LU82427A1 - Nouveaux derives de l'isoquinoleine,leur preparation et les compositions qui les contiennent - Google Patents

Nouveaux derives de l'isoquinoleine,leur preparation et les compositions qui les contiennent Download PDF

Info

Publication number: LU82427A1
Authority: LU; Luxembourg
Prior art keywords: isoquinoline; general formula; product; acid; tetrahydro
Prior art date: 1979-05-09

Application number

LU82427A

Other languages

English (en)

French (fr)

Inventor

D Farge

A Jossin

D Reisdorf

G Ponsinet

Original Assignee

Rhone Poulenc Ind

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

1979-05-09

Filing date

1980-05-08

Publication date

1980-12-16

1980-05-08 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1980-12-16 Publication of LU82427A1 publication Critical patent/LU82427A1/fr

Links

239000000203 mixture Substances 0.000 title claims description 34
238000002360 preparation method Methods 0.000 title claims description 5
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 124
239000000047 product Substances 0.000 claims description 56
-1 benzylthio Chemical group 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 19
238000000034 method Methods 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
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
238000007363 ring formation reaction Methods 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
239000003085 diluting agent 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
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
150000002537 isoquinolines Chemical class 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 19
229910052753 mercury Inorganic materials 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
239000000243 solution 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 12
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
125000001841 imino group Chemical group [H]N=* 0.000 description 10
239000000706 filtrate Substances 0.000 description 9
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000003054 catalyst Substances 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
238000010992 reflux Methods 0.000 description 7
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
229910017604 nitric acid Inorganic materials 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
238000006396 nitration reaction Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Substances ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WADVBDILNXAWNX-UHFFFAOYSA-N 1H-isoquinoline-2-carbothioamide Chemical compound NC(=S)N1CC2=C(C=CC=C2)C=C1 WADVBDILNXAWNX-UHFFFAOYSA-N 0.000 description 4
YETGNODBVXTTEB-UHFFFAOYSA-N 3-(chloromethyl)isoquinoline;hydrochloride Chemical compound Cl.C1=CC=C2C=NC(CCl)=CC2=C1 YETGNODBVXTTEB-UHFFFAOYSA-N 0.000 description 4
208000002193 Pain Diseases 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
230000003110 anti-inflammatory effect Effects 0.000 description 4
239000002585 base Substances 0.000 description 4
150000002540 isothiocyanates Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
AQAAPEKGAKDCPI-UHFFFAOYSA-N 3-(methoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COC)=CC2=C1 AQAAPEKGAKDCPI-UHFFFAOYSA-N 0.000 description 3
DTVYNUOOZIKEEX-UHFFFAOYSA-N 5-aminoisoquinoline Chemical compound N1=CC=C2C(N)=CC=CC2=C1 DTVYNUOOZIKEEX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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
239000002198 insoluble material Substances 0.000 description 3
IYRMNDOLPONSCJ-UHFFFAOYSA-N isoquinolin-2-ium;chloride Chemical compound Cl.C1=NC=CC2=CC=CC=C21 IYRMNDOLPONSCJ-UHFFFAOYSA-N 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
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000377 silicon dioxide Substances 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
GCOXBQRGVWHFTP-UHFFFAOYSA-N 3-(ethoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COCC)=CC2=C1N GCOXBQRGVWHFTP-UHFFFAOYSA-N 0.000 description 2
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 2
OYDIYKSEFZECAG-UHFFFAOYSA-N 3-(octoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCCCCCCCC)=CC2=C1 OYDIYKSEFZECAG-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-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
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
230000001754 anti-pyretic effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 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
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000839 emulsion 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
239000003701 inert diluent Substances 0.000 description 2
125000005956 isoquinolyl group Chemical group 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 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
238000000053 physical method Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000008247 solid mixture Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000126 substance Substances 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
238000002560 therapeutic procedure Methods 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
WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 description 1
JBWYZRJYVQQIPO-UHFFFAOYSA-N 3-(ethoxymethyl)isoquinoline Chemical compound C1=CC=C2C=NC(COCC)=CC2=C1 JBWYZRJYVQQIPO-UHFFFAOYSA-N 0.000 description 1
DKVAXRMXTYMJMQ-UHFFFAOYSA-N 3-(methoxymethyl)isoquinolin-5-amine Chemical compound C1=CC=C2C=NC(COC)=CC2=C1N DKVAXRMXTYMJMQ-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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010002556 Ankylosing Spondylitis Diseases 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
206010058019 Cancer Pain Diseases 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
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
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-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
240000006240 Linum usitatissimum Species 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
239000002202 Polyethylene glycol Substances 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
230000001154 acute effect Effects 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
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000001760 anti-analgesic effect Effects 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
235000014121 butter Nutrition 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
USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
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
208000027866 inflammatory disease Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
XOYMAJLARWXZBA-UHFFFAOYSA-N isoquinoline-3-carbaldehyde Chemical compound C1=CC=C2C=NC(C=O)=CC2=C1 XOYMAJLARWXZBA-UHFFFAOYSA-N 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
NWKYZYGOSPOKDY-UHFFFAOYSA-N n,n-dimethylformamide;pyridine Chemical compound CN(C)C=O.C1=CC=NC=C1 NWKYZYGOSPOKDY-UHFFFAOYSA-N 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
239000002674 ointment Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960005190 phenylalanine Drugs 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 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
230000000552 rheumatic effect Effects 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 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
KRZQYDMOEZDDGE-UHFFFAOYSA-N sodium;octan-1-olate Chemical compound [Na+].CCCCCCCC[O-] KRZQYDMOEZDDGE-UHFFFAOYSA-N 0.000 description 1
239000012265 solid product Substances 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
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
239000003981 vehicle Substances 0.000 description 1
208000009935 visceral pain Diseases 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent 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)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (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)

LU82427A 1979-05-09 1980-05-08 Nouveaux derives de l'isoquinoleine,leur preparation et les compositions qui les contiennent LU82427A1 (fr)

Applications Claiming Priority (2)

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
FR7911706		1979-05-09

Publications (1)

Publication Number	Publication Date
LU82427A1 true LU82427A1 (fr)	1980-12-16

Family

ID=9225233

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82427A LU82427A1 (fr)	1979-05-09	1980-05-08	Nouveaux derives de l'isoquinoleine,leur preparation et les compositions qui les contiennent

Country Status (20)

Country	Link
US (1)	US4261992A (no)
JP (1)	JPS55151593A (no)
AU (1)	AU533935B2 (no)
BE (1)	BE883190A (no)
CA (1)	CA1134360A (no)
CH (1)	CH643852A5 (no)
DE (1)	DE3017865A1 (no)
DK (1)	DK200980A (no)
ES (1)	ES8102144A2 (no)
FI (1)	FI801506A7 (no)
FR (1)	FR2456110A2 (no)
GB (1)	GB2048878B (no)
GR (1)	GR68072B (no)
HU (1)	HU181543B (no)
IT (1)	IT1131167B (no)
LU (1)	LU82427A1 (no)
NL (1)	NL8002538A (no)
NO (1)	NO801360L (no)
SE (1)	SE8003476L (no)
ZA (1)	ZA802703B (no)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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 NL NL8002538A patent/NL8002538A/nl not_active Application Discontinuation
- 1980-05-01 GB GB8014439A patent/GB2048878B/en not_active Expired
- 1980-05-06 GR GR61878A patent/GR68072B/el unknown
- 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
- 1980-05-08 NO NO801360A patent/NO801360L/no unknown
- 1980-05-08 CA CA000351520A patent/CA1134360A/fr not_active Expired
- 1980-05-08 CH CH361080A patent/CH643852A5/fr not_active IP Right Cessation
- 1980-05-08 BE BE0/200531A patent/BE883190A/fr not_active IP Right Cessation
- 1980-05-08 HU HU801138A patent/HU181543B/hu unknown
- 1980-05-08 SE SE8003476A patent/SE8003476L/xx not_active Application Discontinuation
- 1980-05-08 LU LU82427A patent/LU82427A1/fr unknown
- 1980-05-08 DK DK200980A patent/DK200980A/da unknown
- 1980-05-09 FI FI801506A patent/FI801506A7/fi not_active Application Discontinuation
- 1980-05-09 ES ES491336A patent/ES8102144A2/es not_active Expired
- 1980-05-09 IT IT21955/80A patent/IT1131167B/it active
- 1980-05-09 DE DE19803017865 patent/DE3017865A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
AU5815080A (en)	1980-11-13
DK200980A (da)	1980-11-10
ES491336A0 (es)	1980-12-16
HU181543B (en)	1983-10-28
GR68072B (no)	1981-10-29
SE8003476L (sv)	1980-11-10
JPS55151593A (en)	1980-11-26
FI801506A7 (fi)	1980-11-10
NO801360L (no)	1980-11-10
NL8002538A (nl)	1980-11-11
US4261992A (en)	1981-04-14
CA1134360A (fr)	1982-10-26
FR2456110A2 (fr)	1980-12-05
IT1131167B (it)	1986-06-18
ZA802703B (en)	1981-05-27
AU533935B2 (en)	1983-12-22
IT8021955A0 (it)	1980-05-09
CH643852A5 (fr)	1984-06-29
BE883190A (fr)	1980-11-10
GB2048878B (en)	1983-05-18
GB2048878A (en)	1980-12-17
DE3017865A1 (de)	1980-11-20
FR2456110B2 (no)	1982-05-21
ES8102144A2 (es)	1980-12-16

