HRP20100158T1 - Novi indolizinski derivati, postupak njihovog dobivanja i terapijski pripravci koji iz sadrže - Google Patents
Novi indolizinski derivati, postupak njihovog dobivanja i terapijski pripravci koji iz sadrže Download PDFInfo
- Publication number
- HRP20100158T1 HRP20100158T1 HR20100158T HRP20100158T HRP20100158T1 HR P20100158 T1 HRP20100158 T1 HR P20100158T1 HR 20100158 T HR20100158 T HR 20100158T HR P20100158 T HRP20100158 T HR P20100158T HR P20100158 T1 HRP20100158 T1 HR P20100158T1
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- propyl
- methanone
- butyl
- methanone hydrochloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 4
- 125000003406 indolizinyl group Chemical class C=1(C=CN2C=CC=CC12)* 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 150000002478 indolizines Chemical class 0.000 claims 6
- 206010019280 Heart failures Diseases 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- MUFUIGUYKDROCP-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-(dipropylamino)propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCN(CCC)CCC)C=C1 MUFUIGUYKDROCP-UHFFFAOYSA-N 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010061216 Infarction Diseases 0.000 claims 2
- 206010042600 Supraventricular arrhythmias Diseases 0.000 claims 2
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000002861 ventricular Effects 0.000 claims 2
- WXVZHOARMPPZNL-UHFFFAOYSA-N (2-butyl-6-ethylindolizin-3-yl)-[4-[3-(dipropylamino)propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC(CC)=CN2C=1C(=O)C1=CC=C(CCCN(CCC)CCC)C=C1 WXVZHOARMPPZNL-UHFFFAOYSA-N 0.000 claims 1
- NLMNTBNIFULSJM-UHFFFAOYSA-N (2-butyl-6-ethylindolizin-3-yl)-[4-[3-[ethyl(propyl)amino]propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC(CC)=CN2C=1C(=O)C1=CC=C(CCCN(CC)CCC)C=C1 NLMNTBNIFULSJM-UHFFFAOYSA-N 0.000 claims 1
- PNFBXLWONFKQCP-UHFFFAOYSA-N (2-butyl-6-methylindolizin-3-yl)-[4-[3-(dipropylamino)propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC(C)=CN2C=1C(=O)C1=CC=C(CCCN(CCC)CCC)C=C1 PNFBXLWONFKQCP-UHFFFAOYSA-N 0.000 claims 1
- XZRYOPDUCAKOSC-UHFFFAOYSA-N (2-butyl-6-methylindolizin-3-yl)-[4-[3-[ethyl(propyl)amino]propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC(C)=CN2C=1C(=O)C1=CC=C(CCCN(CC)CCC)C=C1 XZRYOPDUCAKOSC-UHFFFAOYSA-N 0.000 claims 1
- IPXRKSXQJXESAH-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-(3-piperidin-1-ylpropyl)phenyl]methanone;oxalic acid Chemical compound OC(=O)C(O)=O.CCCCC=1C=C2C=CC=CN2C=1C(=O)C(C=C1)=CC=C1CCCN1CCCCC1 IPXRKSXQJXESAH-UHFFFAOYSA-N 0.000 claims 1
- AMTSNDJOJYRNDD-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-(dibutylamino)propyl]phenyl]methanone;hydrochloride Chemical compound Cl.C1=CC(CCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)C=C2N1C=CC=C2 AMTSNDJOJYRNDD-UHFFFAOYSA-N 0.000 claims 1
- LNEAGOOADIDYQU-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-(diethylamino)propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCN(CC)CC)C=C1 LNEAGOOADIDYQU-UHFFFAOYSA-N 0.000 claims 1
- QAQRVMPYCRRFPV-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-(dimethylamino)propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCN(C)C)C=C1 QAQRVMPYCRRFPV-UHFFFAOYSA-N 0.000 claims 1
- NGWYONANJAQZPI-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-(dipropylamino)propyl]phenyl]methanone;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCN(CCC)CCC)C=C1 NGWYONANJAQZPI-UHFFFAOYSA-N 0.000 claims 1
