JP2010536882A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010536882A5 JP2010536882A5 JP2010522073A JP2010522073A JP2010536882A5 JP 2010536882 A5 JP2010536882 A5 JP 2010536882A5 JP 2010522073 A JP2010522073 A JP 2010522073A JP 2010522073 A JP2010522073 A JP 2010522073A JP 2010536882 A5 JP2010536882 A5 JP 2010536882A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- cycloalkyl
- alkenyl
- optionally
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 33
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 21
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 20
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 17
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 6
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 4
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- 125000006709 (C5-C7) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 18
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims 2
- MQROWBZJYWQTKC-XILPJHNUSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(1-prop-2-ynoxypropan-2-yloxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OC(COCC#C)C)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl MQROWBZJYWQTKC-XILPJHNUSA-N 0.000 claims 1
- GEKMJNUTSMVHIA-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclobutyloxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOC3CCC3)=CC=2)=C1 GEKMJNUTSMVHIA-RXFVIIJJSA-N 0.000 claims 1
- KQWVDYYPFPMBGI-ZRXLTWLYSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclohex-2-en-1-yloxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOC3C=CCCC3)=CC=2)=C1 KQWVDYYPFPMBGI-ZRXLTWLYSA-N 0.000 claims 1
- WQHQGECQHKTVOS-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclopentyloxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOC3CCCC3)=CC=2)=C1 WQHQGECQHKTVOS-RTJMFUJLSA-N 0.000 claims 1
- BTCRKOKVYTVOLU-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclopropyloxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOC3CC3)=CC=2)=C1 BTCRKOKVYTVOLU-SJSRKZJXSA-N 0.000 claims 1
- LQLLRLTVYLVSTP-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclopropyloxyethyl)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(CCOC3CC3)=CC=2)=C1 LQLLRLTVYLVSTP-SJSRKZJXSA-N 0.000 claims 1
- MMFIJGNWQQHBQZ-GEMFNBEASA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclopropyloxypropoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1CC1OC(C)COC(C=C1)=CC=C1CC(C(=CC=1)Cl)=CC=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O MMFIJGNWQQHBQZ-GEMFNBEASA-N 0.000 claims 1
- MSMWKUYWZFAMKM-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-prop-2-ynoxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCC#C)=CC=2)=C1 MSMWKUYWZFAMKM-SJSRKZJXSA-N 0.000 claims 1
- RQAIBPUKCDEEFR-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(3-cyclopropyloxypropyl)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(CCCOC3CC3)=CC=2)=C1 RQAIBPUKCDEEFR-RXFVIIJJSA-N 0.000 claims 1
- ZBTRKQLHARGRNC-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(3-cyclopropylprop-2-ynoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCC#CC3CC3)=CC=2)=C1 ZBTRKQLHARGRNC-RXFVIIJJSA-N 0.000 claims 1
- CDGGMQKRHMAOOH-ZQGJOIPISA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(4-hydroxybut-2-ynoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCC#CCO)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl CDGGMQKRHMAOOH-ZQGJOIPISA-N 0.000 claims 1
- RVVVWCKTJNHSHH-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(4-methoxybut-2-ynoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCC#CCOC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl RVVVWCKTJNHSHH-SJSRKZJXSA-N 0.000 claims 1
- UBKUUUVWYGYTIJ-IZDGYUISSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[(e)-3-cyclopropylprop-2-enoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OC\C=C\C3CC3)=CC=2)=C1 UBKUUUVWYGYTIJ-IZDGYUISSA-N 0.000 claims 1
- RSKISEGUPKNIQB-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(1-methylcyclopropyl)oxyethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(CC=2C(=CC=C(C=2)[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)Cl)C=CC=1OCCOC1(C)CC1 RSKISEGUPKNIQB-SJSRKZJXSA-N 0.000 claims 1
- KAGIONOGUAKIHP-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2,2,2-trifluoroethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCC(F)(F)F)=CC=2)=C1 KAGIONOGUAKIHP-BDHVOXNPSA-N 0.000 claims 1
- UKCQFFWJYRBCDQ-IFPLKCGESA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2,2-difluoroethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCC(F)F)=CC=2)=C1 UKCQFFWJYRBCDQ-IFPLKCGESA-N 0.000 claims 1
