IE52604B1 - N-naphthoylglycine derivatives - Google Patents
N-naphthoylglycine derivativesInfo
- Publication number
- IE52604B1 IE52604B1 IE448/82A IE44882A IE52604B1 IE 52604 B1 IE52604 B1 IE 52604B1 IE 448/82 A IE448/82 A IE 448/82A IE 44882 A IE44882 A IE 44882A IE 52604 B1 IE52604 B1 IE 52604B1
- Authority
- IE
- Ireland
- Prior art keywords
- naphthalenyl
- hydrogen
- thioxomethyl
- alkoxy
- halo
- Prior art date
Links
- YQHPVWRRSORYIV-UHFFFAOYSA-N 2-(naphthalene-1-carbonylamino)acetic acid Chemical class C1=CC=C2C(C(=O)NCC(=O)O)=CC=CC2=C1 YQHPVWRRSORYIV-UHFFFAOYSA-N 0.000 title abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 134
- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 239000001257 hydrogen Substances 0.000 claims abstract description 67
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 60
- 125000001424 substituent group Chemical group 0.000 claims abstract description 48
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 235000001014 amino acid Nutrition 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 208000002249 Diabetes Complications Diseases 0.000 claims abstract description 5
- 206010012655 Diabetic complications Diseases 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 78
- -1 phenylmethoxy Chemical group 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 37
- 125000001624 naphthyl group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 150000007530 organic bases Chemical class 0.000 claims description 21
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 20
- 125000001475 halogen functional group Chemical group 0.000 claims description 20
- 150000007529 inorganic bases Chemical class 0.000 claims description 19
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 17
- 150000004702 methyl esters Chemical class 0.000 claims description 15
- 206010012601 diabetes mellitus Diseases 0.000 claims description 12
- 239000004471 Glycine Substances 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 108010077895 Sarcosine Proteins 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 2
- CUJUSUACDQSBGH-UHFFFAOYSA-N 2-[(5-bromo-6-methylnaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound CC1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1Br CUJUSUACDQSBGH-UHFFFAOYSA-N 0.000 claims 1
- LGQAAIIPVUITAM-UHFFFAOYSA-N 2-[(5-bromonaphthalene-1-carbothioyl)-ethylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)CC)=CC=CC2=C1Br LGQAAIIPVUITAM-UHFFFAOYSA-N 0.000 claims 1
- GFPLMVUVCPPPGZ-UHFFFAOYSA-N 2-[(5-bromonaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1Br GFPLMVUVCPPPGZ-UHFFFAOYSA-N 0.000 claims 1
- HUTXULJFQZRFHV-UHFFFAOYSA-N 2-[(5-bromonaphthalene-1-carbothioyl)-prop-2-enylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC=C)CC(=O)O)=CC=CC2=C1Br HUTXULJFQZRFHV-UHFFFAOYSA-N 0.000 claims 1
- WDXAHGSNENIIED-UHFFFAOYSA-N 2-[(5-bromonaphthalene-1-carbothioyl)-propylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)CCC)=CC=CC2=C1Br WDXAHGSNENIIED-UHFFFAOYSA-N 0.000 claims 1
- SPKBKCPMUKPXCG-UHFFFAOYSA-N 2-[(5-chloronaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1Cl SPKBKCPMUKPXCG-UHFFFAOYSA-N 0.000 claims 1
- UBGSLWTYHJPKHC-UHFFFAOYSA-N 2-[(5-cyano-6-methoxynaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C#N)C(OC)=CC=C21 UBGSLWTYHJPKHC-UHFFFAOYSA-N 0.000 claims 1
- PHTRWSQIGOHXGM-UHFFFAOYSA-N 2-[(5-cyanonaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1C#N PHTRWSQIGOHXGM-UHFFFAOYSA-N 0.000 claims 1
- FUYBNIRQVNHGJW-UHFFFAOYSA-N 2-[(5-methoxynaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=CC=C2C(OC)=CC=CC2=C1C(=S)N(C)CC(O)=O FUYBNIRQVNHGJW-UHFFFAOYSA-N 0.000 claims 1
- GPTKIDXXEHEYDT-UHFFFAOYSA-N 2-[[5-bromo-6-[(4-chlorophenyl)methoxy]naphthalene-1-carbothioyl]-methylamino]acetic acid Chemical compound C=1C=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C(Br)C=1OCC1=CC=C(Cl)C=C1 GPTKIDXXEHEYDT-UHFFFAOYSA-N 0.000 claims 1
- LYWLHDHGGZJMLE-UHFFFAOYSA-N 2-[benzyl-(5-bromonaphthalene-1-carbothioyl)amino]acetic acid Chemical compound C=1C=CC2=C(Br)C=CC=C2C=1C(=S)N(CC(=O)O)CC1=CC=CC=C1 LYWLHDHGGZJMLE-UHFFFAOYSA-N 0.000 claims 1
- FVGSDTNULHCJFW-UHFFFAOYSA-N 2-[methyl-(5-methylnaphthalene-1-carbothioyl)amino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1C FVGSDTNULHCJFW-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 claims 1
- 230000002829 reductive effect Effects 0.000 abstract description 11
- 102000016912 Aldehyde Reductase Human genes 0.000 abstract description 10
- 108010053754 Aldehyde reductase Proteins 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 10
- 230000002401 inhibitory effect Effects 0.000 abstract description 7
- 150000001413 amino acids Chemical class 0.000 abstract description 4
- 150000001323 aldoses Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 101
- 229910052757 nitrogen Inorganic materials 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 54
- 239000000243 solution Substances 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 47
- 239000002253 acid Substances 0.000 description 37
- 125000001246 bromo group Chemical group Br* 0.000 description 32
- 239000007858 starting material Substances 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- 239000002244 precipitate Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
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- 238000001914 filtration Methods 0.000 description 11
- 101150041968 CDC13 gene Proteins 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 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
- 238000010992 reflux Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- 241000700159 Rattus Species 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 239000003538 oral antidiabetic agent Substances 0.000 description 6
- 229940127209 oral hypoglycaemic agent Drugs 0.000 description 6
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- 108090001061 Insulin Proteins 0.000 description 5
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
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- 238000002474 experimental method Methods 0.000 description 4
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- RRGQQPVJOQHXNH-UHFFFAOYSA-N methyl 2-[(5-bromonaphthalene-1-carbothioyl)-methylamino]acetate Chemical compound C1=CC=C2C(C(=S)N(C)CC(=O)OC)=CC=CC2=C1Br RRGQQPVJOQHXNH-UHFFFAOYSA-N 0.000 description 1
- SAXDVSSZYMCODG-UHFFFAOYSA-N methyl 2-[(6-methoxynaphthalene-1-carbonyl)-methylamino]acetate Chemical compound COC1=CC=C2C(C(=O)N(C)CC(=O)OC)=CC=CC2=C1 SAXDVSSZYMCODG-UHFFFAOYSA-N 0.000 description 1
- SAJFEUIFWFKNDL-UHFFFAOYSA-N methyl 2-[[6-methoxy-5-(trifluoromethylsulfanyl)naphthalene-1-carbonyl]-methylamino]acetate Chemical compound COC1=CC=C2C(C(=O)N(C)CC(=O)OC)=CC=CC2=C1SC(F)(F)F SAJFEUIFWFKNDL-UHFFFAOYSA-N 0.000 description 1
- RKWJGQUAYXKOGJ-UHFFFAOYSA-N methyl 4,6-dimethoxynaphthalene-1-carboxylate Chemical compound COC1=CC=C2C(C(=O)OC)=CC=C(OC)C2=C1 RKWJGQUAYXKOGJ-UHFFFAOYSA-N 0.000 description 1
- ZLIJOOSYZMSWAR-UHFFFAOYSA-N methyl 5-(trifluoromethyl)naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=CC2=C1C(F)(F)F ZLIJOOSYZMSWAR-UHFFFAOYSA-N 0.000 description 1
- AJSVNRJVTNNXCZ-UHFFFAOYSA-N methyl 5-bromo-6-methoxynaphthalene-1-carboxylate Chemical compound COC1=CC=C2C(C(=O)OC)=CC=CC2=C1Br AJSVNRJVTNNXCZ-UHFFFAOYSA-N 0.000 description 1
- HUYXJYQARDDMNH-UHFFFAOYSA-N methyl 5-iodonaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=CC2=C1I HUYXJYQARDDMNH-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002997 ophthalmic solution Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 229960003243 phenformin Drugs 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- LXANPKRCLVQAOG-NSHDSACASA-N sorbinil Chemical compound C12=CC(F)=CC=C2OCC[C@@]21NC(=O)NC2=O LXANPKRCLVQAOG-NSHDSACASA-N 0.000 description 1
- 229950004311 sorbinil Drugs 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SDVHRXOTTYYKRY-UHFFFAOYSA-J tetrasodium;dioxido-oxo-phosphonato-$l^{5}-phosphane Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)P([O-])([O-])=O SDVHRXOTTYYKRY-UHFFFAOYSA-J 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000001391 thioamide group Chemical group 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
- 229960002277 tolazamide Drugs 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/72—Polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Seasonings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000372119A CA1176269A (en) | 1981-03-02 | 1981-03-02 | N-naphthoylglycine derivatives |
| CA000387991A CA1191156A (en) | 1981-10-15 | 1981-10-15 | N-((6-(lower alkoxy)-5-(trifluoromethylthio)-1- naphthalenyl)-thioxomethyl)-n-(lower alkyl)glycines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE820448L IE820448L (en) | 1982-09-02 |
| IE52604B1 true IE52604B1 (en) | 1987-12-23 |
Family