- NGBJFHNFQMIRQN-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-(propylamino)propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCNCCC)C=C1 NGBJFHNFQMIRQN-UHFFFAOYSA-N 0.000 claims 1
- NRELSUBAVDXWAM-ZJXXCOCUSA-N (2-butylindolizin-3-yl)-[4-[3-[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C(C=C1)=CC=C1CCCN1C[C@H](C)N(C)[C@H](C)C1 NRELSUBAVDXWAM-ZJXXCOCUSA-N 0.000 claims 1
- OVHUYYLYEPUFLD-WHXBIKBMSA-N (2-butylindolizin-3-yl)-[4-[3-[(3r,5s)-3,5-dimethylpiperazin-1-yl]propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C(C=C1)=CC=C1CCCN1C[C@H](C)N[C@H](C)C1 OVHUYYLYEPUFLD-WHXBIKBMSA-N 0.000 claims 1
- JKAJPYMCIDSFJH-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-[butyl(propyl)amino]propyl]phenyl]methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCN(CCC)CCCC)=CC=C1C(=O)C1=C(CCCC)C=C2N1C=CC=C2 JKAJPYMCIDSFJH-UHFFFAOYSA-N 0.000 claims 1
- CWZVEJZDDJTQNH-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-[cyclopropylmethyl(propyl)amino]propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C(C=C1)=CC=C1CCCN(CCC)CC1CC1 CWZVEJZDDJTQNH-UHFFFAOYSA-N 0.000 claims 1
- VETDLAHVIMUUGJ-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-[ethyl(propyl)amino]propyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCN(CC)CCC)C=C1 VETDLAHVIMUUGJ-UHFFFAOYSA-N 0.000 claims 1
- DKYBVRTXRCICND-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[4-(dibutylamino)butyl]phenyl]methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)C=C2N1C=CC=C2 DKYBVRTXRCICND-UHFFFAOYSA-N 0.000 claims 1
- OCDWPBJEEWOIPX-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[4-(diethylamino)butyl]phenyl]methanone;oxalic acid Chemical compound OC(=O)C(O)=O.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCCN(CC)CC)C=C1 OCDWPBJEEWOIPX-UHFFFAOYSA-N 0.000 claims 1
- FIMFNDMSJIKOAE-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[4-(dipropylamino)butyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCCN(CCC)CCC)C=C1 FIMFNDMSJIKOAE-UHFFFAOYSA-N 0.000 claims 1
- XIMMANMKPGYIGU-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[4-[ethyl(propyl)amino]butyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCCN(CC)CCC)C=C1 XIMMANMKPGYIGU-UHFFFAOYSA-N 0.000 claims 1
- NMPDRKPYIARZCT-UHFFFAOYSA-N (2-ethylindolizin-3-yl)-[4-[3-[ethyl(propyl)amino]propyl]phenyl]methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCN(CC)CCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 NMPDRKPYIARZCT-UHFFFAOYSA-N 0.000 claims 1
- DVQIVNPYDDCYOC-UHFFFAOYSA-N (2-ethylindolizin-3-yl)-[4-[4-[ethyl(propyl)amino]butyl]phenyl]methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCCN(CC)CCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 DVQIVNPYDDCYOC-UHFFFAOYSA-N 0.000 claims 1
- LWYLVHNKNMRGPG-WLHGVMLRSA-N (e)-but-2-enedioic acid;(2-butylindolizin-3-yl)-[4-[3-(dipropylamino)propyl]phenyl]methanone Chemical compound OC(=O)\C=C\C(O)=O.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCN(CCC)CCC)C=C1 LWYLVHNKNMRGPG-WLHGVMLRSA-N 0.000 claims 1
- -1 2-isopropylindolizin-3-yl Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- FVTMVKGVHFIRRA-UHFFFAOYSA-N [4-[3-(dibutylamino)propyl]phenyl]-(2-ethylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 FVTMVKGVHFIRRA-UHFFFAOYSA-N 0.000 claims 1
- HFTLTZBCUJWXGZ-UHFFFAOYSA-N [4-[3-(dibutylamino)propyl]phenyl]-(2-propylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCC)C=C2N1C=CC=C2 HFTLTZBCUJWXGZ-UHFFFAOYSA-N 0.000 claims 1
- HUWKCTZUWUATIK-UHFFFAOYSA-N [4-[3-(diethylamino)propyl]phenyl]-(2-ethylindolizin-3-yl)methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCN(CC)CC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 HUWKCTZUWUATIK-UHFFFAOYSA-N 0.000 claims 1
- XMCXDFCJUNZQLY-UHFFFAOYSA-N [4-[3-(diethylamino)propyl]phenyl]-(2-propylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.CCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCN(CC)CC)C=C1 XMCXDFCJUNZQLY-UHFFFAOYSA-N 0.000 claims 1
- HBHFXEFKYQRTPQ-UHFFFAOYSA-N [4-[3-(dipropylamino)propyl]phenyl]-(2-ethylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCN(CCC)CCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 HBHFXEFKYQRTPQ-UHFFFAOYSA-N 0.000 claims 1
- GGZFCBXCDJSAAH-UHFFFAOYSA-N [4-[3-(dipropylamino)propyl]phenyl]-(2-methylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCN(CCC)CCC)=CC=C1C(=O)C1=C(C)C=C2N1C=CC=C2 GGZFCBXCDJSAAH-UHFFFAOYSA-N 0.000 claims 1
- YBISRJRRQWWAQW-UHFFFAOYSA-N [4-[3-(dipropylamino)propyl]phenyl]-(2-propylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCN(CCC)CCC)=CC=C1C(=O)C1=C(CCC)C=C2N1C=CC=C2 YBISRJRRQWWAQW-UHFFFAOYSA-N 0.000 claims 1
- DWTYPWQJVPSSLD-UHFFFAOYSA-N [4-[3-[bis(2-methoxyethyl)amino]propyl]phenyl]-(2-butylindolizin-3-yl)methanone;oxalic acid Chemical compound OC(=O)C(O)=O.CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCN(CCOC)CCOC)C=C1 DWTYPWQJVPSSLD-UHFFFAOYSA-N 0.000 claims 1
- BNSPGBOQOJARJP-UHFFFAOYSA-N [4-[3-[butyl(ethyl)amino]propyl]phenyl]-(2-butylindolizin-3-yl)methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCN(CC)CCCC)=CC=C1C(=O)C1=C(CCCC)C=C2N1C=CC=C2 BNSPGBOQOJARJP-UHFFFAOYSA-N 0.000 claims 1
- QQANJZJCAUKPSI-UHFFFAOYSA-N [4-[3-[ethyl(propyl)amino]propyl]phenyl]-(2-methylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCN(CC)CCC)=CC=C1C(=O)C1=C(C)C=C2N1C=CC=C2 QQANJZJCAUKPSI-UHFFFAOYSA-N 0.000 claims 1
- QDBHUSLVHSCNDS-UHFFFAOYSA-N [4-[3-[ethyl(propyl)amino]propyl]phenyl]-(2-propan-2-ylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCN(CC)CCC)=CC=C1C(=O)C1=C(C(C)C)C=C2N1C=CC=C2 QDBHUSLVHSCNDS-UHFFFAOYSA-N 0.000 claims 1
- BOEMUZIDTIGAIC-UHFFFAOYSA-N [4-[3-[ethyl(propyl)amino]propyl]phenyl]-(2-propylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCN(CC)CCC)=CC=C1C(=O)C1=C(CCC)C=C2N1C=CC=C2 BOEMUZIDTIGAIC-UHFFFAOYSA-N 0.000 claims 1
- QXWIWTDMWOALLM-UHFFFAOYSA-N [4-[4-(dibutylamino)butyl]phenyl]-(2-ethylindolizin-3-yl)methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 QXWIWTDMWOALLM-UHFFFAOYSA-N 0.000 claims 1
- XBRISISQGFESCE-UHFFFAOYSA-N [4-[4-(dibutylamino)butyl]phenyl]-(2-propylindolizin-3-yl)methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCC)C=C2N1C=CC=C2 XBRISISQGFESCE-UHFFFAOYSA-N 0.000 claims 1
- BTYQHUVRLUJFIV-UHFFFAOYSA-N [4-[4-(diethylamino)butyl]phenyl]-(2-ethylindolizin-3-yl)methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCCN(CC)CC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 BTYQHUVRLUJFIV-UHFFFAOYSA-N 0.000 claims 1
- DFJITGQKHMFYNX-UHFFFAOYSA-N [4-[4-(diethylamino)butyl]phenyl]-(2-propylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.CCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(CCCCN(CC)CC)C=C1 DFJITGQKHMFYNX-UHFFFAOYSA-N 0.000 claims 1
- YVYSDISKYMFAIM-UHFFFAOYSA-N [4-[4-(dipropylamino)butyl]phenyl]-(2-ethylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCCN(CCC)CCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 YVYSDISKYMFAIM-UHFFFAOYSA-N 0.000 claims 1
- HFWMATXNAPKRIW-UHFFFAOYSA-N [4-[4-(dipropylamino)butyl]phenyl]-(2-methylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCCN(CCC)CCC)=CC=C1C(=O)C1=C(C)C=C2N1C=CC=C2 HFWMATXNAPKRIW-UHFFFAOYSA-N 0.000 claims 1
- GVIUAECWEHCIQS-UHFFFAOYSA-N [4-[4-(dipropylamino)butyl]phenyl]-(2-propan-2-ylindolizin-3-yl)methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCCN(CCC)CCC)=CC=C1C(=O)C1=C(C(C)C)C=C2N1C=CC=C2 GVIUAECWEHCIQS-UHFFFAOYSA-N 0.000 claims 1
- WXHSIVYHOXTBMU-UHFFFAOYSA-N [4-[4-(dipropylamino)butyl]phenyl]-(2-propylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCCN(CCC)CCC)=CC=C1C(=O)C1=C(CCC)C=C2N1C=CC=C2 WXHSIVYHOXTBMU-UHFFFAOYSA-N 0.000 claims 1
- MDRRSGAQIYWMCQ-UHFFFAOYSA-N [4-[4-(propylamino)butyl]phenyl]-(2-propylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCCNCCC)=CC=C1C(=O)C1=C(CCC)C=C2N1C=CC=C2 MDRRSGAQIYWMCQ-UHFFFAOYSA-N 0.000 claims 1
- KZHICXCKFDUEDE-UHFFFAOYSA-N [4-[4-[ethyl(propyl)amino]butyl]phenyl]-(2-methylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCCN(CC)CCC)=CC=C1C(=O)C1=C(C)C=C2N1C=CC=C2 KZHICXCKFDUEDE-UHFFFAOYSA-N 0.000 claims 1
- FQMOGAZLIACAOG-UHFFFAOYSA-N [4-[4-[ethyl(propyl)amino]butyl]phenyl]-(2-propan-2-ylindolizin-3-yl)methanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CCCCN(CC)CCC)=CC=C1C(=O)C1=C(C(C)C)C=C2N1C=CC=C2 FQMOGAZLIACAOG-UHFFFAOYSA-N 0.000 claims 1
- RRRNQDUDUMFPTL-UHFFFAOYSA-N [4-[4-[ethyl(propyl)amino]butyl]phenyl]-(2-propylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(CCCCN(CC)CCC)=CC=C1C(=O)C1=C(CCC)C=C2N1C=CC=C2 RRRNQDUDUMFPTL-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 210000000748 cardiovascular system Anatomy 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WTDFFADXONGQOM-UHFFFAOYSA-N formaldehyde;hydrochloride Chemical compound Cl.O=C WTDFFADXONGQOM-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
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Abstract
Indolizinski derivati opće formule (I): ,naznačeni time što: X predstavlja -(CH2)n- radikal, gdje n je cijeli broj od 1 do 6, R1 predstavlja nerazgranati, razgranati ili prstenasti C1-C8 alkilni radikal; Am predstavlja skupinu NR3R4, u kojoj R3 i R4 su istovjetni ili različiti i međusobno neovisno predstavljaju:- atom vodika;- nerazgranati, razgranati ili prstenasti C1-C6 alkilni radikal ili C1-C3 radikal, supstituiran s C3-C6 cikloalkilnim radikalom;- ili (CH2)1-O-B radikal, u kojem B predstavlja atom vodika ili (CH2)k alkilni radikal, gdje l i k su cijeli brojevi, l ? 2 i 1 + k = 6; ili R3 i R4, zajedno s atomom dušika na kojeg su vezani, tvore heterocikl koji sadrži 4 do 6 veza, koji može izborno sadržavati jedan ili više heteroatoma, koje se bira između N i O, i izborno nosi jedan ili više supstituenata, koje se bira između nerazgranatih, razgranatih ili prstenastih C1-C6 alkilnih radikala; R2 predstavlja atom vodika ili nerazgranati, razgranati ili prstenasti C1-C6 alkilni radikal; i njihove farmaceutski prihvatljive soli. Patent sadrži još 14 patentnih zahtjeva.
