KR830006247A - 5-치환된 옥사졸리딘-2,4-디온의 제조방법 - Google Patents
5-치환된 옥사졸리딘-2,4-디온의 제조방법 Download PDFInfo
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- KR830006247A KR830006247A KR1019810002716A KR810002716A KR830006247A KR 830006247 A KR830006247 A KR 830006247A KR 1019810002716 A KR1019810002716 A KR 1019810002716A KR 810002716 A KR810002716 A KR 810002716A KR 830006247 A KR830006247 A KR 830006247A
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- fluoro
- chloro
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- -1 5-substituted oxazolidine-2,4-dione Chemical class 0.000 title claims 9
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 230000003301 hydrolyzing effect Effects 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 239000012442 inert solvent Substances 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 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
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
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- 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
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- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
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- 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
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
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- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
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Claims (1)
- (a) 포스겐을 불활성 용매내에서 다음 구조식(Ⅱ)의 화합물과 반응시켜 구조식(Ⅲ)의 화합물을 형성시키고 이 구조식(Ⅲ)의 화합물을 분리하거나 분리되지 않는 채로 가수분해하여 구조식(Ⅳ)의 화합물을 제조하고 또는상기 구조식에서R2는 (C1∼C3) 알킬R6는여기서, W는 플루오로,W1는 벤질옥시, 클로로, 페녹시, 니트로 또는 트리플루오로메틸.W2는 벤질옥시, 페녹시, 니트로 또는 트리플루오로메틸.W3는 메틸, (C1∼C3) 알콕시, 메틸티오, 클로로 또는 플루오로W4및 W4는 각각 독립적으로 수소, 메틸, 브로모, 클로로, 플루오로, 시아노, 니트로 또는 트리플루오로메틸,Y, Y1및 Y2는 하기에서와 같고(b) 반응불활성용매내에서, 알킬 클로로포르메이트를 약염기 존재하에 구조식(Ⅴ) 화합물과 반응시키거나 디알킬카보네이트를 강겸기 존재하에 구조식(Ⅴ)화합물과 반응시켜 구조식(Ⅳ)의 화합물을 제조하고,또는상기 구조식에서 R6는 상기에서와 같고,(c) 우레아 또는 우레탄을 반응 불활성 용매 중에서 강염기 존재하에 구조식(Ⅵ) 또는 (Ⅶ)에 에스테르와 반응시켜 구조식(Ⅷ)의 화합물을 제조하고, 또는상기 구조식에서 R1및 R2는 하기에서와 같고,(d) 구조식(Ⅸ)의 티오화합물을 산화하여 구조식(Ⅳ)의 화합물로 만들고 또는상기 구조식에서 R6는 상기에서와 같고,(e) 구조식(Ⅹ)의 티오화합물을 가수분해하여 구조식(Ⅳ)의 화합물을 제조하고 또는상기 구조식에서 R3및 R2는 상기에서와 같고,(f) 구조식(ⅩI)의 이미노 화합물을 가수분해하여 구조식(Ⅷ)의 화합물을 제조하고, 또는상기 구조식에서R1는 하기에서와 같고, R3는 수소, 저급알킬 또는 페닐이며단, R3가 수소일때 R1는 2-클로로페닐이아니며,(g) 구조식(XII)의 화합물을 가수분해하여 구조식(Ⅷ)의 화합물을 제조하고, 또는상기 구조식에서R1는 하기에서와 같고, R4는 수소, 저급알카노일 또는 벤조일이며:(h) 형성된 구조식(Ⅷ) 화합물의 불소를 메톡사이드, 에톡사이드 또는 메틸메르캅티드로 치환하여 구조식(ⅩⅣ)의 화합물을 제조하고, 또는상기 구조식에서Z4및 Z5는 하기에서와 같고, Z5는 (C1∼C3) 알콕시 또는 메틸티이고,(ⅰ) 형성된 구조식(XV) 화합물의 브롬을 시아나이드로 치환하여 구조식 (XVI)의 화합물을 제조하고, 또는(j) 형성된 구조식(XVII)의 화합물을 환원시켜 구조식(ⅩⅧ)의 화합물을 제조하고, 또는(k) 형성된 구조식(ⅩⅧ)의 화합물을 1당량의 아세틸 클로라이드 도는 아세트산 무수물로 아실화하여 구조식(ⅩⅨ)의 화합물을 제조하고, 또는(l) 라세미 화합물(Ⅷ)을 광학적 활성아민과 함께 형성시킨 염으로서 분리시키고 산성화하여 광학적으로 활성이 있는 화합물(Ⅷ)을 방출시킴으로써 광학적 대장체로 분리하고: 또는(m) 형성된 구조식(Ⅷ)의 화합물을 구조식 R5CI의 산클로라이드 또는 상응하는 무수물 또는 이소시아네이트와 반응시켜 구조식(ⅩⅩ)의 화합물을 제조하고, 또는상기 구조식에서R5는 (C1∼C4) 알카노일, 벤조일, (C2∼C4) 카브알콕시, (C1∼C3) 알킬카보일, (C5∼C7)-사이클로알킬카바모일 또는 디(C1∼C3) 알킬카바모일이며 :(n) 형성된 구조식(Ⅷ)의 화합물을 이들의 약학적으로 무독한 양이온성 염으로 전환시켜 다음 구조식(Ⅰ)의 라세미 또는 광학적 활성 화합물을 제조하는 방법.