DK142843B - Analogifremgangsmåde til fremstilling af 2-amino-2',6'-propiono-xylidid eller syreadditionssalte heraf. - Google Patents
Analogifremgangsmåde til fremstilling af 2-amino-2',6'-propiono-xylidid eller syreadditionssalte heraf. Download PDFInfo
- Publication number
- DK142843B DK142843B DK365272AA DK365272A DK142843B DK 142843 B DK142843 B DK 142843B DK 365272A A DK365272A A DK 365272AA DK 365272 A DK365272 A DK 365272A DK 142843 B DK142843 B DK 142843B
- Authority
- DK
- Denmark
- Prior art keywords
- amino
- compound
- propionoxylidide
- drug
- acid addition
- Prior art date
Links
- BUJAGSGYPOAWEI-UHFFFAOYSA-N tocainide Chemical compound CC(N)C(=O)NC1=C(C)C=CC=C1C BUJAGSGYPOAWEI-UHFFFAOYSA-N 0.000 title description 14
- 150000003839 salts Chemical class 0.000 title description 10
- 239000002253 acid Substances 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 27
- 238000000034 method Methods 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 229940079593 drug Drugs 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 241000282472 Canis lupus familiaris Species 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 10
- 230000003288 anthiarrhythmic effect Effects 0.000 description 10
- 239000003416 antiarrhythmic agent Substances 0.000 description 9
- 229960004194 lidocaine Drugs 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 230000002861 ventricular Effects 0.000 description 7
- 206010003119 arrhythmia Diseases 0.000 description 6
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 239000003589 local anesthetic agent Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000003444 anaesthetic effect Effects 0.000 description 4
- 230000006793 arrhythmia Effects 0.000 description 4
- 210000005036 nerve Anatomy 0.000 description 4
- 210000001147 pulmonary artery Anatomy 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 3
- -1 hydrochloric Chemical class 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 3
- 229960000244 procainamide Drugs 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 229960001404 quinidine Drugs 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 208000001778 Coronary Occlusion Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 2
- 241000906446 Theraps Species 0.000 description 2
- 206010047289 Ventricular extrasystoles Diseases 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 230000036982 action potential Effects 0.000 description 2
- 231100000460 acute oral toxicity Toxicity 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 229960005015 local anesthetics Drugs 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960002036 phenytoin Drugs 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LCGFVWKNXLRFIF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine Chemical class C1=CC=C2CC(N)CCC2=C1 LCGFVWKNXLRFIF-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 206010011086 Coronary artery occlusion Diseases 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
- 208000034693 Laceration Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
- 241001585714 Nola Species 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- 208000009729 Ventricular Premature Complexes Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 210000001308 heart ventricle Anatomy 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000003116 impacting effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000000715 neuromuscular junction Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 201000004193 respiratory failure Diseases 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 229940072358 xylocaine Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16703171A | 1971-07-28 | 1971-07-28 | |
| US16703171 | 1971-07-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK142843B true DK142843B (da) | 1981-02-09 |
| DK142843C DK142843C (ru) | 1981-08-31 |
Family
ID=22605664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK365272AA DK142843B (da) | 1971-07-28 | 1972-07-24 | Analogifremgangsmåde til fremstilling af 2-amino-2',6'-propiono-xylidid eller syreadditionssalte heraf. |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS565220B1 (ru) |
| AR (1) | AR193748A1 (ru) |
| AT (1) | AT317185B (ru) |
| AU (1) | AU476000B2 (ru) |
| BE (1) | BE786875A (ru) |
| BR (1) | BR7205069D0 (ru) |
| CA (1) | CA982148A (ru) |
