NO312664B1 - Fenylalkylkarboksylsyrederivater og preparat inneholdende disse - Google Patents
Fenylalkylkarboksylsyrederivater og preparat inneholdende disse Download PDFInfo
- Publication number
- NO312664B1 NO312664B1 NO19984633A NO984633A NO312664B1 NO 312664 B1 NO312664 B1 NO 312664B1 NO 19984633 A NO19984633 A NO 19984633A NO 984633 A NO984633 A NO 984633A NO 312664 B1 NO312664 B1 NO 312664B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- carbon atoms
- chain
- phenyl
- straight
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- 239000002253 acid Substances 0.000 title claims abstract description 62
- 238000002360 preparation method Methods 0.000 title claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 114
- 150000002148 esters Chemical class 0.000 claims abstract description 60
- 150000003839 salts Chemical class 0.000 claims abstract description 49
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- -1 phenyloxy group Chemical group 0.000 claims description 201
- 125000004432 carbon atom Chemical group C* 0.000 claims description 179
- 150000001875 compounds Chemical class 0.000 claims description 171
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 12
- 229910052731 fluorine Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- 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 claims description 5
- JARTZOJGOGKJOC-UHFFFAOYSA-N 2-(ethylamino)-3-[4-[2-[1-(4-pyridin-2-ylphenyl)ethylideneamino]oxyethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(NCC)C(O)=O)=CC=C1OCCON=C(C)C1=CC=C(C=2N=CC=CC=2)C=C1 JARTZOJGOGKJOC-UHFFFAOYSA-N 0.000 claims description 4
- QKGDCNIKMVLZRW-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[1-(4-pyridin-2-ylphenyl)ethylideneamino]oxyethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCON=C(C)C1=CC=C(C=2N=CC=CC=2)C=C1 QKGDCNIKMVLZRW-UHFFFAOYSA-N 0.000 claims description 4
- SEBIIIAILVYLHO-UHFFFAOYSA-N 2-methylsulfanyl-3-[4-[2-[1-(4-pyridin-2-ylphenyl)ethylideneamino]oxyethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(SC)C(O)=O)=CC=C1OCCON=C(C)C1=CC=C(C=2N=CC=CC=2)C=C1 SEBIIIAILVYLHO-UHFFFAOYSA-N 0.000 claims description 4
- XABTVYZAGARBRV-UHFFFAOYSA-N 2-phenoxy-3-[4-[2-[1-(4-pyridin-2-ylphenyl)ethylideneamino]oxyethoxy]phenyl]propanoic acid Chemical compound C=1C=C(C=2N=CC=CC=2)C=CC=1C(C)=NOCCOC(C=C1)=CC=C1CC(C(O)=O)OC1=CC=CC=C1 XABTVYZAGARBRV-UHFFFAOYSA-N 0.000 claims description 4
- FMLYCSDUGAVXPT-UHFFFAOYSA-N 2-phenylsulfanyl-3-[4-[2-[1-(4-pyridin-2-ylphenyl)ethylideneamino]oxyethoxy]phenyl]propanoic acid Chemical compound C=1C=C(C=2N=CC=CC=2)C=CC=1C(C)=NOCCOC(C=C1)=CC=C1CC(C(O)=O)SC1=CC=CC=C1 FMLYCSDUGAVXPT-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000003345 hyperglycaemic effect Effects 0.000 claims description 4
- XEJMJGQWTAWNGU-UHFFFAOYSA-N 2-anilino-3-[4-[2-[1-(4-phenylphenyl)ethylideneamino]oxyethoxy]phenyl]propanoic acid Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(C)=NOCCOC(C=C1)=CC=C1CC(C(O)=O)NC1=CC=CC=C1 XEJMJGQWTAWNGU-UHFFFAOYSA-N 0.000 claims description 3
- BMPGWHOAGJDSBI-UHFFFAOYSA-N 3-[4-[2-[1-(4-phenylphenyl)ethylideneamino]oxyethoxy]phenyl]-2-(1h-pyrrol-2-yl)propanoic acid Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(C)=NOCCOC(C=C1)=CC=C1CC(C(O)=O)C1=CC=CN1 BMPGWHOAGJDSBI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- ZEIBRJLEXDOIQT-UHFFFAOYSA-N 2-(n-ethylanilino)-3-[4-[2-[1-(4-phenylphenyl)ethylideneamino]oxyethoxy]phenyl]propanoic acid Chemical compound C=1C=CC=CC=1N(CC)C(C(O)=O)CC(C=C1)=CC=C1OCCON=C(C)C(C=C1)=CC=C1C1=CC=CC=C1 ZEIBRJLEXDOIQT-UHFFFAOYSA-N 0.000 claims description 2
- VJTRZTOCJQPLCH-UHFFFAOYSA-N 5-phenyl-2-[[4-[2-[1-(4-pyridin-2-ylphenyl)ethylideneamino]oxyethoxy]phenyl]methyl]pentanoic acid Chemical compound C=1C=C(C=2N=CC=CC=2)C=CC=1C(C)=NOCCOC(C=C1)=CC=C1CC(C(O)=O)CCCC1=CC=CC=C1 VJTRZTOCJQPLCH-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- YGEBSPSHPLATGG-UHFFFAOYSA-N 2-(diethylamino)-3-[4-[2-[1-(4-pyridin-2-ylphenyl)ethylideneamino]oxyethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N(CC)CC)C(O)=O)=CC=C1OCCON=C(C)C1=CC=C(C=2N=CC=CC=2)C=C1 YGEBSPSHPLATGG-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 9
- 201000001421 hyperglycemia Diseases 0.000 abstract description 8
- 230000003449 preventive effect Effects 0.000 abstract description 5
- 230000001225 therapeutic effect Effects 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 106
- 238000006243 chemical reaction Methods 0.000 description 104
- 238000001228 spectrum Methods 0.000 description 95
- 238000005160 1H NMR spectroscopy Methods 0.000 description 94
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 92
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
- 239000000203 mixture Substances 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 235000019441 ethanol Nutrition 0.000 description 35
- 239000002904 solvent Substances 0.000 description 35
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 238000010626 work up procedure Methods 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- 125000006239 protecting group Chemical group 0.000 description 17
- 238000011282 treatment Methods 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 150000002170 ethers Chemical class 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- 206010012601 diabetes mellitus Diseases 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
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- 239000002585 base Substances 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
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- 229960003975 potassium Drugs 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 229940036310 program Drugs 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- BEIZGHVXYDZHOP-UHFFFAOYSA-M sodium;2-[[4-[2-[1-(4-pyridin-2-ylphenyl)ethylideneamino]oxyethoxy]phenyl]methyl]hexanoate Chemical compound [Na+].C1=CC(CC(CCCC)C([O-])=O)=CC=C1OCCON=C(C)C1=CC=C(C=2N=CC=CC=2)C=C1 BEIZGHVXYDZHOP-UHFFFAOYSA-M 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 208000005057 thyrotoxicosis Diseases 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/02—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/58—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/45—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms doubly-bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8280396 | 1996-04-04 | ||
PCT/JP1997/001122 WO1997037970A1 (fr) | 1996-04-04 | 1997-04-01 | Derives d'acide phenylalkylcarboxylique |
Publications (3)
Publication Number | Publication Date |
---|---|
NO984633D0 NO984633D0 (no) | 1998-10-02 |
NO984633L NO984633L (no) | 1998-12-03 |
NO312664B1 true NO312664B1 (no) | 2002-06-17 |
Family
ID=13784577
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19984633A NO312664B1 (no) | 1996-04-04 | 1998-10-02 | Fenylalkylkarboksylsyrederivater og preparat inneholdende disse |
Country Status (17)
Country | Link |
---|---|
US (1) | US6103907A (de) |
EP (1) | EP0916651B1 (de) |
KR (1) | KR20000005224A (de) |
CN (1) | CN1104413C (de) |
AT (1) | ATE252074T1 (de) |
AU (1) | AU708919B2 (de) |
CA (1) | CA2251468A1 (de) |
CZ (1) | CZ318098A3 (de) |
DE (1) | DE69725585T2 (de) |
DK (1) | DK0916651T3 (de) |
ES (1) | ES2207719T3 (de) |
HK (1) | HK1020716A1 (de) |
NO (1) | NO312664B1 (de) |
NZ (1) | NZ332136A (de) |
PT (1) | PT916651E (de) |
RU (1) | RU2169141C2 (de) |
WO (1) | WO1997037970A1 (de) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MXPA00004036A (es) | 1997-10-27 | 2006-05-24 | Reddys Lab Ltd Dr | Compuestos triciclicos novedosos y su uso en medicina; proceso para su preparacion y composiciones farmaceuticas que los contienen.. |
GB2380997B (en) * | 1997-10-27 | 2003-07-02 | Reddys Lab Ltd Dr | Novel aryl-oxysubstituted alkyl carboxylic acids; process for their preparation and pharmaceutical compositions containing them |
ATE272625T1 (de) | 1998-05-11 | 2004-08-15 | Takeda Chemical Industries Ltd | Oxyiminoalkansäure derivate mit hypoglykämischer und hypolipidemischer wirkung |
SE9801990D0 (sv) | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl propionic acid derivatives and analogs |
SE9801992D0 (sv) * | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl-2-hydroxypropionic acid derivative I |
GB9821061D0 (en) * | 1998-09-28 | 1998-11-18 | Celltech Therapeutics Ltd | Chemical compounds |
AU2001288067A1 (en) * | 2000-09-21 | 2002-04-02 | Sankyo Company Limited | Phenylpropionic acid derivatives |
EP1695716A2 (de) * | 2000-12-26 | 2006-08-30 | Sankyo Company, Limited | Medizinische Zusammensetzungen enthaltend ein Diuretikum und einen Insulin-Sensibilisator |
US20040077689A1 (en) * | 2001-04-25 | 2004-04-22 | Yasuo Sugiyama | Abc expression promoters |
WO2003002508A1 (en) * | 2001-06-28 | 2003-01-09 | Dr. Reddy's Research Foundation | Derivatives of para-ethoxy-phenillactic acid |
US20030171377A1 (en) * | 2001-08-29 | 2003-09-11 | Bigge Christopher Franklin | Antidiabetic agents |
US6716842B2 (en) | 2002-04-05 | 2004-04-06 | Warner-Lambert Company, Llc | Antidiabetic agents |
CN1787989A (zh) * | 2003-03-13 | 2006-06-14 | 小野药品工业株式会社 | 亚氨醚衍生化合物和含有该化合物作为活性成分的药物 |
US7342039B2 (en) | 2003-09-25 | 2008-03-11 | Wyeth | Substituted indole oximes |
US7420083B2 (en) | 2003-09-25 | 2008-09-02 | Wyeth | Substituted aryloximes |
AU2009335924B2 (en) * | 2008-12-18 | 2012-11-08 | Novartis Ag | Hemifumarate salt of 1- [4- [1- ( 4 -cyclohexyl-3 -trifluoromethyl-benzyloxyimino ) -ethyl] -2 -ethyl-benzyl] -a zetidine-3-carboxylic acid |
EP2752660B1 (de) | 2013-01-07 | 2016-08-31 | Nxp B.V. | Integrierte Schaltung enthaltend einen CO2 Sensor und Herstellungsverfahren |
CN110590599B (zh) * | 2019-09-30 | 2022-07-26 | 大连民族大学 | 一种群体感应信号分子结构类似物及其制备方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3872113A (en) * | 1972-05-30 | 1975-03-18 | Endo Lab | Hydroxy- and acetoxy-phthalaldehydric acid, O-(substituted) oximes |
JPS5522636A (en) * | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
JPS6051189A (ja) * | 1983-08-30 | 1985-03-22 | Sankyo Co Ltd | チアゾリジン誘導体およびその製造法 |
HU210339B (en) * | 1985-05-21 | 1995-03-28 | Pfizer | Process for preparing thiazolidinediones and their pharmaceutical compositions haring hypoglycemic effect |
EP0306228B1 (de) * | 1987-09-04 | 1999-11-17 | Beecham Group Plc | Substituierte Thiazolidindionderivate |
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 |
CA2090283A1 (en) * | 1992-02-28 | 1993-08-29 | Nobuyuki Hamanaka | Phenoxyacetic acid derivatives |
IL105191A (en) * | 1992-04-04 | 1998-08-16 | Basf Ag | Acids and aminooxymethylbenzoic acids and their preparation |
GB9311661D0 (en) * | 1993-06-05 | 1993-07-21 | Smithkline Beecham Plc | Novel compounds |
GB9311644D0 (en) * | 1993-06-05 | 1993-07-21 | Smithkline Beecham Plc | Novel compounds |
GB9315148D0 (en) * | 1993-07-22 | 1993-09-08 | Smithkline Beecham Plc | Novel compounds |
WO1996004261A1 (en) * | 1994-07-29 | 1996-02-15 | Smithkline Beecham Plc | Benzoxazoles and pryridine derivatives useful in the treatment of the type ii diabetes |
JP2843281B2 (ja) * | 1994-10-07 | 1999-01-06 | 三共株式会社 | オキシム誘導体 |
CA2159938A1 (en) * | 1994-10-07 | 1996-04-08 | Hiroaki Yanagisawa | Oxime derivatives, their preparation and their therapeutic use |
AU5701896A (en) * | 1995-06-02 | 1996-12-18 | Sankyo Company Limited | Aromatic oxyimino derivatives |
US5863946A (en) * | 1996-06-06 | 1999-01-26 | Abbott Laboratories | Iminoxyderivatives of fenamates as inhibitors of prostaglandin biosynthesis |
-
1997
- 1997-04-01 DK DK97908566T patent/DK0916651T3/da active
- 1997-04-01 PT PT97908566T patent/PT916651E/pt unknown
- 1997-04-01 DE DE69725585T patent/DE69725585T2/de not_active Expired - Fee Related
- 1997-04-01 WO PCT/JP1997/001122 patent/WO1997037970A1/ja not_active Application Discontinuation
- 1997-04-01 ES ES97908566T patent/ES2207719T3/es not_active Expired - Lifetime
- 1997-04-01 EP EP97908566A patent/EP0916651B1/de not_active Expired - Lifetime
- 1997-04-01 AU AU20446/97A patent/AU708919B2/en not_active Ceased
- 1997-04-01 CN CN97194978A patent/CN1104413C/zh not_active Expired - Fee Related
- 1997-04-01 RU RU98119843/04A patent/RU2169141C2/ru not_active IP Right Cessation
- 1997-04-01 CA CA002251468A patent/CA2251468A1/en not_active Abandoned
- 1997-04-01 NZ NZ332136A patent/NZ332136A/xx unknown
- 1997-04-01 AT AT97908566T patent/ATE252074T1/de not_active IP Right Cessation
- 1997-04-01 KR KR1019980707911A patent/KR20000005224A/ko not_active Application Discontinuation
- 1997-04-01 CZ CZ983180A patent/CZ318098A3/cs unknown
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1998
- 1998-10-02 NO NO19984633A patent/NO312664B1/no not_active IP Right Cessation
- 1998-10-05 US US09/168,973 patent/US6103907A/en not_active Expired - Fee Related
-
1999
- 1999-11-09 HK HK99105129A patent/HK1020716A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CZ318098A3 (cs) | 1999-01-13 |
ES2207719T3 (es) | 2004-06-01 |
AU708919B2 (en) | 1999-08-19 |
DE69725585D1 (de) | 2003-11-20 |
EP0916651A4 (de) | 2001-09-12 |
US6103907A (en) | 2000-08-15 |
DE69725585T2 (de) | 2004-07-01 |
EP0916651A1 (de) | 1999-05-19 |
ATE252074T1 (de) | 2003-11-15 |
AU2044697A (en) | 1997-10-29 |
CN1104413C (zh) | 2003-04-02 |
DK0916651T3 (da) | 2003-12-01 |
NZ332136A (en) | 1999-08-30 |
RU2169141C2 (ru) | 2001-06-20 |
PT916651E (pt) | 2004-01-30 |
CA2251468A1 (en) | 1997-10-16 |
CN1219927A (zh) | 1999-06-16 |
NO984633L (no) | 1998-12-03 |
HK1020716A1 (en) | 2000-05-19 |
KR20000005224A (ko) | 2000-01-25 |
WO1997037970A1 (fr) | 1997-10-16 |
EP0916651B1 (de) | 2003-10-15 |
NO984633D0 (no) | 1998-10-02 |
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