CA2309966A1 - Combination of active principles, in particular of tetrahydropyridins and acetylcholinesterase inhibiting agents, for treating senile dementia such as alzheimer dementia - Google Patents

Combination of active principles, in particular of tetrahydropyridins and acetylcholinesterase inhibiting agents, for treating senile dementia such as alzheimer dementia Download PDF

Info

Publication number: CA2309966A1
Authority: CA; Canada
Prior art keywords: tetrahydropyridine; ethyl; trifluoromethylphenyl; biphenylyl; alkyl
Prior art date: 1997-11-14
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

Application number

CA002309966A

Other languages

English (en)

French (fr)

Inventor

Jean-Pierre Maffrand

Philippe Soubrie

Jean-Paul Terranova

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis France

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1997-11-14

Filing date

1998-11-09

Publication date

1999-05-27

1997-11-14 Priority claimed from FR9714324A external-priority patent/FR2771006B1/fr

1997-11-14 Priority claimed from FR9714322A external-priority patent/FR2771007B1/fr

1998-11-09 Application filed by Individual filed Critical Individual

1999-05-27 Publication of CA2309966A1 publication Critical patent/CA2309966A1/en

Status Abandoned legal-status Critical Current

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
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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)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (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)

CA002309966A 1997-11-14 1998-11-09 Combination of active principles, in particular of tetrahydropyridins and acetylcholinesterase inhibiting agents, for treating senile dementia such as alzheimer dementia Abandoned CA2309966A1 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
FR9714324A FR2771006B1 (fr)	1997-11-14	1997-11-14	Association de principes actifs pour le traitement de la demence senile du type alzheimer
FR9714322A FR2771007B1 (fr)	1997-11-14	1997-11-14	Association de principes actifs pour le traitement de la demence senile du type alzheimer
FR97/14324		1997-11-14
FR97/14322		1997-11-14
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 (en)	1999-05-27

Family

ID=26233932

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002309966A Abandoned CA2309966A1 (en)	1997-11-14	1998-11-09	Combination of active principles, in particular of tetrahydropyridins and acetylcholinesterase inhibiting agents, for treating senile dementia such as alzheimer dementia

Country Status (27)

Country	Link
EP (1)	EP1030671A1 (pl)
JP (1)	JP2001523642A (pl)
KR (1)	KR100599350B1 (pl)
CN (1)	CN1243540C (pl)
AU (1)	AU743228B2 (pl)
BG (1)	BG64819B1 (pl)
BR (1)	BR9814035A (pl)
CA (1)	CA2309966A1 (pl)
CO (1)	CO4980891A1 (pl)
DZ (1)	DZ2649A1 (pl)
EA (1)	EA003255B1 (pl)
EE (1)	EE04235B1 (pl)
HU (1)	HUP0100098A3 (pl)
ID (1)	ID24933A (pl)
IL (2)	IL136122A0 (pl)
IS (1)	IS5482A (pl)
MY (1)	MY120461A (pl)
NO (1)	NO20002450L (pl)
NZ (1)	NZ504420A (pl)
OA (1)	OA11464A (pl)
PL (1)	PL194597B1 (pl)
SA (1)	SA98190747B1 (pl)
SK (1)	SK286040B6 (pl)
TR (1)	TR200001262T2 (pl)
TW (1)	TW585766B (pl)
UY (1)	UY25247A1 (pl)
WO (1)	WO1999025363A1 (pl)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HUE041842T2 (hu)	2002-06-14	2019-05-28	Toyama Chemical Co Ltd	Gyógyászati készítmény agymûködés javítására
JP2005534710A (ja) *	2002-08-07	2005-11-17	ノバルティスアクチエンゲゼルシャフト	Ａｐｏｅ遺伝子型を基準とした痴呆を処置するための方法
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
MX2007007836A (es)	2004-12-27	2007-08-20	Eisai R&D Man Co Ltd	Metodo para estabilizar un farmaco anti-demencia.
RU2692258C2 (ru)	2014-01-31	2019-06-24	Когнишн Терапьютикс, Инк.	Композиции изоиндолина и способы лечения нейродегенеративного заболевания
DK3634394T3 (da)	2017-05-15	2026-03-02	Cognition Therapeutics Inc	Sammensætninger til behandling af neurogenerative sygdomme
KR102224918B1 (ko)	2018-03-20	2021-03-09	(주)인벤티지랩	도네페질 및 메만틴을 포함하는 인지 장애 관련 질병의 예방 또는 치료용 약학적 복합 조성물 및 이의 제조 방법
WO2019182319A1 (ko) *	2018-03-20	2019-09-26	(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
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)

* Cited by examiner, † Cited by third party
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
ES2244968T3 (es) *	1995-03-06	2005-12-16	Interneuron Pharmaceuticals Incorporated	Reduccion del volumen de infarto usando citocolina.
FR2736053B1 (fr) *	1995-06-28	1997-09-19	Sanofi Sa	Nouvelles 1-phenylalkyl-1,2,3,6-tetrahydropyridines

