ZA200207418B - Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates for the preparation of the derivatives. - Google Patents
Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates for the preparation of the derivatives. Download PDFInfo
- Publication number
- ZA200207418B ZA200207418B ZA200207418A ZA200207418A ZA200207418B ZA 200207418 B ZA200207418 B ZA 200207418B ZA 200207418 A ZA200207418 A ZA 200207418A ZA 200207418 A ZA200207418 A ZA 200207418A ZA 200207418 B ZA200207418 B ZA 200207418B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- lower alkoxy
- hydroxy
- lower alkyl
- pharmaceutically acceptable
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims 4
- 239000000543 intermediate Substances 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 201000001421 hyperglycemia Diseases 0.000 claims description 8
- 101000716682 Homo sapiens Sodium/glucose cotransporter 2 Proteins 0.000 claims description 6
- 102000052543 human SLC5A2 Human genes 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 208000002249 Diabetes Complications Diseases 0.000 claims 6
- 206010012655 Diabetic complications Diseases 0.000 claims 3
- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 claims 1
- -1 propylthio group Chemical group 0.000 description 64
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 13
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 11
- 239000008103 glucose Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 5
- 229940125708 antidiabetic agent Drugs 0.000 description 4
- 239000003472 antidiabetic agent Substances 0.000 description 4
- 210000003734 kidney Anatomy 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 230000003405 preventing effect Effects 0.000 description 3
- 230000009103 reabsorption Effects 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- 229940123208 Biguanide Drugs 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000004283 biguanides Chemical class 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 102000034534 Cotransporters Human genes 0.000 description 1
- 108020003264 Cotransporters Proteins 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 108091006269 SLC5A2 Proteins 0.000 description 1
- 102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000009207 exercise therapy Methods 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 208000006443 lactic acidosis Diseases 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000000512 proximal kidney tubule Anatomy 0.000 description 1
- 230000030558 renal glucose absorption Effects 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005922 tert-pentoxy group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Biochemistry (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000077304 | 2000-03-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200207418B true ZA200207418B (en) | 2003-09-16 |
Family
ID=18594892
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200207418A ZA200207418B (en) | 2000-03-17 | 2002-09-16 | Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates for the preparation of the derivatives. |
Country Status (28)
Country | Link |
---|---|
US (3) | US7465712B2 (bg) |
EP (1) | EP1270584B1 (bg) |
JP (1) | JP3773450B2 (bg) |
KR (1) | KR100660738B1 (bg) |
CN (1) | CN1177857C (bg) |
AT (1) | ATE312114T1 (bg) |
AU (2) | AU2001241146B8 (bg) |
BG (1) | BG65867B1 (bg) |
BR (1) | BR0109323A (bg) |
CA (1) | CA2402609C (bg) |
CZ (1) | CZ20023023A3 (bg) |
DE (1) | DE60115623T2 (bg) |
DK (1) | DK1270584T3 (bg) |
ES (1) | ES2254376T3 (bg) |
HK (1) | HK1055973A1 (bg) |
HU (1) | HUP0300057A3 (bg) |
IL (2) | IL151757A0 (bg) |
MX (1) | MXPA02009034A (bg) |
NO (1) | NO324249B1 (bg) |
NZ (1) | NZ521369A (bg) |
PL (1) | PL205605B1 (bg) |
RU (1) | RU2254340C2 (bg) |
SK (1) | SK287183B6 (bg) |
TR (1) | TR200202200T2 (bg) |
TW (1) | TWI293305B (bg) |
UA (1) | UA72586C2 (bg) |
WO (1) | WO2001068660A1 (bg) |
ZA (1) | ZA200207418B (bg) |
Families Citing this family (84)
