CN1114834A - 抗糖尿病剂 - Google Patents
抗糖尿病剂 Download PDFInfo
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- CN1114834A CN1114834A CN94190719A CN94190719A CN1114834A CN 1114834 A CN1114834 A CN 1114834A CN 94190719 A CN94190719 A CN 94190719A CN 94190719 A CN94190719 A CN 94190719A CN 1114834 A CN1114834 A CN 1114834A
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- 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 439
- 150000003839 salts Chemical class 0.000 claims abstract description 562
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 1681
- -1 nitro, hydroxy Chemical group 0.000 claims description 1260
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 421
- 125000003545 alkoxy group Chemical group 0.000 claims description 365
- 125000001589 carboacyl group Chemical group 0.000 claims description 256
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 254
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 243
- 125000005843 halogen group Chemical group 0.000 claims description 228
- 150000002367 halogens Chemical class 0.000 claims description 195
- 125000001424 substituent group Chemical group 0.000 claims description 184
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 133
- 125000003342 alkenyl group Chemical group 0.000 claims description 127
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 110
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 102
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 101
- 125000004423 acyloxy group Chemical group 0.000 claims description 98
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 94
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 84
- 125000000623 heterocyclic group Chemical group 0.000 claims description 63
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 62
- 229910052757 nitrogen Inorganic materials 0.000 claims description 61
- 125000004043 oxo group Chemical group O=* 0.000 claims description 58
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 57
- 125000002757 morpholinyl group Chemical group 0.000 claims description 56
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 53
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 51
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 51
- 125000002947 alkylene group Chemical group 0.000 claims description 45
- 125000004469 siloxy group Chemical class [SiH3]O* 0.000 claims description 42
- 150000003536 tetrazoles Chemical class 0.000 claims description 38
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 34
- 125000003277 amino group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000002883 imidazolyl group Chemical group 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 150000003254 radicals Chemical class 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 15
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 6
- 208000032825 Ring chromosome 2 syndrome Diseases 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000499 benzofuranyl 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
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-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
- 150000003252 quinoxalines Chemical class 0.000 claims 32
- 238000003780 insertion Methods 0.000 claims 4
- 230000037431 insertion Effects 0.000 claims 4
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 3
- 239000007800 oxidant agent Substances 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-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
- JONMQUXKCAHPLX-UHFFFAOYSA-N 3-methyl-n-[[3-methyl-7-(trifluoromethyl)-1-benzofuran-2-yl]methyl]-4-oxidoquinoxalin-4-ium-2-carboxamide Chemical compound O1C2=C(C(F)(F)F)C=CC=C2C(C)=C1CNC(=O)C1=NC2=CC=CC=C2[N+]([O-])=C1C JONMQUXKCAHPLX-UHFFFAOYSA-N 0.000 claims 1
- HHDZOKHUXHMLSH-UHFFFAOYSA-N CC(=CCNC(=O)c1nc2ccccc2[n+]([O-])c1C)c1cc2cc(F)cc(F)c2o1 Chemical compound CC(=CCNC(=O)c1nc2ccccc2[n+]([O-])c1C)c1cc2cc(F)cc(F)c2o1 HHDZOKHUXHMLSH-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
- 125000000033 alkoxyamino group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 1
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 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
- 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
- 229940037201 oris Drugs 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 description 147
- 239000001257 hydrogen Substances 0.000 description 146
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 145
- 125000004432 carbon atom Chemical group C* 0.000 description 109
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 29
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 18
- 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 14
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229940125396 insulin Drugs 0.000 description 7
- 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 6
- 239000008103 glucose Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 5
- 230000002218 hypoglycaemic effect Effects 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
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- 239000007952 growth promoter Substances 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000003914 insulin secretion Effects 0.000 description 4
- 125000003386 piperidinyl group Chemical group 0.000 description 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 4
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- 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
- 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
