AU674613B2 - Quinoxaline derivative as antidiabetic agent - Google Patents
Quinoxaline derivative as antidiabetic agent Download PDFInfo
- Publication number
- AU674613B2 AU674613B2 AU76660/94A AU7666094A AU674613B2 AU 674613 B2 AU674613 B2 AU 674613B2 AU 76660/94 A AU76660/94 A AU 76660/94A AU 7666094 A AU7666094 A AU 7666094A AU 674613 B2 AU674613 B2 AU 674613B2
- Authority
- AU
- Australia
- Prior art keywords
- group
- lower alkyl
- optionally
- alkyl group
- formula
- Prior art date
- 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.)
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- 239000003472 antidiabetic agent Substances 0.000 title claims description 8
- 229940125708 antidiabetic agent Drugs 0.000 title claims description 6
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title description 459
- 125000000217 alkyl group Chemical group 0.000 claims description 1793
- -1 1,3 dioxolanyl group Chemical group 0.000 claims description 1278
- 150000003839 salts Chemical class 0.000 claims description 487
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 481
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 430
- 125000003545 alkoxy group Chemical group 0.000 claims description 383
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 281
- 125000005843 halogen group Chemical group 0.000 claims description 230
- 150000002367 halogens Chemical class 0.000 claims description 224
- 125000002252 acyl group Chemical group 0.000 claims description 199
- OSDBJMYIUDLIRI-UHFFFAOYSA-N oxo-[[1-[[4-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]cyclohexyl]oxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COC1CCC(OCN2C=CC(=C[NH+]=O)C=C2)CC1 OSDBJMYIUDLIRI-UHFFFAOYSA-N 0.000 claims description 197
- 125000001424 substituent group Chemical group 0.000 claims description 192
- 125000003277 amino group Chemical group 0.000 claims description 190
- 125000003342 alkenyl group Chemical group 0.000 claims description 132
- DTXOCJGLLMAFBX-UHFFFAOYSA-N oxo-[[1-[2-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]ethoxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCCOCN1C=CC(=C[NH+]=O)C=C1 DTXOCJGLLMAFBX-UHFFFAOYSA-N 0.000 claims description 126
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 126
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 117
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 114
- 229910052757 nitrogen Inorganic materials 0.000 claims description 90
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 89
- 125000000623 heterocyclic group Chemical group 0.000 claims description 71
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 60
- 125000004043 oxo group Chemical group O=* 0.000 claims description 59
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 58
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 54
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 53
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 49
- 125000002947 alkylene group Chemical group 0.000 claims description 44
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 23
- 125000004423 acyloxy group Chemical group 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 17
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 9
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 4
- 208000002249 Diabetes Complications Diseases 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims description 2
- 206010012655 Diabetic complications Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000003252 quinoxalines Chemical class 0.000 claims 30
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 238000003786 synthesis reaction Methods 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 3
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 3
- 239000007800 oxidant agent Substances 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- GENNPRIQHQRRPM-UHFFFAOYSA-N 3-methyl-1-oxidoquinoxalin-1-ium Chemical compound C1=CC=CC2=NC(C)=C[N+]([O-])=C21 GENNPRIQHQRRPM-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- OARGFWQSVACNCO-UHFFFAOYSA-N 1-oxidoquinoxalin-1-ium Chemical compound C1=CC=C2[N+]([O-])=CC=NC2=C1 OARGFWQSVACNCO-UHFFFAOYSA-N 0.000 claims 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical group OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- UBCSFKVPLDHSSB-UHFFFAOYSA-N 3-methyl-n-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]-4-oxidoquinoxalin-4-ium-2-carboxamide Chemical compound N=1C(CNC(=O)C=2C(=[N+]([O-])C3=CC=CC=C3N=2)C)=C(C)OC=1C1=CC=CC=C1 UBCSFKVPLDHSSB-UHFFFAOYSA-N 0.000 claims 1
- 101000837626 Homo sapiens Thyroid hormone receptor alpha Proteins 0.000 claims 1
- 102100028702 Thyroid hormone receptor alpha Human genes 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 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 claims 1
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- JUEQTBZWKTUIAN-UHFFFAOYSA-N n-[5-(1-benzofuran-2-yl)hexa-2,4-dienyl]-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxamide Chemical compound C1=CC=C2OC(C(=CC=CCNC(=O)C=3C(=[N+]([O-])C4=CC=CC=C4N=3)C)C)=CC2=C1 JUEQTBZWKTUIAN-UHFFFAOYSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 109
- 125000001589 carboacyl group Chemical group 0.000 description 41
- 150000003536 tetrazoles Chemical group 0.000 description 37
- 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 16
- 102000004877 Insulin Human genes 0.000 description 8
- 108090001061 Insulin Proteins 0.000 description 8
- 229940125396 insulin Drugs 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 101710180366 CDP-L-myo-inositol myo-inositolphosphotransferase Proteins 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000002218 hypoglycaemic effect Effects 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 125000004193 piperazinyl group Chemical group 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 3
- 125000006040 2-hexenyl group Chemical group 0.000 description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 description 3
- 125000003884 phenylalkyl group Chemical group 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 3
- VRYALKFFQXWPIH-PBXRRBTRSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-PBXRRBTRSA-N 0.000 description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 2
- ALHUXMDEZNLFTA-UHFFFAOYSA-N 2-methylquinoxaline Chemical compound C1=CC=CC2=NC(C)=CN=C21 ALHUXMDEZNLFTA-UHFFFAOYSA-N 0.000 description 2
- 125000006024 2-pentenyl group Chemical group 0.000 description 2
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
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- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000013016 Hypoglycemia Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- PMMURAAUARKVCB-UHFFFAOYSA-N alpha-D-ara-dHexp Natural products OCC1OC(O)CC(O)C1O PMMURAAUARKVCB-UHFFFAOYSA-N 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
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- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 239000007952 growth promoter Substances 0.000 description 2
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- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
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- 125000002632 imidazolidinyl group Chemical group 0.000 description 2
- 230000003914 insulin secretion Effects 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
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- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000000021 stimulant Substances 0.000 description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Endocrinology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24114093 | 1993-09-28 | ||
JP5-241140 | 1993-09-28 | ||
JP11463994 | 1994-04-28 | ||
JP6-114639 | 1994-04-28 | ||
PCT/JP1994/001559 WO1995009159A1 (en) | 1993-09-28 | 1994-09-22 | Quinoxaline derivative as antidiabetic agent |
Publications (2)
Publication Number | Publication Date |
---|---|
AU7666094A AU7666094A (en) | 1995-04-18 |
AU674613B2 true AU674613B2 (en) | 1997-01-02 |
Family
ID=26453355
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU76660/94A Ceased AU674613B2 (en) | 1993-09-28 | 1994-09-22 | Quinoxaline derivative as antidiabetic agent |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0670831A1 (ko) |
KR (1) | KR100196356B1 (ko) |
CN (1) | CN1114834A (ko) |
AU (1) | AU674613B2 (ko) |
CA (1) | CA2150345A1 (ko) |
TW (1) | TW284760B (ko) |
WO (1) | WO1995009159A1 (ko) |
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CN1088062C (zh) * | 1994-11-23 | 2002-07-24 | 纽罗根公司 | 某些4-氨基甲基-2-取代的咪唑衍生物2-氨基甲基-4-取代的咪唑衍生物新的一族多巴胺受体亚型特异性配体 |
WO1998055454A2 (en) * | 1997-06-05 | 1998-12-10 | Takeda Chemical Industries, Ltd. | Benzofurans and benzothophenes as suppressors of neurodegeneration |
US6207665B1 (en) | 1997-06-12 | 2001-03-27 | Schering Aktiengesellschaft | Piperazine derivatives and their use as anti-inflammatory agents |
ES2131020B1 (es) * | 1997-10-13 | 2000-03-01 | Lacer Sa | Derivados de benzofurano, dihidrobenzofunaro, dihidrobenzopirano y benzopirano como agentes antidepresivos. |
US6429207B1 (en) | 1997-11-21 | 2002-08-06 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases |
AP1538A (en) | 1999-01-11 | 2006-01-10 | Agouron Pharma | Tricyclic inhibitors of poly (adp-ribose) polymerases. |
ECSP003637A (es) | 1999-08-31 | 2002-03-25 | Agouron Pharma | Inhibidores triciclicos de poli (adp-ribosa) polimerasas |
US6969730B2 (en) * | 2001-03-16 | 2005-11-29 | Abbott Laboratories | Amines as histamine-3 receptor ligands and their therapeutic applications |
FR2822463B1 (fr) | 2001-03-21 | 2004-07-30 | Lipha | Derives bicycliques de guanidines et leurs applications en therapeutique |
MXPA03000966A (es) * | 2002-02-28 | 2003-09-04 | Pfizer Prod Inc | Agentes antidiabeticos. |
