DE2101691A1 - Isochinolinderivate - Google Patents
IsochinolinderivateInfo
- Publication number
- DE2101691A1 DE2101691A1 DE19712101691 DE2101691A DE2101691A1 DE 2101691 A1 DE2101691 A1 DE 2101691A1 DE 19712101691 DE19712101691 DE 19712101691 DE 2101691 A DE2101691 A DE 2101691A DE 2101691 A1 DE2101691 A1 DE 2101691A1
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydroisoquinoline
- methyl
- trimethoxybenzamido
- chloride
- propyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
- -1 monomethoxyphenyl Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- GRMUBWNQWIFTDO-UHFFFAOYSA-N 2-bromo-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1N(C)CCC2=C1C=CC=C2NC(=O)C1=CC=CC=C1Br GRMUBWNQWIFTDO-UHFFFAOYSA-N 0.000 claims description 3
- ZDBCYZWCAHFMEH-UHFFFAOYSA-N 2-fluoro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1N(C)CCC2=C1C=CC=C2NC(=O)C1=CC=CC=C1F ZDBCYZWCAHFMEH-UHFFFAOYSA-N 0.000 claims description 3
- YHMKLUSDJYAEOL-UHFFFAOYSA-N 3,4-dimethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=CC=CC2=C1CCN(C)C2 YHMKLUSDJYAEOL-UHFFFAOYSA-N 0.000 claims description 3
- HOGNMZSUBOLTHT-UHFFFAOYSA-N 4-methoxy-n-(2-propyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1N(CCC)CCC2=C1C=CC=C2NC(=O)C1=CC=C(OC)C=C1 HOGNMZSUBOLTHT-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- HETTWQGTZQCBHH-UHFFFAOYSA-N 2,6-dimethyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1N(C)CCC2=C1C=CC=C2NC(=O)C1=C(C)C=CC=C1C HETTWQGTZQCBHH-UHFFFAOYSA-N 0.000 claims description 2
- ZBFWEGYLRUCBRW-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(1,2,3,4-tetrahydroisoquinolin-5-yl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C=3CCNCC=3C=CC=2)=C1 ZBFWEGYLRUCBRW-UHFFFAOYSA-N 0.000 claims description 2
- DQTVKTMIXALQNO-UHFFFAOYSA-N 3,4-dimethoxy-n-(2-propyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1N(CCC)CCC2=C1C=CC=C2NC(=O)C1=CC=C(OC)C(OC)=C1 DQTVKTMIXALQNO-UHFFFAOYSA-N 0.000 claims description 2
- CCDXOAZJBOYWLZ-UHFFFAOYSA-N 4-methoxy-n-(1,2,3,4-tetrahydroisoquinolin-5-yl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC2=C1CCNC2 CCDXOAZJBOYWLZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- PLZYEUWLUGOFIW-UHFFFAOYSA-N 2,4,5-trimethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1=C(OC)C(OC)=CC(OC)=C1C(=O)NC1=CC=CC2=C1CCN(C)C2 PLZYEUWLUGOFIW-UHFFFAOYSA-N 0.000 claims 1
- YBAXILSHGYLEHM-UHFFFAOYSA-N 2,6-diethyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound CCC1=CC=CC(CC)=C1C(=O)NC1=CC=CC2=C1CCN(C)C2 YBAXILSHGYLEHM-UHFFFAOYSA-N 0.000 claims 1
- MCZURAQKVIKVME-UHFFFAOYSA-N 2,6-dimethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=CC=CC2=C1CCN(C)C2 MCZURAQKVIKVME-UHFFFAOYSA-N 0.000 claims 1
- NBMVGDLKBKIFCM-UHFFFAOYSA-N 2-chloro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1N(C)CCC2=C1C=CC=C2NC(=O)C1=CC=CC=C1Cl NBMVGDLKBKIFCM-UHFFFAOYSA-N 0.000 claims 1
- NSUOXMUGKJHURE-UHFFFAOYSA-N 2-iodo-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1N(C)CCC2=C1C=CC=C2NC(=O)C1=CC=CC=C1I NSUOXMUGKJHURE-UHFFFAOYSA-N 0.000 claims 1
- RGQIOHMTIBCULG-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-6-yl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C=C3CCN(C)CC3=CC=2)=C1 RGQIOHMTIBCULG-UHFFFAOYSA-N 0.000 claims 1
- YGXQMXOUCICBHU-UHFFFAOYSA-N 3,4-dimethoxy-n-(1,2,3,4-tetrahydroisoquinolin-5-yl)benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=CC=CC2=C1CCNC2 YGXQMXOUCICBHU-UHFFFAOYSA-N 0.000 claims 1
- IZDLNQZZFLQEMP-UHFFFAOYSA-N 4-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC2=C1CCN(C)C2 IZDLNQZZFLQEMP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 14
