HU190019B - Eljárás 8-(alkoxi'karbonil-amino)-4-áril-2-metil-tetrahidro -izokinolin-származékok előállítására - Google Patents
Eljárás 8-(alkoxi'karbonil-amino)-4-áril-2-metil-tetrahidro -izokinolin-származékok előállítására Download PDFInfo
- Publication number
- HU190019B HU190019B HU821799A HU179982A HU190019B HU 190019 B HU190019 B HU 190019B HU 821799 A HU821799 A HU 821799A HU 179982 A HU179982 A HU 179982A HU 190019 B HU190019 B HU 190019B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- priority
- halogen
- june
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- -1 amino compound Chemical class 0.000 claims abstract description 15
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 29
- 239000000460 chlorine Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 206010029897 Obsessive thoughts Diseases 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 3
- 239000003377 acid catalyst Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- UIVAIANIXTWVHO-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(Cl)C=C1 UIVAIANIXTWVHO-UHFFFAOYSA-N 0.000 claims 1
- 239000004166 Lanolin Substances 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 229940039717 lanolin Drugs 0.000 claims 1
- 235000019388 lanolin Nutrition 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 239000000939 antiparkinson agent Substances 0.000 abstract description 2
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000005457 ice water Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MKJIEFSOBYUXJB-UHFFFAOYSA-N 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2CC(CC(C)C)C(=O)CC2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- FQPXAXLGKPKAMF-UHFFFAOYSA-N ethyl n-(2-methyl-4-phenyl-3,4-dihydro-1h-isoquinolin-8-yl)carbamate Chemical compound C1N(C)CC=2C(NC(=O)OCC)=CC=CC=2C1C1=CC=CC=C1 FQPXAXLGKPKAMF-UHFFFAOYSA-N 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 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
- 239000011976 maleic acid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 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
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- MXQPRQPINPBCGD-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl-methylamino]-1-(4-fluorophenyl)ethanol Chemical compound C=1C=CC=C(N)C=1CN(C)CC(O)C1=CC=C(F)C=C1 MXQPRQPINPBCGD-UHFFFAOYSA-N 0.000 description 1
- DVGIYWMJXYCEFJ-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl-methylamino]-1-phenylethanol Chemical compound C=1C=CC=C(N)C=1CN(C)CC(O)C1=CC=CC=C1 DVGIYWMJXYCEFJ-UHFFFAOYSA-N 0.000 description 1
- VOZWXKYLVQXXCK-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=C(Cl)C=C1 VOZWXKYLVQXXCK-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 102000003946 Prolactin Human genes 0.000 description 1
- 108010057464 Prolactin Proteins 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical compound BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 description 1
- 125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- JXOUQHFNABPXOG-UHFFFAOYSA-N ethyl N-[2-[[(2-hydroxy-2-phenylethyl)-methylamino]methyl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC=C1CN(C)CC(O)C1=CC=CC=C1 JXOUQHFNABPXOG-UHFFFAOYSA-N 0.000 description 1
- FPTRJSPPLNSVIB-UHFFFAOYSA-N ethyl n-[4-(4-chlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-yl]carbamate Chemical compound C1N(C)CC=2C(NC(=O)OCC)=CC=CC=2C1C1=CC=C(Cl)C=C1 FPTRJSPPLNSVIB-UHFFFAOYSA-N 0.000 description 1