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- 238000010521 absorption reaction Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 description 3
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- 125000002071 phenylalkoxy group Chemical group 0.000 description 3
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- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 3
- VRYALKFFQXWPIH-PBXRRBTRSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-PBXRRBTRSA-N 0.000 description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 2
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- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 2
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- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
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- 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 2
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 230000001154 acute effect Effects 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
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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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
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- 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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Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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JP24114093 | 1993-09-28 | ||
JP241140/93 | 1993-09-28 | ||
JP114639/94 | 1994-04-28 | ||
JP11463994 | 1994-04-28 |
Publications (1)
Publication Number | Publication Date |
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CN1114834A true CN1114834A (zh) | 1996-01-10 |
Family
ID=26453355
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN94190719A Pending CN1114834A (zh) | 1993-09-28 | 1994-09-22 | 抗糖尿病剂 |
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) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
CN104086491A (zh) * | 2014-07-09 | 2014-10-08 | 广西师范大学 | 2,3-二取代喹喔啉衍生物的制备方法 |
Families Citing this family (33)
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EP0793653A1 (en) * | 1994-11-23 | 1997-09-10 | Neurogen Corporation | Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands |
CA2291026A1 (en) | 1997-06-05 | 1998-12-10 | Takeda Chemical Industries, Ltd. | Heterocyclic compounds, their production and use |
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 |
AU781711B2 (en) | 1999-01-11 | 2005-06-09 | Agouron Pharmaceuticals, Inc. | 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 |
DE602004007693T2 (de) * | 2004-01-06 | 2008-06-05 | Janssen Pharmaceutica N.V. | (3-oxo-3,4-dihydro-chinoxalin-2-yl-amino)-benzamid-derivate und verwandte verbindungen als glykogen-phosphorylase-hemmer zur behandlung von diabetes und adipositas |
EP1720836B1 (en) | 2004-02-25 | 2014-04-16 | 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 |
US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
US7205316B2 (en) | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
EP1786790B1 (en) * | 2004-07-26 | 2009-06-03 | Eli Lilly And Company | Oxazole derivatives as histamine h3 receptor agents, preparation and therapeutic uses |
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 |
WO2008035726A1 (fr) | 2006-09-21 | 2008-03-27 | Eisai R & D Management Co., Ltd. | Dérivé de pyridine substitué par un cycle hétéroaryle, et agent antifongique le comprenant |
ATE509925T1 (de) | 2006-11-17 | 2011-06-15 | Pfizer | Substituierte bicyclocarbonsäureamidverbindungen |
JPWO2008136279A1 (ja) | 2007-04-27 | 2010-07-29 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロ環置換ピリジン誘導体の塩またはその結晶 |
TW200841879A (en) | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
EP2344484B1 (en) | 2008-10-17 | 2016-06-08 | Akaal Pharma Pty Ltd | S1p receptors modulators and use thereof |
EP2344446A4 (en) | 2008-10-17 | 2012-04-04 | Akaal Pharma Pty Ltd | S1P RECEPTOR MODULATORS |
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 |
JP5535931B2 (ja) | 2008-10-27 | 2014-07-02 | 武田薬品工業株式会社 | 二環性化合物 |
CN105492437B (zh) | 2013-07-03 | 2018-05-11 | 卡尔约药物治疗公司 | 取代的苯并呋喃基和苯并噁唑基化合物及其用途 |
US10858347B2 (en) * | 2015-12-31 | 2020-12-08 | 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 |
IL309232A (en) | 2021-06-14 | 2024-02-01 | Scorpion Therapeutics Inc | History of urea which can be used to treat cancer |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
DE69315920T2 (de) * | 1992-09-04 | 1998-06-10 | Takeda Chemical Industries Ltd | Kondensierte heterozyklische Verbindungen, deren Herstellung und Verwendung |
-
1994
- 1994-09-22 CN CN94190719A patent/CN1114834A/zh active Pending
- 1994-09-22 EP EP94927085A patent/EP0670831A1/en not_active Withdrawn
- 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 WO PCT/JP1994/001559 patent/WO1995009159A1/en not_active Application Discontinuation
- 1994-09-22 CA CA002150345A patent/CA2150345A1/en not_active Abandoned
- 1994-09-23 TW TW083108792A patent/TW284760B/zh active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
CN104086491A (zh) * | 2014-07-09 | 2014-10-08 | 广西师范大学 | 2,3-二取代喹喔啉衍生物的制备方法 |
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 |
Also Published As
Publication number | Publication date |
---|---|
KR950704269A (ko) | 1995-11-17 |
WO1995009159A1 (en) | 1995-04-06 |
AU674613B2 (en) | 1997-01-02 |
TW284760B (ko) | 1996-09-01 |
EP0670831A1 (en) | 1995-09-13 |
KR100196356B1 (ko) | 1999-06-15 |
CA2150345A1 (en) | 1995-04-06 |
AU7666094A (en) | 1995-04-18 |
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