ID=25669267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE448/82A IE52604B1 (en) | 1981-03-02 | 1982-03-01 | N-naphthoylglycine derivatives |
Country Status (18)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4446150A (en) * | 1982-09-21 | 1984-05-01 | Ayerst, Mckenna & Harrison, Inc. | Naphthalenylthiazole derivatives |
| FR2549474B1 (fr) * | 1983-07-19 | 1987-09-11 | Elf Aquitaine | Nouveaux thioamides, leurs preparation et applications |
| US4492706A (en) * | 1983-08-01 | 1985-01-08 | American Home Products Corporation | Method of lowering lipid levels |
| US4604406A (en) * | 1984-11-16 | 1986-08-05 | Ayerst, Mckenna & Harrison, Inc. | N-[6-methoxy-5-(perfluoroalkyl)-1-naphtholyl]-N-methylglycines and their thionaphthoyl analogs |
| US4663452A (en) * | 1985-08-29 | 1987-05-05 | Ethyl Corporation | Thiation process |
| US4734435A (en) * | 1986-04-07 | 1988-03-29 | American Home Products Corp. | N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]-thioxomethyl]-N-methylglycine S-oxide and the amide thereof |
| JPS63119455A (ja) * | 1986-06-27 | 1988-05-24 | Nippon Shinyaku Co Ltd | グリシン誘導体 |
| CA1307537C (en) * | 1987-12-23 | 1992-09-15 | Jay E. Wrobel | N-naphthoylglycines as aldose reductase inhibitors |
| US4820727A (en) * | 1987-12-23 | 1989-04-11 | American Home Products Corporation | N-acyl-N-naphthoylglycines as aldose reductase inhibitors |
| DE4318069C1 (de) * | 1993-06-01 | 1994-03-31 | Cassella Ag | Verfahren zur Herstellung von 5-Brom-6-methoxy-1-naphthoesäuremethylester |
| DE19603329A1 (de) | 1996-01-31 | 1997-08-07 | Bayer Ag | Verfahren zur Herstellung von aromatischen Methoxycarbonsäuremethylestern |
| WO1998042324A2 (en) * | 1997-03-21 | 1998-10-01 | The Regents Of The University Of California | Methods for modulating neurotrophic factor-associated activity using aldose reductase inhibitors |
| US6696407B1 (en) | 1997-03-21 | 2004-02-24 | The Regents Of The University Of California | Huntington's disease treatment comprising administering aldose reductase inhibitors to increase striatal CNTF |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3821383A (en) * | 1972-07-10 | 1974-06-28 | Ayerst Mckenna & Harrison | Compositions for and a method of treating diabetic complications |
-
1982
- 1982-02-10 AU AU80342/82A patent/AU544067B2/en not_active Expired
- 1982-02-24 CY CY138582A patent/CY1385A/xx unknown
- 1982-02-24 EP EP82300940A patent/EP0059596B1/en not_active Expired
- 1982-02-24 DE DE8282300940T patent/DE3263225D1/de not_active Expired
- 1982-02-24 AT AT82300940T patent/ATE12932T1/de not_active IP Right Cessation
- 1982-02-25 PH PH26913A patent/PH17378A/en unknown
- 1982-03-01 IE IE448/82A patent/IE52604B1/en not_active IP Right Cessation
- 1982-03-01 DK DK089182A patent/DK160760C/da not_active IP Right Cessation
- 1982-03-01 ES ES510004A patent/ES510004A0/es active Granted
- 1982-03-01 HU HU82615A patent/HU188778B/hu unknown
- 1982-03-02 SU SU823462357A patent/SU1241985A3/ru active
- 1982-03-02 GR GR67447A patent/GR76037B/el unknown
-
1987
- 1987-05-15 SG SG44687A patent/SG44687G/en unknown
- 1987-06-05 DO DO1987004565A patent/DOP1987004565A/es unknown
- 1987-07-07 KE KE3737A patent/KE3737A/xx unknown
- 1987-10-29 HK HK809/87A patent/HK80987A/en not_active IP Right Cessation
- 1987-12-30 MY MY627/87A patent/MY8700627A/xx unknown
-
1994
- 1994-05-16 GE GEAP19941918A patent/GEP19960617B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8307214A1 (es) | 1983-07-01 |
| EP0059596A1 (en) | 1982-09-08 |
| PH17378A (en) | 1984-08-06 |
| DK89182A (da) | 1982-09-03 |
| AU544067B2 (en) | 1985-05-16 |
| GEP19960617B (en) | 1996-12-12 |
| DE3263225D1 (de) | 1985-05-30 |
| ATE12932T1 (de) | 1985-05-15 |
| GR76037B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-08-03 |
| SU1241985A3 (ru) | 1986-06-30 |
| EP0059596B1 (en) | 1985-04-24 |
| AU8034282A (en) | 1982-09-09 |
| DK160760B (da) | 1991-04-15 |
| KE3737A (en) | 1987-09-04 |
| CY1385A (en) | 1987-12-18 |
| IE820448L (en) | 1982-09-02 |
| SG44687G (en) | 1987-07-24 |
| ES510004A0 (es) | 1983-07-01 |
| HU188778B (en) | 1986-05-28 |
| MY8700627A (en) | 1987-12-31 |
| HK80987A (en) | 1987-11-06 |
| DK160760C (da) | 1991-09-23 |
| DOP1987004565A (es) | 1997-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SPCF | Request for grant of supplementary protection certificate |
Free format text: SPC 3/93:19930129 |
|
| SPCG | Supplementary protection certificate granted |
Free format text: SPC 3/93 EXPIRES:20030207 |
|
| MK9A | Patent expired |