SE443786B - Nytt forfarande for framstellning av anilinderivat av kinuklidinkarbonsyra - Google Patents
Nytt forfarande for framstellning av anilinderivat av kinuklidinkarbonsyraInfo
- Publication number
- SE443786B SE443786B SE7800204A SE7800204A SE443786B SE 443786 B SE443786 B SE 443786B SE 7800204 A SE7800204 A SE 7800204A SE 7800204 A SE7800204 A SE 7800204A SE 443786 B SE443786 B SE 443786B
- Authority
- SE
- Sweden
- Prior art keywords
- compound
- dose
- carboxylic acid
- acid
- quinuclidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims description 9
- 239000002253 acid Substances 0.000 title claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 61
- 206010003119 arrhythmia Diseases 0.000 claims description 31
- 230000006793 arrhythmia Effects 0.000 claims description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 14
- LIUAALCHBQSCCX-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane-2-carboxylate Chemical compound C1CN2C(C(=O)O)CC1CC2 LIUAALCHBQSCCX-UHFFFAOYSA-N 0.000 claims description 14
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 claims description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 4
- 230000006872 improvement Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000008859 change Effects 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000033001 locomotion Effects 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 239000000729 antidote Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 231100000873 signs of neurotoxicity Toxicity 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 241000282472 Canis lupus familiaris Species 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010253 intravenous injection Methods 0.000 description 9
- 229960004194 lidocaine Drugs 0.000 description 9
- 230000003288 anthiarrhythmic effect Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 230000033764 rhythmic process Effects 0.000 description 8
- PUIHXLMMFNAYNW-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octane-3-carboxylic acid Chemical class C1CC2C(C(=O)O)CN1CC2 PUIHXLMMFNAYNW-UHFFFAOYSA-N 0.000 description 7
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 7
- LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 7
- 244000166550 Strophanthus gratus Species 0.000 description 7
- 230000001186 cumulative effect Effects 0.000 description 7
- 229940105631 nembutal Drugs 0.000 description 7
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 7
- 229960003343 ouabain Drugs 0.000 description 7
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 241000282326 Felis catus Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 206010047302 ventricular tachycardia Diseases 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 206010010904 Convulsion Diseases 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 231100000189 neurotoxic Toxicity 0.000 description 4
- 230000002887 neurotoxic effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000011287 therapeutic dose Methods 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- JOIJZJVAIURHGA-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octane-2-carboxylic acid;hydrochloride Chemical compound Cl.C1CN2C(C(=O)O)CC1CC2 JOIJZJVAIURHGA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 3
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 238000000718 qrs complex Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- LXHNHXQYRPDFPN-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octane-3-carboxylic acid;hydrochloride Chemical compound Cl.C1CC2C(C(=O)O)CN1CC2 LXHNHXQYRPDFPN-UHFFFAOYSA-N 0.000 description 2
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 230000036765 blood level Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 206010003591 Ataxia Diseases 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 206010038687 Respiratory distress Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 208000009729 Ventricular Premature Complexes Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 206010000891 acute myocardial infarction Diseases 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 208000021264 digitalis poisoning Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- HCIRLKXASKPUHN-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1C(CC2)CCN2C1 HCIRLKXASKPUHN-UHFFFAOYSA-N 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 201000002932 second-degree atrioventricular block Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL51296A IL51296A (en) | 1977-01-19 | 1977-01-19 | Antiarrhythmic composition comprising a quinuclidine-3-carboxylic acid anilide and novel method for the preparation of such anilides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7800204L SE7800204L (sv) | 1978-07-20 |
| SE443786B true SE443786B (sv) | 1986-03-10 |
Family
ID=11049358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7800204A SE443786B (sv) | 1977-01-19 | 1978-01-09 | Nytt forfarande for framstellning av anilinderivat av kinuklidinkarbonsyra |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS53109952A (de) |
| AT (1) | AT355586B (de) |
| AU (1) | AU519089B2 (de) |
| CA (1) | CA1107734A (de) |
| DE (1) | DE2802208A1 (de) |
| DK (1) | DK147180C (de) |
| ES (1) | ES465827A1 (de) |
| FI (1) | FI773923A7 (de) |
| FR (1) | FR2384499A1 (de) |
| GB (2) | GB1578421A (de) |
| IL (1) | IL51296A (de) |
| NO (1) | NO148335C (de) |
| NZ (1) | NZ185904A (de) |
| PT (1) | PT67401B (de) |
| SE (1) | SE443786B (de) |
| ZA (1) | ZA777476B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10211416A1 (de) | 2002-03-15 | 2003-09-25 | Bayer Ag | Essig- und Propionsäureamide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE331841B (de) * | 1967-05-23 | 1971-01-18 | Astra Ab |
-
1977
- 1977-01-19 IL IL51296A patent/IL51296A/xx unknown
- 1977-12-08 NZ NZ185904A patent/NZ185904A/en unknown
- 1977-12-14 PT PT67401A patent/PT67401B/pt unknown
- 1977-12-15 ZA ZA00777476A patent/ZA777476B/xx unknown
- 1977-12-23 FI FI773923A patent/FI773923A7/fi not_active Application Discontinuation
-
1978
- 1978-01-07 ES ES465827A patent/ES465827A1/es not_active Expired
- 1978-01-09 SE SE7800204A patent/SE443786B/sv unknown
- 1978-01-17 AU AU32489/78A patent/AU519089B2/en not_active Expired
- 1978-01-18 DK DK26478A patent/DK147180C/da active
- 1978-01-18 NO NO780177A patent/NO148335C/no unknown
- 1978-01-18 AT AT35378A patent/AT355586B/de not_active IP Right Cessation
- 1978-01-18 FR FR7801354A patent/FR2384499A1/fr active Granted
- 1978-01-18 CA CA295,163A patent/CA1107734A/en not_active Expired
- 1978-01-19 GB GB2197/78A patent/GB1578421A/en not_active Expired
- 1978-01-19 JP JP476478A patent/JPS53109952A/ja active Granted
- 1978-01-19 DE DE19782802208 patent/DE2802208A1/de not_active Withdrawn
- 1978-01-19 GB GB21014/79A patent/GB1578422A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI773923A7 (fi) | 1978-07-20 |
| ZA777476B (en) | 1978-10-25 |
| GB1578422A (en) | 1980-11-05 |
| NO148335B (no) | 1983-06-13 |
| CA1107734A (en) | 1981-08-25 |
| NO148335C (no) | 1983-09-21 |
| ES465827A1 (es) | 1979-01-01 |
| PT67401B (en) | 1979-05-21 |
| IL51296A (en) | 1983-10-31 |
| SE7800204L (sv) | 1978-07-20 |
| PT67401A (en) | 1978-01-01 |
| DK26478A (da) | 1978-07-20 |
| DE2802208A1 (de) | 1978-07-20 |
| FR2384499B1 (de) | 1981-10-30 |
| NO780177L (no) | 1978-07-20 |
| IL51296A0 (en) | 1977-03-31 |
| AU519089B2 (en) | 1981-11-05 |
| AU3248978A (en) | 1979-07-26 |
| DK147180B (da) | 1984-05-07 |
| DK147180C (da) | 1984-11-12 |
| AT355586B (de) | 1980-03-10 |
| JPS53109952A (en) | 1978-09-26 |
| NZ185904A (en) | 1984-05-31 |
| GB1578421A (en) | 1980-11-05 |
| FR2384499A1 (fr) | 1978-10-20 |
| ATA35378A (de) | 1979-08-15 |
| JPS638111B2 (de) | 1988-02-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1957706C3 (de) | Kernsubstituierte 3-Phenoxy-l-phenoxyalkylamino-propan-2-ole und Arzneimittel auf deren Basis | |
| US4302465A (en) | Therapeutically active, substituted piperidines and pyrrolidines therapeutic compositions thereof and methods of use thereof | |
| DE69104615T2 (de) | Diphenylpiperazinderivat. | |
| DE2707048C2 (de) | 2-Alkyl-3-Benzoyl-Indolizinderivate, Verfahren zu deren Herstellung, sowie diese enthaltende Zusammensetzungen | |
| EP0632806B1 (de) | Aminocyclohexylamide für antiarrhythmische und anästhetische verwendungen | |
| AT368130B (de) | Verfahren zur herstellung von neuen 9-aminoalkyl- fluorenen und von deren salzen | |
| EP0338746B1 (de) | 2-Alkyl-3-benzoylbenzofurane und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE2362278C2 (de) | 5-(2-Hydroxy-3-alkylamino)-propoxycarbostyril-Verbindungen, deren Salze mit Säuren, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| US4374149A (en) | α-{[(Arylalkyl)amino]alkyl}-4-hydroxy-3-(lower-alkylsulfinyl)benzenemethanols | |
| DE3873167T2 (de) | Thiazolidin-4-on-derivate und deren saeure-additionssalze. | |
| KR100352899B1 (ko) | 새로운3-페닐설포닐-3,7-디아자바이사이클로[3,3,1]노난-화합물을함유하는약제 | |
| DE69010757T2 (de) | Phenylalkanolsäureester. | |
| SE443786B (sv) | Nytt forfarande for framstellning av anilinderivat av kinuklidinkarbonsyra | |
| US3910871A (en) | Novel glycylglycine amides | |
| EP0105458B1 (de) | Alpha-Aryl-alpha-pyridylalkanoicsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzung | |
| US4146628A (en) | Antiarrhythmic quinuclidine carboxylic acid xylidide and method of producing the same and similar compounds | |
| PT96315B (pt) | Processo para a preparacao de derivados de diamina e de composicoes farmaceuticas que os contem | |
| US4415495A (en) | 5,6;8,9-Tetrahydro-7H-dibenz(d,f)azonines | |
| US4452816A (en) | Method of lowering blood pressure by α-{[arylalkylamino]alkyl}-4-hydroxy-3-(loweralkylsulfinyl)benzenemethanols | |
| NO141555B (no) | Analogifremgangsmaate for fremstilling av nye terapeutisk virksomme dibenzocykloheptenkarboksamider | |
| DE68924416T2 (de) | Carboximidamid-Derivate. | |
| JP4223237B2 (ja) | ３−フェニル−３，７−ジアザビシクロ［３，３，１］ノナン−化合物、これを含有する医薬品、その使用及びその製法 | |
| DE69106276T2 (de) | Säureadditionssalze einer optisch aktiven Alaninanilidverbindung und diese enthaltende, pharmazeutische Zusammensetzungen. | |
| Mellin et al. | Dimethylsulfonium analogs of the muscarinic agent McN-A-343:[4-[[N-(3-or 4-halophenyl) carbamoyl] oxy]-2-butynyl] dimethylsulfonium perchlorates | |
| SE465675B (sv) | Basiska oximetrar, foerfarande foer framstaellning daerav och farmaceutiska kompositioner innehaallande desamma |