IL36398A - 3,4-dihydroisoquinoline derivatives,processes for their preparation and pharmaceutical compositions containing the same - Google Patents

3,4-dihydroisoquinoline derivatives,processes for their preparation and pharmaceutical compositions containing the same

Info

Publication number: IL36398A
Authority: IL; Israel
Prior art keywords: dihydroisoquinoline; acid addition; quaternary ammonium; radical; phenyl
Prior art date: 1970-03-12

Application number

IL36398A

Other languages

English (en)

Other versions

IL36398A0 (en

Original Assignee

Rhone Poulenc Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1970-03-12

Filing date

1971-03-11

Publication date

1973-10-25

1971-03-11 Application filed by Rhone Poulenc Sa filed Critical Rhone Poulenc Sa

1971-05-26 Publication of IL36398A0 publication Critical patent/IL36398A0/xx

1973-10-25 Publication of IL36398A publication Critical patent/IL36398A/en

Links

238000000034 method Methods 0.000 title claims description 24
NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 8
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
-1 alkylene radical Chemical class 0.000 claims description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 17
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 7
150000003254 radicals Chemical class 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
VPKAHUMPZYVNIV-UHFFFAOYSA-N 1,4-dihydroisoquinoline Chemical class C1=CC=C2CC=NCC2=C1 VPKAHUMPZYVNIV-UHFFFAOYSA-N 0.000 claims description 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
238000000576 coating method Methods 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000008016 pharmaceutical coating Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000012153 distilled water Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
JNFLSJUGIONDMJ-UHFFFAOYSA-N 2-n,2-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)C(C)CN JNFLSJUGIONDMJ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
230000003226 decolorizating effect Effects 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000000126 substance Substances 0.000 description 4
IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical class C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000008247 solid mixture Substances 0.000 description 3
239000001117 sulphuric acid Substances 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
QJKLPACBLDYFMV-UHFFFAOYSA-N C1(=CC=CC=C1)C1CNC(C2=CC=CC=C12)=S Chemical compound C1(=CC=CC=C1)C1CNC(C2=CC=CC=C12)=S QJKLPACBLDYFMV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
150000002540 isothiocyanates Chemical class 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
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000009736 wetting Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
SFNJUHMQHYRSJI-UHFFFAOYSA-N (1-isothiocyanato-2-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(N=C=S)CC1=CC=CC=C1 SFNJUHMQHYRSJI-UHFFFAOYSA-N 0.000 description 1
HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 description 1
XADXWWLTECVAAE-UHFFFAOYSA-N 1,1-diphenylethanamine Chemical compound C=1C=CC=CC=1C(N)(C)C1=CC=CC=C1 XADXWWLTECVAAE-UHFFFAOYSA-N 0.000 description 1
XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 1
NMKWKTZCPBLCJI-UHFFFAOYSA-N 2,2-diphenylethanamine;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(C[NH3+])C1=CC=CC=C1 NMKWKTZCPBLCJI-UHFFFAOYSA-N 0.000 description 1
HSKBGALULOFBAM-UHFFFAOYSA-N 2,3-dihydroxy-4-methylidene-3h-naphthalene-1-carboxylic acid Chemical class C1=CC=C2C(=C)C(O)C(O)=C(C(O)=O)C2=C1 HSKBGALULOFBAM-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 1
XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
206010048610 Cardiotoxicity Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical class CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
244000166550 Strophanthus gratus Species 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940039750 aconitine Drugs 0.000 description 1
STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
235000001046 cacaotero Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
231100000259 cardiotoxicity Toxicity 0.000 description 1
230000007681 cardiovascular toxicity Effects 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
229960003343 ouabain Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000000053 physical method Methods 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000036279 refractory period Effects 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)

IL36398A 1970-03-12 1971-03-11 3,4-dihydroisoquinoline derivatives,processes for their preparation and pharmaceutical compositions containing the same IL36398A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR707008932A FR2081572B1 (fr)	1970-03-12	1970-03-12

Publications (2)

Publication Number	Publication Date
IL36398A0 IL36398A0 (en)	1971-05-26
IL36398A true IL36398A (en)	1973-10-25

Family

ID=9052168

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL36398A IL36398A (en)	1970-03-12	1971-03-11	3,4-dihydroisoquinoline derivatives,processes for their preparation and pharmaceutical compositions containing the same

Country Status (18)

Country	Link
US (1)	US3759924A (fr)
JP (1)	JPS5341156B1 (fr)
AT (1)	AT303042B (fr)
BE (1)	BE764133A (fr)
CA (1)	CA933928A (fr)
CH (1)	CH521347A (fr)
DE (1)	DE2112026C3 (fr)
DK (1)	DK126000B (fr)
ES (1)	ES389180A1 (fr)
FI (1)	FI49034C (fr)
FR (1)	FR2081572B1 (fr)
GB (1)	GB1285016A (fr)
IE (1)	IE35209B1 (fr)
IL (1)	IL36398A (fr)
NL (1)	NL7102897A (fr)
NO (1)	NO133400C (fr)
SE (1)	SE360655B (fr)
ZA (1)	ZA711602B (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61109470U (fr) *	1984-12-20	1986-07-11
WO1999011622A1 (fr) *	1997-09-03	1999-03-11	Guilford Pharmaceuticals Inc.	Composes aminosubstitues, et procedes et compositions permettant d'inhiber l'activite de la parp
US6635642B1 (en)	1997-09-03	2003-10-21	Guilford Pharmaceuticals Inc.	PARP inhibitors, pharmaceutical compositions comprising same, and methods of using same
US6346536B1 (en)	1997-09-03	2002-02-12	Guilford Pharmaceuticals Inc.	Poly(ADP-ribose) polymerase inhibitors and method for treating neural or cardiovascular tissue damage using the same
US6197785B1 (en)	1997-09-03	2001-03-06	Guilford Pharmaceuticals Inc.	Alkoxy-substituted compounds, methods, and compositions for inhibiting PARP activity
US6426415B1 (en)	1997-09-03	2002-07-30	Guilford Pharmaceuticals Inc.	Alkoxy-substituted compounds, methods and compositions for inhibiting parp activity
US20020028813A1 (en) *	1997-09-03	2002-03-07	Paul F. Jackson	Thioalkyl compounds, methods, and compositions for inhibiting parp activity
US6514983B1 (en)	1997-09-03	2003-02-04	Guilford Pharmaceuticals Inc.	Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage
US6291425B1 (en)	1999-09-01	2001-09-18	Guilford Pharmaceuticals Inc.	Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage
US6395749B1 (en)	1998-05-15	2002-05-28	Guilford Pharmaceuticals Inc.	Carboxamide compounds, methods, and compositions for inhibiting PARP activity
US6387902B1 (en)	1998-12-31	2002-05-14	Guilford Pharmaceuticals, Inc.	Phenazine compounds, methods and pharmaceutical compositions for inhibiting PARP
WO2001090077A1 (fr)	2000-05-19	2001-11-29	Guilford Pharmaceuticals, Inc.	Derives de sulfonamide et de carbamide de 6(5h) phenanthridinones et utilisations de ceux-ci
WO2001091796A2 (fr)	2000-06-01	2001-12-06	Guilford Pharmaceuticals Inc.	Methodes, composes et compositions permettant de traiter la goutte
US6545011B2 (en)	2000-07-13	2003-04-08	Guilford Pharmaceuticals Inc.	Substituted 4,9-dihydrocyclopenta[imn]phenanthridine-5-ones, derivatives thereof and their uses
CN102099036B (zh)	2008-06-03	2015-05-27	英特芒尼公司	用于治疗炎性疾患和纤维化疾患的化合物和方法
AR092742A1 (es) *	2012-10-02	2015-04-29	Intermune Inc	Piridinonas antifibroticas
MX382781B (es)	2014-04-02	2025-03-13	Intermune Inc	Piridinonas anti-fibroticas.

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3227085A (en) *	1963-09-05	1966-01-04	James L Ramer	Shot shell
DE1670694B2 (de) *	1966-05-05	1976-07-22	Hoechst Ag, 6000 Frankfurt	Verfahren zur herstellung von tetrahydroisochinolinen
FR1583755A (fr) *	1968-03-06	1969-12-05
FR2028672A6 (fr) *	1968-03-06	1970-10-16	Rhone Poulenc Sa
GB1244501A (en) *	1968-03-09	1971-09-02	Aspro Nicholas Ltd	Heterocyclic amines

1970
- 1970-03-12 FR FR707008932A patent/FR2081572B1/fr not_active Expired
1971
- 1971-02-12 FI FI710404A patent/FI49034C/fi active
- 1971-03-04 NL NL7102897A patent/NL7102897A/xx not_active Application Discontinuation
- 1971-03-11 CA CA107530A patent/CA933928A/en not_active Expired
- 1971-03-11 ZA ZA711602A patent/ZA711602B/xx unknown
- 1971-03-11 JP JP1285971A patent/JPS5341156B1/ja active Pending
- 1971-03-11 IE IE307/71A patent/IE35209B1/xx unknown
- 1971-03-11 DK DK116471AA patent/DK126000B/da unknown
- 1971-03-11 SE SE03148/71A patent/SE360655B/xx unknown
- 1971-03-11 IL IL36398A patent/IL36398A/en unknown
- 1971-03-11 CH CH359771A patent/CH521347A/fr not_active IP Right Cessation
- 1971-03-11 BE BE764133A patent/BE764133A/fr unknown
- 1971-03-11 US US00123375A patent/US3759924A/en not_active Expired - Lifetime
- 1971-03-11 NO NO925/71A patent/NO133400C/no unknown
- 1971-03-12 ES ES389180A patent/ES389180A1/es not_active Expired
- 1971-03-12 DE DE2112026A patent/DE2112026C3/de not_active Expired
- 1971-03-12 AT AT216171A patent/AT303042B/de not_active IP Right Cessation
- 1971-04-19 GB GB23784/71A patent/GB1285016A/en not_active Expired

Also Published As

Publication number	Publication date
FR2081572B1 (fr)	1973-04-06
ES389180A1 (es)	1973-06-01
DE2112026B2 (de)	1979-03-08
IE35209L (en)	1971-09-12
DK126000B (da)	1973-05-28
SE360655B (fr)	1973-10-01
FR2081572A1 (fr)	1971-12-10
GB1285016A (en)	1972-08-09
DE2112026A1 (de)	1971-09-23
BE764133A (fr)	1971-09-13
DE2112026C3 (de)	1979-10-25
IL36398A0 (en)	1971-05-26
FI49034C (fi)	1975-03-10
CH521347A (fr)	1972-04-15
JPS5341156B1 (fr)	1978-10-31
IE35209B1 (en)	1975-12-10
NO133400C (fr)	1976-04-28
NL7102897A (fr)	1971-09-14
AT303042B (de)	1972-11-10
CA933928A (en)	1973-09-18
ZA711602B (en)	1971-11-24
NO133400B (fr)	1976-01-19
FI49034B (fr)	1974-12-02
US3759924A (en)	1973-09-18

Publication	Publication Date	Title
IL36398A (en)	1973-10-25	3,4-dihydroisoquinoline derivatives,processes for their preparation and pharmaceutical compositions containing the same
NO156525B (no)	1987-06-29	Analogifremgangsmaate ved fremstilling av terapeutisk aktive (3-aminopropoksy)bibenzylderivater.
EP0015156A1 (fr)	1980-09-03	Pyrazoles tricycliques à substitution basique, leur préparation et leur utilisation comme agents anti-inflammatoires
US3644366A (en)	1972-02-22	1-amino-3 4-dihydroisoquinolines
US3898232A (en)	1975-08-05	Isoindolin-1-one derivatives
EP0816338B1 (fr)	2003-02-12	Derives de 3-(bis-phenylmethylene substitue) oxindole
US4001271A (en)	1977-01-04	3-(isopropyl amino alkoxy)-2-phenyl-isoindolin-1-ones
GB1571781A (en)	1980-07-16	Pyridobenzodiazepines
US3822269A (en)	1974-07-02	6-aminoalkylamino-hexahydrophenanthridines useful as antiarrhythmic agents
US4950677A (en)	1990-08-21	Benzimidazole derivative compounds and method of making
US3758691A (en)	1973-09-11	Illness new substituted hydroxyphenyl-alkylamines in the treatment of mental
EP0074741A1 (fr)	1983-03-23	Procédé pour la production d'antagonisme alpha2
EP0299076A1 (fr)	1989-01-18	Compose de 5-hydroxyindole-3-carboxamide et son usage en medecine
PL91000B1 (en)	1977-02-28	Process for the manufacture of indole derivatives [gb1407658a]
EP0136736B1 (fr)	1987-10-28	Dérivés de 1-(4'-alcoylthiophényl)-2-amino-1,3-propanediol-N-substitués
NZ233934A (en)	1992-07-28	Pyridobenzoindole derivatives and pharmaceutical compositions
NO154088B (no)	1986-04-07	Analogifremgangsmaate til fremstilling av terapeutisk aktive tetrahydrokinoliner.
EP0000151B1 (fr)	1981-05-20	Aminoindolines substituées en position 1, procédé de leur production et compositions thérapeutiques les contenant
EP0308059B1 (fr)	1992-09-09	1,2,3,4-Tétrahydroisoquinoléines en tant qu'agents antiarhythmiques
US4189480A (en)	1980-02-19	Isoquinoline derivatives
US3130194A (en)	1964-04-21	Phenthiazine derivatives
US4000306A (en)	1976-12-28	Anti-arrhythmic compositions containing isoindoline derivatives
US4021554A (en)	1977-05-03	1,4-Oxathiino[2,3-c]pyrrole derivatives
US4242346A (en)	1980-12-30	Bis-2N-alkylene tetrahydroisoquinoline compounds
US3455926A (en)	1969-07-15	Phenazine derivatives