KR930002344A - 5-원 헤테로사이클릭 화합물, 이의 제조방법 및 이를 함유하는 약제학적 조성물 - Google Patents
5-원 헤테로사이클릭 화합물, 이의 제조방법 및 이를 함유하는 약제학적 조성물 Download PDFInfo
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- KR930002344A KR930002344A KR1019920013494A KR920013494A KR930002344A KR 930002344 A KR930002344 A KR 930002344A KR 1019920013494 A KR1019920013494 A KR 1019920013494A KR 920013494 A KR920013494 A KR 920013494A KR 930002344 A KR930002344 A KR 930002344A
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- 150000000565 5-membered heterocyclic compounds Chemical class 0.000 title claims 4
- 239000008194 pharmaceutical composition Substances 0.000 title claims 4
- 238000002360 preparation method Methods 0.000 title 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 57
- -1 alkylsulphenyl Chemical group 0.000 claims 51
- 150000001875 compounds Chemical class 0.000 claims 47
- 229910052757 nitrogen Inorganic materials 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000004432 carbon atom Chemical group C* 0.000 claims 22
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 17
- 229910052801 chlorine Inorganic materials 0.000 claims 17
- 239000000460 chlorine Substances 0.000 claims 16
- 125000003277 amino group Chemical group 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 15
- 229910052760 oxygen Inorganic materials 0.000 claims 15
- 239000001301 oxygen Substances 0.000 claims 15
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 14
- 150000001721 carbon Chemical group 0.000 claims 13
- 239000011737 fluorine Substances 0.000 claims 13
- 229910052731 fluorine Inorganic materials 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 11
- 125000004429 atom Chemical group 0.000 claims 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 10
- 125000002947 alkylene group Chemical group 0.000 claims 10
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 10
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 10
- 239000011593 sulfur Substances 0.000 claims 10
- 125000004450 alkenylene group Chemical group 0.000 claims 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 125000005550 pyrazinylene group Chemical group 0.000 claims 9
- 125000005576 pyrimidinylene group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004434 sulfur atom Chemical group 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000005551 pyridylene group Chemical group 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 7
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 7
- 125000001246 bromo group Chemical group Br* 0.000 claims 7
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 5
- 125000001589 carboacyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 230000000269 nucleophilic effect Effects 0.000 claims 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 5
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 claims 4
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 4
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims 4
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 3
- HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical compound O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 claims 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 3
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000005835 indanylene group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 150000007522 mineralic acids Chemical class 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 3
- 125000005558 triazinylene group Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical group C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims 2
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 claims 2
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims 1
- MUZIZEZCKKMZRT-UHFFFAOYSA-N 1,2-dithiolane Chemical compound C1CSSC1 MUZIZEZCKKMZRT-UHFFFAOYSA-N 0.000 claims 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
- DQLOTKZORORBPO-UHFFFAOYSA-N 1,3-dithiolane 1,1,3,3-tetraoxide Chemical compound O=S1(=O)CCS(=O)(=O)C1 DQLOTKZORORBPO-UHFFFAOYSA-N 0.000 claims 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- MPTKDOQUXZAHPJ-UHFFFAOYSA-N 2,3-dihydroindazole Chemical compound C1=CC=C2CN[N]C2=C1 MPTKDOQUXZAHPJ-UHFFFAOYSA-N 0.000 claims 1
- WURYWHAKEJHAOV-UHFFFAOYSA-N 2,5-dihydrothiophene Chemical compound C1SCC=C1 WURYWHAKEJHAOV-UHFFFAOYSA-N 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- XYTYTWRQDLUKCF-UHFFFAOYSA-N 2-[[5-[4-(4-carbamimidoylphenyl)phenyl]-1h-1,2,4-triazol-3-yl]sulfanyl]acetic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(C=2N=C(SCC(O)=O)NN=2)C=C1 XYTYTWRQDLUKCF-UHFFFAOYSA-N 0.000 claims 1
- AJENTUFGLPVHNS-UHFFFAOYSA-N 2-amino-3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(CC(N)C(O)=O)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 AJENTUFGLPVHNS-UHFFFAOYSA-N 0.000 claims 1
- WVRZZQKNIMPEID-UHFFFAOYSA-N 2-amino-3-[1-[6-[4-(aminomethyl)phenyl]pyridazin-3-yl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(CN)=CC=C1C1=CC=C(N2C=C(CC(N)C(O)=O)N=C2)N=N1 WVRZZQKNIMPEID-UHFFFAOYSA-N 0.000 claims 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
- HGMJGJDBRCZPNN-UHFFFAOYSA-N 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]-2-(dibenzylamino)propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(N2C=C(CC(N(CC=3C=CC=CC=3)CC=3C=CC=CC=3)C(O)=O)N=C2)N=N1 HGMJGJDBRCZPNN-UHFFFAOYSA-N 0.000 claims 1
- ZBJCVPFNYVAJQS-UHFFFAOYSA-N 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]-2-hydroxypropanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(N2C=C(CC(O)C(O)=O)N=C2)N=N1 ZBJCVPFNYVAJQS-UHFFFAOYSA-N 0.000 claims 1
- ZFJXQZDHZQNHNA-UHFFFAOYSA-N 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(N2C=C(CCC(O)=O)N=C2)N=N1 ZFJXQZDHZQNHNA-UHFFFAOYSA-N 0.000 claims 1
- LWMBAXOYBMILJM-UHFFFAOYSA-N 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]indol-3-yl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(N2C3=CC=CC=C3C(CCC(O)=O)=C2)N=N1 LWMBAXOYBMILJM-UHFFFAOYSA-N 0.000 claims 1
- RFSXIEAYLUHQNY-UHFFFAOYSA-N 3-[4-[4-(4-carbamimidoylphenyl)-1,3-thiazol-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CSC(C=2C=CC(CCC(O)=O)=CC=2)=N1 RFSXIEAYLUHQNY-UHFFFAOYSA-N 0.000 claims 1
- NGWOGPJKZVPROF-UHFFFAOYSA-N 3-[4-[4-(4-carbamimidoylphenyl)-1-methylimidazol-2-yl]phenyl]propanoic acid Chemical compound CN1C=C(C=2C=CC(=CC=2)C(N)=N)N=C1C1=CC=C(CCC(O)=O)C=C1 NGWOGPJKZVPROF-UHFFFAOYSA-N 0.000 claims 1
- FZEPOLLBQTYLDV-UHFFFAOYSA-N 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CNC(C=2C=CC(CCC(O)=O)=CC=2)=N1 FZEPOLLBQTYLDV-UHFFFAOYSA-N 0.000 claims 1
- AGKMJXCYUQOHIJ-UHFFFAOYSA-N 3-[4-[5-(4-carbamimidoylphenyl)tetrazol-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=NN(C=2C=CC(CCC(O)=O)=CC=2)N=N1 AGKMJXCYUQOHIJ-UHFFFAOYSA-N 0.000 claims 1
- GTMHMJIGXWJKNJ-UHFFFAOYSA-N 3-[5-[4-(4-carbamimidoylphenyl)phenyl]-1,3,4-thiadiazol-2-yl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(C=2SC(CCC(O)=O)=NN=2)C=C1 GTMHMJIGXWJKNJ-UHFFFAOYSA-N 0.000 claims 1
- CJPFYMPKJYWIAA-UHFFFAOYSA-N 3-[5-[4-(4-carbamimidoylphenyl)phenyl]tetrazol-2-yl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(C2=NN(CCC(O)=O)N=N2)C=C1 CJPFYMPKJYWIAA-UHFFFAOYSA-N 0.000 claims 1
- MOOGYWRPKHQBEK-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;1h-imidazole Chemical compound C1CN=CN1.C1=CNC=N1 MOOGYWRPKHQBEK-UHFFFAOYSA-N 0.000 claims 1
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
