KR840007223A - 5-(2-알콕시페닐) 티아졸리딘디온의 제조방법 - Google Patents
5-(2-알콕시페닐) 티아졸리딘디온의 제조방법 Download PDFInfo
- Publication number
- KR840007223A KR840007223A KR1019840000150A KR840000150A KR840007223A KR 840007223 A KR840007223 A KR 840007223A KR 1019840000150 A KR1019840000150 A KR 1019840000150A KR 840000150 A KR840000150 A KR 840000150A KR 840007223 A KR840007223 A KR 840007223A
- Authority
- KR
- South Korea
- Prior art keywords
- chloro
- hydrogen
- methyl
- alkoxyphenyl
- fluoro
- Prior art date
Links
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 title 1
- 229940123464 Thiazolidinedione Drugs 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000011260 aqueous acid Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- HYMJHROUVPWYNQ-UHFFFAOYSA-N 2-amino-1,3-thiazol-4-one Chemical compound NC1=NC(=O)CS1 HYMJHROUVPWYNQ-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- -1 aryl thiazolidinedione derivative Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
-
- 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
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/34—Oxygen atoms
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Paints Or Removers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 일반식(Ⅲ)의 알파-(2-알콕시페닐)-알파-클로로아세트산 알킬에스페르를 적어도 75℃의 온도에서 반응-불활성 용매중에 티오우레아와 반응시키고, 생성된 5-(2-알콕시페닐)-2-이미노티아졸리딘-4-온을 희 수성산으로 가수분해 시킴을 특징으로하여 일반식(Ⅳ)의 아릴 티아졸리딘디온 유도체 및 그의 약학적으로 무독한 양이온과의 염기염을 제조하는 방법.상기식에서, R은 탄소수 1 내지 4의 알킬이고, X는 플루오로, 클로로 또는 브로모이며, Y는 수소 클로로, 저급알킬 또는 저급알콕시이고, R1은 (C1-4) 알킬이다.
- 제1항에 있어서, 반응-불활성 용매가 에탄올, 이소프로판을 또는 설포란인 방법.
- 제1항에 있어서, 희 수성산이 희염산인 방법.
- 제2항에 있어서, X가 플루오로이고, Y가 수소인 방법.
- 제4항에 있어서, R이 메틸이고, Y가 수소이며, X가 6-플루오로인 방법.
- 제2항에 있어서, X가 클로로이고, Y가 수소인 방법.
- 제6항에 있어서, R이 메틸이고, Y가 수소이며, X가 6-클로로인 방법.
- 제6항에 있어서, R이 메틸이고, Y가 수소이며, X가 5-클로로인 방법.
- 제2항에 있어서, R이 메틸이고, Y가 3-메틸이며, X가 5-클로로인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45868483A | 1983-01-17 | 1983-01-17 | |
| US458,684 | 1983-01-17 | ||
| US458684 | 1983-01-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840007223A true KR840007223A (ko) | 1984-12-06 |
| KR870001267B1 KR870001267B1 (ko) | 1987-06-30 |
Family
ID=23821708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840000150A KR870001267B1 (ko) | 1983-01-17 | 1984-01-16 | 5-(2-알콕시페닐)티아졸 리딘디온의 제조방법 |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP0117035B1 (ko) |
| JP (1) | JPS59137474A (ko) |
| KR (1) | KR870001267B1 (ko) |
| AT (1) | ATE45574T1 (ko) |
| AU (1) | AU539921B2 (ko) |
| CA (1) | CA1233470A (ko) |
| CS (1) | CS241149B2 (ko) |
| DD (1) | DD216012A5 (ko) |
| DE (1) | DE3479419D1 (ko) |
| DK (1) | DK17984A (ko) |
| EG (1) | EG16563A (ko) |
| ES (1) | ES528887A0 (ko) |
| FI (1) | FI840155A (ko) |
| GR (1) | GR79763B (ko) |
| GT (1) | GT198400006A (ko) |
| HU (1) | HU191265B (ko) |
| IE (1) | IE56842B1 (ko) |
| IL (1) | IL70690A (ko) |
| NO (1) | NO162462C (ko) |
| NZ (1) | NZ206845A (ko) |
| PH (1) | PH18882A (ko) |
| PL (1) | PL142152B1 (ko) |
| PT (1) | PT77958B (ko) |
| SU (1) | SU1189341A3 (ko) |
| YU (1) | YU43336B (ko) |
| ZA (1) | ZA84305B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU210339B (en) | 1985-05-21 | 1995-03-28 | Pfizer | Process for preparing thiazolidinediones and their pharmaceutical compositions haring hypoglycemic effect |
| GB8910639D0 (en) * | 1989-05-09 | 1989-06-21 | Beecham Group Plc | Novel compounds |
| JPH04210683A (ja) * | 1990-12-06 | 1992-07-31 | Terumo Corp | チアゾリジン−２，４−ジオン誘導体およびこれを含有する糖尿病合併症治療薬 |
| JP3053490B2 (ja) * | 1991-02-25 | 2000-06-19 | 杏林製薬株式会社 | チアゾリジン−２，４−ジオン誘導体とその塩及び製造法 |
| CA3053956C (en) * | 2017-03-03 | 2024-04-23 | Gilead Sciences, Inc. | Processes for preparing acc inhibitors and solid forms thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2263296A1 (de) * | 1972-12-23 | 1974-06-27 | Bayer Ag | 4-alkyl-thiazol-2-one, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| AU6610081A (en) * | 1980-01-24 | 1981-07-30 | Senju Pharmaceutical Co., Ltd. | Thiazolidine derivatives |
| JPS56104876A (en) * | 1980-01-24 | 1981-08-20 | Takeda Chem Ind Ltd | Thiazolidine derivative |
| JPS5728075A (en) * | 1980-07-29 | 1982-02-15 | Takeda Chem Ind Ltd | Thiazolidine derivative |
| JPS5728073A (en) * | 1980-07-29 | 1982-02-15 | Takeda Chem Ind Ltd | Inhibitor for aldose reducing enzyme |
| JPS57123175A (en) * | 1981-01-26 | 1982-07-31 | Takeda Chem Ind Ltd | Preparation of thiazolidine derivative |
-
1984
- 1984-01-11 AT AT84300155T patent/ATE45574T1/de active
- 1984-01-11 EP EP84300155A patent/EP0117035B1/en not_active Expired
- 1984-01-11 DE DE8484300155T patent/DE3479419D1/de not_active Expired
- 1984-01-12 GR GR73500A patent/GR79763B/el unknown
- 1984-01-13 PT PT77958A patent/PT77958B/pt unknown
- 1984-01-13 GT GT198400006A patent/GT198400006A/es unknown
- 1984-01-13 CA CA000445291A patent/CA1233470A/en not_active Expired
- 1984-01-16 KR KR1019840000150A patent/KR870001267B1/ko not_active IP Right Cessation
- 1984-01-16 FI FI840155A patent/FI840155A/fi not_active Application Discontinuation
- 1984-01-16 YU YU61/84A patent/YU43336B/xx unknown
- 1984-01-16 SU SU843692005A patent/SU1189341A3/ru active
- 1984-01-16 ES ES528887A patent/ES528887A0/es active Granted
- 1984-01-16 NO NO840144A patent/NO162462C/no unknown
- 1984-01-16 PL PL1984245745A patent/PL142152B1/pl unknown
- 1984-01-16 DK DK17984A patent/DK17984A/da not_active Application Discontinuation
- 1984-01-16 HU HU84149A patent/HU191265B/hu unknown
- 1984-01-16 NZ NZ206845A patent/NZ206845A/en unknown
- 1984-01-16 AU AU23287/84A patent/AU539921B2/en not_active Ceased
- 1984-01-16 IL IL70690A patent/IL70690A/xx unknown
- 1984-01-16 DD DD84259419A patent/DD216012A5/de unknown
- 1984-01-16 ZA ZA84305A patent/ZA84305B/xx unknown
- 1984-01-16 IE IE79/84A patent/IE56842B1/en not_active IP Right Cessation
- 1984-01-17 PH PH30115A patent/PH18882A/en unknown
- 1984-01-17 JP JP59006217A patent/JPS59137474A/ja active Granted
- 1984-01-17 EG EG32/84A patent/EG16563A/xx active
- 1984-01-17 CS CS84385A patent/CS241149B2/cs unknown
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