CA2309966A1 - Association de principes actifs, notamment de tetrahydropyridines et d'agents inhibiteurs de l'acetylcholinesterase, pour le traitement de la demence senile du type alzheimer - Google Patents
Association de principes actifs, notamment de tetrahydropyridines et d'agents inhibiteurs de l'acetylcholinesterase, pour le traitement de la demence senile du type alzheimer Download PDFInfo
- Publication number
- CA2309966A1 CA2309966A1 CA002309966A CA2309966A CA2309966A1 CA 2309966 A1 CA2309966 A1 CA 2309966A1 CA 002309966 A CA002309966 A CA 002309966A CA 2309966 A CA2309966 A CA 2309966A CA 2309966 A1 CA2309966 A1 CA 2309966A1
- Authority
- CA
- Canada
- Prior art keywords
- tetrahydropyridine
- ethyl
- trifluoromethylphenyl
- biphenylyl
- alkyl
- 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
- 208000024827 Alzheimer disease Diseases 0.000 title claims description 17
- 206010039966 Senile dementia Diseases 0.000 title claims description 13
- 102000012440 Acetylcholinesterase Human genes 0.000 title abstract 2
- 108010022752 Acetylcholinesterase Proteins 0.000 title abstract 2
- 229940022698 acetylcholinesterase Drugs 0.000 title abstract 2
- 230000002401 inhibitory effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- -1 phenoxy, phenylamino Chemical group 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 238000002636 symptomatic treatment Methods 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims abstract description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 125000005504 styryl group Chemical group 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
- 125000005843 halogen group Chemical group 0.000 claims abstract 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 24
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 20
- WJJYZXPHLSLMGE-UHFFFAOYSA-N xaliproden Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C4C=CC=CC4=CC=3)CC=2)=C1 WJJYZXPHLSLMGE-UHFFFAOYSA-N 0.000 claims description 19
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 13
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 10
- 229960003530 donepezil Drugs 0.000 claims description 8
- 229960001685 tacrine Drugs 0.000 claims description 8
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical group C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 4
- CNEWKIDCGDXBDE-UHFFFAOYSA-N 1-[2-(4-phenylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=CC=CC=3)CC=2)=C1 CNEWKIDCGDXBDE-UHFFFAOYSA-N 0.000 claims description 3
- GAPOASFZXBWUGS-UHFFFAOYSA-N 2,2,2-trifluoro-1-(3-trimethylsilylphenyl)ethanone Chemical compound C[Si](C)(C)C1=CC=CC(C(=O)C(F)(F)F)=C1 GAPOASFZXBWUGS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 3
- CLAAWCXSVHYZOF-UHFFFAOYSA-N 1-[2-(2-chloro-4-phenylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C(=CC(=CC=3)C=3C=CC=CC=3)Cl)CC=2)=C1 CLAAWCXSVHYZOF-UHFFFAOYSA-N 0.000 claims description 2
- DRUFLWBKCQQARQ-UHFFFAOYSA-N 1-[2-(2-methoxy-5-phenylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound COC1=CC=C(C=2C=CC=CC=2)C=C1CCN(CC=1)CCC=1C1=CC=CC(C(F)(F)F)=C1 DRUFLWBKCQQARQ-UHFFFAOYSA-N 0.000 claims description 2
- QRXBOJSFBITNAZ-UHFFFAOYSA-N 1-[2-(3,4-dipropylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=C(CCC)C(CCC)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 QRXBOJSFBITNAZ-UHFFFAOYSA-N 0.000 claims description 2
- PYPATGSHJOYCQF-UHFFFAOYSA-N 1-[2-(3-chloro-4-phenylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(Cl)C(=CC=3)C=3C=CC=CC=3)CC=2)=C1 PYPATGSHJOYCQF-UHFFFAOYSA-N 0.000 claims description 2