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 TR TR2000/01262T patent/TR200001262T2/xx unknown
- 1998-11-09 WO PCT/FR1998/002384 patent/WO1999025363A1/fr not_active Ceased
- 1998-11-09 CN CNB988130947A patent/CN1243540C/zh not_active Expired - Fee Related
- 1998-11-09 EP EP98954538A patent/EP1030671A1/fr not_active Withdrawn
- 1998-11-09 JP JP2000520796A patent/JP2001523642A/ja not_active Withdrawn
- 1998-11-09 BR BR9814035-3A patent/BR9814035A/pt not_active Application Discontinuation
- 1998-11-09 ID IDW20000860A patent/ID24933A/id unknown
- 1998-11-09 KR KR1020007005231A patent/KR100599350B1/ko not_active Expired - Fee Related
- 1998-11-09 IL IL13612298A patent/IL136122A0/xx not_active IP Right Cessation
- 1998-11-09 EA EA200000412A patent/EA003255B1/ru not_active IP Right Cessation
- 1998-11-09 EE EEP200000290A patent/EE04235B1/xx not_active IP Right Cessation
- 1998-11-09 NZ NZ504420A patent/NZ504420A/en unknown
- 1998-11-09 CA CA002309966A patent/CA2309966A1/en not_active Abandoned
- 1998-11-09 SK SK711-2000A patent/SK286040B6/sk unknown
- 1998-11-09 AU AU11609/99A patent/AU743228B2/en not_active Ceased
- 1998-11-09 HU HU0100098A patent/HUP0100098A3/hu unknown
- 1998-11-09 PL PL98340500A patent/PL194597B1/pl not_active IP Right Cessation
- 1998-11-11 DZ DZ980259A patent/DZ2649A1/xx active
- 1998-11-12 UY UY25247A patent/UY25247A1/es not_active IP Right Cessation
- 1998-11-14 SA SA98190747A patent/SA98190747B1/ar unknown
- 1998-11-14 MY MYPI98005180A patent/MY120461A/en unknown
2000
- 2000-05-09 IS IS5482A patent/IS5482A/is unknown
- 2000-05-11 BG BG104428A patent/BG64819B1/bg unknown
- 2000-05-11 NO NO20002450A patent/NO20002450L/no unknown
- 2000-05-12 OA OA1200000141A patent/OA11464A/en unknown
- 2000-05-14 IL IL136122A patent/IL136122A/en unknown

Also Published As

Publication number	Publication date
CN1285742A (zh)	2001-02-28
EP1030671A1 (fr)	2000-08-30
DZ2649A1 (fr)	2004-12-28
BR9814035A (pt)	2000-09-26
TW585766B (en)	2004-05-01
BG64819B1 (bg)	2006-05-31
UY25247A1 (es)	2001-05-31
EE200000290A (et)	2001-06-15
AU1160999A (en)	1999-06-07
KR100599350B1 (ko)	2006-07-12
OA11464A (en)	2003-11-18
CO4980891A1 (es)	2000-11-27
NZ504420A (en)	2003-08-29
PL194597B1 (pl)	2007-06-29
SK286040B6 (sk)	2008-01-07
IL136122A (en)	2006-07-05
EA200000412A1 (ru)	2000-12-25
KR20010032099A (ko)	2001-04-16
NO20002450D0 (no)	2000-05-11
JP2001523642A (ja)	2001-11-27
EA003255B1 (ru)	2003-02-27
SA98190747B1 (ar)	2006-11-04
CN1243540C (zh)	2006-03-01
BG104428A (en)	2001-08-31
TR200001262T2 (tr)	2001-01-22
IS5482A (is)	2000-05-09
SK7112000A3 (en)	2000-10-09
EE04235B1 (et)	2004-02-16
HUP0100098A2 (hu)	2001-07-30
MY120461A (en)	2005-10-31
IL136122A0 (en)	2001-05-20
NO20002450L (no)	2000-07-14
PL340500A1 (en)	2001-02-12
WO1999025363A1 (fr)	1999-05-27
ID24933A (id)	2000-08-31
HUP0100098A3 (en)	2001-12-28
AU743228B2 (en)	2002-01-24

Legal Events

Date	Code	Title	Description
2003-05-23	EEER	Examination request
2009-11-09	FZDE	Discontinued

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DE60122928T2 (de)	2007-09-06	Therapeutische zusammensetzung von amlodipin und benazepril / benazeprilat
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US20030092737A1 (en)	2003-05-15	Combination of active ingredients for the treatment of senile dementia of the Alzheimer type
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NL8004442A (nl)	1981-02-05	Nieuwe farmaceutische samenstellingen.
DE3736505A1 (de)	1988-05-05	Kombination von clacium antagonisten mit einem ace-hemmer
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WO2001022997A1 (en)	2001-04-05	Analgesics
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