ES2477216T3 - Análogos de florizina como inhibidores de SGLT2 - Google Patents
Análogos de florizina como inhibidores de SGLT2 Download PDFInfo
- Publication number
- ES2477216T3 ES2477216T3 ES10194063.3T ES10194063T ES2477216T3 ES 2477216 T3 ES2477216 T3 ES 2477216T3 ES 10194063 T ES10194063 T ES 10194063T ES 2477216 T3 ES2477216 T3 ES 2477216T3
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- Prior art keywords
- alkyl
- aryl
- heterocycle
- hydrogen
- compound according
- Prior art date
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- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 69
- 125000003118 aryl group Chemical group 0.000 claims abstract description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 8
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- -1 Xylopyranosyl-Substituted Phenyl Chemical class 0.000 description 73
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 47
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 36
- 238000000034 method Methods 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 31
- 125000003373 pyrazinyl group Chemical group 0.000 description 25
- 201000010099 disease Diseases 0.000 description 24
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 208000035475 disorder Diseases 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 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 11
- 239000002552 dosage form Substances 0.000 description 11
- 239000008103 glucose Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 229910052681 coesite Inorganic materials 0.000 description 8
- 229910052906 cristobalite Inorganic materials 0.000 description 8
- 230000014509 gene expression Effects 0.000 description 8
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 8
- 235000012239 silicon dioxide Nutrition 0.000 description 8
- 229910052682 stishovite Inorganic materials 0.000 description 8
- 229910052905 tridymite Inorganic materials 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 206010012601 diabetes mellitus Diseases 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 108091006277 SLC5A1 Proteins 0.000 description 4
- 102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- AGHNXKZBDRQJSE-TWGBQZSLSA-N (2s,3s,4r,5r,6r)-2-[3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol Chemical compound C1=CC(OCC)=CC=C1CC1=CC=CC([C@@H]2N([C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C)=C1 AGHNXKZBDRQJSE-TWGBQZSLSA-N 0.000 description 3
- IAPVMXRKLOSMDT-ODSPINPYSA-N (2s,3s,4r,5r,6r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris[(e)-prop-1-enoxy]-6-[[(e)-prop-1-enoxy]methyl]piperidine Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O\C=C\C)[C@H](O\C=C\C)[C@@H](CO\C=C\C)N2)O\C=C\C)=CC=C1Cl IAPVMXRKLOSMDT-ODSPINPYSA-N 0.000 description 3
- BQSGPTNJDRCQCQ-FYQPLNBISA-N (2s,3s,4s,5r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-trihydroxypiperidine-1-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@@H]2N(C[C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=CC=C1Cl BQSGPTNJDRCQCQ-FYQPLNBISA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- 108010078791 Carrier Proteins Proteins 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229940124639 Selective inhibitor Drugs 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000008297 liquid dosage form Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 238000002953 preparative HPLC Methods 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 229950010131 puromycin Drugs 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- PNYGUECZGOHYPH-TWGBQZSLSA-N (2s,3s,4r,5r,6r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@@H]2N([C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C)=CC=C1Cl PNYGUECZGOHYPH-TWGBQZSLSA-N 0.000 description 2
