènes, ou leurs sels pharmaceutiquement acceptables.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17154693A | 1993-12-21 | 1993-12-21 | |
| US08/171,546 | 1993-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2176127A1 true CA2176127A1 (fr) | 1995-06-29 |
Family
ID=22624148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002176127A Abandoned CA2176127A1 (fr) | 1993-12-21 | 1994-12-14 | Procedes permettant de traiter ou de prevenir les pathologies associees aux peptides amylo?dogenes |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0735821A4 (fr) |
| JP (1) | JPH09507071A (fr) |
| AU (1) | AU1440395A (fr) |
| CA (1) | CA2176127A1 (fr) |
| WO (1) | WO1995017095A1 (fr) |
| ZA (1) | ZA9410036B (fr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL115582A0 (en) * | 1994-10-14 | 1996-01-19 | Lilly Co Eli | Methods for treating resistant tumors |
| IL115613A0 (en) * | 1994-10-20 | 1996-01-19 | Lilly Co Eli | Bicyclic neuropeptide y receptor antagonists |
| CA2206752A1 (fr) * | 1996-07-02 | 1998-01-02 | George Joseph Cullinan | Composes de benzothiophene,intermediaires, procedes et methodes d'utilisation |
| US5965614A (en) | 1996-11-22 | 1999-10-12 | Athena Neurosciences, Inc. | N-(aryl/heteroaryl) amino acid esters, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds |
| WO1998022441A2 (fr) * | 1996-11-22 | 1998-05-28 | Elan Pharmaceuticals, Inc. | ESTERS DE N-(ARYL/HETEROARYL) AMINOACIDE, COMPOSITIONS PHARMACEUTIQUES ET METHODES POUR INHIBER LA LIBERATION DU PEPTIDE β-AMYLOIDE ET/OU SA SYNTHESE |
| US6117911A (en) | 1997-04-11 | 2000-09-12 | Neorx Corporation | Compounds and therapies for the prevention of vascular and non-vascular pathologies |
| WO1998048794A1 (fr) | 1997-04-30 | 1998-11-05 | Eli Lilly And Company | Agents antithrombotiques |
| WO1998048804A1 (fr) | 1997-04-30 | 1998-11-05 | Eli Lilly And Company | Agents antithrombotiques |
| WO1998049161A1 (fr) | 1997-04-30 | 1998-11-05 | Eli Lilly And Company | Agents antithrombotiques |
| ATE268768T1 (de) | 1997-04-30 | 2004-06-15 | Lilly Co Eli | Antithrombosemittel |
| CA2291026A1 (fr) | 1997-06-05 | 1998-12-10 | Takeda Chemical Industries, Ltd. | Composes heterocycliques, leur preparation et leur utilisation |
| US5994396A (en) * | 1997-08-18 | 1999-11-30 | Centaur Pharmaceuticals, Inc. | Furansulfonic acid derivatives and pharmaceutical compositions containing the same |
| AU3171099A (en) * | 1998-04-17 | 1999-11-08 | Senga Pharmaceutical Laboratory Inc. | 1-heteroindene derivatives and medicinal composition containing the same |
| US6284756B1 (en) | 1998-04-30 | 2001-09-04 | Eli Lilly And Company | Antithrombotic agents |
| US6288108B1 (en) | 1998-06-16 | 2001-09-11 | Eli Lilly And Company | Methods for increasing levels of acetylcholine |
| WO1999065309A1 (fr) * | 1998-06-16 | 1999-12-23 | Eli Lilly And Company | Procede d'augmentation des taux d'acetylcholine |
| KR20010052891A (ko) | 1998-06-16 | 2001-06-25 | 피터 지. 스트링거 | 아세틸콜린 수치를 상승시키는 방법 |
| DK0997460T3 (da) * | 1998-10-28 | 2003-03-31 | Lilly Co Eli | Benzothiophenforbindelser som antithrombotiske midler og mellemprodukter |
| US6613083B2 (en) | 2001-05-02 | 2003-09-02 | Eckhard Alt | Stent device and method |
| MXPA05013975A (es) * | 2003-06-23 | 2006-03-09 | Neurochem Int Ltd | Tratamiento de enfermedades asociadas con amiloide y epileptogenesis. |
| TW200736252A (en) | 2006-01-27 | 2007-10-01 | Astrazeneca Ab | Novel heteroaryl substituted benzothiazoles |
| TW200813035A (en) | 2006-06-19 | 2008-03-16 | Astrazeneca Ab | Novel heteroaryl substituted benzoxazoles |
| KR100858357B1 (ko) * | 2006-10-02 | 2008-09-11 | (주) 디지탈바이오텍 | 벤조퓨란계 유도체 화합물을 유효성분으로 함유하는인지기능 장애의 예방 및 치료용 조성물 |
| JP2008231102A (ja) * | 2007-02-23 | 2008-10-02 | Hiroaki Okuno | アミロイドベータ凝集阻害作用を有するフェノール誘導体 |
| TW200901998A (en) * | 2007-03-06 | 2009-01-16 | Astrazeneca Ab | Novel 2-heteroaryl substituted benzothiophenes and benzofuranes |
| US8193363B2 (en) | 2008-08-29 | 2012-06-05 | Astrazeneca Ab | Compounds suitable as precursors to compounds that are useful for imaging amyloid deposits |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024273A (en) * | 1974-06-20 | 1977-05-17 | Smithkline Corporation | Coronary vasodilator and anti-anginal compositions comprising substituted benzofurans and benzothiophenes and methods of producing coronary vasodilation and anti-anginal activity |
| US4133814A (en) * | 1975-10-28 | 1979-01-09 | Eli Lilly And Company | 2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents |
| US4230862A (en) * | 1975-10-28 | 1980-10-28 | Eli Lilly And Company | Antifertility compounds |
| GB8704572D0 (en) * | 1987-02-26 | 1987-04-01 | Lundbeck & Co As H | Organic compounds |
| US5185350A (en) * | 1991-09-23 | 1993-02-09 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted pyridinylamino-1h-indoles,1h-indazoles,2h-indazoles, benzo (b)thiophenes and 1,2-benzisothiazoles |
| US5482949A (en) * | 1993-03-19 | 1996-01-09 | Eli Lilly And Company | Sulfonate derivatives of 3-aroylbenzo[b]thiophenes |
| DE4311870C2 (de) * | 1993-04-10 | 1998-07-30 | Altramed Holdings Ltd | Verwendung eines Anti-Östrigens zur Therapie und Prophylaxe von Demenz-Erkrankungen |
| AU1339795A (en) * | 1993-12-21 | 1995-07-10 | Eli Lilly And Company | Non-peptide tachykinin receptor antagonists |
-
1994
- 1994-12-14 WO PCT/US1994/014655 patent/WO1995017095A1/fr not_active Ceased
- 1994-12-14 AU AU14403/95A patent/AU1440395A/en not_active Abandoned
- 1994-12-14 CA CA002176127A patent/CA2176127A1/fr not_active Abandoned
- 1994-12-14 JP JP7517547A patent/JPH09507071A/ja active Pending
- 1994-12-14 EP EP95906018A patent/EP0735821A4/fr not_active Withdrawn
- 1994-12-15 ZA ZA9410036A patent/ZA9410036B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA9410036B (en) | 1996-06-18 |
| JPH09507071A (ja) | 1997-07-15 |
| AU1440395A (en) | 1995-07-10 |
| EP0735821A4 (fr) | 1998-04-01 |
| WO1995017095A1 (fr) | 1995-06-29 |
| EP0735821A1 (fr) | 1996-10-09 |
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| FZDE | Dead |