Claims (15)
1. Indolizinski derivati opće formule (I):
[image]
,
naznačeni time što:
X predstavlja -(CH2)n- radikal, gdje n je cijeli broj od 1 do 6,
R1 predstavlja nerazgranati, razgranati ili prstenasti C1-C8 alkilni radikal;
Am predstavlja skupinu NR3R4, u kojoj R3 i R4 su istovjetni ili različiti i međusobno neovisno predstavljaju:
– atom vodika;
– nerazgranati, razgranati ili prstenasti C1-C6 alkilni radikal ili C1-C3 radikal, supstituiran s C3-C6 cikloalkilnim radikalom;
– ili (CH2)1-O-B radikal, u kojem B predstavlja atom vodika ili (CH2)k alkilni radikal, gdje l i k su cijeli brojevi, l ≥ 2 i 1 + k = 6;
ili R3 i R4, zajedno s atomom dušika na kojeg su vezani, tvore heterocikl koji sadrži 4 do 6 veza, koji može izborno sadržavati jedan ili više heteroatoma, koje se bira između N i O, i izborno nosi jedan ili više supstituenata, koje se bira između nerazgranatih, razgranatih ili prstenastih C1-C6 alkilnih radikala;
R2 predstavlja atom vodika ili nerazgranati, razgranati ili prstenasti C1-C6 alkilni radikal;
i njihove farmaceutski prihvatljive soli.
2. Indolizinski derivati u skladu s patentnim zahtjevom 1, naznačen time što X predstavlja (CH2)n- radikal, gdje n je cijeli broj od 3 to 4.
3. Indolizinski derivati u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R1 predstavlja C1-C4 alkilni radikal.
4. Indolizinski derivati u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što R3 i R4 međusobno neovisno predstavljaju nerazgranati C1-C4 alkilni radikal.
5. Indolizinski derivati u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što R3 i R4 zajedno tvore piperidinilnu ili piperazinilnu skupinu koja izborno nosi jedan ili više metilnih radikala.
6. Indolizinski derivati u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time što R2 predstavlja atom vodika.
7. Indolizinski derivati u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što farmaceutski prihvatljiva sol se bira između oksalata i hidroklorida.
8. Indolizinski derivati formule (I) u skladu s patentnim zahtjevom 1, naznačen time što su to derivati imena:
(2-butilindolizin-3-il)(4-[3-(dietilamino)propil]fenil}metanon-hidroklorid;
(2-etilindolizin-3-il){4-[3-(dietilamino)propil]fenil}metanon-oksalat;
{4-[3-(dietilamino)propil]fenil}(2-propilindolizin-3-il)metanon-hidroklorid;
(2-butilindolizin-3-il){4-[4-(dietilamino)butil]fenil}metanon-oksalat;
{4-[4-(dietilamino)butil]fenil}(2-etilindolizin-3-il)metanon-oksalat;
{4-[4-(dietilamino)butil]fenil}(2-propilindolizin-3-il)metanon-hidroklorid;
(2-butilindolizin-3-il){4-[3-(dipropilamino)propil]fenil}metanon-hidroklorid;
(2-butilindolizin-3-il){4-[3-(dipropilamino)propil]fenil}metanon-hidroklorid hemihidrat;
(2-butilindolizin-3-il){4-[3-(dipropilamino)propil]fenil}metanon-sulfat;
(2-butilindolizin-3-il){4-[3-(dipropilamino)propil]fenil}metanon-fumarat;
{4-[3-(dipropilamino)propil]fenil}(2-etilindolizin-3-il)metanon-hidroklorid;
{4-[3-(dipropilamino)propil]fenil}(2-propilindolizin-3-il)metanon-hidroklorid;
(2-butilindolizin-3-il){4-[4-(dipropilamino)butil]fenil}metanon-hidroklorid;
{4-[4-(dipropilamino)butil]fenil}(2-etilindolizin-3-il)metanon-hidroklorid;
4-[3-(dipropilamino)propil]fenil}(2-izopropilindolizin-3-il)metanon-hidroklorid;
{4-[3-(dipropilamino)propil]fenil}(2-metilindolizin-3-il)metanon-hidroklorid;
{4-[4-(dipropilamino)butil]fenil}(2-izopropilindolizin-3-il)metanon-oksalat;
{4-[4-(dipropilamino)butil]fenil}(2-metilindolizin-3-il)metanon-hidroklorid;
{4-[4-(dipropilamino)butil]fenil}(2-propilindolizin-3-il)metanon-hidroklorid;
(2-butilindolizin-3-il){4-[3-(dibutilamino)propil]fenil}metanon-hidroklorid;
{4-[3-(dibutilamino)propil]fenil}(2-etilindolizin-3-il)metanon-hidroklorid;
{4-[3-(dibutilamino)propil]fenil}(2-propilindolizin-3-il)metanon-hidroklorid;
(2-butilindolizin-3-il){4-[4-(dibutilamino)butil]fenil}metanon-oksalat;
{4-[4-(dibutilamino)butil]fenil}(2-etilindolizin-3-il)metanon-oksalat;
{4-[4-(dibutilamino)butil]fenil}(2-propilindolizin-3-il)metanon-oksalat;
(2-butilindolizin-3-il)(4-{3-[etil(propil)amino]propil}fenil)metanon-hidroklorid;
(2-etilindolizin-3-il)(4-{3-[etil(propil)amino]propil}fenil)metanon-oksalat;
(4-{3-[etil(propil)amino]propil}fenil)(2-izopropilindolizin-3-il)metanon-hidroklorid;
(4-{3-[etil(propil)amino]propil}fenil)(2-metilindolizin-3-il)metanon-hidroklorid;
(4-{4-[etil(propil)amino]butil}fenil)(2-izopropilindolizin-3-il)metanon-oksalat;
(4-{4-[etil(propil)amino]butil}fenil)(2-metilindolizin-3-il)metanon-hidroklorid;
(4-{3-[etil(propil)amino]propil}fenil)(2-propilindolizin-3-il)metanon-hidroklorid;
(2-butilindolizin-3-il)(4-{4-[etil(propil)amino]butil}fenil)metanon-hidroklorid;
(2-etilindolizin-3-il)(4-{4-[etil(propil)amino]butil}fenil)metanon-oksalat;
(4-{4-[etil(propil)amino]butil}fenil)(2-propilindolizin-3-il)metanon-hidroklorid;
(2-butilindolizin-3-il)(4-{3-[butil(propil)amino]propil}fenil)metanon-oksalat;
(4-{3-[butil(etil)amino]propil}fenil)(2-butilindolizin-3-il)metanon-oksalat;
(2-butilindolizin-3-il)(4-{3-[(ciklopropilmetil)(propil)amino]propil}fenil)metanon-hidroklorid;
{4-[4-(propilamino)butil]fenil}(2-propilindolizin-3-il)metanon-hidroklorid;
(2-butilindolizin-3-il){4-[3-(propilamino)propil]fenil}metanon-hidroklorid;
(2-butilindolizin-3-il){4-[3-(dimetilamino)propil]fenil}metanon-hidroklorid;
(2-butilindolizin-3-il)(4-{3-[(3R,5S)-3,5-dimetilpiperazin-1-il]propil}fenil)metanon-hidroklorid;
(2-butilindolizin-3-il)(4-{3-[(3R,5S)-3,4,5-trimetilpiperazin-1-il]propil}fenil)metanon-hidroklorid;
(4-{3-[bis(2-metoksietil)amino]propil}fenil)(2-butilindolizin-3-il)metanon-oksalat;
(2-butilindolizin-3-il)[4-(3-piperidin-1-ilpropil)fenil]metanon-oksalat;
(2-butil-6-metilindolizin-3-il){4-[3-(dipropilamino)propil]fenil}metanon-hidroklorid;
(2-butil-6-etilindolizin-3-il){4-[3-(dipropilamino)propil]fenil}metanon-hidroklorid;
(2-butil-6-metilindolizin-3-il)(4-{3-[etil(propil)amino]propil}fenil)metanon-hidroklorid;
(2-butil-6-etilindolizin-3-il)(4-{3-[etil(propil)amino]propil}fenil)metanon-hidroklorid.
9. Postupak dobivanje derivata formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što se sastoji u reakciji amina H-Am sa spojem formule (II):
[image]
,
u kojoj Y predstavlja atom halogena, a drugi supstituenti su kao što je definirano u prethodnim patentnim zahtjevima.
10. Postupak, naznačen time što je to postupak dobivanja spoja formule (II) u skladu s patentnim zahtjevom 9 i koji se sastoji u reakciji spoja formule (III):
[image]
,
sa spojem formule (IV):
[image]
.
11. Indolizinski derivati opće formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačeni time što su namijenjeni upotrebi kao lijekovi.
12. Lijekovi, naznačeni time što sadrže indolizinske derivate opće formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 8.
13. Farmaceutski ili veterinarski pripravak, naznačen time što sadrži, kao aktivni princip, najmanje jedan indolizinski derivat formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 8, ili njegovu farmaceutski prihvatljivu sol, u kombinaciji s farmaceutskim vehikulumom ili odgovarajućom pomoćnom tvari.
14. Upotreba indolizinskog derivata opće formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačena time što je navedeni indolizinski derivat namijenjen pripravi lijeka namijenjenog liječenju patoloških sindroma kardiovaskularnog sustava, osobito liječenju angine pektoris, hipertenzije, ventrikularne ili supraventrikularne aritmije, liječenju srčane insuficijencije, infarkta miokarda kompliciranog ili ne srčanim insuficijencijama ili sprječavanju postinfarktnog mortaliteta.
15. Upotreba indolizinskog derivata u skladu s patentnim zahtjevom 14 naznačena time što je namijenjena pripravi lijeka za liječenje angine pektoris, hipertenzije, ventrikularne ili supraventrikularne aritmije, liječenje srčane insuficijencije, infarkta miokarda kompliciranog ili ne srčanim insuficijencijama ili sprječavanje postinfarktnog mortaliteta.
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FR0511849A FR2893616B1 (fr) | 2005-11-23 | 2005-11-23 | Nouveaux derives d'indolizine, leur procede de preparation et les compositions therapeutiques les comprenant |
PCT/FR2006/002551 WO2007060318A1 (fr) | 2005-11-23 | 2006-11-21 | Nouveaux derives d'indolizine, leur procede de preparation et les compositions therapeutiques les comprenant. |
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FR2962438B1 (fr) | 2010-07-06 | 2012-08-17 | Sanofi Aventis | Derives d'indolizines, procedes de preparation et application en therapeutique |
FR2962437B1 (fr) | 2010-07-06 | 2012-08-17 | Sanofi Aventis | Derives d'imidazopyridine, leur procede de preparation et leur application en therapeutique |
CN103360390B (zh) * | 2013-07-23 | 2015-06-17 | 东南大学 | 中氮茚甲酰甲基对甲磺酰胺苯乙胺衍生物及其医药用途 |
CN110156776A (zh) * | 2019-04-30 | 2019-08-23 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | 一种c-3芳甲酰基吲嗪类化合物的制备方法 |
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FI61030C (fi) * | 1976-02-19 | 1982-05-10 | Sanofi Sa | Foerfarande foer framstaellning av terapeutiskt verkande 2-substituerade-1- eller 3-benzoyl-indolizinderivat |
FR2665444B1 (fr) * | 1990-08-06 | 1992-11-27 | Sanofi Sa | Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant. |
US5334716A (en) * | 1991-06-17 | 1994-08-02 | Fujisawa Pharmaceutical Co., Ltd. | Heterocyclic derivatives |
US6593322B1 (en) * | 1999-03-17 | 2003-07-15 | Signal Pharmaceuticals, Inc. | Compounds and methods for modulation of estrogen receptors |
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