EA022032B1 - Способ получения глюкопиранозилзамещенных производных бензилбензола - Google Patents
Способ получения глюкопиранозилзамещенных производных бензилбензола Download PDFInfo
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- EA022032B1 EA022032B1 EA201200537A EA201200537A EA022032B1 EA 022032 B1 EA022032 B1 EA 022032B1 EA 201200537 A EA201200537 A EA 201200537A EA 201200537 A EA201200537 A EA 201200537A EA 022032 B1 EA022032 B1 EA 022032B1
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- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title description 9
- 238000000034 method Methods 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 65
- 239000002904 solvent Substances 0.000 claims description 57
- 239000003960 organic solvent Substances 0.000 claims description 55
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 54
- 239000012074 organic phase Substances 0.000 claims description 52
- 239000011541 reaction mixture Substances 0.000 claims description 50
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 42
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 42
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000007864 aqueous solution Substances 0.000 claims description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- -1 where O is C1 Inorganic materials 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
- 239000008346 aqueous phase Substances 0.000 claims description 20
- 150000007513 acids Chemical class 0.000 claims description 19
- 230000003993 interaction Effects 0.000 claims description 19
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 18
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 18
- 150000002902 organometallic compounds Chemical class 0.000 claims description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 17
- 239000012071 phase Substances 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- 229960003681 gluconolactone Drugs 0.000 claims description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 14
- 235000011054 acetic acid Nutrition 0.000 claims description 14
- 235000012209 glucono delta-lactone Nutrition 0.000 claims description 14
- 125000005640 glucopyranosyl group Chemical group 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 13
- 229910052749 magnesium Inorganic materials 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 12
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 12
- 235000015165 citric acid Nutrition 0.000 claims description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 11
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 7
- 239000011975 tartaric acid Substances 0.000 claims description 7
- 235000002906 tartaric acid Nutrition 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910017604 nitric acid Inorganic materials 0.000 claims description 6
- 150000002900 organolithium compounds Chemical class 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 235000006408 oxalic acid Nutrition 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 4
- 229910001623 magnesium bromide Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000007818 Grignard reagent Substances 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 229940106681 chloroacetic acid Drugs 0.000 claims description 2
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- TWWGISCROAUKTE-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)C(O)C(O)=O TWWGISCROAUKTE-UHFFFAOYSA-N 0.000 claims 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 1
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 43
- 239000000047 product Substances 0.000 description 35
- 230000002829 reductive effect Effects 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 19
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 16
- 239000000543 intermediate Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 238000004817 gas chromatography Methods 0.000 description 14
- 150000002576 ketones Chemical class 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- 238000004566 IR spectroscopy Methods 0.000 description 12
- 239000003638 chemical reducing agent Substances 0.000 description 12
- 230000008901 benefit Effects 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 229960004106 citric acid Drugs 0.000 description 10
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 10
- 239000002841 Lewis acid Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 9
- 229940011051 isopropyl acetate Drugs 0.000 description 9
- 150000007517 lewis acids Chemical class 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 8
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 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 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 6
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 6
- 238000005191 phase separation Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229960001367 tartaric acid Drugs 0.000 description 6
- 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 5
- 238000003109 Karl Fischer titration Methods 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 4
- 239000000182 glucono-delta-lactone Substances 0.000 description 4
- 229940093915 gynecological organic acid Drugs 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 229940116315 oxalic acid Drugs 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000001103 potassium chloride Substances 0.000 description 4
- 235000011164 potassium chloride Nutrition 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 239000012062 aqueous buffer Substances 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940032330 sulfuric acid Drugs 0.000 description 3
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- ZOFJBHYCGASUQK-UHFFFAOYSA-N sodium;trimethylsilylazanide Chemical compound [Na+].C[Si](C)(C)[NH-] ZOFJBHYCGASUQK-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 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
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- ZHOVAWFVVBWEGQ-UHFFFAOYSA-N tripropylsilane Chemical compound CCC[SiH](CCC)CCC ZHOVAWFVVBWEGQ-UHFFFAOYSA-N 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- 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
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- 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
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Packaging Of Annular Or Rod-Shaped Articles, Wearing Apparel, Cassettes, Or The Like (AREA)
- Wrapping Of Specific Fragile Articles (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24714409P | 2009-09-30 | 2009-09-30 | |
| PCT/EP2010/064120 WO2011039108A2 (en) | 2009-09-30 | 2010-09-24 | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201200537A1 EA201200537A1 (ru) | 2012-11-30 |
| EA022032B1 true EA022032B1 (ru) | 2015-10-30 |
Family
ID=43736212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201200537A EA022032B1 (ru) | 2009-09-30 | 2010-09-24 | Способ получения глюкопиранозилзамещенных производных бензилбензола |
Country Status (25)
Families Citing this family (80)
| Publication number | Priority date | Publication date | Assignee | Title |
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| IL218714A (en) * | 2004-03-16 | 2013-02-28 | Boehringer Ingelheim Int | Glucopyranosyl-substituted benzol derivatives, drugs containing said compounds, the use thereof and method for the production thereof |
| UA91546C2 (uk) * | 2005-05-03 | 2010-08-10 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ |
| US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| AU2006289093A1 (en) * | 2005-09-08 | 2007-03-15 | Boehringer Ingelheim International Gmbh | Crystalline forms of 1-chloro-4-(beta-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene, methods for its preparation and the use thereof for preparing medicaments |
| PE20080697A1 (es) | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| WO2008049923A1 (en) * | 2006-10-27 | 2008-05-02 | Boehringer Ingelheim International Gmbh | CRYSTALLINE FORM OF 4-(ß-D-GLUCOPYRANOS-1-YL)-1-METHYL-2-[4-((S)-TETRAHYDROFURAN-3-YLOXY)-BENZYL]-BENZENE, A METHOD FOR ITS PREPARATION AND THE USE THEREOF FOR PREPARING MEDICAMENTS |
| CL2008002427A1 (es) | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende 1-cloro-4-(b-d-glucopiranos-1-il)-2-[4-((s)-tetrahidrofurano-3-iloxi)bencil]-benceno combinado con 1-[(4-metilquinazolin-2-il)metil]-3-metil-7-(2-butin-1-il)-8-(3-(r)-aminopiperidin-1-il)xantina; y su uso para tratar diabetes mellitus tipo 2. |
| WO2009068617A1 (en) | 2007-11-30 | 2009-06-04 | Boehringer Ingelheim International Gmbh | 1, 5-dihydro-pyrazolo (3, 4-d) pyrimidin-4-one derivatives and their use as pde9a modulators for the teatment of cns disorders |
| UA105362C2 (en) | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| MX2011002340A (es) | 2008-09-08 | 2011-04-04 | Boehringer Ingelheim Int | Pirazolopirimidinas y su uso para el tratamiento de trastornos del snc. |
| MX344264B (es) | 2009-02-13 | 2016-12-09 | Boehringer Ingelheim Int Gmbh * | Inhibidor de sglt-2 para el tratamiento de diabetes mellitus tipo 1, diabetes mellitus tipo 2, tolerancia deteriorada a la glucosa o hiperglucemia. |
| JP5685550B2 (ja) | 2009-02-13 | 2015-03-18 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｓｇｌｔ２阻害剤、ｄｐｐ−ｉｖ阻害剤、更に必要により抗糖尿病薬を含む医薬組成物及びその使用 |
| BRPI1011533A2 (pt) | 2009-03-31 | 2016-03-29 | Boehringer Ingelheim Int | derivados de 1-heterocicil-1 5- diidro-pirazolo [3,4--d] pirimidin-4-ona e seu uso como moduladores de pde9a. |
| AU2010303123B2 (en) | 2009-09-30 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Method for the preparation of a crystalline form of 1-chloro-4- (Beta-D-glucopyranos-1-yl)-2-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)benzene |
| HUE026133T2 (en) | 2009-09-30 | 2016-05-30 | Boehringer Ingelheim Int | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives |
| UY32919A (es) | 2009-10-02 | 2011-04-29 | Boehringer Ingelheim Int | Composición farmacéutica, forma de dosificación farmacéutica, procedimiento para su preparación, mé todos para su tratamiento y sus usos |
| AP2012006631A0 (en) | 2010-08-12 | 2012-12-31 | Boehringer Ingelheim Int | 6-Cycloalkyl-1, 5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivatives and their use as PDE9A inhibitors |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| UY33937A (es) | 2011-03-07 | 2012-09-28 | Boehringer Ingelheim Int | Composiciones farmacéuticas que contienen inhibidores de dpp-4 y/o sglt-2 y metformina |
| EA201301354A1 (ru) | 2011-06-03 | 2014-05-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Ингибиторы sglt-2, предназначенные для лечения метаболических нарушений у пациентов, леченных нейролептиками |
| US20130035298A1 (en) | 2011-07-08 | 2013-02-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| US9192617B2 (en) | 2012-03-20 | 2015-11-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US9193751B2 (en) | 2012-04-10 | 2015-11-24 | Theracos, Inc. | Process for the preparation of benzylbenzene SGLT2 inhibitors |
| WO2013152476A1 (en) * | 2012-04-10 | 2013-10-17 | Theracos, Inc. | Process for the preparation of benzylbenzene sglt2 inhibitors |
| FI2981269T3 (fi) | 2013-04-04 | 2023-09-27 | Boehringer Ingelheim Vetmedica Gmbh | Aineenvaihduntahäiriöiden hoito hevoseläimillä |
| HK1215398A1 (zh) | 2013-04-05 | 2016-08-26 | 勃林格殷格翰国际有限公司 | 依帕列净的治疗用途 |
| CA2812519A1 (en) | 2013-04-05 | 2014-10-05 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US20140303097A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| PT2986304T (pt) | 2013-04-18 | 2022-02-25 | Boehringer Ingelheim Int | Composição farmacêutica, métodos para o tratamento e suas utilizações |
| ES2605886T3 (es) | 2013-09-27 | 2017-03-16 | Sunshine Lake Pharma Co., Ltd. | Derivados de glucopiranosilo y sus usos en medicina |
| WO2015091313A1 (en) | 2013-12-17 | 2015-06-25 | Boehringer Ingelheim Vetmedica Gmbh | Treatment of metabolic disorders in feline animals |
| WO2015101916A1 (en) | 2013-12-30 | 2015-07-09 | Mylan Laboratories Ltd. | Process for the preparation of empagliflozin |
| CN115282284A (zh) | 2014-01-23 | 2022-11-04 | 勃林格殷格翰动物保健有限公司 | 犬科动物中代谢紊乱的治疗 |
| EP3721882B1 (en) | 2014-04-01 | 2024-08-28 | Boehringer Ingelheim Vetmedica GmbH | Treatment of pituitary pars intermedia dysfunction in equine animals |
| MX388192B (es) | 2014-09-25 | 2025-03-19 | Boehringer Ingelheim Vetmedica Gmbh | Tratamiento de combinación y/o prevención de trastornos metabólicos en animales equinos. |
| US10053535B2 (en) | 2016-01-04 | 2018-08-21 | National Technology & Engineering Solutions Of Sandia, Llc | Poly(phenylene)-based anion exchange polymers and methods thereof |
| JP2019500477A (ja) | 2016-01-04 | 2019-01-10 | ナショナル テクノロジー アンド エンジニアリング ソリューションズ オブ サンディア， エルエルシー | ディールスアルダーポリフェニレンポリマーの官能化 |
| US10294325B2 (en) | 2016-01-04 | 2019-05-21 | National Technology & Engineering Solutions Of Sandia, Llc | Halo-containing anion exchange membranes and methods thereof |
| JP2019530722A (ja) * | 2016-10-13 | 2019-10-24 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | グルコピラノシル置換ベンジル−ベンゼン誘導体を調製するための方法 |
| KR20190070956A (ko) | 2016-10-19 | 2019-06-21 | 베링거 인겔하임 인터내셔날 게엠베하 | Ssao/vap-1 억제제 및 sglt2 억제제를 포함하는 복합제제 및 이의 용도 |
| MA46742A (fr) | 2016-11-10 | 2019-09-18 | Boehringer Ingelheim Int | Composition pharmaceutique, méthodes de traitement et leurs utilisations |
| CN108794548B (zh) * | 2017-04-28 | 2023-06-16 | 正大天晴药业集团股份有限公司 | 制备恩格列净及其中间体的方法 |
| US11046676B2 (en) | 2017-06-05 | 2021-06-29 | Laurus Labs Limited | Process for preparation of empagliflozin or its co-crystals, solvates and their polymorphs thereof |
| CN107163033A (zh) * | 2017-06-15 | 2017-09-15 | 扬子江药业集团北京海燕药业有限公司 | 一种高纯度依帕列净的制备方法 |
| CN109988161A (zh) * | 2017-12-29 | 2019-07-09 | 徐州万邦金桥制药有限公司 | 一种适合工业化生产恩格列净的制备方法 |
| CN108178751A (zh) * | 2018-01-30 | 2018-06-19 | 扬州工业职业技术学院 | 一种恩格列净中间体的合成方法 |
| US10479866B1 (en) | 2018-02-28 | 2019-11-19 | National Technology & Engineering Solutions Of Sandia, Llc | Block copolymers including poly(phenylene) and methods thereof |
| EP3781166A1 (en) | 2018-04-17 | 2021-02-24 | Boehringer Ingelheim International GmbH | Pharmaceutical composition, methods for treating and uses thereof |
| EP3826642B8 (en) | 2018-07-25 | 2025-06-11 | Boehringer Ingelheim International GmbH | Empagliflozin for use in treating alport syndrome |
| WO2020039394A1 (en) | 2018-08-24 | 2020-02-27 | Novartis Ag | New drug combinations |
| CN109456314A (zh) * | 2018-10-19 | 2019-03-12 | 威海迪素制药有限公司 | 一种恩格列净的制备方法 |
| CN112955214B (zh) | 2018-10-29 | 2024-05-07 | 勃林格殷格翰国际有限公司 | 吡啶基磺酰胺衍生物、药物组合物及其用途 |
| BR112021004635A2 (pt) | 2018-10-29 | 2021-05-25 | Boehringer Ingelheim International Gmbh | derivados de piridinil sulfonamida, composições farmacêuticas e usos das mesmas |
| CN111233915B (zh) * | 2018-11-28 | 2023-09-22 | 上海科胜药物研发有限公司 | 一种2,3,4,6-四-o-三甲基硅基-d-葡萄糖酸内酯的制备方法 |
| CN110655511B (zh) * | 2019-05-31 | 2020-10-16 | 北京莱瑞森医药科技有限公司 | 一种高纯度恩格列净的制备和精制方法 |
| CN112812107B (zh) * | 2019-11-18 | 2024-03-15 | 上海启讯医药科技有限公司 | 一种sglt-2抑制剂及中间体的制备方法 |
| CA3158368A1 (en) | 2019-11-28 | 2021-06-03 | Boehringer Ingelheim Vetmedica Gmbh | Use of sglt-2 inhibitors in the drying-off of non-human mammals |
| CN110759941B (zh) * | 2019-11-29 | 2022-08-30 | 上海网义化工有限公司 | 一种D-葡萄糖酸-γ-内酯及其中间体的制备方法 |
| CN110872216A (zh) * | 2019-12-06 | 2020-03-10 | 南京恒道医药科技有限公司 | 一种反应分离耦合生产(2-氯-5-碘苯基)-4-氟苯甲基酮的方法及装置 |
| CN110903315A (zh) * | 2019-12-16 | 2020-03-24 | 上海网义化工有限公司 | 一种D-葡萄糖酸-γ-内酯中间体的制备方法 |
| CN118615450A (zh) | 2020-02-17 | 2024-09-10 | 勃林格殷格翰动物保健有限公司 | Sglt-2抑制剂用于预防和/或治疗猫科动物的心脏疾病的用途 |
| US20230110193A1 (en) | 2020-04-07 | 2023-04-13 | Boehringer Ingelheim International Gmbh | Methods for the treatment of headache disorders |
| CN111410639B (zh) * | 2020-04-14 | 2021-02-26 | 天津法莫西医药科技有限公司 | 一种恩格列净中间体杂质的制备方法 |
| CN112194655B (zh) * | 2020-10-15 | 2022-08-09 | 通化东宝药业股份有限公司 | 一种恩格列净的制备方法 |
| KR20220068805A (ko) | 2020-11-19 | 2022-05-26 | 한미약품 주식회사 | 신규한 글루코스 유도체 |
| CN113480497B (zh) * | 2021-07-27 | 2023-02-28 | 山东铂源药业股份有限公司 | 一种恩格列净关键中间体的合成方法 |
| US20240269105A1 (en) | 2021-07-28 | 2024-08-15 | Boehringer Ingelheim Vetmedica Gmbh | Use of sglt-2 inhibitors for the prevention and/or treatment of hypertension in non-human mammals |
| MX2024001184A (es) | 2021-07-28 | 2024-02-27 | Boehringer Ingelheim Vetmedica Gmbh | Uso de inhibidores de sglt-2 para la prevencion y/o tratamiento de cardiopatias en mamiferos no humanos, que excluye felinos, en particular, caninos. |
| CA3224673A1 (en) | 2021-07-28 | 2023-02-02 | Boehringer Ingelheim Vetmedica Gmbh | Use of sglt-2 inhibitors for the prevention and/or treatment of renal diseases in non-human mammals |
| CN114716425B (zh) * | 2022-04-11 | 2023-09-01 | 沧州那瑞化学科技有限公司 | 芳香杂环取代亚甲基的化合物的合成方法 |
| CN119110722A (zh) | 2022-05-25 | 2024-12-10 | 勃林格殷格翰动物保健有限公司 | 包含sglt-2抑制剂的水性医药组合物 |
| CN115231992B (zh) * | 2022-06-30 | 2024-08-27 | 济南鼎皓医药科技有限公司 | 一种(2-氯-5-碘苯基)(4-氟苯基)甲酮的制备方法 |
| CN115232179A (zh) * | 2022-08-15 | 2022-10-25 | 江西天戌药业有限公司 | 一种恩格列净中间体杂质的制备方法 |
| AR132054A1 (es) | 2023-03-06 | 2025-05-21 | Boehringer Ingelheim Vetmedica Gmbh | Sistemas y métodos para la administración de composiciones farmacéuticas líquidas, en particular que comprenden uno o más inhibidores de sglt-2 |
| CN121218995A (zh) | 2023-05-24 | 2025-12-26 | 勃林格殷格翰动物保健有限公司 | 包含一或多种sglt-2抑制剂及匹莫苯丹和/或替米沙坦的非人类哺乳动物中心脏疾病的组合治疗和/或预防 |
| TW202508455A (zh) | 2023-05-24 | 2025-03-01 | 德商百靈佳殷格翰維美迪加股份有限公司 | 包含一或多種sglt-2抑制劑及替米沙坦(telmisartan)之非人類哺乳動物之腎臟疾病及/或高血壓之組合治療及/或預防 |
| CN116715569A (zh) * | 2023-05-26 | 2023-09-08 | 雅邦绿色过程与新材料研究院南京有限公司 | 一种4,4’-二氟二苯甲酮的制备方法 |
| WO2025191117A1 (en) | 2024-03-15 | 2025-09-18 | Inventiva | Prevention of blood disorders in patient treated with a ppar agonist |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006120208A1 (en) * | 2005-05-10 | 2006-11-16 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| US20080287529A1 (en) * | 2007-05-18 | 2008-11-20 | Bristol-Myers Squibb Company | Crystal structures of sglt2 inhibitors and processes for preparing same |
| WO2009035969A1 (en) * | 2007-09-10 | 2009-03-19 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of sglt |
Family Cites Families (151)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3174901A (en) * | 1963-01-31 | 1965-03-23 | Jan Marcel Didier Aron Samuel | Process for the oral treatment of diabetes |
| NL167151C (nl) * | 1971-04-09 | 1981-11-16 | Acf Chemiefarma Nv | Werkwijze ter bereiding van geneesmiddelen met anti-parasitaire werking op basis van halogeen bevatten- de 2,2'-methyleendifenolderivaten, alsmede werkwijze ter bereiding van deze geneeskrachtige verbindingen. |
| DE2758025A1 (de) | 1977-12-24 | 1979-07-12 | Bayer Ag | Neue derivate von 3,4,5-trihydroxypiperidin, verfahren zu ihrer herstellung und ihre verwendung |
| NO154918C (no) * | 1977-08-27 | 1987-01-14 | Bayer Ag | Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. |
| DE2951135A1 (de) * | 1979-12-19 | 1981-06-25 | Hoechst Ag, 6230 Frankfurt | Sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| JPS5639056A (en) | 1980-07-16 | 1981-04-14 | Kanebo Ltd | Preparation of n,n,n',n'-tetraacylated nucleus halogenated aromatic diamine |
| JPS58164502A (ja) | 1982-03-26 | 1983-09-29 | Chugai Pharmaceut Co Ltd | 除草用組成物 |
| US4786755A (en) * | 1985-06-03 | 1988-11-22 | Warner-Lambert Company | Diphenic acid monoamides |
| US4602023A (en) | 1985-06-03 | 1986-07-22 | Warner-Lambert Company | Diphenic acid monoamides |
| US4786023A (en) * | 1987-08-19 | 1988-11-22 | Harris Leverett D | Drafting implement holder |
| US6297273B1 (en) | 1996-04-02 | 2001-10-02 | Mars, Inc. | Use of cocoa solids having high cocoa polyphenol content in tabletting compositions and capsule filling compositions |
| JPH1085502A (ja) | 1996-09-19 | 1998-04-07 | Konica Corp | 晶析方法 |
| WO1998031697A1 (en) | 1997-01-15 | 1998-07-23 | Sankyo Company, Limited | Aryl c-glycoside compounds and sulfated esters thereof |
| JPH11124392A (ja) | 1997-10-21 | 1999-05-11 | Sankyo Co Ltd | Ｃ−グリコシル化されたアリールスズ化合物 |
| DE19846314A1 (de) | 1998-10-08 | 2000-04-13 | Basf Ag | Polyolefinnanocomposite |
| US6613806B1 (en) * | 1999-01-29 | 2003-09-02 | Basf Corporation | Enhancement of the efficacy of benzoylbenzenes |
| DK1213296T3 (da) | 1999-08-31 | 2004-08-16 | Kissei Pharmaceutical | Glucopyranosyloxpyrazolderivater, lægemidler indeholdende samme samt mellemprodukter til fremstilling heraf |
| PH12000002657B1 (en) * | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| US6515117B2 (en) | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| US6498193B2 (en) | 1999-12-22 | 2002-12-24 | Trustees Of Dartmouth College | Treatment for complications of type 2 diabetes |
| JP4456768B2 (ja) | 2000-02-02 | 2010-04-28 | 壽製薬株式会社 | Ｃ−配糖体を含有する薬剤 |
| US6627611B2 (en) * | 2000-02-02 | 2003-09-30 | Kotobuki Pharmaceutical Co Ltd | C-glycosides and preparation of thereof as antidiabetic agents |
| EP1270584B1 (en) * | 2000-03-17 | 2005-12-07 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxy benzylbenzene derivatives, medicinal compositions containing the same and intermediates for the preparation of the derivatives |
| US6683056B2 (en) | 2000-03-30 | 2004-01-27 | Bristol-Myers Squibb Company | O-aryl glucoside SGLT2 inhibitors and method |
| SK287811B6 (sk) * | 2000-09-29 | 2011-10-04 | Kissei Pharmaceutical Co., Ltd | Glukopyranozyloxybenzylbenzénový derivát, farmaceutická kompozícia a ľudský SGLT2-inhibítor tento derivát obsahujúci a použitie tohto derivátu |
| AU2002223127A1 (en) | 2000-11-30 | 2002-06-11 | Kissei Pharmaceutical Co., Ltd. Intellectual Property | Glucopyranosyloxybenzyl benzene derivatives, medicinal compositions containing the same and intermediates in the production thereof |
| TWI255817B (en) | 2001-02-14 | 2006-06-01 | Kissei Pharmaceutical | Glucopyranosyloxybenzylbenzene derivatives and medicinal use thereof |
| EP1360172A1 (en) | 2001-02-15 | 2003-11-12 | Pfizer Products Inc. | Ppar agonists |
| US6936590B2 (en) * | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| JP3698067B2 (ja) * | 2001-03-30 | 2005-09-21 | Ｊｓｒ株式会社 | 電子吸引性基および電子供与性基を有するモノマー、それを用いた共重合体、ならびにプロトン伝導膜 |
| JP2004536047A (ja) | 2001-04-11 | 2004-12-02 | ブリストル−マイヤーズ スクイブ カンパニー | 糖尿病処置用ｃ−アリールグルコシドのアミノ酸複合体および方法 |
| DE10139416A1 (de) | 2001-08-17 | 2003-03-06 | Aventis Pharma Gmbh | Aminoalkyl substituierte aromatische Bicyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US20030087843A1 (en) * | 2001-09-05 | 2003-05-08 | Washburn William N. | O-pyrazole glucoside SGLT2 inhibitors and method of use |
| WO2003031458A1 (en) | 2001-10-12 | 2003-04-17 | Dana-Farber Cancer Institute | Methods for synthesis of diarylmethanes |
| JP4597524B2 (ja) | 2002-02-01 | 2010-12-15 | ハイ・ポイント・ファーマスーティカルズ、エルエルシー | アミノアルキル置換されたアゼチジン、ピロリジン、ピペリジン、およびアゼパンのアミド |
| GB0206215D0 (en) | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
| DE10231370B4 (de) | 2002-07-11 | 2006-04-06 | Sanofi-Aventis Deutschland Gmbh | Thiophenglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| TWI254635B (en) | 2002-08-05 | 2006-05-11 | Yamanouchi Pharma Co Ltd | Azulene derivative and salt thereof |
| DE60332743D1 (de) * | 2002-08-08 | 2010-07-08 | Kissei Pharmaceutical | Pyrazolderivat, dieses enthaltende medizinische zusammensetzung, medizinische verwendung davon, und zwischenprodukt für dessen herstellung |
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| KR101150449B1 (ko) | 2002-08-21 | 2012-06-01 | 베링거 잉겔하임 파르마 게엠베하 운트 코 카게 | 8-［3-아미노-피페리딘-1-일］-크산틴, 이의 제조방법 및 이를 포함하는 약제학적 조성물 |
| EP3406596A1 (en) | 2002-11-20 | 2018-11-28 | Japan Tobacco Inc. | 4-oxoquinoline compound and use thereof as hiv integrase inhibitor |
| JP3567162B1 (ja) | 2002-11-20 | 2004-09-22 | 日本たばこ産業株式会社 | ４−オキソキノリン化合物及びそのｈｉｖインテグラーゼ阻害剤としての利用 |
| JP4651934B2 (ja) | 2002-12-04 | 2011-03-16 | キッセイ薬品工業株式会社 | ベンジルフェノール誘導体、それを含有する医薬組成物およびその医薬用途 |
| DE10258008B4 (de) | 2002-12-12 | 2006-02-02 | Sanofi-Aventis Deutschland Gmbh | Heterocyclische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| DE10258007B4 (de) | 2002-12-12 | 2006-02-09 | Sanofi-Aventis Deutschland Gmbh | Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| BR0317929A (pt) | 2003-01-03 | 2006-04-11 | Bristol Myers Squibb Co | métodos de produzir inibidores de sglt2 de glicosìdeo de c-arila |
| WO2004076470A2 (en) | 2003-02-27 | 2004-09-10 | Bristol-Myers Squibb Company | A non-cryogenic process for forming glycosides |
| KR101001848B1 (ko) | 2003-03-14 | 2010-12-17 | 고토부키 세이야쿠 가부시키가이샤 | Ｃ-글리코시드 유도체 또는 이의 염, 및 이를 포함하는 의약 조성물 |
| US7674486B2 (en) | 2003-05-14 | 2010-03-09 | Indus Biotech Pvt. Ltd. | Synergistic composition for the treatment of diabetes mellitus |
| EP1664073A2 (en) * | 2003-06-03 | 2006-06-07 | The Regents of the University of California | Compositions and methods for treatment of disease with acetylated disaccharides |
| JP2004359630A (ja) | 2003-06-06 | 2004-12-24 | Yamanouchi Pharmaceut Co Ltd | ジフルオロジフェニルメタン誘導体及びその塩 |
| WO2005012318A2 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica Nv | Substituted fused heterocyclic c-glycosides |
| CN103214471B (zh) | 2003-08-01 | 2018-02-06 | 田边三菱制药株式会社 | 具有钠依赖型葡萄糖转运体抑制活性的化合物的制备方法 |
| EA010655B1 (ru) | 2003-08-01 | 2008-10-30 | Янссен Фармацевтика Н.В. | Замещенные индазол-о-глюкозиды |
| JP4131216B2 (ja) | 2003-08-20 | 2008-08-13 | Ｊｓｒ株式会社 | ポリアリーレンおよびその製造方法、ならびに高分子固体電解質およびプロトン伝導膜 |
