RU2505521C2 - Производные бензилфенилциклогексана и способы их применения - Google Patents
Производные бензилфенилциклогексана и способы их применения Download PDFInfo
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- RU2505521C2 RU2505521C2 RU2010128940/04A RU2010128940A RU2505521C2 RU 2505521 C2 RU2505521 C2 RU 2505521C2 RU 2010128940/04 A RU2010128940/04 A RU 2010128940/04A RU 2010128940 A RU2010128940 A RU 2010128940A RU 2505521 C2 RU2505521 C2 RU 2505521C2
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- Prior art keywords
- group
- alkyl
- chloro
- compound
- phenyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 51
- MPFUMJUOVJWWAI-UHFFFAOYSA-N (1-benzylcyclohexyl)benzene Chemical class C1CCCCC1(C=1C=CC=CC=1)CC1=CC=CC=C1 MPFUMJUOVJWWAI-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 239000003814 drug Substances 0.000 claims abstract description 50
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
- 201000010099 disease Diseases 0.000 claims abstract description 24
- 229940124597 therapeutic agent Drugs 0.000 claims abstract description 21
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 16
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 10
- 206010007558 Cardiac failure chronic Diseases 0.000 claims abstract description 10
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 10
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- 208000002249 Diabetes Complications Diseases 0.000 claims abstract description 9
- 206010012655 Diabetic complications Diseases 0.000 claims abstract description 9
- 206010030113 Oedema Diseases 0.000 claims abstract description 7
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims abstract description 6
- 206010020772 Hypertension Diseases 0.000 claims abstract description 6
- 201000001431 Hyperuricemia Diseases 0.000 claims abstract description 6
- 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 6
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 6
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims abstract description 6
- 201000008980 hyperinsulinism Diseases 0.000 claims abstract description 6
- 208000008589 Obesity Diseases 0.000 claims abstract description 5
- 235000020824 obesity Nutrition 0.000 claims abstract description 5
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims abstract 7
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims abstract 7
- -1 (4R, 5S, 6R, 7R, 8R) -4- (4-chloro-3- (4-ethylbenzyl) phenyl) -8- (hydroxymethyl) spiro [2.5] octane-5,6,7-triol Chemical compound 0.000 claims description 155
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 239000000651 prodrug Substances 0.000 claims description 29
- 229940002612 prodrug Drugs 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 201000001421 hyperglycemia Diseases 0.000 claims description 8
- XYZUMOZQVNKWQE-AIURUUSXSA-N (1r,2r,3s,4r,5r,6s)-4-[4-chloro-3-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetrol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@@H]2[C@H]([C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O)=CC=C1Cl XYZUMOZQVNKWQE-AIURUUSXSA-N 0.000 claims description 7
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 239000002220 antihypertensive agent Substances 0.000 claims description 6
- 229940030600 antihypertensive agent Drugs 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 230000002961 anti-hyperuricemic effect Effects 0.000 claims description 4
- 239000000883 anti-obesity agent Substances 0.000 claims description 4
- OJNWITIERBFDHJ-RBMZQIMRSA-N (1r,2r,3s,4r,5r,6s)-4-[4-chloro-3-[(4-cyclohexylphenyl)methyl]phenyl]-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetrol Chemical compound O[C@H]1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1C1=CC=C(Cl)C(CC=2C=CC(=CC=2)C2CCCCC2)=C1 OJNWITIERBFDHJ-RBMZQIMRSA-N 0.000 claims description 3
- BYTBVOQEBOCXBB-SCTSWAKVSA-N (1r,2r,3s,4r,5r,6s)-4-[4-chloro-3-[(4-cyclopropylphenyl)methyl]phenyl]-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetrol Chemical compound O[C@H]1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1C1=CC=C(Cl)C(CC=2C=CC(=CC=2)C2CC2)=C1 BYTBVOQEBOCXBB-SCTSWAKVSA-N 0.000 claims description 3
- ISQIDKPLOKBKHJ-AIURUUSXSA-N (1r,2r,3s,4r,5r,6s)-4-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetrol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@@H]2[C@H]([C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O)=CC=C1Cl ISQIDKPLOKBKHJ-AIURUUSXSA-N 0.000 claims description 3
- HOAFNCIYHHMECH-SCTSWAKVSA-N (1r,2r,3s,4r,5r,6s)-4-[4-chloro-3-[(4-propylphenyl)methyl]phenyl]-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetrol Chemical compound C1=CC(CCC)=CC=C1CC1=CC([C@@H]2[C@H]([C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O)=CC=C1Cl HOAFNCIYHHMECH-SCTSWAKVSA-N 0.000 claims description 3
- XTXXXHYCYNHHAW-SROFAIGKSA-N (1r,2s,3r,4r,5s,6r)-4-[2-[(4-ethylphenyl)methyl]phenoxy]-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetrol Chemical compound C1=CC(CC)=CC=C1CC1=CC=CC=C1O[C@@H]1[C@@H](O)[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O XTXXXHYCYNHHAW-SROFAIGKSA-N 0.000 claims description 3
- DYKFSNIGUCSCGO-AIURUUSXSA-N 1-[4-[[2-chloro-5-[(1r,2s,3r,4r,5s,6r)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl]phenyl]methyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1CC1=CC([C@@H]2[C@H]([C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O)=CC=C1Cl DYKFSNIGUCSCGO-AIURUUSXSA-N 0.000 claims description 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- UWNNGHCXCMEVKY-SVXFZJLFSA-N ClC1=C(C=C(C=C1)[C@H]1[C@@H]([C@H]([C@H]([C@H](C1=C)CO)O)O)O)CC1=CC=C(C=C1)CC Chemical compound ClC1=C(C=C(C=C1)[C@H]1[C@@H]([C@H]([C@H]([C@H](C1=C)CO)O)O)O)CC1=CC=C(C=C1)CC UWNNGHCXCMEVKY-SVXFZJLFSA-N 0.000 claims description 2
- 229940125710 antiobesity agent Drugs 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000011734 sodium Substances 0.000 abstract description 39
- 239000000543 intermediate Substances 0.000 abstract description 15
- 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 abstract description 13
- 229910052708 sodium Inorganic materials 0.000 abstract description 11
- 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 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 9
- 239000008103 glucose Substances 0.000 abstract description 8
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 102000034534 Cotransporters Human genes 0.000 abstract description 3
- 108020003264 Cotransporters Proteins 0.000 abstract description 3
- 230000001419 dependent effect Effects 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 108
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 93
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- 238000002360 preparation method Methods 0.000 description 61
- 239000000243 solution Substances 0.000 description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
- 239000000463 material Substances 0.000 description 32
- 125000001424 substituent group Chemical group 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
- 239000000460 chlorine Substances 0.000 description 28
- 229940079593 drug Drugs 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- 239000007983 Tris buffer Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- 125000000392 cycloalkenyl group Chemical group 0.000 description 20
- 102100037202 Sodium/myo-inositol cotransporter 2 Human genes 0.000 description 19
- 101710090560 Sodium/myo-inositol cotransporter 2 Proteins 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 239000003112 inhibitor Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000012267 brine Substances 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000012300 argon atmosphere Substances 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- ZOECEJDDYZQJEZ-UHFFFAOYSA-N 4-bromo-1-chloro-2-[(4-ethylphenyl)methyl]benzene Chemical compound C1=CC(CC)=CC=C1CC1=CC(Br)=CC=C1Cl ZOECEJDDYZQJEZ-UHFFFAOYSA-N 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 238000002953 preparative HPLC Methods 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 108091006269 SLC5A2 Proteins 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 description 9
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000012746 preparative thin layer chromatography Methods 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 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 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 102000004877 Insulin Human genes 0.000 description 7
- 108090001061 Insulin Proteins 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000556 agonist Substances 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
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- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 7
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- DVZMGUFHTXWXQK-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)-(4-ethylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)C1=CC(Br)=CC=C1Cl DVZMGUFHTXWXQK-UHFFFAOYSA-N 0.000 description 5
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- 229940123208 Biguanide Drugs 0.000 description 5
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 5
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- 102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
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- 238000009835 boiling Methods 0.000 description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N boron trifluoride etherate Substances FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 5
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
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| AU2012260741B2 (en) * | 2011-05-26 | 2016-10-27 | Tfchem | Family of aryl, heteroaryl, O-aryl and O-heteroaryl carbasugars |
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| 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 |
| CN103570671B (zh) * | 2012-09-26 | 2016-03-30 | 上海天慈生物谷生物工程有限公司 | 一种降糖化合物及其制法和应用 |
| CN105611920B (zh) | 2013-10-12 | 2021-07-16 | 泰拉科斯萨普有限责任公司 | 羟基-二苯甲烷衍生物的制备 |
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| US10759729B2 (en) * | 2016-11-07 | 2020-09-01 | The Chinese University Of Hong Kong | Compounds for treating diabetes |
| CN116785268A (zh) * | 2022-03-14 | 2023-09-22 | 江苏万邦生化医药集团有限责任公司 | 一种sglt-2抑制剂的药物组合物 |
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| HRP20180127T1 (hr) | 2007-08-23 | 2018-03-09 | Theracos Sub, Llc | Derivati (2s,3r,4r,5s,6r)-2(4-kloro-3-benzilfenil)-6-(hidroksimetil)tetrahidro-2h-piran-3,4,5-triola za primjenu u liječenju dijabetesa |
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2008
- 2008-11-12 UA UAA201008620A patent/UA101004C2/uk unknown
- 2008-12-11 KR KR1020107015420A patent/KR101567969B1/ko not_active Expired - Fee Related
- 2008-12-11 EP EP08859426.2A patent/EP2230907B1/en active Active
- 2008-12-11 US US12/333,190 patent/US8129434B2/en not_active Expired - Fee Related
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- 2008-12-11 BR BRPI0819930A patent/BRPI0819930A2/pt not_active IP Right Cessation
- 2008-12-11 CN CN200880126441.9A patent/CN101938902B/zh not_active Expired - Fee Related
- 2008-12-11 NZ NZ586639A patent/NZ586639A/en not_active IP Right Cessation
- 2008-12-11 WO PCT/US2008/086472 patent/WO2009076550A1/en not_active Ceased
- 2008-12-11 AU AU2008335080A patent/AU2008335080B2/en not_active Ceased
- 2008-12-11 RU RU2010128940/04A patent/RU2505521C2/ru not_active IP Right Cessation
- 2008-12-11 TW TW097148259A patent/TWI426081B/zh not_active IP Right Cessation
- 2008-12-12 AR ARP080105417A patent/AR071268A1/es not_active Application Discontinuation
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2010
- 2010-06-07 IL IL206234A patent/IL206234A0/en unknown
- 2010-06-22 ZA ZA2010/04400A patent/ZA201004400B/en unknown
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| SU991944A3 (ru) * | 1977-09-13 | 1983-01-23 | Пфайзер,Инк (Фирма) | Способ получени 3-/2-окси-4-(замещенных)-фенил/циклоалканольных соединений |
| US20060009400A1 (en) * | 2004-07-06 | 2006-01-12 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture |
| CA2573777A1 (en) * | 2004-07-26 | 2006-02-02 | Chugai Seiyaku Kabushiki Kaisha | Novel cyclohexane derivative, prodrug thereof and salt thereof, and therapeutic agent containing the same for diabetes |
| US20060035841A1 (en) * | 2004-08-11 | 2006-02-16 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-phenyl-substituted cycles, medicaments containing such compounds, their use and process for their manufacture |
| US20070072896A1 (en) * | 2005-08-05 | 2007-03-29 | Eisai Co., Ltd. | Inhibitors of c-Jun N-terminal kinases for the treatment of neurodegenerative disorders relating to apoptosis and/or inflammation |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2230907A1 (en) | 2010-09-29 |
| AR113211A2 (es) | 2020-02-19 |
| UA101004C2 (en) | 2013-02-25 |
| AU2008335080A1 (en) | 2009-06-18 |
| BRPI0819930A2 (pt) | 2016-05-17 |
| CN101938902B (zh) | 2014-07-02 |
| CN101938902A (zh) | 2011-01-05 |
| EP2230907A4 (en) | 2015-04-08 |
| CA2707909C (en) | 2016-10-18 |
| AR071268A1 (es) | 2010-06-09 |
| US8129434B2 (en) | 2012-03-06 |
| RU2010128940A (ru) | 2012-01-20 |
| IL206234A0 (en) | 2010-12-30 |
| JP2011506469A (ja) | 2011-03-03 |
| EP2230907B1 (en) | 2018-05-09 |
| US20090156516A1 (en) | 2009-06-18 |
| AU2008335080B2 (en) | 2014-06-05 |
| JP5507464B2 (ja) | 2014-05-28 |
| KR101567969B1 (ko) | 2015-11-10 |
| WO2009076550A1 (en) | 2009-06-18 |
| TW200932755A (en) | 2009-08-01 |
| CA2707909A1 (en) | 2009-06-18 |
| TWI426081B (zh) | 2014-02-11 |
| NZ586639A (en) | 2011-06-30 |
| KR20100098690A (ko) | 2010-09-08 |
| ZA201004400B (en) | 2014-10-29 |
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| MM4A | The patent is invalid due to non-payment of fees |
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