JP2007515441A5 - - Google Patents
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- JP2007515441A5 JP2007515441A5 JP2006546000A JP2006546000A JP2007515441A5 JP 2007515441 A5 JP2007515441 A5 JP 2007515441A5 JP 2006546000 A JP2006546000 A JP 2006546000A JP 2006546000 A JP2006546000 A JP 2006546000A JP 2007515441 A5 JP2007515441 A5 JP 2007515441A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- yloxy
- hydrogen
- group
- fluorine
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000011780 sodium chloride Substances 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims description 4
- 208000008466 Metabolic Disease Diseases 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229940030600 ANTIHYPERTENSIVES Drugs 0.000 claims description 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims description 2
- 229940030606 DIURETICS Drugs 0.000 claims description 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010020993 Hypoglycaemia Diseases 0.000 claims description 2
- 206010022489 Insulin resistance Diseases 0.000 claims description 2
- 208000007976 Ketosis Diseases 0.000 claims description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
- 206010027417 Metabolic acidosis Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 206010030113 Oedema Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 208000001072 Type 2 Diabetes Mellitus Diseases 0.000 claims description 2
- 230000001396 anti-anti-diuretic Effects 0.000 claims description 2
- 230000003276 anti-hypertensive Effects 0.000 claims description 2
- 239000002220 antihypertensive agent Substances 0.000 claims description 2
- 201000001320 atherosclerosis Diseases 0.000 claims description 2
- 230000000875 corresponding Effects 0.000 claims description 2
- 239000002934 diuretic Substances 0.000 claims description 2
- 201000001420 glucose metabolism disease Diseases 0.000 claims description 2
- 230000035879 hyperinsulinaemia Effects 0.000 claims description 2
- 201000001431 hyperuricemia Diseases 0.000 claims description 2
- 230000004140 ketosis Effects 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- -1 tetrahydrofuran-3-yloxy, tetrahydropyran-3-yloxy, tetrahydropyran-4-yloxy Chemical group 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 229910052731 fluorine Inorganic materials 0.000 claims 11
- 239000011737 fluorine Substances 0.000 claims 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 239000000460 chlorine Substances 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 150000001491 aromatic compounds Chemical class 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 239000011630 iodine Substances 0.000 claims 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 102100020034 SLC5A11 Human genes 0.000 claims 2
- 101710040724 SLC5A11 Proteins 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- ZKGMDPPSDSDYRJ-JEOSHJBNSA-N (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-[[4-[(3R)-oxolan-3-yl]oxyphenyl]methyl]phenoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CC(C=C1)=CC=C1O[C@H]1COCC1 ZKGMDPPSDSDYRJ-JEOSHJBNSA-N 0.000 claims 1
- ZYXUOXWUQLBQQU-YMQHIKHWSA-N (2S,3R,4S,5S,6R)-2-[2-[(4-ethynylphenyl)methyl]phenoxy]-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]1OC1=CC=CC=C1CC1=CC=C(C#C)C=C1 ZYXUOXWUQLBQQU-YMQHIKHWSA-N 0.000 claims 1
- 125000006698 (C1-C3) dialkylamino 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
- 206010012601 Diabetes mellitus Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 150000003855 acyl compounds Chemical class 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 1
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 230000003301 hydrolyzing Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 description 3
- 229920002676 Complementary DNA Polymers 0.000 description 2
- 206010058108 Dyslipidaemia Diseases 0.000 description 2
- 239000002299 complementary DNA Substances 0.000 description 2
- 206010059512 Apoptosis Diseases 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- 208000008960 Diabetic Foot Diseases 0.000 description 1
- 206010012655 Diabetic complications Diseases 0.000 description 1
- 208000001083 Kidney Disease Diseases 0.000 description 1
- 206010061227 Lipid metabolism disease Diseases 0.000 description 1
- 206010054805 Macroangiopathy Diseases 0.000 description 1
- 206010029149 Nephropathy Diseases 0.000 description 1
- 206010029151 Nephropathy Diseases 0.000 description 1
- 206010029331 Neuropathy peripheral Diseases 0.000 description 1
- 206010038436 Renal failure acute Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 206010038932 Retinopathy Diseases 0.000 description 1
- 101710040671 SLC5A1 Proteins 0.000 description 1
- 102100016744 SLC5A1 Human genes 0.000 description 1