| ATE422204T1 (de) | 2003-08-26 | 2009-02-15 | Boehringer Ingelheim Int | Glucopyranosyloxy-pyrazole, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| US7375090B2 (en) * | 2003-08-26 | 2008-05-20 | Boehringer Ingelheim International Gmbh | Glucopyranosyloxy-pyrazoles, pharmaceutical compositions containing these compounds, the use thereof and processed for the preparation thereof |
| US20050085680A1 (en) * | 2003-10-21 | 2005-04-21 | Joseph Auerbach | Method for industrial decontamination |
| US7371732B2 (en) * | 2003-12-22 | 2008-05-13 | Boehringer Ingelheim International Gmbh | Glucopyranosyloxy-substituted aromatic compounds, medicaments containing such compounds, their use and process for their manufacture |
| DE10361133A1 (de) | 2003-12-22 | 2005-07-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Glucopyranosyloxy-substituierte Aromaten, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| WO2005085237A1 (ja) | 2004-03-04 | 2005-09-15 | Kissei Pharmaceutical Co., Ltd. | 縮合複素環誘導体、それを含有する医薬組成物およびその医薬用途 |
| ZA200606792B (en) | 2004-03-04 | 2007-12-27 | Kissei Pharmaceutical | Fused heterocycle derivative, medicinal composition containing the same, and medicinal use thereof |
| IL218714A (en) * | 2004-03-16 | 2013-02-28 | Boehringer Ingelheim Int | Glucopyranosyl-substituted benzol derivatives, drugs containing said compounds, the use thereof and method for the production thereof |
| DE102004012676A1 (de) * | 2004-03-16 | 2005-10-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Glucopyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| US7393836B2 (en) | 2004-07-06 | 2008-07-01 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture |
| JPWO2006006496A1 (ja) | 2004-07-08 | 2008-04-24 | アステラス製薬株式会社 | アズレン誘導体の製造方法及びその合成中間体 |
| DE102004034690A1 (de) * | 2004-07-17 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Methyliden-D-xylopyranosyl-und Oxo-D-xylopyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| 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 |
| CA2574451A1 (en) | 2004-07-27 | 2006-02-02 | Boehringer Ingelheim International Gmbh | D-glucopyranosyl phenyl-substituted cyclene, medicaments containing these compounds, their use, and method for the production thereof |
| WO2006018150A1 (de) | 2004-08-11 | 2006-02-23 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-phenyl-substituierte cyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| AR051446A1 (es) | 2004-09-23 | 2007-01-17 | Bristol Myers Squibb Co | Glucosidos de c-arilo como inhibidores selectivos de transportadores de glucosa (sglt2) |
| MX2007003785A (es) | 2004-09-29 | 2007-07-12 | Kissei Pharmaceutical | Compuesto heterociclico nitrogenoso 1-(b-d-glicopiranosil)-3, composicion medicinal que contiene el mismo, y uso medicinal del mismo. |
| DE102004048388A1 (de) * | 2004-10-01 | 2006-04-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | D-Pyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| TW200635599A (en) * | 2004-12-16 | 2006-10-16 | Boehringer Ingelheim Int | Glucopyranosyl-substituted benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
| JP2006176443A (ja) | 2004-12-22 | 2006-07-06 | Shionogi & Co Ltd | メラニン凝集ホルモン受容体アンタゴニスト |
| GB0428180D0 (en) * | 2004-12-23 | 2005-01-26 | Biopartners Ltd | Combination therapy |
| GT200600008A (es) | 2005-01-18 | 2006-08-09 | Formulacion de compresion directa y proceso | |
| DE602006009772D1 (de) | 2005-02-23 | 2009-11-26 | Boehringer Ingelheim Int | Glucopyranosylsubstituierte ((hetero)arylethynyl-benzyl)-benzenderivative und deren verwendung als inhibitoren des natriumabhängigen glucose-cotransporters typ 2 (sglt2) |
| CA2605245A1 (en) * | 2005-04-15 | 2006-10-19 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted (heteroaryloxy-benzyl)-benzene derivatives as sglt inhibitors |
| US7723309B2 (en) | 2005-05-03 | 2010-05-25 | Boehringer Ingelheim International Gmbh | Crystalline forms of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments |
| UA91546C2 (uk) | 2005-05-03 | 2010-08-10 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ |
| WO2007000445A1 (en) * | 2005-06-29 | 2007-01-04 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
| EP1910390B1 (en) | 2005-07-27 | 2010-05-19 | Boehringer Ingelheim International GmbH | Glucopyranosyl-substituted ((hetero)cycloalyklethynyl-benzyl)-benzene derivatives and use thereof as sodium-dependent glucose cotransporter (sglt) inhibitors |
| KR100780553B1 (ko) | 2005-08-18 | 2007-11-29 | 한올제약주식회사 | 메트포르민 서방정 및 그의 제조방법 |
| US7452872B2 (en) | 2005-08-24 | 2008-11-18 | Salix Pharmaceuticals, Inc. | Formulations and uses of 2-hydroxy-5-phenylazobenzoic acid derivatives |
| ATE484499T1 (de) | 2005-08-30 | 2010-10-15 | Boehringer Ingelheim Int | Glucopyranosyl-substituierte benzyl-derivate, medikamente mit solchen verbindungen, ihre verwendung und herstellungsverfahren dafür |
| AU2006289093A1 (en) | 2005-09-08 | 2007-03-15 | Boehringer Ingelheim International Gmbh | Crystalline forms of 1-chloro-4-(beta-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene, methods for its preparation and the use thereof for preparing medicaments |
| AR056195A1 (es) | 2005-09-15 | 2007-09-26 | Boehringer Ingelheim Int | Procedimientos para preparar derivados de (etinil-bencil)-benceno sustituidos de glucopiranosilo y compuestos intermedios de los mismos |
| JOP20180109A1 (ar) | 2005-09-29 | 2019-01-30 | Novartis Ag | تركيبة جديدة |
| NZ567627A (en) | 2005-09-30 | 2011-08-26 | Boehringer Ingelheim Vetmed | Granulation process for making a divisible tablet containing meloxicam |
| BRPI0707849A2 (pt) * | 2006-02-15 | 2011-05-10 | Boehringer Ingelheim Int | derivados de benzonitrila substituÍdos por glicopiranosila, composiÇÕes farmacÊuticas contendo tais compostos, seu uso e processo para sua fabricaÇço |
| PE20080697A1 (es) | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| PE20080251A1 (es) * | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| EP2029112B2 (en) | 2006-06-16 | 2014-02-19 | LEK Pharmaceuticals d.d. | Pharmaceutical composition comprising hydrochlorothiazide and telmisartan |
| PE20120542A1 (es) | 2006-06-27 | 2012-05-14 | Novartis Ag | Formas de dosificacion solidas de valsartan, amlodipina e hidroclorotiazida y metodo para elaborarlas |
| TW200817424A (en) | 2006-08-04 | 2008-04-16 | Daiichi Sankyo Co Ltd | Benzylphenyl glucopyranoside derivatives |
| CA2656847A1 (en) * | 2006-08-15 | 2008-02-21 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted cyclopropylbenzene derivatives, pharmaceutical compositions containing such compounds, their use as sglt inhibitors and process for their manufacture |
| MX2009001763A (es) | 2006-08-17 | 2009-02-25 | Wellstat Therapeutics Corp | Tratamiento combinado para trastornos metabolicos. |
| WO2008034859A1 (en) | 2006-09-21 | 2008-03-27 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted difluorobenzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
| WO2008049923A1 (en) | 2006-10-27 | 2008-05-02 | Boehringer Ingelheim International Gmbh | CRYSTALLINE FORM OF 4-(ß-D-GLUCOPYRANOS-1-YL)-1-METHYL-2-[4-((S)-TETRAHYDROFURAN-3-YLOXY)-BENZYL]-BENZENE, A METHOD FOR ITS PREPARATION AND THE USE THEREOF FOR PREPARING MEDICAMENTS |
| WO2008055870A1 (en) | 2006-11-06 | 2008-05-15 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzyl-benzonitrile derivatives, medicaments containing such compounds, their use and process for their manufacture |
| EP2081569A2 (en) | 2006-11-09 | 2009-07-29 | Boehringer Ingelheim International GmbH | Combination therapy with sglt-2 inhibitors and their pharmaceutical compositions |
| WO2008062273A2 (en) | 2006-11-20 | 2008-05-29 | Cadila Pharmaceuticals Limited | Solid oral dosage form having antidiabetic drug combination |
| EP2114937B1 (de) | 2007-01-26 | 2011-06-29 | Sanofi-Aventis | Phenothiazin derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| TW200838549A (en) * | 2007-01-26 | 2008-10-01 | Boehringer Ingelheim Int | Methods for preventing and treating neurodegenerative disorders |
| EP2125768A1 (en) * | 2007-02-21 | 2009-12-02 | Boehringer Ingelheim International GmbH | Tetrasubstituted glucopyranosylated benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
| WO2008101938A1 (en) | 2007-02-21 | 2008-08-28 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzyl-benzonitrile derivatives, medicaments containing such compounds, their use and process for their manufacture |
| ITFI20070042A1 (it) | 2007-02-21 | 2008-08-22 | Laboratori Guidotti Spa | Formulazione farmaceutica e compressa comprendente detta formulazione. |
| TW200904454A (en) | 2007-03-22 | 2009-02-01 | Bristol Myers Squibb Co | Methods for treating obesity employing an SGLT2 inhibitor and compositions thereof |
| PE20090185A1 (es) * | 2007-03-22 | 2009-02-28 | Bristol Myers Squibb Co | Formulaciones farmaceuticas que contienen un inhibidor sglt2 |
| PE20090696A1 (es) | 2007-04-20 | 2009-06-20 | Bristol Myers Squibb Co | Formas cristalinas de saxagliptina y procesos para preparar las mismas |
| CL2008002427A1 (es) | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende 1-cloro-4-(b-d-glucopiranos-1-il)-2-[4-((s)-tetrahidrofurano-3-iloxi)bencil]-benceno combinado con 1-[(4-metilquinazolin-2-il)metil]-3-metil-7-(2-butin-1-il)-8-(3-(r)-aminopiperidin-1-il)xantina; y su uso para tratar diabetes mellitus tipo 2. |
| CL2008002425A1 (es) * | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composición farmacéutica que comprende un inhibidor de sglt2 y 1-(4-metil-quinazolin-2-il)metil-3metil-7-(-2-butin-1-il)-8-(3-(r)-amino-piperidin-1il)-xantina, un inhibidor de dpp iv y su uso para el tratamiento de la obesidad y de la diabetes tipo 1 y 2 y complicaciones de esta. |
| CL2008003653A1 (es) | 2008-01-17 | 2010-03-05 | Mitsubishi Tanabe Pharma Corp | Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica. |
| AU2009210641A1 (en) | 2008-02-05 | 2009-08-13 | Merck Sharp & Dohme Corp. | Pharmaceutical compositions of a combination of metformin and a dipeptidyl peptidase-IV inhibitor |
| US8551524B2 (en) | 2008-03-14 | 2013-10-08 | Iycus, Llc | Anti-diabetic combinations |
| WO2009123194A1 (ja) | 2008-04-01 | 2009-10-08 | 武田薬品工業株式会社 | 複素環化合物 |
| PE20091730A1 (es) | 2008-04-03 | 2009-12-10 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| WO2010045656A2 (en) | 2008-10-17 | 2010-04-22 | Nectid, Inc. | Novel sglt2 inhibitor dosage forms |
| JP5685550B2 (ja) | 2009-02-13 | 2015-03-18 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｓｇｌｔ２阻害剤、ｄｐｐ−ｉｖ阻害剤、更に必要により抗糖尿病薬を含む医薬組成物及びその使用 |
| UY32427A (es) | 2009-02-13 | 2010-09-30 | Boheringer Ingelheim Internat Gmbh | Composicion farmaceutica, forma farmaceutica, procedimiento para su preparacion, metodos de tratamiento y usos de la misma |
| HRP20240365T1 (hr) | 2009-02-13 | 2024-06-07 | Boehringer Ingelheim International Gmbh | Farmaceutski pripravak koji sadrži derivate glukopiranozil difenilmetana, njegov farmaceutski oblik za doziranje, postupak za njihovu proizvodnju i njihove uporabe za poboljšanu regulaciju glikemije kod pacijenta |
| MX344264B (es) | 2009-02-13 | 2016-12-09 | Boehringer Ingelheim Int Gmbh * | Inhibidor de sglt-2 para el tratamiento de diabetes mellitus tipo 1, diabetes mellitus tipo 2, tolerancia deteriorada a la glucosa o hiperglucemia. |
| CN102387795A (zh) | 2009-02-13 | 2012-03-21 | 贝林格尔.英格海姆国际有限公司 | 包含dpp-4抑制剂(利拉列汀)任选地组合其它抗糖尿病药的抗糖尿病药物 |
| EP2419097B1 (en) | 2009-04-16 | 2013-09-25 | Taisho Pharmaceutical Co., Ltd. | Pharmaceutical composition comprising (1s)-1,5-anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-d-glucitol and metformin and uses thereof in the treatment of diabetes |
| CN102639125A (zh) | 2009-05-27 | 2012-08-15 | 百时美施贵宝公司 | 使用sglt2抑制剂及其组合物在对先前用其它抗糖尿病药进行的治疗具有耐受的患者中治疗ii型糖尿病的方法 |
| US20110077212A1 (en) | 2009-09-25 | 2011-03-31 | Theracos, Inc. | Therapeutic uses of sglt2 inhibitors |
| HUE026133T2 (en) | 2009-09-30 | 2016-05-30 | Boehringer Ingelheim Int | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives |
| AU2010303123B2 (en) | 2009-09-30 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Method for the preparation of a crystalline form of 1-chloro-4- (Beta-D-glucopyranos-1-yl)-2-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)benzene |
| UY32919A (es) | 2009-10-02 | 2011-04-29 | Boehringer Ingelheim Int | Composición farmacéutica, forma de dosificación farmacéutica, procedimiento para su preparación, mé todos para su tratamiento y sus usos |
| MX2012005365A (es) | 2009-11-13 | 2012-05-29 | Bristol Myers Squibb Co | Formulaciones de tableta de liberacion inmediata. |
| WO2011120923A1 (en) | 2010-03-30 | 2011-10-06 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition comprising an sglt2 inhibitor and a ppar- gamma agonist and uses thereof |
| MX2013002146A (es) | 2010-09-03 | 2013-04-03 | Astrazeneca Uk Ltd | Formulaciones farmaceuticas que utilizan antioxidantes solubles en agua. |
| US20120283169A1 (en) | 2010-11-08 | 2012-11-08 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| AR083878A1 (es) | 2010-11-15 | 2013-03-27 | Boehringer Ingelheim Int | Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento |
| CN103442697A (zh) | 2011-02-01 | 2013-12-11 | 百时美施贵宝公司 | 包含胺化合物的药物制剂 |
| US20130035281A1 (en) | 2011-02-09 | 2013-02-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| UY33937A (es) | 2011-03-07 | 2012-09-28 | Boehringer Ingelheim Int | Composiciones farmacéuticas que contienen inhibidores de dpp-4 y/o sglt-2 y metformina |
| EA201301354A1 (ru) | 2011-06-03 | 2014-05-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Ингибиторы sglt-2, предназначенные для лечения метаболических нарушений у пациентов, леченных нейролептиками |
| US20130035298A1 (en) | 2011-07-08 | 2013-02-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| DE102011109492A1 (de) | 2011-08-04 | 2013-02-07 | GM Global Technology Operations LLC (n. d. Gesetzen des Staates Delaware) | Fahrunterstützungsvorrichtung zur Unterstützung der Befahrung enger Fahrwege |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| US9192617B2 (en) | 2012-03-20 | 2015-11-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| HK1215398A1 (zh) | 2013-04-05 | 2016-08-26 | 勃林格殷格翰国际有限公司 | 依帕列净的治疗用途 |
| US20140303097A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US20160000816A1 (en) | 2013-04-05 | 2016-01-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| PT2986304T (pt) | 2013-04-18 | 2022-02-25 | Boehringer Ingelheim Int | Composição farmacêutica, métodos para o tratamento e suas utilizações |
| EP3721882B1 (en) | 2014-04-01 | 2024-08-28 | Boehringer Ingelheim Vetmedica GmbH | Treatment of pituitary pars intermedia dysfunction in equine animals |
| EP3362055B1 (en) | 2015-10-15 | 2023-01-18 | Boehringer Ingelheim International GmbH | Sglt-2 inhibitor for use in the treatment of a metabolic myopathy |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006120208A1 (en) * | 2005-05-10 | 2006-11-16 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| US20080287529A1 (en) * | 2007-05-18 | 2008-11-20 | Bristol-Myers Squibb Company | Crystal structures of sglt2 inhibitors and processes for preparing same |
| WO2009035969A1 (en) * | 2007-09-10 | 2009-03-19 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of sglt |
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