KR840006656A - 1,3,4,6,7,11b-헥사하이드로-7-아릴-2H-피라지노[2,1-α]이소퀴놀린의 제조방법 - Google Patents
1,3,4,6,7,11b-헥사하이드로-7-아릴-2H-피라지노[2,1-α]이소퀴놀린의 제조방법 Download PDFInfo
- Publication number
- KR840006656A KR840006656A KR1019830004928A KR830004928A KR840006656A KR 840006656 A KR840006656 A KR 840006656A KR 1019830004928 A KR1019830004928 A KR 1019830004928A KR 830004928 A KR830004928 A KR 830004928A KR 840006656 A KR840006656 A KR 840006656A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen
- compound
- formula
- lower alkyl
- reacting
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 9
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- -1 aralkanoyl Chemical group 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 238000007336 electrophilic substitution reaction Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims 1
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000005256 alkoxyacyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000012380 dealkylating agent Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 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
- C07D471/02—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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- (a) 하기 일반식(Ⅱ)의 화합물을 옥살산 또는 이의 저급 알킬에스테르와 반응시켜 디아미드를 제조한 다음, 디아미드를 착수소화물 환원제로 환원시켜 R1이 수소 또는 저급알킬인 일반식(Ⅰ)의 화합물을 제조하거나, (b) R1이 저급알킬인 상기 (a) 또는 후술할 (d) 단계의 생성물을 탈알킬화제와 반응시켜 R1R1이 수소인 일반식(Ⅰ)의 화합물을 제조하거나, (o) R1이 수소인 상기 (a) 또는 (b) 단계의 생성물을 아실, 아로일 또는 아르알카노일 할라이드와 반응시켜 아미드를 생성하고, 이어서 환원시켜 알킬, 시클로알킬, 또는 아르알킬기 함유 화합물을 제조하고, (d) R2및 R3위치에 수소가 아닌 치환제를 원할 경우, 상기 (a) 또는 (c) 단계의 생성물을 직접 친전자성 치환 반응시킴을 특징으로하는 하여 하기 일반식(Ⅰ)의 화합물 및 이의염을 제조하는 방법.상기 일반식에서 R1은 수소, 저급알킬, 시클로알킬, 알카노일, 아르알킬, 아르알카노일, 아릴 또는 아로일이고 R2및 R3는 동일하거나 상이하며, 수소, 할로겐, 히드록시, 아실옥시, 니트로, 아미노, 아미노알킬, 트리플루오로메틸, 알킬, 알콕시아실, 시아미 또는 알킬 아미노이고, Z는 수소 또는 저급알킬이다.
- 제1항에 있어서, 공정을 (a) 단계에서 종결하여 R2및 R3가 수소이고, R1이 수소 또는 저급알킬인 일반식(Ⅰ)의 화합물을 제조하는 방법
- 제2항에 있어서, Z가 메틸인 방법.
- 제3항에 있어서, 질산과 반응 시킴으로써 친전자성 치환 반응을 수행하여 R2및/또는 R3가 니트로인 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 제1항에 있어서, 일반식(Ⅰ)의 화합물을, 이의 디아스 테레오아이소머 염을 분별 결정시켜 이의 광학 이성체로 분할 시키는 방법.
- 제5항에 있어서, R1이 메틸이고 R2및 R3가 수소인 일반식(Ⅰ) 화합물의 시스형을(-)디벤조일-L-타르타르산을 사용하여 분할시키는 방법.
- 제5항에 있어서, R1이 메틸이고 R2및 R3가 수소인 일반식(Ⅰ) 화합물의 시스형을(+)디벤조일-D-타르타르산을 사용하여 분할시키는 방법.※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/435,132 US4517187A (en) | 1982-10-18 | 1982-10-18 | 1,3,4,6,7-11b-Hexahydro-7-phenyl-2H-pyrazino[2,1-a]isoquinolines methods of preparation, and use as antidepressants |
| US435,132 | 1982-10-18 | ||
| US435132 | 1999-11-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840006656A true KR840006656A (ko) | 1984-12-01 |
| KR870000622B1 KR870000622B1 (ko) | 1987-03-26 |
Family
ID=23727113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830004928A KR870000622B1 (ko) | 1982-10-18 | 1983-10-18 | 1,3,4,6,7,11b-헥사하이드로-7-아릴-2H-피라지노[2,1-α]이소퀴놀린의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4517187A (ko) |
| EP (1) | EP0107825B1 (ko) |
| JP (1) | JPS5989680A (ko) |
| KR (1) | KR870000622B1 (ko) |
| AT (1) | ATE32720T1 (ko) |
| AU (1) | AU1955583A (ko) |
| CA (1) | CA1219874A (ko) |
| DE (1) | DE3375784D1 (ko) |
| DK (1) | DK477783A (ko) |
| FI (1) | FI833784A (ko) |
| IL (1) | IL69586A (ko) |
| NO (1) | NO833778L (ko) |
| NZ (1) | NZ205425A (ko) |
| ZA (1) | ZA836448B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4782058A (en) * | 1985-04-26 | 1988-11-01 | Pennwalt Corporation | 1,3,4,6,7,11b-Hexahydro-6-phenyl-2H-pyrazino-(2,1-a)isoquinolines, for anti-histamine or anti-depression treatment |
| US4678791A (en) * | 1985-05-07 | 1987-07-07 | Pennwalt Corporation | 6-phenyl-1,2-3,4,4a,5-6,10b-octahydrobenz(h)isoquinolines useful for treating depression |
| US4772705A (en) * | 1985-07-25 | 1988-09-20 | Pennwalt Corporation | Processes for the preparation of trans 1,3,4,6,7,11b-hexahydro-7-aryl-2H-pyrazinol[2,1-a]isoquinolines |
| MX19222A (es) * | 1989-01-23 | 1993-12-01 | Pfizer | Agentes ansioliticos bis-aza-biciclicos |
| KR100244848B1 (ko) * | 1994-09-30 | 2000-03-02 | 디. 제이. 우드, 스피겔 알렌 제이 | 2,7-치환된 옥타하이드로-1H-피리도[1,2-a] 피라진 유도체 |
| RU2017106928A (ru) * | 2014-08-27 | 2018-10-01 | Ф. Хоффманн-Ля Рош Аг | Замещенные производные пиразино[2,1-а]изохинолина для лечения заболеваний цнс |
| IL292631A (en) * | 2019-10-31 | 2022-07-01 | Holosmedic | A new pharmaceutical substance and compound for the prevention or treatment of cancer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1050901A (ko) * | 1964-02-06 | |||
| US3684813A (en) * | 1970-04-08 | 1972-08-15 | Sterling Drug Inc | Hexahydropyrazinoisoquinolines |
| DE2441261A1 (de) * | 1974-08-28 | 1976-03-18 | Merck Patent Gmbh | Ringsubstituierte pyrazino-isochinolin-derivat und verfahren zu ihrer herstellung |
| US4162319A (en) * | 1974-08-28 | 1979-07-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Ring substituted pyrazino-isoquinoline derivatives and their preparation |
-
1982
- 1982-10-18 US US06/435,132 patent/US4517187A/en not_active Expired - Fee Related
-
1983
- 1983-08-26 CA CA000435430A patent/CA1219874A/en not_active Expired
- 1983-08-29 IL IL69586A patent/IL69586A/xx unknown
- 1983-08-30 NZ NZ205425A patent/NZ205425A/en unknown
- 1983-08-31 ZA ZA836448A patent/ZA836448B/xx unknown
- 1983-09-26 AU AU19555/83A patent/AU1955583A/en not_active Abandoned
- 1983-10-07 EP EP83110044A patent/EP0107825B1/en not_active Expired
- 1983-10-07 DE DE8383110044T patent/DE3375784D1/de not_active Expired
- 1983-10-07 AT AT83110044T patent/ATE32720T1/de not_active IP Right Cessation
- 1983-10-13 JP JP58190025A patent/JPS5989680A/ja active Pending
- 1983-10-17 FI FI833784A patent/FI833784A/fi not_active Application Discontinuation
- 1983-10-17 DK DK477783A patent/DK477783A/da not_active Application Discontinuation
- 1983-10-17 NO NO833778A patent/NO833778L/no unknown
- 1983-10-18 KR KR1019830004928A patent/KR870000622B1/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| ZA836448B (en) | 1984-07-25 |
| IL69586A0 (en) | 1983-11-30 |
| AU1955583A (en) | 1984-05-03 |
| DK477783D0 (da) | 1983-10-17 |
| FI833784A (fi) | 1984-04-19 |
| ATE32720T1 (de) | 1988-03-15 |
| EP0107825A1 (en) | 1984-05-09 |
| JPS5989680A (ja) | 1984-05-23 |
| DK477783A (da) | 1984-04-19 |
| US4517187A (en) | 1985-05-14 |
| NO833778L (no) | 1984-04-24 |
| CA1219874A (en) | 1987-03-31 |
| EP0107825B1 (en) | 1988-03-02 |
| KR870000622B1 (ko) | 1987-03-26 |
| IL69586A (en) | 1986-07-31 |
| DE3375784D1 (en) | 1988-04-07 |
| NZ205425A (en) | 1986-05-09 |
| FI833784A0 (fi) | 1983-10-17 |
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