UA73606C2 - Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing them - Google Patents

Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing them Download PDF

Info

Publication number: UA73606C2
Authority: UA; Ukraine
Prior art keywords: group; alkyl group; lower alkyl; glucopyranosyloxybenzylbenzene; general formula
Prior art date: 2000-09-29

Application number

UA2003032735A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Kissei Pharmaceutical

Priority date (The priority date 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 date listed.)

2000-09-29

Filing date

2001-09-21

Publication date

2005-08-15

2001-09-21 Application filed by Kissei Pharmaceutical filed Critical Kissei Pharmaceutical

2005-08-15 Publication of UA73606C2 publication Critical patent/UA73606C2/uk

Links

239000000203 mixture Substances 0.000 title claims description 38
125000000217 alkyl group Chemical group 0.000 claims abstract description 42
125000003545 alkoxy group Chemical group 0.000 claims abstract description 38
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 18
229940002612 prodrug Drugs 0.000 claims abstract description 14
239000000651 prodrug Substances 0.000 claims abstract description 14
201000010099 disease Diseases 0.000 claims abstract description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
201000001421 hyperglycemia Diseases 0.000 claims abstract description 11
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 10
208000008589 Obesity Diseases 0.000 claims abstract description 7
235000020824 obesity Nutrition 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims description 32
125000002252 acyl group Chemical group 0.000 claims description 21
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
239000008194 pharmaceutical composition Substances 0.000 claims description 16
230000002265 prevention Effects 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
208000002249 Diabetes Complications Diseases 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
238000012876 topography Methods 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 12
230000000694 effects Effects 0.000 abstract description 9
101000716682 Homo sapiens Sodium/glucose cotransporter 2 Proteins 0.000 abstract 1
102000052543 human SLC5A2 Human genes 0.000 abstract 1
238000001727 in vivo Methods 0.000 abstract 1
230000003449 preventive effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
150000001875 compounds Chemical class 0.000 description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
239000002904 solvent Substances 0.000 description 38
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
-1 methoxy, ethoxy, propoxy Chemical group 0.000 description 25
238000005160 1H NMR spectroscopy Methods 0.000 description 24
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 19
239000008103 glucose Substances 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
230000002829 reductive effect Effects 0.000 description 17
238000012360 testing method Methods 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
239000003480 eluent Substances 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
239000007853 buffer solution Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
210000002700 urine Anatomy 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
238000004440 column chromatography Methods 0.000 description 11
230000008569 process Effects 0.000 description 11
239000012044 organic layer Substances 0.000 description 10
241000700159 Rattus Species 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
239000007818 Grignard reagent Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000004821 distillation Methods 0.000 description 8
150000004795 grignard reagents Chemical class 0.000 description 8
210000002381 plasma Anatomy 0.000 description 8
239000002994 raw material Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
239000008280 blood Substances 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000003814 drug Substances 0.000 description 7
230000035484 reaction time Effects 0.000 description 7
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 6
ALZWVPLMSWPDQR-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methyl]phenol Chemical compound C1=CC(OC)=CC=C1CC1=CC=CC=C1O ALZWVPLMSWPDQR-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
239000012634 fragment Substances 0.000 description 6
YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
238000005259 measurement Methods 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
238000010253 intravenous injection Methods 0.000 description 5
210000003734 kidney Anatomy 0.000 description 5
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
210000003462 vein Anatomy 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
230000009102 absorption Effects 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
239000003472 antidiabetic agent Substances 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
230000009103 reabsorption Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000725 suspension Substances 0.000 description 4
BMPXABNSIVCIID-UHFFFAOYSA-N 2-[(4-ethoxyphenyl)methyl]phenol Chemical compound C1=CC(OCC)=CC=C1CC1=CC=CC=C1O BMPXABNSIVCIID-UHFFFAOYSA-N 0.000 description 3
ZCGMETLZAJTKEN-UHFFFAOYSA-N 2-[(4-ethylsulfanylphenyl)methyl]phenol Chemical compound C1=CC(SCC)=CC=C1CC1=CC=CC=C1O ZCGMETLZAJTKEN-UHFFFAOYSA-N 0.000 description 3
XOIYJTQUSZANDW-UHFFFAOYSA-N 2-[[4-(2-methylpropyl)phenyl]methyl]phenol Chemical compound C1=CC(CC(C)C)=CC=C1CC1=CC=CC=C1O XOIYJTQUSZANDW-UHFFFAOYSA-N 0.000 description 3
239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
229910015900 BF3 Inorganic materials 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
235000019743 Choline chloride Nutrition 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000010171 animal model Methods 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
239000001768 carboxy methyl cellulose Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 3
229960003178 choline chloride Drugs 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
230000029142 excretion Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
229910001629 magnesium chloride Inorganic materials 0.000 description 3
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000013612 plasmid Substances 0.000 description 3
239000001103 potassium chloride Substances 0.000 description 3
235000011164 potassium chloride Nutrition 0.000 description 3
238000012746 preparative thin layer chromatography Methods 0.000 description 3
238000012545 processing Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
UKIIQMFGVQQBEY-UHFFFAOYSA-N 2-[(4-propan-2-yloxyphenyl)methyl]phenol Chemical compound C1=CC(OC(C)C)=CC=C1CC1=CC=CC=C1O UKIIQMFGVQQBEY-UHFFFAOYSA-N 0.000 description 2
LXPWGAZYJHUWPM-UHFFFAOYSA-N 4-(2-methylpropyl)benzaldehyde Chemical compound CC(C)CC1=CC=C(C=O)C=C1 LXPWGAZYJHUWPM-UHFFFAOYSA-N 0.000 description 2
UHLRPXXFPYMCAE-UHFFFAOYSA-N 4-isopropylcalix[4]arene Chemical compound C1C(C=2O)=CC(C(C)C)=CC=2CC(C=2O)=CC(C(C)C)=CC=2CC(C=2O)=CC(C(C)C)=CC=2CC2=CC(C(C)C)=CC1=C2O UHLRPXXFPYMCAE-UHFFFAOYSA-N 0.000 description 2
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229940123208 Biguanide Drugs 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
102000016928 DNA-directed DNA polymerase Human genes 0.000 description 2
108010014303 DNA-directed DNA polymerase Proteins 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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229940100389 Sulfonylurea Drugs 0.000 description 2
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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235000013305 food Nutrition 0.000 description 2
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229930182478 glucoside Natural products 0.000 description 2
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239000008187 granular material Substances 0.000 description 2
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
230000002218 hypoglycaemic effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
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239000013600 plasmid vector Substances 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
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239000012279 sodium borohydride Substances 0.000 description 2
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125000001424 substituent group Chemical group 0.000 description 2
208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
239000013598 vector Substances 0.000 description 2
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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)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Diabetes (AREA)
Molecular Biology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Genetics & Genomics (AREA)
Obesity (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Hematology (AREA)
Epidemiology (AREA)
Child & Adolescent Psychology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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UA2003032735A 2000-09-29 2001-09-21 Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing them UA73606C2 (en)

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JP2000301523		2000-09-29
PCT/JP2001/008239 WO2002028872A1 (fr)	2000-09-29	2001-09-21	Derives de glucopyranosiloxybenzylbenzene et compositions therapeutiques contenant ces composes

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JP (1)	JP3798375B2 (es)
KR (1)	KR100647204B1 (es)
CN (1)	CN1293087C (es)
AR (1)	AR030816A1 (es)
AT (1)	ATE335753T1 (es)
AU (2)	AU2001290257B2 (es)
BG (1)	BG66015B1 (es)
BR (1)	BR0114310A (es)
CA (1)	CA2423568C (es)
CY (1)	CY1106076T1 (es)
CZ (1)	CZ303544B6 (es)
DE (1)	DE60122193T2 (es)
DK (1)	DK1329456T3 (es)
EA (1)	EA005994B1 (es)
ES (1)	ES2269456T3 (es)
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PT (1)	PT1329456E (es)
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TW (1)	TWI284641B (es)
UA (1)	UA73606C2 (es)
WO (1)	WO2002028872A1 (es)
ZA (1)	ZA200302283B (es)

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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
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Publication number	Publication date
EP1329456B1 (en)	2006-08-09
BR0114310A (pt)	2003-10-14
WO2002028872A1 (fr)	2002-04-11
KR100647204B1 (ko)	2006-11-17
HUP0301178A3 (en)	2009-08-28
JPWO2002028872A1 (ja)	2004-02-12
ZA200302283B (en)	2005-05-27
PL205607B1 (pl)	2010-05-31
NO327182B1 (no)	2009-05-04
CN1466590A (zh)	2004-01-07
BG66015B1 (bg)	2010-10-29
AU9025701A (en)	2002-04-15
DE60122193T2 (de)	2007-07-05
IL155071A0 (en)	2003-10-31
BG107674A (bg)	2004-01-30
HK1061037A1 (en)	2004-09-03
PT1329456E (pt)	2006-12-29
PL362177A1 (en)	2004-10-18
DK1329456T3 (da)	2006-12-04
NO20031407D0 (no)	2003-03-27
ES2269456T3 (es)	2007-04-01
AR030816A1 (es)	2003-09-03
EA200300316A1 (ru)	2003-08-28
AU2001290257B2 (en)	2007-08-30
SI1329456T1 (sl)	2006-12-31
IL155071A (en)	2010-04-15
US20040018998A1 (en)	2004-01-29
CA2423568C (en)	2011-03-15
TWI284641B (en)	2007-08-01
PE20020476A1 (es)	2002-07-04
CA2423568A1 (en)	2002-04-11
US6872706B2 (en)	2005-03-29
EP1329456A4 (en)	2005-03-30
EA005994B1 (ru)	2005-08-25
JP3798375B2 (ja)	2006-07-19
NO20031407L (no)	2003-04-30
KR20030036867A (ko)	2003-05-09
SK287811B6 (sk)	2011-10-04
SK3342003A3 (en)	2003-08-05
HUP0301178A2 (hu)	2003-11-28
CY1106076T1 (el)	2011-06-08
MXPA03002779A (es)	2004-05-04
EP1329456A1 (en)	2003-07-23
DE60122193D1 (de)	2006-09-21
CN1293087C (zh)	2007-01-03
NZ524917A (en)	2005-01-28
CZ303544B6 (cs)	2012-11-28
US20050065098A1 (en)	2005-03-24
MY129023A (en)	2007-03-30
ATE335753T1 (de)	2006-09-15

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CN102643256B (zh)	2014-12-24	一种芳基糖苷类化合物及其制备方法和应用
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