CA2307748A1 - Derives d'aminomethyl-benzo[a]quinolizidine, leur preparation et leur application en therapeutique pour les maladies neurodegeneratives - Google Patents
Derives d'aminomethyl-benzo[a]quinolizidine, leur preparation et leur application en therapeutique pour les maladies neurodegeneratives Download PDFInfo
- Publication number
- CA2307748A1 CA2307748A1 CA002307748A CA2307748A CA2307748A1 CA 2307748 A1 CA2307748 A1 CA 2307748A1 CA 002307748 A CA002307748 A CA 002307748A CA 2307748 A CA2307748 A CA 2307748A CA 2307748 A1 CA2307748 A1 CA 2307748A1
- Authority
- CA
- Canada
- Prior art keywords
- hexahydro
- methoxy
- methyl
- benzo
- quinolizinyl
- 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
- 238000002360 preparation method Methods 0.000 title claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 6
- 201000010099 disease Diseases 0.000 title description 2
- DBZCEYIEDHAOOU-UHFFFAOYSA-N 2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-1-ylmethanamine Chemical class NCC1CCCN2CCC3=C(C12)C=CC=C3 DBZCEYIEDHAOOU-UHFFFAOYSA-N 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 15
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
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- 239000005864 Sulphur Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 159
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- 239000000203 mixture Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
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- JMLUTSLKEPINBK-UHFFFAOYSA-N 1,3-bis(methylsulfonyl)urea Chemical compound CS(=O)(=O)NC(NS(=O)(=O)C)=O JMLUTSLKEPINBK-UHFFFAOYSA-N 0.000 claims description 3
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- 239000011593 sulfur Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
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- 125000003441 thioacyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- WOGITNXCNOTRLK-UHFFFAOYSA-N 3-phenylprop-2-enoyl chloride Chemical class ClC(=O)C=CC1=CC=CC=C1 WOGITNXCNOTRLK-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
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- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims 1
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- DWOKRAWLJCSOFW-UHFFFAOYSA-N 2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-ylmethanamine Chemical class NCC1CCN2CCC3=C(C2C1)C=CC=C3 DWOKRAWLJCSOFW-UHFFFAOYSA-N 0.000 abstract 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR97/13499 | 1997-10-28 | ||
| FR9713499A FR2770215B1 (fr) | 1997-10-28 | 1997-10-28 | Derives d'aminomethyl-benzo[a]quinolizidine, leur preparation et leur application en therapeutique pour les maladies neurodegeneratives |
| PCT/FR1998/002281 WO1999021856A1 (fr) | 1997-10-28 | 1998-10-26 | Derives d'aminomethyl-benzo[a]quinolizidine, leur preparation et leur application en therapeutique pour les maladies neurodegeneratives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2307748A1 true CA2307748A1 (fr) | 1999-05-06 |
Family
ID=9512729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002307748A Abandoned CA2307748A1 (fr) | 1997-10-28 | 1998-10-26 | Derives d'aminomethyl-benzo[a]quinolizidine, leur preparation et leur application en therapeutique pour les maladies neurodegeneratives |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1027350A1 (de) |
| JP (1) | JP2001521034A (de) |
| CN (1) | CN1278260A (de) |
| AU (1) | AU9751798A (de) |
| BR (1) | BR9813303A (de) |
| CA (1) | CA2307748A1 (de) |
| FR (1) | FR2770215B1 (de) |
| WO (1) | WO1999021856A1 (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0016454D0 (en) | 2000-07-04 | 2000-08-23 | Hoffmann La Roche | Thienopyrrolidinones |
| JPWO2006054793A1 (ja) * | 2004-11-19 | 2008-06-05 | 財団法人新産業創造研究機構 | ベンゾフラン化合物、およびそれを含有してなる医薬組成物 |
| NZ566011A (en) * | 2005-08-06 | 2011-01-28 | Biovail Lab Internat Barbados Srl | 3, 11b cis dihydrotetrabenazine for the treatment of schizophrenia and other psychoses |
| CA2650904C (en) * | 2006-05-02 | 2015-07-07 | The Trustees Of The University Of Pennsylvania | Radiolabeled dihydrotetrabenazine derivatives and their use as imaging agents |
| GB2463451A (en) * | 2008-09-08 | 2010-03-17 | Cambridge Lab | 3, 11b cis-dihydrotetrabenazine compounds for use in the treatment of dementia |
| FR2976287B1 (fr) * | 2011-06-09 | 2013-07-05 | Pf Medicament | Derives benzoquinolizidines, leur procede de preparation et leurs applications en therapeutique |
| CA2849057C (en) * | 2011-09-19 | 2021-05-11 | Vitas Pharma Research Pvt Ltd | Heterocyclic compounds as inhibitors of fatty acid biosynthesis for bacterial infections |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8416432D0 (en) * | 1984-06-28 | 1984-08-01 | Wyeth John & Brother Ltd | Benzoquinolizines |
-
1997
- 1997-10-28 FR FR9713499A patent/FR2770215B1/fr not_active Expired - Fee Related
-
1998
- 1998-10-26 JP JP2000517966A patent/JP2001521034A/ja active Pending
- 1998-10-26 AU AU97517/98A patent/AU9751798A/en not_active Abandoned
- 1998-10-26 EP EP98951548A patent/EP1027350A1/de not_active Withdrawn
- 1998-10-26 CN CN98810769A patent/CN1278260A/zh active Pending
- 1998-10-26 BR BR9813303-9A patent/BR9813303A/pt not_active Application Discontinuation
- 1998-10-26 CA CA002307748A patent/CA2307748A1/fr not_active Abandoned
- 1998-10-26 WO PCT/FR1998/002281 patent/WO1999021856A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999021856A1 (fr) | 1999-05-06 |
| BR9813303A (pt) | 2000-08-29 |
| EP1027350A1 (de) | 2000-08-16 |
| AU9751798A (en) | 1999-05-17 |
| FR2770215A1 (fr) | 1999-04-30 |
| FR2770215B1 (fr) | 2000-01-14 |
| JP2001521034A (ja) | 2001-11-06 |
| CN1278260A (zh) | 2000-12-27 |
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