DE102008017590A1 - Glucopyranosidderivate - Google Patents
Glucopyranosidderivate Download PDFInfo
- Publication number
- DE102008017590A1 DE102008017590A1 DE102008017590A DE102008017590A DE102008017590A1 DE 102008017590 A1 DE102008017590 A1 DE 102008017590A1 DE 102008017590 A DE102008017590 A DE 102008017590A DE 102008017590 A DE102008017590 A DE 102008017590A DE 102008017590 A1 DE102008017590 A1 DE 102008017590A1
- Authority
- DE
- Germany
- Prior art keywords
- salts
- phenyl
- formula
- solvates
- glucopyranos
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- -1 β-D-glucopyranos-1-yl Chemical group 0.000 claims description 129
- 150000003839 salts Chemical class 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 55
- 239000012453 solvate Substances 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 210000004369 blood Anatomy 0.000 claims description 8
- 239000008280 blood Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 235000000346 sugar Nutrition 0.000 claims description 7
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 241000972349 Ocoa Species 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- LDEJPSVMAAQDQE-JKORXLELSA-N (2r,3r,4s,5s,6r)-6-(hydroxymethyl)-2-[(3r)-3-(4-methoxyphenyl)-2,3-dihydro-1h-inden-5-yl]oxane-2,3,4,5-tetrol Chemical compound C1=CC(OC)=CC=C1[C@@H]1C2=CC([C@]3(O)[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=CC=C2CC1 LDEJPSVMAAQDQE-JKORXLELSA-N 0.000 claims description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- MBZRNQQCLFLIGZ-QMCAAQAGSA-N (2R,3R,4S,5S,6R)-2-[1-(4-ethoxyphenyl)indol-6-yl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound CCOc1ccc(cc1)-n1ccc2ccc(cc12)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O MBZRNQQCLFLIGZ-QMCAAQAGSA-N 0.000 claims description 2
- KXOYEMOUOIVVMP-QMCAAQAGSA-N (2R,3R,4S,5S,6R)-2-[3-(4-ethoxyphenyl)-1-benzofuran-5-yl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound CCOc1ccc(cc1)-c1coc2ccc(cc12)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KXOYEMOUOIVVMP-QMCAAQAGSA-N 0.000 claims description 2
- MEMVSJFUOUPIFT-RPAXGWLXSA-N (2R,3R,4S,5S,6R)-2-[3-(4-ethoxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound CCOc1ccc(cc1)C1COc2ccc(cc12)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O MEMVSJFUOUPIFT-RPAXGWLXSA-N 0.000 claims description 2
- GFHKUBJXPRTSDP-MXKXIPCASA-N (2R,3R,4S,5S,6R)-2-[3-(4-ethoxyphenyl)-2,3-dihydro-1H-inden-5-yl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound CCOc1ccc(cc1)C1CCc2ccc(cc12)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GFHKUBJXPRTSDP-MXKXIPCASA-N 0.000 claims description 2
- ZIWVLSCTDVPRJZ-YMQHIKHWSA-N (2R,3R,4S,5S,6R)-6-(hydroxymethyl)-2-[2-(4-methoxyphenyl)-1-benzofuran-5-yl]oxane-2,3,4,5-tetrol Chemical compound COc1ccc(cc1)-c1cc2cc(ccc2o1)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O ZIWVLSCTDVPRJZ-YMQHIKHWSA-N 0.000 claims description 2
- VFHXMADKYIEIKQ-YMQHIKHWSA-N (2R,3R,4S,5S,6R)-6-(hydroxymethyl)-2-[3-(4-methoxyphenyl)-1-benzofuran-5-yl]oxane-2,3,4,5-tetrol Chemical compound COc1ccc(cc1)-c1coc2ccc(cc12)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VFHXMADKYIEIKQ-YMQHIKHWSA-N 0.000 claims description 2
- BDAQTRHOZFFPTQ-UZQFATADSA-N (2R,3R,4S,5S,6R)-6-(hydroxymethyl)-2-[3-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]oxane-2,3,4,5-tetrol Chemical compound COc1ccc(cc1)C1COc2ccc(cc12)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O BDAQTRHOZFFPTQ-UZQFATADSA-N 0.000 claims description 2
- LDEJPSVMAAQDQE-RPAXGWLXSA-N (2R,3R,4S,5S,6R)-6-(hydroxymethyl)-2-[3-(4-methoxyphenyl)-2,3-dihydro-1H-inden-5-yl]oxane-2,3,4,5-tetrol Chemical compound COc1ccc(cc1)C1CCc2ccc(cc12)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LDEJPSVMAAQDQE-RPAXGWLXSA-N 0.000 claims description 2
- HIIWQVXIFROHBD-MXKXIPCASA-N (2R,3R,4S,5S,6R)-6-(hydroxymethyl)-2-[8-(4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxane-2,3,4,5-tetrol Chemical compound COc1ccc(cc1)C1CCCc2ccc(cc12)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HIIWQVXIFROHBD-MXKXIPCASA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229940088679 drug related substance Drugs 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 235000002639 sodium chloride Nutrition 0.000 description 43
- 239000004480 active ingredient Substances 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 238000004949 mass spectrometry Methods 0.000 description 26
- 239000002904 solvent Substances 0.000 description 23
- 239000011734 sodium Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000556 agonist Substances 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 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 13
- 241000282414 Homo sapiens Species 0.000 description 13
- 239000008103 glucose Substances 0.000 description 13
- 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 13
- 239000000843 powder Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000008194 pharmaceutical composition Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
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- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
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- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/04—Carbocyclic radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/06—Heterocyclic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008017590A DE102008017590A1 (de) | 2008-04-07 | 2008-04-07 | Glucopyranosidderivate |
| EP09729525A EP2260051B1 (de) | 2008-04-07 | 2009-03-17 | Glucopyranosidderivate |
| JP2011503354A JP5485979B2 (ja) | 2008-04-07 | 2009-03-17 | グルコピラノシド誘導体 |
| CA2720586A CA2720586C (en) | 2008-04-07 | 2009-03-17 | Glucopyranoside derivatives |
| ES09729525T ES2394240T3 (es) | 2008-04-07 | 2009-03-17 | Derivados de glucopiranósido |
| US12/936,539 US8399509B2 (en) | 2008-04-07 | 2009-03-17 | Glucopyranoside derivatives |
| AU2009235786A AU2009235786B2 (en) | 2008-04-07 | 2009-03-17 | Glucopyranoside derivatives |
| PCT/EP2009/001946 WO2009124638A1 (de) | 2008-04-07 | 2009-03-17 | Glucopyranosidderivate |
| IL208065A IL208065A (en) | 2008-04-07 | 2010-09-07 | Glucopyrnoside derivatives, process for preparation, use and medications containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008017590A DE102008017590A1 (de) | 2008-04-07 | 2008-04-07 | Glucopyranosidderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102008017590A1 true DE102008017590A1 (de) | 2009-10-08 |
Family
ID=41051529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102008017590A Withdrawn DE102008017590A1 (de) | 2008-04-07 | 2008-04-07 | Glucopyranosidderivate |
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| US (1) | US8399509B2 (https=) |
| EP (1) | EP2260051B1 (https=) |
| JP (1) | JP5485979B2 (https=) |
| AU (1) | AU2009235786B2 (https=) |
| CA (1) | CA2720586C (https=) |
| DE (1) | DE102008017590A1 (https=) |
| ES (1) | ES2394240T3 (https=) |
| IL (1) | IL208065A (https=) |
| WO (1) | WO2009124638A1 (https=) |
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| WO2010128152A1 (en) * | 2009-05-07 | 2010-11-11 | Novartis Ag | Fused heterocyclic c-glycosides for the treatment of diabetes |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| WO2012165914A2 (en) * | 2011-06-01 | 2012-12-06 | Green Cross Corporation | Novel diphenylmethane derivatives as sglt2 inhibitors |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9340521B2 (en) * | 2013-03-18 | 2016-05-17 | Green Cross Corporation | Method for dual inhibition of SGLT1 and SGLT2 using diphenylmethane derivatives |
| WO2018013430A2 (en) | 2016-07-12 | 2018-01-18 | Arisan Therapeutics Inc. | Heterocyclic compounds for the treatment of arenavirus infection |
| US12419865B2 (en) | 2018-12-06 | 2025-09-23 | Arisan Therapeutics Inc. | Compounds for the treatment of arenavirus infection |
| WO2025160910A1 (en) * | 2024-02-01 | 2025-08-07 | New Wish Biotechnology Wuxi Co., Ltd. | Indazole compound and pharmaceutical composition, preparation method and use thereof |
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- 2009-03-17 US US12/936,539 patent/US8399509B2/en not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| AU2009235786B2 (en) | 2013-09-26 |
| EP2260051A1 (de) | 2010-12-15 |
| AU2009235786A1 (en) | 2009-10-15 |
| CA2720586A1 (en) | 2009-10-15 |
| ES2394240T3 (es) | 2013-01-23 |
| JP5485979B2 (ja) | 2014-05-07 |
| IL208065A0 (en) | 2010-12-30 |
| EP2260051B1 (de) | 2012-10-17 |
| US20110028414A1 (en) | 2011-02-03 |
| IL208065A (en) | 2014-03-31 |
| CA2720586C (en) | 2016-06-21 |
| WO2009124638A1 (de) | 2009-10-15 |
| JP2011516511A (ja) | 2011-05-26 |
| US8399509B2 (en) | 2013-03-19 |
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