EP0670831A1 - Quinoxaline derivative as antidiabetic agent - Google Patents
Quinoxaline derivative as antidiabetic agentInfo
- Publication number
- EP0670831A1 EP0670831A1 EP94927085A EP94927085A EP0670831A1 EP 0670831 A1 EP0670831 A1 EP 0670831A1 EP 94927085 A EP94927085 A EP 94927085A EP 94927085 A EP94927085 A EP 94927085A EP 0670831 A1 EP0670831 A1 EP 0670831A1
- Authority
- EP
- European Patent Office
- 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.)
- Withdrawn
Links
- 239000003472 antidiabetic agent Substances 0.000 title claims abstract description 10
- 229940125708 antidiabetic agent Drugs 0.000 title claims abstract description 8
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title abstract description 476
- 150000003839 salts Chemical class 0.000 claims abstract description 497
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 1861
- -1 1 ,3 - dioxolanyl group Chemical group 0.000 claims description 1447
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 498
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 447
- 125000003545 alkoxy group Chemical group 0.000 claims description 409
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 306
- 125000005843 halogen group Chemical group 0.000 claims description 236
- 125000002252 acyl group Chemical group 0.000 claims description 214
- 125000003277 amino group Chemical group 0.000 claims description 202
- 125000001424 substituent group Chemical group 0.000 claims description 191
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 137
- 125000003342 alkenyl group Chemical group 0.000 claims description 135
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 125
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 119
- 229910052757 nitrogen Inorganic materials 0.000 claims description 91
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 90
- 125000000623 heterocyclic group Chemical group 0.000 claims description 71
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 60
- 125000004043 oxo group Chemical group O=* 0.000 claims description 59
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 55
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 55
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 51
- 150000003536 tetrazoles Chemical group 0.000 claims description 50
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 49
- 125000002947 alkylene group Chemical group 0.000 claims description 45
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229920006395 saturated elastomer Polymers 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 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
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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 12
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 11
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 10
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl 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
- 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
- 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
- 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 32
- 239000007800 oxidant agent Substances 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- XCOQDPOVESJHNO-UHFFFAOYSA-N 3-methyl-4-oxido-N-[3-[5-(1,3-thiazol-2-yl)-1-benzofuran-2-yl]but-2-enyl]quinoxalin-4-ium-2-carboxamide Chemical compound CC(=CCNC(=O)c1nc2ccccc2[n+]([O-])c1C)c1cc2cc(ccc2o1)-c1nccs1 XCOQDPOVESJHNO-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
- AUQAGCOAFZVKNT-UHFFFAOYSA-N 3-methyl-n-[3-[5-(2-methyltetrazol-5-yl)-1-benzofuran-2-yl]but-2-enyl]-4-oxidoquinoxalin-4-ium-2-carboxamide Chemical compound N=1C2=CC=CC=C2[N+]([O-])=C(C)C=1C(=O)NCC=C(C)C(OC1=CC=2)=CC1=CC=2C=1N=NN(C)N=1 AUQAGCOAFZVKNT-UHFFFAOYSA-N 0.000 claims 1
- CCEKDSXCSMKCMQ-UHFFFAOYSA-N [3-(1-benzofuran-2-yl)but-2-enyl-(3-methyl-4-oxidoquinoxalin-4-ium-2-carbonyl)amino]methyl propanoate Chemical compound C1=CC=C2[N+]([O-])=C(C)C(C(=O)N(CC=C(C)C=3OC4=CC=CC=C4C=3)COC(=O)CC)=NC2=C1 CCEKDSXCSMKCMQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- QGDHXCXJWVSWFZ-UHFFFAOYSA-N methyl n-[3-(1-benzofuran-2-yl)but-2-enyl]-n-(3-methyl-4-oxidoquinoxalin-4-ium-2-carbonyl)carbamate Chemical compound C1=CC=C2[N+]([O-])=C(C)C(C(=O)N(CC=C(C)C=3OC4=CC=CC=C4C=3)C(=O)OC)=NC2=C1 QGDHXCXJWVSWFZ-UHFFFAOYSA-N 0.000 claims 1
- UNSZIPLFYZRIDM-UHFFFAOYSA-N n-[3-(1-benzofuran-2-yl)but-2-enyl]-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxamide Chemical compound C1=CC=C2OC(C(=CCNC(=O)C=3C(=[N+]([O-])C4=CC=CC=C4N=3)C)C)=CC2=C1 UNSZIPLFYZRIDM-UHFFFAOYSA-N 0.000 claims 1
- AXPHHSPLYBVHPP-UHFFFAOYSA-N n-[3-[5-(2,5-dimethyl-1,3-thiazol-4-yl)-1-benzofuran-2-yl]but-2-enyl]-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxamide Chemical compound N=1C2=CC=CC=C2[N+]([O-])=C(C)C=1C(=O)NCC=C(C)C(OC1=CC=2)=CC1=CC=2C=1N=C(C)SC=1C AXPHHSPLYBVHPP-UHFFFAOYSA-N 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
- FGIGRNPAGDPICO-UHFFFAOYSA-N n-[[5-(2,5-dimethyl-1,3-thiazol-4-yl)-1-benzofuran-3-yl]methyl]-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxamide Chemical compound S1C(C)=NC(C=2C=C3C(CNC(=O)C=4C(=[N+]([O-])C5=CC=CC=C5N=4)C)=COC3=CC=2)=C1C FGIGRNPAGDPICO-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 description 232
- 125000004432 carbon atom Chemical group C* 0.000 description 110
- 125000001589 carboacyl group Chemical group 0.000 description 41
- 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
- 206010012601 diabetes mellitus Diseases 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 230000002218 hypoglycaemic effect Effects 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 208000001072 type 2 diabetes mellitus Diseases 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 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
- 210000004027 cell Anatomy 0.000 description 3
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 description 3
- 125000003884 phenylalkyl group Chemical group 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 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
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 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
- 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
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 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
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 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
- 208000002249 Diabetes Complications Diseases 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
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 239000007952 growth promoter Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 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 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229940126904 hypoglycaemic agent Drugs 0.000 description 2
- 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
- 210000004185 liver Anatomy 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000001422 pyrrolinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000000021 stimulant Substances 0.000 description 2
- 125000005504 styryl group Chemical group 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
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
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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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—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
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- 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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- 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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- 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
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- 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
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- 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
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- 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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- 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
Definitions
- the present invention relates to an antidiabetic agent.
- R-CO-NH S0 2 NHCONHR 2 wherein R is a group of the formula:
- R 2 is alkyl, alkenyl, cycloalkyl, etc. Said compounds are similar to the compounds of this invention in the basic structure and also in the pharmacological activity but are distinguished from the compounds of this invention in the substituent on the phenyl ring in the substituent -CONR 3 R 4 at 2 position of quinoxaline ring.
- DD-273254-A discloses selective reduction of quinoxaline-di-N - oxide derivatives of the formula:
- R-- is H, Cl, methyl, or methoxy
- R 2 is OH, alkoxy or ⁇ - hydroxyethylamino, to give the corresponding N-4-monoxides which are useful as an intermediate for pharmaceuticals and pesticides.
- R is H, halogen, alkyl, OR 3 , NR 4 R 5 , etc.
- R 6 and R 7 are H, halogen, alkyl, OR 3 , NR 4 R 5 , etc., which are useful for treating disorders such as asthma, hay-fever, urticaria, eczema or atopic dermatitis.
- EP-23785 discloses substituted alkoxy-phenoxy-quinoxaline(s), N oxide(s) thereof of the formula:
- A, B, D, E, J, U and V are H, halogen, nitro, CN, amino, mono- or di - substituted amino, alkyl, alkoxy, carbamoyi, etc.; Y and X are O or S; R 1 and R 2 are H, alkyl, alkenyl, etc.; and W is CN, CSNH , etc., which are useful as pre- and post-emergence selective herbicides.
- EP-26622 discloses also similar quinoxalinyl-amino-phenoxyalkanoic acids which are useful as pre- and post - emergence selective herbicides.
- R is H or methyl
- n is 0 or an integer of 1 to 4
- 1 and m are 0 or 1 , but no pharmacological activity of these compound is mentioned.
- DD-284585-A discloses quinoxaline-1 ,4-di-N-oxides of the formula:
- R 1 is H or optionally substituted alkyl
- R 2 is H, optionally substituted alkyl, or hydroxyethylcarbamoyl, which are useful as a medicinal feedstuff to protect piglets from gastro-intestinal disorders.
- BE-721725 discloses 3-carboxamidoquinoxaline-di-N-(1 ,4) - oxides of the formula:
- is H, alkyl, alkoxy, or Cl;
- R and R 3 are H, optionally substituted alkyl, or may form with N a 5- or 6- membered heterocyclic ring;
- X is 0 or S; and
- R4 is optionally substituted alkyl or optionally substituted phenyl, which have antibacterial activity.
- Similar compounds are also disclosed in many literatures such as BE-721726, BE-721728, BE-738246, BE-742970, DT-2012743, NL - 7305048, BE-846532, GB-1308370, JP-B-46-23264, JP-B-45-24988, and JP-B • 45-24989.
- NL-7206031 discloses 2-formyl-3-carbamoyl-quinoxaline 1 ,4 - dioxides of the formula:
- R-- and R 2 are H, optionally substituted aliphatic or cycloaliphatic group, or form a 5- to 7-membered ring optionally containing 0 or S, Z is NOH or NNHC(Y)R 3 , which have antimicrobial activity.
- NL-7206601 discloses 2,3-disubstituted quinoxaline-1 ,4-dioxides of the formula:
- R 1 is phenyl optionally substituted by alkyl, alkoxy, halogen or CF 3
- R 2 is -CONR 3 R 4 where R 3 and R 4 are H or alkyl or form together alkylene optionally containing O, S or N heteroatom, which are useful as bactericides and amoebicides.