US7153889B2 (en) | 2002-11-12 | 2006-12-26 | Abbott Laboratories | Bicyclic-substituted amines as histamine-3 receptor ligands |
US20050148586A1 (en) * | 2004-01-06 | 2005-07-07 | Beavers Mary P. | Quinoxalinones |
PL1720836T3 (pl) | 2004-02-25 | 2014-09-30 | Lilly Co Eli | 6-podstawione 2,3,4,5-tetrahydro-1h-benzo [d]azepiny jako agoniści receptora 5-ht2c |
US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
US7145005B2 (en) | 2004-05-12 | 2006-12-05 | Abbott Laboratories | 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation |
US7205316B2 (en) | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
ATE432926T1 (de) * | 2004-07-26 | 2009-06-15 | Lilly Co Eli | Oxazolderivate als histamin-h3-rezeptor- wirkstoffe, deren herstellung und therapeutische verwendung |
EP1741708A1 (en) | 2005-06-28 | 2007-01-10 | Sanofi-Aventis Deutschland GmbH | Heteroaryl-substituted amides comprising an unsaturated or cyclic linker group, and their use as pharmaceuticals |
TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
US8492378B2 (en) | 2006-08-03 | 2013-07-23 | Takeda Pharmaceutical Company Limited | GSK-3β inhibitor |
US8183264B2 (en) | 2006-09-21 | 2012-05-22 | Eisai R&D Managment Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
CN100460397C (zh) * | 2006-11-07 | 2009-02-11 | 浙江大学 | 含硫喹喔啉二氧化物及其制备和在制备低氧选择性抗肿瘤药物中的应用 |
EP2091944B1 (en) | 2006-11-17 | 2011-05-18 | Pfizer Inc. | Substituted bicyclocarboxyamide compounds |
CN102702185A (zh) | 2007-04-27 | 2012-10-03 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物的盐的结晶 |
TW200841879A (en) | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
EP2344446A4 (en) | 2008-10-17 | 2012-04-04 | Akaal Pharma Pty Ltd | S1P RECEPTOR MODULATORS |
EP2344484B1 (en) * | 2008-10-17 | 2016-06-08 | Akaal Pharma Pty Ltd | S1p receptors modulators and use thereof |
US8188119B2 (en) | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
US8501804B2 (en) | 2008-10-27 | 2013-08-06 | Takeda Pharmaceutical Company Limited | Bicyclic compound |
EA201690153A1 (ru) | 2013-07-03 | 2016-06-30 | Кариофарм Терапевтикс, Инк. | Замещенные бензофуранильные и бензоксазолильные соединения и их применения |
CN104086491B (zh) * | 2014-07-09 | 2016-04-06 | 广西师范大学 | 2,3-二取代喹喔啉衍生物的制备方法 |
WO2017117447A1 (en) * | 2015-12-31 | 2017-07-06 | Karyopharm Therapeutics Inc. | Multicyclic compounds and uses thereof |
US20240109899A1 (en) * | 2021-02-04 | 2024-04-04 | Bristol-Myers Squibb Company | Benzofuran compounds as sting agonists |
CR20230576A (es) | 2021-06-14 | 2024-04-05 | Scorpion Therapeutics Inc | Derivados de la urea que pueden ser utilizados para tratar el cáncer |
Citations (2)
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AU9049391A (en) * | 1990-12-20 | 1992-07-22 | Warner-Lambert Company | 2-acylamido derivatives of 3,4-dihydro-3-oxo-quinoxaline having pharmaceutical activity |
AU4613293A (en) * | 1992-09-04 | 1994-03-10 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds, their production and use |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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FR3717M (fr) * | 1964-04-17 | 1965-11-29 | Rhone Poulenc Sa | Nouveaux dérivés de la quinoxaline et médicaments les contenant. |
US3819633A (en) * | 1970-04-01 | 1974-06-25 | Erba Carlo Spa | (iso)quinolyl sulfonylureas having antidiabetic activity |
IL39384A0 (en) * | 1971-05-17 | 1972-07-26 | Ciba Geigy Ag | New quinoxaline derivatives,their manufacture and pharmaceutical compositions containing them |
SE405853B (sv) * | 1972-05-01 | 1979-01-08 | Pfizer | Forfarande for framstellning av 2-kinoxalinkarboxamid-1,4-dioxider |
-
1994
- 1994-09-22 WO PCT/JP1994/001559 patent/WO1995009159A1/en not_active Application Discontinuation
- 1994-09-22 KR KR1019950702128A patent/KR100196356B1/ko not_active IP Right Cessation
- 1994-09-22 CA CA002150345A patent/CA2150345A1/en not_active Abandoned
- 1994-09-22 AU AU76660/94A patent/AU674613B2/en not_active Ceased
- 1994-09-22 EP EP94927085A patent/EP0670831A1/en not_active Withdrawn
- 1994-09-22 CN CN94190719A patent/CN1114834A/zh active Pending
- 1994-09-23 TW TW083108792A patent/TW284760B/zh active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU9049391A (en) * | 1990-12-20 | 1992-07-22 | Warner-Lambert Company | 2-acylamido derivatives of 3,4-dihydro-3-oxo-quinoxaline having pharmaceutical activity |
AU4613293A (en) * | 1992-09-04 | 1994-03-10 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds, their production and use |
Also Published As
Publication number | Publication date |
---|---|
CN1114834A (zh) | 1996-01-10 |
KR950704269A (ko) | 1995-11-17 |
EP0670831A1 (en) | 1995-09-13 |
TW284760B (ko) | 1996-09-01 |
CA2150345A1 (en) | 1995-04-06 |
KR100196356B1 (ko) | 1999-06-15 |
AU7666094A (en) | 1995-04-18 |
WO1995009159A1 (en) | 1995-04-06 |
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MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |