NO801360L - Isokinolinderivater. - Google Patents
Isokinolinderivater.Info
- Publication number
- NO801360L NO801360L NO801360A NO801360A NO801360L NO 801360 L NO801360 L NO 801360L NO 801360 A NO801360 A NO 801360A NO 801360 A NO801360 A NO 801360A NO 801360 L NO801360 L NO 801360L
- Authority
- NO
- Norway
- Prior art keywords
- prepared
- formula
- general formula
- tetrahydroisoquinoline
- same way
- Prior art date
Links
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 23
- -1 benzylthio group Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 10
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 4
- 239000013067 intermediate product 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
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 2
- 229940006461 iodide ion Drugs 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- 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
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 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
- 239000003921 oil Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 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
- YETGNODBVXTTEB-UHFFFAOYSA-N 3-(chloromethyl)isoquinoline;hydrochloride Chemical compound Cl.C1=CC=C2C=NC(CCl)=CC2=C1 YETGNODBVXTTEB-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000010992 reflux Methods 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
- 239000007787 solid 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
- XRPKRYWVCMDCOS-UHFFFAOYSA-N 3-(2-methoxyethyl)isoquinoline Chemical compound C1=CC=C2C=NC(CCOC)=CC2=C1 XRPKRYWVCMDCOS-UHFFFAOYSA-N 0.000 description 3
- 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 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
- AQAAPEKGAKDCPI-UHFFFAOYSA-N 3-(methoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COC)=CC2=C1 AQAAPEKGAKDCPI-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
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- CMGQQHGOFWZGJH-UHFFFAOYSA-N isoquinolin-3-ylmethanol Chemical compound C1=CC=C2C=NC(CO)=CC2=C1 CMGQQHGOFWZGJH-UHFFFAOYSA-N 0.000 description 3
- XOYMAJLARWXZBA-UHFFFAOYSA-N isoquinoline-3-carbaldehyde Chemical compound C1=CC=C2C=NC(C=O)=CC2=C1 XOYMAJLARWXZBA-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- YARAKSHTBSKLHH-UHFFFAOYSA-N 3-(2-methoxyethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(CCOC)=CC2=C1N YARAKSHTBSKLHH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LPCHRHRDGWYZSG-UHFFFAOYSA-N 3-(butoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COCCCC)=CC2=C1N LPCHRHRDGWYZSG-UHFFFAOYSA-N 0.000 description 2
- VKTSBGGRMFNASN-UHFFFAOYSA-N 3-(butoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCCCC)=CC2=C1 VKTSBGGRMFNASN-UHFFFAOYSA-N 0.000 description 2
- RWMIUVLOQIOJGB-UHFFFAOYSA-N 3-(chloromethyl)isoquinoline Chemical compound C1=CC=C2C=NC(CCl)=CC2=C1 RWMIUVLOQIOJGB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GCOXBQRGVWHFTP-UHFFFAOYSA-N 3-(ethoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COCC)=CC2=C1N GCOXBQRGVWHFTP-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
- SOGSUNMBKQCOQY-UHFFFAOYSA-N 3-(octoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COCCCCCCCC)=CC2=C1N SOGSUNMBKQCOQY-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
- YCTCYOCAZQPOQJ-UHFFFAOYSA-N 3-(propoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COCCC)=CC2=C1N YCTCYOCAZQPOQJ-UHFFFAOYSA-N 0.000 description 2
- FSFHVQNMQAESPS-UHFFFAOYSA-N 3-(propoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCCC)=CC2=C1 FSFHVQNMQAESPS-UHFFFAOYSA-N 0.000 description 2
- PYPHDJNEFGUASN-UHFFFAOYSA-N 3h-isoquinoline-4-thione Chemical compound C1=CC=C2C(=S)CN=CC2=C1 PYPHDJNEFGUASN-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
- 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 2
- NFTSRDOELWKWTK-UHFFFAOYSA-N 5-nitro-3-(propoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCCC)=CC2=C1[N+]([O-])=O NFTSRDOELWKWTK-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
- 241000699670 Mus sp. Species 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
- 241000700159 Rattus Species 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002084 enol ethers Chemical class 0.000 description 2
- 150000002148 esters 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