- R 3 and R 4 are H or alkyl or form together alkylene optionally containing O, S or N heteroatom, which are useful as bactericides and amoebicides.
- Similar compounds are also disclosed in BE-763377, DT - 2228802, and BE-904482.
- EP-12725 discloses quinoxaline di-N-oxides of the formula:
- R 1 is H or alkyl
- R 2 and R 3 are alkyl or NR 2 R 3 forms 4-5C heterocyclic ring optionally substituted by alkyl
- R 4 is H, methoxy, methylthio, OH, F, Cl, Br or CN, which are useful as broad-spectrum antimicrobial agents, esp. as veterinary medicaments, and animal growth promoters.
- CH-619456 discloses 6-phenylthio-quinoxaline-1 ,4-dioxide derivatives of the formula:
- DT-2052359 discloses quinoxaline 1 ,4-dioxides of the formula:
- R-* and R 2 are each H, alkyl or alkoxy, or form together methyienedioxy;
- R 3 is H, optionally unsaturated aliphatic residue (optionally substituted by CN, COOH, carbamoyi, alkylamino, etc.), a 5- or 6-membered cycloaliphatic residue (optionally substituted by alkyl), aryialkyi or furfuryl;
- R is H, or NR3R4 is optionally unsaturated 5- or 6-membered heterocyclic ring optionally substituted by alkyl;
- R 5 is optionally substituted and optionally unsaturated aliphatic, cycloaliphatic, araliphatic aromatic or heterocyclic residue, which have antiprotozoal and antibacterial activity. Similar compounds are also disclosed in DT-2052279.
- DT-2120501 discloses 3-substituted quinoxaline-2-carboxamido - 1 ,4-dioxides of the formula:
- X is H, methyl, methoxy, CF 3 , F, Cl, or Br
- Y is alkylthio, alkylsulfinyl, or alkylsulfonyl
- R' is H or alkyl
- R" is H or alkyl optionally substituted by amino alkylamino, dialkylamino, pyrrolidino, piperidino, etc., which are useful as broad spectrum antibacterial agents, growth stimulants especially for pigs and poultry.
- Similar compounds are also disclosed in BE-764088, BE-773396, and DT-2212932.
- US-3185688 discloses quinoxaline derivatives of the formula:
- Z is NR(CH 2 ) n NR 1 R 2 , NR(CH 2 ) n Oalkyl, NR(CH 2 ) n Salkyl;
- X and R are H or alkyl;
- R-* and R 2 are alkyl, or
- NR 1 R 2 is morpholino, piperidino, pyrrolidino; and
- n is 2 - 4, which are useful as tranquilizers.
- Similar compounds are also disclosed in US-3192212 and FR-2211006.
- the antidiabetic agent of the present invention comprises as an active ingredient at least one of quinoxaline derivatives of the formula (1): wherein R 1 is hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is hydrogen atom, a lower alkyl group having optionally a halogen substituent, phenyl group, a morpholino-substituted lower alkyl group or an imidazolyl-substituted lower alkyl group, n and m are each 0 or 1 , r is 1 or 2, R 3 and R 4 are the same or different and each a) hydrogen atom; b) a lower alkyl group; c) a phenyl-lower alkoxycarbonyl group; d) a lower alkanoyloxy-substituted lower al
- R 5 is hydrogen atom, a lower alkoxy-substituted lower alkoxy group, a lower alkoxy group, an amino group having optionally a lower alkyl substituent, a halogen atom, nitro group, hydroxy group, a lower alkyl group having optionally a hydroxy substituent, a lower alkenyloxy group, a carboxyl-substituted lower alkoxy group, a lower alkoxycarbonyl-substituted lower alkoxy group, a lower alkoxycarbonyl group, a halogen-substituted lower alkoxy group, a hydroxy - substituted lower alkoxy group, a phenyl-lower alkoxy group having optionally a substituent selected from a lower alkyl group and a lower alkoxy group on the phenyl moiety, a 1 ,3-dioxolanyl group having optionally a substituent selected from a lower alkyl group and a lower al
- R 8 substitutes on the above heterocyclic group, and is hydrogen atom, oxo group, a lower alkyl group having optionally a hydroxy substituent, a halogen atom, nitro group, a lower alkoxy group, cyano group, a lower alkoxycarbonyl group, a phenyl-lower alkoxy group having optionally an amino group having optionally a lower alkanoyl substituent on the phenyl moiety, a carboxyl - substituted lower alkoxy group, carboxyl group, a lower alkoxycarbonyl - substituted lower alkoxy group, hydroxy group, a lower alkoxy-substituted lower alkoxy group, a lower alkenyloxy group,
- o -r u ⁇ nsaturated heterocyclic group having 1 to 4 hetero atoms selected from nitrogen atom, oxygen atom and sulfur atom, R 45 bonds to said heterocyclic group and is hydrogen atom, a lower alkyl group, a lower alkoxy-substituted lower alkyl group, phenyl group or oxo group), a group of the formula:
- R 3 and R 4 may combine together with the adjacent nitrogen atom to which they bond to form 1 ,2,3,4-tetrahydroisoquinolyl group, said heterocyclic group having optionally a lower alkoxy substituent, or a salt thereof.
- the present invention provides also novel quinoxaline derivatives of the formula (1 ) as described above wherein all the symbols are the same as defined above except that n is 0 and the group R 5 excludes hydrogen atom and further provided that when R 1 is hydrogen atom, R 2 is methyl group, R 3 is hydrogen atom, and m is 0, then R 4 is not 2-(imidazol-2-yl)ethyl, 2-(indol-3 - yl)ethyl, or sec-butyl, and a salt thereof.
- diabetes is caused by the absolute lack of the secretion of insulin and arises either acutely or subacutely, and includes, insulin dependent diabetes mellitus (IDDM) which requires the insulin-treatment, non insulin dependent diabetes mellitus
- IDDM insulin dependent diabetes mellitus
- NIDDM insulin-treatment-related diabetes mellitus
- MRDM malnutrition-related diabetes mellitus
- a cause of IDDM is estimated to be the destruction of pancreatis ⁇ -cells by auto-immune system.
- the pancreatis ⁇ - cells are considered to be destroyed by HLA antigen, cytokine virus, etc. (cf.
- NIDDM Koji NAKANISHI, Tetsuro KOBAYASHI, Mitsuru HARA; Tonyobyogaku (Diabetology) 1989: edited by Mikinori KOSAKA, Yasuo AKANUMA, Shindan- to-Chiryo sha, 1989, pages 226-244).
- the cause of NIDDM is estimated to be (i) congenital anomaly in pancreatin, i.e. anomaly in adaptability to the increase in insulin consumption, or (ii) disorder in insulin activity induced by various factors such as aging, obesity, stress, etc. (Hiroo IMURA; Tonyobyogaku-no-Shinpo (Progress in Diabetology) 1989, No.
- the important causes of hyperglycemia is considered to be the decrease in the uptake of glucose at the peripheral tissue, especially at the muscle, and the increase in glucose secretion at the liver.
- the most common drug therapy for diabetes is treatment with insulin or sulfonylurea agent (agent for promotion of insulin secretion), which are both based on the supplement of insulin, but these treatment have difficulty in strict blood glucose level control, and sometimes they induce hyperinsulin serum or hypoglycemia.
- a compound which promotes the uptake of glucose at the muscle without promoting the secretion of insulin would be a new kind of hypoglycemic agent without hyperinsulinism nor hypoglycemia and would be useful for treatment of diabetes.
- the quinoxaline derivatives of the above formula (1 ) and salts thereof (hereinafter referred to as the compounds of the present invention) promote the uptake of 2-deoxyglucose (2DG) against L6 cells, cell line of rat striated muscle (muscular cells) and also promote the consumption of glucose by which they show hypoglycemic activity.
- the compounds of the present invention show hypoglycemic activity in db/db mice and KK-Ay mice, which are diabetic animal model (L.
- the compounds of the present invention promote the uptake of glucose at the muscle and do not affect the insulin secretion and the glucose release at the liver so that they do not show acute hypoglycemic activity and do not affect oral glucose tolerance test.
- the antidiabetic agent of the present invention is useful for treatment of diabetes and diabetic complications such as diabetic blood vessel disorder, diabetic retinopathy, diabetic nephropathy, diabetic neuropathy, etc.
- the lower alkyl group includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, etc.
- the halogen atom is fluorine atom, chlorine atom, bromine atom or iodine atom.
- the lower alkyl group having optionally a halogen substituent includes, for example, in addition to the above mentioned lower alkyl groups, a straight chain or branched chain alkyl group having 1 to 6 carbon atoms having optionally 1 to 3 halogen substituents, such as trifluoromethyl, trichloromethyl, chloromethyl, bromomethyl, fluoromethyl, iodomethyl, difluoromethyl, dibromo - methyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 3-chloropropyl,
- the morpholino-substituted lower alkyl group includes a morpholino-substituted alkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, morpholinomethyl, 2-morpholinoethyl, 1-morpholinoethyl, 3-(2-morpholinyl) - propyl, 4-(3-morpholinyl)butyl, 1 ,1-dimethyl-2-(2-morpholinyl)ethyl, 5- morpholinopentyl, 6-morpholinohexyl, 2-methyl-3-morpholinopropyl, etc.
- the imidazolyl-substituted lower alkyl group includes an imidazolyl-substituted alkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, (1 - imidazolyl)methyl, 2-(1-imidazolyl)ethyl, 1-(2-imidazolyl)ethyl, 3-(4-imidazolyl) - propyl, 4-(5-imidazolyl)butyl, 1 ,1-dimethyl-2-(2-imidazolyl)ethyl, 5-(4 - imidazoly pentyl, 6-(1-imidazolyl)hexyl, 2-methyl-3-(1-imidazolyl)propyl, etc.
- the lower alkylene group includes a straight chain or branched chain alkylene group having 1 to 6 carbon atoms, for example, methylene, ethylene, trimethylene, 2-methyltrimethylene, 2,2-dimethyltrimethylene, 1 - methyltrimethylene, methylmethylene, ethylmethylene, tetramethylene, pentamethylene, hexamethylene, etc.