- VSIOFYMNPQFYQS-ZQGJOIPISA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2-fluoroethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCCF)=CC=2)=C1 VSIOFYMNPQFYQS-ZQGJOIPISA-N 0.000 claims 1
- GNFILVCRLHZYQW-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2-methoxyethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCCOCCOC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl GNFILVCRLHZYQW-SJSRKZJXSA-N 0.000 claims 1
- DGCHJACJEUHZMB-SEFGFODJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2-pyrrolidin-1-ylethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCCN3CCCC3)=CC=2)=C1 DGCHJACJEUHZMB-SEFGFODJSA-N 0.000 claims 1
- GCYCBOWTHWGKFK-ADAARDCZSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(difluoromethoxy)ethyl]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(CCOC(F)F)=CC=2)=C1 GCYCBOWTHWGKFK-ADAARDCZSA-N 0.000 claims 1
- BTQUQFQLIUNWQM-YRLFNMAZSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-[(3r)-oxolan-3-yl]oxyethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCO[C@H]3COCC3)=CC=2)=C1 BTQUQFQLIUNWQM-YRLFNMAZSA-N 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 201000001431 Hyperuricemia Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010030113 Oedema Diseases 0.000 claims 1
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims 1
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 239000000883 anti-obesity agent Substances 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- 229940125710 antiobesity agent Drugs 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 229940116269 uric acid Drugs 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 229940002612 prodrug Drugs 0.000 description 11
- 239000000651 prodrug Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BHBZWCSWSRMTIV-GOSISDBHSA-N (3r)-3-[2-[4-[(5-bromo-2-chlorophenyl)methyl]phenoxy]ethoxy]oxolane Chemical compound ClC1=CC=C(Br)C=C1CC(C=C1)=CC=C1OCCO[C@H]1COCC1 BHBZWCSWSRMTIV-GOSISDBHSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- QXAMTEJJAZOINB-UHFFFAOYSA-N oxane-3,4,5-triol Chemical compound OC1COCC(O)C1O QXAMTEJJAZOINB-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- VNGTZLYNGGLPIZ-WCXIOVBPSA-N (3r,4s,5r,6r)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-one Chemical compound C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C VNGTZLYNGGLPIZ-WCXIOVBPSA-N 0.000 description 1
- ZBDGHWFPLXXWRD-UHFFFAOYSA-N 2-methoxyoxane-3,4,5-triol Chemical compound COC1OCC(O)C(O)C1O ZBDGHWFPLXXWRD-UHFFFAOYSA-N 0.000 description 1
- YDTVBOBTLKKRJM-JXBUXCBHSA-N COC([C@@H]([C@H]1O)O)(c(cc2)cc(Cc(cc3)ccc3OCCO[C@H]3COCC3)c2Cl)O[C@H](CO)[C@H]1O Chemical compound COC([C@@H]([C@H]1O)O)(c(cc2)cc(Cc(cc3)ccc3OCCO[C@H]3COCC3)c2Cl)O[C@H](CO)[C@H]1O YDTVBOBTLKKRJM-JXBUXCBHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BHBZWCSWSRMTIV-SFHVURJKSA-N Clc(c(Cc(cc1)ccc1OCCO[C@@H]1COCC1)c1)ccc1Br Chemical compound Clc(c(Cc(cc1)ccc1OCCO[C@@H]1COCC1)c1)ccc1Br BHBZWCSWSRMTIV-SFHVURJKSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 125000005855 N,N-di(C1-C2)alkylcarbamoyl-(C1-C2)alkyl group Chemical group 0.000 description 1
- BTQUQFQLIUNWQM-MKTRHSHTSA-N OC[C@@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@H]1c(cc1Cc(cc2)ccc2OCCO[C@H]2COCC2)ccc1Cl Chemical compound OC[C@@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@H]1c(cc1Cc(cc2)ccc2OCCO[C@H]2COCC2)ccc1Cl BTQUQFQLIUNWQM-MKTRHSHTSA-N 0.000 description 1
- XDPCNPCKDGQBAN-SCSAIBSYSA-N O[C@H]1COCC1 Chemical compound O[C@H]1COCC1 XDPCNPCKDGQBAN-SCSAIBSYSA-N 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 108010038807 Oligopeptides Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000005854 carbamoyl-(C1-C2)alkyl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000005852 di-N,N—(C1-C2)alkylamino(C2-C3)alkyl group Chemical group 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000005858 morpholino(C2-C3)alkyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005856 piperidino(C2-C3)alkyl group Chemical group 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005857 pyrrolidino(C2-C3)alkyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000005853 β-dimethylaminoethyl group Chemical group 0.000 description 1
Images
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95762507P | 2007-08-23 | 2007-08-23 | |
| US60/957,625 | 2007-08-23 | ||
| PCT/US2008/074058 WO2009026537A1 (en) | 2007-08-23 | 2008-08-22 | Benzylbenzene derivatives and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010536882A JP2010536882A (ja) | 2010-12-02 |
| JP2010536882A5 true JP2010536882A5 (OSRAM) | 2011-02-24 |
| JP4809931B2 JP4809931B2 (ja) | 2011-11-09 |
Family
ID=40378694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010522073A Active JP4809931B2 (ja) | 2007-08-23 | 2008-08-22 | ベンジルベンゼン誘導体およびその使用方法 |
Country Status (30)
| Country | Link |
|---|---|
| US (4) | US7838499B2 (OSRAM) |
| EP (2) | EP2187742B1 (OSRAM) |
| JP (1) | JP4809931B2 (OSRAM) |
| KR (1) | KR101107425B1 (OSRAM) |
| CN (1) | CN101790311B (OSRAM) |
| AR (2) | AR068016A1 (OSRAM) |
| AU (1) | AU2008288770B2 (OSRAM) |
| BR (1) | BRPI0815708B8 (OSRAM) |
| CA (1) | CA2697349C (OSRAM) |
| CY (1) | CY1119810T1 (OSRAM) |
| DK (1) | DK2187742T3 (OSRAM) |
| ES (1) | ES2654894T3 (OSRAM) |
| HK (1) | HK1254895A1 (OSRAM) |
| HR (1) | HRP20180127T1 (OSRAM) |
| HU (1) | HUE035947T2 (OSRAM) |
| IL (1) | IL203915A (OSRAM) |
| LT (1) | LT2187742T (OSRAM) |
| MX (1) | MX2010002027A (OSRAM) |
| NO (1) | NO2187742T3 (OSRAM) |
| NZ (1) | NZ583369A (OSRAM) |
| PL (1) | PL2187742T3 (OSRAM) |
| PT (1) | PT2187742T (OSRAM) |
| RS (1) | RS56822B1 (OSRAM) |
| RU (1) | RU2497526C2 (OSRAM) |
| SG (1) | SG188800A1 (OSRAM) |
| SI (1) | SI2187742T1 (OSRAM) |
| TW (1) | TWI434691B (OSRAM) |
| UA (1) | UA99924C2 (OSRAM) |
| WO (1) | WO2009026537A1 (OSRAM) |
| ZA (1) | ZA201001051B (OSRAM) |
Families Citing this family (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4809931B2 (ja) * | 2007-08-23 | 2011-11-09 | セラコス・インコーポレイテッド | ベンジルベンゼン誘導体およびその使用方法 |
| CA2699285C (en) | 2007-09-10 | 2016-12-13 | Ahmed F. Abdel-Magid | Process for the preparation of compounds useful as inhibitors of sodium-dependent glucose transporter (sglt) |
| UA101004C2 (en) | 2007-12-13 | 2013-02-25 | Теракос, Инк. | Derivatives of benzylphenylcyclohexane and use thereof |
| MX2011000637A (es) | 2008-07-15 | 2011-05-02 | Theracos Inc | Derivados deuretados de bencilbenceno y metodos de uso. |
| AU2014201286B2 (en) * | 2008-08-22 | 2015-07-02 | Theracosbio, Llc | Processes for the preparation of SGLT2 inhibitors |
| EP2324002B1 (en) * | 2008-08-22 | 2016-10-05 | Theracos Sub, LLC | Processes for the preparation of sglt2 inhibitors |
| MX2011002166A (es) | 2008-08-28 | 2011-04-07 | Pfizer | Derivados de dioxa-biciclo[3.2.1]octano-2,3,1-triol. |
| US9056850B2 (en) | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
| WO2010062861A2 (en) | 2008-11-26 | 2010-06-03 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of obesity and diabetes |
| US20110009347A1 (en) | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
| AU2010270202B2 (en) | 2009-07-10 | 2014-04-24 | Janssen Pharmaceutica Nv | Crystallisation process for 1-(beta-D-glucopyranosyl)-4-methyl-3- [5-(4-fluorophenyl)-2-thienylmethyl] benzene |
| US8163704B2 (en) | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| EA021983B1 (ru) | 2009-11-02 | 2015-10-30 | Пфайзер Инк. | Производные диоксабицикло[3.2.1]октан-2,3,4-триола |
| AR079438A1 (es) | 2009-12-09 | 2012-01-25 | Panacea Biotec Ltd | Derivados de azucar, composiciones farmaceuticas y sus usos |
| CN102134226B (zh) * | 2010-01-26 | 2013-06-12 | 天津药物研究院 | 一类苯基c-葡萄糖苷衍生物、其制备方法和用途 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| CN102234287B (zh) | 2010-04-26 | 2015-08-05 | 上海阳帆医药科技有限公司 | 硝基咪唑类化合物、其制备方法和用途 |
| ES2552657T3 (es) | 2010-05-26 | 2015-12-01 | Satiogen Pharmaceuticals, Inc. | Inhibidores del reciclado de ácidos biliares y saciógenos para el tratamiento de diabetes, obesidad, y afecciones gastrointestinales inflamatorias |
| WO2011153712A1 (en) | 2010-06-12 | 2011-12-15 | Theracos, Inc. | Crystalline form of benzylbenzene sglt2 inhibitor |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| CN102372722A (zh) | 2010-08-10 | 2012-03-14 | 江苏恒瑞医药股份有限公司 | C-芳基葡萄糖苷衍生物、其制备方法及其在医药上的应用 |
| WO2012025857A1 (en) | 2010-08-23 | 2012-03-01 | Hetero Research Foundation | Cycloalkyl methoxybenzyl phenyl pyran derivatives as sodium dependent glucose co transporter (sglt2) inhibitors |
| GB201101959D0 (en) | 2011-02-04 | 2011-03-23 | Univ Nottingham | Novel ether linked compoundsand improved treatments for cardiac and cardiovascular disease |
| JP6105489B2 (ja) * | 2011-02-18 | 2017-03-29 | シャンハイ インリ ファーマシューティカル カンパニー リミティド | アリールグルコシド化合物、その調製方法及び使用 |
| CN102675378A (zh) * | 2011-03-09 | 2012-09-19 | 天津药物研究院 | 一类含环丙烷结构的c-葡萄糖苷衍生物、其制备方法和用途 |
| AU2012241897C1 (en) | 2011-04-13 | 2017-05-11 | Janssen Pharmaceutica Nv | Process for the preparation of compounds useful as inhibitors of SGLT2 |
| CN102757415B (zh) * | 2011-04-25 | 2015-07-29 | 北京普禄德医药科技有限公司 | 一种钠依赖性葡萄糖转运蛋白抑制剂及其制备方法和用途 |
| US9035044B2 (en) * | 2011-05-09 | 2015-05-19 | Janssen Pharmaceutica Nv | L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol |
| US9562029B2 (en) | 2011-06-25 | 2017-02-07 | Xuanzhu Pharma Co., Ltd. | C-glycoside derivatives |
| 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 |
| US9018249B2 (en) * | 2011-09-13 | 2015-04-28 | Panacea Biotec Limited | SGLT inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| SG11201401849QA (en) | 2011-10-28 | 2014-05-29 | Lumena Pharmaceuticals Inc | Bile acid recycling inhibitors for treatment of pediatric cholestatic liver diseases |
| SG10201406155QA (en) | 2011-10-28 | 2014-11-27 | Lumena Pharmaceuticals Inc | Bile Acid Recycling Inhibitors For Treatment Of Pediatric Cholestatic Liver Diseases |
| US8697658B2 (en) * | 2011-12-15 | 2014-04-15 | National Health Research Institutes | Glycoside compounds |
| WO2013152476A1 (en) * | 2012-04-10 | 2013-10-17 | Theracos, Inc. | Process for the preparation of benzylbenzene sglt2 inhibitors |
| US9193751B2 (en) | 2012-04-10 | 2015-11-24 | Theracos, Inc. | Process for the preparation of benzylbenzene SGLT2 inhibitors |
| RU2015123738A (ru) | 2012-11-20 | 2017-01-10 | Лексикон Фармасьютикалз, Инк. | Ингибиторы котранспортера натрий-глюкозы 1 |
| CN103910769B (zh) | 2012-12-31 | 2018-10-02 | 上海璎黎药业有限公司 | 葡萄糖衍生物和脯氨酸的复合物、晶体、制备方法及应用 |
| US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
| US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
| US9394329B2 (en) | 2013-09-27 | 2016-07-19 | Sunshine Lake Pharma Co., Ltd. | Glucopyranosyl derivatives and their uses in medicine |
| WO2015051484A1 (en) | 2013-10-12 | 2015-04-16 | Theracos, Inc. | Preparation of hydroxy-benzylbenzene derivatives |
| US9315438B2 (en) | 2014-01-03 | 2016-04-19 | Xuanzhu Pharma Co., Ltd | Optically pure benzyl-4-chlorophenyl-C-glucoside derivative |
| CN104031098A (zh) * | 2014-06-21 | 2014-09-10 | 李友香 | 降糖药物 |
| CN104017031A (zh) * | 2014-06-21 | 2014-09-03 | 李友香 | 降血糖药物和组合物 |
| CN104086379B (zh) * | 2014-07-29 | 2015-08-12 | 安徽联创生物医药股份有限公司 | 达格列净中间体的合成方法 |
| JP2016060698A (ja) * | 2014-09-16 | 2016-04-25 | 本田技研工業株式会社 | １，２−ビス（２，２−ジフルオロエトキシ）エタンおよびその製造方法 |
| US9305155B1 (en) * | 2015-02-12 | 2016-04-05 | United Services Automobile Association (Usaa) | Toggling biometric authentication |
| CN105061373B (zh) * | 2015-09-06 | 2017-10-20 | 合肥华方医药科技有限公司 | 一种达格列净异构体杂质的合成方法 |
| US20170071970A1 (en) | 2015-09-15 | 2017-03-16 | Janssen Pharmaceutica Nv | Co-therapy comprising canagliflozin and phentermine for the treatment of obesity and obesity related disorders |
| US10752604B2 (en) * | 2016-01-04 | 2020-08-25 | Je II Pharmaceutical Co., Ltd. | C-glucoside derivative containing fused phenyl ring or pharmaceutically acceptable salt thereof, process for preparing same, and pharmaceutical composition comprising same |
| CN105770861B (zh) * | 2016-04-08 | 2020-02-28 | 吴一行 | 一种用于治疗男性糖尿病患者勃起功能障碍的药物 |
| US11312740B2 (en) * | 2017-05-09 | 2022-04-26 | Piramal Pharma Limited | Process for the preparation of SGLT2 inhibitors and intermediates thereof |
| WO2020039394A1 (en) | 2018-08-24 | 2020-02-27 | Novartis Ag | New drug combinations |
| WO2020084559A1 (en) | 2018-10-26 | 2020-04-30 | Janssen Pharmaceutica Nv | Glucopyranose derivatives useful as sglt2 inhibitors |
| WO2020084560A1 (en) | 2018-10-26 | 2020-04-30 | Janssen Pharmaceutica Nv | Glucopyranose derivatives useful as sglt2 inhibitors |
| BR112021018169A2 (pt) | 2019-03-14 | 2021-11-16 | Increvet Inc | Composto para o controle de diabetes de felinos |
| JP2022554344A (ja) * | 2019-11-07 | 2022-12-28 | インクレベット，インコーポレイティド | コンパニオンアニマルにおける慢性腎疾患、高血圧、及び心不全の管理のためのナトリウム－グルコース共輸送体阻害剤 |
| CN114599643B (zh) * | 2020-05-15 | 2023-04-14 | 上海喆邺生物科技有限公司 | 一种芳基葡糖苷衍生物 |
| CN111662166A (zh) * | 2020-05-28 | 2020-09-15 | 吴赣药业（苏州）有限公司 | 一种5-溴-2-氯-4′-乙氧基二苯甲烷的制备方法 |
| TW202412756A (zh) | 2022-05-25 | 2024-04-01 | 德商百靈佳殷格翰維美迪加股份有限公司 | 包含sglt-2抑制劑之水性醫藥組合物 |
| CN120857933A (zh) | 2023-03-06 | 2025-10-28 | 勃林格殷格翰动物保健有限公司 | 用于递送特别包含一或多种sglt-2抑制剂的液体药物组合物的系统 |
| AU2024277852A1 (en) | 2023-05-24 | 2025-10-16 | 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 |
| TW202508593A (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抑制劑及匹莫苯坦(pimobendan)及/或替米沙坦(telmisartan)之非人類哺乳動物心臟病之組合治療及/或預防 |
| WO2025056984A1 (en) * | 2023-09-12 | 2025-03-20 | Vijayasri Organics Private Limited | A novel process for the preparation of bexagliflozin a sglt2 inhibitor and its intermediates thereof |
| CN117343115A (zh) * | 2023-10-18 | 2024-01-05 | 宁波工程学院 | 基于扭转结构特征的酰胺为原料合成糖缀合物的方法 |
| US12303604B1 (en) | 2024-10-16 | 2025-05-20 | Currax Pharmaceuticals Llc | Pharmaceutical formulations comprising naltrexone and/or bupropion |
Family Cites Families (118)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4499289A (en) | 1982-12-03 | 1985-02-12 | G. D. Searle & Co. | Octahydronapthalenes |
| US4933438A (en) | 1984-02-29 | 1990-06-12 | University Of Florida | Brain-specific analogues of centrally acting amines |
| US4613610A (en) | 1984-06-22 | 1986-09-23 | Sandoz Pharmaceuticals Corp. | Cholesterol biosynthesis inhibiting pyrazole analogs of mevalonolactone and its derivatives |
| US4686237A (en) | 1984-07-24 | 1987-08-11 | Sandoz Pharmaceuticals Corp. | Erythro-(E)-7-[3'-C1-3 alkyl-1'-(3",5"-dimethylphenyl)naphth-2'-yl]-3,5-dihydroxyhept-6-enoic acids and derivatives thereof |
| US4647576A (en) | 1984-09-24 | 1987-03-03 | Warner-Lambert Company | Trans-6-[2-(substitutedpyrrol-1-yl)alkyl]-pyran-2-one inhibitors of cholesterol synthesis |
| US6150354A (en) | 1987-01-15 | 2000-11-21 | Bonnie Davis | Compounds for the treatment of Alzheimer's disease |
| US4924024A (en) | 1988-01-11 | 1990-05-08 | E. R. Squibb & Sons, Inc. | Phosphorus-containing squalene synthetase inhibitors, new intermediates and method |
| US4871721A (en) | 1988-01-11 | 1989-10-03 | E. R. Squibb & Sons, Inc. | Phosphorus-containing squalene synthetase inhibitors |
| US5506219A (en) | 1988-08-29 | 1996-04-09 | E. R. Squibb & Sons, Inc. | Pyridine anchors for HMG-CoA reductase inhibitors |
| US5753675A (en) | 1989-03-03 | 1998-05-19 | Novartis Pharmaceuticals Corporation | Quinoline analogs of mevalonolactone and derivatives thereof |
| US5133974A (en) | 1989-05-05 | 1992-07-28 | Kv Pharmaceutical Company | Extended release pharmaceutical formulations |
| DK0584185T3 (da) | 1991-05-14 | 2000-02-07 | Ernir Snorrason | Behandling af træthedssyndrom med cholinesteraseinhibitorer |
| IT1250421B (it) | 1991-05-30 | 1995-04-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato con proprieta' bio-adesive. |
| US5595872A (en) | 1992-03-06 | 1997-01-21 | Bristol-Myers Squibb Company | Nucleic acids encoding microsomal trigyceride transfer protein |
| US5712396A (en) | 1992-10-28 | 1998-01-27 | Magnin; David R. | α-phosphonosulfonate squalene synthetase inhibitors |
| US6537579B1 (en) | 1993-02-22 | 2003-03-25 | American Bioscience, Inc. | Compositions and methods for administration of pharmacologically active compounds |
| US5739135A (en) | 1993-09-03 | 1998-04-14 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| FR2710265B1 (fr) | 1993-09-22 | 1995-10-20 | Adir | Composition pharmaceutique bioadhésive pour la libération contrôlée de principes actifs. |
| US5620997A (en) | 1995-05-31 | 1997-04-15 | Warner-Lambert Company | Isothiazolones |
| US6548084B2 (en) | 1995-07-20 | 2003-04-15 | Smithkline Beecham Plc | Controlled release compositions |
| US6245347B1 (en) | 1995-07-28 | 2001-06-12 | Zars, Inc. | Methods and apparatus for improved administration of pharmaceutically active compounds |
| AU6966696A (en) | 1995-10-05 | 1997-04-28 | Warner-Lambert Company | Method for treating and preventing inflammation and atherosclerosis |
| DE19541260A1 (de) | 1995-11-06 | 1997-05-07 | Lohmann Therapie Syst Lts | Therapeutische Zubereitung zur transdermalen Applikation von Wirkstoffen durch die Haut |
| US5962440A (en) | 1996-05-09 | 1999-10-05 | Bristol-Myers Squibb Company | Cyclic phosphonate ester inhibitors of microsomal triglyceride transfer protein and method |
| US5885983A (en) | 1996-05-10 | 1999-03-23 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| US5827875A (en) | 1996-05-10 | 1998-10-27 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| US6512010B1 (en) | 1996-07-15 | 2003-01-28 | Alza Corporation | Formulations for the administration of fluoxetine |
| US6011155A (en) | 1996-11-07 | 2000-01-04 | Novartis Ag | N-(substituted glycyl)-2-cyanopyrrolidines, pharmaceutical compositions containing them and their use in inhibiting dipeptidyl peptidase-IV |
| US5760246A (en) | 1996-12-17 | 1998-06-02 | Biller; Scott A. | Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method |
| CN1277550A (zh) | 1997-09-11 | 2000-12-20 | 尼科梅德丹麦有限公司 | 非甾体抗炎药物(NSAIDs)的改进释放的复合型组合物 |
| US6624200B2 (en) | 1998-08-25 | 2003-09-23 | Columbia Laboratories, Inc. | Bioadhesive progressive hydration tablets |
| US6607751B1 (en) | 1997-10-10 | 2003-08-19 | Intellipharamaceutics Corp. | Controlled release delivery device for pharmaceutical agents incorporating microbial polysaccharide gum |
| US6403597B1 (en) | 1997-10-28 | 2002-06-11 | Vivus, Inc. | Administration of phosphodiesterase inhibitors for the treatment of premature ejaculation |
| US6248864B1 (en) | 1997-12-31 | 2001-06-19 | Adherex Technologies, Inc. | Compounds and methods and modulating tissue permeability |
| US6613358B2 (en) | 1998-03-18 | 2003-09-02 | Theodore W. Randolph | Sustained-release composition including amorphous polymer |
| US6312717B1 (en) | 1998-07-07 | 2001-11-06 | Bristol-Myers Squibb Company | Method for treatment of anxiety and depression |
| US6197798B1 (en) | 1998-07-21 | 2001-03-06 | Novartis Ag | Amino-benzocycloalkane derivatives |
| US20020009478A1 (en) | 1998-08-24 | 2002-01-24 | Douglas Joseph Dobrozsi | Oral liquid mucoadhesive compositions |
| SE9802864D0 (sv) | 1998-08-27 | 1998-08-27 | Pharmacia & Upjohn Ab | Transdermally administered tolterodine as antimuscarinic agent for the treatment of overactive bladder |
| KR100603900B1 (ko) | 1998-10-01 | 2006-07-25 | 노파르티스 아게 | 신규의 서방성 경구 제제 |
| US6248363B1 (en) | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| US6548529B1 (en) | 1999-04-05 | 2003-04-15 | Bristol-Myers Squibb Company | Heterocyclic containing biphenyl aP2 inhibitors and method |
| FR2792527B1 (fr) | 1999-04-22 | 2004-08-13 | Ethypharm Lab Prod Ethiques | Microgranules de ketoprofene, procede de preparation et compositions pharmaceutiques |
| US6172081B1 (en) | 1999-06-24 | 2001-01-09 | Novartis Ag | Tetrahydroisoquinoline 3-carboxamide derivatives |
| US6541020B1 (en) | 1999-07-09 | 2003-04-01 | Trimeris, Inc. | Methods and compositions for administration of therapeutic reagents |
| DE19933926A1 (de) | 1999-07-20 | 2001-01-25 | Boehringer Ingelheim Pharma | Biphenylderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
| US6562375B1 (en) | 1999-08-04 | 2003-05-13 | Yamanouchi Pharmaceuticals, Co., Ltd. | Stable pharmaceutical composition for oral use |
| JP2003508422A (ja) | 1999-09-02 | 2003-03-04 | ノストラム・ファーマスーティカルズ・インコーポレイテッド | 放出制御ペレット製剤 |
| US6544548B1 (en) | 1999-09-13 | 2003-04-08 | Keraplast Technologies, Ltd. | Keratin-based powders and hydrogel for pharmaceutical applications |
| PH12000002657B1 (en) | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| CN1896088A (zh) * | 1999-10-12 | 2007-01-17 | 布里斯托尔-迈尔斯斯奎布公司 | C－芳基葡糖苷sglt2抑制剂 |
| US6515117B2 (en) | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| US6080736A (en) | 1999-10-27 | 2000-06-27 | Janus Pharmaceuticals, Inc. | Methods and compositions for treating and preventing anxiety and anxiety disorders using optically pure (R) tofisopam |
| US6461631B1 (en) | 1999-11-16 | 2002-10-08 | Atrix Laboratories, Inc. | Biodegradable polymer composition |
| DE19963234A1 (de) | 1999-12-27 | 2002-01-24 | Boehringer Ingelheim Pharma | Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
| US6482439B2 (en) | 1999-12-29 | 2002-11-19 | Nanodelivery, Inc. | Drug delivery system exhibiting permeability control |
| EP1259484B1 (en) | 2000-01-18 | 2005-05-18 | Novartis AG | Carboxamides useful as inhibitors of microsomal triglyceride transfer protein and of apolipoprotein b secretion |
| JP2004501066A (ja) | 2000-01-28 | 2004-01-15 | ブリストル−マイヤーズ スクイブ カンパニー | 脂肪酸結合タンパク質のテトラヒドロピリミドンインヒビターおよび方法 |
| 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 |
| US6589549B2 (en) | 2000-04-27 | 2003-07-08 | Macromed, Incorporated | Bioactive agent delivering system comprised of microparticles within a biodegradable to improve release profiles |
| US6524621B2 (en) | 2000-05-01 | 2003-02-25 | Aeropharm Technology Inc. | Core formulation |
| US6432969B1 (en) | 2000-06-13 | 2002-08-13 | Novartis Ag | N-(substituted glycyl)-2 cyanopyrrolidines, pharmaceutical compositions containing them and their use in inhibiting dipeptidyl peptidase-IV |
| US6482440B2 (en) | 2000-09-21 | 2002-11-19 | Phase 2 Discovery, Inc. | Long acting antidepressant microparticles |
| AU2002237664A1 (en) | 2000-11-20 | 2002-05-27 | Bristol-Myers Squibb Company | Pyridone derivatives as AP2 inhibitors |
| US6524615B2 (en) | 2001-02-21 | 2003-02-25 | Kos Pharmaceuticals, Incorporated | Controlled release pharmaceutical composition |
| KR100388682B1 (ko) * | 2001-03-03 | 2003-06-25 | 삼성전자주식회사 | 반도체 메모리 장치의 스토리지 전극층 및 그 형성방법 |
| US6936590B2 (en) * | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| 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 |
| US6869947B2 (en) | 2001-07-03 | 2005-03-22 | Novo Nordisk A/S | Heterocyclic compounds that are inhibitors of the enzyme DPP-IV |
| US6919323B2 (en) | 2001-07-13 | 2005-07-19 | Bristol-Myers Squibb Company | Pyridazinone inhibitors of fatty acid binding protein and method |
| WO2003020737A1 (en) | 2001-09-05 | 2003-03-13 | Bristol-Myers Squibb Company | O-pyrazole glucoside sglt2 inhibitors and method of use |
| US6984645B2 (en) | 2001-11-16 | 2006-01-10 | Bristol-Myers Squibb Company | Dual inhibitors of adipocyte fatty acid binding protein and keratinocyte fatty acid binding protein |
| US6727261B2 (en) | 2001-12-27 | 2004-04-27 | Hoffman-La Roche Inc. | Pyrido[2,1-A]Isoquinoline derivatives |
| US6710040B1 (en) | 2002-06-04 | 2004-03-23 | Pfizer Inc. | Fluorinated cyclic amides as dipeptidyl peptidase IV inhibitors |
| DE60332743D1 (de) | 2002-08-08 | 2010-07-08 | Kissei Pharmaceutical | Pyrazolderivat, dieses enthaltende medizinische zusammensetzung, medizinische verwendung davon, und zwischenprodukt für dessen herstellung |
| US7414072B2 (en) * | 2002-08-09 | 2008-08-19 | Taisho Pharmaceutical Co., Ltd. | Aryl 5-thio-β-d-glucopyranoside derivatives and therapeutic agents for diabetes containing the same |
| CA2512389A1 (en) * | 2003-01-03 | 2004-07-29 | Bristol-Myers Squibb Company | Methods of producing c-aryl glucoside sglt2 inhibitors |
| ES2363941T3 (es) | 2003-03-14 | 2011-08-19 | Astellas Pharma Inc. | Derivados de c-glucósido para el tratamiento de diabetes. |
| JP2004300102A (ja) | 2003-03-31 | 2004-10-28 | Kissei Pharmaceut 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 |
| WO2005005238A1 (en) | 2003-07-02 | 2005-01-20 | Keith Gilstrap | Seatpost mounted bicycle wheel holding device |
| AU2004261663A1 (en) * | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted benzimidazole-, benztriazole-, and benzimidazolone-O-glucosides |
| CA2549015A1 (en) * | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted fused heterocyclic c-glycosides |
| ES2649737T5 (es) * | 2003-08-01 | 2021-07-07 | Mitsubishi Tanabe Pharma Corp | Compuestos novedosos que tienen actividad inhibidora frente a transportador de glucosa dependiente de sodio |
| EP1660509B1 (de) | 2003-08-26 | 2009-02-04 | Boehringer Ingelheim International GmbH | 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 |
| BRPI0414701A (pt) * | 2003-09-24 | 2006-11-14 | Bioxell Spa | uso de um composto de vitamina d, método de prevenção ou tratamnento de disfunção de bexiga em um paciente, composto de vitamina d, e, kit |
| 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 |
| CA2557269C (en) * | 2004-03-04 | 2012-12-04 | Kissei Pharmaceutical Co., Ltd. | Fused heterocycle derivative, medicinal composition containing the same, and medicinal use thereof |
| DE102004040168A1 (de) * | 2004-08-18 | 2006-03-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Glucopyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| CN103030617A (zh) | 2004-03-16 | 2013-04-10 | 贝林格尔.英格海姆国际有限公司 | 吡喃葡萄糖基取代的苯基衍生物、含该化合物的药物、其用途及其制造方法 |
| DE102004061145A1 (de) * | 2004-12-16 | 2006-06-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Glucopyranosyl-substituierte Benzol-Derivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| 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 |
| US20070185197A1 (en) | 2004-03-31 | 2007-08-09 | Hideki Fujikura | Phenol derivative, medicinal composition containing the same, and medicinal use thereof |
| 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 |
| 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 |
| EP1773800A1 (de) * | 2004-07-27 | 2007-04-18 | Boehringer Ingelheim International GmbH | D-glucopyranosyl-phenyl-substituierte cyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| 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) |
| 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 |
| WO2006064033A2 (en) | 2004-12-16 | 2006-06-22 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
| TW200637839A (en) * | 2005-01-07 | 2006-11-01 | Taisho Pharmaceutical Co Ltd | 1-thio-d-glucitol derivatives |
| TW200637869A (en) | 2005-01-28 | 2006-11-01 | Chugai Pharmaceutical Co Ltd | The spiroketal derivatives and the use as therapeutical agent for diabetes of the same |
| CA2595257A1 (en) * | 2005-02-23 | 2006-08-31 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted ((hetero)arylethynyl-benzyl)-benzene derivatives and use thereof as sodium-dependent glucose cotransporter 2 (sglt2) inhibitors |
| US7975805B2 (en) | 2005-04-01 | 2011-07-12 | Oil-Rite Corporation | Lubrication system |
| JP5238492B2 (ja) * | 2005-04-15 | 2013-07-17 | 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 | Ｓｇｌｔインヒビターとしてのグルコピラノシル置換（ヘテロアリールオキシ−ベンジル）−ベンゼン誘導体 |
| 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 |
| US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| 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 |
| ATE484499T1 (de) | 2005-08-30 | 2010-10-15 | Boehringer Ingelheim Int | Glucopyranosyl-substituierte benzyl-derivate, medikamente mit solchen verbindungen, ihre verwendung und herstellungsverfahren dafür |
| CA2621314A1 (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 |
| AR061026A1 (es) | 2006-05-19 | 2008-07-30 | Taisho Pharmaceutical Co Ltd | Compuesto glicitol c-fenilo y preparacion farmaceutica |
| JP4809931B2 (ja) | 2007-08-23 | 2011-11-09 | セラコス・インコーポレイテッド | ベンジルベンゼン誘導体およびその使用方法 |
| EP2324002B1 (en) * | 2008-08-22 | 2016-10-05 | Theracos Sub, LLC | Processes for the preparation of sglt2 inhibitors |
-
2008
- 2008-08-22 JP JP2010522073A patent/JP4809931B2/ja active Active
- 2008-08-22 UA UAA201003326A patent/UA99924C2/ru unknown
- 2008-08-22 CA CA2697349A patent/CA2697349C/en active Active
- 2008-08-22 HU HUE08798514A patent/HUE035947T2/hu unknown
- 2008-08-22 DK DK08798514.9T patent/DK2187742T3/en active
- 2008-08-22 SI SI200831898T patent/SI2187742T1/en unknown
- 2008-08-22 WO PCT/US2008/074058 patent/WO2009026537A1/en not_active Ceased
- 2008-08-22 PL PL08798514T patent/PL2187742T3/pl unknown
- 2008-08-22 US US12/197,095 patent/US7838499B2/en active Active
- 2008-08-22 KR KR1020107006207A patent/KR101107425B1/ko active Active
- 2008-08-22 LT LTEP08798514.9T patent/LT2187742T/lt unknown
- 2008-08-22 NZ NZ583369A patent/NZ583369A/en unknown
- 2008-08-22 MX MX2010002027A patent/MX2010002027A/es active IP Right Grant
- 2008-08-22 EP EP08798514.9A patent/EP2187742B1/en active Active
- 2008-08-22 HR HRP20180127TT patent/HRP20180127T1/hr unknown
- 2008-08-22 RS RS20180074A patent/RS56822B1/sr unknown
- 2008-08-22 ES ES08798514.9T patent/ES2654894T3/es active Active
- 2008-08-22 PT PT87985149T patent/PT2187742T/pt unknown
- 2008-08-22 RU RU2010110829/15A patent/RU2497526C2/ru active
- 2008-08-22 AR ARP080103675A patent/AR068016A1/es active IP Right Grant
- 2008-08-22 AU AU2008288770A patent/AU2008288770B2/en active Active
- 2008-08-22 EP EP17190414.7A patent/EP3318562A3/en not_active Withdrawn
- 2008-08-22 NO NO08798514A patent/NO2187742T3/no unknown
- 2008-08-22 CN CN200880104132.1A patent/CN101790311B/zh active Active
- 2008-08-22 BR BRPI0815708A patent/BRPI0815708B8/pt active IP Right Grant
- 2008-08-22 SG SG2013012877A patent/SG188800A1/en unknown
- 2008-08-22 TW TW097132255A patent/TWI434691B/zh active
-
2010
- 2010-02-11 IL IL203915A patent/IL203915A/en active IP Right Grant
- 2010-02-12 ZA ZA2010/01051A patent/ZA201001051B/en unknown
- 2010-11-01 US US12/917,367 patent/US8106021B2/en active Active
-
2011
- 2011-12-21 US US13/333,295 patent/US8575321B2/en active Active
-
2013
- 2013-09-30 US US14/042,408 patent/US8802637B2/en active Active
-
2018
- 2018-01-22 CY CY20181100079T patent/CY1119810T1/el unknown
- 2018-02-06 AR ARP180100278A patent/AR110796A2/es unknown
- 2018-11-01 HK HK18113993.0A patent/HK1254895A1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010536882A5 (OSRAM) | ||
| CN108055842B (zh) | 亚磺酰基苯基或磺亚胺酰基苯基苯并氮杂䓬 | |
| ES2950424T3 (es) | Compuesto de amida | |
| AU2010240200B2 (en) | Novel thyroid hormone beta receptor agonist | |
| JP7013245B2 (ja) | トレプロスチニル誘導体ならびにその組成物および使用 | |
| JP2021185206A (ja) | チエノピリミジンジオンａｃｃ阻害剤の固体形態およびその生成のための方法 | |
| US10093629B2 (en) | Heterocyclic compounds and their use as retinoid-related orphan receptor (ROR) gamma-T inhibitors | |
| RU2768149C2 (ru) | ПРОИЗВОДНЫЕ АМИДА В КАЧЕСТВЕ БЛОКАТОРОВ Nav1.7 И Nav1.8 | |
| CA2697349A1 (en) | Benzylbenzene derivatives and methods of use | |
| JP2017504572A (ja) | 肝臓癌治療のためのヌクレオチド類 | |
| EP3174860B1 (en) | Substituted dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity | |
| US11339142B2 (en) | Di-substituted pyrazole compounds for the treatment of diseases | |
| US20180319812A1 (en) | Heterocyclic compound | |
| JP2013527170A (ja) | 新規免疫調節剤および抗炎症化合物 | |
| TW201936585A (zh) | 5-氟尿嘧啶化合物 | |
| US20190134017A1 (en) | Di-substituted pyrazole compounds for the treatment of diseases | |
| CN111093658A (zh) | 用于治疗皮肤疾病的稠合杂芳环-苯胺化合物 | |
| JPWO2008108486A1 (ja) | １−ビアリールアゼチジノン誘導体 | |
| KR102420210B1 (ko) | 치환된 바이사이클릭 디하이드로피리미디논 및 호중구 엘라스타제 활성 억제제로서의 이의 용도 | |
| KR20220056219A (ko) | 병용 의약에 의한 당뇨병의 치료 또는 예방 방법 | |
| EP2867215B1 (en) | Tetrazole derivatives and their use as potassium channel modulators | |
| EP4587429A1 (en) | Substituted oxoisoindolinyl piperidine-2,6-dione compounds | |
| KR102377981B1 (ko) | 폐 섬유증 치료용 조성물 | |
| KR20250093525A (ko) | 상처 치료를 위한 2-치환된 3,4a,5,7,8,8a-헥사하이드로-4h-티오피라노[4,3-d]피리미딘-4-온 | |
| EP3189060A1 (fr) | Derives de n-aryl-2-amino-4-aryl-pyrimidines polyethers macrocycliques comme inhibiteurs de la ftl3 and jak |