- OXWNTTVDTPIYRD-UHFFFAOYSA-N 2-methyl-3,4-dihydro-1h-isoquinolin-5-amine Chemical compound C1=CC=C2CN(C)CCC2=C1N OXWNTTVDTPIYRD-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 230000036772 blood pressure Effects 0.000 description 13
- 238000001914 filtration Methods 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 241000700159 Rattus Species 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 9
- DTVYNUOOZIKEEX-UHFFFAOYSA-N 5-aminoisoquinoline Chemical compound N1=CC=C2C(N)=CC=CC2=C1 DTVYNUOOZIKEEX-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- GIIQUGGTGRRQEN-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-8-amine Chemical compound C1CNCC2=C1C=CC=C2N GIIQUGGTGRRQEN-UHFFFAOYSA-N 0.000 description 7
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 6
- 244000309464 bull Species 0.000 description 6
- 229960004486 desoxycorticosterone acetate Drugs 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 235000015497 potassium bicarbonate Nutrition 0.000 description 6
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 6
- 239000011736 potassium bicarbonate Substances 0.000 description 6
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
- 229910003446 platinum oxide Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- SAAFIVJVSQVSSW-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-6-amine Chemical compound C1NCCC2=CC(N)=CC=C21 SAAFIVJVSQVSSW-UHFFFAOYSA-N 0.000 description 4
- VMEDBFRQSKKEEQ-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-7-amine Chemical compound C1CNCC2=CC(N)=CC=C21 VMEDBFRQSKKEEQ-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- GBHVKNBSZXPQDM-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C=3CCN(C)CC=3C=CC=2)=C1 GBHVKNBSZXPQDM-UHFFFAOYSA-N 0.000 description 4
- VIOBGCWEHLRBEP-UHFFFAOYSA-N 3,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1OC VIOBGCWEHLRBEP-UHFFFAOYSA-N 0.000 description 4
- TWQCVIUEUQDOEH-UHFFFAOYSA-N 6-nitroisoquinoline Chemical compound C1=NC=CC2=CC([N+](=O)[O-])=CC=C21 TWQCVIUEUQDOEH-UHFFFAOYSA-N 0.000 description 4
- NYHHIPIPUVLUFF-UHFFFAOYSA-N 7-nitroisoquinoline Chemical compound C1=CN=CC2=CC([N+](=O)[O-])=CC=C21 NYHHIPIPUVLUFF-UHFFFAOYSA-N 0.000 description 4
- SUXMGKFFQJTYEX-UHFFFAOYSA-N 8-nitroisoquinoline Chemical class C1=NC=C2C([N+](=O)[O-])=CC=CC2=C1 SUXMGKFFQJTYEX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000035488 systolic blood pressure Effects 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- KTPIYUVCFSCJQI-UHFFFAOYSA-N 2-propyl-3,4-dihydro-1h-isoquinolin-5-amine;hydrobromide Chemical compound Br.C1=CC=C2CN(CCC)CCC2=C1N KTPIYUVCFSCJQI-UHFFFAOYSA-N 0.000 description 3
- PYGMPFQCCWBTJQ-UHFFFAOYSA-N 5-nitroisoquinoline Chemical compound N1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 PYGMPFQCCWBTJQ-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- NGFCTYXFMDWFRQ-UHFFFAOYSA-N isoquinolin-6-amine Chemical compound C1=NC=CC2=CC(N)=CC=C21 NGFCTYXFMDWFRQ-UHFFFAOYSA-N 0.000 description 3
- DRGUQIQEUWFBDE-UHFFFAOYSA-N isoquinolin-7-amine Chemical compound C1=CN=CC2=CC(N)=CC=C21 DRGUQIQEUWFBDE-UHFFFAOYSA-N 0.000 description 3
- GUSYANXQYUJOBH-UHFFFAOYSA-N isoquinolin-8-amine Chemical compound C1=NC=C2C(N)=CC=CC2=C1 GUSYANXQYUJOBH-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JEPXZNXBEFYVOZ-UHFFFAOYSA-N 2,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(OC)=C(C(Cl)=O)C=C1OC JEPXZNXBEFYVOZ-UHFFFAOYSA-N 0.000 description 2
- QQRITLYBTVMRHT-UHFFFAOYSA-N 2,6-diethylbenzoyl chloride Chemical compound CCC1=CC=CC(CC)=C1C(Cl)=O QQRITLYBTVMRHT-UHFFFAOYSA-N 0.000 description 2
- NDXRPDJVAUCBOH-UHFFFAOYSA-N 2,6-dimethoxybenzoyl chloride Chemical compound COC1=CC=CC(OC)=C1C(Cl)=O NDXRPDJVAUCBOH-UHFFFAOYSA-N 0.000 description 2
