KR840006643A - 이소인돌 유도체의 제조방법 - Google Patents
이소인돌 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840006643A KR840006643A KR1019830005375A KR830005375A KR840006643A KR 840006643 A KR840006643 A KR 840006643A KR 1019830005375 A KR1019830005375 A KR 1019830005375A KR 830005375 A KR830005375 A KR 830005375A KR 840006643 A KR840006643 A KR 840006643A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- trifluoromethyl
- halogen
- prepare
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 4
- 125000000904 isoindolyl group Chemical class C=1(NC=C2C=CC=CC12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- -1 nitrogen amine Chemical class 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- OIXLFMOEDWMDMT-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-6-chloro-3-oxo-1h-isoindole-5-sulfonamide Chemical compound C1C=2C=C(Cl)C(S(=O)(=O)N)=CC=2C(=O)N1C(CC1)CCN1CC1=CC=CC=C1 OIXLFMOEDWMDMT-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 238000007126 N-alkylation reaction Methods 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000006264 debenzylation reaction Methods 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000011135 tin Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Suspension Of Electric Lines Or Cables (AREA)
- Liquid Developers In Electrophotography (AREA)
- Transformer Cooling (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 다음식 (Ⅱ)의 화합물 혹은 다음식(Ⅲ)의 화합물을 환원시키거나, 다음식(Ⅵ)의 화합물과 다음식(Ⅴ)의 화합물을 불활성 용매에서 반응시키거나, 다음식(Ⅳ)의 화합물과 다음식(Ⅶ)의 화합물을 반응시켜서 다음식(Ⅰ)의 화합물 혹은약리학적으로 알맞는 그 염을 제조하는 방법.상기식에서, X는 할로겐 또는 트리플루오로메틸이고, R1과 R2는 각각 수소, 저급알킬, 저급알콕시, 저급 알케닐옥시, 저급알킬티오, 트리플루오로메틸, 시아노 또는 니트로이고, Y는 1-4탄소원자를 지니는 단일 또는 이중결합 또는가지장의 알킬렌라디칼이고, R3는 아미노, 할로겐, 저급 알콕시이고, R4는 할로겐이고 CH2인 경우에 카르바모일 또는 포르밀임.
- 제1항에 있어서, 식(Ⅱ)의 화합물 또는 식(Ⅲ)의 화합물의 환원이 아연, 초산,주석 및 진한 염산의 존재하에 고온으로 60-150℃의 온도로 6-48시간 불활성 유기용매에서 행하는 방법.
- 제1항에 있어서 둘째단계를 사용하는 방법.
- 제1항에 있어서 화합물(Ⅳ)와 (Ⅶ)의 화합물의 반응이 불활성유기 용매에서 고온으로 50-200℃온도에서 염기성 축합제 혹은 유기 사차 질소아민 염기의 존재하에 반응시키는 방법.
- 제1항의 화합물 혹은 그의 산부가염을 포유류 체중의 10㎏당 약 0.05-500㎎의 범위로 약리학적으로 알맞는 담체와 혼합제조하는 포유류 투여에 알맞는 조성물.
- 다음식(Ⅱ)의 화합물을 초산에서 과량아연의 존재하에 100℃이하, 특히 실온근처에서 환원시키는 것으로 구성되는 다음식(Ⅲ)의 화합물을 제조하는 방법.상기식에서, X는 할로겐 또는 트리플루오로 메틸이고, R1와 R2는 각기 수소, 저급알킬, 저급알콕시, 저급 알케닐옥시, 저급 알킬티오, 트리플루오로메틸, 시아노, 또는 니트로이고, Y는 1-4탄소원자의 단일 혹은 이가 직쇄 혹은 가지상 알킬렌라디칼이고,
- 다음식(Ⅷ)의 화합물과 아미노 보호기, 예를들어, -부톡시카르보닐 아지드 또는3-t-부틸 피토카르보내이트와 접촉시켜서 다음식(Ⅸ)의 화합물을 제조하고, 이화합물을 접촉 탈벤질화하여서 아음식(Ⅹ)의 화합물을 제조하고, 이 화합물을 페닐알킬 헬라이드로 N-알킬화하여서 다음식(Ⅸ)를 제조하고,상기 보호기를 F3COO2H로 처리하여 제거하여 다음식(XII)의 화합물을 제조하는 단계로 구성되는 다음식(Ⅳ)의 화합물을 제조하는 방법.상기식에서, R1과 R2는 각기 수소, 저급알킬, 저급 알콕시, 저급 알케닐옥시, 저급알킬티오, 트리플루오로메틸, 시아노, 또는 니트로이고, Y는 1-4탄소원자의 단일 또는 이가 직쇄 또는 가지상 알킬렌라디칼이고, t는 t-부틸임.
- 제1항에 있어서, 식(Ⅰ)의 항고혈압양 또는 약리적으로 알맞는 산부가염 또는 약리학적으로 알맞는 담체로 구성되는 제약학적 조성물.
- 제8항에 있어서 화합물이 6-클로로-2,3-디히드로-3-옥소-2-〔1-(페닐메틸)-4피페리디닐〕-1H-이소인돌-5-설폰아미드인 조성물.
