FI74272C - Foerfarande foer framstaellning av farmakologiskt aktiv 1-(acylaminoaryloxi-2-hydroxi-3-alkinylaminopropan. - Google Patents
Foerfarande foer framstaellning av farmakologiskt aktiv 1-(acylaminoaryloxi-2-hydroxi-3-alkinylaminopropan. Download PDFInfo
- Publication number
- FI74272C FI74272C FI810714A FI810714A FI74272C FI 74272 C FI74272 C FI 74272C FI 810714 A FI810714 A FI 810714A FI 810714 A FI810714 A FI 810714A FI 74272 C FI74272 C FI 74272C
- Authority
- FI
- Finland
- Prior art keywords
- carbon atoms
- formula
- alkyl
- treatment
- farmakologiskt
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 208000001871 Tachycardia Diseases 0.000 abstract description 7
- 230000006794 tachycardia Effects 0.000 abstract description 7
- 238000011282 treatment Methods 0.000 abstract description 6
- 206010003119 arrhythmia Diseases 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 229960001317 isoprenaline Drugs 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 241000700198 Cavia Species 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- -1 β-methylpentanoylamino-phenoxy Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 230000036760 body temperature Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- MFEDKMBNKNOUPA-UHFFFAOYSA-N (2-bromo-4,7-dimethyl-3-oxo-7-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound C1CC2(C)C(=O)C(Br)C1C2(CS(O)(=O)=O)C MFEDKMBNKNOUPA-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
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- NJAFAMSQSPHJDB-UHFFFAOYSA-N C(#N)C(C(=O)NC1=C(OCC2CO2)C=CC=C1)CCCC Chemical compound C(#N)C(C(=O)NC1=C(OCC2CO2)C=CC=C1)CCCC NJAFAMSQSPHJDB-UHFFFAOYSA-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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- 241000906446 Theraps Species 0.000 description 1
- GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 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
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- RKXVNVQWGXAIPB-UHFFFAOYSA-N n-[3-cyano-4-(oxiran-2-ylmethoxy)phenyl]hexanamide Chemical compound N#CC1=CC(NC(=O)CCCCC)=CC=C1OCC1OC1 RKXVNVQWGXAIPB-UHFFFAOYSA-N 0.000 description 1
- WDICZTCLTZCNLK-UHFFFAOYSA-N n-[3-cyano-4-(oxiran-2-ylmethoxy)phenyl]octanamide Chemical compound N#CC1=CC(NC(=O)CCCCCCC)=CC=C1OCC1OC1 WDICZTCLTZCNLK-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Pyrane Compounds (AREA)
- Manufacture Of Tobacco Products (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803009047 DE3009047A1 (de) | 1980-03-08 | 1980-03-08 | Neue l-(acylamino-aryloxy-)2-hydroxy-3-alkinylaminopropane und verfahren zu ihrer herstellung |
| DE3009047 | 1980-03-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI810714L FI810714L (fi) | 1981-09-09 |
| FI74272B FI74272B (fi) | 1987-09-30 |
| FI74272C true FI74272C (fi) | 1988-01-11 |
Family
ID=6096693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI810714A FI74272C (fi) | 1980-03-08 | 1981-03-06 | Foerfarande foer framstaellning av farmakologiskt aktiv 1-(acylaminoaryloxi-2-hydroxi-3-alkinylaminopropan. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4609672A (index.php) |
| EP (1) | EP0035733B1 (index.php) |
| JP (1) | JPS56139448A (index.php) |
| AT (1) | ATE4639T1 (index.php) |
| AU (1) | AU541492B2 (index.php) |
| CA (1) | CA1150735A (index.php) |
| DE (2) | DE3009047A1 (index.php) |
| DK (1) | DK102581A (index.php) |
| ES (3) | ES500154A0 (index.php) |
| FI (1) | FI74272C (index.php) |
| GB (1) | GB2071096B (index.php) |
| GR (1) | GR74907B (index.php) |
| IE (1) | IE52015B1 (index.php) |
| IL (1) | IL62308A (index.php) |
| NO (1) | NO150961C (index.php) |
| NZ (1) | NZ196445A (index.php) |
| PT (1) | PT72620B (index.php) |
| ZA (1) | ZA811499B (index.php) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3133719A1 (de) * | 1981-08-26 | 1983-03-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue 1-aryloxy-3-alkinylamino-2-propanole und verfahren zu ihrer herstellung |
