CH540911A - Verfahren zur Herstellung von Isochinolinderivaten - Google Patents

Verfahren zur Herstellung von Isochinolinderivaten

Info

Publication number: CH540911A
Authority: CH; Switzerland
Prior art keywords: sep; tetrahydro; dimethyl; ethyl; formula
Prior art date: 1969-04-17

Application number

CH513870A

Other languages

German (de)

English (en)

Inventor

Eberhard Dr Kutter

Gerhart Dr Griss

Wolfgang Dr Grell

Manfred Dr Kleemann

Original Assignee

Thomae Gmbh Dr K

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.)

1969-04-17

Filing date

1970-04-07

Publication date

1973-08-31

1969-04-17 Priority claimed from DE19691919570 external-priority patent/DE1919570B1/de

1970-01-05 Priority claimed from DE19702000339 external-priority patent/DE2000339C3/de

1970-04-07 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1970-04-07 Priority to CH1823772A priority Critical patent/CH534161A/de

1970-04-07 Priority to CH1823572A priority patent/CH534159A/de

1970-04-07 Priority to CH1823872A priority patent/CH534162A/de

1970-04-07 Priority to CH1824072A priority patent/CH534163A/de

1970-04-07 Priority to CH1823672A priority patent/CH534160A/de

1973-08-31 Publication of CH540911A publication Critical patent/CH540911A/de

Links

125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title claims description 3
-1 sulphonyl halide Chemical class 0.000 claims abstract description 25
229940124530 sulfonamide Drugs 0.000 claims abstract description 9
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 9
150000003456 sulfonamides Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
238000001816 cooling Methods 0.000 claims description 5
239000012948 isocyanate Substances 0.000 claims description 5
150000002513 isocyanates Chemical class 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
239000004202 carbamide Substances 0.000 abstract description 28
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 3
150000001412 amines Chemical class 0.000 abstract description 3
150000001447 alkali salts Chemical class 0.000 abstract description 2
230000002152 alkylating effect Effects 0.000 abstract description 2
239000002585 base Substances 0.000 abstract description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 4
125000003545 alkoxy group Chemical group 0.000 abstract 2
ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 abstract 2
125000000217 alkyl group Chemical group 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
WCRKBMABEPCYII-UHFFFAOYSA-N isoquinolin-7-ol Chemical compound C1=CN=CC2=CC(O)=CC=C21 WCRKBMABEPCYII-UHFFFAOYSA-N 0.000 abstract 1
ANGQYYAUQIZRIS-UHFFFAOYSA-N isoquinoline thiourea Chemical compound NC(=S)N.C1=NC=CC2=CC=CC=C12 ANGQYYAUQIZRIS-UHFFFAOYSA-N 0.000 abstract 1
230000001035 methylating effect Effects 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 abstract 1
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
159000000000 sodium salts Chemical class 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000126 substance Substances 0.000 description 9
VBHCPGFCIQDXGZ-UHFFFAOYSA-N 1-isocyanatoadamantane Chemical compound C1C(C2)CC3CC2CC1(N=C=O)C3 VBHCPGFCIQDXGZ-UHFFFAOYSA-N 0.000 description 6
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
XRDYSLJVSXDXOD-UHFFFAOYSA-N 4-(ethylamino)benzenesulfonamide Chemical compound CCNC1=CC=C(S(N)(=O)=O)C=C1 XRDYSLJVSXDXOD-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
ZHQLTKAVLJKSKR-UHFFFAOYSA-N homophthalic acid Chemical compound OC(=O)CC1=CC=CC=C1C(O)=O ZHQLTKAVLJKSKR-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
230000036772 blood pressure Effects 0.000 description 4
230000037396 body weight Effects 0.000 description 4
238000009835 boiling Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 3
239000001828 Gelatine Substances 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
239000001923 methylcellulose Substances 0.000 description 3
235000010981 methylcellulose Nutrition 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
JZIQDXMLHJLYSF-UHFFFAOYSA-N CC(C(C=C1)=CC=C1S(N)(=O)=O)N(C(C(C)(C)C1=CC=CC=C11)=O)C1=O Chemical compound CC(C(C=C1)=CC=C1S(N)(=O)=O)N(C(C(C)(C)C1=CC=CC=C11)=O)C1=O JZIQDXMLHJLYSF-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000008103 glucose Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
239000008096 xylene Substances 0.000 description 2
102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
TVGNKWOVMAGGEE-UHFFFAOYSA-N 7-hydroxy-2,4,4-trimethylisoquinoline-1,3-dione Chemical compound CN1C(C2=CC(=CC=C2C(C1=O)(C)C)O)=O TVGNKWOVMAGGEE-UHFFFAOYSA-N 0.000 description 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
102000005548 Hexokinase Human genes 0.000 description 1
108700040460 Hexokinases Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
229950009941 chloralose Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
210000003800 pharynx Anatomy 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000003462 vein Anatomy 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
- C07D217/22—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
- C07D217/24—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
- H01R4/00—Electrically-conductive connections between two or more conductive members in direct contact, i.e. touching one another; Means for effecting or maintaining such contact; Electrically-conductive connections having two or more spaced connecting locations for conductors and using contact members penetrating insulation
- H01R4/28—Clamped connections, spring connections
- H01R4/50—Clamped connections, spring connections utilising a cam, wedge, cone or ball also combined with a screw

