KR840002002A - 옥사졸리딘디온 유도체의 제조방법 - Google Patents
옥사졸리딘디온 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840002002A KR840002002A KR1019820004569A KR820004569A KR840002002A KR 840002002 A KR840002002 A KR 840002002A KR 1019820004569 A KR1019820004569 A KR 1019820004569A KR 820004569 A KR820004569 A KR 820004569A KR 840002002 A KR840002002 A KR 840002002A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- spiro
- hydrogen
- oxindole
- oxazolidinedione
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- 150000001475 oxazolidinediones Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- -1 hydroxy ester Chemical class 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000012467 final product Substances 0.000 claims 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims 2
- COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- DDAHQEVSRQGJLD-UHFFFAOYSA-N C1C2(CN(C3=C2C=C(C=C3)Cl)CC4=CC=C(C=C4)Cl)OCN1 Chemical group C1C2(CN(C3=C2C=C(C=C3)Cl)CC4=CC=C(C=C4)Cl)OCN1 DDAHQEVSRQGJLD-UHFFFAOYSA-N 0.000 claims 1
- IZMZSYGAMQKJQT-UHFFFAOYSA-N CN1CC2(CNCO2)C2=CC(=CC=C12)Cl Chemical compound CN1CC2(CNCO2)C2=CC(=CC=C12)Cl IZMZSYGAMQKJQT-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (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 (7)
- (a) 다음 일반식(B)의 적절히 치환된 이사틴 출발물질을 저급 시안화 트리알킬실릴과 반응시켜 대응하는 3-시아노-3-트리알킬실릴옥시 유도체를 생성시키고, 이어서 이 유도체를 알콜성 염화수소로 처리하여 목적하는 히드록시 에스테르를 얻고, (b) 이 에스테르를 테트라히드로푸란 중에서 클로로술포닐이소시안산염과 반응시킨 다음, 이어서 환원성 가수분해시켜서 대응하는 우레탄 에스테르를 얻고, (c) 이 에스테르를 비산성 조건하에 순환시켜 다음 일반식(A)의 소정의 스피로-옥신돌 옥사졸리딘디온 최종 생성물을 얻고, 필요에 따라서 이 스피로-옥신돌 옥사졸리딘디온 최종생성물을 약리학적으로 허용 가능한 그들의 염기로 전화시키는 것을 특징으로 하는 다음 일반식(A)의 스피로-옥신돌옥사졸리딘디온 유도체 및 약리학적으로 허용 가능한 양이온으로 이루어진 이들의 염기성염을 제조하는 방법.상기 일반식에서, X와 Y는 각각 수소, 불소, 염소, 브롬, 니트로기 또는 아미노기이며, Z는 수소 또는 아미노기이며, 단 X와 Y중 어느하나가 수소가 아닐 경우에 Z는 수소이며, R는 수소, 탄소원자 1-4인 알킬기, 아릴기 또는 탄소원자 1-3개를 갖는 알킬기로 이루어진 아릴알킬기, 여기서 각각의 아릴기는 나프틸기, 피리딜기, 푸릴기, 티엔일기, 페닐기, 일치환페닐기 또는 이치환페닐기이며, 각각의 고리치환체는 봉소, 염소, 브롬, 탄소원자 1-4개를 갖는 알킬기, 탄소원자 1-4개를 갖는 알콕시기 또는 트리플루오로메틸기이며, 단 상기 X,Y 및 Z 각각이 수소일 경우 상기 R는 항상 수소 또는 알킬기 또는 페닐알킬기가 아닌 다른 기이다.
- 제1항에 있어서, 단계(c)의 순환반응을 강한 염기성 촉매의 존재하 반응 불활성 유기 용매 내에서 수행함을 특징으로 하는 제조방법.
- 제2항에 있어서, 상기 용매가 디메틸포름아미드이며 상기 염기성 촉매가 3급 부톡시 칼륨임을 특징으로 하는 제조방법.
- 제1항에 있어서, 제조된 스피로-옥신돌 옥사졸리딘디온 유도체가 1-(p-플루오로페닐)-5-플루오로-스피로-[인돌린-3,5'-옥사졸리딘]-2,2',4'-트리온임을 특징으로 하는 제조방법.
- 제1항에 있어서, 제조된 스피로-옥신돌 옥사졸리딘디온 유도체가 1-메틸-5-클로로-스피로-[인돌린-3,5'-옥사졸리딘]-2,2',4'-트리온임을 특징으로 하는 제조방법.
- 제1항에 있어서, 제조된 스피로-옥신돌 옥사졸리딘디온 유도체가 1-이소프로필-5-클로로-TVL로-[인돌린-3,5-옥사졸리딘]-2,2',4,-트리온임을 특징으로 하는 제조방법.
- 제1항에 있어서, 제조된 스피로-옥신돌 옥사졸리딘디온 유도체가 1-(p-클로로벤질)-5-클로로-스피로-[인돌린-3,5'-옥사졸리딘]-2,2',4'-트리온임을 특징으로 하는 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31068281A | 1981-10-13 | 1981-10-13 | |
| US310682 | 1981-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840002002A true KR840002002A (ko) | 1984-06-11 |
| KR860000486B1 KR860000486B1 (ko) | 1986-04-30 |
Family
ID=23203647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8204569A KR860000486B1 (ko) | 1981-10-13 | 1982-10-11 | 옥사졸리딘디온 유도체의 제조 방법 |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0079675A1 (ko) |
| JP (1) | JPS5877883A (ko) |
| KR (1) | KR860000486B1 (ko) |
| AR (1) | AR231839A1 (ko) |
| AU (1) | AU531161B2 (ko) |
| CA (1) | CA1171860A (ko) |
| DK (1) | DK449882A (ko) |
| ES (1) | ES515751A0 (ko) |
| FI (1) | FI823480L (ko) |
| GR (1) | GR77019B (ko) |
| HU (1) | HU185113B (ko) |
| IL (1) | IL66954A (ko) |
| PH (1) | PH18038A (ko) |
| PL (1) | PL238595A1 (ko) |
| PT (1) | PT75673B (ko) |
| YU (1) | YU229382A (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA832679B (en) * | 1982-05-07 | 1983-12-28 | Ici Plc | Indoline derivatives |
| EP0159143B1 (en) * | 1984-03-23 | 1987-12-16 | Pfizer Inc. | Spiro-indenes and spiro-1,2-dihydro-naphthalenes for treatment of diabetic complications |
| HU203330B (en) * | 1987-06-10 | 1991-07-29 | Pfizer | Process for producing oxazolidin-2-one derivatives and hypoglychemic pharmaceutical compositions containing them |
| AU617541B2 (en) * | 1988-10-20 | 1991-11-28 | Wyeth | Spiro-isoquinoline-pyrrolidine tetrones and analogs thereof useful as aldose reductase inhibitors |
| US5221686A (en) * | 1992-08-04 | 1993-06-22 | American Home Products Corporation | Spiro[1,2-benzisothiazole-3(2H),5'-oxazolidine]-2',4'-dione 1,1-dioxides as antihyperglycemic agents |
| FR2708606B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| CN102336769A (zh) * | 2011-07-06 | 2012-02-01 | 华东理工大学 | 一种简便的合成螺[氧化吲哚-3,5＇-噁唑啉]杂环化合物的新方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200642A (en) * | 1978-08-21 | 1980-04-29 | Pfizer Inc. | Spiro-oxazolidindiones |
-
1982
- 1982-09-16 ES ES515751A patent/ES515751A0/es active Granted
- 1982-10-08 EP EP82305385A patent/EP0079675A1/en not_active Withdrawn
- 1982-10-11 IL IL66954A patent/IL66954A/xx unknown
- 1982-10-11 KR KR8204569A patent/KR860000486B1/ko active
- 1982-10-11 YU YU02293/82A patent/YU229382A/xx unknown
- 1982-10-11 GR GR69495A patent/GR77019B/el unknown
- 1982-10-11 AR AR290934A patent/AR231839A1/es active
- 1982-10-12 PH PH27974A patent/PH18038A/en unknown
- 1982-10-12 CA CA000413239A patent/CA1171860A/en not_active Expired
- 1982-10-12 AU AU89288/82A patent/AU531161B2/en not_active Ceased
- 1982-10-12 DK DK449882A patent/DK449882A/da not_active Application Discontinuation
- 1982-10-12 FI FI823480A patent/FI823480L/fi not_active Application Discontinuation
- 1982-10-12 PL PL23859582A patent/PL238595A1/xx unknown
- 1982-10-12 PT PT75673A patent/PT75673B/pt unknown
- 1982-10-12 HU HU823246A patent/HU185113B/hu unknown
- 1982-10-13 JP JP57179684A patent/JPS5877883A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| YU229382A (en) | 1984-12-31 |
| PT75673B (en) | 1985-12-09 |
| IL66954A0 (en) | 1983-02-23 |
| PT75673A (en) | 1982-11-01 |
| ES8400116A1 (es) | 1983-10-16 |
| IL66954A (en) | 1985-02-28 |
| FI823480A0 (fi) | 1982-10-12 |
| AR231839A1 (es) | 1985-03-29 |
| PH18038A (en) | 1985-03-08 |
| HU185113B (en) | 1984-12-28 |
| JPS5877883A (ja) | 1983-05-11 |
| PL238595A1 (en) | 1983-09-12 |
| JPS611073B2 (ko) | 1986-01-13 |
| AU531161B2 (en) | 1983-08-11 |
| ES515751A0 (es) | 1983-10-16 |
| AU8928882A (en) | 1983-04-21 |
| EP0079675A1 (en) | 1983-05-25 |
| GR77019B (ko) | 1984-09-04 |
| DK449882A (da) | 1983-04-14 |
| CA1171860A (en) | 1984-07-31 |
| KR860000486B1 (ko) | 1986-04-30 |
| FI823480L (fi) | 1983-04-14 |
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