- the lower alkoxy group includes a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy, etc.
- the amino group being optionally substituted by a lower alkyl group includes an amino group which may optionally be substituted by 1 to 2 substituents of a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, amino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, tert-butylamino, pentylamino, hexylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, dipentylamino, dihexylamino, N-methyl-N-ethylamino, N-ethyl-N-propylamino, N-methyl-N - butylamino, N-methyl-N-hexylamino, and the like.
- the lower alkyl group having optionally a hydroxy substituent includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms which may optionally have 1 to 3 hydroxy substituents, for example, hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 1-hydroxyisopropyl, 3-hydroxy - propyl, 2,3-dihydroxypropyl, 4-hydroxybutyl, 1 ,1-dimethyl-2-hydroxyethyl, 5,5,4 - trihydroxypentyl, 5-hydroxypentyl, 6-hydroxyhexyl, 2-methyl-3-hydroxypropyl, 2,3-dihydroxyethyl, 3,4-dihydroxybutyl, 5,6-dihydroxyhexyl, and the like.
- the lower alkenyloxy group includes a straight chain or branched chain alkenyloxy group having 2 to 6 carbon atoms, for example, allyloxy, 2 - butenyloxy, 3-butenyloxy, 1-methylallyloxy, 2-pentenyloxy, 2-hexenyloxy, and the like.
- the carboxy-substituted lower alkoxy group includes a carboxy - alkoxy group wherein the alkoxy moiety is a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, for example, carboxymethoxy, 2 - carboxyethoxy, 1 -carboxyethoxy, 3-carboxypropoxy, 4-carboxybutoxy, 5 - carboxypentyloxy, 6-carboxyhexyloxy, 1 ,1-dimethyl-2-carboxyethoxy, 2-methyl - 3-carboxypropoxy, and the like.
- the lower alkoxycarbonyl-substituted lower alkoxy group includes a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms which is substituted by a straight chain or branched chain alkoxycarbonyl group having 1 to 6 carbon atoms in the alkoxy moiety, for example, methoxy - carbonylmethoxy, 3-methoxycarbonylpropoxy, ethoxycarbonylmethoxy, 3 - ethoxycarbonylpropoxy, 4-ethoxycarbonylbutoxy, 5-isopropoxycarbonyl - pentyloxy, 6-propoxycarbonylhexyloxy, 1 ,1 -dimethyl-2-butoxycarbonylethoxy, 2 methyl-3-tert-butoxycarbonylpropoxy, 2-pentyloxycarbonylethoxy, hexyloxy - carbonylmethoxy, and the like.
- the lower alkoxycarbonyl group includes a straight chain or branched chain alkoxycarbonyl group having 1 to 6 carbon atoms in the alkoxy moiety, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, and the like.
- the halogen-substituted lower alkoxy group includes a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms which has 1 to 3 halogen substituents, for example, trifluoromethoxy, trichloromethoxy, chloromethoxy, bromomethoxy, fluoromethoxy, iodomethoxy, difluoromethoxy, dibromomethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 3 - chloropropoxy, 2,3-dichloropropoxy, 4,4,4-trichlorobutoxy, 4-fluorobutoxy, 5 - chloropentyloxy, 3-chloro-2-methylpropoxy, 5-bromohexyloxy, 5,6-dichloro - hexyloxy, 5-bromohexyloxy, 5,6-dichlorohexyloxy, and the like.
- halogen substituents for
- the hydroxy-substituted lower alkoxy group includes a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms which is substituted by 1 to 3 hydroxy groups, for example, hydroxymethoxy, 2-hydroxy - ethoxy, 1 -hydroxyethoxy, 1 -hydroxypropoxy, 3-hydroxypropoxy, 2,3-dihydroxy- propoxy, 4-hydroxybutoxy, 1 ,1-dimethyl-2-hydroxyethoxy, 5,5,4-trihydroxy - pentyloxy, 5-hydroxypentyloxy, 6-hydroxyhexyloxy, 1-hydroxyisopropoxy, 2 - methyl-3-hydroxy ⁇ ropoxy, 2,3-dihydroxyethoxy, 3,4-dihydroxybutoxy, 5,6 - dihydroxyhexyloxy, and the like.
- the phenyl-lower alkoxy group having optionally a substituent selected from a lower alkyl group and a lower alkoxy group on the phenyl moiety includes a phenylalkoxy group wherein the alkoxy moiety is a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms which may optionally have 1 to 3 substituents selected from a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms and a straight chain or branched chain alkyl group having 1 to 6 carbon atoms on the phenyl moiety, for example, benzyloxy, 2-phenylethoxy, 1-phenylethoxy, 3-phenylpropoxy, 4 - phenylbutoxy, 1 ,1-dimethyl-2-phenylethoxy, 5-phenylpentyloxy, 6-phenyl - hexyloxy, 2-methyl-3-phenylpropoxy, 2-(3-methoxyphenyl)ethoxy,
- the 1 ,3-dioxolanyl group having optionally a lower alkyl substituent includes a 1 ,3-dioxolanyl group which may optionally be substituted by 1 to 3 straight chain or branched chain alkyl groups having 1 to 6 carbon atoms, for example, 1 ,3-dioxolanyl, 2-methyl-1 ,3-dioxolanyl, 4-ethyl-1 ,3 - dioxolanyl, 2-propyl-1 ,3-dioxolanyl, 4-butyl-1 ,3-dioxolanyl, 2-pentyl-1 ,3 - dioxolanyl, 4-hexyl-1 ,3-dioxolanyl, 2,4-dimethyl-1 ,3-dioxolanyl, 2,4,5-trimethyl - 1 ,3-dioxolanyl, and the like.
- the lower alkanoyl group includes a straight chain or branched chain alkanoyl group having 1 to 6 carbon atoms, for example, formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, t-butylcarbonyl, hexanoyl, and the like.
- the morpholino-substituted lower alkoxy group includes a morpholino-substituted alkoxy group wherein the alkoxy moiety is a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, for example, morpholinomethoxy, 2-morpholinoethoxy, 1-morpholinoethoxy, 3-(2 - morpholinyl)propoxy, 4-(3-morpholinyl)butoxy, 1 ,1 -dimethyl-2-(2-morpholinyl) - ethoxy, 5-morpholinopentyloxy, 6-morpholinohexyloxy, 2-methyl-3-morpholino - propoxy, and the like.
- the phenyl-lower alkyl group includes a phenyl-alkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, benzyl, 2-phenylethyl, 1 -phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 6-phenylhexyl, 1 ,1-dimethyl-2 - phenylethyl, 2-methyl-3-phenylpropyl, and the like.
- the phenyl-lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety includes a phenyl-alkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms and may optionally have 1 to 3 straight chain or branched chain alkoxy substituents having 1 to 6 carbon atoms on the phenyl moiety, for example, in addition to the above mentioned phenyl-lower alkyl group, 2-(3 - methoxyphenyl)ethyl, 1-(4-methoxyphenyl)ethyl, 2-methoxbenzyl, 3-methoxy - benzyl, 4-methoxybenzyl, 3-(2-ethoxyphenyl)propyl, 4-(3-ethoxyphenyl)butyl, 1 ,1 -dimethyl-2-(4-ethoxyphenyl)ethyl, 5-(4-iso
- the furyl-substituted lower alkyl group includes a furyl-substituted alkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, (2-furyl)methyl, 2-(3-furyl)ethyl, 1-(2-furyl)ethyl, 3-(2-furyl)propyl, 4-(3-furyl)butyl, 5-(2-furyl)pentyl, 6-(3-furyl) - hexyl, 1 ,1-dimethyl-2-(2-furyl)ethyl, 2-methyl-3-(3-furyl)propyl, and the like.
- the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, (2-furyl)methyl, 2-(3-furyl)ethyl, 1-(2-furyl)ethyl,
- the lower alkoxy-lower alkyl group includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms which is substituted by a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, for example, methoxymethyl, 2-ethoxyethyl, 1-methoxyethyl, 3-methoxypropyl, 4 - ethoxybutyl, 6-propoxyhexyl, 5-isopropoxypentyl, 1 ,1-dimethyl-2-butoxyethyl, 2 methyl-3-tert-butoxypropyl, 2-pentyloxyethyl, hexyloxymethyl, and the like.
- the alkenyl group includes a straight chain or branched chain alkenyl group with 1 to 3 double bonds having 2 to 12 carbon atoms, for example, vinyl, allyl, 3-methyl-2-butenyl, 2-butenyl, 3-butenyl, 1-methylallyl, 2 - pentenyl, 2-hexenyl, 1-heptenyl, 1-octenyl, 1 -nonenyl, 1-decenyl, 1-undecenyl, 2-dodecenyl, 2-heptenyl, 3-heptenyl, 3-methyl-4-heptenyl, 2-methyl-5-heptenyl, 4-methyl-2-heptenyl, 3-methyl-l-heptenyl, 1 ,3-heptadienyl, 1 ,4-heptadienyl, 1,5 heptadienyl, 1 ,6-heptadienyl, 2,4-heptadienyl, 2-methyl-2,4-
- the cycloalkyl-lower alkyl group includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, which is substituted by a cycloalkyl group having 3 to 8 carbon atoms, for example, cyclohexylmethyl, 2-cyclopropylethyl, 1 -cyclobutylethyl, 3-cyclopentylpropyl, 4-cyclohexylbutyl, 2,2-dimethyl-3-cycloheptylpropyl, 5-cyclooctylpentyl, 6-cyclohexylhexyl, and the like.
- the naphthyl-lower alkyl group includes a naphthyl-alkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, ⁇ -naphthylmethyl, ⁇ -naphthylmethyl,
- the phenylthio-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety includes a phenylthio-alkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms and may optionally have 1 to 3 substituents of straight chain or branched chain alkoxy group having 1 to 3 carbon atoms on the phenyl moiety, for example, phenylthiomethyl, 2-phenylthioethyl, 1 - phenylthioethyl, 3-phenylthiopropyl, 4-phenylthiobutyl, 5-phenylthiopentyl, 6 - phenylthiohexyl, 1 ,1-dimethyl-2-phenylthioethyl, 2-methyl-3-phenylthiopropyl, (2-methoxyphenylthio)methyl, (3-methoxypheny
- the phenylsulfinyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety includes a phenylsulfinylalkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, and may optionally have 1 to 3 substituents of straight chain or branched chain alkoxy group having 1 to 6 carbon atoms on the phenyl moiety, for example, phenylsulfinylmethyl, 2-phenylsulfinylethyl, 1 - phenylsulfinylethyl, 3-phenylsulfinylpropyl, 4-phenylsulfinylbutyl, 5-phenyl - sulfinylpentyl, 6-phenylsulfinylhexyl, 1 ,1 -dimethyl-2-phenylsulfin
- the phenylsulfonyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety includes a phenylsulfonyl-alkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, which may optionally have 1 to 3 substituents of straight chain or branched chain alkoxy group having 1 to 6 carbon atoms on the phenyl moiety, for example, phenylsulfonyl - methyl, 2-phenylsulfonylethyl, 1-phenylsulfonylethyl, 3-phenylsulfonylpropyl, 4 - phenylsulfonylbutyl, 5-phenylsulfonylpentyl, 6-phenylsulfonylhexyl, 1 ,1 - dimethyl-2-phenylsulfon
- the 5- to 14-membered saturated or unsaturated hetero - monocyclic, heterobicyclic or heterotricyclic group having 1 to 4 heteroatoms selected from nitrogen atom, oxygen atom and sulfur atom includes, for example, pyrrolidinyl, piperidinyl, piperazinyl, morpholino, pyridyl, thienyl, quinolyl, 1 ,4-dihydroquinolyl, benzothiazolyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, carbostyril, 3,4-dihydrocarbostyril, 1 ,2,3,4-tetrahydroquinolyl, indolyl, isoindolyl, indolinyl, benzimidazolyl, benzoxazolyl, imidazolidinyl, isoquinolyl, quinazolidinyl, quinoxalinyl, cinnony
- the lower alkyl group which is substituted by a 5- to 14 - membered saturated or unsaturated heteromonocyclic, heterobicyclic or heterotricyclic group having 1 to 4 heteroatoms selected from nitrogen atom, oxygen atom and sulfur atom includes, for example, pyrrolidinylmethy, 2 - piperidinylethyl, 3-piperazinylpropyl, 4-morpholinobutyl, (2-pyridyl)methyl, (3 - pyridyl)methyl, (2-thienyl)methyl, (3-quinolyl)methyl, 5-(6-quinolyl)pentyl, 6-(1 ,4 dihydro-2-quinolyl)hexyl, (2-benzothiazolyl)methyl, 2-(3-pyrazinyl)ethyl, 1-(2 - pyrimidyl)ethyl, 3-(3-pyridazinyl)propyl, 4-(2-pyrrolyl)butyl, 5-(
- the phenoxy-substituted lower alkyl group includes a phenoxyalkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, phenoxymethyl, 2 - phenoxyethyl, 1-phenoxyethyl, 3-phenoxypropyl, 4-phenoxybutyl, 5-phenoxy - pentyl, 6-phenoxyhexyl, 1 ,1-dimethyl-2-phenoxyethyl, 2-methyl-3-phenoxy - propyl, and the like.
- the phenyl-lower alkoxy group which may optionally have an amino substituent having optionally a lower alkanoyl substituent on the phenyl moiety includes a phenylalkoxy group, wherein the alkoxy moiety is a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, which may optionally have 1 to 3 substituents of amino group having optionally a straight chain or branched chain alkanoyl group having 1 to 6 carbon atoms, for example, benzyloxy, 2-phenylethoxy, 1-phenylethoxy, 3-phenylpropoxy, 4 - phenylbutoxy, 5-phenylpentyloxy, 6-phenylhexyloxy, 1 ,1-dimethyl-2-phenyl - ethoxy, 2-methyl-3-phenylpropoxy, 4-acetylaminobenzyloxy, 2-(2-propionyl - aminophenyl)ethoxy, 1 -(3-buty
- the lower alkoxy-substituted lower alkoxy group includes a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms which is substituted by a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, for example, methoxymethoxy, 3-methoxypropoxy, 4 - ethoxybutoxy, 6-propoxyhexyloxy, 5-isopropoxypentyloxy, 1 ,1 -dimethyl-2 - butoxyethoxy, 2-methyl-3-tert-butoxypropoxy, 2-pentyloxyethoxy, hexyloxy - methoxy, and the like.
- the lower alkanoyloxy-substituted lower alkyl group includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms which is substituted by a straight chain or branched chain alkanoyloxy group having 2 to 6 carbon atoms, for example, acetyloxymethyl, 2,2-dimethylpropionyloxy - methyl, propionyloxymethyl, 2-propionyloxyethyl, 1 -acetyloxyethyl, 1-butyryl - oxyethyl, 3-acetyloxypropyl, 4-isobutyryloxybutyl, 5-pentanoyloxypentyl, 6-tert - butylcarbonyloxyhexyl, 1 ,1 -dimethyl-2-hexanoyloxyethyl, 2-methyl-3-acetyloxy - propyl, and the like.
- the halogen-substituted lower alkyl group includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms which is substituted by 1 to 3 halogen atoms, for example, trifluoromethyl, trichloro - methyl, chloromethyl, bromomethyl, fluoromethyl, iodomethyl, difluoromethyl, dibromomethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 3 - chloropropyl, 2,3-dichloropropyl, 4,4,4-trichlorobutyl, 4-fluorobutyl, 5-chloro - pentyl, 3-chloro-2-methylpropyl, 5-bromohexyl, 5,6-dichlorohexyl, 5-bromo - hexyl, 5,6-dichlorohexyl, and the like.
- the tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring includes a tetrazolyl group having optionally a straight chain or branched chain alkyl group having 1 to 6 carbon atoms on the tetrazole ring, for example, tetrazolyl, 1-methyltetrazolyl, 2-methyltetrazolyl, 5-ethyltetrazolyl, 5 propyltetrazolyl, 1-butyltetrazolyl, 2-pentyltetrazolyl, 1 -hexyltetrazolyl, and the like.
- the phenyl group having optionally a substituent selected from a lower alkyl group, a lower alkoxy-substituted lower alkoxy group, hydroxy group, a halogen atom and a lower alkoxy group includes a phenyl group which may optionally have 1 to 3 substituents selected from a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms which is substituted by a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, hydroxy group, a halogen atom and a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, for example, phenyl, 2-methylphenyl, 3 - methylphenyl, 4-methylphenyl, 2-ethyl phenyl, 3-ethylphenyl, 4-ethylphenyl, 3 - isopropylphenyl,
- the lower alkenyl group includes a straight chain or branched chain alkenyl group having 2 to 6 carbon atoms, for example, vinyl, allyl, 2- butenyl, 3-butenyl, 1-methylallyl, 2-pentenyl, 2-hexenyl, and the like.
- the morpholinocarbonyl-lower alkoxy group includes a morpholinocarbonylalkoxy group wherein the alkoxy moiety is a straight chain or branched chain alkoxyl group having 1 to 6 carbon atoms, for example, morpholinocarbonylmethoxy, 2-morpholinocarbonylethoxy, 1-morpholino - carbonylethoxy, 3-(2-morpholinocarbonyl)propoxy, 4-(3-morpholinocarbonyl) - butoxy, 1 ,1-dimethyl-2-(2-morpholinylcarbonyl)ethoxy, 5-morpholinylcarbonyl - pentyloxy, 6-morpholinocarbonylhexyloxy, 2-methyl-3-morpholinocarbonyl - propoxy, and the like.
- morpholinocarbonylalkoxy group wherein the alkoxy moiety is a straight chain or branched chain alkoxyl group having 1 to 6 carbon atoms, for example, morpholinocarbonylme
- the morpholinocarbonyl-lower alkyl group includes a morpholinocarbonylalkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, morpholinocarbonylmethyl, 2-morpholinocarbonylethyl, 1 -morpholinocarbonyl - ethyl, 3-(2-morpholinocarbonyl)propyl, 4-(3-morpholinocarbonyl)butyl, 1 ,1 - dimethyl-2-(2-morpholinocarbonyl)ethyl, 5-morpholinocarbonylpentyl, 6 - morpholinocarbonylhexyl, 2-methyl-3-morpholinocarbonylpropyl, and the like.
- morpholinocarbonylalkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, morpholinocarbonylmethyl,
- the cycloalkylcarbonyl group includes a cycloalkylcarbonyl group having 3 to 8 carbon atoms in the cycloalkyl moiety, for example, cyclopropyl - carbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl, and the like.
- the phenyl-lower alkenylcarbonyl group includes a phenylalkenyl carbonyl group wherein the alkenylcarbonyl moiety is a straight chain or branched chain alkenylcarbonyl group having 3 to 6 carbon atoms in the alkenylcarbonyl moiety, for example, cinnamoyi, 4-phenyl-2-butenoyl, 4-phenyl • 3-butenoyl, 5-phenyl-4-pentenoyl, 5-phenyl-3-pentenoyl, 5-phenyl-2 - pentenoyi, 6-phenyl-5-hexenoyl, 6-phenyl-4-hexenoyl, 6-phenyl-3-hexenoyl, 6 - phenyl-2-hexenoyl, 2-methyl-4-phenyl-3-butenoyl, 2-methyl-cinnamoyl, 1 - methyl-cinnamoyl, and the like.
- the 5- to 6-membered saturated heterocyclic group which is formed by combining R 6 and R 7 , R 9 and R 10 , R 40 and R 41 or R 52 and R 53 together with the adjacent nitrogen atom with or without being intervening with nitrogen atom or oxygen atom, for example, pyrrolidinyl, piperidinyl, piperazinyl, morpholino, and the like.
- the above heterocyclic group having 1 to 3 substituents selected from hydroxy group, a lower alkyl group and a phenyl-lower alkyl group includes the above mentioned heterocyclic groups having 1 to 3 sustituents selected from hydroxy group, a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, and a phenylalkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, 3-hydroxypyrrolidinyl, 2-hydroxypyrrolidinyl, 4-hydroxypiperidinyl, 3-hydroxypiperidinyl, 2-hydropiperidinyl, 3-hydroxypiperazinyl, 2-hydroxy - piperazinyl, 3-hydroxymorpholino, 2-hydroxymorpholino, 4-benzylpiperazinyl, 3-(2-phenylethyl)pyrrolidinyl, 2-(3-phenylpropyl)pyrrolidinyl, 4-(4-pheny
- the amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group includes an amino group having optionally 1 to 2 substituents selected from a straight chain or branched chain alkanoyl group having 1 to 6 carbon atoms and a phenylalkenylcarbonyl group wherein the alkenylcarbonyl moiety is a straight chain or branched chain alkenylcarbonyl group having 3 to 6 carbon atoms in the alkenylcarbonyl moiety, for example, amino, formylamino, acetylamino, propionylamino, butyrylamino, isobutyrylamino, pentanoylamino, t-butyl - carbonylamino, hexanoylamino, cinnamoylamino, 4-phenyl-3-butenoylamino, 4-phenyl-2-butenoylamino
- the amino group having optionally a lower alkanoyl substituent includes an amino group having optionally a substituent of a straight chain or branched chain alkanoyl group having 1 to 6 carbon atoms, for example, amino, formylamino, acetyamino, propionylamino, butyrylamino, isobutyryl- amino, pentanoylamino, tert-butylcarbonylamino, hexanoylamino, and the like.
- the alkylsufinyl group includes a straight chain or branched chain alkylsulfinyl group having 1 to 6 carbon atoms, for example, methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, butylsulfinyl, tert-butylsuifinyl, pentylsulfinyl, hexylsulfinyl, and the like.
- the lower alkylthio group includes a straight chain or branched chain alkylthio group having 1 to 6 carbon atoms, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, tert-butylthio, pentylthio, hexylthio, and the like.
- the lower alkylsulfonyl group includes a straight chain or branched chain alkylsulfonyl group having 1 to 6 carbon atoms, for example, methylsulfonyl, ethylsulfonyl, isopropylsulfonyl, butysulfonyl, tert-butysulfonyl, pentylsulfonyl, hexylsulfonyl, and the like.
- the lower alkanoyloxy group includes a straight chain or branched chain alkanoyloxy group having 1 to 6 carbon atoms, for example, formyloxy, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, pentanoyloxy, tert - butylcarbonyloxy, hexanoyloxy, and the like.
- the amino-substituted lower alkyl group having optionally a substituent selected from a lower alkylsulfonyl group and a lower alkanoyl group includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms which is substituted by an amino group having optionally 1 to 2 groups selected from a straight chain or branched chain alkylsulfonyl group having 1 to 6 carbon atoms and a straight chain or branched chain alkanoyl group having 1 to 6 carbon atoms, for example, aminomethyl, 2-aminoethyl, 1 - aminoethyl, 3-aminopropyl, 4-aminobutyl, 5-aminopentyl, 6-aminohexyl, 1 ,1 - dimethyl-2-aminoethyl, 2-methyl-3-aminopropyl, formylaminomethyl, 1-acetyl - aminoethyl, 2-propionylaminoethyl,
- the 1 ,3-dioxolanyl-substituted lower alkyl group having optionally a lower alkyl substituent includes a 1 ,3-dioxolanyl-substituted alkyl group wherein the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, which may optionally have 1 to 3 substituents of a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, (1 ,3-dioxolan-2-yl)methyl, 2-(1 ,3-dioxolan-4-yl)ethyl, 1-(1 ,3-dioxolan - 2-yl)ethyl, 3-(1 ,3-dioxolan-4-yl)propyl, 4-(1 ,3-dioxolan-2-yl)butyl, 2-(1 ,3 - dioxolan-2-
- the alkanoyl-substituted lower alkyl group includes an alkanoylalkyl group wherein the alkanoyl moiety is a straight chain or branched chain alkanoyl group having 1 to 6 carbon atoms and the alkyl moiety is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, formylmethyl, acetylmethyl, 2-propionylethyl, 1-butyrylethyl, 3 - isobutyrylpropyl, 4-pentanoylbutyl, 5-hexanoylhexyl, 6-tert-butylcarbonylhexyl,
- the aminocarbonyl-substituted lower alkyl group which may optionally have a lower alkyl substituent includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms which is substituted by an aminocarbonyl having optionally 1 to 2 substituents of a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, aminocarbonylmethyl, 2-aminocarbonylethyl, 1-aminocarbonylethyl, 3 - aminocarbonylpropyl, 4-aminocarbonylbutyl, 5-aminocarbonylpentyl, 6 - aminocarbonylhexyl, 1 ,1 -dimethyl-2-aminocarbonylethyl, 2-methyl-3-amino - carbonylpropyl, methylaminocarbonylmethyl, 1 -ethylaminocarbonylethyl, 2 - propylaminocarbonylethyl, 3-isopropyla
- the lower alkoxycarbonyl-substituted lower alkenyl group includes a straight chain or branched chain alkenyl group having 2 to 6 carbon atoms which is substituted by a straight chain or branched chain alkoxy - carbonyl group having 1 to 6 carbon atoms in the alkoxy moiety, for example, 2 ⁇ methoxycarbonylvinyl, 2-ethoxycarbony vinyl, 3-propoxycarbonylallyl, 4-butoxy - carbonyl-2-butenyl, 4-pentyloxycarbonyl-3-butenyl, 3-hexyloxycarbonyl-1 - methylallyl, 5-isopropoxycarbonyl-2-pentenyl, 6-tert-butoxycarbonyl-2-hexenyl, and the like.
- the aminocarbonyl-substituted lower alkenyl group which may optionally have a lower alkyl substituent includes a straight chain or branched chain alkenyl group having 2 to 6 carbon atoms which is substitued by an aminocarbonyl group having optinally have 1 to 2 substituents of a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, 2 aminocarbonylvinyl, 3-aminocarbonylallyl, 4-aminocarbonyl-2-butenyl, 4 - aminocarbonyl-3-butenyl, 3-aminocarbonyl-1 -methylallyl, 5-aminocarbonyl-2 - pentenyl, 6-aminocarbonyl-2-hexenyl, 2-methylaminocarbonylvinyl, 3-ethyl - aminocarbonylallyl, 4-propylaminocarbonyl-2-butenyl, 4-isopropylamino - carbonyl-3-butenyl
- the carboxy-substituted lower alkenyl group includes a straight chain or branched chain alkenyl group having 2 to 6 carbon atoms, for example, 2-carboxyvinyl, 3-carboxyallyl, 4-carboxy-2-butenyl, 4-carboxy-3 - butenyl, 3-carboxy-1 -methylallyl, 5-carboxy-2-pentenyl, 6-carboxy-2-hexenyl, and the like.
- the aminocarbonyl group having optionally a lower alkyl substituent includes an aminocarbonyl group which may optionally have 1 to 2 substituents of a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, aminocarbonyl, methylaminocarbonyl, ethyl - aminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butyl- aminocarbonyl, tert-butylaminocarbonyl, pentylaminocarbonyl, hexyl - aminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dipropyl - aminocarbonyl, dibutylaminocarbonyl, dipentylaminocarbonyl, dihexyl - aminocarbonyl, N-methyl-N-ethylaminocarbonyl, N-ethyl-N-propylamino - carbonyl, N-methyl-N
- the phenylsulfonyl group having optionally a lower alkyl substituent includes a phenylsulfonyl group having optionally 1 to 3 substituents of a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, phenylsulfonyl, 2-methyl phenylsulfonyl, 3 - methylphenylsulfonyl, 4-methylphenylsulfonyl, 2-ethylphenylsulfonyl, 3 - ethylphenylsulfonyl, 4-ethylphenylsulfonyl, 3-isopropylphenylsulfonyl, 4 - hexylphenylsulfonyl, 3,4-dimethylphenylsulfonyl, 2,5-dimethylphenylsulfonyl, 3,4,5-trimethylphenylsulfonyl, and the
- the phenyl-lower alkenyl group includes a phenylalkenyl group wherein the alkenyl moiety is a straight chain or branched chain alkenyl group having 2 to 6 carbon atoms, for example, styryl, cinnamyl, 4-phenyl-3-butenyl, 4 phenyl-2-butenyl, 5-phenyl-4-pentenyl, 5-phenyl-3-pentenyl, 5-phenyl-2 - pentenyl, 6-phenyl-5-hexenyl, 6-phenyl-4-hexenyl, 6-phenyl-3-hexenyl, 6 - phenyl-2-hexenyl, 2-methyl-4-phenyl-3-butenyl, 2-methyl-cinnamyl, 1 -methyl - cinnamyl, and the like.