Publication	Publication Date	Title
EP0429366B1 (fr)	1994-03-16	Nouveaux dérivés de l'isoindolone, leur préparation et les compositions pharmaceutiques qui les contiennent
FR2676442A1 (fr)	1992-11-20	Nouveau derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent.
WO1992020685A1 (fr)	1992-11-26	Nouveaux derives du thiopyranopyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0248734B1 (fr)	1989-09-06	Dérivés de benzo[b]thiophène et benzo[b]furannecarboxamides, leurs procédés de préparation et les médicaments les contenant
EP0350403B1 (fr)	1993-01-13	Dérivés de (aza)naphtalènesultame, leurs procédés de préparation et les médicaments les contenant
EP0253711B1 (fr)	1990-05-23	Nouveaux dérivés du 1H,3H-Pyrrolo [1,2-c] thiazole, leur préparation et les Compositions pharmaceutiques qui les contiennent
EP0252823A1 (fr)	1988-01-13	Nouveaux dérivés du 1H, 3H-pyrrolo [1,2-c] thiazole, leur préparation et les compositions pharmaceutiques qui les contiennent
FR2644456A1 (fr)	1990-09-21	Nouveaux derives du 1h, 3h-pyrrolo(1,2-c)thiazolecarboxamide-7, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0533827B1 (fr)	1994-08-24	Nouveaux derives de l'oxazole, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0374041A1 (fr)	1990-06-20	Médicaments à base de dérivés de la benzothiazolamine-2, dérivés et leur préparation
CH633010A5 (fr)	1982-11-15	Derives de l'isoquinoleine, leur preparation et medicament qui les contient.
EP0408437B1 (fr)	1994-06-08	Dérivés d'alkylimino-2 benzothiazoline, leurs procédés de préparation et les médicaments les contenant
CA1112642A (fr)	1981-11-17	Derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent
CA1308715C (fr)	1992-10-13	Derives de la phenothiazine, leur preparation et les compositions qui les contiennent
MC1135A1 (fr)	1977-11-18	Derives de thiazine
EP0233801B1 (fr)	1990-05-23	Nouveaux amides substitués, leur préparation et les compositions pharmaceutiques qui les contiennent
CH626371A5 (no)	1981-11-13
WO1992021664A1 (fr)	1992-12-10	Nouveaux derives de l'oxazole, leur preparation et les compositions qui les contiennent
CH643852A5 (fr)	1984-06-29	Derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent.
WO1992021665A1 (fr)	1992-12-10	Nouveaux derives de l'oxazole et leur preparation
CH643853A5 (fr)	1984-06-29	Derives de l'indole, leur preparation et les medicaments qui les contiennent.
CA1085412A (fr)	1980-09-09	Acides thienothienylcarbonylphenylalcanoiques, leurs derives, leur preparation et les compositions qui les contiennent
EP0027085B1 (fr)	1983-12-14	Nouveaux dérivés de la thiazolo (3,2-c) benzoxazine-1,3, leur préparation et les médicaments qui les contiennent
LU86706A1 (fr)	1987-07-24	Nouveaux derives du benzo(4,5)cyclohepta(1,2-b)thiophene,leur preparation et leur utilisation comme medicaments
EP0728755A1 (fr)	1996-08-28	Nouveaux composés du thiophène, leur procédé de préparation et les compositions pharmaceutiques les renfermant