- HMNGIDFDTPKVKB-TXVWBRJLSA-N (2s,3s,4r,5r,6r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)N2)O)=CC=C1Cl HMNGIDFDTPKVKB-TXVWBRJLSA-N 0.000 description 2
- XBYVIEDJUHYNGT-SBFWRKJZSA-N (2s,3s,4s,5r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(2-methylpropyl)piperidine-3,4,5-triol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@@H]2N(C[C@@H](O)[C@H](O)[C@H]2O)CC(C)C)=CC=C1Cl XBYVIEDJUHYNGT-SBFWRKJZSA-N 0.000 description 2
- KVLUBKAVKJZBIB-FYQPLNBISA-N (2s,3s,4s,5r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]piperidine-3,4,5-triol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)CN2)O)=CC=C1Cl KVLUBKAVKJZBIB-FYQPLNBISA-N 0.000 description 2
- CVLDCIUEZOEBBY-JPEWJUICSA-N (3s,4r,5r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidine Chemical compound C1=CC(OCC)=CC=C1CC1=CC(C2N(C(COCC=3C=CC=CC=3)[C@@H](OCC=3C=CC=CC=3)[C@H](OCC=3C=CC=CC=3)[C@H]2OCC=2C=CC=CC=2)C)=CC=C1Cl CVLDCIUEZOEBBY-JPEWJUICSA-N 0.000 description 2
- YKHFKLRGSFFLLE-OYXUFCRKSA-N (3s,4r,5r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidine Chemical compound C1=CC(OCC)=CC=C1CC1=CC(C2[C@@H]([C@@H](OCC=3C=CC=CC=3)[C@H](OCC=3C=CC=CC=3)C(COCC=3C=CC=CC=3)N2)OCC=2C=CC=CC=2)=CC=C1Cl YKHFKLRGSFFLLE-OYXUFCRKSA-N 0.000 description 2
- IRIDEQXVUKKTBV-ZEEZOPKCSA-N (s)-[(3as,5s,6r,6as)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]methanol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H](O)[C@H]2[C@H]([C@@H]3OC(C)(C)O[C@@H]3O2)O[Si](C)(C)C(C)(C)C)=CC=C1Cl IRIDEQXVUKKTBV-ZEEZOPKCSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- ZUNCHZBITMUSRD-UHFFFAOYSA-N 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene Chemical compound C1=CC(OCC)=CC=C1CC1=CC(Br)=CC=C1Cl ZUNCHZBITMUSRD-UHFFFAOYSA-N 0.000 description 2
- JVHXJTBJCFBINQ-ADAARDCZSA-N Dapagliflozin Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl JVHXJTBJCFBINQ-ADAARDCZSA-N 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102100020888 Sodium/glucose cotransporter 2 Human genes 0.000 description 2
- 101710103228 Sodium/glucose cotransporter 2 Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229960003834 dapagliflozin Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
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- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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- 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
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
-
- 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
- C07D407/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
-
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Landscapes
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- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| US905714P | 2007-03-08 | ||
| US94878007P | 2007-07-10 | 2007-07-10 | |
| US948780P | 2007-07-10 |
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| TWI499414B (zh) * | 2006-09-29 | 2015-09-11 | Lexicon Pharmaceuticals Inc | 鈉與葡萄糖第２型共同運輸體（ｃｏ-ｔｒａｎｓｐｏｒｔｅｒ ２）的抑制物與其應用方法 |
| WO2008109591A1 (en) * | 2007-03-08 | 2008-09-12 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
| PT2183263E (pt) * | 2007-07-26 | 2012-01-11 | Lexicon Pharmaceuticals Inc | Processos e compostos úteis na preparação de inibidores do co-transportador 2 de glucose e sódio |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| AR072511A1 (es) | 2008-07-15 | 2010-09-01 | Theracos Inc | Derivados deuterados de bencilbenceno y metodos de uso. composicion farmaceutica. |
