ZA200201991B - Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof. - Google Patents
Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof. Download PDFInfo
- Publication number
- ZA200201991B ZA200201991B ZA200201991A ZA200201991A ZA200201991B ZA 200201991 B ZA200201991 B ZA 200201991B ZA 200201991 A ZA200201991 A ZA 200201991A ZA 200201991 A ZA200201991 A ZA 200201991A ZA 200201991 B ZA200201991 B ZA 200201991B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- lower alkyl
- represented
- general formula
- alkyl group
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 5
- 239000000543 intermediate Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 101000716682 Homo sapiens Sodium/glucose cotransporter 2 Proteins 0.000 claims description 5
- 102000052543 human SLC5A2 Human genes 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- KTFGWHSLIOZEKH-UHFFFAOYSA-N 5-benzyl-1h-pyrazole Chemical class C=1C=CC=CC=1CC1=CC=NN1 KTFGWHSLIOZEKH-UHFFFAOYSA-N 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims 2
- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- -1 propylthio group Chemical group 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 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 10
- 239000008103 glucose Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 5
- 238000007126 N-alkylation reaction Methods 0.000 description 4
- 229940125708 antidiabetic agent Drugs 0.000 description 4
- 239000003472 antidiabetic agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005858 glycosidation reaction Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229940123208 Biguanide Drugs 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 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
- 239000003814 drug Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000009103 reabsorption Effects 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- OSDLDYCKEYCPPZ-UHFFFAOYSA-N 4-[(4-methylsulfanylphenyl)methyl]-5-(trifluoromethyl)-1,2-dihydropyrazol-3-one Chemical compound C1=CC(SC)=CC=C1CC1=C(C(F)(F)F)NNC1=O OSDLDYCKEYCPPZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 102000034534 Cotransporters Human genes 0.000 description 1
- 108020003264 Cotransporters Proteins 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 108091006269 SLC5A2 Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 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
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 230000000062 effect on obesity Effects 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000009207 exercise therapy Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 208000006443 lactic acidosis Diseases 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
- 210000000512 proximal kidney tubule Anatomy 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 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
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(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
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- 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
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
Landscapes
- 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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Biotechnology (AREA)
- Obesity (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24680099 | 1999-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200201991B true ZA200201991B (en) | 2003-05-28 |
Family
ID=17153879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200201991A ZA200201991B (en) | 1999-08-31 | 2002-03-11 | Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof. |
Country Status (28)
| Country | Link |
|---|---|
| US (4) | US6972283B2 (cs) |
| EP (1) | EP1213296B1 (cs) |
| JP (1) | JP3989730B2 (cs) |
| KR (1) | KR100591585B1 (cs) |
| CN (1) | CN1145635C (cs) |
| AT (1) | ATE264337T1 (cs) |
| AU (1) | AU782330B2 (cs) |
| BG (1) | BG65388B1 (cs) |
| BR (1) | BRPI0013667B8 (cs) |
| CA (1) | CA2382480C (cs) |
| CZ (1) | CZ303372B6 (cs) |
| DE (1) | DE60009929T2 (cs) |
| DK (1) | DK1213296T3 (cs) |
| ES (1) | ES2216937T3 (cs) |
| HU (1) | HU229581B1 (cs) |
| IL (2) | IL148384A0 (cs) |
| MX (1) | MXPA02002271A (cs) |
| NO (1) | NO322703B1 (cs) |
| NZ (1) | NZ517439A (cs) |
| PL (1) | PL203124B1 (cs) |
| PT (1) | PT1213296E (cs) |
| RU (1) | RU2232767C2 (cs) |
| SK (1) | SK286600B6 (cs) |
| TR (1) | TR200201082T2 (cs) |
| TW (1) | TW579378B (cs) |
| UA (1) | UA71994C2 (cs) |
| WO (1) | WO2001016147A1 (cs) |
| ZA (1) | ZA200201991B (cs) |
Families Citing this family (126)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| PH12000002657B1 (en) * | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| PL205605B1 (pl) | 2000-03-17 | 2010-05-31 | Kissei Pharmaceutical | Pochodna glukopiranozyloksybenzylobenzenu, kompozycja farmaceutyczna, zastosowanie tej pochodnej do wytwarzania kompozycji oraz pochodna benzylofenolu |
| EP2163555A1 (en) | 2000-11-02 | 2010-03-17 | Ajinomoto Co., Inc. | New pyrazole derivatives and diabetic medicine containing them |
| JP4591781B2 (ja) * | 2000-11-02 | 2010-12-01 | 味の素株式会社 | 新規ピラゾール誘導体及びそれらを含有する糖尿病治療薬 |
| JP4212891B2 (ja) * | 2000-11-30 | 2009-01-21 | 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およびその製造中間体 |
| CZ305971B6 (cs) | 2000-12-28 | 2016-06-01 | Kissei Pharmaceutical Co., Ltd. | Deriváty glukopyranosyloxypyrazolu a jejich použití v léčivech |
| JP4141258B2 (ja) * | 2001-02-26 | 2008-08-27 | キッセイ薬品工業株式会社 | グルコピラノシルオキシピラゾール誘導体及びその医薬用途 |
| EP1364958B1 (en) | 2001-02-27 | 2010-09-08 | Kissei Pharmaceutical Co., Ltd. | Glycopyranosyloxypyrazole derivatives and medicinal use thereof |
| US6936590B2 (en) | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| JP4590159B2 (ja) | 2001-04-04 | 2010-12-01 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | グルコース再吸収阻害剤およびｐｐａｒモジュレーターを含んで成る併用療法 |
| JP4590158B2 (ja) | 2001-04-04 | 2010-12-01 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | グルコース再吸収阻害剤およびレチノイド−ｘ受容体モジュレーターを含んで成る併用療法 |
| AU2002254567B2 (en) | 2001-04-11 | 2007-10-11 | Bristol-Myers Squibb Company | Amino acid complexes of C-aryl glucosides for treatment of diabetes and method |
| CA2445346C (en) * | 2001-04-27 | 2010-04-06 | Ajinomoto Co., Inc. | N-substituted pyrazole-o-glycoside derivatives and therapeutic agent for diabetes containing the same |
| WO2002098893A1 (en) | 2001-05-30 | 2002-12-12 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxypyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate therefor |
| WO2003000712A1 (fr) * | 2001-06-20 | 2003-01-03 | Kissei Pharmaceutical Co., Ltd. | Derive heterocyclique azote, composition medicinale contenant ce derive, leur utilisation medicinale et intermediaire associe |
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- 2000-08-24 DK DK00954963T patent/DK1213296T3/da active
- 2000-08-24 PT PT00954963T patent/PT1213296E/pt unknown
- 2000-08-24 JP JP2001519711A patent/JP3989730B2/ja not_active Expired - Fee Related
- 2000-08-24 CZ CZ20020665A patent/CZ303372B6/cs not_active IP Right Cessation
- 2000-08-24 RU RU2002107975/04A patent/RU2232767C2/ru active
- 2000-08-24 SK SK287-2002A patent/SK286600B6/sk not_active IP Right Cessation
- 2000-08-24 CA CA002382480A patent/CA2382480C/en not_active Expired - Lifetime
- 2000-08-24 PL PL364800A patent/PL203124B1/pl unknown
- 2000-08-24 MX MXPA02002271A patent/MXPA02002271A/es active IP Right Grant
- 2000-08-24 KR KR1020027002744A patent/KR100591585B1/ko not_active Expired - Lifetime
- 2000-08-24 DE DE60009929T patent/DE60009929T2/de not_active Expired - Lifetime
- 2000-08-24 WO PCT/JP2000/005678 patent/WO2001016147A1/ja active IP Right Grant
- 2000-08-24 NZ NZ517439A patent/NZ517439A/xx not_active IP Right Cessation
- 2000-08-24 EP EP00954963A patent/EP1213296B1/en not_active Expired - Lifetime
- 2000-08-24 BR BRPI0013667A patent/BRPI0013667B8/pt not_active IP Right Cessation
- 2000-08-24 CN CNB008137722A patent/CN1145635C/zh not_active Expired - Lifetime
- 2000-08-24 TR TR2002/01082T patent/TR200201082T2/xx unknown
- 2000-08-24 IL IL14838400A patent/IL148384A0/xx unknown
- 2000-08-24 UA UA2002032522A patent/UA71994C2/uk unknown
- 2000-08-24 HU HU0203190A patent/HU229581B1/hu unknown
- 2000-08-24 ES ES00954963T patent/ES2216937T3/es not_active Expired - Lifetime
- 2000-08-24 AU AU67275/00A patent/AU782330B2/en not_active Expired
- 2000-08-24 AT AT00954963T patent/ATE264337T1/de active
- 2000-08-31 TW TW089117757A patent/TW579378B/zh not_active IP Right Cessation
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2002
- 2002-02-26 IL IL148384A patent/IL148384A/en active IP Right Grant
- 2002-02-27 NO NO20020968A patent/NO322703B1/no not_active IP Right Cessation
- 2002-02-27 BG BG106451A patent/BG65388B1/bg unknown
- 2002-03-11 ZA ZA200201991A patent/ZA200201991B/en unknown
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2004
- 2004-01-20 US US10/759,138 patent/US6972283B2/en not_active Expired - Lifetime
- 2004-11-03 US US10/979,154 patent/US20050137143A1/en not_active Abandoned
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2005
- 2005-07-27 US US11/189,832 patent/US7056892B2/en not_active Expired - Lifetime
- 2005-07-28 US US11/191,024 patent/US7115575B2/en not_active Expired - Lifetime
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