- MYXXVPPYQMJHGO-UHFFFAOYSA-N ethyl n-[4-(4-chlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-yl]carbamate;hydrochloride Chemical compound Cl.C1N(C)CC=2C(NC(=O)OCC)=CC=CC=2C1C1=CC=C(Cl)C=C1 MYXXVPPYQMJHGO-UHFFFAOYSA-N 0.000 description 1
- LMESQUXRYIHGAS-UHFFFAOYSA-N ethyl n-[4-(4-fluorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-yl]carbamate Chemical compound C1N(C)CC=2C(NC(=O)OCC)=CC=CC=2C1C1=CC=C(F)C=C1 LMESQUXRYIHGAS-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000005454 flavour additive Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Priority Applications (39)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU821799A HU190019B (hu) | 1982-06-04 | 1982-06-04 | Eljárás 8-(alkoxi'karbonil-amino)-4-áril-2-metil-tetrahidro -izokinolin-származékok előállítására |
PH28981A PH19604A (en) | 1982-06-04 | 1983-05-30 | Isoquinoline derivatives and pharmaceutical compositions containing the same |
PL1983249639A PL140164B1 (en) | 1982-06-04 | 1983-06-01 | Process for preparing novel derivatives of 8-carbonylamino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinoline |
PL1983249638A PL140034B1 (en) | 1982-06-04 | 1983-06-01 | Process for preparing novel derivatives of 8-alkoxycarbonyl-amino-4-aryl-3-methyl-1,2,3,4-tetrahydroisoquinoline |
PL1983242311A PL139768B1 (en) | 1982-06-04 | 1983-06-01 | Method of obtaining novel derivatives of 8-aminoacylamino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinoline |
PL1983249636A PL140094B1 (en) | 1982-06-04 | 1983-06-01 | Process for preparing novel derivatives of 8-alkoxycarbonylamino-4-aryl-3-methyl-1,2,3,4-tetrahydroisoquinoline |
PL1983249637A PL140035B1 (en) | 1982-06-04 | 1983-06-01 | Process for preparing novel derivatives of 8-carbonylamino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinoline |
CS833984A CS247164B2 (en) | 1982-06-04 | 1983-06-02 | Method of 8-aminoacylamino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinoline new derivatives production |
AU15340/83A AU566347B2 (en) | 1982-06-04 | 1983-06-02 | Isoquinoline derivatives |
JP58097051A JPS5942369A (ja) | 1982-06-04 | 1983-06-02 | イソキノリン誘導体及びその製造方法、並びに該誘導体を含有する医薬 |
SE8303131A SE8303131L (sv) | 1982-06-04 | 1983-06-02 | Isokinolinderivat |
YU1222/83A YU42865B (en) | 1982-06-04 | 1983-06-02 | Process for obtaining new isoquinoline derivatives |
NL8301960A NL8301960A (nl) | 1982-06-04 | 1983-06-02 | Isochinolinederivaten. |
GR71542A GR77482B (enrdf_load_stackoverflow) | 1982-06-04 | 1983-06-02 | |
FI831982A FI831982A7 (fi) | 1982-06-04 | 1983-06-02 | Isokinoliinijohdannaiset. |
IT8321439A IT1233243B (it) | 1982-06-04 | 1983-06-03 | Derivati dell'isochinolina. |
DK254983A DK254983A (da) | 1982-06-04 | 1983-06-03 | 4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolinderivater eller syreadditionssalte deraf og fremgangsmaade til deres fremstilling |
AT0204383A AT384806B (de) | 1982-06-04 | 1983-06-03 | Verfahren zur herstellung von neuen 4-aryl-2-methyl-1,2,3,4-tetrahydro-isochinolinderivaten und deren salzen |
CA000429646A CA1198733A (en) | 1982-06-04 | 1983-06-03 | Isoquinoline derivatives |
SU833604150A SU1207393A3 (ru) | 1982-06-04 | 1983-06-03 | Способ получени производных изохинолина или их фармацевтически пригодных аддитивных кислых солей |
