NZ204608A - Indolizine derivatives and pharmaceutical and veterinary compositions - Google Patents
Indolizine derivatives and pharmaceutical and veterinary compositionsInfo
- Publication number
- NZ204608A NZ204608A NZ204608A NZ20460883A NZ204608A NZ 204608 A NZ204608 A NZ 204608A NZ 204608 A NZ204608 A NZ 204608A NZ 20460883 A NZ20460883 A NZ 20460883A NZ 204608 A NZ204608 A NZ 204608A
- Authority
- NZ
- New Zealand
- Prior art keywords
- indolizine
- oxy
- benzoyl
- propyl
- butylamino
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 13
- 125000003406 indolizinyl group Chemical class C=1(C=CN2C=CC=CC12)* 0.000 title abstract 2
- 239000002253 acid Substances 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000000460 chlorine Chemical group 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 150000002478 indolizines Chemical class 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkyl radical Chemical class 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- SJHYGJLPBDEHIB-UHFFFAOYSA-N [4-[3-(tert-butylamino)propoxy]phenyl]-(2-propan-2-ylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.CC(C)C=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNC(C)(C)C)C=C1 SJHYGJLPBDEHIB-UHFFFAOYSA-N 0.000 claims description 2
- 239000008119 colloidal silica Substances 0.000 claims description 2
- 239000007903 gelatin capsule Substances 0.000 claims description 2
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 2
- WFWMOSNXVLOCBW-UHFFFAOYSA-N (1-bromo-2-butylindolizin-3-yl)-[4-[3-(2,2-dimethylpropylamino)propoxy]phenyl]methanone;hydrobromide Chemical compound Br.CCCCC=1C(Br)=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNCC(C)(C)C)C=C1 WFWMOSNXVLOCBW-UHFFFAOYSA-N 0.000 claims 1
- AVWUBTIIMPKRAW-UHFFFAOYSA-N (1-bromo-2-propan-2-ylindolizin-3-yl)-[4-[3-(tert-butylamino)propoxy]phenyl]methanone;hydrochloride Chemical compound Cl.CC(C)C=1C(Br)=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNC(C)(C)C)C=C1 AVWUBTIIMPKRAW-UHFFFAOYSA-N 0.000 claims 1
- YITFAWLZKOKRCM-UHFFFAOYSA-N BrC=1C(=C(N2C=CC=CC=12)C(C1=CC=C(C=C1)OCCCNC(C)(C)C)=O)CCCC Chemical compound BrC=1C(=C(N2C=CC=CC=12)C(C1=CC=C(C=C1)OCCCNC(C)(C)C)=O)CCCC YITFAWLZKOKRCM-UHFFFAOYSA-N 0.000 claims 1
- BGROYPDVLGWPJT-UHFFFAOYSA-N BrC=1C(=C(N2C=CC=CC=12)C(C1=CC=C(C=C1)OCCNCC(C)(C)C)=O)CCCC Chemical compound BrC=1C(=C(N2C=CC=CC=12)C(C1=CC=C(C=C1)OCCNCC(C)(C)C)=O)CCCC BGROYPDVLGWPJT-UHFFFAOYSA-N 0.000 claims 1
- CGLIWCOWQTZTHF-UHFFFAOYSA-N CC1=CC(=CC(=C1OCCCNC(C)(C)C)C)C(=O)C2=C(C=C3N2C=CC=C3)C(C)C Chemical compound CC1=CC(=CC(=C1OCCCNC(C)(C)C)C)C(=O)C2=C(C=C3N2C=CC=C3)C(C)C CGLIWCOWQTZTHF-UHFFFAOYSA-N 0.000 claims 1
- CGFZGBPUACUMIN-UHFFFAOYSA-N [3-bromo-4-[3-(tert-butylamino)propoxy]phenyl]-(2-propan-2-ylindolizin-3-yl)methanone;hydrochloride Chemical compound Cl.CC(C)C=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNC(C)(C)C)C(Br)=C1 CGFZGBPUACUMIN-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 abstract description 3
- 208000011580 syndromic disease Diseases 0.000 abstract description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 13
- 230000002107 myocardial effect Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- NRTGWAAGLRTUJZ-UHFFFAOYSA-N [4-[3-(dibutylamino)propoxy]phenyl]-(2-ethylindolizin-3-yl)methanone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 NRTGWAAGLRTUJZ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229940127291 Calcium channel antagonist Drugs 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229950007869 butoprozine Drugs 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000002213 calciumantagonistic effect Effects 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 208000005392 Spasm Diseases 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 206010003225 Arteriospasm coronary Diseases 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 208000003890 Coronary Vasospasm Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 201000011634 coronary artery vasospasm Diseases 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 230000028161 membrane depolarization Effects 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000001800 adrenalinergic effect Effects 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 230000009989 contractile response Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000011514 reflex Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- YPDGWBHGBAFJNP-UHFFFAOYSA-N [4-[3-(tert-butylamino)propoxy]phenyl]-(2-ethylindolizin-3-yl)methanone Chemical compound CCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNC(C)(C)C)C=C1 YPDGWBHGBAFJNP-UHFFFAOYSA-N 0.000 description 2
