CH644848A5 - Isoquinoline derivatives and their preparation - Google Patents

Isoquinoline derivatives and their preparation Download PDF

Info

Publication number: CH644848A5
Authority: CH; Switzerland
Prior art keywords: dimethoxy; radical; phenyl; isoquinoline; och
Prior art date: 1979-07-19

Application number

CH520780A

Other languages

English (en)

French (fr)

Inventor

Andre Buzas

Original Assignee

Andre Buzas

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.)

1979-07-19

Filing date

1980-07-08

Publication date

1984-08-31

1980-07-08 Application filed by Andre Buzas filed Critical Andre Buzas

1984-08-31 Publication of CH644848A5 publication Critical patent/CH644848A5/fr

Links

238000002360 preparation method Methods 0.000 title claims description 4
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 37
-1 alkyl radical Chemical class 0.000 claims description 23
238000000034 method Methods 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
230000000747 cardiac effect Effects 0.000 claims description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
150000002537 isoquinolines Chemical class 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 6
125000000217 alkyl group Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 1
230000002792 vascular Effects 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
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 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 17
229930008281 A03AD01 - Papaverine Natural products 0.000 description 16
229960001789 papaverine Drugs 0.000 description 16
239000000243 solution Substances 0.000 description 15
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
101150041968 CDC13 gene Proteins 0.000 description 11
IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
229960001989 prenylamine Drugs 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
239000002808 molecular sieve Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
238000009835 boiling Methods 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
230000009471 action Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
230000009467 reduction Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 3
229930182837 (R)-adrenaline Natural products 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000010323 ascorbic acid Nutrition 0.000 description 3
229960005070 ascorbic acid Drugs 0.000 description 3
239000011668 ascorbic acid Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229960005139 epinephrine Drugs 0.000 description 3
239000000284 extract Substances 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 3
229960002748 norepinephrine Drugs 0.000 description 3
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
QJTBIAMBPGGIGI-UHFFFAOYSA-N Papaveraldine Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)C1=NC=CC2=CC(OC)=C(OC)C=C12 QJTBIAMBPGGIGI-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000003288 anthiarrhythmic effect Effects 0.000 description 2
208000008784 apnea Diseases 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000000004 hemodynamic effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
230000021962 pH elevation Effects 0.000 description 2
230000036581 peripheral resistance Effects 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000012360 testing method Methods 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-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
DBKSSENEKWOVKL-UHFFFAOYSA-N 4-(methylamino)butan-1-ol Chemical compound CNCCCCO DBKSSENEKWOVKL-UHFFFAOYSA-N 0.000 description 1
206010002660 Anoxia Diseases 0.000 description 1
241000976983 Anoxia Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 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
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 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
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001919 adrenal effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000007953 anoxia Effects 0.000 description 1
239000003416 antiarrhythmic agent Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit 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
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
206010061592 cardiac fibrillation Diseases 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003218 coronary vasodilator agent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002600 fibrillogenic effect Effects 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000005240 left ventricle Anatomy 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
TXTHKGMZDDTZFD-UHFFFAOYSA-N n-cyclohexylaniline Chemical compound C1CCCCC1NC1=CC=CC=C1 TXTHKGMZDDTZFD-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000810 peripheral vasodilating agent Substances 0.000 description 1
229960002116 peripheral vasodilator Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 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
238000002560 therapeutic procedure Methods 0.000 description 1

Classifications

- 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
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
- 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
- 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
- A61P9/06—Antiarrhythmics

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Saccharide Compounds (AREA)

CH520780A 1979-07-19 1980-07-08 Isoquinoline derivatives and their preparation CH644848A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7925276		1979-07-19

Publications (1)

Publication Number	Publication Date
CH644848A5 true CH644848A5 (en)	1984-08-31

Family

ID=10506637

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH520780A CH644848A5 (en)	1979-07-19	1980-07-08	Isoquinoline derivatives and their preparation

Country Status (28)

Country	Link
JP (1)	JPS5618964A (de)
AR (1)	AR228953A1 (de)
AT (1)	AT375649B (de)
AU (1)	AU538065B2 (de)
BE (1)	BE884242A (de)
CA (1)	CA1152998A (de)
CH (1)	CH644848A5 (de)
DE (1)	DE3027338C2 (de)
DK (1)	DK152124C (de)
EG (1)	EG14616A (de)
ES (1)	ES8106500A1 (de)
FI (1)	FI77027C (de)
FR (2)	FR2461497A1 (de)
GR (1)	GR69195B (de)
IE (1)	IE50023B1 (de)
IL (1)	IL60482A (de)
IN (1)	IN154316B (de)
IT (1)	IT1237319B (de)
LU (1)	LU82608A1 (de)
MA (1)	MA18906A1 (de)
MX (1)	MX5962E (de)
NL (1)	NL8004053A (de)
NO (1)	NO155883C (de)
NZ (1)	NZ194280A (de)
OA (1)	OA06696A (de)
PT (1)	PT71578A (de)
SE (1)	SE448092B (de)
ZA (1)	ZA803993B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10320274A1 (de) *	2003-05-07	2004-12-09	Sennheiser Electronic Gmbh & Co. Kg	System zur ortssensitiven Wiedergabe von Audiosignalen

