KR850001749A - 인돌유도체의 제조방법 - Google Patents
인돌유도체의 제조방법 Download PDFInfo
- Publication number
- KR850001749A KR850001749A KR1019840004683A KR840004683A KR850001749A KR 850001749 A KR850001749 A KR 850001749A KR 1019840004683 A KR1019840004683 A KR 1019840004683A KR 840004683 A KR840004683 A KR 840004683A KR 850001749 A KR850001749 A KR 850001749A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- group
- iii
- general formula
- hydrogen atom
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- -1 methoxyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 238000005937 allylation reaction Methods 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [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
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Orthopedics, Nursing, And Contraception (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (2)
- (ⅰ) 다음 일반식(Ⅱ)의 에스테르를 화합물 R1X의 반응시켜서 다음 일반식(Ⅲ)의 화합물을 얻고, 부틸리튬과 디이소푸로필아민의 존재하에 할로겐화물 R2'Y와 반응시킴으로써 화합물(Ⅲ)을 알킬화 또는 알릴화시켜 다음 일반식(Ⅳ)의 화합물을 얻고, 이것을 트리메틸 알루미늄의 존재하에 에틸렌디아민과 반응시킴으로써 화합물(Ⅲ)이나 화합물(Ⅳ)를 R1이 수소원자 이외의것인 일반식(Ⅰ)의 화합물로 전환시키고, 요구에 따라서는 상기 화합물(Ⅰ)을 약학적으로 사용가능한 염으로 전환시키고,상기식들에서R1은 수소원자, 직쇄나 측쇄의 (C1-6)아킬기, (C3-6)씨클로알킬-(C1-4)알킬기, (C2-6)알케닐기, 나프틸메틸기, 1개이상의 할로겐 원자나 메틸로 선택적으로 치환된 펜에틸기나 벤질기, 메톡실기 또는 메틸렌디옥시기이고,R2는 H 또는 (C1-4)알킬 또는 알릴기이며,R'는 (C1-4)알킬기이고,R1X에서 R1은 위에서 정의한 바와 같으나 수소원자는 아니며,R'2Y에서 R'2는 (C1-4)알킬 또는 알릴기이며,X와 Y는 가변성 기이다. 또는(ⅱ) 다음 일반식(Ⅴ)의 화합물을 탈벤질화시키고, R1이 수소원자인 이와같이 얻은 화합물(Ⅴ)를 트리메틸 알루미늄의 존재하에 에틸렌디아민과 반응시킴으로써 R1이 수소인 화합물(Ⅰ)로 전환시키고, 요구에 따라서는 상기 화합물(Ⅰ)을 약학적으로 사용가능한 염으로 전환시키고,상기식에서R1은 벤질기이고,R2는 위에서 정의한 것과 같으며,R'는 (C1-4)알킬기이다. 또는(ⅲ) R1이 벤질기인 화합물(Ⅰ)을 탈벤질화시키고, 요구에 따라서는 이와같이 얻은 R1이 수소원자인 화합물(Ⅰ)을 약학적으로 사용가능한 염으로 전환시킴을 특징으로하는, 라세미체나 광학활성이성체의 형태로 다음 일반식(Ⅰ)의 인돌유도체를 제조하는 방법.
- 제1항에 있어서, 공정(ⅰ)의 일반식(Ⅱ)인 에스테르의 R1이 할로겐원자나 메틸기로 선택 치환된 벤질이거나 메틸렌디옥시기이거나 또는 알릴기, 또는 (C1-4)알킬기이며, 화합물(Ⅲ)은 선택적인 알킬화나 알릴화 반응없이 화합물(Ⅰ)로 전환되는 것을 특징으로 하는 인돌유도체의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR13198 | 1983-08-11 | ||
| FR8313198A FR2550532B1 (fr) | 1983-08-11 | 1983-08-11 | Derives de l'indole, leur preparation et leur application en therapeutique |
| FR16473 | 1983-10-17 | ||
| FR8316473A FR2553415B2 (fr) | 1983-10-17 | 1983-10-17 | Derives de l'indole, leur preparation et leur application en therapeutique |
| FR18121 | 1983-11-15 | ||
| FR8318121A FR2554815A2 (fr) | 1983-11-15 | 1983-11-15 | Derives de l'indole, leur preparation et leur application en therapeutique |
| FR01998 | 1984-02-09 | ||
| FR8401998A FR2559482A2 (fr) | 1984-02-09 | 1984-02-09 | Derives de l'indole, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR850001749A true KR850001749A (ko) | 1985-04-01 |
Family
ID=27446455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004683A KR850001749A (ko) | 1983-08-11 | 1984-08-07 | 인돌유도체의 제조방법 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4598086A (ko) |
| EP (1) | EP0141686B1 (ko) |
| KR (1) | KR850001749A (ko) |
| AT (1) | ATE29494T1 (ko) |
| AU (1) | AU563559B2 (ko) |
| CA (1) | CA1236464A (ko) |
| DE (1) | DE3465993D1 (ko) |
| DK (1) | DK385984A (ko) |
| ES (1) | ES8602771A1 (ko) |
| FI (1) | FI843155A (ko) |
| GR (1) | GR80101B (ko) |
| HU (1) | HU192416B (ko) |
| IL (1) | IL72647A0 (ko) |
| NO (1) | NO843203L (ko) |
| NZ (1) | NZ209174A (ko) |
| PT (1) | PT79067B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0211698B1 (fr) * | 1985-02-08 | 1991-01-30 | Synthelabo | Dérivés de (dihydro-4,5 1H-imidazolyl-2)-2 dihydro-2,3 indole, leur préparation et leur application en thérapeutique |