- 제8항에 있어서 화합물이 6-클로로-2,3-디히드로-3-옥소-2-〔1-(페닐메틸)-4피페리디닐〕-1H-이소인돌-설폰아미드 염화물인 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019870004127A KR880001735B1 (ko) | 1982-11-12 | 1987-04-27 | 이소인돌 유도체 및 그것의 제조방법 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US441,204 | 1982-11-12 | ||
| US06/441,204 US4495194A (en) | 1982-11-12 | 1982-11-12 | Antihypertensive isoindole derivatives |
| US441204 | 1982-11-12 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019870004127A Division KR880001735B1 (ko) | 1982-11-12 | 1987-04-27 | 이소인돌 유도체 및 그것의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840006643A true KR840006643A (ko) | 1984-12-01 |
| KR870001168B1 KR870001168B1 (ko) | 1987-06-15 |
Family
ID=23751955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830005375A KR870001168B1 (ko) | 1982-11-12 | 1983-11-12 | 이소인돌 유도체의 제조방법 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4495194A (ko) |
| EP (1) | EP0111397B1 (ko) |
| JP (2) | JPS59101483A (ko) |
| KR (1) | KR870001168B1 (ko) |
| AT (1) | ATE40999T1 (ko) |
| AU (2) | AU566900B2 (ko) |
| CA (1) | CA1246081A (ko) |
| DE (1) | DE3379267D1 (ko) |
| DK (2) | DK165116C (ko) |
| ES (5) | ES527146A0 (ko) |
| FI (1) | FI82691C (ko) |
| GR (1) | GR81279B (ko) |
| IE (1) | IE56231B1 (ko) |
| PT (1) | PT77651B (ko) |
| ZA (1) | ZA838361B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU636164B2 (en) * | 1982-11-12 | 1993-04-22 | Bristol-Myers Squibb Company | 2,3-dihydro-1-hydroxy-3-oxo-2-(1-substituted-4-piperidinyl)- 1N-isoindole derivatives |
| EP0351283A1 (fr) * | 1988-07-12 | 1990-01-17 | Synthelabo | Dérivés de [(pipéridinyl-4) méthyl]-2 dihydro-2,3 1H-isoindole et tétrahydro-2,3,4,5 1H-benzazépines, leur préparation et leur application en thérapeutique |
| US5356906A (en) * | 1989-10-27 | 1994-10-18 | The Du Pont Merck Pharmaceutical Company | (N-phthalimidoalkyl) piperidines useful as treatments for psychosis |
| WO1991006297A1 (en) * | 1989-10-27 | 1991-05-16 | The Du Pont Merck Pharmaceutical Company | (n-phthalimidoalkyl) piperidines |
| JP2807577B2 (ja) * | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | 環状アミド誘導体 |
| ES2291293T3 (es) * | 2000-02-29 | 2008-03-01 | Mitsubishi Pharma Corporation | Nuevos derivados amida ciclicos. |
| US8939859B2 (en) | 2012-10-19 | 2015-01-27 | Caterpillar Inc. | Torque converter with stator clutch |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3579524A (en) * | 1968-06-05 | 1971-05-18 | Miles Lab | 2-aminoalkyl derivatives of phthalimidines |
| GB1486104A (en) * | 1975-01-23 | 1977-09-21 | Wyeth John & Brother Ltd | Phthalimidopiperidine derivatives |
| IL52413A (en) * | 1977-06-29 | 1980-01-31 | Teva Pharma | Process for the preparazione of 5-chloro-6-sulfamyl-isoindolinone derivatives |
| SE7907121L (sv) * | 1979-08-27 | 1981-02-28 | Astra Laekemedel Ab | Ftalimidinderivat |
-
1982
- 1982-11-12 US US06/441,204 patent/US4495194A/en not_active Expired - Fee Related
-
1983
- 1983-11-09 CA CA000440844A patent/CA1246081A/en not_active Expired
- 1983-11-09 ZA ZA838361A patent/ZA838361B/xx unknown
- 1983-11-09 GR GR72928A patent/GR81279B/el unknown
- 1983-11-09 FI FI834112A patent/FI82691C/fi not_active IP Right Cessation
- 1983-11-10 ES ES527146A patent/ES527146A0/es active Granted
- 1983-11-11 JP JP58211113A patent/JPS59101483A/ja active Granted
- 1983-11-11 DE DE8383306911T patent/DE3379267D1/de not_active Expired
- 1983-11-11 AU AU21183/83A patent/AU566900B2/en not_active Ceased
- 1983-11-11 AT AT83306911T patent/ATE40999T1/de active
- 1983-11-11 PT PT77651A patent/PT77651B/pt not_active IP Right Cessation
- 1983-11-11 DK DK517383A patent/DK165116C/da not_active IP Right Cessation
- 1983-11-11 IE IE2638/83A patent/IE56231B1/en not_active IP Right Cessation
- 1983-11-11 EP EP83306911A patent/EP0111397B1/en not_active Expired
- 1983-11-12 KR KR1019830005375A patent/KR870001168B1/ko not_active IP Right Cessation
-
1984
- 1984-07-02 ES ES533939A patent/ES8600743A1/es not_active Expired
- 1984-07-02 ES ES533936A patent/ES8600740A1/es not_active Expired
- 1984-07-02 ES ES533937A patent/ES8600741A1/es not_active Expired
- 1984-07-02 ES ES533938A patent/ES533938A0/es active Granted
-
1987
- 1987-10-05 AU AU79369/87A patent/AU604756B2/en not_active Ceased
-
1990
- 1990-06-22 DK DK153690A patent/DK153690D0/da not_active IP Right Cessation
-
1991
- 1991-10-30 JP JP3310030A patent/JPH051058A/ja active Granted
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