DE3034001A1 - Isochinolinderivate, verfahren zu ihrer hersellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung - Google Patents
Isochinolinderivate, verfahren zu ihrer hersellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendungInfo
- Publication number
- DE3034001A1 DE3034001A1 DE19803034001 DE3034001A DE3034001A1 DE 3034001 A1 DE3034001 A1 DE 3034001A1 DE 19803034001 DE19803034001 DE 19803034001 DE 3034001 A DE3034001 A DE 3034001A DE 3034001 A1 DE3034001 A1 DE 3034001A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- alkyl
- halogen
- hydrogen
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical class C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000003176 neuroleptic agent Substances 0.000 claims abstract description 3
- 230000000701 neuroleptic effect Effects 0.000 claims abstract description 3
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract 4
- -1 Methylenedioxy Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 239000012059 conventional drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 239000003416 antiarrhythmic agent Substances 0.000 abstract description 2
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 150000002537 isoquinolines Chemical class 0.000 description 5
- CPCMFADZMOYDSZ-UHFFFAOYSA-N 3-chloroisoquinoline Chemical compound C1=CC=C2C=NC(Cl)=CC2=C1 CPCMFADZMOYDSZ-UHFFFAOYSA-N 0.000 description 4
- PJPJVTSCAFZBGN-UHFFFAOYSA-N 3-piperazin-1-ylisoquinoline Chemical compound C1CNCCN1C1=CC2=CC=CC=C2C=N1 PJPJVTSCAFZBGN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000000969 carrier Substances 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
- 238000001816 cooling Methods 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229940025084 amphetamine Drugs 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 210000001715 carotid artery Anatomy 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229950001675 spiperone Drugs 0.000 description 2
- 239000000725 suspension Substances 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
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- JGFHPSNZEUOUCB-UHFFFAOYSA-N 1-(4-fluoro-2-nitrophenyl)-4-(4-isoquinolin-3-ylpiperazin-1-yl)butan-1-one Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC3=CC=CC=C3C=2)CC1 JGFHPSNZEUOUCB-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- CFMSRRKPZHTMEX-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)isoquinoline Chemical compound C1CN(C)CCN1C1=CC2=CC=CC=C2C=N1 CFMSRRKPZHTMEX-UHFFFAOYSA-N 0.000 description 1
- LJFNGMVHMWQQQP-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]isoquinoline Chemical compound COC1=CC=CC=C1N1CCN(C=2N=CC3=CC=CC=C3C=2)CC1 LJFNGMVHMWQQQP-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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
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- 241000124008 Mammalia Species 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- 235000019486 Sunflower oil Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
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- 206010047289 Ventricular extrasystoles Diseases 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
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- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
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- 239000000010 aprotic solvent Substances 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 230000004071 biological effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- 230000001484 cataleptigenic effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 210000001653 corpus striatum Anatomy 0.000 description 1
- 229960000632 dexamfetamine Drugs 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
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- 235000019253 formic acid Nutrition 0.000 description 1
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- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VYCKDIRCVDCQAE-UHFFFAOYSA-N isoquinolin-3-amine Chemical compound C1=CC=C2C=NC(N)=CC2=C1 VYCKDIRCVDCQAE-UHFFFAOYSA-N 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- JMABIVFAGAEUEG-UHFFFAOYSA-N n-(2-chloroethyl)-2-methoxyaniline Chemical compound COC1=CC=CC=C1NCCCl JMABIVFAGAEUEG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JBGFCRCWXGDIFK-UHFFFAOYSA-N naphthalene-1,8-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(S(=O)(=O)O)=CC=CC2=C1 JBGFCRCWXGDIFK-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803034001 DE3034001A1 (de) | 1980-09-10 | 1980-09-10 | Isochinolinderivate, verfahren zu ihrer hersellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung |
| EP81106884A EP0047923B1 (de) | 1980-09-10 | 1981-09-03 | Isochinolinderivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen |
| AT81106884T ATE7389T1 (de) | 1980-09-10 | 1981-09-03 | Isochinolinderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen. |
| DE8181106884T DE3163510D1 (en) | 1980-09-10 | 1981-09-03 | Isoquinoline derivatives, processes for their preparation and pharmaceutical compositions containing them |
| ES505191A ES8206511A1 (es) | 1980-09-10 | 1981-09-04 | Procedimiento para la preparacion de derivados de isoquino- leina |
| JP56139850A JPS5780372A (en) | 1980-09-10 | 1981-09-07 | Isoquinoline derivative and manufacture |
| NZ198308A NZ198308A (en) | 1980-09-10 | 1981-09-08 | Heterocyclic substituted isoquinoline derivatives |
| GR65975A GR74978B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-09-10 | 1981-09-08 | |
| IL63765A IL63765A (en) | 1980-09-10 | 1981-09-08 | Isoquinoline derivatives,a process for their preparation and pharmaceutical formulations containing them |
| FI812783A FI71734C (fi) | 1980-09-10 | 1981-09-08 | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara isokinolinderivat. |
| PT73629A PT73629B (de) | 1980-09-10 | 1981-09-08 | Isochinolinderivate verfahren zu ihrer herstellung sie enthaltende pharmazeutische zubereitungen und ihre verwendung |
| KR1019810003356A KR830007622A (ko) | 1980-09-10 | 1981-09-08 | 이소퀴놀린 유도체의 제조방법 |
| DK400681A DK400681A (da) | 1980-09-10 | 1981-09-09 | Isoquinolinderivater fremgangsmaade til fremstilling deraf samt farmaceutiske praeparater indeholdende disse forbindelser og deres anvendelse |
| HU812595A HU187357B (en) | 1980-09-10 | 1981-09-09 | Process for producing isoquinoline derivatives |
| IE2094/81A IE51551B1 (en) | 1980-09-10 | 1981-09-09 | Isoquinoline derivatives,process for their preparation and pharmaceutical formulations containing them and their use |
| CA000385547A CA1168232A (en) | 1980-09-10 | 1981-09-09 | Isoquinoline derivatives, a process for their preparation, pharmaceutical formulations containing them and their use |
| AU75091/81A AU541976B2 (en) | 1980-09-10 | 1981-09-09 | Isoquinoline derivatives |
| ZA816237A ZA816237B (en) | 1980-09-10 | 1981-09-09 | Isoquinoline derivatives,a process for their preparation pharmaceutical formulations containing them and their use |
| NO813066A NO813066L (no) | 1980-09-10 | 1981-09-09 | Isokinolinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske tilberedninger, innhold og deres anvendelse |
| ES506584A ES8304563A1 (es) | 1980-09-10 | 1981-10-27 | Procedimiento para la preparacion de derivados de isoquino- leina |
| ES506583A ES8305351A1 (es) | 1980-09-10 | 1981-10-27 | Procedimiento para la preparacion de derivados de isoquino- leina |
| PH30299A PH19431A (en) | 1980-09-10 | 1984-02-24 | Isoquinoline derivatives and pharmaceutical composition containing them |
| US06/594,366 US4590273A (en) | 1980-09-10 | 1984-03-28 | Isoquinoline compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803034001 DE3034001A1 (de) | 1980-09-10 | 1980-09-10 | Isochinolinderivate, verfahren zu ihrer hersellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3034001A1 true DE3034001A1 (de) | 1982-04-22 |
Family
ID=6111554
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803034001 Withdrawn DE3034001A1 (de) | 1980-09-10 | 1980-09-10 | Isochinolinderivate, verfahren zu ihrer hersellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung |
| DE8181106884T Expired DE3163510D1 (en) | 1980-09-10 | 1981-09-03 | Isoquinoline derivatives, processes for their preparation and pharmaceutical compositions containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181106884T Expired DE3163510D1 (en) | 1980-09-10 | 1981-09-03 | Isoquinoline derivatives, processes for their preparation and pharmaceutical compositions containing them |
Country Status (20)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4532342A (en) * | 1981-02-20 | 1985-07-30 | Warner-Lambert Company | N-substituted amino acids as intermediates in the preparation of acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| GR79603B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1982-07-24 | 1984-10-31 | Pfizer | |
| DE3244594A1 (de) * | 1982-12-02 | 1984-06-07 | Hoechst Ag, 6230 Frankfurt | 1-phenylisochinolinderivate und verfahren zu ihrer herstellung, diese verbindung enthaltende pharmazeutische praeparate und deren anwendung |
| US4544657A (en) * | 1983-05-19 | 1985-10-01 | Hoffmann-La Roche Inc. | Substituted isoquinolines |
| FR2557570B1 (fr) * | 1984-01-04 | 1986-04-18 | Adir | Nouveaux derives de la quinoleine, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| US4843077A (en) * | 1987-06-09 | 1989-06-27 | Ortho Pharmaceutical Corporation | Isoquinoline derivatives having renal vasodilating properties and/or cardiotonic properties and/or phosphodiesterase inhibiting properties |
| US4883795A (en) * | 1988-01-22 | 1989-11-28 | Pfizer Inc. | Piperazinyl-heterocyclic compounds |
| US5332733A (en) * | 1990-11-24 | 1994-07-26 | Kali-Chemie Pharma Gmbh | Heterocyclically substituted piperazinoakylbenzoxazine and piperazinoalkylbenzothiazine compounds, processes for preparing them, and medicaments containing them |
| US6008352A (en) * | 1997-04-03 | 1999-12-28 | Neurogen Corporation | 1-(isoquinolin-1-yl)-4-(1-phenylmethyl) piperazines; dopamine receptor subtype specific ligands |
| US6313141B1 (en) | 1997-06-13 | 2001-11-06 | Neurogen Corporation | 2-aminoalkylaminoquinolines as dopamine D4 ligands |
| US5972945A (en) * | 1997-06-13 | 1999-10-26 | Neurogen Corporation | 2-aminoalkylaminoquinolines; dopamine receptor subtype specific ligands |
| US6340759B1 (en) | 1997-10-02 | 2002-01-22 | Eisai Co., Ltd. | Fused pyridine derivatives |
| US6040448A (en) | 1997-10-24 | 2000-03-21 | Neurogen Corporation | Certain 1-(2-naphthyl) and 1-(2-azanaphthyl)-4-(1-phenylmethyl) piperazines, dopamine receptor subtype specific ligands |
| DK1027336T3 (da) * | 1997-10-27 | 2005-01-24 | Neurosearch As | Heteroaryldiazacycloalkaner, deres fremstilling og anvendelse |
| US6613901B2 (en) | 2000-03-08 | 2003-09-02 | Neurogen Corporation | 2-aminoalkylaminoquinolines as dopamine D4 ligands |
| WO2008003702A2 (en) * | 2006-07-03 | 2008-01-10 | Vereniging Voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek En Patientenzorg | Fused bicyclic compounds interacting with the histamine h4 receptor |
| MX2013006101A (es) * | 2010-12-17 | 2013-07-02 | Hoffmann La Roche | Compuestos heterociclicos nitrogenados sustituidos fusionados en posicion 6,6 y usos de los mismos. |
| BR112019019555A2 (pt) | 2017-03-30 | 2020-04-22 | Hoffmann La Roche | composto de fórmula i, composição farmacêutica, método de inibição de hpk1, método para melhorar uma resposta imune, método para tratar um distúrbio e uso do composto |
| EP3826722A1 (en) | 2018-07-24 | 2021-06-02 | F. Hoffmann-La Roche AG | Isoquinoline compounds and uses thereof |