| US4908376A (en) * | 1985-09-03 | 1990-03-13 | Ciba-Geigy Corporation | 2,3-dihydro-2-(4,5-dihydroimidazol-2-yl)-indoles in composition form for reducing intraocular pressure |
| US4912125A (en) * | 1985-09-03 | 1990-03-27 | Ciba-Geigy Corporation | 2,3-dihydro-2-(4,5-dihydroimidazol-2-yl)-indoles for reducing intraocular pressure |
| GB9022858D0 (en) * | 1990-10-20 | 1990-12-05 | Reckitt & Colmann Prod Ltd | Derivatives of indoles |
| US20020006469A1 (en) * | 1996-08-14 | 2002-01-17 | Gilles Baillet | Method for incorporating additives in an ophthalmic article by means of a supercritical fluid |
| AU2201699A (en) * | 1997-12-19 | 1999-07-12 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| BRPI0618523A2 (pt) * | 2005-11-11 | 2011-09-06 | Hoffmann La Roche | compostos de aminas cìclicas fundidas carbocìclicas, composições farmacêuticas e usos dos mesmos |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2358890A1 (fr) * | 1976-05-24 | 1978-02-17 | Science Union & Cie | Nouvelles aryl trifluoroethylamines, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
| US4378357A (en) * | 1977-02-03 | 1983-03-29 | Rohm And Haas Company | Novel heterocyclic compounds |
| FI800519A (fi) * | 1979-02-22 | 1980-08-23 | Wellcome Found | Imidazolderivat och salter daerav syntes av dessa och farmaceutiska preparat innehaollande dessa |
| US4280327A (en) * | 1979-04-30 | 1981-07-28 | The Garrett Corporation | Solar powered turbine system |
| 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 |
| DE3141063A1 (de) * | 1981-10-13 | 1983-04-28 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue imidazol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
-
1984
- 1984-07-30 AT AT84401595T patent/ATE29494T1/de not_active IP Right Cessation
- 1984-07-30 EP EP84401595A patent/EP0141686B1/fr not_active Expired
- 1984-07-30 DE DE8484401595T patent/DE3465993D1/de not_active Expired
- 1984-08-07 KR KR1019840004683A patent/KR850001749A/ko not_active Application Discontinuation
- 1984-08-10 NO NO843203A patent/NO843203L/no unknown
- 1984-08-10 NZ NZ209174A patent/NZ209174A/en unknown
- 1984-08-10 FI FI843155A patent/FI843155A/fi not_active Application Discontinuation
- 1984-08-10 HU HU843066A patent/HU192416B/hu not_active IP Right Cessation
- 1984-08-10 CA CA000460777A patent/CA1236464A/en not_active Expired
- 1984-08-10 US US06/639,323 patent/US4598086A/en not_active Expired - Fee Related
- 1984-08-10 AU AU31802/84A patent/AU563559B2/en not_active Ceased
- 1984-08-10 GR GR80101A patent/GR80101B/el unknown
- 1984-08-10 DK DK385984A patent/DK385984A/da not_active Application Discontinuation
- 1984-08-10 PT PT79067A patent/PT79067B/pt not_active IP Right Cessation
- 1984-08-10 ES ES535062A patent/ES8602771A1/es not_active Expired
- 1984-08-10 IL IL72647A patent/IL72647A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT79067B (fr) | 1986-11-14 |
| DE3465993D1 (en) | 1987-10-15 |
| ES535062A0 (es) | 1985-12-01 |
| NO843203L (no) | 1985-02-12 |
| GR80101B (en) | 1984-12-14 |
| EP0141686B1 (fr) | 1987-09-09 |
| EP0141686A1 (fr) | 1985-05-15 |
| HUT35670A (en) | 1985-07-29 |
| US4598086A (en) | 1986-07-01 |
| CA1236464A (en) | 1988-05-10 |
| ES8602771A1 (es) | 1985-12-01 |
| ATE29494T1 (de) | 1987-09-15 |
| AU563559B2 (en) | 1987-07-16 |
| FI843155A0 (fi) | 1984-08-10 |
| DK385984A (da) | 1985-02-12 |
| FI843155A (fi) | 1985-02-12 |
| AU3180284A (en) | 1985-02-14 |
| DK385984D0 (da) | 1984-08-10 |
| HU192416B (en) | 1987-06-29 |
| IL72647A0 (en) | 1984-11-30 |
| PT79067A (fr) | 1984-09-01 |
| NZ209174A (en) | 1986-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |