KR850004759A - 피롤로[3,2,1-hi]인돌 유도체, 그의 제법 및 그를 함유하는 의약조성물 - Google Patents
피롤로[3,2,1-hi]인돌 유도체, 그의 제법 및 그를 함유하는 의약조성물 Download PDFInfo
- Publication number
- KR850004759A KR850004759A KR1019840007549A KR840007549A KR850004759A KR 850004759 A KR850004759 A KR 850004759A KR 1019840007549 A KR1019840007549 A KR 1019840007549A KR 840007549 A KR840007549 A KR 840007549A KR 850004759 A KR850004759 A KR 850004759A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- pyrrolo
- pharmaceutically acceptable
- alkyl
- preparing
- Prior art date
Links
- JLTRNSWADPSQBA-UHFFFAOYSA-N 4-azatricyclo[5.3.1.04,11]undeca-1(11),2,5,7,9-pentaene Chemical class C1=CC2=CC=CC3=C2N1C=C3 JLTRNSWADPSQBA-UHFFFAOYSA-N 0.000 title claims 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- MGHKJOLSHKWREX-UHFFFAOYSA-N CCCC[Ir] Chemical compound CCCC[Ir] MGHKJOLSHKWREX-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229940043279 diisopropylamine Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 일반식(Ⅱ)의 에스테르를 주위온도에서 주석의 존재하에 염산에 의하여 수소화하는 단계와, 다음에 일반식(Ⅲ)의 결과 화합물을 트리메틸 알루미늄의 존재하에 에틸렌디아민과 반응시켜 R이 수소인 화합물(Ⅰ)을 얻거나, 또는 일반식(Ⅲ)의 결과 화합물을 할로겐화알킬 RX, 여기서 R은 C1-C4알킬이고 X는 할로겐인데, 이것과 반응시킴으로써 알킬화시키는 단계와, 그 다음 일반식(Ⅳ)의 결과 화합물을 트리메틸 알루미늄의 존재하에 에틸렌디아민과 반응시켜 R이 알킬인 화합물(Ⅰ)을 얻는 단계, 로 이루어지는 것과 만일 원한다면 결과화합물(Ⅰ)을 제약상 허용되는 부가염으로 변환시키는 것을 특징으로 하는, 라세미체 또는 광학활성 이성질체의 형태로 일반식(Ⅰ)의 피롤로[3,2,1-hi]인돌 유도체와 제약상 허용되는 그의 산부가염을 제조하는 방법.상기식에서, R은 수소이거나 선형 또는 분기형 C1-4알킬기이고 같거나 또는 다를수도 있는 R1과 R2는 수소, 할로겐 또는 C1-4알킬이다.상기식에서, R'는 알킬이다.
- 제1항에 있어서, R이 메틸, 에틸, n-프로필 또는 n-부틸인 것을 특징으로 하는 피롤로[3,2,1-hi]인돌 유도체와 제약상 허용되는 그의 산부가염을 제조하는 방법.
- 제1항에 있어서, R1과 R2는 같거나 다를수도 있는데 수소, 염소, 불소, 메틸, 에틸, n-프로필 또는 n-부틸인 것을 특징으로 하는 피롤로[3,2,1-hi]인돌 유도체와 제약상 허용되는 그의 산부가염을 제조하는 방법.
- 제1항에 있어서, 요오드이며 화합물(Ⅲ)은 용매내에서 디이소프로필아민과 부틸리듐의 존재하에 알킬화되는 것을 특징으로 하는 피롤로[3,2,1-hi]인돌 유도체와 제약상 허용되는 그의 산부가염을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8319850A FR2556345B3 (fr) | 1983-12-12 | 1983-12-12 | Derive de pyrrolo(3,2,1-hi) indole, sa preparatio n et son application en therapeutique |
| FR83/19850 | 1983-12-12 | ||
| FR19850 | 1983-12-12 | ||
| FR14839 | 1984-09-27 | ||
| FR84/14839 | 1984-09-27 | ||
| FR8414839A FR2570700B2 (fr) | 1984-09-27 | 1984-09-27 | Derives de pyrrolo-indole, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850004759A true KR850004759A (ko) | 1985-07-27 |
| KR910005851B1 KR910005851B1 (ko) | 1991-08-05 |
Family
ID=26223716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840007549A KR910005851B1 (ko) | 1983-12-12 | 1984-07-30 | 피롤로[3,2,1-hi]인돌유도체 및 약학적으로 허용되는 그의 산부가염을 제조하는 방법 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4617313A (ko) |
| EP (1) | EP0145591B1 (ko) |
| KR (1) | KR910005851B1 (ko) |
| AU (1) | AU572237B2 (ko) |
| DE (1) | DE3472259D1 (ko) |
| DK (1) | DK164670C (ko) |
| ES (1) | ES8601997A1 (ko) |
| FI (1) | FI76803C (ko) |
| GR (1) | GR81235B (ko) |
| HU (1) | HU190659B (ko) |
| IE (1) | IE57877B1 (ko) |
| IL (1) | IL73786A (ko) |
| MX (1) | MX158671A (ko) |
| NO (1) | NO162020C (ko) |
| NZ (1) | NZ210516A (ko) |
| PT (1) | PT79658B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2621486B1 (fr) * | 1987-10-07 | 1990-01-26 | Synthelabo | Utilisation de derives de pyrrolo(3,2,1-hi)indole pour obtenir un medicament destine au traitement du diabete |
| FR2611717B1 (fr) * | 1987-02-25 | 1989-05-05 | Synthelabo | Enantiomeres du (dihydro-4,5 1h-imidazolyl-2)-2 fluoro-8 tetrahydro-1,2,4,5 1h-pyrrolo(3,2,1-hi)indole, et leur application en therapeutique |
| US5643934A (en) * | 1991-03-28 | 1997-07-01 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz [CD]indoles |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE755270A (fr) * | 1969-08-27 | 1971-02-25 | Sandoz Sa | Nouveaux derives du benzo(cd)indole, leur preparation et medicaments contenant ces derives |
| DE3049405A1 (de) * | 1980-12-23 | 1982-07-15 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue derivate von antiphlogistisch wirksamen carbonsaeuren, ihre herstellung und medizinische anwendung |
| NZ201219A (en) * | 1981-07-28 | 1984-10-19 | Reckitt & Colmann Prod Ltd | Dihydrobenzofuranyl-2-imidazolines and pharmaceutical compositions |
-
1984
- 1984-07-30 KR KR1019840007549A patent/KR910005851B1/ko not_active IP Right Cessation
- 1984-12-03 EP EP84402477A patent/EP0145591B1/fr not_active Expired
- 1984-12-03 DE DE8484402477T patent/DE3472259D1/de not_active Expired
- 1984-12-10 MX MX203667A patent/MX158671A/es unknown
- 1984-12-11 NZ NZ210516A patent/NZ210516A/en unknown
- 1984-12-11 IE IE3181/84A patent/IE57877B1/en not_active IP Right Cessation
- 1984-12-11 GR GR81235A patent/GR81235B/el unknown
- 1984-12-11 NO NO844943A patent/NO162020C/no unknown
- 1984-12-11 FI FI844888A patent/FI76803C/fi not_active IP Right Cessation
- 1984-12-11 HU HU844605A patent/HU190659B/hu not_active IP Right Cessation
- 1984-12-11 AU AU36496/84A patent/AU572237B2/en not_active Ceased
- 1984-12-11 ES ES538475A patent/ES8601997A1/es not_active Expired
- 1984-12-11 DK DK590984A patent/DK164670C/da not_active IP Right Cessation
- 1984-12-11 PT PT79658A patent/PT79658B/pt not_active IP Right Cessation
- 1984-12-12 IL IL73786A patent/IL73786A/xx unknown
-
1985
- 1985-08-28 US US06/770,079 patent/US4617313A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0145591A3 (en) | 1985-10-02 |
| MX158671A (es) | 1989-02-24 |
| FI844888A0 (fi) | 1984-12-11 |
| IL73786A0 (en) | 1985-03-31 |
| NO162020C (no) | 1989-10-25 |
| US4617313A (en) | 1986-10-14 |
| FI844888L (fi) | 1985-06-13 |
| EP0145591B1 (fr) | 1988-06-22 |
| AU572237B2 (en) | 1988-05-05 |
| HUT36795A (en) | 1985-10-28 |
| KR910005851B1 (ko) | 1991-08-05 |
| FI76803C (fi) | 1988-12-12 |
| IE843181L (en) | 1985-06-12 |
| IL73786A (en) | 1987-09-16 |
| NO162020B (no) | 1989-07-17 |
| DE3472259D1 (en) | 1988-07-28 |
| DK590984D0 (da) | 1984-12-11 |
| PT79658B (fr) | 1986-12-12 |
| AU3649684A (en) | 1985-06-20 |
| DK164670B (da) | 1992-07-27 |
| ES538475A0 (es) | 1985-11-01 |
| NO844943L (no) | 1985-06-13 |
| EP0145591A2 (fr) | 1985-06-19 |
| IE57877B1 (en) | 1993-05-05 |
| ES8601997A1 (es) | 1985-11-01 |
| DK164670C (da) | 1992-12-14 |
| NZ210516A (en) | 1987-01-23 |
| DK590984A (da) | 1985-06-13 |
| GR81235B (en) | 1985-04-16 |
| HU190659B (en) | 1986-10-28 |
| FI76803B (fi) | 1988-08-31 |
| PT79658A (fr) | 1985-01-01 |
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