- 230000001466 anti-adreneric effect Effects 0.000 description 2
- 210000000709 aorta Anatomy 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001848 cardiodepressant effect Effects 0.000 description 2
- 150000003943 catecholamines Chemical class 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001595 contractor effect Effects 0.000 description 2
- 230000000916 dilatatory effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000005945 translocation Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RUKSOBDSVFEHOK-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-(ethylamino)propoxy]phenyl]methanone Chemical compound CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNCC)C=C1 RUKSOBDSVFEHOK-UHFFFAOYSA-N 0.000 description 1
- ZFNIDHLEUHLDRX-UHFFFAOYSA-N (2-butylindolizin-3-yl)-[4-[3-(propylamino)propoxy]phenyl]methanone Chemical compound CCCCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNCCC)C=C1 ZFNIDHLEUHLDRX-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- GJWHXWMUGWZNTO-UHFFFAOYSA-N 2,2-dimethylpropane Chemical compound [CH2]C(C)(C)C GJWHXWMUGWZNTO-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 206010006578 Bundle-Branch Block Diseases 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 206010065929 Cardiovascular insufficiency Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 201000001068 Prinzmetal angina Diseases 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- UMWUNJRLZKIFKY-UHFFFAOYSA-N [4-(3-bromopropoxy)phenyl]-(2-ethylindolizin-3-yl)methanone Chemical compound CCC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCBr)C=C1 UMWUNJRLZKIFKY-UHFFFAOYSA-N 0.000 description 1
- PIECJYWNWZZTOI-UHFFFAOYSA-N [4-[2-(tert-butylamino)ethoxy]phenyl]-(2-propan-2-ylindolizin-3-yl)methanone;hydrobromide Chemical compound Br.CC(C)C=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCNC(C)(C)C)C=C1 PIECJYWNWZZTOI-UHFFFAOYSA-N 0.000 description 1
- LCCLZUNDOFDSHX-UHFFFAOYSA-N [4-[3-(2,2-dimethylpropylamino)propoxy]phenyl]-(2-propan-2-ylindolizin-3-yl)methanone Chemical compound CC(C)C=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNCC(C)(C)C)C=C1 LCCLZUNDOFDSHX-UHFFFAOYSA-N 0.000 description 1
- DQTYLPJYPLTIRA-UHFFFAOYSA-N [4-[3-(butylamino)propoxy]phenyl]-(2-ethylindolizin-3-yl)methanone Chemical compound C1=CC(OCCCNCCCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 DQTYLPJYPLTIRA-UHFFFAOYSA-N 0.000 description 1
- QSVLXCJNEFZXHB-UHFFFAOYSA-N [4-[3-(butylamino)propoxy]phenyl]-(2-phenylindolizin-3-yl)methanone Chemical compound C1=CC(OCCCNCCCC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 QSVLXCJNEFZXHB-UHFFFAOYSA-N 0.000 description 1
- LNISQKDLYVROFR-UHFFFAOYSA-N [4-[3-(butylamino)propoxy]phenyl]-(2-propan-2-ylindolizin-3-yl)methanone Chemical compound C1=CC(OCCCNCCCC)=CC=C1C(=O)C1=C(C(C)C)C=C2N1C=CC=C2 LNISQKDLYVROFR-UHFFFAOYSA-N 0.000 description 1
- MLCXHPLXUJNROT-UHFFFAOYSA-N [4-[3-(tert-butylamino)propoxy]phenyl]-(2-butyl-1-chloroindolizin-3-yl)methanone Chemical compound ClC=1C(=C(N2C=CC=CC=12)C(C1=CC=C(C=C1)OCCCNC(C)(C)C)=O)CCCC MLCXHPLXUJNROT-UHFFFAOYSA-N 0.000 description 1
- ZTCMJRLBAJLGHV-UHFFFAOYSA-N [4-[3-(tert-butylamino)propoxy]phenyl]-(2-methylindolizin-3-yl)methanone Chemical compound CC=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNC(C)(C)C)C=C1 ZTCMJRLBAJLGHV-UHFFFAOYSA-N 0.000 description 1
- OKIVYGSIDMENCK-UHFFFAOYSA-N [4-[3-(tert-butylamino)propoxy]phenyl]-(2-phenylindolizin-3-yl)methanone Chemical compound C1=CC(OCCCNC(C)(C)C)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 OKIVYGSIDMENCK-UHFFFAOYSA-N 0.000 description 1
