UA78823C2 - Thiophen glycoside derivatives and their use - Google Patents
Thiophen glycoside derivatives and their use Download PDFInfo
- Publication number
- UA78823C2 UA78823C2 UAA200501215A UA2005001215A UA78823C2 UA 78823 C2 UA78823 C2 UA 78823C2 UA A200501215 A UAA200501215 A UA A200501215A UA 2005001215 A UA2005001215 A UA 2005001215A UA 78823 C2 UA78823 C2 UA 78823C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alkyl
- phenyl
- compounds
- formula
- replaced
- Prior art date
Links
- -1 Thiophen glycoside Chemical class 0.000 title description 24
- 229930182470 glycoside Natural products 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 238000000034 method Methods 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000013543 active substance Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 101000920618 Homo sapiens Transcription and mRNA export factor ENY2 Proteins 0.000 claims description 12
- 102100031954 Transcription and mRNA export factor ENY2 Human genes 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229940126601 medicinal product Drugs 0.000 claims description 9
- 239000008280 blood Substances 0.000 claims description 8
- 210000004369 blood Anatomy 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 141
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 120
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 83
- 239000000243 solution Substances 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 37
- 239000000047 product Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
- 239000012074 organic phase Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000012528 membrane Substances 0.000 description 20
- 210000004379 membrane Anatomy 0.000 description 19
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 18
- 229940088623 biologically active substance Drugs 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000556 agonist Substances 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- 230000003993 interaction Effects 0.000 description 16
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 15
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 15
- 210000000110 microvilli Anatomy 0.000 description 15
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000007983 Tris buffer Substances 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 9
- 229930195725 Mannitol Natural products 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000000594 mannitol Substances 0.000 description 9
- 235000010355 mannitol Nutrition 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- 210000000813 small intestine Anatomy 0.000 description 9
- 102000004877 Insulin Human genes 0.000 description 8
- 108090001061 Insulin Proteins 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
- 239000008103 glucose Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000005557 antagonist Substances 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 229940125396 insulin Drugs 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
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- 210000003734 kidney Anatomy 0.000 description 6
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- 239000006228 supernatant Substances 0.000 description 6
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- XQBKMDLTVLHZKS-UHFFFAOYSA-N 3-phenylmethoxy-5-propan-2-ylthiophene-2-carboxylic acid Chemical compound S1C(C(C)C)=CC(OCC=2C=CC=CC=2)=C1C(O)=O XQBKMDLTVLHZKS-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- 229940100389 Sulfonylurea Drugs 0.000 description 5
- WBXQXRXMGCOVHA-UHFFFAOYSA-N [methyl(nitroso)amino]methyl acetate Chemical compound O=NN(C)COC(C)=O WBXQXRXMGCOVHA-UHFFFAOYSA-N 0.000 description 5
- 230000001133 acceleration Effects 0.000 description 5
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- RVDUJCGAAPQDBO-UHFFFAOYSA-N 3-hydroxythiophene-2-carboxylic acid Chemical class OC(=O)C=1SC=CC=1O RVDUJCGAAPQDBO-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
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- 150000002338 glycosides Chemical class 0.000 description 4
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Landscapes
- Health & Medical Sciences (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10231370A DE10231370B4 (de) | 2002-07-11 | 2002-07-11 | Thiophenglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
PCT/EP2003/006841 WO2004007517A1 (de) | 2002-07-11 | 2003-06-27 | Neue thiophenglycosidderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
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UA78823C2 true UA78823C2 (en) | 2007-04-25 |
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UAA200501215A UA78823C2 (en) | 2002-07-11 | 2003-06-27 | Thiophen glycoside derivatives and their use |
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US (2) | US7101856B2 (ru) |
EP (4) | EP1523488B1 (ru) |
JP (1) | JP4511927B2 (ru) |
KR (1) | KR20050021452A (ru) |
CN (2) | CN101240000A (ru) |
AR (1) | AR040474A1 (ru) |
AT (4) | ATE477266T1 (ru) |
AU (1) | AU2003246620B2 (ru) |
BR (1) | BR0312513A (ru) |
CA (1) | CA2493391C (ru) |
CR (1) | CR7718A (ru) |
CY (1) | CY1108754T1 (ru) |
DE (5) | DE10231370B4 (ru) |
DK (1) | DK1523488T3 (ru) |
EC (1) | ECSP055531A (ru) |
ES (1) | ES2316818T3 (ru) |
HK (1) | HK1080482A1 (ru) |
HN (1) | HN2003000215A (ru) |
HR (1) | HRP20050014A2 (ru) |
IL (2) | IL166058A0 (ru) |
JO (1) | JO2707B1 (ru) |
MA (1) | MA27366A1 (ru) |
ME (1) | MEP60708A (ru) |
MX (1) | MXPA05000044A (ru) |
MY (1) | MY137039A (ru) |
NO (1) | NO20050649L (ru) |
OA (1) | OA12880A (ru) |
PA (1) | PA8577101A1 (ru) |
PE (1) | PE20040655A1 (ru) |
PL (1) | PL372931A1 (ru) |
PT (1) | PT1523488E (ru) |
RS (1) | RS51002B (ru) |
RU (1) | RU2317300C2 (ru) |
SI (1) | SI1523488T1 (ru) |
TN (1) | TNSN05007A1 (ru) |
TW (1) | TWI318981B (ru) |
UA (1) | UA78823C2 (ru) |
UY (1) | UY27891A1 (ru) |
WO (1) | WO2004007517A1 (ru) |
ZA (1) | ZA200409779B (ru) |
Families Citing this family (109)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1020944C (zh) | 1990-01-30 | 1993-05-26 | 阿图尔-费希尔股份公司费希尔厂 | 紧固件 |
DE10258008B4 (de) * | 2002-12-12 | 2006-02-02 | Sanofi-Aventis Deutschland Gmbh | Heterocyclische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
DE10308353A1 (de) | 2003-02-27 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Diarylcycloalkylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
US7439232B2 (en) | 2003-04-01 | 2008-10-21 | Taisho Pharmaceutical Co., Ltd. | Heteroaryl 5-thio-β-D-glucopyranoside derivatives and therapeutic agents for diabetes containing the same |
US8785403B2 (en) | 2003-08-01 | 2014-07-22 | Mitsubishi Tanabe Pharma Corporation | Glucopyranoside compound |
DK2896397T4 (da) | 2003-08-01 | 2020-11-16 | Mitsubishi Tanabe Pharma Corp | Nye forbindelser med hæmmende aktivitet mod natriumafhængig glukosetransportør |
TW200606129A (en) | 2004-07-26 | 2006-02-16 | Chugai Pharmaceutical Co Ltd | Novel cyclohexane derivative, its prodrug, its salt and diabetic therapeutic agent containing the same |
WO2006010379A1 (en) | 2004-07-29 | 2006-02-02 | Actelion Pharmaceuticals Ltd. | Novel thiophene derivatives as immunosuppressive agents |
DE102004063099B4 (de) * | 2004-12-22 | 2009-02-12 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung von Thiophenglycosidderivaten |
TW200637869A (en) | 2005-01-28 | 2006-11-01 | Chugai Pharmaceutical Co Ltd | The spiroketal derivatives and the use as therapeutical agent for diabetes of the same |
AR053329A1 (es) * | 2005-01-31 | 2007-05-02 | Tanabe Seiyaku Co | Derivados de indol utiles como inhibidores de los transportadores de glucosa dependientes del sodio (sglt) |
MY147375A (en) | 2005-01-31 | 2012-11-30 | Mitsubishi Tanabe Pharma Corp | Indole derivatives |
BRPI0609665A2 (pt) | 2005-03-23 | 2010-04-20 | Actelion Pharmaceuticals Ltd | composto, composição farmacêutica, e, uso de um composto |
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- 2004-12-14 MA MA28004A patent/MA27366A1/fr unknown
- 2004-12-23 IL IL16605804A patent/IL166058A0/xx not_active IP Right Cessation
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2005
- 2005-01-10 HR HR20050014A patent/HRP20050014A2/hr not_active Application Discontinuation
- 2005-01-10 TN TNP2005000007A patent/TNSN05007A1/en unknown
- 2005-01-11 EC EC2005005531A patent/ECSP055531A/es unknown
- 2005-02-07 NO NO20050649A patent/NO20050649L/no unknown
- 2005-03-07 CR CR7718A patent/CR7718A/es not_active Application Discontinuation
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2006
- 2006-01-10 HK HK06100362A patent/HK1080482A1/xx not_active IP Right Cessation
- 2006-08-14 US US11/464,338 patent/US7666848B2/en not_active Expired - Fee Related
-
2008
- 2008-06-03 IL IL191926A patent/IL191926A0/en unknown
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2009
- 2009-02-05 CY CY20091100138T patent/CY1108754T1/el unknown
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