KR830003480A - 헥사하이드로-트랜스-피리도인돌 신경 이완제 - Google Patents
헥사하이드로-트랜스-피리도인돌 신경 이완제 Download PDFInfo
- Publication number
- KR830003480A KR830003480A KR1019800003000A KR800003000A KR830003480A KR 830003480 A KR830003480 A KR 830003480A KR 1019800003000 A KR1019800003000 A KR 1019800003000A KR 800003000 A KR800003000 A KR 800003000A KR 830003480 A KR830003480 A KR 830003480A
- Authority
- KR
- South Korea
- Prior art keywords
- halides
- formula
- carbon atoms
- benzoyl
- inert solvent
- Prior art date
Links
- CCFNZJZCYYFGHV-KWQFWETISA-N (3aS,9bS)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline Chemical compound C1CC2=NC=CC=C2[C@@H]2[C@@H]1CCN2 CCFNZJZCYYFGHV-KWQFWETISA-N 0.000 title 1
- 239000003176 neuroleptic agent Substances 0.000 title 1
- 230000000701 neuroleptic effect Effects 0.000 title 1
- -1 lithium aluminum hydride Chemical compound 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 239000012442 inert solvent Substances 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 230000003472 neutralizing effect Effects 0.000 claims 2
- 150000003461 sulfonyl halides Chemical class 0.000 claims 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical class N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000003049 inorganic solvent Substances 0.000 claims 1
- 229910001867 inorganic solvent Inorganic materials 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- R이 H일 때는 다음 구조식(Ⅳ)의 니트릴을 에테르성 용매내에서 금속 수소화물과 반응시키거나 무기용매내의 귀금속 상에서 수소와 반응시켜 환원시키며
- R이 알킬일 때는 구조식(Ⅴ)의 아민을 중화제를 함유하고 있는 불활성 용매내에서 알킬할라 이드나 셀페이트로 알킬화하거나R이 알킬인 구조식(Ⅵ)의 아실레이트를 불활성용매내에서 리튬 알루미늄 하이드라이드로 환원시키고
- R이 아실 또는 설포닐일 때는 구조식(Ⅴ)의 화합물을 탄소수 1내지 3의 알카노일 할라이드, 탄소수 2내지 3의 알콕시카보닐 할라이드, 벤조일 할라이드, 페닐설포닐 할라이드 또는 벤조일이나 페닐설포닐 할라이드의 모노치환형(치환체는 불소, 염소, 브롬)등의 아실 또는 설포닐 할라이드와, 중화제를 함유하고 있는 불활성용매내에서 반응시키거나 구조식(Ⅴ)의 아민을 아실 또는 설포닐 할라이드에 상응하는 카복실산이나 설폰산과, 디사이클로헥실 카보디이미드를 함유하는 불활성 용매내에서 반응시켜 다음 구조식(Ⅰ)의 헥사하이드로-트랜스-4a,9b-1(H)피리도인돌 유도체의 (+)에난티오머 (+)와 (-)에난티오머의 혼합물 또는 (±)라세미체 및 이들의 약학적으로 무독한 염을 제조하는 방법.상기 구조식에서m은 2내지 9X와 Y는 각각 독립적으로 H 또는 F를 나타내며R은 H, 탄소수 1내지 3의 알킬, 탄소수 1내지 3의 알카노일, 탄소수 2내지 3의 알콕시카보닐, 벤조일, 페닐설포닐 또는 벤조일이나 페닐설포닐의 몬노치환형(치환체는 불소, 염소, 브롬 또는 메톡시이다)을 나타낸다.* 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/061,573 US4252811A (en) | 1979-07-30 | 1979-07-30 | Hexahydro-trans-pyridoindole neuroleptic agents |
| US61573 | 1979-07-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830003480A true KR830003480A (ko) | 1983-06-20 |
| KR840000914B1 KR840000914B1 (ko) | 1984-06-28 |
Family
ID=22036658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019800003000A KR840000914B1 (ko) | 1979-07-30 | 1980-07-28 | 헥사하이드로-트랜스-피리도인들의 제조방법 |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4252811A (ko) |
| JP (1) | JPS5626891A (ko) |
| KR (1) | KR840000914B1 (ko) |
| AR (1) | AR226314A1 (ko) |
| AT (1) | AT375659B (ko) |
| AU (1) | AU513948B2 (ko) |
| BE (1) | BE884530A (ko) |
| CA (1) | CA1133483A (ko) |
| CH (1) | CH644379A5 (ko) |
| CS (1) | CS221974B2 (ko) |
| DD (1) | DD153691A5 (ko) |
| DE (1) | DE3028555A1 (ko) |
| DK (1) | DK148140C (ko) |
| EG (1) | EG14903A (ko) |
| ES (1) | ES8105732A1 (ko) |
| FI (1) | FI68828C (ko) |
| FR (1) | FR2463140A1 (ko) |
| GB (1) | GB2055372B (ko) |
| GR (1) | GR69664B (ko) |
| IE (1) | IE50035B1 (ko) |
| IL (1) | IL60695A (ko) |
| IT (1) | IT1194815B (ko) |
| LU (1) | LU82662A1 (ko) |
| NL (1) | NL180216C (ko) |
| NO (1) | NO153729C (ko) |
| NZ (1) | NZ194467A (ko) |
| PH (1) | PH22657A (ko) |
| PL (1) | PL133456B1 (ko) |
| PT (1) | PT71623B (ko) |
| SE (1) | SE438505B (ko) |
| SU (1) | SU1172450A3 (ko) |
| YU (1) | YU42223B (ko) |