DE19833320028 DE3320028A1 (de) | 1982-06-04 | 1983-06-03 | 8-amino-4-phenyl-2-methyl-1,2,3,4-tetrahydro-isochinolinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
GB08315293A GB2124209B (en) | 1982-06-04 | 1983-06-03 | Isoquinoline derivatives |
ES522976A ES522976A0 (es) | 1982-06-04 | 1983-06-03 | "procedimiento para la obtencion de nuevos derivados de la 4-aril-2-metil-1,2,3,4-tetrahidro-isoquinolina y de sus sales de adicion acida farmaceuticamente aceptables" |
US06/500,969 US4537895A (en) | 1982-04-04 | 1983-06-03 | Isoquinoline derivatives |
FR8309233A FR2528044B1 (fr) | 1982-06-04 | 1983-06-03 | Derives d'isoquinoleine, leur procede de preparation et medicaments les contenant |
DD83251735A DD210684A5 (de) | 1982-06-04 | 1983-06-03 | Verfahren zur herstellung von neuen isochinolin-derivaten |
CH3048/83A CH654833A5 (de) | 1982-06-04 | 1983-06-03 | 4-aryl-2-methyl-1,2,3,4-tetrahydro-isochinolin-derivate. |
CS841560A CS247177B2 (cs) | 1982-06-04 | 1984-03-05 | Způsob výroby nových derivátů 8-karbamoylamino-4-aryl-2-methyl 1,2,3,4-tetrahydroisochinolinu |
CS841561A CS247178B2 (cs) | 1982-06-04 | 1984-03-05 | Způsob výroby nových derivátů 8-alkoxykarbonylamino-4-aryl2-methyl-1,2,3,4-tetrahydroisochinolinu |
SU843714140A SU1375130A3 (ru) | 1982-06-04 | 1984-03-22 | Способ получени производных изохинолина или их фармацевтически приемлемых аддитивных солей |
SU843713729A SU1329620A3 (ru) | 1982-06-04 | 1984-03-22 | Способ получени производных изохинолина или их фармацевтически пригодных аддитивных кислых солей |
CS846141A CS247182B2 (cs) | 1982-06-04 | 1984-08-13 | Způsob výroby nových derivátů 8-karbamoylamino-4-aryl-2-methyl -1,2,3,4-tetrahydroisochinolinu |
CS848748A CS247188B2 (cs) | 1982-06-04 | 1984-11-16 | Způsob výroby nových derivátů 8-alkoxykarbonylamino-4-aryl-2-methyl-1,2,3,4-tetrahydroisochinolinu |
ES543157A ES8607939A1 (es) | 1982-06-04 | 1985-05-14 | Procedimiento de preparacion de nuevos derivados de la 8-al-coxicarbonilaminoisoquinolina y de sus sales de adicion aci-da |
ES543158A ES8607940A1 (es) | 1982-06-04 | 1985-05-14 | Procedimiento de preparacion de nuevos derivados de la 8-carbamoilaminoisoquinolina y de sus sales de adicion acida |
SU853922993A SU1400505A3 (ru) | 1982-06-04 | 1985-07-10 | Способ получени производных изохинолина или их фармацевтически пригодных аддитивных кислых солей |
YU1554/85A YU43419B (en) | 1982-06-04 | 1985-09-30 | Process for obtaining new izoquinolinic derivatives |
ES551560A ES8702361A1 (es) | 1982-06-04 | 1986-02-01 | Procedimiento de preparacion de nuevos derivados de la 8-carbamoilaminoisoquinolina y de sus sales de adicion acida |
ES551559A ES8701729A1 (es) | 1982-06-04 | 1986-02-01 | Procedimiento de preparacion de nuevos derivados de la 8-alcoxicarbonilamino-isoquinolina y de sus sales de adicion acida |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU821799A HU190019B (hu) | 1982-06-04 | 1982-06-04 | Eljárás 8-(alkoxi'karbonil-amino)-4-áril-2-metil-tetrahidro -izokinolin-származékok előállítására |
Publications (1)
Publication Number | Publication Date |
---|---|
HU190019B true HU190019B (hu) | 1986-08-28 |
Family
ID=10956249
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU821799A HU190019B (hu) | 1982-04-04 | 1982-06-04 | Eljárás 8-(alkoxi'karbonil-amino)-4-áril-2-metil-tetrahidro -izokinolin-származékok előállítására |
Country Status (4)
Country | Link |
---|---|
JP (1) | JPS5942369A (enrdf_load_stackoverflow) |
