UA71994C2 - Glucopyranosyloxypyrazole derivatives, a pharmaceutical composition containing these derivatives and intermediate compounds for the preparation thereof - Google Patents
Glucopyranosyloxypyrazole derivatives, a pharmaceutical composition containing these derivatives and intermediate compounds for the preparation thereof Download PDFInfo
- Publication number
- UA71994C2 UA71994C2 UA2002032522A UA2002032522A UA71994C2 UA 71994 C2 UA71994 C2 UA 71994C2 UA 2002032522 A UA2002032522 A UA 2002032522A UA 2002032522 A UA2002032522 A UA 2002032522A UA 71994 C2 UA71994 C2 UA 71994C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methyl
- glucopyranosyloxy
- pyrazole
- acetyl
- tetra
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title description 113
- 239000008194 pharmaceutical composition Substances 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 34
- 150000003839 salts Chemical class 0.000 abstract description 19
- 125000005843 halogen group Chemical group 0.000 abstract description 8
- 230000002401 inhibitory effect Effects 0.000 abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 7
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
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- 102000052543 human SLC5A2 Human genes 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003449 preventive effect Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 108
- 238000005481 NMR spectroscopy Methods 0.000 description 71
- 238000000034 method Methods 0.000 description 63
- -1 methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tertpentyloxy group Chemical group 0.000 description 35
- 239000002904 solvent Substances 0.000 description 33
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- 108020001507 fusion proteins Proteins 0.000 description 1
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- 230000030279 gene silencing Effects 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 238000002955 isolation Methods 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
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- 229930182823 kanamycin A Natural products 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 125000005905 mesyloxy group Chemical group 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- FVEINXLJOJPHLH-UHFFFAOYSA-N p-tert-Butylbenzyl alcohol Chemical compound CC(C)(C)C1=CC=C(CO)C=C1 FVEINXLJOJPHLH-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 108090000765 processed proteins & peptides Proteins 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 108091008146 restriction endonucleases Proteins 0.000 description 1
- 238000010839 reverse transcription Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
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- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 238000012546 transfer Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011534 wash buffer Substances 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)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24680099 | 1999-08-31 | ||
| PCT/JP2000/005678 WO2001016147A1 (fr) | 1999-08-31 | 2000-08-24 | Derives de glucopyranosyloxypyrazole, compositions medicinales renfermant lesdits derives et produits intermediaires obtenus au cours de leur production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA71994C2 true UA71994C2 (en) | 2005-01-17 |
Family
ID=17153879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002032522A UA71994C2 (en) | 1999-08-31 | 2000-08-24 | Glucopyranosyloxypyrazole derivatives, a pharmaceutical composition containing these derivatives and intermediate compounds for the preparation thereof |
Country Status (29)
| Country | Link |
|---|---|
| US (4) | US6972283B2 (de) |
| EP (1) | EP1213296B1 (de) |
| JP (1) | JP3989730B2 (de) |
| KR (1) | KR100591585B1 (de) |
| CN (1) | CN1145635C (de) |
| AT (1) | ATE264337T1 (de) |
| AU (1) | AU782330B2 (de) |
| BG (1) | BG65388B1 (de) |
| BR (1) | BRPI0013667B8 (de) |
| CA (1) | CA2382480C (de) |
| CZ (1) | CZ303372B6 (de) |
| DE (1) | DE60009929T2 (de) |
| DK (1) | DK1213296T3 (de) |
| ES (1) | ES2216937T3 (de) |
| HK (1) | HK1050369A1 (de) |
| HU (1) | HU229581B1 (de) |
| IL (2) | IL148384A0 (de) |
| MX (1) | MXPA02002271A (de) |
| NO (1) | NO322703B1 (de) |
| NZ (1) | NZ517439A (de) |
| PL (1) | PL203124B1 (de) |
| PT (1) | PT1213296E (de) |
| RU (1) | RU2232767C2 (de) |
| SK (1) | SK286600B6 (de) |
| TR (1) | TR200201082T2 (de) |
| TW (1) | TW579378B (de) |
| UA (1) | UA71994C2 (de) |
| WO (1) | WO2001016147A1 (de) |
| ZA (1) | ZA200201991B (de) |
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| WO2024184293A1 (en) | 2023-03-06 | 2024-09-12 | Boehringer Ingelheim Vetmedica Gmbh | Systems for delivery of liquid pharmaceutical compositions in particular comprising one or more sglt-2 inhibitor(s) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5274111A (en) * | 1992-04-07 | 1993-12-28 | American Home Products Corporation | Trifluoromethyl substituted 1H-pyrazoles and derivatives thereof |
| US5264451A (en) * | 1992-04-07 | 1993-11-23 | American Home Products Corporation | Process for treating hyperglycemia using trifluoromethyl substituted 3H-pyrazol-3-ones |
| JP3915116B2 (ja) * | 2000-11-02 | 2007-05-16 | 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 |
| EP1432720A1 (de) | 2001-09-05 | 2004-06-30 | Bristol-Myers Squibb Company | Inhibitoren von o-pyrazolglucosid-sglt2 und anwendungsverfahren |
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2000
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- 2000-08-24 TR TR2002/01082T patent/TR200201082T2/xx unknown
- 2000-08-24 WO PCT/JP2000/005678 patent/WO2001016147A1/ja active IP Right Grant
- 2000-08-24 KR KR1020027002744A patent/KR100591585B1/ko active IP Right Grant
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- 2000-08-24 EP EP00954963A patent/EP1213296B1/de not_active Expired - Lifetime
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- 2000-08-24 JP JP2001519711A patent/JP3989730B2/ja not_active Expired - Fee Related
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2004
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