| US11612606B2 (en) | 2018-10-03 | 2023-03-28 | Genentech, Inc. | 8-aminoisoquinoline compounds and uses thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3517005A (en) * | 1967-10-26 | 1970-06-23 | Pfizer & Co C | Certain 2- and 4-substituted quinazolines |
| GB1244501A (en) * | 1968-03-09 | 1971-09-02 | Aspro Nicholas Ltd | Heterocyclic amines |
| DE2030675A1 (en) * | 1969-06-23 | 1971-02-11 | Arthur D Little, Inc , Cambridge, Mass (V St A) | 3-amino-4-phenyl-isoquinoline derivs |
| US3932412A (en) * | 1970-12-07 | 1976-01-13 | Sandoz, Inc. | 1-(4-Hydroxyalkylpiperazino)-isoquinoline nitrates |
| DE2420012C3 (de) * | 1974-04-25 | 1980-01-10 | Dr. Karl Thomae Gmbh, 7950 Biberach | Isochinoline |
| AT342057B (de) * | 1974-04-25 | 1978-03-10 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen 3-piperazino-isochinolinen und deren salzen |
| DE2503961C3 (de) * | 1975-01-31 | 1980-02-28 | Dr. Karl Thomae Gmbh, 7950 Biberach | Isochinoline |
| DE2811312A1 (de) * | 1978-03-16 | 1979-09-27 | Hoechst Ag | Neue isochinolinderivate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von arzneimitteln |
| DE2818403A1 (de) * | 1978-04-27 | 1979-11-08 | Hoechst Ag | Neue isochinolinderivate und verfahren zu ihrer herstellung |
| DE2818423A1 (de) * | 1978-04-27 | 1979-11-08 | Hoechst Ag | Neue isochinolinderivate und verfahren zu ihrer herstellung |
-
1980
- 1980-09-10 DE DE19803034001 patent/DE3034001A1/de not_active Withdrawn
-
1981
- 1981-09-03 DE DE8181106884T patent/DE3163510D1/de not_active Expired
- 1981-09-03 AT AT81106884T patent/ATE7389T1/de not_active IP Right Cessation
- 1981-09-03 EP EP81106884A patent/EP0047923B1/de not_active Expired
- 1981-09-04 ES ES505191A patent/ES8206511A1/es not_active Expired
- 1981-09-07 JP JP56139850A patent/JPS5780372A/ja active Pending
- 1981-09-08 PT PT73629A patent/PT73629B/pt unknown
- 1981-09-08 IL IL63765A patent/IL63765A/xx unknown
- 1981-09-08 NZ NZ198308A patent/NZ198308A/en unknown
- 1981-09-08 KR KR1019810003356A patent/KR830007622A/ko not_active Ceased
- 1981-09-08 FI FI812783A patent/FI71734C/fi not_active IP Right Cessation
- 1981-09-08 GR GR65975A patent/GR74978B/el unknown
- 1981-09-09 AU AU75091/81A patent/AU541976B2/en not_active Ceased
- 1981-09-09 HU HU812595A patent/HU187357B/hu unknown
- 1981-09-09 ZA ZA816237A patent/ZA816237B/xx unknown
- 1981-09-09 DK DK400681A patent/DK400681A/da not_active Application Discontinuation
- 1981-09-09 CA CA000385547A patent/CA1168232A/en not_active Expired
- 1981-09-09 IE IE2094/81A patent/IE51551B1/en unknown
- 1981-09-09 NO NO813066A patent/NO813066L/no unknown
- 1981-10-27 ES ES506584A patent/ES8304563A1/es not_active Expired
- 1981-10-27 ES ES506583A patent/ES8305351A1/es not_active Expired
-
1984
- 1984-02-24 PH PH30299A patent/PH19431A/en unknown
- 1984-03-28 US US06/594,366 patent/US4590273A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HU187357B (en) | 1985-12-28 |
| IL63765A0 (en) | 1981-12-31 |
| DK400681A (da) | 1982-03-11 |
| ES506584A0 (es) | 1983-03-01 |
| DE3163510D1 (en) | 1984-06-14 |
| FI71734B (fi) | 1986-10-31 |
| IL63765A (en) | 1985-05-31 |
| IE51551B1 (en) | 1987-01-07 |
| ES506583A0 (es) | 1983-04-01 |
| ES505191A0 (es) | 1982-08-16 |
| FI71734C (fi) | 1987-02-09 |
| JPS5780372A (en) | 1982-05-19 |
| FI812783L (fi) | 1982-03-11 |
| NZ198308A (en) | 1984-03-30 |
| AU541976B2 (en) | 1985-01-31 |
| PT73629A (de) | 1981-10-01 |
| US4590273A (en) | 1986-05-20 |
| ES8304563A1 (es) | 1983-03-01 |
| ZA816237B (en) | 1982-08-25 |
| PT73629B (de) | 1983-04-29 |
| ES8305351A1 (es) | 1983-04-01 |
| NO813066L (no) | 1982-03-11 |
| EP0047923A1 (de) | 1982-03-24 |
| ES8206511A1 (es) | 1982-08-16 |
| PH19431A (en) | 1986-04-15 |
| CA1168232A (en) | 1984-05-29 |
| AU7509181A (en) | 1982-03-18 |
| KR830007622A (ko) | 1983-11-04 |
| ATE7389T1 (de) | 1984-05-15 |
| GR74978B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-07-12 |
| IE812094L (en) | 1982-03-10 |
| EP0047923B1 (de) | 1984-05-09 |
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