| ZA (1) | ZA804604B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337250A (en) * | 1979-07-30 | 1982-06-29 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US4748247A (en) * | 1986-10-21 | 1988-05-31 | American Home Products Corporation | 2-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]alkyl]alkyl]pyrido- and pyrazino-indole-1,3-dione derivatives as histamine H1 antagonists |
| US5229517A (en) * | 1990-09-27 | 1993-07-20 | Hoechst-Roussel Pharmaceuticals Incorporated | 2-(4-Piperindinyl)-1H-pyrido[4,3-B]indol-1-ones and related compounds |
| US5102889B1 (en) * | 1990-09-27 | 1993-05-11 | 2-(4-piperidinyl)-1h-pyrido(4,3-b)indol-1-ones and related compounds | |
| JPH05101365A (ja) * | 1991-03-22 | 1993-04-23 | Tdk Corp | 垂直磁気記録媒体およびその製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3687961A (en) * | 1971-05-03 | 1972-08-29 | Abbott Lab | 8-fluoro-2-{8 3-(4-fluorophenylanilinopropyl{9 -gamma-carboline |
| AR205452A1 (es) * | 1973-12-06 | 1976-05-07 | Endo Lab | Metodo para preparar nuevos trans-2, 3, 4, 4a, 5, 9b-hexahidro-5-fenil-1h-pirido(4,3-b) indoles |
| JPS50126699A (ko) * | 1974-03-20 | 1975-10-04 | ||
| US4001263A (en) * | 1974-04-01 | 1977-01-04 | Pfizer Inc. | 5-Aryl-1,2,3,4-tetrahydro-γ-carbolines |
| SE7702301L (sv) * | 1976-04-08 | 1977-10-09 | Endo Lab | Trans-hexahydro-pyrido-indoler |
-
1979
- 1979-07-30 US US06/061,573 patent/US4252811A/en not_active Expired - Lifetime
-
1980
- 1980-06-18 DK DK260080A patent/DK148140C/da not_active IP Right Cessation
- 1980-07-18 CH CH552180A patent/CH644379A5/fr not_active IP Right Cessation
- 1980-07-24 SU SU802955229A patent/SU1172450A3/ru active
- 1980-07-25 CS CS805260A patent/CS221974B2/cs unknown
- 1980-07-28 DD DD80222915A patent/DD153691A5/de unknown
- 1980-07-28 NZ NZ194467A patent/NZ194467A/en unknown
- 1980-07-28 DE DE19803028555 patent/DE3028555A1/de not_active Ceased
- 1980-07-28 GB GB8024682A patent/GB2055372B/en not_active Expired
- 1980-07-28 PL PL1980225940A patent/PL133456B1/pl unknown
- 1980-07-28 GR GR62556A patent/GR69664B/el unknown
- 1980-07-28 LU LU82662A patent/LU82662A1/fr unknown
- 1980-07-28 JP JP10353280A patent/JPS5626891A/ja active Granted
- 1980-07-28 KR KR1019800003000A patent/KR840000914B1/ko active IP Right Grant
- 1980-07-28 AR AR281942A patent/AR226314A1/es active
- 1980-07-29 NL NLAANVRAGE8004332,A patent/NL180216C/xx not_active IP Right Cessation
- 1980-07-29 IT IT23785/80A patent/IT1194815B/it active
- 1980-07-29 SE SE8005453A patent/SE438505B/sv not_active IP Right Cessation
- 1980-07-29 FI FI802371A patent/FI68828C/fi not_active IP Right Cessation
- 1980-07-29 NO NO802274A patent/NO153729C/no unknown
- 1980-07-29 ES ES493818A patent/ES8105732A1/es not_active Expired
- 1980-07-29 YU YU1917/80A patent/YU42223B/xx unknown
- 1980-07-29 BE BE0/201571A patent/BE884530A/fr not_active IP Right Cessation
- 1980-07-29 ZA ZA00804604A patent/ZA804604B/xx unknown
- 1980-07-29 FR FR8016698A patent/FR2463140A1/fr active Granted
- 1980-07-29 PT PT71623A patent/PT71623B/pt unknown
- 1980-07-29 AT AT0393280A patent/AT375659B/de not_active IP Right Cessation
- 1980-07-29 CA CA357,265A patent/CA1133483A/en not_active Expired
- 1980-07-29 IE IE1576/80A patent/IE50035B1/en unknown
- 1980-07-29 PH PH24365A patent/PH22657A/en unknown
- 1980-07-29 AU AU60869/80A patent/AU513948B2/en not_active Ceased
- 1980-07-29 IL IL60695A patent/IL60695A/xx unknown
- 1980-07-30 EG EG458/80A patent/EG14903A/xx active
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| Date | Code | Title | Description |
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| E701 | Decision to grant or registration of patent right |