| PT1117409E (pt) | 1998-09-10 | 2005-04-29 | Aventis Pharma Gmbh | Benzenossulfonil (tio) ureias em associacao com betabloqueantes para o tratamento de disfuncoes do sistema nervoso autonomo |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH546224A (en) * | 1969-08-08 | 1974-02-28 | Boehringer Sohn Ingelheim | 1-(2-nitrilophenoxy)-2-hydroxy-3-ethylamino - propane |
| CH546227A (en) * | 1969-08-08 | 1974-02-28 | Boehringer Sohn Ingelheim | 1-(2-nitrilophenoxy)-2-hydroxy-3-ethylamino - propane |
| DE2403809C2 (de) * | 1974-01-26 | 1986-02-27 | C.H. Boehringer Sohn, 6507 Ingelheim | 1-Aryloxy-2-hydroxy-3-alkinylaminopropane und Verfahren zu ihrer Herstellung und pharmazeutische Präparate |
| DE2309887C2 (de) * | 1973-02-28 | 1983-11-10 | C.H. Boehringer Sohn, 6507 Ingelheim | 1-Aryloxy-2-hydroxy-3-alkinylaminopropan-Derivate und deren physiologisch verträgliche Säureadditionssalze, pharmazeutische Präparate und Herstellungsverfahren für die Verbindungen |
| AT330150B (de) * | 1973-02-28 | 1976-06-10 | Boehringer Sohn Ingelheim | Verfahren zur herstellung von neuen 1-phenoxy-2-hydroxy -3- propargylaminopropanen und von deren saureadditionssalzen |
| DE3009036A1 (de) * | 1980-03-08 | 1981-09-24 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue l-(acylamino-aryloxy-)2-hydroxy-3-alkinylaminopropane und verfahren zu ihrer herstellung |
-
1980
- 1980-03-08 DE DE19803009047 patent/DE3009047A1/de not_active Withdrawn
-
1981
- 1981-03-03 DE DE8181101498T patent/DE3160861D1/de not_active Expired
- 1981-03-03 AT AT81101498T patent/ATE4639T1/de not_active IP Right Cessation
- 1981-03-03 EP EP81101498A patent/EP0035733B1/de not_active Expired
- 1981-03-05 NO NO810764A patent/NO150961C/no unknown
- 1981-03-05 PT PT72620A patent/PT72620B/pt unknown
- 1981-03-06 DK DK102581A patent/DK102581A/da not_active Application Discontinuation
- 1981-03-06 ES ES500154A patent/ES500154A0/es active Granted
- 1981-03-06 GB GB8107115A patent/GB2071096B/en not_active Expired
- 1981-03-06 CA CA000372475A patent/CA1150735A/en not_active Expired
- 1981-03-06 IE IE486/81A patent/IE52015B1/en unknown
- 1981-03-06 NZ NZ196445A patent/NZ196445A/en unknown
- 1981-03-06 JP JP3236681A patent/JPS56139448A/ja active Pending
- 1981-03-06 FI FI810714A patent/FI74272C/fi not_active IP Right Cessation
- 1981-03-06 IL IL62308A patent/IL62308A/xx unknown
- 1981-03-06 ZA ZA00811499A patent/ZA811499B/xx unknown
- 1981-03-06 AU AU68157/81A patent/AU541492B2/en not_active Ceased
- 1981-03-06 GR GR64336A patent/GR74907B/el unknown
-
1982
- 1982-02-11 ES ES509513A patent/ES509513A0/es active Granted
- 1982-02-11 ES ES509514A patent/ES8302638A1/es not_active Expired
-
1984
- 1984-06-25 US US06/623,960 patent/US4609672A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO150961B (no) | 1984-10-08 |
| PT72620A (de) | 1981-04-01 |
| DE3160861D1 (en) | 1983-10-20 |
| NO810764L (no) | 1981-09-09 |
| NO150961C (no) | 1985-01-16 |
| IE810486L (en) | 1981-09-08 |
| CA1150735A (en) | 1983-07-26 |
| US4609672A (en) | 1986-09-02 |
| ZA811499B (en) | 1982-11-24 |
| ES8205396A1 (es) | 1982-06-01 |
| ATE4639T1 (de) | 1983-09-15 |
| IE52015B1 (en) | 1987-05-27 |
| AU6815781A (en) | 1981-09-17 |
| DK102581A (da) | 1981-09-09 |
| PT72620B (de) | 1982-11-15 |
| NZ196445A (en) | 1984-05-31 |
| ES8303300A1 (es) | 1983-02-01 |
| EP0035733A1 (de) | 1981-09-16 |
| ES509513A0 (es) | 1983-02-01 |
| DE3009047A1 (de) | 1981-09-24 |
| ES509514A0 (es) | 1983-01-16 |
| ES8302638A1 (es) | 1983-01-16 |
| EP0035733B1 (de) | 1983-09-14 |
| IL62308A0 (en) | 1981-05-20 |
| IL62308A (en) | 1984-12-31 |
| JPS56139448A (en) | 1981-10-30 |
| FI810714L (fi) | 1981-09-09 |
| ES500154A0 (es) | 1982-06-01 |
| FI74272B (fi) | 1987-09-30 |
| GB2071096B (en) | 1983-09-14 |
| GR74907B (index.php) | 1984-07-12 |
| AU541492B2 (en) | 1985-01-10 |
| GB2071096A (en) | 1981-09-16 |
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