| TWI472521B (zh) * | 2008-07-17 | 2015-02-11 | Lexicon Pharmaceuticals Inc | （２ｓ，３ｒ，４ｒ，５ｓ，６ｒ）－２－（４－氯－３－（４－乙氧苄基）苯基）－６－（甲硫）四氫－２ｈ－哌喃－３，４，５－三醇的固體形態與其使用方法 |
| WO2011051864A1 (en) | 2009-11-02 | 2011-05-05 | Pfizer Inc. | Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives |
| AR079438A1 (es) | 2009-12-09 | 2012-01-25 | Panacea Biotec Ltd | Derivados de azucar, composiciones farmaceuticas y sus usos |
| TWI562775B (en) * | 2010-03-02 | 2016-12-21 | Lexicon Pharmaceuticals Inc | Methods of using inhibitors of sodium-glucose cotransporters 1 and 2 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| 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 |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| 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 |
| WO2012025857A1 (en) * | 2010-08-23 | 2012-03-01 | Hetero Research Foundation | Cycloalkyl methoxybenzyl phenyl pyran derivatives as sodium dependent glucose co transporter (sglt2) inhibitors |
| CN102453026A (zh) | 2010-10-27 | 2012-05-16 | 上海艾力斯医药科技有限公司 | C-芳基葡糖苷衍生物、制备方法及其应用 |
| TWI631963B (zh) * | 2011-01-05 | 2018-08-11 | 雷西肯製藥股份有限公司 | 包含鈉－葡萄糖共同輸送體１與２之抑制劑的組合物與應用方法 |
| ES2719656T3 (es) | 2011-06-01 | 2019-07-11 | Green Cross Corp | Derivados de difenilmetano novedosos como inhibidores del SGLT2 |
| AU2012264736A1 (en) | 2011-06-03 | 2013-11-28 | Boehringer Ingelheim International Gmbh | SGLT-2 inhibitors for treating metabolic disorders in patients treated with neuroleptic agents |
| AR086922A1 (es) * | 2011-06-13 | 2014-01-29 | Panacea Biotec Ltd | Derivados de 3,4,5-trihidroxi-6-(hidroximetil)tetrahidro-2h-pirano utiles para el tratamiento de diabetes y dislipidemias, composiciones farmaceuticas que los contienen y metodo para prepararlos |
| 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 |
| WO2013038429A2 (en) | 2011-09-13 | 2013-03-21 | Panacea Biotec Ltd. | Novel sglt inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| DK2925735T3 (da) * | 2012-11-20 | 2019-06-17 | Lexicon Pharmaceuticals Inc | Inhibitorer for natriumglucose-cotransporter 1 |
| RU2648467C2 (ru) | 2013-02-04 | 2018-03-26 | Тайсо Фармасьютикал Ко., Лтд. | Профилактическое или терапевтическое лекарственное средство для лечения запора |
| CN103073606B (zh) * | 2013-02-05 | 2016-05-18 | 中国医药研究开发中心有限公司 | 5’-s-(4,4’-二甲氧基三苯甲基)-2’-脱氧肌苷的合成与制备方法 |
| WO2014161836A1 (en) | 2013-04-04 | 2014-10-09 | Boehringer Ingelheim Vetmedica Gmbh | Treatment of metabolic disorders in equine animals |
| CN105828815B (zh) | 2013-12-17 | 2020-03-27 | 勃林格殷格翰动物保健有限公司 | 猫科动物中代谢紊乱的治疗 |
| ES2951127T3 (es) | 2014-01-23 | 2023-10-18 | Boehringer Ingelheim Vetmedica Gmbh | Inhibidores de SGLT2 para el tratamiento de trastornos metabólicos en animales caninos |
| AU2015239655B2 (en) | 2014-04-01 | 2019-10-24 | Boehringer Ingelheim Vetmedica Gmbh | Treatment of metabolic disorders in equine animals |
| NZ728804A (en) | 2014-09-25 | 2022-10-28 | Boehringer Ingelheim Vetmedica Gmbh | Combination treatment of sglt2 inhibitors and dopamine agonists for preventing metabolic disorders in equine animals |
| RS66325B1 (sr) | 2015-08-27 | 2025-01-31 | Boehringer Ingelheim Vetmedica Gmbh | Tečne farmaceutske kompozicije koje obuhvataju inhibitore sglt 2 |
| EP3466958B1 (en) * | 2016-05-25 | 2020-04-29 | Crystal Pharmaceutical (Suzhou) Co., Ltd. | New crystal forms of sodium-glucose co-transporter inhibitor, processes for preparation and use thereof |
| EP3528800A1 (en) | 2016-10-19 | 2019-08-28 | Boehringer Ingelheim International GmbH | Combinations comprising an ssao/vap-1 inhibitor and a sglt2 inhibitor, uses thereof |
| WO2019134667A1 (zh) | 2018-01-05 | 2019-07-11 | 南京明德新药研发股份有限公司 | 一种SGLTs抑制剂及其应用 |
| WO2019166958A1 (en) * | 2018-02-28 | 2019-09-06 | Mylan Laboratories Ltd | Process for the preparation of sotagliflozin |
| CN111989103A (zh) | 2018-04-17 | 2020-11-24 | 勃林格殷格翰国际有限公司 | 药物组合物、其治疗方法和用途 |
| US20210238170A1 (en) * | 2018-05-09 | 2021-08-05 | Janssen Pharmaceutica Nv | 5,5-Difluoro- and 5-Fluoro-5-Methyl-C-Glycoside Derivatives Useful As Dual SGLT1 / SGLT2 Modulators |
| WO2020039394A1 (en) | 2018-08-24 | 2020-02-27 | Novartis Ag | New drug combinations |
| JP7425793B2 (ja) | 2018-10-29 | 2024-01-31 | 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 | ピリジニルスルホンアミド誘導体、医薬組成物およびそれらの使用 |
| MY206745A (en) | 2018-10-29 | 2025-01-04 | Boehringer Ingelheim Int | Pyridinyl sulfonamide derivatives, pharmaceutical compositions and uses thereof |
| EP3930706B1 (en) * | 2019-03-01 | 2024-05-22 | Lexicon Pharmaceuticals, Inc. | Use of sotagliflozin for the treatment of patients with type 1 diabetes mellitus |
| EP3957634A4 (en) | 2019-07-05 | 2022-08-31 | Shangdong Danhong Pharmaceutical Co., Ltd. | CRYSTALLINE FORM OF SGLT INHIBITOR AND ITS APPLICATION |
| MX2022001029A (es) | 2019-07-26 | 2022-05-24 | Dongbao Purple Star Hangzhou Biopharmaceutical Co Ltd | Inhibidor de sglts/dpp4 y aplicación del mismo. |
| AU2020320890B2 (en) | 2019-07-26 | 2023-03-09 | Cgenetech (Suzhou, China) Co., Ltd. | SGLT2/DPP4 inhibitor and application thereof |
| EP3771480A1 (en) * | 2019-08-01 | 2021-02-03 | Lexicon Pharmaceuticals, Inc. | Continuous process for preparing the crystalline form ii of sotagliflozin |
| AU2020394498A1 (en) | 2019-11-28 | 2022-06-09 | Boehringer Ingelheim Vetmedica Gmbh | Use of SGLT-2 inhibitors in the drying-off of non-human mammals |
| AU2021222297A1 (en) | 2020-02-17 | 2022-08-04 | Boehringer Ingelheim Vetmedica Gmbh | Use of SGLT-2 inhibitors for the prevention and/or treatment of cardiac diseases in felines |
| CN111763197A (zh) * | 2020-07-08 | 2020-10-13 | 青岛大学 | 一种新型手性吲哚类化合物的合成方法 |
| EP4376819A1 (en) | 2021-07-28 | 2024-06-05 | 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. |
| US20240307426A1 (en) | 2021-07-28 | 2024-09-19 | Boehringer Ingelheim Vetmedica Gmbh | Use of sglt-2 inhibitors for the prevention and/or treatment of renal diseases in non-human mammals |
| US20230381101A1 (en) | 2022-05-25 | 2023-11-30 | Boehringer Ingelheim Vetmedica Gmbh | Aqueous pharmaceutical compositions comprising sglt-2 inhibitors |
| WO2024184293A1 (en) | 2023-03-06 | 2024-09-12 | Boehringer Ingelheim Vetmedica Gmbh | Systems for delivery of liquid pharmaceutical compositions in particular comprising one or more sglt-2 inhibitor(s) |
| US20240390317A1 (en) | 2023-05-24 | 2024-11-28 | Boehringer Ingelheim Vetmedica Gmbh | Combination treatment and/or prevention of cardiac diseases in non-human mammals comprising one or more sglt-2 inhibitors and pimobendan and/or telmisartan |
| WO2024240633A1 (en) | 2023-05-24 | 2024-11-28 | Boehringer Ingelheim Vetmedica Gmbh | Combination treatment and/or prevention of renal diseases and/or hypertension in non-human mammals comprising one or more sglt-2 inhibitors and telmisartan |
| WO2025072413A1 (en) | 2023-09-28 | 2025-04-03 | Lexicon Pharmaceuticals, Inc. | Methods of treating type 1 diabetes and kidney disease |
| WO2025076165A1 (en) | 2023-10-06 | 2025-04-10 | Lexicon Pharmaceuticals, Inc. | Methods of reducing the risk of cardiovascular events in patients with left ventricular hypertrophy |
| WO2025160910A1 (en) * | 2024-02-01 | 2025-08-07 | New Wish Biotechnology Wuxi Co., Ltd. | Indazole compound and pharmaceutical composition, preparation method and use thereof |
Family Cites Families (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870699A (en) * | 1973-03-06 | 1975-03-11 | Upjohn Co | Lincomycin analogs |
| 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 |
| WO1995016049A1 (en) | 1993-12-08 | 1995-06-15 | The Scripps Research Institute | Catalytic chemo-enzymatic asymmetric synthesis of carbohydrates |
| US6214331B1 (en) * | 1995-06-06 | 2001-04-10 | C. R. Bard, Inc. | Process for the preparation of aqueous dispersions of particles of water-soluble polymers and the particles obtained |
| JP2885191B2 (ja) | 1996-07-09 | 1999-04-19 | 日本電気株式会社 | 液晶プロジェクタ |
| JP3928197B2 (ja) | 1997-01-23 | 2007-06-13 | 住友化学株式会社 | アリール置換芳香族類の製造方法 |
| US6664399B1 (en) | 1999-09-02 | 2003-12-16 | E. I. Du Pont De Nemours & Company | Triazole linked carbohydrates |
| US6515117B2 (en) | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| PH12000002657B1 (en) | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| HUP0300057A3 (en) | 2000-03-17 | 2003-09-29 | Kissei Pharmaceutical | Glucopyranosyloxy benzylbenzene derivatives, pharmaceutical 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 |
| US6555519B2 (en) | 2000-03-30 | 2003-04-29 | Bristol-Myers Squibb Company | O-glucosylated benzamide SGLT2 inhibitors and method |
| US6653290B2 (en) | 2000-10-06 | 2003-11-25 | Bristol-Myers Squibb Company | Tumor proliferation inhibitors |
| US7053060B2 (en) | 2000-11-30 | 2006-05-30 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates in the production thereof |
| JP4035052B2 (ja) | 2000-12-28 | 2008-01-16 | キッセイ薬品工業株式会社 | グルコピラノシルオキシピラゾール誘導体及びその医薬用途 |
| US6936590B2 (en) | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| CA2444481A1 (en) | 2001-04-11 | 2002-10-24 | Bristol-Myers Squibb Company | Amino acid complexes of c-aryl glucosides for treatment of diabetes and method |
| FR2826653B1 (fr) | 2001-06-29 | 2005-10-14 | Servier Lab | Nouveaux derives de pyrido-pyrido-pyrrolo[3,2-g]pyrrolo [3,4-e]-indole et pyrido-pyrrolo[2,3-a]pyrrolo[3,4-c] carbazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JPWO2003011880A1 (ja) | 2001-07-31 | 2004-11-18 | キッセイ薬品工業株式会社 | グルコピラノシルオキシベンジルベンゼン誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
| AR034985A1 (es) | 2001-08-08 | 2004-03-24 | Takeda Chemical Industries Ltd | Compuesto biciclico; produccion y uso del mismo |
| WO2003020737A1 (en) | 2001-09-05 | 2003-03-13 | Bristol-Myers Squibb Company | O-pyrazole glucoside sglt2 inhibitors and method of use |
| US7227019B2 (en) | 2001-09-13 | 2007-06-05 | Bristol-Myers Squibb Company | Process for the preparation of rebeccamycin and analogs thereof |
| FR2831169B1 (fr) | 2001-10-22 | 2003-12-12 | Servier Lab | Nouveaux derives d'hydroxyalkyle indolocarbazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2003051830A2 (en) | 2001-12-14 | 2003-06-26 | Purdue Research Foundation | Enantiopure 4-deoxypentenosides, dihydropyrans and tetrahydropyrans and syntheses thereof |
| US6927294B1 (en) * | 2002-03-08 | 2005-08-09 | University Of Southern California | Nitrogen-containing heterocycles |
| DE10213228A1 (de) | 2002-03-25 | 2003-10-16 | Bayer Ag | Cyclopenten-Derivate |
| US6562791B1 (en) | 2002-03-29 | 2003-05-13 | Council Of Scientific And Industrial Research | Glucopyranoside, process for isolation thereof, pharmaceutical composition containing same and use thereof |
| CA2478889A1 (en) * | 2002-08-09 | 2004-02-19 | Taisho Pharmaceutical Co., Ltd. | Aryl 5-thio-.beta.-d-glucopyranoside derivatives and therapeutic agents for diabetes containing the same |
| AU2002951247A0 (en) | 2002-09-06 | 2002-09-19 | Alchemia Limited | Compounds that interact with kinases |
| FR2845996A1 (fr) | 2002-10-16 | 2004-04-23 | Servier Lab | Nouveaux derives de[3,4-a:3,4-c]carbazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2845995A1 (fr) | 2002-10-16 | 2004-04-23 | Servier Lab | Nouveaux derives de pyrrolo[3,4-c]carbazole et de pyrido[2,3-b]pyrrolo[3,4-e]indole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CA2507665A1 (en) | 2002-12-04 | 2004-06-17 | Kissei Pharmaceutical Co., Ltd. | Preventive or remedy for diseases caused by hyperglycemia |
| DE10258007B4 (de) | 2002-12-12 | 2006-02-09 | Sanofi-Aventis Deutschland Gmbh | Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| DE10258008B4 (de) | 2002-12-12 | 2006-02-02 | Sanofi-Aventis Deutschland Gmbh | Heterocyclische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| AU2003289440A1 (en) | 2002-12-25 | 2004-07-22 | Kissei Pharmaceutical Co., Ltd. | Nitrogen-containing heterocycic derivatives, medicinal compositions containing the same and medicinal use thereof |
| EP1581543A4 (en) | 2003-01-03 | 2008-03-19 | Bristol Myers Squibb Co | METHODS FOR PRODUCING SGLT2 GLYCOSIS C-ARYL INHIBITORS |
| ES2567571T3 (es) | 2003-03-14 | 2016-04-25 | Astellas Pharma Inc. | Derivados de C-glucósido y sales de los mismos |
| JPWO2004089967A1 (ja) | 2003-04-01 | 2006-07-06 | 大正製薬株式会社 | ヘテロアリール５−チオ−β−Ｄ−グルコピラノシド誘導体及びそれを含有する糖尿病治療薬 |
| 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 |
| UA86042C2 (en) | 2003-08-01 | 2009-03-25 | Янссен Фармацевтика Н.В. | Substituted indazole-o-glucosides |
| EA011515B1 (ru) | 2003-08-01 | 2009-04-28 | Янссен Фармацевтика Н.В. | Замещенные бензимидазол-, бензтриазол- и бензимидазолон-о-глюкозиды |
| WO2005012243A2 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted indole-o-glucosides |
| AU2004261264A1 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted indazole-O-glucosides |
| TW200521131A (en) | 2003-08-01 | 2005-07-01 | Janssen Pharmaceutica Nv | Substituted fused heterocyclic c-glycosides |
| ES2322059T3 (es) | 2003-08-26 | 2009-06-16 | Boehringer Ingelheim International Gmbh | Glucopiranosiloxi-pirazoles, medicamentos que contienen a estos compuestos, su uso y procedimiento para su preparacion. |
| 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 |
| EP1670755A4 (en) | 2003-10-08 | 2007-02-28 | Harvard College | PYROVALERON ANALOGUE AND ITS THERAPEUTIC APPLICATIONS |
| 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 |
| DE102004017793A1 (de) | 2004-02-21 | 2005-09-08 | Biofrontera Discovery Gmbh | Trioxacarcine und deren Verwendung |
| JP2007524744A (ja) | 2004-02-24 | 2007-08-30 | ノボザイムス アクティーゼルスカブ | 液状洗剤中の酵素の安定化 |
| NZ549219A (en) | 2004-03-04 | 2010-08-27 | Kissei Pharmaceutical | Fused heterocycle derivative, medicinal composition containing the same, and medicinal use thereof |
| EP2360164A3 (de) | 2004-03-16 | 2012-01-04 | Boehringer Ingelheim International GmbH | Glucopyranosyl-substituierte Benzol-Derivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| WO2006002233A2 (en) | 2004-06-22 | 2006-01-05 | Wall, Michael, A. | Alvaradoins e-n, new antitumor and cytotoxic anthracenone g-glycosides |
| 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 |
| MX2007000209A (es) | 2004-07-08 | 2007-03-30 | Astellas Pharma Inc | Proceso para la produccion de derivados de azuleno e intermediarios para la sintesis de los mismos. |
| US8252959B2 (en) | 2004-07-08 | 2012-08-28 | Basf Se | Preparation of α-hydroxy and α-amino ketones |
| 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 |
| US20080045466A1 (en) | 2004-07-21 | 2008-02-21 | Kenji Katsuno | Progression Inhibitor For Disease Attributed To Abnormal Accumulation Of Liver Fat |
| 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 |
| JP2008508213A (ja) | 2004-07-27 | 2008-03-21 | 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 | Ｄ−グルコピラノシル−フェニル置換環状体、そのような化合物を含有する医薬品、それらの使用及びその製造方法 |
| 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 |
| DE102004046583A1 (de) | 2004-09-23 | 2006-03-30 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | D-Xylopyranosyl-phenyl-substituierte Cyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE102004039096A1 (de) | 2004-08-11 | 2006-02-23 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | D-Xylopyranosyl-phenyl-substituierte Cyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| 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 |
| CN101076372A (zh) | 2004-10-06 | 2007-11-21 | 里斯普蒂康公司 | 化合物用于预防药物诱导的细胞毒性的用途 |
| US7622451B2 (en) | 2004-11-03 | 2009-11-24 | University Of Kansas | Novobiocin analogues as neuroprotective agents and in the treatment of autoimmune disorders |
| AU2005301957B2 (en) | 2004-11-03 | 2012-02-23 | Department Of Health And Human Services | Novobiocin analogues as anticancer agents |
| TW200637839A (en) | 2005-01-07 | 2006-11-01 | Taisho Pharmaceutical Co Ltd | 1-thio-d-glucitol derivatives |
| 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) |
| KR20070116019A (ko) | 2005-03-25 | 2007-12-06 | 인스파이어 파마슈티컬스 인코퍼레이티드 | 세포골격 활성 화합물, 조성물 및 용도 |
| US20060240496A1 (en) | 2005-04-21 | 2006-10-26 | Lakshmi Anne | Immunogens, derivatives and immunoassay for ethyl glucuronide |
| 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 |
| ATE484499T1 (de) | 2005-08-30 | 2010-10-15 | Boehringer Ingelheim Int | Glucopyranosyl-substituierte benzyl-derivate, medikamente mit solchen verbindungen, ihre verwendung und herstellungsverfahren dafür |
| US8253752B2 (en) | 2006-07-20 | 2012-08-28 | Qualcomm Incorporated | Method and apparatus for encoder assisted pre-processing |
| WO2008014252A2 (en) | 2006-07-24 | 2008-01-31 | Tetralogic Pharmaceuticals Corporation | Iap inhibitors |
| TWI499414B (zh) * | 2006-09-29 | 2015-09-11 | Lexicon Pharmaceuticals Inc | 鈉與葡萄糖第２型共同運輸體（ｃｏ-ｔｒａｎｓｐｏｒｔｅｒ ２）的抑制物與其應用方法 |
| US20080107744A1 (en) * | 2006-11-06 | 2008-05-08 | Jack Fa-De Chu | Injectable hollow tissue filler |
| WO2008109591A1 (en) | 2007-03-08 | 2008-09-12 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
| PT2183263E (pt) * | 2007-07-26 | 2012-01-11 | Lexicon Pharmaceuticals Inc | Processos e compostos úteis na preparação de inibidores do co-transportador 2 de glucose e sódio |
| US8015005B2 (en) | 2008-02-15 | 2011-09-06 | Motorola Mobility, Inc. | Method and apparatus for voice searching for stored content using uniterm discovery |
| TWI472521B (zh) | 2008-07-17 | 2015-02-11 | Lexicon Pharmaceuticals Inc | （２ｓ，３ｒ，４ｒ，５ｓ，６ｒ）－２－（４－氯－３－（４－乙氧苄基）苯基）－６－（甲硫）四氫－２ｈ－哌喃－３，４，５－三醇的固體形態與其使用方法 |
| DK2925735T3 (da) * | 2012-11-20 | 2019-06-17 | Lexicon Pharmaceuticals Inc | Inhibitorer for natriumglucose-cotransporter 1 |
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