RU95122667A - NEW TIAZOLIDINDIONS AND CONTAINING THEIR MEDICINES - Google Patents
NEW TIAZOLIDINDIONS AND CONTAINING THEIR MEDICINESInfo
- Publication number
- RU95122667A RU95122667A RU95122667/04A RU95122667A RU95122667A RU 95122667 A RU95122667 A RU 95122667A RU 95122667/04 A RU95122667/04 A RU 95122667/04A RU 95122667 A RU95122667 A RU 95122667A RU 95122667 A RU95122667 A RU 95122667A
- Authority
- RU
- Russia
- Prior art keywords
- compounds
- general formula
- alkyl
- heteroatoms
- hydrogen
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000005842 heteroatoms Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 229940079593 drugs Drugs 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 1
- 206010012601 Diabetes mellitus Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000003287 optical Effects 0.000 claims 1
- ZBOGMAOYAPGJBU-UHFFFAOYSA-N CCC(B1)=C(CCCCC2)C2=C1CO Chemical compound CCC(B1)=C(CCCCC2)C2=C1CO ZBOGMAOYAPGJBU-UHFFFAOYSA-N 0.000 description 1
Claims (4)
в которой А - карбоциклическое кольцо с 5 или 6 атомами углерода или гетероциклические кольцо с 1 или 2 гетероатомами, причем гетероатомы обозначают кислород, азот или серу, а гетероциклы при необходимости могут нести на одном или нескольких атомах азота один атом кислорода;
B- -CH=CH-, -N=CH-, -CH=N-;
W- CH2, O, CH(OH) или СО;
X-S, O или NR2, причем остаток R2 является водородом;
Y-N;
R - нафтил, пиридил, фурил, тиенил или фенил, при необходимости одно- или двузамещенный С1 - С3-алкилом, CF3, С1 - С3-алкокси, F, Cl или Br;
R1-водород или С1 - С6-алкил;
n = 2,
а также их таутомеры, энантиомеры, диастереомеры и физиологически приемлемые соли.1. The compound of formula I
in which A is a carbocyclic ring with 5 or 6 carbon atoms or a heterocyclic ring with 1 or 2 heteroatoms, heteroatoms being oxygen, nitrogen or sulfur, and heterocycles can optionally carry one oxygen atom on one or more nitrogen atoms;
B- -CH = CH-, -N = CH-, -CH = N-;
W-CH 2 , O, CH (OH) or CO;
XS, O, or NR 2 , wherein R 2 is hydrogen;
YN;
R is naphthyl, pyridyl, furyl, thienyl or phenyl, optionally mono- or disubstituted with C 1 -C 3 -alkyl, CF 3 , C 1 -C 3 -alkoxy, F, Cl or Br;
R 1 is hydrogen or C 1 - C 6 -alkyl;
n = 2,
as well as their tautomers, enantiomers, diastereomers and physiologically acceptable salts.
в которой А - карбоциклическое кольцо с 5 или 6 атомами углерода или гетероциклическое кольцо с 1 или 2 гетероатомами, причем гетероатомы обозначают кислород, азот или серу, а гетероциклы при необходимости могут нести на одном или нескольких атомах азота один атом кислорода;
B -CH=CH-, -N=CH-, -CH=N-;
W -CH2, O, -CH(OH) или СО,
X-S, O или NR2, причем остаток R2 является водородом;
Y-N;
R-нафтил, пиридил, фурил, тиенил или фенил, при необходимости одно- или двузамещенный С1 - С3-алкилом, CF3, С1 - С3-алкокси, F, Cl или Br;
R1-водород или С1 - С6-алкил;
n = 2,
а также их таутомеров, энантиомеров, диастереомеров и физиологически приемлемых солей, отличающийся тем, что известным образом
а) соединения общей формулы II
в которой A, B, W, X, Y, R, R1 и n имеют указанные значения,
вводят в реакцию с тиазолидиндионом с получением соединений общей формулы III
в которой A, B, W, X, Y, R, R1 и n имеют указанные значения,
и затем восстановлением двойной связи получают соединение формулы I, или
в) соединения общей формулы IV
в которой A, B, W, X, Y, R, R1 и n имеют указанные значения,
вводят в реакцию с NaNO2 в присутствии акрилового эфира и HCl или HBr с получением соединений общей формулы V
в которой A, B, W, X, Y, R, R1 и n имеют указанные выше значения;
Hal обозначает хлор или бром;
R3 обозначает С1 - С6-алкильный остаток,
и затем циклизуют соединения общей формулы V с тиомочевиной с получением соединений общей формулы VI
в которой A, B, W, X, Y, R, R1 и n имеют указанные значения,
и превращают обработкой кислотой в соединения общей формулы I и затем при желании переводят полученные соединения в их таутомеры, физиологически приемлемые соли, а также их оптические изомеры.2. The method of obtaining compounds of formula I
in which A is a carbocyclic ring with 5 or 6 carbon atoms or a heterocyclic ring with 1 or 2 heteroatoms, heteroatoms being oxygen, nitrogen or sulfur, and heterocycles can optionally carry one oxygen atom on one or more nitrogen atoms;
B-CH = CH-, -N = CH-, -CH = N-;
W —CH 2 , O, —CH (OH) or CO,
XS, O, or NR 2 , wherein R 2 is hydrogen;
YN;
R-naphthyl, pyridyl, furyl, thienyl or phenyl, optionally mono- or disubstituted with C 1 -C 3 -alkyl, CF 3 , C 1 -C 3 -alkoxy, F, Cl or Br;
R 1 is hydrogen or C 1 - C 6 -alkyl;
n = 2,
as well as their tautomers, enantiomers, diastereomers and physiologically acceptable salts, characterized in that in a known manner
a) compounds of general formula II
in which A, B, W, X, Y, R, R 1 and n have the indicated meanings,
enter into reaction with thiazolidinedione to obtain compounds of general formula III
in which A, B, W, X, Y, R, R 1 and n have the indicated meanings,
and then reducing the double bond to give a compound of formula I, or
c) compounds of general formula IV
in which A, B, W, X, Y, R, R 1 and n have the indicated meanings,
enter into reaction with NaNO 2 in the presence of acrylic ether and HCl or HBr to obtain compounds of general formula V
in which A, B, W, X, Y, R, R 1 and n have the above values;
Hal refers to chlorine or bromine;
R 3 stands for C 1 - C 6 -alkyl residue,
and then cyclizing compounds of general formula V with thiourea to obtain compounds of general formula VI
in which A, B, W, X, Y, R, R 1 and n have the indicated meanings,
and is converted by treatment with an acid into compounds of the general formula I and then, if desired, transfer the obtained compounds to their tautomers, physiologically acceptable salts, as well as their optical isomers.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4317320.9 | 1993-05-25 | ||
| DE4317320A DE4317320A1 (en) | 1993-05-25 | 1993-05-25 | New thiazolidinediones and medicines containing them |
| PCT/EP1994/001619 WO1994027995A1 (en) | 1993-05-25 | 1994-05-19 | New thiazolidindiones and drugs containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU95122667A true RU95122667A (en) | 1997-11-27 |
| RU2122002C1 RU2122002C1 (en) | 1998-11-20 |
Family
ID=6488833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU95122667A RU2122002C1 (en) | 1993-05-25 | 1994-05-19 | Novel thiazolidinediones and drugs containing thereof |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5599826A (en) |
| EP (1) | EP0700397B1 (en) |
| JP (1) | JP3162721B2 (en) |
| KR (1) | KR100243783B1 (en) |
| CN (1) | CN1040324C (en) |
| AT (1) | ATE223409T1 (en) |
| AU (1) | AU682699B2 (en) |
| CA (1) | CA2163028C (en) |
| CL (1) | CL2004001167A1 (en) |
| CY (1) | CY2415B1 (en) |
| CZ (1) | CZ285927B6 (en) |
| DE (2) | DE4317320A1 (en) |
| DK (1) | DK0700397T3 (en) |
| ES (1) | ES2180581T3 (en) |
| FI (1) | FI955685A (en) |
| HU (1) | HU217065B (en) |
| NO (1) | NO307832B1 (en) |
| NZ (1) | NZ267410A (en) |
| PL (1) | PL180046B1 (en) |
| PT (1) | PT700397E (en) |
