JPS6039679B2 - 五環系誘導体及びその製造方法 - Google Patents
五環系誘導体及びその製造方法Info
- Publication number
- JPS6039679B2 JPS6039679B2 JP51074537A JP7453776A JPS6039679B2 JP S6039679 B2 JPS6039679 B2 JP S6039679B2 JP 51074537 A JP51074537 A JP 51074537A JP 7453776 A JP7453776 A JP 7453776A JP S6039679 B2 JPS6039679 B2 JP S6039679B2
- Authority
- JP
- Japan
- Prior art keywords
- add
- formula
- solution
- water
- minutes
- 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.)
- Expired
Links
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- 150000003839 salts Chemical class 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 25
- -1 methylenedioxy group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
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- 239000000126 substance Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
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- 125000005843 halogen group Chemical group 0.000 claims description 3
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- 239000003513 alkali Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
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- 239000011541 reaction mixture Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- VOCGEKMEZOPDFP-UHFFFAOYSA-N 2-(6-methoxy-1h-indol-3-yl)ethanamine Chemical compound COC1=CC=C2C(CCN)=CNC2=C1 VOCGEKMEZOPDFP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- 241000282693 Cercopithecidae Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
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- 239000011259 mixed solution Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- IXGNPUSUVRTQGW-UHFFFAOYSA-M sodium;perchlorate;hydrate Chemical compound O.[Na+].[O-]Cl(=O)(=O)=O IXGNPUSUVRTQGW-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960002726 vincamine Drugs 0.000 description 1
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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7519960A FR2315277A1 (fr) | 1975-06-25 | 1975-06-25 | Nouveaux derives pentacycliques, leur preparation et les compositions qui les contiennent |
| FR7519960 | 1975-06-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5217488A JPS5217488A (en) | 1977-02-09 |
| JPS6039679B2 true JPS6039679B2 (ja) | 1985-09-06 |
Family
ID=9157046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51074537A Expired JPS6039679B2 (ja) | 1975-06-25 | 1976-06-25 | 五環系誘導体及びその製造方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4138489A (en, 2012) |
| JP (1) | JPS6039679B2 (en, 2012) |
| AU (1) | AU496905B2 (en, 2012) |
| BE (1) | BE843215A (en, 2012) |
| CH (1) | CH616425A5 (en, 2012) |
| DE (1) | DE2627190A1 (en, 2012) |
| DK (1) | DK285576A (en, 2012) |
| ES (1) | ES449209A1 (en, 2012) |
| FR (1) | FR2315277A1 (en, 2012) |
| GB (1) | GB1543807A (en, 2012) |
| HU (1) | HU174882B (en, 2012) |
| IE (1) | IE43138B1 (en, 2012) |
| IL (1) | IL49864A0 (en, 2012) |
| LU (1) | LU75242A1 (en, 2012) |
| NL (1) | NL7606884A (en, 2012) |
| SE (1) | SE420730B (en, 2012) |
| ZA (1) | ZA763779B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA786426B (en) * | 1977-11-25 | 1979-10-31 | Scras | New indulo(2,3-a)quinolizidines,preparation and therapeutic use |
| US4428877A (en) | 1978-07-12 | 1984-01-31 | Richter Gedeon Vegyeszeti Gyar Rt. | Cis-10-bromo-E-homoeburnanes |
| IT1248881B (it) * | 1989-06-21 | 1995-01-30 | Richter Gedeon Vegyeszet | Derivati diesteri di ottaidro-indolo/2,3-a/tetraidropiramil/2,3-c/ chinolizina racemici ed otticamente attivi e procedimento per la loro preparazione |
| ITRM20010356A1 (it) * | 2001-06-21 | 2002-12-23 | Sigma Tau Ind Farmaceuti | "5-alogeno derivati della triptamina utili come ligandi del recettore5-ht6 e/o 5-ht7 della serotonina. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536725A (en) * | 1967-11-22 | 1970-10-27 | Miles Lab | Cyanoethylated derivatives of 2,3,4,6,7,12-hexahydroindolo(2,3-alpha)-quinolizine |
| FR2168853B1 (en, 2012) * | 1972-01-24 | 1975-04-25 | Centre Etd Ind Pharma |
-
1975
- 1975-06-25 FR FR7519960A patent/FR2315277A1/fr active Granted
-
1976
- 1976-06-14 CH CH751576A patent/CH616425A5/fr not_active IP Right Cessation
- 1976-06-16 DE DE19762627190 patent/DE2627190A1/de not_active Ceased
- 1976-06-21 BE BE168153A patent/BE843215A/xx not_active IP Right Cessation
- 1976-06-21 IE IE1337/76A patent/IE43138B1/en unknown
- 1976-06-22 IL IL49864A patent/IL49864A0/xx unknown
- 1976-06-23 GB GB26130/76A patent/GB1543807A/en not_active Expired
- 1976-06-23 SE SE7607231A patent/SE420730B/xx unknown
- 1976-06-24 ZA ZA763779A patent/ZA763779B/xx unknown
- 1976-06-24 DK DK285576A patent/DK285576A/da not_active Application Discontinuation
- 1976-06-24 NL NL7606884A patent/NL7606884A/xx not_active Application Discontinuation
- 1976-06-24 HU HU76AE468A patent/HU174882B/hu unknown
- 1976-06-24 AU AU15236/76A patent/AU496905B2/en not_active Expired
- 1976-06-25 ES ES449209A patent/ES449209A1/es not_active Expired
- 1976-06-25 JP JP51074537A patent/JPS6039679B2/ja not_active Expired
- 1976-06-25 LU LU75242A patent/LU75242A1/xx unknown
- 1976-06-25 US US05/700,028 patent/US4138489A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE7607231L (sv) | 1976-12-26 |
| BE843215A (fr) | 1976-12-21 |
| IE43138B1 (en) | 1980-12-31 |
| ZA763779B (en) | 1977-06-29 |
| FR2315277A1 (fr) | 1977-01-21 |
| AU1523676A (en) | 1978-01-05 |
| LU75242A1 (en, 2012) | 1978-01-18 |
| IL49864A0 (en) | 1976-08-31 |
| DE2627190A1 (de) | 1977-01-20 |
| AU496905B2 (en) | 1978-11-09 |
| GB1543807A (en) | 1979-04-04 |
| NL7606884A (nl) | 1976-12-28 |
| HU174882B (hu) | 1980-04-28 |
| FR2315277B1 (en, 2012) | 1979-08-10 |
| US4138489A (en) | 1979-02-06 |
| DK285576A (da) | 1976-12-26 |
| ES449209A1 (es) | 1977-07-16 |
| JPS5217488A (en) | 1977-02-09 |
| SE420730B (sv) | 1981-10-26 |
| CH616425A5 (en, 2012) | 1980-03-31 |
| IE43138L (en) | 1976-12-25 |
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