| CH (1) | CH574397A5 (ru) |
| CS (1) | CS171171B2 (ru) |
| DD (1) | DD101389A5 (ru) |
| DK (1) | DK142843B (ru) |
| ES (1) | ES404739A1 (ru) |
| FI (1) | FI55492C (ru) |
| FR (1) | FR2147277B1 (ru) |
| GB (1) | GB1374367A (ru) |
| HU (1) | HU163818B (ru) |
| IE (1) | IE36607B1 (ru) |
| NL (1) | NL176254C (ru) |
| NO (1) | NO137500C (ru) |
| PL (1) | PL84891B1 (ru) |
| SE (1) | SE399702B (ru) |
| SU (1) | SU441704A3 (ru) |
| ZA (1) | ZA724512B (ru) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57182525U (ru) * | 1981-05-15 | 1982-11-19 | ||
| JPH01128053U (ru) * | 1988-02-24 | 1989-08-31 | ||
| JP2514855B2 (ja) * | 1990-08-08 | 1996-07-10 | キッセイ薬品工業株式会社 | 光学活性なアラニンアニリド誘導体の酸付加塩 |
| GB2267709A (en) * | 1992-06-11 | 1993-12-15 | Merck & Co Inc | Novel process for the preparation of alpha-aminoacylanilides |
| CA3027255C (en) | 2009-07-10 | 2022-06-21 | The General Hospital Corporation | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
| DE102012210082A1 (de) * | 2012-06-15 | 2013-12-19 | Hilti Aktiengesellschaft | Werkzeugmaschine und Steuerungsverfahren |
| JP6833811B2 (ja) | 2015-08-03 | 2021-02-24 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 荷電イオンチャネル遮断薬及び使用方法 |
| US11377422B2 (en) | 2019-03-11 | 2022-07-05 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| AU2020237474A1 (en) | 2019-03-11 | 2021-09-30 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| CA3129089A1 (en) | 2019-03-11 | 2020-09-17 | Bridget Mccarthy Cole | Ester substituted ion channel blockers and methods for use |
| US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| KR20220123381A (ko) | 2019-11-06 | 2022-09-06 | 녹시온 테라퓨틱스 인코포레이티드 | 하전된 이온 채널 차단제 및 사용 방법 |
| EP4118070A4 (en) | 2020-03-11 | 2024-04-10 | Nocion Therapeutics, Inc. | CHARGED ION CHANNEL BLOCKERS AND METHODS OF USE |
-
0
- BE BE786875D patent/BE786875A/xx not_active IP Right Cessation
-
1972
- 1972-06-30 ZA ZA724512A patent/ZA724512B/xx unknown
- 1972-07-04 CS CS4729A patent/CS171171B2/cs unknown
- 1972-07-04 SE SE7208768A patent/SE399702B/xx unknown
- 1972-07-07 FI FI1945/72A patent/FI55492C/fi active
- 1972-07-11 ES ES404739A patent/ES404739A1/es not_active Expired
- 1972-07-17 CA CA147,247A patent/CA982148A/en not_active Expired
- 1972-07-19 CH CH1080572A patent/CH574397A5/xx not_active IP Right Cessation
- 1972-07-20 GB GB3548172A patent/GB1374367A/en not_active Expired
- 1972-07-20 SU SU1812965A patent/SU441704A3/ru active
- 1972-07-24 DK DK365272AA patent/DK142843B/da not_active IP Right Cessation
- 1972-07-24 AU AU44886/72A patent/AU476000B2/en not_active Expired
- 1972-07-25 AR AR243250A patent/AR193748A1/es active
- 1972-07-25 NO NO2662/72A patent/NO137500C/no unknown
- 1972-07-26 PL PL1972156947A patent/PL84891B1/pl unknown
- 1972-07-27 HU HUAA709A patent/HU163818B/hu unknown
- 1972-07-27 FR FR7227161A patent/FR2147277B1/fr not_active Expired
- 1972-07-27 DD DD164729A patent/DD101389A5/xx unknown
- 1972-07-27 IE IE1058/72A patent/IE36607B1/xx unknown
- 1972-07-28 BR BR5069/72A patent/BR7205069D0/pt unknown
- 1972-07-28 AT AT650472A patent/AT317185B/de active
- 1972-07-28 JP JP7518072A patent/JPS565220B1/ja active Pending
- 1972-07-28 NL NLAANVRAGE7210418,A patent/NL176254C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL176254B (nl) | 1984-10-16 |
| NL7210418A (ru) | 1973-01-30 |
| CA982148A (en) | 1976-01-20 |
| NO137500B (no) | 1977-11-28 |
| GB1374367A (en) | 1974-11-20 |
| IE36607L (en) | 1973-01-28 |
| SE399702B (sv) | 1978-02-27 |
| FR2147277B1 (ru) | 1976-04-16 |
| JPS565220B1 (ru) | 1981-02-04 |
| DK142843C (ru) | 1981-08-31 |
| AU4488672A (en) | 1974-01-31 |
| IE36607B1 (en) | 1976-12-08 |
| DE2235745B2 (de) | 1976-08-19 |
| AR193748A1 (es) | 1973-05-22 |
| PL84891B1 (en) | 1976-04-30 |
| ZA724512B (en) | 1973-08-29 |
| AU476000B2 (en) | 1976-09-09 |
| NO137500C (no) | 1978-03-08 |
| AT317185B (de) | 1974-08-12 |
| ES404739A1 (es) | 1975-07-16 |
| FI55492B (fi) | 1979-04-30 |
| SU441704A3 (ru) | 1974-08-30 |
| FR2147277A1 (ru) | 1973-03-09 |
| FI55492C (fi) | 1979-08-10 |
| CH574397A5 (ru) | 1976-04-15 |
| DD101389A5 (ru) | 1973-11-05 |
| DE2235745A1 (de) | 1973-02-22 |
| CS171171B2 (ru) | 1976-10-29 |
| BR7205069D0 (pt) | 1973-07-17 |
| HU163818B (ru) | 1973-11-28 |
| NL176254C (nl) | 1985-03-18 |
| BE786875A (fr) | 1973-01-29 |
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