CA1236480A - Derives de n-naphthoylglycine - Google Patents

Derives de n-naphthoylglycine

Info

Publication number: CA1236480A
Authority: CA; Canada
Prior art keywords: methyl; prepared; naphthalenyl; hydrogen; bromo
Prior art date: 1981-03-02
Legal status (The legal status 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 status listed.): Expired

Application number

CA 509682

Other languages

English (en)

Other versions

CA1236480B (fr

Inventor

Kazimir Sestanj

Nedumparambil A. Abraham

Francesco Bellini

Adi Treasurywala

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Canada Inc

Original Assignee

Ayerst Mckenna and Harrison Inc

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.)

1981-03-02

Filing date

1986-05-21

Publication date

1988-05-10

Publication of CA1236480B publication Critical patent/CA1236480B/fr

1981-03-02 Priority claimed from CA000372119A external-priority patent/CA1176269A/fr

1986-05-21 Application filed by Ayerst Mckenna and Harrison Inc filed Critical Ayerst Mckenna and Harrison Inc

1986-05-21 Priority to CA 509682 priority Critical patent/CA1236480A/fr

1988-05-10 Application granted granted Critical

1988-05-10 Publication of CA1236480A publication Critical patent/CA1236480A/fr

Status Expired legal-status Critical Current

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 description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 149
150000001875 compounds Chemical class 0.000 claims abstract description 119
239000001257 hydrogen Substances 0.000 claims abstract description 100
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 80
125000000217 alkyl group Chemical group 0.000 claims abstract description 77
-1 phenylmethoxy Chemical group 0.000 claims abstract description 69
125000003545 alkoxy group Chemical group 0.000 claims abstract description 56
150000003839 salts Chemical class 0.000 claims abstract description 38
125000001424 substituent group Chemical group 0.000 claims abstract description 36
150000007530 organic bases Chemical class 0.000 claims abstract description 25
150000007529 inorganic bases Chemical class 0.000 claims abstract description 24
125000001624 naphthyl group Chemical group 0.000 claims abstract description 23
125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 14
125000001475 halogen functional group Chemical group 0.000 claims abstract description 14
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims abstract 3
238000000034 method Methods 0.000 claims description 189
230000008569 process Effects 0.000 claims description 166
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 107
239000000126 substance Substances 0.000 claims description 83
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 27
125000005843 halogen group Chemical group 0.000 claims description 15
150000002431 hydrogen Chemical group 0.000 claims description 14
239000004471 Glycine Substances 0.000 claims description 13
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
230000003301 hydrolyzing effect Effects 0.000 claims description 11
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
230000008878 coupling Effects 0.000 claims description 8
238000010168 coupling process Methods 0.000 claims description 8
238000005859 coupling reaction Methods 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 6
235000001014 amino acid Nutrition 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
SZFXXNVLSUTKJF-UHFFFAOYSA-N 5-bromonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1Br SZFXXNVLSUTKJF-UHFFFAOYSA-N 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 2
UFLJUGQVVIMHOI-UHFFFAOYSA-N 2-[(3-chloro-4-methoxynaphthalene-1-carbothioyl)amino]acetic acid Chemical compound C1=CC=C2C(OC)=C(Cl)C=C(C(=S)NCC(O)=O)C2=C1 UFLJUGQVVIMHOI-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 13
VXGABWCSZZWXPC-UHFFFAOYSA-N methyl 2-(methylamino)acetate Chemical compound CNCC(=O)OC VXGABWCSZZWXPC-UHFFFAOYSA-N 0.000 claims 8
230000001131 transforming effect Effects 0.000 claims 6
JUGVMIJTJOFVTO-UHFFFAOYSA-N methyl 2-[(5-bromonaphthalene-1-carbonyl)-methylamino]acetate Chemical compound C1=CC=C2C(C(=O)N(C)CC(=O)OC)=CC=CC2=C1Br JUGVMIJTJOFVTO-UHFFFAOYSA-N 0.000 claims 3
DYRYAMQPAPSZGA-UHFFFAOYSA-N methyl 2-[[6-methoxy-5-(trifluoromethyl)naphthalene-1-carbonyl]-methylamino]acetate Chemical compound COC1=CC=C2C(C(=O)N(C)CC(=O)OC)=CC=CC2=C1C(F)(F)F DYRYAMQPAPSZGA-UHFFFAOYSA-N 0.000 claims 3
HSXKMTOSXMWUAO-UHFFFAOYSA-N 2-[(5-bromonaphthalene-1-carbonyl)-methylamino]acetic acid Chemical compound C1=CC=C2C(C(=O)N(CC(O)=O)C)=CC=CC2=C1Br HSXKMTOSXMWUAO-UHFFFAOYSA-N 0.000 claims 2
AEBBCDMWPOXGSG-UHFFFAOYSA-N 6-methoxy-5-(trifluoromethyl)naphthalene-1-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 AEBBCDMWPOXGSG-UHFFFAOYSA-N 0.000 claims 2
BBUNLRYMKNPDTM-UHFFFAOYSA-N 2-[(3-chloro-4-methoxynaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=CC=C2C(OC)=C(Cl)C=C(C(=S)N(C)CC(O)=O)C2=C1 BBUNLRYMKNPDTM-UHFFFAOYSA-N 0.000 claims 1
OJRHDUKBQWYDLU-UHFFFAOYSA-N 2-[(4-bromonaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=C(Br)C2=C1 OJRHDUKBQWYDLU-UHFFFAOYSA-N 0.000 claims 1
BSPRKJYBOFVWPB-UHFFFAOYSA-N 2-[(4-chloronaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=C(Cl)C2=C1 BSPRKJYBOFVWPB-UHFFFAOYSA-N 0.000 claims 1
JSMQVEFYTPIXHS-UHFFFAOYSA-N 2-[(4-cyanonaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=C(C#N)C2=C1 JSMQVEFYTPIXHS-UHFFFAOYSA-N 0.000 claims 1
FTGNYRNRSMBRER-UHFFFAOYSA-N 2-[(5,7-dichloronaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=C(Cl)C=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1Cl FTGNYRNRSMBRER-UHFFFAOYSA-N 0.000 claims 1
AJYGQONVJYEETE-UHFFFAOYSA-N 2-[(5-bromo-6-methoxynaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(Br)C(OC)=CC=C21 AJYGQONVJYEETE-UHFFFAOYSA-N 0.000 claims 1
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
OQJIHWFYAGNSSR-UHFFFAOYSA-N 2-[(5-bromo-6-pentoxynaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(Br)C(OCCCCC)=CC=C21 OQJIHWFYAGNSSR-UHFFFAOYSA-N 0.000 claims 1
LBTALXDGPCIKIU-UHFFFAOYSA-N 2-[(5-bromonaphthalene-1-carbothioyl)-butylamino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)CCCC)=CC=CC2=C1Br LBTALXDGPCIKIU-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
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
DRRAAOPPYGRFDT-UHFFFAOYSA-N 2-[(5-iodo-6-methoxynaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(I)C(OC)=CC=C21 DRRAAOPPYGRFDT-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
BWMGIZVPHBVDKM-UHFFFAOYSA-N 2-[(8-bromonaphthalene-1-carbothioyl)-methylamino]acetic acid Chemical compound C1=CC(Br)=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1 BWMGIZVPHBVDKM-UHFFFAOYSA-N 0.000 claims 1
WCJXCOGMMSYTDD-UHFFFAOYSA-N 2-[[5-bromo-6-[[3-(trifluoromethyl)phenyl]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=CC(C(F)(F)F)=C1 WCJXCOGMMSYTDD-UHFFFAOYSA-N 0.000 claims 1
DOYFHMNOYUOORG-UHFFFAOYSA-N 2-[[6-methoxy-5-(trifluoromethyl)naphthalene-1-carbonyl]-methylamino]acetic acid Chemical compound OC(=O)CN(C)C(=O)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 DOYFHMNOYUOORG-UHFFFAOYSA-N 0.000 claims 1
WBZXNEAUUURWCZ-UHFFFAOYSA-N 2-[methyl(naphthalene-1-carbothioyl)amino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1 WBZXNEAUUURWCZ-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
PSPWPRIBEDWCPV-UHFFFAOYSA-N 2-[methyl-(5-nitronaphthalene-1-carbothioyl)amino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1[N+]([O-])=O PSPWPRIBEDWCPV-UHFFFAOYSA-N 0.000 claims 1
BZTAYPUOAQZQAI-UHFFFAOYSA-N 2-[methyl-(5-prop-1-en-2-ylnaphthalene-1-carbothioyl)amino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1C(C)=C BZTAYPUOAQZQAI-UHFFFAOYSA-N 0.000 claims 1
HLVACIMHQSIILJ-UHFFFAOYSA-N 2-[methyl-[5-(trifluoromethyl)naphthalene-1-carbothioyl]amino]acetic acid Chemical compound C1=CC=C2C(C(=S)N(CC(O)=O)C)=CC=CC2=C1C(F)(F)F HLVACIMHQSIILJ-UHFFFAOYSA-N 0.000 claims 1
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
AAVGEIOPRGTZFF-UHFFFAOYSA-N methyl 2-[(3-chloro-4-methoxynaphthalene-1-carbothioyl)-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC(=C(C2=CC=CC=C12)OC)Cl)=O AAVGEIOPRGTZFF-UHFFFAOYSA-N 0.000 claims 1
AOOOOTAEMRBESC-UHFFFAOYSA-N methyl 2-[(4-bromonaphthalene-1-carbothioyl)-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC=C(C2=CC=CC=C12)Br)=O AOOOOTAEMRBESC-UHFFFAOYSA-N 0.000 claims 1
BMIRDGWZCACZAI-UHFFFAOYSA-N methyl 2-[(4-chloronaphthalene-1-carbothioyl)-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC=C(C2=CC=CC=C12)Cl)=O BMIRDGWZCACZAI-UHFFFAOYSA-N 0.000 claims 1
WLOMUGCGQKNCOP-UHFFFAOYSA-N methyl 2-[(4-cyanonaphthalene-1-carbothioyl)-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC=C(C2=CC=CC=C12)C#N)=O WLOMUGCGQKNCOP-UHFFFAOYSA-N 0.000 claims 1
DSORHXCHHCPZBH-UHFFFAOYSA-N methyl 2-[(5-bromo-6-methylnaphthalene-1-carbothioyl)-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC=CC2=C(C(=CC=C12)C)Br)=O DSORHXCHHCPZBH-UHFFFAOYSA-N 0.000 claims 1
BYBCGCQVRVNLFN-UHFFFAOYSA-N methyl 2-[(5-bromonaphthalene-1-carbothioyl)-butylamino]acetate Chemical compound COC(CN(CCCC)C(=S)C1=CC=CC2=C(C=CC=C12)Br)=O BYBCGCQVRVNLFN-UHFFFAOYSA-N 0.000 claims 1
NBQXIIDQWGMYPR-UHFFFAOYSA-N methyl 2-[(5-chloronaphthalene-1-carbothioyl)-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC=CC2=C(C=CC=C12)Cl)=O NBQXIIDQWGMYPR-UHFFFAOYSA-N 0.000 claims 1
ITYDUNYCEIACEK-UHFFFAOYSA-N methyl 2-[(5-iodo-6-methoxynaphthalene-1-carbothioyl)-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC=CC2=C(C(=CC=C12)OC)I)=O ITYDUNYCEIACEK-UHFFFAOYSA-N 0.000 claims 1
WIQOVPJDVHDHEQ-UHFFFAOYSA-N methyl 2-[(5-methoxynaphthalene-1-carbothioyl)-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC=CC2=C(C=CC=C12)OC)=O WIQOVPJDVHDHEQ-UHFFFAOYSA-N 0.000 claims 1
LYXUSLNTFAVDRT-UHFFFAOYSA-N methyl 2-[[5-bromo-6-[(4-chlorophenyl)methoxy]naphthalene-1-carbothioyl]-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC=CC2=C(C(=CC=C12)OCC1=CC=C(C=C1)Cl)Br)=O LYXUSLNTFAVDRT-UHFFFAOYSA-N 0.000 claims 1
WCTDKYSLUOYBQW-UHFFFAOYSA-N methyl 2-[[6-methoxy-5-(trifluoromethyl)naphthalene-1-carbothioyl]-methylamino]acetate Chemical compound COC(CN(C)C(=S)C1=CC=CC2=C(C(=CC=C12)OC)C(F)(F)F)=O WCTDKYSLUOYBQW-UHFFFAOYSA-N 0.000 claims 1
WMKTXTLKWPLSIZ-UHFFFAOYSA-N methyl 2-[methyl(naphthalene-1-carbothioyl)amino]acetate Chemical compound C1=CC=C2C(C(=S)N(C)CC(=O)OC)=CC=CC2=C1 WMKTXTLKWPLSIZ-UHFFFAOYSA-N 0.000 claims 1
239000011780 sodium chloride Substances 0.000 claims 1
LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 claims 1
206010012601 diabetes mellitus Diseases 0.000 abstract description 12
238000002360 preparation method Methods 0.000 abstract description 11
230000009286 beneficial effect Effects 0.000 abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
229910052757 nitrogen Inorganic materials 0.000 description 49
239000000203 mixture Substances 0.000 description 41
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
125000001246 bromo group Chemical group Br* 0.000 description 30
239000007858 starting material Substances 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
239000000047 product Substances 0.000 description 23
239000002253 acid Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
125000001309 chloro group Chemical group Cl* 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
125000004432 carbon atom Chemical group C* 0.000 description 13
235000019441 ethanol Nutrition 0.000 description 12
230000007062 hydrolysis Effects 0.000 description 12
238000006460 hydrolysis reaction Methods 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
230000002378 acidificating effect Effects 0.000 description 11
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CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 1
108010065338 N-ethylglycine Proteins 0.000 description 1
PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
102000004316 Oxidoreductases Human genes 0.000 description 1
108090000854 Oxidoreductases Proteins 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000350158 Prioria balsamifera Species 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241001061127 Thione Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960001466 acetohexamide Drugs 0.000 description 1
VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000003288 aldose reductase inhibitor Substances 0.000 description 1
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
210000005252 bulbus oculi Anatomy 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
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SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
229960001761 chlorpropamide Drugs 0.000 description 1
238000011210 chromatographic step Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000003467 diminishing effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
OJFGRDHUZSJJPB-UHFFFAOYSA-N ethyl 2-(butylamino)acetate Chemical compound CCCCNCC(=O)OCC OJFGRDHUZSJJPB-UHFFFAOYSA-N 0.000 description 1
JJUSZJBGNONFQT-UHFFFAOYSA-N ethyl 2-(propylamino)acetate Chemical compound CCCNCC(=O)OCC JJUSZJBGNONFQT-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
150000002402 hexoses Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
NYEHYTMDKFXJEE-UHFFFAOYSA-N methyl 2-(ethylamino)acetate Chemical compound CCNCC(=O)OC NYEHYTMDKFXJEE-UHFFFAOYSA-N 0.000 description 1
NXDPEGBGHJHNSR-UHFFFAOYSA-N methyl 2-(prop-2-enylamino)acetate Chemical compound COC(=O)CNCC=C NXDPEGBGHJHNSR-UHFFFAOYSA-N 0.000 description 1
WGRRPSIMTIFJCJ-UHFFFAOYSA-N methyl 5-cyano-6-methoxynaphthalene-1-carboxylate Chemical compound COC1=CC=C2C(C(=O)OC)=CC=CC2=C1C#N WGRRPSIMTIFJCJ-UHFFFAOYSA-N 0.000 description 1
OVJOQRHZXHGGSK-UHFFFAOYSA-N methyl 5-iodo-6-methoxynaphthalene-1-carboxylate Chemical compound COC1=CC=C2C(C(=O)OC)=CC=CC2=C1I OVJOQRHZXHGGSK-UHFFFAOYSA-N 0.000 description 1
OIEDIIUKHOBNIG-UHFFFAOYSA-N methyl 6-methoxynaphthalene-1-carboxylate Chemical compound COC1=CC=C2C(C(=O)OC)=CC=CC2=C1 OIEDIIUKHOBNIG-UHFFFAOYSA-N 0.000 description 1
HMRROBKAACRWBP-UHFFFAOYSA-N methyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=CC2=C1 HMRROBKAACRWBP-UHFFFAOYSA-N 0.000 description 1
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 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
NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000003921 oil 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
230000037361 pathway Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 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
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000009877 rendering Methods 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical group N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010288 sodium nitrite 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
238000006467 substitution reaction Methods 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
229940124597 therapeutic agent 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

Classifications

- 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
- 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
- C07C63/33—Polycyclic acids
- C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
- C07C63/34—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings
- C07C63/36—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings containing one carboxyl group
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA 509682 1981-03-02 1986-05-21 Derives de n-naphthoylglycine Expired CA1236480A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 509682 CA1236480A (fr)	1981-03-02	1986-05-21	Derives de n-naphthoylglycine

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA000372119A CA1176269A (fr)	1981-03-02	1981-03-02	Derives de n-naphtoylglycine
CA 509682 CA1236480A (fr)	1981-03-02	1986-05-21	Derives de n-naphthoylglycine

Publications (2)

Publication Number	Publication Date
CA1236480B CA1236480B (fr)
CA1236480A true CA1236480A (fr)	1988-05-10

Family

ID=25669268

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 509682 Expired CA1236480A (fr)	1981-03-02	1986-05-21	Derives de n-naphthoylglycine

Country Status (1)

Country	Link
CA (1)	CA1236480A (fr)

1986
- 1986-05-21 CA CA 509682 patent/CA1236480A/fr not_active Expired

Also Published As

Publication number	Publication date
CA1236480B (fr)

Legal Events

Date	Code	Title	Description
1988-05-10	NARE	Reissued
2001-10-16	MKEX	Expiry

Publication	Publication Date	Title
CA1176269A (fr)	1984-10-16	Derives de n-naphtoylglycine
JPH0415221B2 (fr)	1992-03-17
EP0026928B1 (fr)	1984-01-25	Composés d'acide 3,4-diarylisoxazole-5-acétique, procédé de préparation et médicaments les contenant
EP0059596B1 (fr)	1985-04-24	Dérivés de N-naphtoylglycine
CA1191156A (fr)	1985-07-30	N-((6-(alcoxy inferieur)-5-(trifluoromethylthio)-1- naphtalenyl)-thioxomethyl)-n-(alcoyle interieur) glycines
US4391816A (en)	1983-07-05	N-(Naphthalenylthioxomethyl)aminoacid derivatives
FR2472574A1 (fr)	1981-07-03	Derives de cephalosporine et composition pharmaceutique les contenant
US4447452A (en)	1984-05-08	N[(2-Naphthalenyl)thioxomethyl]glycine derivatives
EP0182499B1 (fr)	1989-04-12	N-(6-Méthoxy-5(perfluoroalcoyl)-1-naphtoyl)-N-méthylglycines et N-(6-méthoxy-5-(perfluoroalcoyl)-1-thionaphthoyl)-N-méthylglycines
CA1236480A (fr)	1988-05-10	Derives de n-naphthoylglycine
CA1307537C (fr)	1992-09-15	N-naphtoylglycines utilises comme inhibiteurs de l'aldose reductase
JPH02215750A (ja)	1990-08-28	２，６−ジクロロフェニルアミノベンゼン酢酸誘導体及びジフェニルアミン誘導体の製造方法。
US5047553A (en)	1991-09-10	Tetrafluoro-N-phenylphthalimide
US4116972A (en)	1978-09-26	Anti-inflammatory 1-oxo-isoindoline derivatives and processes for their preparation
US3849446A (en)	1974-11-19	Chromone-3-carboxylic acids
CA1188318A (fr)	1985-06-04	Derives de la n-(naphtoyle substitue) glycine
KR890000798B1 (ko)	1989-04-07	N-나프토일글리신 유도체의 제조방법
CA2111169C (fr)	2001-05-01	Derives de l'acide phenylacetique, procede pour leur preparation et utilisation correspondante
CA1187093A (fr)	1985-05-14	Derives de n-(naphtoyl substitue)glycine
IE882015L (en)	1989-01-02	PRIDYL-PYRROLO £1,2-c\| THIAZOLES
US4342781A (en)	1982-08-03	Diphenylpropenamides as SRS-A antagonists
JPS62292771A (ja)	1987-12-19	ベンゾグアナミン誘導体の製法
FR2564467A1 (fr)	1985-11-22	Nouveaux derives de thieno (2,3-b) pyrrole, leur procede de preparation et les compositions pharmaceutiques les renfermant
JPH07206816A (ja)	1995-08-08	２，４，５−トリブロモピロール−３−カルボニトリルの調製方法
JPS5965072A (ja)	1984-04-13	インドリンまたはインドリン誘導体の製造方法