HRP20120230T1 - Triazolopiridini kao inhibitori par1, njihovo dobivanje i upotreba kao medikamenata - Google Patents
Triazolopiridini kao inhibitori par1, njihovo dobivanje i upotreba kao medikamenata Download PDFInfo
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- HRP20120230T1 HRP20120230T1 HR20120230T HRP20120230T HRP20120230T1 HR P20120230 T1 HRP20120230 T1 HR P20120230T1 HR 20120230 T HR20120230 T HR 20120230T HR P20120230 T HRP20120230 T HR P20120230T HR P20120230 T1 HRP20120230 T1 HR P20120230T1
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- alkyl
- cycloalkyl
- alkylene
- triazolo
- imino
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- 101100361282 Schizosaccharomyces pombe (strain 972 / ATCC 24843) rpm1 gene Proteins 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 100
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 62
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 60
- 125000000217 alkyl group Chemical group 0.000 claims abstract 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 41
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 33
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 33
- 239000011737 fluorine Substances 0.000 claims abstract 33
- 229910052736 halogen Inorganic materials 0.000 claims abstract 25
- 150000002367 halogens Chemical class 0.000 claims abstract 25
- 125000002947 alkylene group Chemical group 0.000 claims abstract 23
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 125000003118 aryl group Chemical group 0.000 claims abstract 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004429 atom Chemical group 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- 239000001301 oxygen Substances 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims abstract 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract 2
- -1 pyrrolidin-2,5-dionyl Chemical group 0.000 claims 33
- 239000012634 fragment Substances 0.000 claims 8
- 125000006413 ring segment Chemical group 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 238000000034 method Methods 0.000 claims 5
- 125000002785 azepinyl group Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 150000003949 imides Chemical class 0.000 claims 4
- 150000003951 lactams Chemical class 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 3
- 208000007536 Thrombosis Diseases 0.000 claims 3
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims 3
- HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical group C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 claims 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 2
- WFDUOXJKEHADRT-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1,5-benzodiazepine Chemical group N1CCCNC2=CC=CC=C21 WFDUOXJKEHADRT-UHFFFAOYSA-N 0.000 claims 2
- YBBLSBDJIKMXNQ-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzothiazine Chemical group C1=CC=C2NCCSC2=C1 YBBLSBDJIKMXNQ-UHFFFAOYSA-N 0.000 claims 2
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical group C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- 208000005189 Embolism Diseases 0.000 claims 2
- 102000009123 Fibrin Human genes 0.000 claims 2
- 108010073385 Fibrin Proteins 0.000 claims 2
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 2
- 150000001805 chlorine compounds Chemical group 0.000 claims 2
- 229950003499 fibrin Drugs 0.000 claims 2
- 230000003176 fibrotic effect Effects 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- QDQAJASRDVTTEV-UHFFFAOYSA-N 1-(3-bromo-4,5-dimethoxyphenyl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC(CC)CC)C=CC2=NN1CC(=O)C1=CC(Br)=C(OC)C(OC)=C1 QDQAJASRDVTTEV-UHFFFAOYSA-N 0.000 claims 1
- XOHLPPGEBQGGQW-UHFFFAOYSA-N 1-(3-bromo-5-methoxyphenyl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC(CC)CC)C=CC2=NN1CC(=O)C1=CC(Br)=CC(OC)=C1 XOHLPPGEBQGGQW-UHFFFAOYSA-N 0.000 claims 1
- OELPWMKOHNNTJI-UHFFFAOYSA-N 1-(3-chloro-4,5-dimethoxyphenyl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC(CC)CC)C=CC2=NN1CC(=O)C1=CC(Cl)=C(OC)C(OC)=C1 OELPWMKOHNNTJI-UHFFFAOYSA-N 0.000 claims 1
- NLSXKVKJTJRTEO-UHFFFAOYSA-N 1-(3-chloro-5-methoxyphenyl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC(CC)CC)C=CC2=NN1CC(=O)C1=CC(Cl)=CC(OC)=C1 NLSXKVKJTJRTEO-UHFFFAOYSA-N 0.000 claims 1
- BNZMJGXRNHWJFU-UHFFFAOYSA-N 1-(3-tert-butyl-4,5-diethoxyphenyl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound CC(C)(C)C1=C(OCC)C(OCC)=CC(C(=O)CN2C(N3N=C(OC(CC)CC)C=CC3=N2)=N)=C1 BNZMJGXRNHWJFU-UHFFFAOYSA-N 0.000 claims 1
- LBEFGXUZJKXPAB-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC)C=CC2=NN1CC(=O)C(C=C(C=1OC)C(C)(C)C)=CC=1N1CCOCC1 LBEFGXUZJKXPAB-UHFFFAOYSA-N 0.000 claims 1
- YTQPMMAEPAHRSY-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-morpholin-4-yl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CCOCC2)C=C1C(=O)CN(C(N1N=2)=N)N=C1C=CC=2N1CCOCC1 YTQPMMAEPAHRSY-UHFFFAOYSA-N 0.000 claims 1
- HPSWHJDEAYKFLZ-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC(CC)CC)C=CC2=NN1CC(=O)C(C=C(C=1OC)C(C)(C)C)=CC=1N1CCOCC1 HPSWHJDEAYKFLZ-UHFFFAOYSA-N 0.000 claims 1
- CLRDZSGRAVMURO-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-phenoxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CCOCC2)C=C1C(=O)CN(C(N1N=2)=N)N=C1C=CC=2OC1=CC=CC=C1 CLRDZSGRAVMURO-UHFFFAOYSA-N 0.000 claims 1
- SGIYPFDRRTURTJ-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-phenylmethoxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CCOCC2)C=C1C(=O)CN(C(N1N=2)=N)N=C1C=CC=2OCC1=CC=CC=C1 SGIYPFDRRTURTJ-UHFFFAOYSA-N 0.000 claims 1
- SGLSFEAACRMAEV-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-piperidin-1-yl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CCOCC2)C=C1C(=O)CN(C(N1N=2)=N)N=C1C=CC=2N1CCCCC1 SGLSFEAACRMAEV-UHFFFAOYSA-N 0.000 claims 1
- LBAYIZITCQYKCL-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-propan-2-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(=O)CN2C(N3N=C(OC(C)C)C=CC3=N2)=N)C=C(C(C)(C)C)C(OC)=C1N1CCOCC1 LBAYIZITCQYKCL-UHFFFAOYSA-N 0.000 claims 1
- BOHIDUGQJRJJJK-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-chloro-3-imino-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(=O)CN2C(N3N=C(Cl)C(C)=C(C)C3=N2)=N)C=C(C(C)(C)C)C(OC)=C1N1CCOCC1 BOHIDUGQJRJJJK-UHFFFAOYSA-N 0.000 claims 1
- CRRXUPLAOQVFFA-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-chloro-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(=O)CN2C(N3N=C(Cl)C=C(C)C3=N2)=N)C=C(C(C)(C)C)C(OC)=C1N1CCOCC1 CRRXUPLAOQVFFA-UHFFFAOYSA-N 0.000 claims 1
- ANHBRMBHKAZADD-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-chloro-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(=O)CN2C(N3N=C(Cl)C=CC3=N2)=N)C=C(C(C)(C)C)C(OC)=C1N1CCOCC1 ANHBRMBHKAZADD-UHFFFAOYSA-N 0.000 claims 1
- PSZPXUCGYWGNTI-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclobutyloxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CCOCC2)C=C1C(=O)CN(C(N1N=2)=N)N=C1C=CC=2OC1CCC1 PSZPXUCGYWGNTI-UHFFFAOYSA-N 0.000 claims 1
- AFKWPSRRQYJQJZ-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclohexyloxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CCOCC2)C=C1C(=O)CN(C(N1N=2)=N)N=C1C=CC=2OC1CCCCC1 AFKWPSRRQYJQJZ-UHFFFAOYSA-N 0.000 claims 1
- FLODBFXRKYEZEJ-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-ethoxy-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OCC)C=C(C)C2=NN1CC(=O)C(C=C(C=1OC)C(C)(C)C)=CC=1N1CCOCC1 FLODBFXRKYEZEJ-UHFFFAOYSA-N 0.000 claims 1
- VXKNDAUXQFFXOR-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-ethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OCC)C=CC2=NN1CC(=O)C(C=C(C=1OC)C(C)(C)C)=CC=1N1CCOCC1 VXKNDAUXQFFXOR-UHFFFAOYSA-N 0.000 claims 1
- RWCXXPRJYVYPKP-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-ethyl-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(CC)C=CC2=NN1CC(=O)C(C=C(C=1OC)C(C)(C)C)=CC=1N1CCOCC1 RWCXXPRJYVYPKP-UHFFFAOYSA-N 0.000 claims 1
- BCJHREWTUUAUBE-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-imidazol-1-yl-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CCOCC2)C=C1C(=O)CN(C(N1N=2)=N)N=C1C=CC=2N1C=CN=C1 BCJHREWTUUAUBE-UHFFFAOYSA-N 0.000 claims 1
- CEQLVCAHJLJXGO-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-[3-imino-6-(2,2,2-trifluoroethoxy)-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone Chemical compound C1=C(C(=O)CN2C(N3N=C(OCC(F)(F)F)C=CC3=N2)=N)C=C(C(C)(C)C)C(OC)=C1N1CCOCC1 CEQLVCAHJLJXGO-UHFFFAOYSA-N 0.000 claims 1
- BSBZSUWJSUEGHZ-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-[6-(cyclopropylmethoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CCOCC2)C=C1C(=O)CN(C(N1N=2)=N)N=C1C=CC=2OCC1CC1 BSBZSUWJSUEGHZ-UHFFFAOYSA-N 0.000 claims 1
- ZZUMRUWDOKYKHH-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-[6-(diethylamino)-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone Chemical compound N=C1N2N=C(N(CC)CC)C=C(C)C2=NN1CC(=O)C(C=C(C=1OC)C(C)(C)C)=CC=1N1CCOCC1 ZZUMRUWDOKYKHH-UHFFFAOYSA-N 0.000 claims 1
- LPSHVBSWEQHABN-UHFFFAOYSA-N 1-(3-tert-butyl-5-ethoxyphenyl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound CC(C)(C)C1=CC(OCC)=CC(C(=O)CN2C(N3N=C(OC(CC)CC)C=CC3=N2)=N)=C1 LPSHVBSWEQHABN-UHFFFAOYSA-N 0.000 claims 1
- HSUKYIKYRIKIPS-UHFFFAOYSA-N 1-(3-tert-butyl-5-methoxyphenyl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC(CC)CC)C=CC2=NN1CC(=O)C1=CC(OC)=CC(C(C)(C)C)=C1 HSUKYIKYRIKIPS-UHFFFAOYSA-N 0.000 claims 1
- HYKXXHCUVYRDOM-UHFFFAOYSA-N 1-(3-tert-butyl-5-methoxyphenyl)-2-(3-imino-8-methyl-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC(CC)CC)C=C(C)C2=NN1CC(=O)C1=CC(OC)=CC(C(C)(C)C)=C1 HYKXXHCUVYRDOM-UHFFFAOYSA-N 0.000 claims 1
- MEPIERCKUJCDII-UHFFFAOYSA-N 1-(3-tert-butyl-5-methoxyphenyl)-2-[3-imino-6-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone Chemical compound N=C1N2N=C(OCCOC)C=CC2=NN1CC(=O)C1=CC(OC)=CC(C(C)(C)C)=C1 MEPIERCKUJCDII-UHFFFAOYSA-N 0.000 claims 1
- GHUSCDBWQKEYGQ-UHFFFAOYSA-N 1-(3-tert-butyl-5-methoxyphenyl)-2-[3-imino-6-[2-(2-methoxyethoxy)ethoxy]-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone Chemical compound N=C1N2N=C(OCCOCCOC)C=CC2=NN1CC(=O)C1=CC(OC)=CC(C(C)(C)C)=C1 GHUSCDBWQKEYGQ-UHFFFAOYSA-N 0.000 claims 1
- ZHNXKLIFVWRFAI-UHFFFAOYSA-N 1-(5-bromo-2,3-dimethoxyphenyl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC(CC)CC)C=CC2=NN1CC(=O)C1=CC(Br)=CC(OC)=C1OC ZHNXKLIFVWRFAI-UHFFFAOYSA-N 0.000 claims 1
- NHFNHJQXYYFRHL-UHFFFAOYSA-N 1-(8-tert-butyl-4-methyl-2,3-dihydro-1,4-benzoxazin-6-yl)-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound CN1CCOC(C(=C2)C(C)(C)C)=C1C=C2C(=O)CN1N=C2C=CC(OC(CC)CC)=NN2C1=N NHFNHJQXYYFRHL-UHFFFAOYSA-N 0.000 claims 1
- SKMYZTMEXSZRHK-UHFFFAOYSA-N 1-[3-(3,3-dimethylbutoxy)-5-ethoxyphenyl]-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound CCOC1=CC(OCCC(C)(C)C)=CC(C(=O)CN2C(N3N=C(OC(CC)CC)C=CC3=N2)=N)=C1 SKMYZTMEXSZRHK-UHFFFAOYSA-N 0.000 claims 1
- ZKDHCMCKBDATPX-UHFFFAOYSA-N 1-[3-(3,3-dimethylbutoxy)-5-methoxyphenyl]-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound N=C1N2N=C(OC(CC)CC)C=CC2=NN1CC(=O)C1=CC(OC)=CC(OCCC(C)(C)C)=C1 ZKDHCMCKBDATPX-UHFFFAOYSA-N 0.000 claims 1
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- ATQMIVLOGUYNKI-UHFFFAOYSA-N 1-[3-(cyclohexylmethoxy)-5-ethoxyphenyl]-2-(3-imino-6-pentan-3-yloxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone Chemical compound C=1C(C(=O)CN2C(N3N=C(OC(CC)CC)C=CC3=N2)=N)=CC(OCC)=CC=1OCC1CCCCC1 ATQMIVLOGUYNKI-UHFFFAOYSA-N 0.000 claims 1
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- 230000000250 revascularization Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000037390 scarring Effects 0.000 claims 1
- 230000009863 secondary prevention Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 201000005665 thrombophilia Diseases 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08290112 | 2008-02-05 | ||
PCT/EP2009/000406 WO2009097970A1 (de) | 2008-02-05 | 2009-01-23 | Triazolopyridazine als par1-inhibitoren, ihre herstellung und verwendung als arzneimittel |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20120230T1 true HRP20120230T1 (hr) | 2012-04-30 |
Family
ID=39539711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20120230T HRP20120230T1 (hr) | 2008-02-05 | 2012-03-13 | Triazolopiridini kao inhibitori par1, njihovo dobivanje i upotreba kao medikamenata |
Country Status (32)
Country | Link |
---|---|
US (2) | US8076336B2 (pl) |
EP (1) | EP2240487B1 (pl) |
JP (1) | JP5526040B2 (pl) |
KR (1) | KR20100114514A (pl) |
CN (1) | CN101981034B (pl) |
AR (1) | AR070410A1 (pl) |
AT (1) | ATE537172T1 (pl) |
AU (1) | AU2009211887B2 (pl) |
BR (1) | BRPI0907486A2 (pl) |
CA (1) | CA2713550C (pl) |
CL (1) | CL2009000236A1 (pl) |
CO (1) | CO6260083A2 (pl) |
CY (1) | CY1113228T1 (pl) |
DK (1) | DK2240487T3 (pl) |
ES (1) | ES2379447T3 (pl) |
HK (1) | HK1149011A1 (pl) |
HR (1) | HRP20120230T1 (pl) |
IL (1) | IL207205A0 (pl) |
MA (1) | MA32061B1 (pl) |
MX (1) | MX2010008490A (pl) |
MY (1) | MY152040A (pl) |
NZ (1) | NZ587141A (pl) |
PA (1) | PA8814801A1 (pl) |
PE (1) | PE20091455A1 (pl) |
PL (1) | PL2240487T3 (pl) |
PT (1) | PT2240487E (pl) |
RS (1) | RS52264B (pl) |
RU (1) | RU2499797C2 (pl) |
SI (1) | SI2240487T1 (pl) |
TW (1) | TW200946532A (pl) |
WO (1) | WO2009097970A1 (pl) |
ZA (1) | ZA201004467B (pl) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2663528A1 (en) * | 2006-09-18 | 2008-03-27 | Vertex Pharmaceuticals Incorporated | Heterocyclic inhibitors of c-met and uses thereof |
CA2713551C (en) | 2008-02-05 | 2016-06-14 | Sanofi-Aventis | Triazolium salts as par1 inhibitors, production thereof, and use as medicaments |
US8673890B2 (en) | 2009-10-29 | 2014-03-18 | Janssen Pharmaceutica Nv | 2,3-dihydro-1H-isoindol-1-imine derivatives useful as thrombin PAR-1 receptor antagonist |
BR112021025588A2 (pt) * | 2019-06-19 | 2022-02-01 | Nmd Pharma As | Processo para a preparação dos inibidores de canal de cloreto clc-1 |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4578464A (en) | 1983-11-22 | 1986-03-25 | Merrell Dow Pharmaceuticals Inc. | 6-Hydroxyalkylamino-8-methyl-1,2,4-triazolo-[4,3-b]pyridazine and related compounds |
HUT77130A (hu) * | 1994-09-16 | 1998-03-02 | Takeda Chemical Industries Ltd. | [1,2,4] Triazolo[1,5-b]piridazin-származékok, eljárás előállításukra, és a vegyületeket tartalmazó gyógyszerkészítmények |
US6063847A (en) | 1997-11-25 | 2000-05-16 | Schering Corporation | Thrombin receptor antagonists |
US7488742B2 (en) | 2000-06-15 | 2009-02-10 | Schering Corporation | Thrombin receptor antagonists |
IL158491A0 (en) * | 2001-04-19 | 2004-05-12 | Eisai Co Ltd | 2-iminopyrrolidine derivatives |
CA2448509A1 (en) | 2001-05-25 | 2002-12-05 | Mochida Pharmaceutical Co., Ltd. | 4-hydroxypiperidine derivatives having analgesic activity |
WO2003031442A1 (fr) | 2001-10-05 | 2003-04-17 | Takeda Chemical Industries, Ltd. | Composes heterocycliques, derives oxazole, procede permettant de les presenter et leur utilisation |
HUP0500443A3 (en) | 2001-10-18 | 2009-12-28 | Schering Corp | Himbacine analogues as thrombin receptor antagonists and pharmaceutical compositions containing them |
SI2065384T1 (sl) | 2002-04-16 | 2011-05-31 | Schering Corp | Tricikliäśni trombin receptor antagonist |
KR20050104376A (ko) | 2003-02-19 | 2005-11-02 | 에자이 가부시키가이샤 | 고리형상 벤즈아미딘 유도체의 제조방법 |
TW200531688A (en) | 2004-03-05 | 2005-10-01 | Hoffmann La Roche | Novel pentafluorosulfanyl compounds, their manufacture and use as pharmaceutical agents |
WO2006051648A1 (ja) | 2004-11-09 | 2006-05-18 | Eisai R & D Management Co., Ltd. | トロンビン受容体アンタゴニストを有効成分とするくも膜下出血に伴う血管攣縮の治療剤 |
BRPI0620292B1 (pt) * | 2005-12-21 | 2021-08-24 | Janssen Pharmaceutica N. V. | Compostos de triazolopiridazinas como moduladores da cinase, composição, uso, combinação e processo de preparo do referido composto |
DE102006025318A1 (de) * | 2006-05-31 | 2007-12-06 | Bayer Healthcare Ag | Dihydro-pyrrolopyridin-, Dihydro-pyrrolopyridazin- und Dihydro-pyrrolopyrimidin-Derivate und ihre Verwendung |
DE102006036023A1 (de) * | 2006-08-02 | 2008-02-07 | Sanofi-Aventis | Imino-imidazo-pyridinderivate mit antithrombotischer Aktivität |
SI2242740T1 (sl) | 2008-02-05 | 2013-03-29 | Sanofi | SF5-derivati kot PAR1 inhibitorji, njihova priprava in uporaba kot zdravila |
WO2009097973A2 (de) | 2008-02-05 | 2009-08-13 | Sanofi-Aventis | Imidazopyridazine als parl-inhibitoren, ihre herstellung und verwendung als arzneimittel |
CA2713551C (en) | 2008-02-05 | 2016-06-14 | Sanofi-Aventis | Triazolium salts as par1 inhibitors, production thereof, and use as medicaments |
US8394823B2 (en) | 2008-04-11 | 2013-03-12 | Bristol-Myers Squibb Company | Triazolopyridine compounds useful as DGAT1 inhibitors |
WO2009126624A1 (en) | 2008-04-11 | 2009-10-15 | Bristol-Myers Squibb Company | Triazolo compounds useful as dgat1 inhibitors |
-
2009
- 2009-01-23 CN CN2009801115086A patent/CN101981034B/zh not_active Expired - Fee Related
- 2009-01-23 ES ES09708289T patent/ES2379447T3/es active Active
- 2009-01-23 PT PT09708289T patent/PT2240487E/pt unknown
- 2009-01-23 AT AT09708289T patent/ATE537172T1/de active
- 2009-01-23 RU RU2010136957/04A patent/RU2499797C2/ru not_active IP Right Cessation
- 2009-01-23 MY MYPI20103226 patent/MY152040A/en unknown
- 2009-01-23 WO PCT/EP2009/000406 patent/WO2009097970A1/de active Application Filing
- 2009-01-23 MX MX2010008490A patent/MX2010008490A/es active IP Right Grant
- 2009-01-23 AU AU2009211887A patent/AU2009211887B2/en not_active Ceased
- 2009-01-23 NZ NZ587141A patent/NZ587141A/en not_active IP Right Cessation
- 2009-01-23 EP EP09708289A patent/EP2240487B1/de active Active
- 2009-01-23 SI SI200930192T patent/SI2240487T1/sl unknown
- 2009-01-23 RS RS20120103A patent/RS52264B/en unknown
- 2009-01-23 DK DK09708289.5T patent/DK2240487T3/da active
- 2009-01-23 CA CA2713550A patent/CA2713550C/en not_active Expired - Fee Related
- 2009-01-23 PL PL09708289T patent/PL2240487T3/pl unknown
- 2009-01-23 JP JP2010545378A patent/JP5526040B2/ja not_active Expired - Fee Related
- 2009-01-23 BR BRPI0907486-4A patent/BRPI0907486A2/pt not_active IP Right Cessation
- 2009-01-23 KR KR1020107017452A patent/KR20100114514A/ko not_active Application Discontinuation
- 2009-02-03 TW TW098103334A patent/TW200946532A/zh unknown
- 2009-02-03 CL CL2009000236A patent/CL2009000236A1/es unknown
- 2009-02-03 AR ARP090100348A patent/AR070410A1/es not_active Application Discontinuation
- 2009-02-03 PE PE2009000154A patent/PE20091455A1/es not_active Application Discontinuation
- 2009-02-03 PA PA20098814801A patent/PA8814801A1/es unknown
-
2010
- 2010-06-24 ZA ZA2010/04467A patent/ZA201004467B/en unknown
- 2010-07-25 IL IL207205A patent/IL207205A0/en unknown
- 2010-08-04 CO CO10095026A patent/CO6260083A2/es active IP Right Grant
- 2010-08-04 MA MA33059A patent/MA32061B1/fr unknown
- 2010-08-05 US US12/851,189 patent/US8076336B2/en not_active Expired - Fee Related
-
2011
- 2011-03-30 HK HK11103239.2A patent/HK1149011A1/xx not_active IP Right Cessation
- 2011-09-23 US US13/243,118 patent/US9079906B2/en not_active Expired - Fee Related
-
2012
- 2012-03-13 HR HR20120230T patent/HRP20120230T1/hr unknown
- 2012-03-14 CY CY20121100256T patent/CY1113228T1/el unknown
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