JP2011506469A5 - - Google Patents
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- JP2011506469A5 JP2011506469A5 JP2010538165A JP2010538165A JP2011506469A5 JP 2011506469 A5 JP2011506469 A5 JP 2011506469A5 JP 2010538165 A JP2010538165 A JP 2010538165A JP 2010538165 A JP2010538165 A JP 2010538165A JP 2011506469 A5 JP2011506469 A5 JP 2011506469A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- group
- alkyloxy
- alkenyl
- 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
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- -1 cyano, amino Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 23
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 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 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 9
- 239000000460 chlorine Substances 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 206010012601 diabetes mellitus Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 5
- 239000004480 active ingredient Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 201000001431 Hyperuricemia Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010030113 Oedema Diseases 0.000 claims 2
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims 2
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims 2
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 2
- 201000008980 hyperinsulinism Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- OKFBOLRSXHCDET-GKZPLSAOSA-N (1r,2r,3s,4r,5r,6s)-4-[4-chloro-3-[[4-(1-hydroxyethyl)phenyl]methyl]phenyl]-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetrol 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 OKFBOLRSXHCDET-GKZPLSAOSA-N 0.000 claims 1
- UWNNGHCXCMEVKY-LCNLMQJVSA-N (1r,2r,3s,4s,6r)-4-[4-chloro-3-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)-5-methylidenecyclohexane-1,2,3-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@@H]2C([C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C)=CC=C1Cl UWNNGHCXCMEVKY-LCNLMQJVSA-N 0.000 claims 1
- 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 1
- ZOECHXYUVRRUJW-GMISPTPDSA-N (4r,5r,6r,7s,8s)-8-[4-chloro-3-[(4-ethylphenyl)methyl]phenyl]-4-(hydroxymethyl)spiro[2.5]octane-5,6,7-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@@H]2C3(CC3)[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC=C1Cl ZOECHXYUVRRUJW-GMISPTPDSA-N 0.000 claims 1
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy 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
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 1
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229940116269 uric acid Drugs 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
Images
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1351707P | 2007-12-13 | 2007-12-13 | |
| US61/013,517 | 2007-12-13 | ||
| PCT/US2008/086472 WO2009076550A1 (en) | 2007-12-13 | 2008-12-11 | Benzylphenyl cyclohexane derivatives and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011506469A JP2011506469A (ja) | 2011-03-03 |
| JP2011506469A5 true JP2011506469A5 (enExample) | 2012-02-02 |
| JP5507464B2 JP5507464B2 (ja) | 2014-05-28 |
Family
ID=40754059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010538165A Expired - Fee Related JP5507464B2 (ja) | 2007-12-13 | 2008-12-11 | ベンジルフェニルシクロヘキサン誘導体およびその使用方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8129434B2 (enExample) |
| EP (1) | EP2230907B1 (enExample) |
| JP (1) | JP5507464B2 (enExample) |
| KR (1) | KR101567969B1 (enExample) |
| CN (1) | CN101938902B (enExample) |
| AR (2) | AR071268A1 (enExample) |
| AU (1) | AU2008335080B2 (enExample) |
| BR (1) | BRPI0819930A2 (enExample) |
| CA (1) | CA2707909C (enExample) |
| IL (1) | IL206234A0 (enExample) |
| NZ (1) | NZ586639A (enExample) |
| RU (1) | RU2505521C2 (enExample) |
| TW (1) | TWI426081B (enExample) |
| UA (1) | UA101004C2 (enExample) |
| WO (1) | WO2009076550A1 (enExample) |
| ZA (1) | ZA201004400B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102149280B (zh) * | 2008-07-15 | 2017-05-24 | 泰拉科斯有限公司 | 氘化苄基苯衍生物及其使用方法 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| BR112013030163A2 (pt) * | 2011-05-26 | 2017-03-01 | Tfchem | composto, uso cosmético de pelo menos um composto, composição farmacêutica ou cosmética e processo para preparar um composto. |
| 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 |
| 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 |
| WO2015051484A1 (en) | 2013-10-12 | 2015-04-16 | Theracos, Inc. | Preparation of hydroxy-benzylbenzene derivatives |
| 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 |
| 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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-
2008
- 2008-11-12 UA UAA201008620A patent/UA101004C2/uk unknown
- 2008-12-11 CA CA2707909A patent/CA2707909C/en not_active Expired - Fee Related
- 2008-12-11 US US12/333,190 patent/US8129434B2/en not_active Expired - Fee Related
- 2008-12-11 EP EP08859426.2A patent/EP2230907B1/en active Active
- 2008-12-11 WO PCT/US2008/086472 patent/WO2009076550A1/en not_active Ceased
- 2008-12-11 CN CN200880126441.9A patent/CN101938902B/zh not_active Expired - Fee Related
- 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
- 2008-12-11 JP JP2010538165A patent/JP5507464B2/ja not_active Expired - Fee Related
- 2008-12-11 KR KR1020107015420A patent/KR101567969B1/ko not_active Expired - Fee Related
- 2008-12-11 NZ NZ586639A patent/NZ586639A/en not_active IP Right Cessation
- 2008-12-11 BR BRPI0819930A patent/BRPI0819930A2/pt not_active IP Right Cessation
- 2008-12-12 AR ARP080105417A patent/AR071268A1/es not_active Application Discontinuation
-
2010
- 2010-06-07 IL IL206234A patent/IL206234A0/en unknown
- 2010-06-22 ZA ZA2010/04400A patent/ZA201004400B/en unknown
-
2018
- 2018-02-21 AR ARP180100403A patent/AR113211A2/es unknown
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