AU (1) | AU566347B2 (enrdf_load_stackoverflow) |
HU (1) | HU190019B (enrdf_load_stackoverflow) |
IT (1) | IT1233243B (enrdf_load_stackoverflow) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0760566B2 (ja) * | 1986-04-08 | 1995-06-28 | ソニー株式会社 | Fm録再系のノイズ低減回路 |
JPS6476460A (en) * | 1987-09-16 | 1989-03-22 | Canon Kk | Signal processor |
JP2716548B2 (ja) * | 1989-11-01 | 1998-02-18 | 雅昭 廣部 | パーキンソニズム予防・治療剤 |
-
1982
- 1982-06-04 HU HU821799A patent/HU190019B/hu not_active IP Right Cessation
-
1983
- 1983-06-02 JP JP58097051A patent/JPS5942369A/ja active Granted
- 1983-06-02 AU AU15340/83A patent/AU566347B2/en not_active Ceased
- 1983-06-03 IT IT8321439A patent/IT1233243B/it active
Also Published As
Publication number | Publication date |
---|---|
AU1534083A (en) | 1983-12-08 |
JPS5942369A (ja) | 1984-03-08 |
JPS6366315B2 (enrdf_load_stackoverflow) | 1988-12-20 |
AU566347B2 (en) | 1987-10-15 |
IT1233243B (it) | 1992-03-24 |
IT8321439A0 (it) | 1983-06-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3700673A (en) | 3-4-dihydrobenzo(b) (1,7)naphthyridin-1(2h)-ones | |
CA1060445A (en) | Process for preparing quinazoline derivatives | |
CS201040B2 (en) | Method of producing etherified hydroxy-benzo-diheterocyclic compounds | |
CS240954B2 (en) | Preparation method of 1,2-dihydropyridines | |
HU203325B (en) | Process for producing substituted quinazoline derivatives and pharmaceutical compositions containing them | |
IE55798B1 (en) | 2-substituted 4-amino-6,7-dimethoxyquinolines | |
AU598149B2 (en) | 2-((4-piperidyl)methyl)-1,2,3,4-tetrahydroisoquinoline derivatives, their preparation and their application in therapy | |
DK148688B (da) | Analogifremgangsmaade til fremstilling af basisk substituerede 7-alkylteofyllinderivater eller salte deraf med farmaceutisk acceptable syrer | |
FR2540871A1 (fr) | Amino-2 phenyl-5 benzodiazepines-1,3; procede de preparation et medicaments les contenant | |
US5679677A (en) | Heterocyclic carbamates, process for their preparation and medicaments | |
US3314963A (en) | Azabenzocycloalkane-n-carboxamidines | |
EP0093521B1 (en) | Quinoline derivatives | |
IE42978B1 (en) | Triaryl alkyl azabicyclo compounds | |
CA1154015A (en) | Tetrahydroquinoline derivatives, a process for their preparation, their use, and pharmaceutical formulations containing them | |
HU190019B (hu) | Eljárás 8-(alkoxi'karbonil-amino)-4-áril-2-metil-tetrahidro -izokinolin-származékok előállítására | |
CA1207774A (en) | 1-phenylindazol-3-one compounds, a method of preparing them and pharmaceutical compositions containing these compounds | |
JP2003509494A (ja) | ムスカリン拮抗薬 | |
DE2640652A1 (de) | 3-substituierte-(2-hydroxy-3-aminopropoxy)-1,2-benzisoxazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
EP0053017A1 (en) | Amide derivatives | |
SU1375130A3 (ru) | Способ получени производных изохинолина или их фармацевтически приемлемых аддитивных солей | |
US3647802A (en) | 2-amino-4-aryl-3 4-dihydroquinolines | |
KR20010031297A (ko) | 2-치환된 1,2-벤즈이소티아졸 유도체 및 세로토닌 길항제(5-ht1a, 5-ht1b 및 5-ht1d)로서의 그의 용도 | |
FI82249C (fi) | Foerfarande foer framstaellning av nya pyridinderivat. | |
US4221798A (en) | Hypotensive 2-heterocycloamino-imidazolines | |
US3988371A (en) | Meta-[2-(benzylamino)-ethyl] benzoic acid amides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
HU90 | Patent valid on 900628 | ||
HMM4 | Cancellation of final prot. due to non-payment of fee |