- 125000003713 acetylimino group Chemical group [H]C([H])([H])C(=O)N=[*] 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 238000010306 acid treatment Methods 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 1
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000008619 cell matrix interaction Effects 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 235000013601 eggs Nutrition 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- WJJXCNMWZQOQHE-UHFFFAOYSA-N methyl 2-amino-3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CC(N)C(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 WJJXCNMWZQOQHE-UHFFFAOYSA-N 0.000 claims 1
- HZVDGRHGPQHUDI-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]-2-hydroxypropanoate Chemical compound C1=NC(CC(O)C(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 HZVDGRHGPQHUDI-UHFFFAOYSA-N 0.000 claims 1
- JICXRCOSKQBGPZ-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 JICXRCOSKQBGPZ-UHFFFAOYSA-N 0.000 claims 1
- LIOPJDZQFZLCEL-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1-methylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1C LIOPJDZQFZLCEL-UHFFFAOYSA-N 0.000 claims 1
- HAOIGRDDOYNSSU-UHFFFAOYSA-N methyl 3-[4-[4-[4-[(e)-n'-methoxycarbonylcarbamimidoyl]phenyl]-1-methylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(=N)NC(=O)OC)=CN1C HAOIGRDDOYNSSU-UHFFFAOYSA-N 0.000 claims 1
- TWDWYEGKNMAKIZ-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1,3,4-thiadiazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C(N)=N)S1 TWDWYEGKNMAKIZ-UHFFFAOYSA-N 0.000 claims 1
- YXHRKKMNZDFQSK-UHFFFAOYSA-N methyl 3-[5-[4-(4-carbamimidoylphenyl)phenyl]-1,3,4-thiadiazol-2-yl]propanoate Chemical compound S1C(CCC(=O)OC)=NN=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)C=C1 YXHRKKMNZDFQSK-UHFFFAOYSA-N 0.000 claims 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000000197 pyrolysis Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 125000004354 sulfur functional group Chemical group 0.000 claims 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4124942.9 | 1991-07-27 | ||
| DE4124942A DE4124942A1 (de) | 1991-07-27 | 1991-07-27 | 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR930002344A true KR930002344A (ko) | 1993-02-23 |
Family
ID=6437152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920013494A Withdrawn KR930002344A (ko) | 1991-07-27 | 1992-07-27 | 5-원 헤테로사이클릭 화합물, 이의 제조방법 및 이를 함유하는 약제학적 조성물 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5463071A (enExample) |
| EP (1) | EP0525629A3 (enExample) |
| JP (1) | JPH05221999A (enExample) |
| KR (1) | KR930002344A (enExample) |
| AU (1) | AU652064B2 (enExample) |
| CA (1) | CA2074685A1 (enExample) |
| DE (1) | DE4124942A1 (enExample) |
| FI (1) | FI923366L (enExample) |
| HU (1) | HUT61747A (enExample) |
| IE (1) | IE922420A1 (enExample) |
| IL (1) | IL102638A (enExample) |
| MX (1) | MX9204354A (enExample) |
| NO (1) | NO922940L (enExample) |
| NZ (1) | NZ243713A (enExample) |
| TW (1) | TW225537B (enExample) |
| ZA (1) | ZA925573B (enExample) |
Families Citing this family (97)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4213931A1 (de) * | 1992-04-28 | 1993-11-04 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4213919A1 (de) * | 1992-04-28 | 1993-11-04 | Thomae Gmbh Dr K | Cyclische iminoderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE59303178D1 (de) * | 1992-04-28 | 1996-08-14 | Thomae Gmbh Dr K | Tritiumarkierte Fibrinogen-Rezeptor-Antagonisten, deren Verwendung und Verfahren zur ihrer Herstellung |
| DE4302051A1 (de) * | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE4304650A1 (de) * | 1993-02-16 | 1994-08-18 | Thomae Gmbh Dr K | Kondensierte 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US5652242A (en) * | 1993-03-29 | 1997-07-29 | Zeneca Limited | Heterocyclic derivatives |
| US5753659A (en) * | 1993-03-29 | 1998-05-19 | Zeneca Limited | Heterocyclic compouds |
| GB9406144D0 (en) * | 1993-03-29 | 1994-05-18 | Zeneca Ltd | Heterocyclic compounds |
| PL310889A1 (en) * | 1993-03-29 | 1996-01-08 | Zeneca Ltd | Heterocyclic derivatives as inhibitors of thrombocytes aggregation |
| US5463011A (en) * | 1993-06-28 | 1995-10-31 | Zeneca Limited | Acid derivatives |
| GB9313285D0 (en) * | 1993-06-28 | 1993-08-11 | Zeneca Ltd | Acid derivatives |
| GB9313268D0 (en) * | 1993-06-28 | 1993-08-11 | Zeneca Ltd | Chemical compounds |
| EP0730590B1 (en) * | 1993-11-24 | 2001-01-17 | Dupont Pharmaceuticals Company | isoxazoline and isoxazole fibrinogen receptor antagonists |
| US5523302A (en) * | 1993-11-24 | 1996-06-04 | The Du Pont Merck Pharmaceutical Company | Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists |
| JPH09505589A (ja) * | 1993-11-24 | 1997-06-03 | ザ・デュポン・メルク・ファーマシュウティカル・カンパニー | フィブリノーゲン受容体アンタゴニストとして有用なイソオキサゾリン化合物 |
| US5446056A (en) * | 1993-11-24 | 1995-08-29 | The Du Pont Merck Pharmaceutical Company | Isoxazoline compounds useful as fibrinogen receptor antagonists |
| US5849736A (en) * | 1993-11-24 | 1998-12-15 | The Dupont Merck Pharmaceutical Company | Isoxazoline and isoxazole fibrinogen receptor antagonists |
| US5563158A (en) * | 1993-12-28 | 1996-10-08 | The Dupont Merck Pharmaceutical Company | Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists |
| ZA963391B (en) * | 1995-05-24 | 1997-10-29 | Du Pont Merck Pharma | Isoxazoline fibrinogen receptor antagonists. |
| US5710159A (en) * | 1996-05-09 | 1998-01-20 | The Dupont Merck Pharmaceutical Company | Integrin receptor antagonists |
| IL118325A0 (en) * | 1995-05-25 | 1996-10-31 | Pont Merck And Pharmaceutical | Integrin receptor antagonists and pharmaceutical compositions containing them |
| US5668165A (en) * | 1995-06-07 | 1997-09-16 | Scriptgen Pharmaceuticals, Inc. | Small molecule inhibition of RNA/ligand binding |
| ZA966885B (en) * | 1995-08-22 | 1998-02-16 | Du Pont Merck Pharma | Substituted cyclic ureas and derivatives thereof useful as retroviral protease inhibitors. |
| CA2229617A1 (en) * | 1995-10-20 | 1997-05-01 | Dr. Karl Thomae Gmbh | 5-membered heterocycles, medicaments containing these compounds, their use and processes for their preparation |
| DE19605766A1 (de) * | 1996-02-16 | 1997-08-21 | Basf Ag | Substituierte 2-Phenylpyridine |
| US6011052A (en) * | 1996-04-30 | 2000-01-04 | Warner-Lambert Company | Pyrazolone derivatives as MCP-1 antagonists |
| WO1997049698A1 (en) * | 1996-06-21 | 1997-12-31 | Glaxo Group Limited | Piperidine acetic acid derivatives and their use in the treatment of thrombotic disorders |
| AR008245A1 (es) * | 1996-06-21 | 1999-12-29 | Glaxo Group Ltd | Derivados de acido acetico, uso de los mismos en la fabricacion de un agente terapeutico y proceso para preparar dichos derivados |
| US6124289A (en) * | 1996-07-24 | 2000-09-26 | Dupont Pharmaceuticals Co. | Azolo triazines and pyrimidines |
| US6191131B1 (en) | 1997-07-23 | 2001-02-20 | Dupont Pharmaceuticals Company | Azolo triazines and pyrimidines |
| US7094782B1 (en) | 1996-07-24 | 2006-08-22 | Bristol-Myers Squibb Company | Azolo triazines and pyrimidines |
| US6060478A (en) * | 1996-07-24 | 2000-05-09 | Dupont Pharmaceuticals | Azolo triazines and pyrimidines |
| US6313124B1 (en) | 1997-07-23 | 2001-11-06 | Dupont Pharmaceuticals Company | Tetrazine bicyclic compounds |
| US6004955A (en) * | 1996-08-15 | 1999-12-21 | Dupont Pharmaceuticals Company | Cyclic carbamates and isoxazolidines as IIb/IIIa antagonists |
| AU3970697A (en) * | 1996-08-15 | 1998-03-06 | Du Pont Pharmaceuticals Company | Cyclic carbamates and isoxazolidines as iib/iiia antagonists |
| AU4064597A (en) * | 1996-08-16 | 1998-03-06 | Du Pont Pharmaceuticals Company | Amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof |
| US6057342A (en) * | 1996-08-16 | 2000-05-02 | Dupont Pharmaceutical Co. | Amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof |
| DE19647381A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Ag | Neue Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten |
| US6548512B1 (en) | 1996-12-23 | 2003-04-15 | Bristol-Myers Squibb Pharma Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| US6020357A (en) * | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| US6187797B1 (en) | 1996-12-23 | 2001-02-13 | Dupont Pharmaceuticals Company | Phenyl-isoxazoles as factor XA Inhibitors |
| ZA9711586B (en) | 1996-12-23 | 1999-07-01 | Du Pont Merck Pharma | Nitrogen containing heteroaromatics as factor Xa inhibitors. |
| AR012443A1 (es) * | 1997-04-16 | 2000-10-18 | Uriach & Cia Sa J | Nuevas carboxamidas como inhibidores de la agregacion plaquetaria, procedimiento para su preparacion, composiciones farmaceuticas que loscontienen y uso de los mismos en la manufactura de medicamentos |
| ZA985251B (en) | 1997-06-19 | 1999-12-17 | Du Pont Merck Pharma | Inhibitors of factor Xa with a neutral P1 specificity group. |
| US5998424A (en) | 1997-06-19 | 1999-12-07 | Dupont Pharmaceuticals Company | Inhibitors of factor Xa with a neutral P1 specificity group |
| JP2002507968A (ja) * | 1997-06-19 | 2002-03-12 | デュポン ファーマシューティカルズ カンパニー | 中性のＰ１特異性基を有するＸａ因子阻害剤 |
| US6339099B1 (en) * | 1997-06-20 | 2002-01-15 | Dupont Pharmaceuticals Company | Guanidine mimics as factor Xa inhibitors |
| US5886191A (en) * | 1997-08-18 | 1999-03-23 | Dupont Pharmaceuticals Company | Amidinoindoles, amidinoazoles, and analogs thereof |
| IL136267A0 (en) * | 1997-11-26 | 2001-05-20 | Du Pont Pharm Co | 1,3,4-THIADIZOLES AND 1,3,4-OXADIAZOLES AS αVβ3 ANTAGONISTS |
| US6271237B1 (en) | 1997-12-22 | 2001-08-07 | Dupont Pharmaceuticals Company | Nitrogen containing heteromatics with ortho-substituted P1s as factor Xa inhabitors |
| JP2002509924A (ja) | 1998-03-27 | 2002-04-02 | デュポン ファーマシューティカルズ カンパニー | 第Ｘａ因子阻害剤としてのジ置換ピラゾリン類およびトリアゾリン類 |
| US6348504B1 (en) | 1999-03-30 | 2002-02-19 | Richard E. Olson | Oxime ethers as IIb/IIa antagonists |
| DE60003025T2 (de) | 1999-04-02 | 2004-03-18 | Bristol-Myers Squibb Pharma Co. | Arylsulfonyle als faktor xa inhibitoren |
| EE200200123A (et) | 1999-09-10 | 2003-08-15 | Merck & Co., Inc. | Türosiinkinaasi pärssiv ühend, seda sisaldav farmatseutiline kompositsioon ning raviotstarbeline kasutamine |
| CA2450562A1 (en) | 2001-06-22 | 2003-01-03 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| MXPA04003451A (es) * | 2001-10-09 | 2005-02-17 | Dimensional Pharm Inc | Difeniloxazoles substituidos, la sintesis de los mismos y el uso de los mismo como detectores fluorescencia. |
| MY151199A (en) | 2001-11-02 | 2014-04-30 | Rigel Pharmaceuticals Inc | Substituted diphenyl heterocycles useful for treating hcv infection |
| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| ATE434610T1 (de) * | 2002-03-13 | 2009-07-15 | Euro Celtique Sa | Aryl substituierte pyrimidine und deren verwendung |
| US20040023981A1 (en) * | 2002-07-24 | 2004-02-05 | Yu Ren | Salt forms with tyrosine kinase activity |
| US20040023978A1 (en) * | 2002-07-24 | 2004-02-05 | Yu Ren | Active salt forms with tyrosine kinase activity |
| US6872724B2 (en) * | 2002-07-24 | 2005-03-29 | Merck & Co., Inc. | Polymorphs with tyrosine kinase activity |
| WO2004018463A2 (en) * | 2002-08-23 | 2004-03-04 | Rigel Pharmaceuticals, Inc. | Pyridyl substituted heterocycles useful for treating or preventing hcv infection |
| US7326790B2 (en) * | 2003-05-02 | 2008-02-05 | Rigel Pharmaceuticals, Inc. | Diphenylisoxazole compounds and hydro isomers thereof |
| US7115642B2 (en) | 2003-05-02 | 2006-10-03 | Rigel Pharmaceuticals, Inc. | Substituted diphenyl isoxazoles, pyrazoles and oxadiazoles useful for treating HCV infection |
| US7220745B2 (en) * | 2003-05-15 | 2007-05-22 | Rigel Pharmaceuticals | Heterocyclic compounds useful to treat HCV |
| WO2005049065A2 (en) * | 2003-11-19 | 2005-06-02 | Rigel Pharmaceuticals, Inc. | Synergistic combinations of dihaloacetamide with interferon or ribavirin for treatment hcv infections |
| WO2005058848A1 (en) * | 2003-12-17 | 2005-06-30 | Merck & Co., Inc. | (3,4-disubstituted)propanoic carboxylates as s1p (edg) receptor agonists |
| US7514434B2 (en) | 2004-02-23 | 2009-04-07 | Rigel Pharmaceuticals, Inc. | Heterocyclic compounds having an oxadiazole moiety and hydro isomers thereof |
| US20050239751A1 (en) * | 2004-03-26 | 2005-10-27 | Rigel Pharmaceuticals, Inc. | Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses |
| NZ550114A (en) * | 2004-04-20 | 2011-02-25 | Transtech Pharma Inc | Substituted thiazole and pyrimidine derivatives as melanocortin receptor modulators |
| US7829712B2 (en) * | 2004-09-20 | 2010-11-09 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-CoA-desaturase |
| CN101083982A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 用于治疗硬脂酰CoA去饱和酶介导的疾病的杂环衍生物 |
| AU2005286846A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| CA2580857A1 (en) * | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| CA2580844A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-coa desaturase |
| TW200624427A (en) * | 2004-09-20 | 2006-07-16 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| JP5080256B2 (ja) * | 2004-09-20 | 2012-11-21 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 二環式複素環誘導体およびステアロイル−ＣｏＡデサチュラーゼ（ＳＣＤ）のインヒビターとしてのそれらの使用 |
| BRPI0515499A (pt) * | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados de piridina para a inibição de estearoil-coa-desaturase humana |
| WO2006034440A2 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| AP2007004047A0 (en) * | 2005-01-20 | 2007-06-30 | Pfizer Ltd | Substituted triazole derivatives as oxtocin antagonists |
| CN101203498A (zh) * | 2005-05-02 | 2008-06-18 | 里格尔药品股份有限公司 | 包括可代谢部分的杂环抗病毒化合物及其用途 |
| US8541457B2 (en) * | 2005-06-03 | 2013-09-24 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-CoA desaturase inhibitors |
| CA2731442A1 (en) * | 2008-08-29 | 2010-03-04 | Transtech Pharma, Inc. | Substituted aminothiazole derivatives, pharmaceutical compositions, and methods of use |
| WO2013063458A2 (en) * | 2011-10-27 | 2013-05-02 | Mayo Foundation For Medical Education And Research | Inhibiting g protein coupled receptor 6 kinase polypeptides |
| US9546155B2 (en) | 2012-06-15 | 2017-01-17 | Mitsubishi Tanabe Pharma Corporation | Aromatic heterocyclic compound |
| SG10202006053UA (en) | 2014-08-04 | 2020-07-29 | Nuevolution As | Optionally fused heterocyclyl-substituted derivatives of pyrimidine useful for the treatment of inflammatory, metabolic, oncologic and autoimmune diseases |
| SG11201809751XA (en) | 2016-05-26 | 2018-12-28 | Zeno Royalties & Milestones Llc | Egfr inhibitor compounds |
| JP2022500499A (ja) * | 2018-09-07 | 2022-01-04 | ピク セラピューティクス， インコーポレイテッド | Ｅｉｆ４ｅ阻害剤およびその使用 |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN114728170B (zh) | 2019-12-20 | 2024-03-01 | 纽韦卢森公司 | 对核受体具有活性的化合物 |
| WO2021124277A1 (en) | 2019-12-20 | 2021-06-24 | Nuevolution A/S | Compounds active towards nuclear receptors |
| CN115515685B (zh) | 2020-03-03 | 2025-04-08 | 皮克医疗公司 | Eif4e抑制剂及其用途 |
| CA3174252A1 (en) | 2020-03-31 | 2021-10-07 | Nuevolution A/S | Compounds active towards nuclear receptors |
| JP7713954B2 (ja) | 2020-03-31 | 2025-07-28 | ヌエヴォリューション・アクティーゼルスカブ | 核内受容体に対して活性な化合物 |
| WO2023028238A1 (en) | 2021-08-25 | 2023-03-02 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| JP2024534127A (ja) | 2021-08-25 | 2024-09-18 | ピク セラピューティクス， インコーポレイテッド | ｅＩＦ４Ｅ阻害剤及びその使用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3792170A (en) * | 1972-03-14 | 1974-02-12 | Merck & Co Inc | Novel alkylsulfinyl derivatives for pain,fever and inflammation |
| DE3486009T2 (de) * | 1983-09-09 | 1993-04-15 | Takeda Chemical Industries Ltd | 5-pyridyl-1,3-thiazol-derivate, ihre herstellung und anwendung. |
| US4820723A (en) * | 1987-08-14 | 1989-04-11 | Eli Lilly And Company | Disubstituted tetrazole leukotriene antagonists and methods for their use thereas |
| US4820722A (en) * | 1987-08-14 | 1989-04-11 | Eli Lilly And Company | Disubstituted tetrazoles and their use as leukotriene antagonists |
| GB8725260D0 (en) * | 1987-10-28 | 1987-12-02 | Lilly Industries Ltd | Organic compounds |
| US5081127A (en) * | 1988-01-07 | 1992-01-14 | E. I. Du Pont De Nemours And Company | Substituted 1,2,3-triazole angiotensin II antagonists |
| EP0440183A1 (en) * | 1990-02-01 | 1991-08-07 | Takeda Chemical Industries, Ltd. | Oxazole compounds, their production and use |
| DE4102024A1 (de) * | 1991-01-24 | 1992-07-30 | Thomae Gmbh Dr K | Biphenylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4107857A1 (de) * | 1991-03-12 | 1992-09-17 | Thomae Gmbh Dr K | Cyclische harnstoffderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
-
1991
- 1991-07-27 DE DE4124942A patent/DE4124942A1/de not_active Withdrawn
-
1992
- 1992-06-16 TW TW081104702A patent/TW225537B/zh active
- 1992-07-22 EP EP92112568A patent/EP0525629A3/de not_active Withdrawn
- 1992-07-24 IE IE242092A patent/IE922420A1/en not_active Application Discontinuation
- 1992-07-24 JP JP4198359A patent/JPH05221999A/ja active Pending
- 1992-07-24 NZ NZ243713A patent/NZ243713A/en unknown
- 1992-07-24 CA CA002074685A patent/CA2074685A1/en not_active Abandoned
- 1992-07-24 HU HU9202450A patent/HUT61747A/hu unknown
- 1992-07-24 ZA ZA925573A patent/ZA925573B/xx unknown
- 1992-07-24 MX MX9204354A patent/MX9204354A/es not_active IP Right Cessation
- 1992-07-24 NO NO92922940A patent/NO922940L/no unknown
- 1992-07-24 IL IL10263892A patent/IL102638A/en not_active IP Right Cessation
- 1992-07-24 FI FI923366A patent/FI923366L/fi not_active Application Discontinuation
- 1992-07-27 AU AU20569/92A patent/AU652064B2/en not_active Ceased
- 1992-07-27 KR KR1019920013494A patent/KR930002344A/ko not_active Withdrawn
-
1993
- 1993-11-08 US US08/148,724 patent/US5463071A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HUT61747A (en) | 1993-03-01 |
| IL102638A (en) | 1996-10-16 |
| JPH05221999A (ja) | 1993-08-31 |
| EP0525629A3 (en) | 1997-03-19 |
| NO922940D0 (no) | 1992-07-24 |
| IL102638A0 (en) | 1993-01-14 |
| NZ243713A (en) | 1995-06-27 |
| FI923366A7 (fi) | 1993-01-28 |
| HU9202450D0 (en) | 1992-10-28 |
| FI923366A0 (fi) | 1992-07-24 |
| IE922420A1 (en) | 1993-01-27 |
| FI923366L (fi) | 1993-01-28 |
| CA2074685A1 (en) | 1993-01-28 |
| US5463071A (en) | 1995-10-31 |
| AU2056992A (en) | 1993-01-28 |
| EP0525629A2 (de) | 1993-02-03 |
| ZA925573B (en) | 1994-01-24 |
| TW225537B (enExample) | 1994-06-21 |
| AU652064B2 (en) | 1994-08-11 |
| DE4124942A1 (de) | 1993-01-28 |
| MX9204354A (es) | 1993-01-01 |
| NO922940L (no) | 1993-01-28 |
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