- the benzoyi group which may optionally have 1 to 3 substituents selected from a lower alkoxy group, a halogen atom, an amino group having optionally a lower alkanoyl substituent, and hydroxy group on the phenyl moiety includes a benzoyi group which may optinally have 1 to 3 substituents selected from a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, a halogen atom, an amino group having optionally a straight chain or branched chain alkanoyl substituent having 1 to 6 carbon atoms and hydroxy group on the phenyl moiety, for example, benzoyi, 2-chlorobenzoyl, 3 - chlorobenzoyl, 4-chlorobenzoyl, 2-fluorobenzoyl, 3-fluorobenzoyl, 4-fluoro - benzoyi, 2-bromobenzoyl, 3-bromobenzoyl, 4-bromobenzoyl, 2-iodo
- the amino-substituted lower alkanoyl group having optionally a lower alkanoyl substituent includes a straight chain or branched chain alkanoyl group having 2 to 6 carbon atoms which is substitued by an amino group having optionally 1 to 2 substituents of a straight chain or branched chain alkanoyl group having 1 to 6 carbon atoms, for example, 2-aminoacetyl, 3 - aminopropionyl, 2-aminopropionyl, 4-aminobutyryl, 5-aminopentanoyl, 6 - aminohexanoyl, 2,2-dimethyl-3-aminopropionyl, 2-methyl-3-aminopropionyl, 2 - acetylaminoacetyl, 2-acetylaminopropionyl, 3-propionylaminopropionyl, 3 - isopropionylaminopropionyl, 4-butyrylaminobutyryl, 5-pentanoyla
- the amino-substituted sulfonyl group having optionally a lower alkyl substituent includes an aminosulfonyl group which may optionally have 1 to 2 substituents of a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, aminosulfonyl, methylaminosulfonyl, ethylamino - sulfonyl, propylaminosulfonyl, isopropylaminosulfonyl, butylaminosulfonyl, tert - butylaminosulfonyl, pentylaminosulfonyl, hexylaminosulfonyl, dimethylamino - sulfonyl, diethylaminosulfonyl, dipropylaminosulfonyl, dibutylaminosulfonyl, dibutylaminosulfonyl, dipentylaminos
- the lower alkeneldioxy group includes a straight chain or branched chain alkylenedioxy group having 1 to 4 carbon atoms, for example, methylenedioxy, ethylenedioxy, trimethylenedioxy, tetramethylenendioxy, and the like.
- the phenyl group having optionlly a lower alkoxy substituent includes a phenyl group which may optionally have 1 to 3 substituents of a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms, for example, phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2 - ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 4-isopropoxyphenyl, 4-pentyl - oxyphenyl, 2,4-dimethoxyphenyl, 4-hexyloxyphenyl, 3-ethoxy-4-methoxy - phenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,4-diethoxyphenyl, 2,5 - dimethoxyphenyl, 2,6-dimethoxyphenyl, 3,5-dimethoxyphenyl, 3,4-dipentyloxy - phen
- the 2,3-dihydro-1 H-indenyl-substituted lower alkyl group which may optionall have a substituent selected from oxo group, hydroxy group and silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1H-indenyl ring includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms which is substituted by a 2,3-dihydro-1 H-indenyl group having optionally 1 to 3 substituents selected from oxo group, hydroxy group and a silyloxy group having 3 substituents of a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, for example, (2,3-dihydro-1 H-inden-2-yl) - methyl, 2-(2,3-dihydro-1 H-inden-1 -yl)ethyl, 1 -(2,3-dihydro-1 H-inden-3-yl)ethy
- the silyloxy group having a lower alkyl substituent includes a silyloxy group being substituted by three straight chain or branched chain alkyl groups having 1 to 6 carbon atoms, for example, trimethylsilyloxy, triethyl - silyloxy, triisopropylsilyloxy, tributylsilyloxy, tri-tert-butylsilyloxy, tripentylsilyloxy, trihexylsilyloxy, dimethyl, tert-butylsilyloxy, and the like.
- the phenyl group having optionally a substituent selected from a lower alkoxy group and a halogen atom on the phenyl ring includes a phenyl group which may optionaly be substituted by 1 to 3 groups selected from a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms and a halogen atom, for example, phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4 - methoxyphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 4 - isopropoxyphenyl, 4-pentyloxyphenyl, 2,4-dimethoxyphenyl, 4-hexyloxyphenyl, 3,4-dimethoxyphenyl, 3-ethoxy-4-methoxyphenyl, 2,3-dimethoxyphenyl, 3,4 - diethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxy
- the saturated or unsaturated 5- to 6-membered heterocyclic group having 1 to 4 hetero atoms selected from nitrogen atom, oxygen atom and sulfur atom includes, for example, pyrrolidinyl, piperidinyl, piperazinyl, morpholino, pyridyl, thienyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, imidazolidinyl, pyrazolyl, imidazolyl, pyrazolidinyl, 1 ,3,4-oxadiazolyl, 1 ,2,4 - triazolyl, 1 ,2,3,4-tetrazolyl, 1 ,3,4-triazolyl, 1 ,2,4-oxadiazolyl, furyl, pyrrolinyl, oxazolyl, isoxazolyl, thiazolyl, thiazolidinyl, 1 ,2,3,5-oxathiadiazolyl,
- the lower alkyl group substitued by a 5- to 6-membered saturated or unsaturated heterocyclic group having 1 to 4 hetero atoms selected from nitrogen atom, oxygen atom and sulfur atom includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms which is substituted by the above mentioned heterocyclic group, for example, pyrrolidinylmethyl, 2 - piperidinylethyl, 3-piperazinylpropyl, 4-morpholinobutyl, (2-pyridyl)methyl, (3 - pyridyl)methyl, (2-thienyl)methyl, 2-(3-pyrazinyl)ethyl, 1-(2-pyrimidyl)ethyl, 3-(3 - pyridazinyl)propyl, 4-(2-pyrrolyl)butyl, 4-(4-imidazolidinyl)butyl, (2-imidazolyl)- methyl, (3-pyrazolyl)methyl, 2-(
- the lower alkenyl group substituted by a 5- to 14-membered saturated or unsaturated heteromonocylic, heterobicyclic or heterothcyclic group having 1 to 4 hetero atoms selected from nitrogen atom, oxygen atom and sulfur atom includes the above mentioned heterocyclic group-substituted alkenyl group wherein the alkenyl moiety is a straight chain or branched chain alkenyl group with 1 to 2 double bounds having 2 to 6 carbon atoms, for example, 2-benzofurylvinyl, 3-benzofuryl-2-propenyl, 4-benzofuryl-3-butenyl, 3 - benzofuryl-2-butenyl, 2-methyl-3-benzofuryl-2-propenyl, 5-benzofuryl-4 - petenyl, 5-benzofuryl-2-pentenyl, 4-benzofuryl-3-pentenyl, 6-benzofuryl-5 - hexenyl, 6-benzofuryl-4-hexenyl, 6-
- the phenyl-lower alkoxycarbonyl group includes a phenylalkoxy - carbonyl group wherein the alkoxycarbonyl moiety is a straight chain or branched chain alkoxycarbonyl group having 1 to 6 carbon atoms in the alkoxy moiety, for example, benzyloxycarbonyl, 2-phenylethoxycarbonyl, 1 -phenyl - ethoxycarbonyl, 3-phenylpropoxycarbonyl, 4-phenylbutoxycarbonyl, 5-phenyl - pentyloxycarbonyl, 6-phenylhexyloxycarbonyl, 1 ,1 -dimethyl-2-phenylethoxy - carbonyl, 2-methyl-3-phenylpropoxycarbonyl, and the like.
- the lower alkoxycarbonyloxy-substituted lower alkyl group includes a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, which is substituted by alkoxycarbonyloxy group wherein the alkoxy moiety is a a straight chain or branched chain alkoxy group having 1 to 6 carbon atoms , for example, methoxycarbonyloxymethyl, ethoxycarbonyloxy - methyl, 2-ethoxycarbonyloxyethyl, 1 -ethoxycarbonyloxyethyl, 3-methoxy - carbonyloxypropyl, 4-ethoxycarbonyloxybutyl, 6-propoxycarbonyloxyhexyl, 5 - isopropoxycarbonyloxypentyl, 1 ,1 -dimethyl-2-butoxycarbonyloxyethyl, 2-methyl • 3-tert-butoxycarbonyloxypropyl, 2-pentyloxycarbonyloxyethyl, hex
- the benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring includes a straight chain or branched chain alkyl group having 1 to 6 carbon atom, which is substituted by a benzoyi group wherein the phenyl ring may optionally have 1 to 3 halogen substituents, for example, benzoylmethyl.
- the amino group having optionally a lower alkanoyl substituent includes an amino group which may optionally have a substituent of a straight chain or branched chain alkanoyl group having 1 to 6 carbon atoms, for example, amino, formylamino, acetylamino, propionylamino, butyrylamino, isobutyrylamino, pentanoylamino, t-butylcarbonylamino, hexanoylamino, and the like.
- the present invention specifically includes the following compounds.
- R 1 , R 3 , R 4 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a lower alkyl group
- R 4 is a phenylsulfinyl-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a lower alkyl group
- R 4 is a 2,3-dihydro-1 H-indenyl group-substituted lower alkyl group which may optionally have a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro - 1 H-indenyl ring
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkenyl group, R 2 is hydrogen atom, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are the same as defined above), a lower alkenyloxy group, nitro
- R 1 is a halogen atom or a lower alkyl group
- R 2 is hydrogen atom
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a phenylthio-substitued lower alkyl group which may optinally have a lower alkoxy substituent on the phenyl moiety
- m, n, and r are the same as defined above, or a salt thereof.
- R 6 A quinoxaline derivative of the formula (1), wherein R 1 is a halogen atom or a lower alkyl group, R 2 is hydrogen atom, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is hydrogen atom, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula: -A 5 -CR 42 R 3 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are the same as defined above
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a 2,3 - dihydro-1 H-indenyl group-substituted lower alkyl group which may optionally have a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring
- m, n and r are the same as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a group of the formula:
- R is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a group of the formula:
- R 1 is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4 -CO-NR 4 0R 41 (in which A 4 , R 4 ° and R 41 are the same as defined above), a lower alkeny
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is a morpholino-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenyl - carbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are the same
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is a morpholino-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenylsulfonyl - substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety, and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is a morpholino-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is a morpholino-substituted lower alkyl group, R 3 and R 4 combine together with the nitrogen atom to form 1 ,2,3,4 - tetrahydroisoquinolyl group which may optionally have a lower alkoxy group), and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenyl - carbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a lower alkenyl group, and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenylsulfinyl - substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula: -A ⁇ -CR ⁇ R ⁇ R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and m, n and r are the same as defined above, or a salt thereof.
- R 2 , m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is hydrogen atom, R 3 is a lower alkyl group, R 4 is a naphthyl-lower alkyl group, and R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 is hydrogen atom
- R 3 is hydrogen atom
- R 4 is a phenylthio-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety
- R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 is hydrogen atom
- R 3 is a lower alkyl group
- R 4 is a phenylsulfonyl-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety
- R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group and R 2 , R 3 , R 4 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a phenyl - lower alkoxycarbonyl group and R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl ring selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 4 are the same as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent, and
- R 3 is a lower alkanoyloxy-substituted lower alkyl group and R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl ring selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenyl - carbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -0-A 4 -CO-NR 4 OR 4 1 (in which A 4 , R 40 and R 41 are the same as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 3 is a phenyl - lower alkoxycarbonyl group, R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 3 is a lower alkanoyloxy-substituted lower alkyl group, R 4 is a group of the formula: -A 5 -CR 4 R 43 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 41 (in which A 4 , R 40 and R 41 are the same as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent, and R 1 , R 3 , R 4 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a lower alkoxy - lower alkyl group
- R 4 is a phenylsulfinyl-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 42 , R 43 and R 44 are the same as defined above), and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a lower alkoxy-lower alkyl group
- R 4 is a 2,3-dihydro-1 H-indenyl group-substituted lower alkyl group which may optionally have a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a lower alkoxycarbonyloxy-substituted lower alkyl group
- R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenyl - calbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are the same as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally
- R 1 , R 2 , m, n and r are the same as the same, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 3 is a lower alkoxycarbonyloxy-substituted lower alkyl group, R 4 is a cycloalkyl-lower alkyl group, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a lower alkoxycarbonyloxy-substituted lower alkyl group
- R 4 is a cycloalkyl-lower alkyl group
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a lowe alkanoyl-substituted lower alkyl group
- R 4 is a phenylthio-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a lower alkoxycarbonyloxy-substituted lower alkyl group
- R 4 is a phenoxy-substituted lower alkyl group
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a group of the formula: -E-NR 52 R 53 (in which E, R 52 and R 53 are the same as defined above),
- R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy - substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are the same as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group
- R 3 is a group of the formula: -E-NR 52 R 53 (in which E, R 52 and R 53 are the same as defined above), R 4 is a phenylthio-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a group of the formula: -E-NR 52 R 53 (in which E, R 52 and R 53 are the same as defined above), R 4 is a phenylsulfinyl-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a group of the formula: -E-NR 52 R 53 (in which E, R 52 and R 53 are the same as defined above), R 4 is a phenylsulfonyl-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a benzoyl-substituted lower alkyl group which may optionally have a halogen substituent on the phenyl ring
- R 4 is a phenoxy-substituted lower alkyl group
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a group of the formula: -E-NR 52 R 53 (in which E, R 52 and R 53 are the same as defined above), R 4 is a phenoxy-substituted lower alkyl group, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 3 is a benzoyl-substituted lower alkyl group which may optionally have a halogen substituent on the phenyl ring, R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a group of the formula: -E-NR 52 R 53 (in which E, R 52 and R 53 are the same as defined above)
- R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above)
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a benzoyl-substituted lower alkyl group which may optionally have a halogen substituent on the phenyl ring
- R 4 is a 2, 3-dihydro-1 H-indenyl group-substituted lower alkyl group which may optionally have a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a group of the formula: -E-NR 5 R 53 (in which E, R 52 and R 53 are the same as defined above), R 4 is a 2, 3-dihydro-1 H-indenyl group-substituted lower alkyl group which may optionally have a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro -
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a benzoyl-substituted lower alkyl group which may optionally have a halogen substituent on the phenyl ring
- R 4 is a group of the formula:
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 4 is a group of the formula:
- R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl - lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are the same as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent, and R 1 , R 3 ,
- R 4 , m, n and r are the same as defined above, or a salt thereof.
- R 4 is a lower alkenyl group, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a group of the formula:
- R 4 is a cycloalkyl-lower alkyl group, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 4 is a naphthyl-lower alkyl group, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a group of the formula:
- R 4 is a phenylthio - substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety, and R 1 , R 2 , m, n and r are the same as defined above, or a sa
- R 3 is a group of the formula:
- R 4 is a phenylsulfinyl - substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 3 is a group of the formula: — 54
- R 4 is a phenylsulfonyl - substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 4 is a phenoxy - substituted lower alkyl group, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 4 is a group of the formula:
- R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 4 is a 2,3-dihydro-1 H - indenyl group-substituted lower alkyl group which may optionally have a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring, and R 1 , R 2 , m, n and r are the same as defined above, or a salt thereof.
- R 4 is a group of the formula:
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a lower alkenyl group
- m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a cycloalkyl - lower alkyl group
- m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is hydrogen atom, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenylthio - substitued lower alkyl group which may optinally have a lower alkoxy substituent on the phenyl moiety, and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is hydrogen atom, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenylsulfinyl-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety, and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a phenylsulfonyl-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety
- m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is hydrogen atom, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is a lower alkyl group having optionally a halogen substituent, R 3 is hydrogen atom or a lower alkyl group, R 4 is a naphthyl-lower alkyl group, and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is a lower alkyl group having optionally a halogen substituent, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenylsulfonyl-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety, and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is a lower alkyl group having optionally a halogen substituent, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenoxy-substituted lower alkyl group, and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is a lower alkyl group having optionally a halogen substituent, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is a lower alkyl group having optionally a halogen substituent, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is phenyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenyl - carbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is phenyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a cycloalkyl-lower alkyl group, and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is phenyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a phenylsulfonyl - substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety
- m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is phenyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is phenyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is phenyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a 2,3-dihydro-1 H - indenyl group-substituted lower alkyl group which may optionally have a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring
- m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is phenyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula:
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is phenyl group
- R 3 and R 4 combine together with the nitrogen atom to form 1 ,2,3,4 - tetrahydroisoquinolyl group which may optionally have a lower alkoxy group)
- m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a group of the formula:
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy - substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is a morpholino-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a lower alkenyl group, and m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is a morpholino-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a naphthyl-lower alkyl group, and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a phenylthio-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety
- m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is a morpholino-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenylsulfinyl-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (A 5 , R 42 , R 43 and R 44 are the same as defined above), and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a 2,3-dihydro-1 H-indenyl group-substituted lower alkyl group which may optionally have a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro - 1 H-indenyl ring
- m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is a morpholino-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenyl-lower alkenyl group which may optionally have a substituent on the phenyl moiety selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy - substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole ring, hydroxy group, a group of the formula: -O-A 4 -
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a cycloalkyl-lower alkyl group, and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a phenylthio-substituted lower alkyl group which may optionally have a lower alkoxy substituent on the phenyl moiety
- m, n and r are the same as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a phenoxy-substituted lower alkyl group, and m, n and r are the same as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is hydrogen atom or a lower alkyl group
- R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent or an aminocarbonyl group having optionally a lower alkyl substituent, R 2 is an imidazolyl-substituted lower alkyl group, R 3 is hydrogen atom or a lower alkyl group, R 4 is a group of the formula:
- R 1 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula: _ A R 54
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 5 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group. of the formula: (in which R 54 is hydrogen atom or a lower alkyl group and A is the same as defined
- R 1 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 4 is a phenyl-lower alkenyl group having optionally a substituent selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole moiety, hydroxy group, a group of the formula: -O-A -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent on the phenyl moiety, and R 2 , m, n, and r are as
- R 1 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a lower alkenyl group; and
- R 2 , m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a cycloalkyl-lower alkyl group; and
- R 2 , m, n, and r are as defined above, or a salt thereof.
- R 1 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a naphthyl-lower alkyl group; and
- R 2 , m, n, and r are as defined above, or a salt thereof.
- R 1 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 5 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylthio-substituted lower alkyl group having optionally a lower alkoxy-substituent on the phenyl moiety; and
- R 2 , m, n, and r are as defined above, or a salt thereof.
- R 1 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula: _ A R 54
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfinyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety; and
- R 2 , m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfonyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety; and
- R 2 , m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenoxy-substituted lower alkyl group; and
- R 2 , m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula: _A R 54
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a group of the formula: -As-CR ⁇ R ⁇ R 44 (in which A 5 ,
- R 42 , R 43 and R 44 are as defined above); and R 2 , m, n, and r are as defined above, or a salt thereof.