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CN1020944C (zh) | 1990-01-30 | 1993-05-26 | 阿图尔-费希尔股份公司费希尔厂 | 紧固件 |
US6683056B2 (en) * | 2000-03-30 | 2004-01-27 | Bristol-Myers Squibb Company | O-aryl glucoside SGLT2 inhibitors and method |
PT1329456E (pt) | 2000-09-29 | 2006-12-29 | Kissei Pharmaceutical | Derivados de glucopiranosiloxibenzilbenzeno e composições medicinais que os contêm. |
CA2429833A1 (en) | 2000-11-30 | 2002-06-06 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates in the production thereof |
TWI255817B (en) | 2001-02-14 | 2006-06-01 | Kissei Pharmaceutical | Glucopyranosyloxybenzylbenzene derivatives and medicinal use thereof |
WO2003011880A1 (fr) * | 2001-07-31 | 2003-02-13 | Kissei Pharmaceutical Co., Ltd. | Derive de glucopyranosyloxybenzylbenzene, composition medicinale contenant ce derive, usage medicinal de cette composition et produit intermediaire pour produire cette composition |
CA2476800C (en) | 2002-03-22 | 2010-08-17 | Kissei Pharmaceutical Co., Ltd. | Crystals of glucopyranosyloxybenzyl benzene derivative |
US7956041B2 (en) * | 2002-04-26 | 2011-06-07 | Ajinomoto Co., Inc. | Prophylactic and therapeutic agent of diabetes mellitus |
WO2004014931A1 (ja) | 2002-08-09 | 2004-02-19 | Taisho Pharmaceutical Co., Ltd. | アリール5−チオ−β−D−グルコピラノシド誘導体及びそれを含有する糖尿病治療薬 |
JP4651934B2 (ja) * | 2002-12-04 | 2011-03-16 | キッセイ薬品工業株式会社 | ベンジルフェノール誘導体、それを含有する医薬組成物およびその医薬用途 |
DE10258007B4 (de) | 2002-12-12 | 2006-02-09 | Sanofi-Aventis Deutschland Gmbh | Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
DE10258008B4 (de) * | 2002-12-12 | 2006-02-02 | Sanofi-Aventis Deutschland Gmbh | Heterocyclische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
RS20060320A (en) | 2003-08-01 | 2008-08-07 | Janssen Pharmaceutica N.V., | Substituted indazole-o-glucosides |
EP1679965A4 (en) | 2003-08-01 | 2009-05-27 | Janssen Pharmaceutica Nv | SUBSTITUTED FUSED HETEROCYCLIC C-GLYCOSIDES |
US7094764B2 (en) | 2003-08-01 | 2006-08-22 | Janssen Pharmaceutica N.V. | Substituted benzimidazole-, Benztriazole-, and benzimidazolone-O-glucosides |
US8785403B2 (en) | 2003-08-01 | 2014-07-22 | Mitsubishi Tanabe Pharma Corporation | Glucopyranoside compound |
TW200526678A (en) | 2003-08-01 | 2005-08-16 | Janssen Pharmaceutica Nv | Substituted indole-O-glucosides |
PL1651658T5 (pl) | 2003-08-01 | 2020-11-30 | Mitsubishi Tanabe Pharma Corporation | Nowe związki o działaniu inhibitującym transporter zależny od sodu |
UA86042C2 (en) | 2003-08-01 | 2009-03-25 | Янссен Фармацевтика Н.В. | Substituted indazole-o-glucosides |
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 |
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 |
CA2557801C (en) * | 2004-03-16 | 2013-06-25 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzol derivatives, drugs containing said compounds, the use thereof and method for the production thereof |
CA2560005A1 (en) * | 2004-03-31 | 2005-10-13 | Kissei Pharmaceutical Co., Ltd. | Phenol derivative, medicinal composition containing the same, and medicinal use thereof |
ES2581331T3 (es) | 2004-07-21 | 2016-09-05 | Kissei Pharmaceutical Co., Ltd. | Inhibidor de la progresión de una enfermedad atribuida a una acumulación anormal de grasa hepática |
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 |
EP1813611B1 (en) | 2004-11-18 | 2014-10-01 | Kissei Pharmaceutical Co., Ltd. | 1-substituted-3- beta-d-glycopyranosylated nitrogenous hetero- cyclic compounds and medicines containing the same |
CN101111508B (zh) * | 2005-01-28 | 2011-03-30 | 中外制药株式会社 | 螺缩酮衍生物及其作为糖尿病治疗药物的用途 |
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US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
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2001
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- 2001-03-15 MX MXPA02009034A patent/MXPA02009034A/es active IP Right Grant
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- 2001-03-15 AT AT01912380T patent/ATE312114T1/de active
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