- ZVRBFQSPBKYIAR-UHFFFAOYSA-N [4-[3-(tert-butylamino)propoxy]phenyl]-(2-propan-2-ylindolizin-3-yl)methanone Chemical compound CC(C)C=1C=C2C=CC=CN2C=1C(=O)C1=CC=C(OCCCNC(C)(C)C)C=C1 ZVRBFQSPBKYIAR-UHFFFAOYSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 239000000674 adrenergic antagonist Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003257 anti-anginal effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 210000002376 aorta thoracic Anatomy 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001447 compensatory effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000001435 haemodynamic effect Effects 0.000 description 1
- 230000010247 heart contraction Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012057 packaged powder Substances 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000003087 receptor blocking agent Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 102220322299 rs769382085 Human genes 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000036977 tonic contraction Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000002455 vasospastic effect Effects 0.000 description 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
- 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
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Telephonic Communication Services (AREA)
- Infusion, Injection, And Reservoir Apparatuses (AREA)
- External Artificial Organs (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8210598A FR2528845A1 (fr) | 1982-06-17 | 1982-06-17 | Nouveaux derives d'indolizine, leur procede de preparation ainsi que les compositions therapeutiques les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ204608A true NZ204608A (en) | 1985-09-13 |
Family
ID=9275110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ204608A NZ204608A (en) | 1982-06-17 | 1983-06-16 | Indolizine derivatives and pharmaceutical and veterinary compositions |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4499095A (OSRAM) |
| EP (1) | EP0097636B1 (OSRAM) |
| JP (1) | JPS5980682A (OSRAM) |
| KR (1) | KR870001065B1 (OSRAM) |
| AT (1) | ATE15042T1 (OSRAM) |
| AU (1) | AU553758B2 (OSRAM) |
| BE (1) | BE897059A (OSRAM) |
| CA (1) | CA1195979A (OSRAM) |
| CS (1) | CS240963B2 (OSRAM) |
| DD (1) | DD210046A5 (OSRAM) |
| DE (1) | DE3360609D1 (OSRAM) |
| DK (1) | DK158000C (OSRAM) |
| ES (1) | ES8403900A1 (OSRAM) |
| FI (1) | FI74000C (OSRAM) |
| FR (1) | FR2528845A1 (OSRAM) |
| GR (1) | GR78285B (OSRAM) |
| HU (1) | HU189298B (OSRAM) |
| IE (1) | IE55429B1 (OSRAM) |
| IL (1) | IL68778A (OSRAM) |
| NO (1) | NO159723C (OSRAM) |
| NZ (1) | NZ204608A (OSRAM) |
| PT (1) | PT76876B (OSRAM) |
| SU (1) | SU1194272A3 (OSRAM) |
| YU (1) | YU43313B (OSRAM) |
| ZA (1) | ZA833875B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5215988A (en) * | 1986-02-14 | 1993-06-01 | Sanofi | Aminoalkoxyphenyl derivatives, process of preparation and compositions containing the same |
| FR2642756B1 (fr) * | 1989-02-07 | 1994-03-04 | Sanofi | Derives cycloaminoalkoxyphenyle, leur procede de preparation ainsi que les compositions pharmaceutiques ou veterinaires en contenant |
| FR2642755B1 (OSRAM) * | 1989-02-07 | 1993-11-05 | Sanofi | |
| US5435991A (en) * | 1991-08-09 | 1995-07-25 | Nycomed Innovation Ab | Use of persistent heterocyclic free-radicals in magnetic resonance imaging |
| FR2838123B1 (fr) * | 2002-04-04 | 2005-06-10 | Sanofi Synthelabo | Nouveaux derives d'indolozine-1,2,3 substituee, inhibiteurs selectifs du b-fgf |
| FR2859997B1 (fr) * | 2003-09-18 | 2006-02-03 | Sanofi Synthelabo | Nouveaux derives d'indolizine 1,2,3,6,7,8 substituee, inhibiteurs des fgfs, leur procede de preparation et les compositions pharmaceutiques les contenant. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI61030C (fi) * | 1976-02-19 | 1982-05-10 | Sanofi Sa | Foerfarande foer framstaellning av terapeutiskt verkande 2-substituerade-1- eller 3-benzoyl-indolizinderivat |
| US4378362A (en) * | 1979-12-06 | 1983-03-29 | S.A. Labaz N.V. | Indolizine derivatives and process for preparing the same |
| FR2495616A1 (fr) * | 1980-12-09 | 1982-06-11 | Labaz Nv | Nouveaux derives d'indolizine, leur procede de preparation ainsi que leurs applications en therapeutique |
-
1982
- 1982-06-17 FR FR8210598A patent/FR2528845A1/fr active Granted
-
1983
- 1983-05-25 IL IL68778A patent/IL68778A/xx unknown
- 1983-05-27 ZA ZA833875A patent/ZA833875B/xx unknown
- 1983-06-07 US US06/501,856 patent/US4499095A/en not_active Expired - Fee Related
- 1983-06-07 AU AU15424/83A patent/AU553758B2/en not_active Ceased
- 1983-06-13 GR GR71642A patent/GR78285B/el unknown
- 1983-06-15 DK DK276183A patent/DK158000C/da not_active IP Right Cessation
- 1983-06-15 IE IE1408/83A patent/IE55429B1/en not_active IP Right Cessation
- 1983-06-16 DD DD83252093A patent/DD210046A5/de not_active IP Right Cessation
- 1983-06-16 CA CA000430577A patent/CA1195979A/en not_active Expired
- 1983-06-16 EP EP83870061A patent/EP0097636B1/fr not_active Expired
- 1983-06-16 HU HU832147A patent/HU189298B/hu not_active IP Right Cessation
- 1983-06-16 FI FI832209A patent/FI74000C/fi not_active IP Right Cessation
- 1983-06-16 YU YU1331/83A patent/YU43313B/xx unknown
- 1983-06-16 AT AT83870061T patent/ATE15042T1/de not_active IP Right Cessation
- 1983-06-16 NZ NZ204608A patent/NZ204608A/en unknown
- 1983-06-16 DE DE8383870061T patent/DE3360609D1/de not_active Expired
- 1983-06-16 SU SU833606051A patent/SU1194272A3/ru active
- 1983-06-16 BE BE0/211009A patent/BE897059A/fr not_active IP Right Cessation
- 1983-06-16 PT PT76876A patent/PT76876B/pt not_active IP Right Cessation
- 1983-06-16 NO NO832176A patent/NO159723C/no unknown
- 1983-06-16 CS CS834401A patent/CS240963B2/cs unknown
- 1983-06-17 JP JP58110024A patent/JPS5980682A/ja active Granted
- 1983-06-17 ES ES523389A patent/ES8403900A1/es not_active Expired
- 1983-06-17 KR KR1019830002707A patent/KR870001065B1/ko not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4994474A (en) | Alkyl- or aryl-aminoalkoxy-benzene-sulfonyl indoles | |
| SK5462003A3 (en) | Indolylmaleimide derivatives, method for the preparation thereof and pharmaceutical composition comprising same | |
| CS208153B2 (en) | Method of making the 5-/4-pyridyl/-6-/4-fluorphebyl/-2,3-dihydroimidazo 2,1-b thiazole | |
| IE840655L (en) | 1,3-thiazolidine derivatives | |
| CA3128846A1 (en) | Difluoromethylene compound | |
| IE901665L (en) | Arylthiazolylmethylimidazoles | |
| EP0302792B1 (en) | Alkylaminoalkoxyphenyl derivatives, process of preparation and compositions containing the same | |
| US4575508A (en) | 2-Substituted 1-(3'-aminoalkyl)-1,2,3,4-tetrahydro-β-carbolines, and their use as antiarrhythmic agents | |
| US4950670A (en) | 6-phenyl-3-(piperazinyalalkyl)-2,4(1H,3H)-pyrimidinedione derivatives, their preparation and their application in therapy | |
| NZ204608A (en) | Indolizine derivatives and pharmaceutical and veterinary compositions | |
| EP0173279B1 (en) | 2-(3,5-dialkyl-4-hydroxyphenyl)indole derivatives | |
| US4652565A (en) | Piperazine derivatives, their production and pharmaceutical compositions containing them | |
| US4616017A (en) | Aminohydroxypropoxy substituted aryl compounds | |
| US4588725A (en) | 2-piperazinyl-quinazoline derivatives and pharmaceutical compositions containing them | |
| CS248020B2 (en) | Production method of the (+)-enantiomere or (+-)-racemical 4a,9b-trans-hexahydro-1h-pyridoindole derivatives | |
| PL97275B1 (pl) | Sposob wytwarzania nowych pochodnych tienotriazolodwuazepiny | |
| EP0313288A1 (en) | Imidazole derivatives, process for their preparation and their use as alpha 2-adreno-receptor antagonists | |
| PL115380B1 (en) | Process for preparing novel derivatives of nitropyrrole | |
| CZ112198A3 (cs) | Nové piperazinylalkylthiopyrimidinové deriváty, farmaceutické kompozice obsahující tyto deriváty a způsob přípravy nových sloučenin | |
| GB2086885A (en) | Imidazoles | |
| JP3269658B2 (ja) | フェノール誘導体 | |
| US4681881A (en) | 5-alkoxy-pyrido[4,3-d]pyrimidine derivatives | |
| PL102239B1 (pl) | A process of producing new derivatives of indolysine | |
| US5215988A (en) | Aminoalkoxyphenyl derivatives, process of preparation and compositions containing the same | |
| EP0174833A2 (en) | Triazoloquinoline derivatives |