- 101710040722 SLC5A10 Proteins 0.000 description 1
- 206010068760 Ulcers Diseases 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 230000022534 cell killing Effects 0.000 description 1
- 210000004027 cells Anatomy 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10361133A DE10361133A1 (de) | 2003-12-22 | 2003-12-22 | Glucopyranosyloxy-substituierte Aromaten, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| PCT/EP2004/014319 WO2005063785A2 (de) | 2003-12-22 | 2004-12-16 | Glucopyranosyloxy-substituierte aromaten, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007515441A JP2007515441A (ja) | 2007-06-14 |
| JP2007515441A5 true JP2007515441A5 (he) | 2008-02-07 |
Family
ID=34683870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006546000A Pending JP2007515441A (ja) | 2003-12-22 | 2004-12-16 | グルコピラノシロキシ置換芳香族化合物、前記化合物を含む医薬、それらの使用及びそれらの製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1699807A2 (he) |
| JP (1) | JP2007515441A (he) |
| CA (1) | CA2548353A1 (he) |
| DE (1) | DE10361133A1 (he) |
| WO (1) | WO2005063785A2 (he) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| ATE468347T1 (de) * | 2005-07-27 | 2010-06-15 | Boehringer Ingelheim Int | Glucopyranosyl-substituierte ((hetero)cycloalyklethynyl-benzyl)- benzenderivative und deren verwendung als inhibitoren des natriumabhängigen glucose- cotransporters (sglt) |
| PE20080697A1 (es) | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| PE20090938A1 (es) | 2007-08-16 | 2009-08-08 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un derivado de benceno sustituido con glucopiranosilo |
| UA99924C2 (en) | 2007-08-23 | 2012-10-25 | Теракос, Инк. | Benzylbenzol derivatives and using thereof |
| UA101004C2 (en) | 2007-12-13 | 2013-02-25 | Теракос, Инк. | Derivatives of benzylphenylcyclohexane and use thereof |
| WO2009096503A1 (ja) * | 2008-01-31 | 2009-08-06 | Daiichi Sankyo Company, Limited | ベンジルフェニルグルコピラノシド誘導体 |
| WO2010009243A1 (en) | 2008-07-15 | 2010-01-21 | Theracos, Inc. | Deuterated benzylbenzene derivatives and methods of use |
| TWI441831B (zh) | 2008-08-22 | 2014-06-21 | Theracos Inc | 製備ｓｇｌｔ２抑制劑之方法 |
| SG173619A1 (en) | 2009-02-13 | 2011-09-29 | Boehringer Ingelheim Int | Pharmaceutical composition comprising a sglt2 inhibitor, a dpp-iv inhibitor and optionally a further antidiabetic agent and uses thereof |
| PL2483286T3 (pl) | 2009-09-30 | 2017-04-28 | Boehringer Ingelheim International Gmbh | Sposób wytwarzania postaci krystalicznej 1-chloro-4-(β-D-glukopiranoz-1-ylo)-2-[4-((S)-tetrahydrofuran-3-yloksy)-benzylo]-benzenu |
| SI2486029T1 (sl) | 2009-09-30 | 2015-10-30 | Boehringer Ingelheim International Gmbh | Postopki za pripravo z glukopiranozilom substituiranih benzil-benzenskih derivatov |
| US10610489B2 (en) | 2009-10-02 | 2020-04-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, pharmaceutical dosage form, process for their preparation, methods for treating and uses thereof |
| WO2011153712A1 (en) | 2010-06-12 | 2011-12-15 | Theracos, Inc. | Crystalline form of benzylbenzene sglt2 inhibitor |
| AR085689A1 (es) | 2011-03-07 | 2013-10-23 | Boehringer Ingelheim Int | Composiciones farmaceuticas de metformina, linagliptina y un inhibidor de sglt-2 |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| US9192617B2 (en) | 2012-03-20 | 2015-11-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US9193751B2 (en) | 2012-04-10 | 2015-11-24 | Theracos, Inc. | Process for the preparation of benzylbenzene SGLT2 inhibitors |
| US20140303097A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| PT2981271T (pt) | 2013-04-05 | 2019-02-19 | Boehringer Ingelheim Int | Utilizações terapêuticas de empagliflozina |
| EP4000608A1 (en) | 2013-04-18 | 2022-05-25 | Boehringer Ingelheim International GmbH | Pharmaceutical composition, methods for treating and uses thereof |
| 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 |
| CN114933619B (zh) * | 2022-05-18 | 2024-03-01 | 上海科利生物医药有限公司 | 一类硫代糖苷列净类似物及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6683056B2 (en) * | 2000-03-30 | 2004-01-27 | Bristol-Myers Squibb Company | O-aryl glucoside SGLT2 inhibitors and method |
| JPWO2003011880A1 (ja) * | 2001-07-31 | 2004-11-18 | キッセイ薬品工業株式会社 | グルコピラノシルオキシベンジルベンゼン誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
-
2003
- 2003-12-22 DE DE10361133A patent/DE10361133A1/de not_active Withdrawn
-
2004
- 2004-12-16 WO PCT/EP2004/014319 patent/WO2005063785A2/de not_active Application Discontinuation
- 2004-12-16 EP EP04803932A patent/EP1699807A2/de not_active Withdrawn
- 2004-12-16 CA CA002548353A patent/CA2548353A1/en not_active Abandoned
- 2004-12-16 JP JP2006546000A patent/JP2007515441A/ja active Pending
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