- PWHRVVMNFQGSJQ-UHFFFAOYSA-N 2-methyl-3,4-dihydro-1h-isoquinolin-6-amine Chemical compound NC1=CC=C2CN(C)CCC2=C1 PWHRVVMNFQGSJQ-UHFFFAOYSA-N 0.000 description 2
- PXAVAZKTFFJJEU-UHFFFAOYSA-N 2-methyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C1=CC(N)=C2CN(C)CCC2=C1 PXAVAZKTFFJJEU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- METDQAPMXYIBME-UHFFFAOYSA-N n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)-2-nitrobenzamide Chemical compound C1N(C)CCC2=C1C=CC=C2NC(=O)C1=CC=CC=C1[N+]([O-])=O METDQAPMXYIBME-UHFFFAOYSA-N 0.000 description 2
- VNBVEQQVMJQTQH-UHFFFAOYSA-N n-isoquinolin-5-yl-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=CC=CC2=CN=CC=C12 VNBVEQQVMJQTQH-UHFFFAOYSA-N 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- VIBMGJPEMJRFLA-UHFFFAOYSA-N 2,6-dimethyl-n-(1,2,3,4-tetrahydroisoquinolin-5-yl)benzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=CC=CC2=C1CCNC2 VIBMGJPEMJRFLA-UHFFFAOYSA-N 0.000 description 1
- CFLAYISSADVCJH-UHFFFAOYSA-N 2,6-dimethylbenzoyl chloride Chemical compound CC1=CC=CC(C)=C1C(Cl)=O CFLAYISSADVCJH-UHFFFAOYSA-N 0.000 description 1
- PIBCNGJDSHFXFL-UHFFFAOYSA-N 2-bromo-n-(1,2,3,4-tetrahydroisoquinolin-8-yl)benzamide Chemical compound BrC1=CC=CC=C1C(=O)NC1=CC=CC2=C1CNCC2 PIBCNGJDSHFXFL-UHFFFAOYSA-N 0.000 description 1
- JDBAFLGEZOTOPQ-UHFFFAOYSA-N 2-bromo-n-isoquinolin-8-ylbenzamide Chemical compound BrC1=CC=CC=C1C(=O)NC1=CC=CC2=CC=NC=C12 JDBAFLGEZOTOPQ-UHFFFAOYSA-N 0.000 description 1
- NZCKTGCKFJDGFD-UHFFFAOYSA-N 2-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Br NZCKTGCKFJDGFD-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- NVMZPGZYIBQFHV-UHFFFAOYSA-N 2-ethyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C1=CC(N)=C2CN(CC)CCC2=C1 NVMZPGZYIBQFHV-UHFFFAOYSA-N 0.000 description 1
- GZAAOCZROLEMPZ-UHFFFAOYSA-N 2-fluoro-n-(1,2,3,4-tetrahydroisoquinolin-7-yl)benzamide Chemical compound FC1=CC=CC=C1C(=O)NC1=CC=C(CCNC2)C2=C1 GZAAOCZROLEMPZ-UHFFFAOYSA-N 0.000 description 1
- DJDWTEATQGTBGV-UHFFFAOYSA-N 2-fluoro-n-isoquinolin-7-ylbenzamide Chemical compound FC1=CC=CC=C1C(=O)NC1=CC=C(C=CN=C2)C2=C1 DJDWTEATQGTBGV-UHFFFAOYSA-N 0.000 description 1
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- MVIVDSWUOGNODP-UHFFFAOYSA-N 2-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1I MVIVDSWUOGNODP-UHFFFAOYSA-N 0.000 description 1
- WKCGLLFXFQEUEP-UHFFFAOYSA-N 2-nitro-n-(1,2,3,4-tetrahydroisoquinolin-6-yl)benzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NC1=CC=C(CNCC2)C2=C1 WKCGLLFXFQEUEP-UHFFFAOYSA-N 0.000 description 1
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
- XMJUYBUOFXNDGN-UHFFFAOYSA-N 3,4-dimethoxy-n-(1,2,3,4-tetrahydroisoquinolin-5-yl)benzamide;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1C(=O)NC1=CC=CC2=C1CCNC2 XMJUYBUOFXNDGN-UHFFFAOYSA-N 0.000 description 1
- DAUAQNGYDSHRET-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC DAUAQNGYDSHRET-UHFFFAOYSA-N 0.000 description 1
- WWHJLVMBXXXUFO-UHFFFAOYSA-N 4-(chloromethyl)-1,2-dimethoxybenzene Chemical compound COC1=CC=C(CCl)C=C1OC WWHJLVMBXXXUFO-UHFFFAOYSA-N 0.000 description 1
- RWEHJPJVLZAECD-UHFFFAOYSA-N 4-methoxy-n-(1,2,3,4-tetrahydroisoquinolin-8-yl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC2=C1CNCC2 RWEHJPJVLZAECD-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GPVDHNVGGIAOQT-UHFFFAOYSA-N Veratric acid Natural products COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- QIRBMSOXLZPSLY-UHFFFAOYSA-N n-isoquinolin-5-yl-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=CC=CC2=CN=CC=C12 QIRBMSOXLZPSLY-UHFFFAOYSA-N 0.000 description 1