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (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)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH513870A 1969-04-17 1970-04-07 Verfahren zur Herstellung von Isochinolinderivaten CH540911A (de)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CH1823772A CH534161A (de)	1970-03-10	1970-04-07	Verfahren zur Herstellung von Isochinolinderivaten
CH1823572A CH534159A (de)	1970-03-10	1970-04-07	Verfahren zur Herstellung von Isochinolinderivaten
CH1823872A CH534162A (de)	1970-03-10	1970-04-07	Verfahren zur Herstellung von Isochinolinderivaten
CH1824072A CH534163A (de)	1970-03-10	1970-04-07	Verfahren zur Herstellung von Isochinolinderivaten
CH1823672A CH534160A (de)	1970-03-10	1970-04-07	Verfahren zur Herstellung von Isochinolinderivaten

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19691919570 DE1919570B1 (de)	1969-04-17	1969-04-17	Isochinolinderivate
DE19702000339 DE2000339C3 (de)	1970-01-05	1970-01-05	Isochinolinderivate
DE19702011126 DE2011126A1 (de)	1969-04-17	1970-03-10	Isochinolinderivate und Verfahren zu ihrer Herstellung

Publications (1)

Publication Number	Publication Date
CH540911A true CH540911A (de)	1973-08-31

Family

ID=27181893

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH513870A CH540911A (de)	1969-04-17	1970-04-07	Verfahren zur Herstellung von Isochinolinderivaten

Country Status (9)

Country	Link
AT (1)	AT296327B (da)
BG (1)	BG17779A3 (da)
CH (1)	CH540911A (da)
DK (1)	DK134283C (da)
FI (1)	FI49829C (da)
NO (1)	NO132198C (da)
PL (1)	PL80584B1 (da)
SE (1)	SE353091B (da)
SU (2)	SU441707A3 (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2010112946A1 (en)	2009-03-31	2010-10-07	Rudjer Boskovic Institute	Adamantane bisurea derivatives, method of preparation and application in anion sensing

1970
- 1970-04-03 FI FI93670A patent/FI49829C/fi active
- 1970-04-07 CH CH513870A patent/CH540911A/de not_active IP Right Cessation
- 1970-04-07 BG BG016217A patent/BG17779A3/xx unknown
- 1970-04-10 SU SU1637448A patent/SU441707A3/ru active
- 1970-04-16 NO NO144670A patent/NO132198C/no unknown
- 1970-04-16 AT AT346970A patent/AT296327B/de not_active IP Right Cessation
- 1970-04-16 DK DK191570A patent/DK134283C/da active
- 1970-04-16 PL PL14005470A patent/PL80584B1/pl unknown
- 1970-04-17 SE SE535370A patent/SE353091B/xx unknown
1971
- 1971-03-29 SU SU1642934A patent/SU476749A3/ru active

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2010112946A1 (en)	2009-03-31	2010-10-07	Rudjer Boskovic Institute	Adamantane bisurea derivatives, method of preparation and application in anion sensing

Also Published As

Publication number	Publication date
FI49829B (da)	1975-06-30
AT296327B (de)	1972-02-10
NO132198C (da)	1975-10-01
SU476749A3 (ru)	1975-07-05
DK134283C (da)	1977-04-18
DK134283B (da)	1976-10-11
NO132198B (da)	1975-06-23
BG17779A3 (bg)	1973-12-25
SE353091B (da)	1973-01-22
PL80584B1 (en)	1975-08-30
FI49829C (fi)	1975-10-10
SU441707A3 (ru)	1974-08-30

Legal Events

Date	Code	Title	Description
1986-12-31	PL	Patent ceased

Publication	Publication Date	Title
DE2934747A1 (de)	1980-03-13	Tetrazolylalkoxycarbostyrilderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten
EP0014951A2 (de)	1980-09-03	Heterocyclische Oxypropanolamin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2238504B2 (de)	1979-07-19	l-Phenoxy-3-alkylaminopropan-2-ol -Derivate
DE2428486A1 (de)	1975-01-09	Azapurinone
CH642066A5 (de)	1984-03-30	3-indolyl-tert.-butylaminopropanole, verfahren zu deren herstellung und sie enthaltende pharmazeutische mittel.
DE3813531A1 (de)	1988-11-10	Neue 2-aminoalkyl-4-benzyl-1-(2h)-phthalazinon-derivate
EP0018360B1 (de)	1981-09-30	N-(5-Methoxybentofuran-2-ylcarbonyl)-N'-benzylpiperazin und Verfahren zu dessen Herstellung
DE1940566B2 (de)	1978-03-30	1- (2-Nitrilophenoxy)-2-hydroxy-3äthylaminopropan, Verfahren zu dessen Herstellung und diese enthaltende Arzneimittel
EP0073507B1 (de)	1985-10-16	Sulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung
CH540911A (de)	1973-08-31	Verfahren zur Herstellung von Isochinolinderivaten
DE2427207A1 (de)	1975-01-09	Verfahren zur herstellung von kondensierten pyrrolmercapto-verbindungen
DE2000339C3 (de)	1979-04-19	Isochinolinderivate
EP0072954A2 (de)	1983-03-02	Isoindolin-2-yl-amino-imidazoline und Isoindolin-2-yl-guanidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DD146823A5 (de)	1981-03-04	Verfahren zur herstellung von aminopropanolderivaten des 6-hydroxy-2,3,4,5-tetrahydro-1 h-1-benzazepin-2-ons
DE2831671A1 (de)	1980-02-07	Neue substituierte 2-phenylamino-imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben
DE2062055C3 (de)	1979-01-18	Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE1909272A1 (de)	1970-09-10	N-[4-(ss<2-Methoxy-5-chlor-benzamido>-aethyl)-benzolsulfonyl]-N'-cyclopentylharnstoff und Verfahren zu seiner Herstellung
DE2923817B1 (de)	1980-08-14	(3-Alkylamino-2-hydroxypropoxy)-furan-2-carbonsaeureanilide und deren physiologisch vertraegliche Saeureadditionssalze und Verfahren zu deren Herstellung sowie Arzneimittel mit einem Gehalt dieser Verbindungen
EP0592453B1 (de)	1998-12-16	Aminoalkylsubstituierte 2-amino-1,3,4-thiadiazole, ihre herstellung und verwendung
DE2832310A1 (de)	1980-02-07	Neue substituierte 2-phenylamino-imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben
DD210266A5 (de)	1984-06-06	Verfahren zur herstellung von 3-(ureidocyclohexylamino)-propan-1,2-diolderivaten
CH534159A (de)	1973-02-28	Verfahren zur Herstellung von Isochinolinderivaten
EP0289881A2 (de)	1988-11-09	Neue 2-Aminoalkyl-4-bennzyl-1-(2H)-phthalazinon-Derivate
US3288793A (en)	1966-11-29	2-tetrahydrofurfuryl-, 2-aliphatic-, and 2-aliphatic ether-sulfonamido-5-alkoxy-pyrimidines
DE2253251A1 (de)	1974-05-09	Neue phthalimido-sulfonylharnstoffe

CH540911A - Verfahren zur Herstellung von Isochinolinderivaten - Google Patents

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