- R 1 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula: — A R 54
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a 2,3-dihydro-1 H-indenyl-substituted lower alkyl group having optionally a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring
- R 2 , m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a halogen atom or a lower alkyl group
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having otionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 4 is a phenyl-lower alkenyl group having optionally a substituent selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole moiety, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent on the phenyl moiety, and m, n, and r are as defined above,
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is hydrogen atom; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a lower alkenyl group, and m, n, and r are as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is hydrogen atom; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a naphthyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula: (in which R
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is hydrogen atom; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfinyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfonyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenoxy-substituted lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxy - carbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is hydrogen atom; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxy - carbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R53 are as defined above), or a group of the formula:
- R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (in which A 5 , R 42 , R 43 and R 44 are as defined above), and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a 2,3-dihydro-1 H-indenyl-substituted lower alkyl group having optionally a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 4 is a phenyl-lower alkenyl group having optionally a substituent selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole moiety, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent on the phenyl moiety, and m, n, and r are as defined above,
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E - N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a lower alkenyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above),
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a cycloalkyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above),
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above),
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylthio-substituted lower alkyl group having optionally a lower alkoxy-substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfinyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above),
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfonyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenoxy-substituted lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above),
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above),
- R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (in which A 5 , R 42 , R 43 and R 44 are as defined above), and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a 2,3-dihydro-1 H-indenyl-substituted lower alkyl group having optionally a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring
- m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 4 is a phenyl-lower alkenyl group having optionally a substituent selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole moiety, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent on the phenyl moiety, and m, n, and r are as defined above,
- R 1 is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 4 is a lower alkenyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a hal
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a cycloalkyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 5 )(R 53 ) (in which
- R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a naphthyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is phenyl group; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 5 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula: (in
- R 1 is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfinyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is phenyl group; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfonyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is phenyl group; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenoxy-substituted lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (in which A 5 , R 42 , R 43 and R 44 are as defined above), and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is phenyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined above), or a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a 2,3-dihydro-1 H-indenyl-substituted lower alkyl group having optionally a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 4 is a phenyl-lower alkenyl group having optionally a substituent selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole moiety, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent on the phenyl moiety, and m, n, and r are as defined above,
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a lower alkenyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxy - carbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substit
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a cycloalkyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a naphthyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylthio-substituted lower alkyl group having optionally a lower alkoxy-substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 5 )(R 53 ) (in which E, R 52 and R 53 are as defined above
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfinyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfonyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenoxy-substituted lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a halogen atom or a lower alkyl group
- R 2 is a morpholino-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is a morpholino-substituted lower alkyl group; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 5 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a 2,3-dihydro-1 H-indenyl-substituted lower alkyl group having optionally a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 4 is a phenyl-lower alkenyl group having optionally a substituent selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole moiety, hydroxy group, a group of the formula: -O-A -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent on the phenyl moiety, and m, n, and r are as defined above, or
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is an imidazolyl-substituted lower alkyl group; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a lower alkenyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a cycloalkyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- a quinoxaline derivative of the formula (1) wherein R 1 is a halogen atom or a lower alkyl group; R 2 is an imidazolyl-substituted lower alkyl group; R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as
- R 1 is a halogen atom or a lower alkyl group
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 )
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylthio-substituted lower alkyl group having optionally a lower alkoxy-substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 5 )(R 53 ) (in which E, R 52 and R 53 are as
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfinyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfonyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenoxy-substituted lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (in which A 5 , R 42 , R 43 and R 44 are as defined above), and m, n, and r are as defined above, or a salt thereof.
- R 1 is a halogen atom or a lower alkyl group
- R 2 is an imidazolyl-substituted lower alkyl group
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy - lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which E, R 52 and R 53 are as defined
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a 2,3-dihydro-1 H-indenyl-substituted lower alkyl group having optionally a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2,3-dihydro-1 H-indenyl ring, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (
- R 4 is a phenyl-lower alkenyl group having optionally a substituent selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole moiety, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent on the phenyl moiety, and m, n, and r are as defined above,
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a lower alkenyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a cycloalkyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a naphthyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylthio-substituted lower alkyl group having optionally a lower alkoxy-substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfinyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfonyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenoxy-substituted lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in
- R 4 is a group of the formula: -A 5 -CR 42 R 43 R 44 (in which A 5 , R 42 , R 43 and R 44 are as defined above), and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is hydrogen atom
- R 3 is a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl - substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E-N(R 52 )(R 53 ) (in which
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above
- R 4 is a 2,3-dihydro-1H-indenyl-substituted lower alkyl group having optionally a substituent selected from oxo group, hydroxy group and a silyloxy group having a lower alkyl substituent on the 2, 3-dihydro-1 H-indenyl ring, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy - carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxy - carbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxycarbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyl-substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy - carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -
- R 4 is a phenyl-lower alkenyl group having optionally a substituent selected from a lower alkoxy group, a halogen atom, an amino group having optionally a substituent selected from a lower alkanoyl group and a phenyl-lower alkenylcarbonyl group, a lower alkoxy-substituted lower alkoxy group, a tetrazolyl group having optionally a lower alkyl substituent on the tetrazole moiety, hydroxy group, a group of the formula: -O-A 4 -CO-NR 40 R 41 (in which A 4 , R 40 and R 41 are as defined above), a lower alkenyloxy group, nitro group and a lower alkyl group having optionally a halogen substituent on the phenyl moiety, and m, n, and r are as defined above,
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy - carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a lower alkenyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy - carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a cycloalkyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy - carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a naphthyl-lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy- carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -E
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylthio-substituted lower alkyl group having optionally a lower alkoxy-substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy - carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfinyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy - carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenylsulfonyl-substituted lower alkyl group having optionally a lower alkoxy substituent on the phenyl moiety, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy - carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula:
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a phenoxy-substituted lower alkyl group, and m, n, and r are as defined above, or a salt thereof.
- R 1 is a lower alkoxy group, an amino group having optionally a lower alkyl substituent, or an aminocarbonyl group having optionally a lower alkyl substituent
- R 2 is a lower alkyl group having optionally a halogen substituent
- R 3 is a lower alkanoyloxy - substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxy - carbonyloxy-substituted lower alkyl group, a phenyl-lower alkoxycarbonyl group, a lower alkanoyl group, a lower alkoxy-lower alkyl group, a phenoxy - carbonyl group, a lower alkanoyl-substituted lower alkyl group, a benzoyi - substituted lower alkyl group having optionally a halogen substituent on the phenyl ring, a group of the formula: -
- R 54 is hydrogen atom or a lower alkyl group and A is the same as defined above);
- R 4 is a group of the formula:
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- Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
- Public Health (AREA)
- 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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Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24114093 | 1993-09-28 | ||
JP241140/93 | 1993-09-28 | ||
JP11463994 | 1994-04-28 | ||
JP114639/94 | 1994-04-28 | ||
PCT/JP1994/001559 WO1995009159A1 (en) | 1993-09-28 | 1994-09-22 | Quinoxaline derivative as antidiabetic agent |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0670831A1 true EP0670831A1 (en) | 1995-09-13 |
Family
ID=26453355
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94927085A Withdrawn EP0670831A1 (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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JP2941950B2 (ja) * | 1994-11-23 | 1999-08-30 | ニューロゲン コーポレイション | 或る種の4−アミノメチル−2−置換イミダゾール誘導体および2−アミノメチル−4−置換イミダゾール誘導体;新規な種類のドーパミン リセプタ亜型特異性リガンド |
US7008950B1 (en) | 1997-06-05 | 2006-03-07 | Takeda Chemical Industries, Ltd. | Benzofurans 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 |
OA11749A (en) | 1999-01-11 | 2005-07-19 | 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 |
CN1901917A (zh) * | 2004-01-06 | 2007-01-24 | 詹森药业有限公司 | 作为糖原磷酸化酶抑制剂用于治疗糖尿病和肥胖症的(3-氧代-3,4-二氢-喹喔啉-2-基-氨基)-苯甲酰胺衍生物和相关化合物 |
EP2479168B1 (en) | 2004-02-25 | 2014-04-09 | Eli Lilly And Company | 6-Substituted 2,3,4,5-Tetrahydro-1H-Benzo [d]Azepines as 5-HT2C Receptor Agonists |
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 |
US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
PL1786790T3 (pl) * | 2004-07-26 | 2009-10-30 | Lilly Co Eli | Pochodne oksazolu jako środki receptora histaminowego H3, ich wytwarzanie i terapeutyczne zastosowanie |
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 |
EP2065377B1 (en) | 2006-09-21 | 2011-11-23 | Eisai R&D Management 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 |
US7964732B2 (en) | 2006-11-17 | 2011-06-21 | Pfizer Inc. | Substituted bicyclocarboxyamide compounds |
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 |
CN101622251B (zh) | 2007-04-27 | 2012-07-04 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物的盐或其结晶 |
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 |
US9181182B2 (en) | 2008-10-17 | 2015-11-10 | Akaal Pharma Pty Ltd | S1P receptors modulators |
CN102186845B (zh) * | 2008-10-17 | 2016-09-07 | 阿卡制药有限公司 | S1p受体调节剂以及它们的用途 |
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 |
WO2010050445A1 (ja) | 2008-10-27 | 2010-05-06 | 武田薬品工業株式会社 | 二環性化合物 |
DK3016946T3 (da) | 2013-07-03 | 2023-01-09 | Karyopharm Therapeutics Inc | Substituerede benzofuranyl- og benzoxazolylforbindelser og anvendelser deraf |
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 |
WO2022169921A1 (en) * | 2021-02-04 | 2022-08-11 | Bristol-Myers Squibb Company | Benzofuran compounds as sting agonists |
AU2022292554A1 (en) | 2021-06-14 | 2024-01-04 | Scorpion Therapeutics, Inc. | Urea derivatives which can be used to treat cancer |
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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 |
AU9049391A (en) * | 1990-12-20 | 1992-07-22 | Warner-Lambert Company | 2-acylamido derivatives of 3,4-dihydro-3-oxo-quinoxaline having pharmaceutical activity |
NO179904C (no) * | 1992-09-04 | 1997-01-08 | Takeda Chemical Industries Ltd | Kondenserte heterocykliske forbindelser og deres anvendelse |
-
1994
- 1994-09-22 EP EP94927085A patent/EP0670831A1/en not_active Withdrawn
- 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 AU AU76660/94A patent/AU674613B2/en not_active Ceased
- 1994-09-22 CN CN94190719A patent/CN1114834A/zh active Pending
- 1994-09-22 CA CA002150345A patent/CA2150345A1/en not_active Abandoned
- 1994-09-23 TW TW083108792A patent/TW284760B/zh active
Non-Patent Citations (1)
Title |
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See references of WO9509159A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO1995009159A1 (en) | 1995-04-06 |
KR100196356B1 (ko) | 1999-06-15 |
CN1114834A (zh) | 1996-01-10 |
TW284760B (ko) | 1996-09-01 |
AU674613B2 (en) | 1997-01-02 |
CA2150345A1 (en) | 1995-04-06 |
AU7666094A (en) | 1995-04-18 |
KR950704269A (ko) | 1995-11-17 |
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