- IYEVNGCQLBOKSD-UHFFFAOYSA-N 1-[2-(3-fluoro-4-phenylphenyl)propyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C=1C=C(C=2C=CC=CC=2)C(F)=CC=1C(C)CN(CC=1)CCC=1C1=CC=CC(C(F)(F)F)=C1 IYEVNGCQLBOKSD-UHFFFAOYSA-N 0.000 claims description 2
- QQYINFSTLSPFDL-UHFFFAOYSA-N 1-[2-(3-phenylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3C=CC=CC=3)CC=2)=C1 QQYINFSTLSPFDL-UHFFFAOYSA-N 0.000 claims description 2
- RMTTZCBMBRCQRV-UHFFFAOYSA-N 1-[2-(4-benzylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(CC=4C=CC=CC=4)=CC=3)CC=2)=C1 RMTTZCBMBRCQRV-UHFFFAOYSA-N 0.000 claims description 2
- WCLDJGHFRWOPJG-UHFFFAOYSA-N 1-[2-(4-butoxyphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=CC(OCCCC)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 WCLDJGHFRWOPJG-UHFFFAOYSA-N 0.000 claims description 2
- RWPHWFAGKMQMNQ-UHFFFAOYSA-N 1-[2-(4-butylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=CC(CCCC)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 RWPHWFAGKMQMNQ-UHFFFAOYSA-N 0.000 claims description 2
- VALBFTWRAPRFAG-UHFFFAOYSA-N 1-[2-(4-cyclohexylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C3CCCCC3)CC=2)=C1 VALBFTWRAPRFAG-UHFFFAOYSA-N 0.000 claims description 2
- ABBQYZDVGHQSMF-UHFFFAOYSA-N 1-[2-(4-phenoxyphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(OC=4C=CC=CC=4)=CC=3)CC=2)=C1 ABBQYZDVGHQSMF-UHFFFAOYSA-N 0.000 claims description 2
- AKTLNRAASMIFMW-UHFFFAOYSA-N 1-[2-[3,4-bis(2-methylpropyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=C(CC(C)C)C(CC(C)C)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 AKTLNRAASMIFMW-UHFFFAOYSA-N 0.000 claims description 2
- SNFRDRZUPBHGJT-UHFFFAOYSA-N 1-[2-[3-chloro-4-(3-chlorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(Cl)C(=CC=3)C=3C=C(Cl)C=CC=3)CC=2)=C1 SNFRDRZUPBHGJT-UHFFFAOYSA-N 0.000 claims description 2
- CDLNSVYOVRTZMA-UHFFFAOYSA-N 1-[2-[4-(2,4-dichlorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C(=CC(Cl)=CC=3)Cl)CC=2)=C1 CDLNSVYOVRTZMA-UHFFFAOYSA-N 0.000 claims description 2
- PXDPEQSARDZRSU-UHFFFAOYSA-N 1-[2-[4-(2-chlorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C(=CC=CC=3)Cl)CC=2)=C1 PXDPEQSARDZRSU-UHFFFAOYSA-N 0.000 claims description 2
- WSPBZUSIEIUXCY-UHFFFAOYSA-N 1-[2-[4-(3,5-dichlorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=C(Cl)C=C(Cl)C=3)CC=2)=C1 WSPBZUSIEIUXCY-UHFFFAOYSA-N 0.000 claims description 2
- PUPRBDYGCRMPKP-UHFFFAOYSA-N 1-[2-[4-(3-chloro-4-fluorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=C(Cl)C(F)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 PUPRBDYGCRMPKP-UHFFFAOYSA-N 0.000 claims description 2
- ZDSKKYNVKVTUBT-UHFFFAOYSA-N 1-[2-[4-(3-chlorophenyl)phenyl]-2-methylpropyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C=1C=C(C=2C=C(Cl)C=CC=2)C=CC=1C(C)(C)CN(CC=1)CCC=1C1=CC=CC(C(F)(F)F)=C1 ZDSKKYNVKVTUBT-UHFFFAOYSA-N 0.000 claims description 2
- XNACPFPQUNDICM-UHFFFAOYSA-N 1-[2-[4-(3-chlorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=C(Cl)C=CC=3)CC=2)=C1 XNACPFPQUNDICM-UHFFFAOYSA-N 0.000 claims description 2
- WAFSHDHWRRPPSQ-UHFFFAOYSA-N 1-[2-[4-(4-chlorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=CC(Cl)=CC=3)CC=2)=C1 WAFSHDHWRRPPSQ-UHFFFAOYSA-N 0.000 claims description 2
- CPNHRQSEIFVLQO-UHFFFAOYSA-N 1-[2-[4-(4-fluorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=CC(F)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 CPNHRQSEIFVLQO-UHFFFAOYSA-N 0.000 claims description 2
- KRZBYJLACJFLEQ-UHFFFAOYSA-N 1-[2-[4-(4-methoxyphenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 KRZBYJLACJFLEQ-UHFFFAOYSA-N 0.000 claims description 2
- VZTXRLKHUFPMRC-UHFFFAOYSA-N 1-[2-methyl-2-(4-phenylphenyl)propyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(C)(C)CN(CC=1)CCC=1C1=CC=CC(C(F)(F)F)=C1 VZTXRLKHUFPMRC-UHFFFAOYSA-N 0.000 claims description 2
- XQHBVCWPLIENDJ-UHFFFAOYSA-N 2-chloro-6-[1-[2-(4-cyclohexylphenyl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]pyridine Chemical compound ClC1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C3CCCCC3)CC=2)=N1 XQHBVCWPLIENDJ-UHFFFAOYSA-N 0.000 claims description 2
- WALYRZRLDDOTJG-UHFFFAOYSA-N 2-chloro-6-[1-[2-(4-phenylphenyl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]pyridine Chemical compound ClC1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=CC=CC=3)CC=2)=N1 WALYRZRLDDOTJG-UHFFFAOYSA-N 0.000 claims description 2
- GKZWPTSMKCVFMZ-UHFFFAOYSA-N 2-chloro-6-[1-[2-[4-(2-methylpropyl)phenyl]propyl]-3,6-dihydro-2h-pyridin-4-yl]pyridine Chemical compound C1=CC(CC(C)C)=CC=C1C(C)CN1CC=C(C=2N=C(Cl)C=CC=2)CC1 GKZWPTSMKCVFMZ-UHFFFAOYSA-N 0.000 claims description 2
- HPOIPOPJGBKXIR-UHFFFAOYSA-N 3,6-dimethoxy-10-methyl-galantham-1-ene Natural products O1C(C(=CC=2)OC)=C3C=2CN(C)CCC23C1CC(OC)C=C2 HPOIPOPJGBKXIR-UHFFFAOYSA-N 0.000 claims description 2
- NVJCKHLCZVJYHR-UHFFFAOYSA-N 4-(4-fluorophenyl)-1-[2-(4-phenylphenyl)ethyl]-3,6-dihydro-2h-pyridine Chemical compound C1=CC(F)=CC=C1C(CC1)=CCN1CCC1=CC=C(C=2C=CC=CC=2)C=C1 NVJCKHLCZVJYHR-UHFFFAOYSA-N 0.000 claims description 2
- ZWLXREOJYZDTTE-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]-1-[2-[4-[2-(trifluoromethyl)phenyl]phenyl]ethyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C(=CC=CC=3)C(F)(F)F)CC=2)=C1 ZWLXREOJYZDTTE-UHFFFAOYSA-N 0.000 claims description 2
- JJZHILQQKTVDMU-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]-1-[2-[4-[3-(trifluoromethyl)phenyl]phenyl]ethyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=C(C=CC=3)C(F)(F)F)CC=2)=C1 JJZHILQQKTVDMU-UHFFFAOYSA-N 0.000 claims description 2
- RRTUHDMSMMCWNI-UHFFFAOYSA-N 4-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 RRTUHDMSMMCWNI-UHFFFAOYSA-N 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
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Classifications
-
- 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
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
-
- 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
-
- 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
- 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
- A61P25/28—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
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
L'invention concerne une composition pharmaceutique contenant en tant que principes actifs un composant (a) choisi entre la 1-(2-napht-2-yléthyl)-4-(3-trifluorométhylphenyl)-1,2,3,6-tétrahydropyridine et un composé (I) dans laquelle Y représente -CH- ou -N-; R¿1? représente l'hydrogène, un halogène, un groupe CF¿3?, (C¿3?-C¿4?)alkyle ou (C¿1?-C¿4?)alcoxyle; R¿2? représente l'hydrogène, un halogène, un hydroxyle, un groupe CF¿3?, (C¿3?-C¿4?)alkyle ou (C¿1?-C¿4?)alkoxyle; R¿3? et R¿4? représentent chacun l'hydrogène ou un (C¿1?-C¿3?)alkyle; X représente (a) un (C¿3?-C¿6?)alkyle; un (C¿3?-C¿6?)alkoxyle; un (C¿3?-C¿7?)carboxyalkyle; un (C¿1?-C¿4?)alkoxycarbonyl(C¿3?-C¿6?)alkyle; un (C¿3?-C¿7?)carboxyalkoxyle; ou un (C¿1?-C¿4?)alkoxycarbonyl(C¿3?-C¿6?)alkoxyle; (b) un radic al choisi parmi un (C¿3?-C¿7?)cycloalkyle, (C¿3?-C¿7?)cycloalkyloxy, (C¿3?-C¿7?)cycloalkylméthyle, (C¿3?-C¿7?)cycloalkylamino et cyclohexényle, ledit radical pouvant être substitué par un halogène, hydroxy, (C¿1?-C¿4?)alcoxy, carboxy, (C¿1?-C¿4?)alkoxycarbonyle, amino, mono- ou di-(C¿1?-C¿4?)alkyamino; ou (c) un groupe choisi parmi phényle, phénoxy, phénylamino, N-(C¿1?-C¿3?)alkyl-phényl-amino, phénylméthyl, phényléthyle, phénylcarbonyle, phénylthio, phénylsulphonyle, phénylsulphinyle et styryle, ledit groupe pouvant être mono- ou polysubstitué sur le groupe phényle par un halogène, CF¿3?, (C¿1?-C¿4?)alkyle, (C¿1?-C¿4?)alkoxy, cyano, amino, mono- ou di-(C¿1?-C¿4?)alkylamino, (C¿1?-C¿4?)acylamino, carboxy, (C¿1?-C¿4?)alkoxycarbonyle, aminocarbonyle, mono- ou di-(C¿1?-C¿4?)alkylaminocarbonyle, amino(C¿1?-C¿4?)alkyle, hydroxy(C¿1?-C¿4?)alkyle ou halogéno(C¿1?-C¿4?)alkyle; éventuellement sous la forme de l'un de ses sels pharmaceutiquement acceptables, et un composant (b) actif dans le traitement symptomatique de la DAT, éventuellement sous la forme de l'un de ses sels pharmaceutiquement acceptables, à la condition que lorsque le composant (a) est autre que la 1-(2-napht-2-yléthyl)-4-(3-trifluorométhylphényl)-1,2,3,6-tétrahydropyridine ou l'un de ses sels pharmaceutiquement acceptables, le composant (b) est un agent inhibiteur de l'acétylcholinestérase.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR97/14324 | 1997-11-14 | ||
| FR9714324A FR2771006B1 (fr) | 1997-11-14 | 1997-11-14 | Association de principes actifs pour le traitement de la demence senile du type alzheimer |
| FR97/14322 | 1997-11-14 | ||
| FR9714322A FR2771007B1 (fr) | 1997-11-14 | 1997-11-14 | Association de principes actifs pour le traitement de la demence senile du type alzheimer |
| PCT/FR1998/002384 WO1999025363A1 (fr) | 1997-11-14 | 1998-11-09 | Association de principes actifs, notamment de tetrahydropyridines et d'agents inhibiteurs de l'acetylcholinesterase, pour le traitement de la demence senile du type alzheimer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2309966A1 true CA2309966A1 (fr) | 1999-05-27 |
Family
ID=26233932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002309966A Abandoned CA2309966A1 (fr) | 1997-11-14 | 1998-11-09 | Association de principes actifs, notamment de tetrahydropyridines et d'agents inhibiteurs de l'acetylcholinesterase, pour le traitement de la demence senile du type alzheimer |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP1030671A1 (fr) |
| JP (1) | JP2001523642A (fr) |
| KR (1) | KR100599350B1 (fr) |
| CN (1) | CN1243540C (fr) |
| AU (1) | AU743228B2 (fr) |
| BG (1) | BG64819B1 (fr) |
| BR (1) | BR9814035A (fr) |
| CA (1) | CA2309966A1 (fr) |
| CO (1) | CO4980891A1 (fr) |
| DZ (1) | DZ2649A1 (fr) |
| EA (1) | EA003255B1 (fr) |
| EE (1) | EE04235B1 (fr) |
| HU (1) | HUP0100098A3 (fr) |
| ID (1) | ID24933A (fr) |
| IL (2) | IL136122A0 (fr) |
| IS (1) | IS5482A (fr) |
| MY (1) | MY120461A (fr) |
| NO (1) | NO20002450L (fr) |
| NZ (1) | NZ504420A (fr) |
| OA (1) | OA11464A (fr) |
| PL (1) | PL194597B1 (fr) |
| SA (1) | SA98190747B1 (fr) |
| SK (1) | SK286040B6 (fr) |
| TR (1) | TR200001262T2 (fr) |
| TW (1) | TW585766B (fr) |
| UY (1) | UY25247A1 (fr) |
| WO (1) | WO1999025363A1 (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003105830A1 (fr) * | 2002-06-14 | 2003-12-24 | 富山化学工業株式会社 | Compositions medicinales ameliorant le fonctionnement du cerveau, et procede pour ameliorer le fonctionnement du cerveau |
| US20060160079A1 (en) * | 2002-08-07 | 2006-07-20 | Lane Roger M | Methods for the treatment of dementia based on apo e genotype |
| CN1520818A (zh) * | 2003-02-09 | 2004-08-18 | ɽ����Ҷ��Ȼҩ���о���������˾ | 治疗老年性痴呆的胆碱酯酶抑制剂药物组合物 |
| US8481565B2 (en) | 2004-12-27 | 2013-07-09 | Eisai R&D Management Co., Ltd. | Method for stabilizing anti-dementia drug |
| AU2015210852B2 (en) | 2014-01-31 | 2019-01-24 | Cognition Therapeutics, Inc. | Isoindoline compositions and methods for treating neurodegenerative disease |
| DK3634394T3 (da) | 2017-05-15 | 2026-03-02 | Cognition Therapeutics Inc | Sammensætninger til behandling af neurogenerative sygdomme |
| KR102224917B1 (ko) | 2018-03-20 | 2021-03-09 | (주)인벤티지랩 | 인지 장애 관련 질병의 예방 또는 치료용 약학적 조성물의 제조 방법 및 이의 제조 방법으로 제조된 인지 장애 관련 질병의 예방 또는 치료용 약학적 조성물 |
| WO2019182319A1 (fr) * | 2018-03-20 | 2019-09-26 | (주)인벤티지랩 | Procédé de préparation de composition pharmaceutique de prévention ou de traitement de maladies associées au trouble cognitif, et composition pharmaceutique de prévention ou de traitement de maladies associées au trouble cognitif, préparée par le procédé de préparation |
| CN109265391B (zh) * | 2018-11-13 | 2021-11-19 | 枣庄学院 | 联苯多取代1,2,5,6-四氢吡啶化合物及其合成方法与应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2662355B1 (fr) * | 1990-05-22 | 1994-11-10 | Sanofi Sa | Utilisation de la 1-[2-(2-naphtyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine pour la preparation de medicaments destines au traitement de troubles cerebraux et neuronaux. |
| US5453428A (en) * | 1991-02-14 | 1995-09-26 | The Mount Sinai School Of Medicine Of The City Of New York | Method and composition for the treatment of apathy-amotivation syndrome |
| CA2213000A1 (fr) * | 1995-03-06 | 1996-09-12 | Interneuron Pharmaceuticals, Inc. | Reduction de l'ampleur des infarctus par la citicoline |
| FR2736053B1 (fr) * | 1995-06-28 | 1997-09-19 | Sanofi Sa | Nouvelles 1-phenylalkyl-1,2,3,6-tetrahydropyridines |
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1998
- 1998-10-26 CO CO98062479A patent/CO4980891A1/es unknown
- 1998-10-28 TW TW087117874A patent/TW585766B/zh not_active IP Right Cessation
- 1998-11-09 SK SK711-2000A patent/SK286040B6/sk unknown
- 1998-11-09 CN CNB988130947A patent/CN1243540C/zh not_active Expired - Fee Related
- 1998-11-09 JP JP2000520796A patent/JP2001523642A/ja not_active Withdrawn
- 1998-11-09 EA EA200000412A patent/EA003255B1/ru not_active IP Right Cessation
- 1998-11-09 WO PCT/FR1998/002384 patent/WO1999025363A1/fr not_active Ceased
- 1998-11-09 CA CA002309966A patent/CA2309966A1/fr not_active Abandoned
- 1998-11-09 NZ NZ504420A patent/NZ504420A/en unknown
- 1998-11-09 TR TR2000/01262T patent/TR200001262T2/xx unknown
- 1998-11-09 BR BR9814035-3A patent/BR9814035A/pt not_active Application Discontinuation
- 1998-11-09 HU HU0100098A patent/HUP0100098A3/hu unknown
- 1998-11-09 AU AU11609/99A patent/AU743228B2/en not_active Ceased
- 1998-11-09 EP EP98954538A patent/EP1030671A1/fr not_active Withdrawn
- 1998-11-09 KR KR1020007005231A patent/KR100599350B1/ko not_active Expired - Fee Related
- 1998-11-09 ID IDW20000860A patent/ID24933A/id unknown
- 1998-11-09 EE EEP200000290A patent/EE04235B1/xx not_active IP Right Cessation
- 1998-11-09 PL PL98340500A patent/PL194597B1/pl not_active IP Right Cessation
- 1998-11-09 IL IL13612298A patent/IL136122A0/xx not_active IP Right Cessation
- 1998-11-11 DZ DZ980259A patent/DZ2649A1/fr active
- 1998-11-12 UY UY25247A patent/UY25247A1/es not_active IP Right Cessation
- 1998-11-14 MY MYPI98005180A patent/MY120461A/en unknown
- 1998-11-14 SA SA98190747A patent/SA98190747B1/ar unknown
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2000
- 2000-05-09 IS IS5482A patent/IS5482A/is unknown
- 2000-05-11 NO NO20002450A patent/NO20002450L/no unknown
- 2000-05-11 BG BG104428A patent/BG64819B1/bg unknown
- 2000-05-12 OA OA1200000141A patent/OA11464A/en unknown
- 2000-05-14 IL IL136122A patent/IL136122A/en unknown
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