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002537 isoquinolines Chemical class 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 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
- OCWVONVWBVXUPE-UHFFFAOYSA-N 2-isoquinolin-3-ylethanol Chemical compound C1=CC=C2C=NC(CCO)=CC2=C1 OCWVONVWBVXUPE-UHFFFAOYSA-N 0.000 description 1
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 238000007239 Wittig reaction Methods 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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 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
- 150000002170 ethers Chemical class 0.000 description 1
- BUBWTSJXUHKBBX-UHFFFAOYSA-N ethyl acetate;sodium Chemical compound [Na].CCOC(C)=O BUBWTSJXUHKBBX-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 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
- UREHYSLIWOSYFG-UHFFFAOYSA-N n-[3-(butoxymethyl)isoquinolin-5-yl]-3-(2-hydroxyethyl)-3,4-dihydro-1h-isoquinoline-2-carbothioamide Chemical compound C1C2=CC=CC=C2CC(CCO)N1C(=S)NC1=C2C=C(COCCCC)N=CC2=CC=C1 UREHYSLIWOSYFG-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 102200073741 rs121909602 Human genes 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- KRZQYDMOEZDDGE-UHFFFAOYSA-N sodium;octan-1-olate Chemical compound [Na+].CCCCCCCC[O-] KRZQYDMOEZDDGE-UHFFFAOYSA-N 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| NO801360L true NO801360L (no) | 1980-11-10 |
Family
ID=9225233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801360A NO801360L (no) | 1979-05-09 | 1980-05-08 | Isokinolinderivater. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4261992A (it) |
| JP (1) | JPS55151593A (it) |
| AU (1) | AU533935B2 (it) |
| BE (1) | BE883190A (it) |
| CA (1) | CA1134360A (it) |
| CH (1) | CH643852A5 (it) |
| DE (1) | DE3017865A1 (it) |
| DK (1) | DK200980A (it) |
| ES (1) | ES8102144A2 (it) |
| FI (1) | FI801506A (it) |
| FR (1) | FR2456110A2 (it) |
| GB (1) | GB2048878B (it) |
| GR (1) | GR68072B (it) |
| HU (1) | HU181543B (it) |
| IT (1) | IT1131167B (it) |
| LU (1) | LU82427A1 (it) |
| NL (1) | NL8002538A (it) |
| NO (1) | NO801360L (it) |
| SE (1) | SE8003476L (it) |
| ZA (1) | ZA802703B (it) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA05403A (fr) * | 1975-08-06 | 1981-02-28 | Rhone Poulenc Ind | Nouveaux dérivés de la thiazolo [3,4-b] isoquinoléine et leur procédé de préparation. |
| 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 JP JP5987380A patent/JPS55151593A/ja active Pending
- 1980-05-06 ZA ZA00802703A patent/ZA802703B/xx 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 GR GR61878A patent/GR68072B/el unknown
- 1980-05-08 DK DK200980A patent/DK200980A/da unknown
- 1980-05-08 HU HU801138A patent/HU181543B/hu unknown
- 1980-05-08 CA CA000351520A patent/CA1134360A/fr not_active Expired
- 1980-05-08 LU LU82427A patent/LU82427A1/fr unknown
- 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 SE SE8003476A patent/SE8003476L/xx not_active Application Discontinuation
- 1980-05-08 BE BE0/200531A patent/BE883190A/fr not_active IP Right Cessation
- 1980-05-09 FI FI801506A patent/FI801506A/fi not_active Application Discontinuation
- 1980-05-09 DE DE19803017865 patent/DE3017865A1/de not_active Withdrawn
- 1980-05-09 ES ES491336A patent/ES8102144A2/es not_active Expired
- 1980-05-09 IT IT21955/80A patent/IT1131167B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GR68072B (it) | 1981-10-29 |
| NL8002538A (nl) | 1980-11-11 |
| IT8021955A0 (it) | 1980-05-09 |
| CH643852A5 (fr) | 1984-06-29 |
| ES491336A0 (es) | 1980-12-16 |
| AU5815080A (en) | 1980-11-13 |
| CA1134360A (fr) | 1982-10-26 |
| ES8102144A2 (es) | 1980-12-16 |
| US4261992A (en) | 1981-04-14 |
| AU533935B2 (en) | 1983-12-22 |
| DK200980A (da) | 1980-11-10 |
| LU82427A1 (fr) | 1980-12-16 |
| IT1131167B (it) | 1986-06-18 |
| ZA802703B (en) | 1981-05-27 |
| JPS55151593A (en) | 1980-11-26 |
| FR2456110B2 (it) | 1982-05-21 |
| DE3017865A1 (de) | 1980-11-20 |
| BE883190A (fr) | 1980-11-10 |
| HU181543B (en) | 1983-10-28 |
| GB2048878B (en) | 1983-05-18 |
| FI801506A (fi) | 1980-11-10 |
| SE8003476L (sv) | 1980-11-10 |
| GB2048878A (en) | 1980-12-17 |
| FR2456110A2 (fr) | 1980-12-05 |
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