| RO (1) | RO114328B1 (en) |
| RU (1) | RU2122002C1 (en) |
| SK (1) | SK282618B6 (en) |
| UA (1) | UA41362C2 (en) |
| WO (1) | WO1994027995A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA009192B1 (en) * | 1998-11-12 | 2007-12-28 | Смитклайн Бичам Корпорейшн | Method for the treatment of type 2 diabetes mellitus |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07138258A (en) * | 1993-11-16 | 1995-05-30 | Taiho Yakuhin Kogyo Kk | Thiazolidinedione derivative or salt thereof |
| ES2196163T3 (en) * | 1995-07-31 | 2003-12-16 | Shionogi & Co | PIRROLIDINE DERIVATIVES WITH AN INHIBITION ACTIVITY OF PHOSPHOLIPASE A2. |
| JPH09176162A (en) * | 1995-12-22 | 1997-07-08 | Toubishi Yakuhin Kogyo Kk | Thiazolidinedione derivative, its production and medicinal composition containing the same |
| DE19619819A1 (en) * | 1996-05-16 | 1997-11-20 | Boehringer Mannheim Gmbh | New thiazolidinediones, process for their preparation and medicaments containing them |
| DE19711617A1 (en) * | 1997-03-20 | 1998-09-24 | Boehringer Mannheim Gmbh | New thiazolidinediones, processes for their preparation and medicaments containing them |
| DE19711616A1 (en) * | 1997-03-20 | 1998-09-24 | Boehringer Mannheim Gmbh | Improved process for the preparation of thiazolidinediones |
| US6028088A (en) * | 1998-10-30 | 2000-02-22 | The University Of Mississippi | Flavonoid derivatives |
| CA2350599A1 (en) * | 1998-11-20 | 2000-06-02 | Genentech, Inc. | Method of inhibiting angiogenesis |
| ES2258431T3 (en) | 1999-08-02 | 2006-09-01 | F. Hoffmann-La Roche Ag | PROCESS FOR THE PREPARATION OF BENZOTIOFEN DERIVATIVES. |
| US6531609B2 (en) | 2000-04-14 | 2003-03-11 | Hoffmann-La Roche Inc. | Process for the preparation of thiazolidinedione derivatives |
| AU2001265914B2 (en) * | 2000-05-08 | 2005-11-03 | F. Hoffmann-La Roche Ag | Para-amine substituted phenylamide glucokinase activators |
| DE60121953T2 (en) | 2000-06-27 | 2007-03-08 | F. Hoffmann-La Roche Ag | METHOD OF MANUFACTURING MEDICINE PREPARATIONS |
| BR0116526A (en) * | 2000-12-25 | 2004-07-06 | Ono Pharmaceutical Co | Dihydronaphthalene-derived compounds and agents comprising the derivative as an active component |
| EP1392296A1 (en) * | 2001-04-06 | 2004-03-03 | F. Hoffmann-La Roche Ag | Thiazolidinediones alone or in conbination with other therapeutic agents for inhibiting or reducing tumour growth |
| EP1392295B1 (en) | 2001-05-15 | 2006-05-31 | F. Hoffmann-La Roche AG | Carboxylic acid substituted oxazole derivatives for use as ppar-alpha and -gamma activators in the treatment of diabetes |
| JP2003040877A (en) * | 2001-07-24 | 2003-02-13 | Sumika Fine Chemicals Co Ltd | Method for producing 5-[6-(2-fluorobenzyloxy)-2- naphthyl]methyl-2,4-thiazolidinedione and method for refining the same |
| US7102000B2 (en) * | 2002-03-08 | 2006-09-05 | Incyte San Diego Inc. | Heterocyclic amide derivatives for the treatment of diabetes and other diseases |
| CA2490152C (en) * | 2002-07-03 | 2009-04-07 | F. Hoffmann-La Roche Ag | Oxazole derivatives and their use as insulin sensitizers |
| PL375779A1 (en) * | 2002-08-30 | 2005-12-12 | F.Hoffmann-La Roche Ag | Novel 2-arylthiazole compounds as pparalpha and ppargamma agonists |
| EP1539746B1 (en) * | 2002-09-12 | 2006-11-15 | F. Hoffmann-La Roche Ag | N-substituted-1h-indol-5-propionic acid compounds as ppar agonists useful for the treatment of diabetes |
| ES2312819T3 (en) * | 2002-11-25 | 2009-03-01 | F. Hoffmann-La Roche Ag | DERIVATIVES OF INDOLILO. |
| CA2530309A1 (en) | 2003-06-26 | 2005-01-06 | F. Hoffmann-La Roche Ag | Process for the preparation of insulin sensitizer and intermediate compound thereof |
| CN101693202B (en) * | 2009-10-21 | 2011-04-20 | 沧州那瑞化学科技有限公司 | Hydrogenation reaction catalyst of pioglitazone hydrochloride key intermediate and hydrogenation reaction method |
| WO2013082106A1 (en) | 2011-12-02 | 2013-06-06 | The General Hospital Corporation | Differentiation into brown adipocytes |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1003445B (en) * | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | The preparation method of thiazolidine diketone derivative |
| HU210339B (en) * | 1985-05-21 | 1995-03-28 | Pfizer | Process for preparing thiazolidinediones and their pharmaceutical compositions haring hypoglycemic effect |
| GB8713861D0 (en) * | 1987-06-13 | 1987-07-15 | Beecham Group Plc | Compounds |
| ATE104626T1 (en) * | 1988-03-04 | 1994-05-15 | Volk Inc Kurt H | ITEM FOR IMMEDIATE SHIPPING BY MAIL WITH A MAILABLE REPLY CARD. |
| WO1989008652A1 (en) * | 1988-03-08 | 1989-09-21 | Pfizer Inc. | Thiazolidinedione derivatives as hypoglycemic agents |
| AU650465B2 (en) * | 1990-07-03 | 1994-06-23 | Yamanouchi Pharmaceutical Co., Ltd. | Bisheterocyclic compound |
| FR2688220A1 (en) * | 1992-03-06 | 1993-09-10 | Adir | NOVEL THIAZOLIDINE-2,4-DIONE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
-
1993
- 1993-05-25 DE DE4317320A patent/DE4317320A1/en not_active Withdrawn
-
1994
- 1994-05-19 RO RO95-01981A patent/RO114328B1/en unknown
- 1994-05-19 PL PL94311752A patent/PL180046B1/en not_active IP Right Cessation
- 1994-05-19 US US08/578,561 patent/US5599826A/en not_active Expired - Fee Related
- 1994-05-19 WO PCT/EP1994/001619 patent/WO1994027995A1/en active IP Right Grant
- 1994-05-19 CA CA002163028A patent/CA2163028C/en not_active Expired - Fee Related
- 1994-05-19 CZ CZ952999A patent/CZ285927B6/en not_active IP Right Cessation
- 1994-05-19 UA UA95114968A patent/UA41362C2/en unknown
- 1994-05-19 EP EP94918342A patent/EP0700397B1/en not_active Expired - Lifetime
- 1994-05-19 NZ NZ267410A patent/NZ267410A/en not_active IP Right Cessation
- 1994-05-19 DK DK94918342T patent/DK0700397T3/en active
- 1994-05-19 AU AU69704/94A patent/AU682699B2/en not_active Ceased
- 1994-05-19 KR KR1019950705207A patent/KR100243783B1/en not_active IP Right Cessation
- 1994-05-19 RU RU95122667A patent/RU2122002C1/en not_active IP Right Cessation
- 1994-05-19 JP JP50018495A patent/JP3162721B2/en not_active Expired - Fee Related
- 1994-05-19 HU HU9503376A patent/HU217065B/en not_active IP Right Cessation
- 1994-05-19 DE DE59410181T patent/DE59410181D1/en not_active Expired - Fee Related
- 1994-05-19 SK SK1461-95A patent/SK282618B6/en not_active IP Right Cessation
- 1994-05-19 AT AT94918342T patent/ATE223409T1/en not_active IP Right Cessation
- 1994-05-19 ES ES94918342T patent/ES2180581T3/en not_active Expired - Lifetime
- 1994-05-19 PT PT94918342T patent/PT700397E/en unknown
- 1994-05-19 CN CN94192240A patent/CN1040324C/en not_active Expired - Fee Related
-
1995
- 1995-11-24 FI FI955685A patent/FI955685A/en not_active Application Discontinuation
- 1995-11-24 NO NO954762A patent/NO307832B1/en unknown
-
2003
- 2003-09-11 CY CY0300064A patent/CY2415B1/en unknown
-
2004
- 2004-05-20 CL CL200401167A patent/CL2004001167A1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA009192B1 (en) * | 1998-11-12 | 2007-12-28 | Смитклайн Бичам Корпорейшн | Method for the treatment of type 2 diabetes mellitus |
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