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1400425A (en) *	1971-09-22	1975-07-16	Rolland Sa A	Substituted 3-hydroxymethyl-isoquinolines and derivatives
US3966724A (en) *	1974-12-20	1976-06-29	Armour Pharmaceutical Company	1-(α-Aminomethylbenzyl)isoquinoline compounds
IT1143667B (it) *	1977-05-30	1986-10-22	Scharber Per L Ind Farmaceutic	Derivato paraverolinico ad azione duratura e procedimento per ottenerlo
IN154317B (de) *	1979-07-19	1984-10-13	Andre Buzas

1980
- 1980-07-02 IN IN491/DEL/80A patent/IN154316B/en unknown
- 1980-07-02 ZA ZA00803993A patent/ZA803993B/xx unknown
- 1980-07-02 FI FI802118A patent/FI77027C/fi not_active IP Right Cessation
- 1980-07-03 IL IL60482A patent/IL60482A/xx unknown
- 1980-07-08 CH CH520780A patent/CH644848A5/fr not_active IP Right Cessation
- 1980-07-08 MX MX808914U patent/MX5962E/es unknown
- 1980-07-09 BE BE0/201345A patent/BE884242A/fr not_active IP Right Cessation
- 1980-07-09 NZ NZ194280A patent/NZ194280A/xx unknown
- 1980-07-10 LU LU82608A patent/LU82608A1/fr unknown
- 1980-07-15 GR GR62459A patent/GR69195B/el unknown
- 1980-07-15 NL NL8004053A patent/NL8004053A/nl not_active Application Discontinuation
- 1980-07-15 MA MA19105A patent/MA18906A1/fr unknown
- 1980-07-17 AR AR281799A patent/AR228953A1/es active
- 1980-07-17 CA CA000356370A patent/CA1152998A/en not_active Expired
- 1980-07-17 FR FR8015781A patent/FR2461497A1/fr active Granted
- 1980-07-17 FR FR8015780A patent/FR2461702A1/fr active Granted
- 1980-07-17 AT AT0371980A patent/AT375649B/de not_active IP Right Cessation
- 1980-07-18 DE DE3027338A patent/DE3027338C2/de not_active Expired
- 1980-07-18 SE SE8005260A patent/SE448092B/sv not_active IP Right Cessation
- 1980-07-18 DK DK310180A patent/DK152124C/da not_active IP Right Cessation
- 1980-07-18 AU AU60630/80A patent/AU538065B2/en not_active Ceased
- 1980-07-18 IE IE1498/80A patent/IE50023B1/en unknown
- 1980-07-18 IT IT8023536A patent/IT1237319B/it active
- 1980-07-18 ES ES493503A patent/ES8106500A1/es not_active Expired
- 1980-07-18 JP JP9765480A patent/JPS5618964A/ja active Pending
- 1980-07-18 NO NO802160A patent/NO155883C/no unknown
- 1980-07-18 PT PT71578A patent/PT71578A/pt unknown
- 1980-07-19 EG EG433/80A patent/EG14616A/xx active
- 1980-07-19 OA OA57177A patent/OA06696A/xx unknown

Also Published As

Publication number	Publication date
IL60482A (en)	1984-02-29
NO802160L (no)	1981-01-20
LU82608A1 (fr)	1980-10-24
SE448092B (sv)	1987-01-19
EG14616A (en)	1989-09-30
IT1237319B (it)	1993-05-31
AT375649B (de)	1984-08-27
ES493503A0 (es)	1981-07-01
MA18906A1 (fr)	1981-04-01
OA06696A (fr)	1982-05-31
IE801498L (en)	1981-01-19
MX5962E (es)	1984-09-06
DE3027338C2 (de)	1984-08-09
NZ194280A (en)	1982-03-23
NO155883B (no)	1987-03-09
IT8023536A0 (it)	1980-07-18
IL60482A0 (en)	1980-09-16
ATA371980A (de)	1984-01-15
DE3027338A1 (de)	1981-02-19
FI77027B (fi)	1988-09-30
ES8106500A1 (es)	1981-07-01
CA1152998A (en)	1983-08-30
FR2461702A1 (fr)	1981-02-06
NL8004053A (nl)	1981-01-21
DK152124B (da)	1988-02-01
DK152124C (da)	1988-06-20
FI77027C (fi)	1989-01-10
BE884242A (fr)	1980-11-03
AU538065B2 (en)	1984-07-26
FR2461497A1 (fr)	1981-02-06
GR69195B (de)	1982-05-06
NO155883C (no)	1987-06-17
AU6063080A (en)	1981-01-22
IE50023B1 (en)	1986-02-05
IN154316B (de)	1984-10-13
DK310180A (da)	1981-01-20
FR2461702B1 (de)	1983-08-19
ZA803993B (en)	1981-07-29
JPS5618964A (en)	1981-02-23
AR228953A1 (es)	1983-05-13
PT71578A (en)	1980-08-01
SE8005260L (sv)	1981-01-20
FI802118A7 (fi)	1981-01-20
FR2461497B1 (de)	1983-07-01

Legal Events

Date	Code	Title	Description
1992-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
FR2500450A1 (fr)	1982-08-27	Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique
EP1095020B1 (de)	2005-08-31	4-aminopyridinderivate, ihre verwendung als arzneimittel und diese enthaltende pharmazeutische zusammensetzungen
EP0042781B1 (de)	1985-03-06	1-(4- Chinolyl), 2- oder 3- (2- oder 3-piperidyl oder pyrrolidinyl)-Äthanon oder -Propanon, Verfahren zu seiner Herstellung und seine Anwendung als Arzneimittel
EP0012643B1 (de)	1982-02-17	1-Phenyl-3-(4-piperidyl)-propan-1-on-Derivate, Verfahren zu ihrer Herstellung und die enthaltende pharmazeutische Zusammensetzungen
EP0461986B1 (de)	1996-01-10	Derivate von Hexahydroazepine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
EP0360685B1 (de)	1994-02-02	1-[(Diarylmethoxy)alkyl]-pyrrolidine und -piperidine, Verfahren zu ihrer Herstellung und Arzneimittel, die sie enthalten
EP0042322B1 (de)	1984-04-18	Indenderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0053964B1 (de)	1986-05-07	1(4-Chinolyl)äthanol- bzw. -propanolderivate, diese enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
EP0074873B1 (de)	1984-11-21	Derivate von 3-Phenoxy-2-propanolen, ihre Herstellung und ihre therapeutische Verwendung
EP0327455A1 (de)	1989-08-09	Phenol-Alkyl- oder -Benzylether, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
EP0173585B1 (de)	1988-08-24	Arzneimittel auf Basis von Piperidinderivaten, Piperidinderivate und Verfahren zu ihrer Herstellung
EP0143711B1 (de)	1987-08-12	Derivate von N-(Methoxyphenacyl)aminen, ihre therapeutische Verwendung und Verfahren zu ihrer Herstellung
CH644848A5 (en)	1984-08-31	Isoquinoline derivatives and their preparation
EP0037344A1 (de)	1981-10-07	Amino-alkoxy-pyrazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
EP0061406B1 (de)	1984-06-13	Benzamido-alkyl-hydroxamsäurederivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel
EP0027759B1 (de)	1983-10-12	Spiro-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
EP0065908B1 (de)	1984-12-05	((Alkyl- und Alkenyl-3-piperidyl-4)-2-äthyl)-3-indole und ihre Verwendung als Arzneimittel
EP0100257B1 (de)	1988-02-24	Aminoalkylnaphthalen-Derivate, ihre Salze und Verfahren zu ihrer Herstellung und die Verwendung dieser Derivate und Salze in der Therapeutik
EP0155888A1 (de)	1985-09-25	1-(4-Quinolyl)-2-(4-piperidyl)-ethanamin und 1-(4-Quinolyl)-2-(4-piperidyl)-propanamin Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
CH687705A5 (fr)	1997-01-31	Dérivés de la N-(phényléthyl-beta-ol) amine, un procédé pour leur préparation et des compositions pharmaceutiques les contenant.
EP0226475A1 (de)	1987-06-24	Diphenoxyethylaminderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
EP0017523A1 (de)	1980-10-15	Derivate des Dithiepinno (1,4)(2,3-c) pyrrols, ihre Herstellung und sie enthaltende Medikamente
FR2692894A1 (fr)	1993-12-31	Aryl-1-(o-alcoxy-phényl-4-pipérazinyl-1)-2, 3- ou 4-alcanols, leur procédé de préparation et leur utilisation pour la préparation de médicaments.
CA1217724A (fr)	1987-02-10	Compositions pharmaceutiques utiles comme antiarythmiques
CA1116089A (fr)	1982-01-12	Compositions pharmaceutiques comprenant des medicaments a base de derives de la quinoleine