NO301226B1 - Hypoglykemiske tiazolidindioner og mellomprodukter - Google Patents
Hypoglykemiske tiazolidindioner og mellomprodukter Download PDFInfo
- Publication number
- NO301226B1 NO301226B1 NO940225A NO940225A NO301226B1 NO 301226 B1 NO301226 B1 NO 301226B1 NO 940225 A NO940225 A NO 940225A NO 940225 A NO940225 A NO 940225A NO 301226 B1 NO301226 B1 NO 301226B1
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- Norway
- Prior art keywords
- formula
- methyl
- mmol
- title compound
- phenyl
- Prior art date
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- 230000002218 hypoglycaemic effect Effects 0.000 title description 13
- 239000000543 intermediate Substances 0.000 title description 7
- 229940123464 Thiazolidinedione Drugs 0.000 title description 5
- 150000001467 thiazolidinediones Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 61
- 239000008280 blood Substances 0.000 claims description 12
- 210000004369 blood Anatomy 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000003345 hyperglycaemic effect Effects 0.000 claims description 4
- 230000000260 hypercholesteremic effect Effects 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 239000007787 solid 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
- 241001465754 Metazoa Species 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 239000008103 glucose Substances 0.000 description 10
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 cholesteryl ester Chemical class 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000003472 antidiabetic agent Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 208000024172 Cardiovascular disease Diseases 0.000 description 5
- 102000004877 Insulin Human genes 0.000 description 5
- 108090001061 Insulin Proteins 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229940125396 insulin Drugs 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 201000001320 Atherosclerosis Diseases 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940126904 hypoglycaemic agent Drugs 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- SRXJZMLETPOSSJ-UHFFFAOYSA-N 1-bromo-2-propylbenzene Chemical compound CCCC1=CC=CC=C1Br SRXJZMLETPOSSJ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
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- 238000002425 crystallisation Methods 0.000 description 3
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- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- VMKAFJQFKBASMU-QGZVFWFLSA-N (r)-2-methyl-cbs-oxazaborolidine Chemical compound C([C@@H]12)CCN1B(C)OC2(C=1C=CC=CC=1)C1=CC=CC=C1 VMKAFJQFKBASMU-QGZVFWFLSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 2
- GONOHGQPZFXJOJ-SNVBAGLBSA-N 1-[(1r)-1-isocyanatoethyl]naphthalene Chemical compound C1=CC=C2C([C@H](N=C=O)C)=CC=CC2=C1 GONOHGQPZFXJOJ-SNVBAGLBSA-N 0.000 description 2
- VCTKYTBWZTZPHF-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-2-phenyl-1,3-oxazole Chemical compound ClCC1=C(C)OC(C=2C=CC=CC=2)=N1 VCTKYTBWZTZPHF-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- 229940100389 Sulfonylurea Drugs 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 108010069201 VLDL Cholesterol Proteins 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
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- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000005534 hematocrit Methods 0.000 description 2
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- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
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- 239000011780 sodium chloride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 229960002277 tolazamide Drugs 0.000 description 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73377191A | 1991-07-22 | 1991-07-22 | |
| PCT/US1992/005436 WO1993002079A1 (en) | 1991-07-22 | 1992-07-01 | Hypoglycemic thiazolidinediones and intermediates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO940225D0 NO940225D0 (no) | 1994-01-21 |
| NO940225L NO940225L (no) | 1994-01-21 |
| NO301226B1 true NO301226B1 (no) | 1997-09-29 |
Family
ID=24949048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO940225A NO301226B1 (no) | 1991-07-22 | 1994-01-21 | Hypoglykemiske tiazolidindioner og mellomprodukter |
Country Status (19)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0595868B1 (en) * | 1991-07-22 | 1998-11-25 | Pfizer Inc. | Process for the preparation of (s)-4-[3-(5-methyl-2-phenyl-4-oxazolyl)- 1-hydroxypropyl]bromobenzene |
| GB9308487D0 (en) * | 1993-04-23 | 1993-06-09 | Smithkline Beecham Plc | Novel compounds |
| NZ501163A (en) | 1997-06-18 | 2002-02-01 | Smithkline Beecham P | Treatment of diabetes with thiazolidinedione and sulphonylurea (glibenclamide, glipizide, gliclazide, glimepiride, tolazamide and tolbutamide |
| TR200101333T2 (tr) * | 1998-11-12 | 2001-10-22 | Smithkline Beecham P.L.C. | Bir ensülin sensitizörü ve başka bir anti-diyabetik maddenin değiştirilmiş salımı için farmasötik terkip. |
| AR023700A1 (es) | 1998-11-12 | 2002-09-04 | Smithkline Beecham Plc | Un procedimiento para preparar una composicion farmaceutica que comprende un sensibilizador de insulina |
| EE200100556A (et) * | 1999-04-28 | 2003-02-17 | Aventis Pharma Deutschland Gmbh | Diarüülhappe derivaat, seda sisaldav farmatseutiline kompositsioon ja ühendi kasutamine ravimite valmistamiseks |
| TW200514783A (en) * | 1999-09-22 | 2005-05-01 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method |
| EP1457490A1 (en) * | 1999-11-10 | 2004-09-15 | Takeda Chemical Industries, Ltd. | 5-membered N-heterocyclic compounds with hypoglycemic and hypolipidemic activity |
| KR100545507B1 (ko) * | 2000-05-26 | 2006-01-24 | 니뽄 신야쿠 가부시키가이샤 | 복소환 유도체 |
| GB0014969D0 (en) | 2000-06-19 | 2000-08-09 | Smithkline Beecham Plc | Novel method of treatment |
| JP2003040877A (ja) * | 2001-07-24 | 2003-02-13 | Sumika Fine Chemicals Co Ltd | ５−［６−（２−フルオロベンジルオキシ）−２−ナフチル］メチル−２，４−チアゾリジンジオンの製造方法及びその精製方法 |
| CN100402026C (zh) * | 2002-06-03 | 2008-07-16 | 诺瓦提斯公司 | 取代的氰基吡咯烷和含有它们的组合制剂用于治疗高脂血症和相关疾病的用途 |
| JP4290648B2 (ja) * | 2002-07-03 | 2009-07-08 | エフ．ホフマン−ラ ロシュ アーゲー | オキサゾール誘導体及びインスリン感作物質としてのそれらの使用 |
| US8216609B2 (en) | 2002-08-05 | 2012-07-10 | Torrent Pharmaceuticals Limited | Modified release composition of highly soluble drugs |
| US8268352B2 (en) | 2002-08-05 | 2012-09-18 | Torrent Pharmaceuticals Limited | Modified release composition for highly soluble drugs |
| US7560475B2 (en) * | 2003-09-22 | 2009-07-14 | Ono Pharmaceutical Co., Ltd. | Phenylacetic acid derivative, process for producing the same, and use |
| EP1586573B1 (en) * | 2004-04-01 | 2007-02-07 | Sanofi-Aventis Deutschland GmbH | Oxadiazolones, processes for their preparation and their use as pharmaceuticals |
| US20120094959A1 (en) | 2010-10-19 | 2012-04-19 | Bonnie Blazer-Yost | Treatment of cystic diseases |
| US10034868B2 (en) | 2014-11-04 | 2018-07-31 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the prevention and the treatment of rapidly progressive glomerulonephritis |
| CN109867765A (zh) * | 2019-02-28 | 2019-06-11 | 中山大学惠州研究院 | 一种长效缓释可降解防污聚氨酯及其制备方法 |
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| JPS5522636A (en) | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
| US4367234A (en) | 1980-07-28 | 1983-01-04 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| US4342771A (en) | 1981-01-02 | 1982-08-03 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| US4617312A (en) | 1983-01-17 | 1986-10-14 | Pfizer Inc. | Aldose reductase inhibiting 5-(2-alkoxyphenyl) thiazolidinediones |
| CN1003445B (zh) | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| WO1986007056A1 (en) | 1985-05-21 | 1986-12-04 | Pfizer Inc. | Hypoglycemic thiazolidinediones |
| FI91869C (fi) * | 1987-03-18 | 1994-08-25 | Tanabe Seiyaku Co | Menetelmä antidiabeettisena aineena käytettävien bensoksatsolijohdannaisten valmistamiseksi |
| GB8713861D0 (en) * | 1987-06-13 | 1987-07-15 | Beecham Group Plc | Compounds |
| WO1989008651A1 (en) * | 1988-03-08 | 1989-09-21 | Pfizer Inc. | Hypoglycemic thiazolidinedione derivatives |
| US5036079A (en) | 1989-12-07 | 1991-07-30 | Pfizer Inc. | Hypoglycemic thiazolidinedione derivatives |
| US5089514A (en) | 1990-06-14 | 1992-02-18 | Pfizer Inc. | 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents |
-
1992
- 1992-06-30 TW TW081105174A patent/TW222626B/zh active
- 1992-07-01 BR BR9206293A patent/BR9206293A/pt not_active Application Discontinuation
- 1992-07-01 CZ CS94124A patent/CZ282831B6/cs not_active IP Right Cessation
- 1992-07-01 JP JP5502812A patent/JPH08823B2/ja not_active Expired - Fee Related
- 1992-07-01 CA CA002111447A patent/CA2111447C/en not_active Expired - Fee Related
- 1992-07-01 HU HU9400181A patent/HUT69692A/hu unknown
- 1992-07-01 RU RU94012853/04A patent/RU2079497C1/ru not_active IP Right Cessation
- 1992-07-01 WO PCT/US1992/005436 patent/WO1993002079A1/en not_active Application Discontinuation
- 1992-07-01 AU AU22973/92A patent/AU665775B2/en not_active Ceased
- 1992-07-01 EP EP92915346A patent/EP0641338A1/en not_active Withdrawn
- 1992-07-20 PT PT100711A patent/PT100711B/pt active IP Right Grant
- 1992-07-21 MX MX9204279A patent/MX9204279A/es not_active IP Right Cessation
- 1992-07-21 ZA ZA925468A patent/ZA925468B/xx unknown
- 1992-07-21 IE IE235792A patent/IE922357A1/en not_active Application Discontinuation
- 1992-07-21 IL IL102573A patent/IL102573A/xx not_active IP Right Cessation
- 1992-07-21 NZ NZ243653A patent/NZ243653A/en unknown
- 1992-07-21 CN CN92108662A patent/CN1030195C/zh not_active Expired - Fee Related
-
1994
- 1994-01-21 NO NO940225A patent/NO301226B1/no unknown
-
1995
- 1995-06-01 US US08/458,071 patent/US6329408B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1068823A (zh) | 1993-02-10 |
| IL102573A0 (en) | 1993-01-14 |
| AU665775B2 (en) | 1996-01-18 |
| IL102573A (en) | 1997-04-15 |
| CA2111447A1 (en) | 1993-02-04 |
| US6329408B1 (en) | 2001-12-11 |
| JPH08823B2 (ja) | 1996-01-10 |
| TW222626B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-04-21 |
| CN1030195C (zh) | 1995-11-01 |
| JPH07502487A (ja) | 1995-03-16 |
| CA2111447C (en) | 2002-08-13 |
| NO940225D0 (no) | 1994-01-21 |
| EP0641338A1 (en) | 1995-03-08 |
| AU2297392A (en) | 1993-02-23 |
| PT100711B (pt) | 1999-07-30 |
| CZ12494A3 (en) | 1994-07-13 |
| WO1993002079A1 (en) | 1993-02-04 |
| HU9400181D0 (en) | 1994-05-30 |
| IE922357A1 (en) | 1993-01-27 |
| BR9206293A (pt) | 1994-11-08 |
| MX9204279A (es) | 1994-03-31 |
| ZA925468B (en) | 1994-01-21 |
| NO940225L (no) | 1994-01-21 |
| PT100711A (pt) | 1993-09-30 |
| NZ243653A (en) | 1995-02-24 |
| HUT69692A (en) | 1995-09-28 |
| CZ282831B6 (cs) | 1997-10-15 |
| RU2079497C1 (ru) | 1997-05-20 |
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