상기 구조식에서R은 수소, (C1∼C4)-알카노일, 벤조일, (C2∼C4)-카브알콕시, (C1∼C3)-알킬카바모일, (C5∼C7)-사이클로알킬카바모일 또는 디(C1∼C3)-알킬카바모일이며R1는여기에서Z는 플루오로Z1는 아세트아미도, 아미노, 벤질옥시, 클로로, 페녹시, 니트로, 또는 트리플루오로메틸,Z2는 아세트아미노, 아미노, 벤질옥시, 페녹시, 니트로 또는 트리플루오로메틸,Z3는 메틸 (C1∼C2) 알콕시, 메틸티오, 클로로 또는 플루오로Z4및 Z5는 각각 독립적으로 수소, 메틸, 브로모, 클로로, 플루오로, 시아노, 니트로 또는 트리플루오로메틸.Y는 수소, 메틸, 벤질옥시, (C1∼C2) 알콕시, 클로로, 브로모 또는 플루오로,Y1는 수소 또는 메톡시Y2는 플루오로 또는 클로로이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019840006723A KR850000382B1 (ko) | 1980-07-28 | 1984-10-29 | 5-치환된 옥사졸리딘-2, 4-디온의 제조방법 |
| KR1019840006724A KR850000387B1 (ko) | 1980-07-28 | 1984-10-29 | 5-치환된 옥사졸리딘-2, 4-디온의 제조방법 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17320680A | 1980-07-28 | 1980-07-28 | |
| US173,206 | 1980-07-28 | ||
| US06/222,202 US4367234A (en) | 1980-07-28 | 1981-01-02 | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| US222,202 | 1981-01-02 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840006723A Division KR850000382B1 (ko) | 1980-07-28 | 1984-10-29 | 5-치환된 옥사졸리딘-2, 4-디온의 제조방법 |
| KR1019840006724A Division KR850000387B1 (ko) | 1980-07-28 | 1984-10-29 | 5-치환된 옥사졸리딘-2, 4-디온의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830006247A true KR830006247A (ko) | 1983-09-20 |
| KR850000381B1 KR850000381B1 (ko) | 1985-03-23 |
Family
ID=26868872
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810002716A KR850000381B1 (ko) | 1980-07-28 | 1981-07-27 | 5-치환된 옥사졸리딘-2,-4디온의 제조방법 |
| KR1019840006724A KR850000387B1 (ko) | 1980-07-28 | 1984-10-29 | 5-치환된 옥사졸리딘-2, 4-디온의 제조방법 |
| KR1019840006723A KR850000382B1 (ko) | 1980-07-28 | 1984-10-29 | 5-치환된 옥사졸리딘-2, 4-디온의 제조방법 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840006724A KR850000387B1 (ko) | 1980-07-28 | 1984-10-29 | 5-치환된 옥사졸리딘-2, 4-디온의 제조방법 |
| KR1019840006723A KR850000382B1 (ko) | 1980-07-28 | 1984-10-29 | 5-치환된 옥사졸리딘-2, 4-디온의 제조방법 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4367234A (ko) |
| KR (3) | KR850000381B1 (ko) |
| AR (3) | AR228061A1 (ko) |
| AT (1) | AT376424B (ko) |
| AU (1) | AU526905B2 (ko) |
| CA (1) | CA1155855A (ko) |
| CH (1) | CH653025A5 (ko) |
| DD (1) | DD202149A5 (ko) |
| DE (1) | DE3129309A1 (ko) |
| DK (1) | DK151882C (ko) |
| ES (3) | ES8306367A1 (ko) |
| FI (1) | FI77457C (ko) |
| FR (1) | FR2487348B1 (ko) |
| GB (3) | GB2083810B (ko) |
| GR (1) | GR74590B (ko) |
| HU (1) | HU185682B (ko) |
| IE (1) | IE51427B1 (ko) |
| IL (1) | IL63422A (ko) |
| IT (1) | IT1138110B (ko) |
| LU (1) | LU83512A1 (ko) |
| NL (1) | NL8103536A (ko) |
| NO (1) | NO812558L (ko) |
| NZ (1) | NZ197853A (ko) |
| PH (1) | PH17421A (ko) |
| PT (1) | PT73437B (ko) |
| SE (1) | SE460849B (ko) |
| YU (3) | YU185281A (ko) |
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| US4689336A (en) * | 1981-01-02 | 1987-08-25 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine 2,4-diones |
| GR78120B (ko) * | 1982-03-01 | 1984-09-26 | Pfizer | |
| US4430337A (en) * | 1982-06-23 | 1984-02-07 | Pfizer Inc. | Alicyclic substituted oxazolidine-2,4-diones having hypoglycemic activity |
| JPS59186916A (ja) * | 1983-04-06 | 1984-10-23 | Aiji Noda | 膵石症治療剤 |
| US5130379A (en) * | 1988-03-08 | 1992-07-14 | Pfizer Inc. | Hypoglycemic thiazolidinedione derivatives |
| US4946942A (en) * | 1988-03-11 | 1990-08-07 | Bioresearch, Inc. | Urethane-protected amino acid-N-carboxyanhydrides |
| US5442124A (en) * | 1989-06-30 | 1995-08-15 | Firmenich Sa | Process for the preparation of novel aromatic compounds |
| WO1991007107A1 (en) * | 1989-11-13 | 1991-05-30 | Pfizer Inc. | Oxazolidinedione hypoglycemic agents |
| US5036079A (en) * | 1989-12-07 | 1991-07-30 | Pfizer Inc. | Hypoglycemic thiazolidinedione derivatives |
| CA2064815C (en) * | 1990-06-07 | 1999-11-16 | Alan Duncan Robertson | Therapeutic heterocyclic compounds |
| GB9017218D0 (en) * | 1990-08-06 | 1990-09-19 | Beecham Group Plc | Novel compounds |
| DE69106714T2 (de) * | 1990-08-23 | 1995-05-11 | Pfizer | Hypoglykämische hydroxyharnstoffderivate. |
| TW222626B (ko) | 1991-07-22 | 1994-04-21 | Pfizer | |
| US5498621A (en) * | 1992-05-01 | 1996-03-12 | Pfizer Inc. | Oxazolidinedione hypoglycemic agents |
| US5401761A (en) * | 1993-12-09 | 1995-03-28 | Pfizer, Inc. | Thiazolidinedione hypoglycemic agents |
| US5925656A (en) * | 1995-04-10 | 1999-07-20 | Dr. Reddy's Research Foundation | Compounds having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
| GB9604242D0 (en) | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| US5801173A (en) * | 1996-05-06 | 1998-09-01 | Dr. Reddy's Research Foundation | Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
| ZA973850B (en) * | 1996-05-06 | 1997-12-02 | Reddy Research Foundation | Novel antidiabetic compounds having hypolipidaemic, anti-hypertensive properties, process for their preparation and pharmaceutical compositions containing them. |
| US5889032A (en) * | 1996-05-06 | 1999-03-30 | Dr. Reddy's Research Foundation | Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
| US5919782A (en) * | 1996-05-06 | 1999-07-06 | Dr. Reddy's Research Foundation | Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
| USRE39266E1 (en) * | 1996-07-01 | 2006-09-05 | Dr. Reddy's Laboratories, Limited | Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
| BR9711098B1 (pt) * | 1996-07-01 | 2011-10-04 | compostos heterocìclicos, processo para sua preparação e composições farmacêuticas contendo os mesmos e seu uso no tratamento de diabetes e doenças relacionadas. | |
| US6114526A (en) | 1996-07-01 | 2000-09-05 | Dr. Reddy's Research Foundation | Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
| US6372750B2 (en) * | 1996-07-01 | 2002-04-16 | Dr. Reddy's Research Foundation | Heterocyclic compounds, process for their preparation and pharmaceutical compounds containing them and their use in the treatment of diabetes and related diseases |
| AU743411B2 (en) * | 1998-08-21 | 2002-01-24 | Viropharma Incorporated | Compounds, compositions and methods for treating or preventing viral infections and associated diseases |
| WO2000018745A1 (en) * | 1998-09-30 | 2000-04-06 | Roche Diagnostics Gmbh | Oxazolidine derivatives for the treatment and prevention of metabolic bone disorders |
| EP1194147B1 (en) | 1999-06-18 | 2007-01-10 | Merck & Co., Inc. | Arylthiazolidinedione and aryloxazolidinedione derivatives |
| EP1194146B1 (en) | 1999-06-18 | 2006-07-19 | Merck & Co., Inc. | Arylthiazolidinedione and aryloxazolidinedione derivatives |
| AR065670A1 (es) | 2007-03-09 | 2009-06-24 | Indigene Pharmaceuticals Inc | Combinacion de metformina r-(+) lipoato y agentes antihiperlipidemicos para el tratamiento de hiperglucemia diabetica y complicaciones diabeticas |
| JP5417860B2 (ja) * | 2008-08-26 | 2014-02-19 | 住友化学株式会社 | α−ヒドロキシエステル類の製造方法 |
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| DE729852C (de) * | 1939-07-06 | 1943-01-04 | Carl Nachtigall | Verfahren zur Herstellung von 2, 4-Dioxooxazolidinen |
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| GB1227428A (ko) * | 1968-04-08 | 1971-04-07 | ||
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1981
- 1981-01-02 US US06/222,202 patent/US4367234A/en not_active Expired - Fee Related
- 1981-07-22 GB GB8122525A patent/GB2083810B/en not_active Expired
- 1981-07-22 HU HU812142A patent/HU185682B/hu not_active IP Right Cessation
- 1981-07-24 SE SE8104542A patent/SE460849B/sv not_active IP Right Cessation
- 1981-07-24 AT AT0328681A patent/AT376424B/de not_active IP Right Cessation
- 1981-07-24 DE DE19813129309 patent/DE3129309A1/de active Granted
- 1981-07-24 AR AR286202A patent/AR228061A1/es active
- 1981-07-27 PT PT73437A patent/PT73437B/pt unknown
- 1981-07-27 IE IE1695/81A patent/IE51427B1/en unknown
- 1981-07-27 AU AU73435/81A patent/AU526905B2/en not_active Ceased
- 1981-07-27 YU YU01852/81A patent/YU185281A/xx unknown
- 1981-07-27 KR KR1019810002716A patent/KR850000381B1/ko active
- 1981-07-27 GR GR65637A patent/GR74590B/el unknown
- 1981-07-27 PH PH25969A patent/PH17421A/en unknown
- 1981-07-27 LU LU83512A patent/LU83512A1/fr unknown
- 1981-07-27 CH CH4879/81A patent/CH653025A5/fr not_active IP Right Cessation
- 1981-07-27 IT IT23175/81A patent/IT1138110B/it active
- 1981-07-27 CA CA000382586A patent/CA1155855A/en not_active Expired
- 1981-07-27 NZ NZ197853A patent/NZ197853A/en unknown
- 1981-07-27 IL IL63422A patent/IL63422A/xx unknown
- 1981-07-27 NL NL8103536A patent/NL8103536A/nl not_active Application Discontinuation
- 1981-07-27 FI FI812340A patent/FI77457C/fi not_active IP Right Cessation
- 1981-07-27 NO NO812558A patent/NO812558L/no unknown
- 1981-07-27 DK DK334681A patent/DK151882C/da active
- 1981-07-27 FR FR8114543A patent/FR2487348B1/fr not_active Expired
- 1981-07-27 ES ES504322A patent/ES8306367A1/es not_active Expired
- 1981-07-28 DD DD81232154A patent/DD202149A5/de unknown
-
1982
- 1982-05-13 AR AR289384A patent/AR231721A1/es active
- 1982-05-13 AR AR289383A patent/AR230834A1/es active
- 1982-08-02 ES ES514665A patent/ES8306132A1/es not_active Expired
- 1982-08-02 ES ES514666A patent/ES8306133A1/es not_active Expired
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1983
- 1983-04-18 YU YU00881/83A patent/YU88183A/xx unknown
- 1983-04-18 YU YU00882/83A patent/YU88283A/xx unknown
- 1983-06-24 GB GB08317145A patent/GB2132609B/en not_active Expired
- 1983-06-24 GB GB08317144A patent/GB2128987B/en not_active Expired
-
1984
- 1984-10-29 KR KR1019840006724A patent/KR850000387B1/ko not_active IP Right Cessation
- 1984-10-29 KR KR1019840006723A patent/KR850000382B1/ko not_active IP Right Cessation
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