CS266586B2 - Method of new racemic or optically active berbane derivatives production - Google Patents
Method of new racemic or optically active berbane derivatives production Download PDFInfo
- Publication number
- CS266586B2 CS266586B2 CS863767A CS376786A CS266586B2 CS 266586 B2 CS266586 B2 CS 266586B2 CS 863767 A CS863767 A CS 863767A CS 376786 A CS376786 A CS 376786A CS 266586 B2 CS266586 B2 CS 266586B2
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- Czechoslovakia
- Prior art keywords
- compounds
- formula
- group
- optically active
- preparation
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- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 229910052987 metal hydride Inorganic materials 0.000 claims description 6
- 150000004681 metal hydrides Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
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- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 1
- SSVFMICWXDVRQN-UHFFFAOYSA-N ethanol;sodium Chemical compound [Na].CCO SSVFMICWXDVRQN-UHFFFAOYSA-N 0.000 claims 1
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- 125000003118 aryl group Chemical group 0.000 abstract description 7
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- 125000001931 aliphatic group Chemical group 0.000 abstract description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
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- 239000000126 substance Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- 229910052799 carbon Inorganic materials 0.000 description 51
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- HPMRFMKYPGXPEP-UHFFFAOYSA-N idazoxan Chemical compound N1CCN=C1C1OC2=CC=CC=C2OC1 HPMRFMKYPGXPEP-UHFFFAOYSA-N 0.000 description 5
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- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 210000003405 ileum Anatomy 0.000 description 4
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 4
- 229960001999 phentolamine Drugs 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
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- NHTGHBARYWONDQ-JTQLQIEISA-N L-α-methyl-Tyrosine Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-JTQLQIEISA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Emergency Protection Circuit Devices (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Train Traffic Observation, Control, And Security (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU851982A HU195505B (en) | 1985-05-24 | 1985-05-24 | Process for producing 7,8-methylendioxy-14-hydroxy-berban derivatives and pharmaceuticals comprising the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS376786A2 CS376786A2 (en) | 1989-04-14 |
| CS266586B2 true CS266586B2 (en) | 1990-01-12 |
Family
ID=10957145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS863767A CS266586B2 (en) | 1985-05-24 | 1986-05-23 | Method of new racemic or optically active berbane derivatives production |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4851416A (de) |
| EP (1) | EP0202950B1 (de) |
| JP (1) | JPS61280492A (de) |
| KR (1) | KR870001742B1 (de) |
| CN (1) | CN1010779B (de) |
| AT (1) | ATE95180T1 (de) |
| AU (1) | AU599030B2 (de) |
| CA (1) | CA1294964C (de) |
| CS (1) | CS266586B2 (de) |
| DD (1) | DD251289A5 (de) |
| DE (1) | DE3689080T2 (de) |
| DK (1) | DK242886A (de) |
| ES (1) | ES8800938A1 (de) |
| FI (1) | FI85023C (de) |
| GR (1) | GR861348B (de) |
| HU (1) | HU195505B (de) |
| IE (1) | IE60479B1 (de) |
| IL (1) | IL78722A (de) |
| NO (1) | NO164098C (de) |
| NZ (1) | NZ216280A (de) |
| PH (1) | PH24053A (de) |
| PL (1) | PL148617B1 (de) |
| PT (1) | PT82634B (de) |
| SU (2) | SU1508958A3 (de) |
| YU (1) | YU46956B (de) |
| ZA (1) | ZA863869B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5122504A (en) * | 1990-02-27 | 1992-06-16 | The Board Of Trustees Of The Leland Stanford Junior University | Superconducting ribbon process using laser heating |
| WO1992020678A1 (en) * | 1991-05-22 | 1992-11-26 | Chinoin Gyógyszer- És Vegyészeti Gyár R.T. | New berbane derivatives, pharmaceutical compositions containing these compounds and process for the preparation of same |
| US5663167A (en) * | 1992-12-09 | 1997-09-02 | The United States Of America As Represented By The Department Of Health And Human Services | Antipsychotic composition and method of treatment |
| US5492907A (en) * | 1992-12-09 | 1996-02-20 | The United States Of America As Represented By The Department Of Health & Human Services | Antipsychotic composition and method of treatment |
| FR2728902B1 (fr) * | 1994-12-29 | 1997-01-31 | Synthelabo | Derives d'acide 8-oxo-5,8-dihydro-6h-dibenzo(a,g)quinolizine-13-propanoique, leur preparation et leur application en therapeutique |
| KR20000042507A (ko) * | 1998-12-21 | 2000-07-15 | 박원배 | 콜레스테롤 생합성 저해효과를 나타내는 디벤조[a,g]퀴놀리지늄 유도체 |
-
1985
- 1985-05-24 HU HU851982A patent/HU195505B/hu unknown
-
1986
- 1986-05-08 IL IL78722A patent/IL78722A/xx not_active IP Right Cessation
- 1986-05-21 JP JP61114973A patent/JPS61280492A/ja active Pending
- 1986-05-21 YU YU84886A patent/YU46956B/sh unknown
- 1986-05-22 ES ES555206A patent/ES8800938A1/es not_active Expired
- 1986-05-23 PL PL1986259689A patent/PL148617B1/pl unknown
- 1986-05-23 US US06/867,323 patent/US4851416A/en not_active Expired - Fee Related
- 1986-05-23 SU SU864027562A patent/SU1508958A3/ru active
- 1986-05-23 CA CA000509814A patent/CA1294964C/en not_active Expired - Lifetime
- 1986-05-23 EP EP86303947A patent/EP0202950B1/de not_active Expired - Lifetime
- 1986-05-23 PH PH33811A patent/PH24053A/en unknown
- 1986-05-23 DD DD86290542A patent/DD251289A5/de not_active IP Right Cessation
- 1986-05-23 ZA ZA863869A patent/ZA863869B/xx unknown
- 1986-05-23 PT PT82634A patent/PT82634B/pt not_active IP Right Cessation
- 1986-05-23 AT AT86303947T patent/ATE95180T1/de not_active IP Right Cessation
- 1986-05-23 FI FI862174A patent/FI85023C/fi not_active IP Right Cessation
- 1986-05-23 NZ NZ216280A patent/NZ216280A/xx unknown
- 1986-05-23 IE IE137386A patent/IE60479B1/en not_active IP Right Cessation
- 1986-05-23 DK DK242886A patent/DK242886A/da not_active Application Discontinuation
- 1986-05-23 GR GR861348A patent/GR861348B/el unknown
- 1986-05-23 AU AU57853/86A patent/AU599030B2/en not_active Ceased
- 1986-05-23 DE DE86303947T patent/DE3689080T2/de not_active Expired - Fee Related
- 1986-05-23 KR KR1019860004054A patent/KR870001742B1/ko not_active Expired
- 1986-05-23 CN CN85104693A patent/CN1010779B/zh not_active Expired
- 1986-05-23 CS CS863767A patent/CS266586B2/cs unknown
- 1986-05-23 NO NO862054A patent/NO164098C/no unknown
- 1986-09-29 SU SU864028190A patent/SU1573021A1/ru active
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