- JKEUIIVBDXPLSR-UHFFFAOYSA-N n-isoquinolin-5-yl-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C3=CC=NC=C3C=CC=2)=C1 JKEUIIVBDXPLSR-UHFFFAOYSA-N 0.000 description 1
- KFHGBPIRWMBMBV-UHFFFAOYSA-N n-isoquinolin-5-yl-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC2=CN=CC=C12 KFHGBPIRWMBMBV-UHFFFAOYSA-N 0.000 description 1
- BFZHCYALXOPQQG-UHFFFAOYSA-N n-isoquinolin-6-yl-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=CC=C(C=NC=C2)C2=C1 BFZHCYALXOPQQG-UHFFFAOYSA-N 0.000 description 1
- BDRLUVPYYHWOOP-UHFFFAOYSA-N n-isoquinolin-8-yl-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC2=CC=NC=C12 BDRLUVPYYHWOOP-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 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
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7090070A | 1970-09-09 | 1970-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2101691A1 true DE2101691A1 (de) | 1972-03-16 |
Family
ID=22098044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712101691 Pending DE2101691A1 (de) | 1970-09-09 | 1971-01-15 | Isochinolinderivate |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4824396B1 (enExample) |
| BE (1) | BE763149R (enExample) |
| CH (1) | CH550797A (enExample) |
| DE (1) | DE2101691A1 (enExample) |
| FR (1) | FR2106399B2 (enExample) |
| GB (1) | GB1312205A (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999021836A1 (en) * | 1997-10-24 | 1999-05-06 | Smithkline Beecham Plc | Substituted isoquinoline derivatives and their use as anticonvulsants |
| WO2003068749A1 (en) * | 2002-02-15 | 2003-08-21 | Glaxo Group Limited | Vanilloid receptor modulators |
| US6841560B2 (en) * | 1997-03-18 | 2005-01-11 | Smithkline Beecham P.L.C. | Substituted isoquinoline derivatives and their use as anticonvulsants |
| US8003663B2 (en) | 2006-08-01 | 2011-08-23 | Glaxo Group Limited | Pyrazolo[3,4-b]pyridine compounds, and their use as PDE4 inhibitors |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50123994U (enExample) * | 1974-03-26 | 1975-10-09 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3674791A (en) * | 1968-03-26 | 1972-07-04 | Marion Laboratories Inc | Benzamido 2 lower alkyl decahydroisoquinolines |
-
1970
- 1970-12-28 JP JP11953270A patent/JPS4824396B1/ja active Pending
-
1971
- 1971-01-15 DE DE19712101691 patent/DE2101691A1/de active Pending
- 1971-02-18 BE BE763149A patent/BE763149R/xx active
- 1971-05-17 CH CH732371A patent/CH550797A/xx not_active IP Right Cessation
- 1971-06-01 GB GB1832071A patent/GB1312205A/en not_active Expired
- 1971-09-08 FR FR7132410A patent/FR2106399B2/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6841560B2 (en) * | 1997-03-18 | 2005-01-11 | Smithkline Beecham P.L.C. | Substituted isoquinoline derivatives and their use as anticonvulsants |
| WO1999021836A1 (en) * | 1997-10-24 | 1999-05-06 | Smithkline Beecham Plc | Substituted isoquinoline derivatives and their use as anticonvulsants |
| WO2003068749A1 (en) * | 2002-02-15 | 2003-08-21 | Glaxo Group Limited | Vanilloid receptor modulators |
| EP2033953A1 (en) * | 2002-02-15 | 2009-03-11 | Glaxo Group Limited | Vanilloid receptor modulators |
| US7538121B2 (en) | 2002-02-15 | 2009-05-26 | Glaxo Group Limited | Vanilloid receptor modulators |
| US8003663B2 (en) | 2006-08-01 | 2011-08-23 | Glaxo Group Limited | Pyrazolo[3,4-b]pyridine compounds, and their use as PDE4 inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2106399A2 (enExample) | 1972-05-05 |
| BE763149R (fr) | 1971-07-16 |
| GB1312205A (en) | 1973-04-04 |
| CH550797A (de) | 1974-06-28 |
| FR2106399B2 (enExample) | 1974-10-18 |
| JPS4824396B1 (enExample) | 1973-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |