NL8002538A - Nieuwe isochinolinederivaten, de bereiding ervan en preparaten, die de nieuwe isochinolinederivaten bevatten. - Google Patents
Nieuwe isochinolinederivaten, de bereiding ervan en preparaten, die de nieuwe isochinolinederivaten bevatten. Download PDFInfo
- Publication number
- NL8002538A NL8002538A NL8002538A NL8002538A NL8002538A NL 8002538 A NL8002538 A NL 8002538A NL 8002538 A NL8002538 A NL 8002538A NL 8002538 A NL8002538 A NL 8002538A NL 8002538 A NL8002538 A NL 8002538A
- Authority
- NL
- Netherlands
- Prior art keywords
- general formula
- formula
- preparation
- acid
- isoquinoline
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 19
- 150000002537 isoquinolines Chemical class 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 benzylthio Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229940086542 triethylamine Drugs 0.000 description 9
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WKACBLSJQCIWIQ-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydroisoquinolin-3-yl)ethanol Chemical compound C1=CC=C2CNC(CCO)CC2=C1 WKACBLSJQCIWIQ-UHFFFAOYSA-N 0.000 description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
- YETGNODBVXTTEB-UHFFFAOYSA-N 3-(chloromethyl)isoquinoline;hydrochloride Chemical compound Cl.C1=CC=C2C=NC(CCl)=CC2=C1 YETGNODBVXTTEB-UHFFFAOYSA-N 0.000 description 5
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HPRDDARZLNDWIN-UHFFFAOYSA-N 3-(2-methoxyethenyl)isoquinoline Chemical compound C1=CC=C2C=NC(C=COC)=CC2=C1 HPRDDARZLNDWIN-UHFFFAOYSA-N 0.000 description 3
- DKVAXRMXTYMJMQ-UHFFFAOYSA-N 3-(methoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COC)=CC2=C1N DKVAXRMXTYMJMQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000000802 nitrating effect Effects 0.000 description 3
- 230000036407 pain Effects 0.000 description 3
- 229960005190 phenylalanine Drugs 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- PBYMYAJONQZORL-UHFFFAOYSA-N 1-methylisoquinoline Chemical compound C1=CC=C2C(C)=NC=CC2=C1 PBYMYAJONQZORL-UHFFFAOYSA-N 0.000 description 2
- XRPKRYWVCMDCOS-UHFFFAOYSA-N 3-(2-methoxyethyl)isoquinoline Chemical compound C1=CC=C2C=NC(CCOC)=CC2=C1 XRPKRYWVCMDCOS-UHFFFAOYSA-N 0.000 description 2
- JBWYZRJYVQQIPO-UHFFFAOYSA-N 3-(ethoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCC)=CC2=C1 JBWYZRJYVQQIPO-UHFFFAOYSA-N 0.000 description 2
- AQAAPEKGAKDCPI-UHFFFAOYSA-N 3-(methoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COC)=CC2=C1 AQAAPEKGAKDCPI-UHFFFAOYSA-N 0.000 description 2
- OYDIYKSEFZECAG-UHFFFAOYSA-N 3-(octoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCCCCCCCC)=CC2=C1 OYDIYKSEFZECAG-UHFFFAOYSA-N 0.000 description 2
- FVVXWRGARUACNW-UHFFFAOYSA-N 3-methylisoquinoline Chemical compound C1=CC=C2C=NC(C)=CC2=C1 FVVXWRGARUACNW-UHFFFAOYSA-N 0.000 description 2
- DTVYNUOOZIKEEX-UHFFFAOYSA-N 5-aminoisoquinoline Chemical compound N1=CC=C2C(N)=CC=CC2=C1 DTVYNUOOZIKEEX-UHFFFAOYSA-N 0.000 description 2
- PJGCFVVNQOYMLP-UHFFFAOYSA-N 5-isothiocyanato-3-(methoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COC)=CC2=C1N=C=S PJGCFVVNQOYMLP-UHFFFAOYSA-N 0.000 description 2
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002084 enol ethers Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- CMGQQHGOFWZGJH-UHFFFAOYSA-N isoquinolin-3-ylmethanol Chemical compound C1=CC=C2C=NC(CO)=CC2=C1 CMGQQHGOFWZGJH-UHFFFAOYSA-N 0.000 description 2
- XOYMAJLARWXZBA-UHFFFAOYSA-N isoquinoline-3-carbaldehyde Chemical compound C1=CC=C2C=NC(C=O)=CC2=C1 XOYMAJLARWXZBA-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000000699 topical 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
- 239000000080 wetting agent Substances 0.000 description 2
- HTWIRGRTEPTBCC-ZJIFWQFVSA-N (3s,4ar,5r,8ar)-5-isothiocyanato-5,8a-dimethyl-3-prop-1-en-2-yl-1,2,3,4,4a,6,7,8-octahydronaphthalene Chemical group C1CC[C@@](C)(N=C=S)[C@@H]2C[C@@H](C(=C)C)CC[C@]21C HTWIRGRTEPTBCC-ZJIFWQFVSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZSKDXMLMMQFHGW-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-3-ylmethanol Chemical compound C1=CC=C2CNC(CO)CC2=C1 ZSKDXMLMMQFHGW-UHFFFAOYSA-N 0.000 description 1
- NFTNPLSNWFYRIS-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-5-ylmethanol Chemical compound C1NCCC2=C1C=CC=C2CO NFTNPLSNWFYRIS-UHFFFAOYSA-N 0.000 description 1
- VDTUSEIYUROSGJ-UHFFFAOYSA-N 1-nitroisoquinoline Chemical compound C1=CC=C2C([N+](=O)[O-])=NC=CC2=C1 VDTUSEIYUROSGJ-UHFFFAOYSA-N 0.000 description 1
- OCWVONVWBVXUPE-UHFFFAOYSA-N 2-isoquinolin-3-ylethanol Chemical compound C1=CC=C2C=NC(CCO)=CC2=C1 OCWVONVWBVXUPE-UHFFFAOYSA-N 0.000 description 1
- LYYRJMVSLBCIDV-UHFFFAOYSA-N 3-(2-methoxyethyl)-5-nitroisoquinoline Chemical compound C1=CC=C2C=NC(CCOC)=CC2=C1[N+]([O-])=O LYYRJMVSLBCIDV-UHFFFAOYSA-N 0.000 description 1
- YARAKSHTBSKLHH-UHFFFAOYSA-N 3-(2-methoxyethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(CCOC)=CC2=C1N YARAKSHTBSKLHH-UHFFFAOYSA-N 0.000 description 1
- LHCSOAWKEHIKDI-UHFFFAOYSA-N 3-(butoxymethyl)-5-isothiocyanatoisoquinoline Chemical compound C1=CC=C2C=NC(COCCCC)=CC2=C1N=C=S LHCSOAWKEHIKDI-UHFFFAOYSA-N 0.000 description 1
- NNMHVJLCGQWNME-UHFFFAOYSA-N 3-(butoxymethyl)-5-nitroisoquinoline Chemical compound C1=CC=C2C=NC(COCCCC)=CC2=C1[N+]([O-])=O NNMHVJLCGQWNME-UHFFFAOYSA-N 0.000 description 1
- LPCHRHRDGWYZSG-UHFFFAOYSA-N 3-(butoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COCCCC)=CC2=C1N LPCHRHRDGWYZSG-UHFFFAOYSA-N 0.000 description 1
- VKTSBGGRMFNASN-UHFFFAOYSA-N 3-(butoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCCCC)=CC2=C1 VKTSBGGRMFNASN-UHFFFAOYSA-N 0.000 description 1
- AHNOQCIJZSSBMN-UHFFFAOYSA-N 3-(ethoxymethyl)-5-nitroisoquinoline Chemical compound C1=CC=C2C=NC(COCC)=CC2=C1[N+]([O-])=O AHNOQCIJZSSBMN-UHFFFAOYSA-N 0.000 description 1
- GCOXBQRGVWHFTP-UHFFFAOYSA-N 3-(ethoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COCC)=CC2=C1N GCOXBQRGVWHFTP-UHFFFAOYSA-N 0.000 description 1
- LXYDZEOPVIGCNC-UHFFFAOYSA-N 3-(methoxymethyl)-5-nitroisoquinoline Chemical compound C1=CC=C2C=NC(COC)=CC2=C1[N+]([O-])=O LXYDZEOPVIGCNC-UHFFFAOYSA-N 0.000 description 1
- SOGSUNMBKQCOQY-UHFFFAOYSA-N 3-(octoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COCCCCCCCC)=CC2=C1N SOGSUNMBKQCOQY-UHFFFAOYSA-N 0.000 description 1
- YCTCYOCAZQPOQJ-UHFFFAOYSA-N 3-(propoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COCCC)=CC2=C1N YCTCYOCAZQPOQJ-UHFFFAOYSA-N 0.000 description 1
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 1
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- AXDZZZFWDXTHAN-UHFFFAOYSA-N 5-isothiocyanato-3-(octoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCCCCCCCC)=CC2=C1N=C=S AXDZZZFWDXTHAN-UHFFFAOYSA-N 0.000 description 1
- JIIDRTRPCSSRDG-UHFFFAOYSA-N 5-isothiocyanato-3-(propoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCCC)=CC2=C1N=C=S JIIDRTRPCSSRDG-UHFFFAOYSA-N 0.000 description 1
- MIACVPZXVFJKPX-UHFFFAOYSA-N 5-nitro-3-(octoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCCCCCCCC)=CC2=C1[N+]([O-])=O MIACVPZXVFJKPX-UHFFFAOYSA-N 0.000 description 1
- PYGMPFQCCWBTJQ-UHFFFAOYSA-N 5-nitroisoquinoline Chemical compound N1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 PYGMPFQCCWBTJQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 240000007124 Brassica oleracea Species 0.000 description 1
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- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 1
- 229930182832 D-phenylalanine Natural products 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 208000015220 Febrile disease Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 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
- 208000007536 Thrombosis Diseases 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- FGEJMPPDXKJWAM-UHFFFAOYSA-L [O-]OOOOOO[O-].[Na+].[Na+] Chemical compound [O-]OOOOOO[O-].[Na+].[Na+] FGEJMPPDXKJWAM-UHFFFAOYSA-L 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000000721 bacterilogical 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
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 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
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000414 obstructive effect Effects 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
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical compound [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 201000005671 spondyloarthropathy Diseases 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7911706 | 1979-05-09 | ||
| FR7911706A FR2456110A2 (fr) | 1979-05-09 | 1979-05-09 | Nouveaux derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8002538A true NL8002538A (nl) | 1980-11-11 |
Family
ID=9225233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8002538A NL8002538A (nl) | 1979-05-09 | 1980-05-01 | Nieuwe isochinolinederivaten, de bereiding ervan en preparaten, die de nieuwe isochinolinederivaten bevatten. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4261992A (enExample) |
| JP (1) | JPS55151593A (enExample) |
| AU (1) | AU533935B2 (enExample) |
| BE (1) | BE883190A (enExample) |
| CA (1) | CA1134360A (enExample) |
| CH (1) | CH643852A5 (enExample) |
| DE (1) | DE3017865A1 (enExample) |
| DK (1) | DK200980A (enExample) |
| ES (1) | ES491336A0 (enExample) |
| FI (1) | FI801506A7 (enExample) |
| FR (1) | FR2456110A2 (enExample) |
| GB (1) | GB2048878B (enExample) |
| GR (1) | GR68072B (enExample) |
| HU (1) | HU181543B (enExample) |
| IT (1) | IT1131167B (enExample) |
| LU (1) | LU82427A1 (enExample) |
| NL (1) | NL8002538A (enExample) |
| NO (1) | NO801360L (enExample) |
| SE (1) | SE8003476L (enExample) |
| ZA (1) | ZA802703B (enExample) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL169076C (nl) * | 1975-08-06 | 1982-06-01 | Rhone Poulenc Ind | Werkwijze voor het bereiden of vervaardigen van farmacologische preparaten met een analgetische en antipyretische werking, alsmede werkwijze voor het bereiden van geneeskrachtige verbindingen, welke geschikt zijn voor gebruik in dergelijke preparaten. |
| SU797580A3 (ru) * | 1977-11-10 | 1981-01-15 | Рон-Пуленк Эндюстри (Фирма) | Способ получени производных изохино-лиНА, иХ СОлЕй, РАцЕМАТОВ или ОпТичЕС-КиХ изОМЕРОВ |
| US4188482A (en) * | 1978-05-04 | 1980-02-12 | Warner-Lambert Company | Thiazino indole compounds |
-
1979
- 1979-05-09 FR FR7911706A patent/FR2456110A2/fr active Granted
-
1980
- 1980-05-01 GB GB8014439A patent/GB2048878B/en not_active Expired
- 1980-05-01 NL NL8002538A patent/NL8002538A/nl not_active Application Discontinuation
- 1980-05-06 ZA ZA00802703A patent/ZA802703B/xx unknown
- 1980-05-06 GR GR61878A patent/GR68072B/el unknown
- 1980-05-06 US US06/147,121 patent/US4261992A/en not_active Expired - Lifetime
- 1980-05-06 AU AU58150/80A patent/AU533935B2/en not_active Expired
- 1980-05-06 JP JP5987380A patent/JPS55151593A/ja active Pending
- 1980-05-08 DK DK200980A patent/DK200980A/da unknown
- 1980-05-08 BE BE0/200531A patent/BE883190A/fr not_active IP Right Cessation
- 1980-05-08 NO NO801360A patent/NO801360L/no unknown
- 1980-05-08 CH CH361080A patent/CH643852A5/fr not_active IP Right Cessation
- 1980-05-08 CA CA000351520A patent/CA1134360A/fr not_active Expired
- 1980-05-08 SE SE8003476A patent/SE8003476L/xx not_active Application Discontinuation
- 1980-05-08 LU LU82427A patent/LU82427A1/fr unknown
- 1980-05-08 HU HU801138A patent/HU181543B/hu unknown
- 1980-05-09 IT IT21955/80A patent/IT1131167B/it active
- 1980-05-09 DE DE19803017865 patent/DE3017865A1/de not_active Withdrawn
- 1980-05-09 ES ES491336A patent/ES491336A0/es active Granted
- 1980-05-09 FI FI801506A patent/FI801506A7/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2048878B (en) | 1983-05-18 |
| LU82427A1 (fr) | 1980-12-16 |
| FR2456110A2 (fr) | 1980-12-05 |
| ZA802703B (en) | 1981-05-27 |
| SE8003476L (sv) | 1980-11-10 |
| US4261992A (en) | 1981-04-14 |
| AU533935B2 (en) | 1983-12-22 |
| IT1131167B (it) | 1986-06-18 |
| GR68072B (enExample) | 1981-10-29 |
| DE3017865A1 (de) | 1980-11-20 |
| GB2048878A (en) | 1980-12-17 |
| FR2456110B2 (enExample) | 1982-05-21 |
| HU181543B (en) | 1983-10-28 |
| ES8102144A2 (es) | 1980-12-16 |
| JPS55151593A (en) | 1980-11-26 |
| CH643852A5 (fr) | 1984-06-29 |
| AU5815080A (en) | 1980-11-13 |
| CA1134360A (fr) | 1982-10-26 |
| BE883190A (fr) | 1980-11-10 |
| IT8021955A0 (it) | 1980-05-09 |
| FI801506A7 (fi) | 1980-11-10 |
| DK200980A (da) | 1980-11-10 |
| ES491336A0 (es) | 1980-12-16 |
| NO801360L (no) | 1980-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |