DD204248A1 - Verfahren zur herstellung von 1-(2,4-dichlorphenoxy)-3 (3,4-dimethoxy-beta-phenethylamino)-propanol-(2) - Google Patents
Verfahren zur herstellung von 1-(2,4-dichlorphenoxy)-3 (3,4-dimethoxy-beta-phenethylamino)-propanol-(2) Download PDFInfo
- Publication number
- DD204248A1 DD204248A1 DD81234259A DD23425981A DD204248A1 DD 204248 A1 DD204248 A1 DD 204248A1 DD 81234259 A DD81234259 A DD 81234259A DD 23425981 A DD23425981 A DD 23425981A DD 204248 A1 DD204248 A1 DD 204248A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- dimethoxy
- beta
- reaction
- propanol
- acid
- Prior art date
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- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000001886 ciliary effect Effects 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
- 229960005156 digoxin Drugs 0.000 description 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
- 229960002768 dipyridamole Drugs 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- SNFOERUNNSHUGP-ZXZARUISSA-N erythrityl tetranitrate Chemical compound [O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@@H](O[N+]([O-])=O)CO[N+]([O-])=O SNFOERUNNSHUGP-ZXZARUISSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 229950000974 gitoxin Drugs 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000004130 lipolysis 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- XQUMBKMAOXEAKZ-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]propan-1-amine Chemical compound CCCNCCC1=CC=C(OC)C(OC)=C1 XQUMBKMAOXEAKZ-UHFFFAOYSA-N 0.000 description 1
- 208000009157 neurocirculatory asthenia Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 230000036513 peripheral conductance Effects 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 229940048346 phenethylamine hydrochloride Drugs 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- QDWJJTJNXAKQKD-UHFFFAOYSA-N trihexyphenidyl hydrochloride Chemical compound Cl.C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 QDWJJTJNXAKQKD-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD81234259A DD204248A1 (de) | 1981-10-21 | 1981-10-21 | Verfahren zur herstellung von 1-(2,4-dichlorphenoxy)-3 (3,4-dimethoxy-beta-phenethylamino)-propanol-(2) |
| EP82109607A EP0086256B1 (de) | 1981-10-21 | 1982-10-18 | 1-(2,4-Dichlorphenoxy)-3-(3,4-dimethoxy-Beta-phenethylamino)-2-propanol, Verfahren zu seiner Herstellung und dieses enthaltende pharmazeutische Zusammensetzungen |
| FI823563A FI79296C (fi) | 1981-10-21 | 1982-10-18 | Foerfarande foer framstaellning av 1-(2,4- diklorfenoxi)-3-(3,4-dimetoxi- -fenetylamino)-propanol-(2). |
| DE8282109607T DE3265640D1 (en) | 1981-10-21 | 1982-10-18 | 1-(2,4-dichlorophenoxy)-3-(3,4-dimethoxy-beta-phenethylamino)-propan-2-0l, processes for its preparation and pharmaceutical compositions containing it |
| AT82109607T ATE15031T1 (de) | 1981-10-21 | 1982-10-18 | 1-(2,4-dichlorphenoxy)-3-(3,4-dimethoxy-betaphenethylamino)-2-propanol, verfahren zu seiner herstellung und dieses enthaltende pharmazeutische zusammensetzungen. |
| NO823477A NO155052C (no) | 1981-10-21 | 1982-10-19 | Analogifremgangsmaate til fremstilling av 1-(2,4-diklorfenoksy)-3-(3,4-dimetoksy-b-fenetylamino)-propanol-(2). |
| YU2356/82A YU43530B (en) | 1981-10-21 | 1982-10-20 | Process for obtaining new racemic and optic active 1-(2,4-dichlorophenoxy)-3-(3,4-dimethoxy-beta-phenethyl-amino)-propanol-(2) |
| DK464982A DK154209C (da) | 1981-10-21 | 1982-10-20 | Analogifremgangsmaade til fremstilling af racemisk eller optisk aktivt 1-(2,4-dichlorphenoxy)-3-(3,4-dimethoxy-beta-phenethylamino)-propanol-(2) eller syreadditionssalte deraf |
| ES516723A ES8403855A1 (es) | 1981-10-21 | 1982-10-21 | "procedimiento para la preparacion de 1-(2,4-diclorofenoxi)-3-(3,4-dimetoxi-b-fenetilamino)-propanol-(2) racemico y opticamente activo". |
| SU823506785A SU1507763A1 (ru) | 1981-10-21 | 1982-10-21 | Рацемический 1-(2,4-дихлорфенокси)-3-(3,4-диметокси- @ -фенетиламино)-пропанол-2 или его гидрохлорид, обладающие гипотензивным действием |
| JP57185341A JPS58131946A (ja) | 1981-10-21 | 1982-10-21 | １−（２，４−ジクロロフエノキシ）−３−（３，４−ジメトキシ−β−フエネチルアミノ）−プロパノ−ル−（２），その製造法およびその用途 |
| CS827489A CS247552B1 (en) | 1981-10-21 | 1982-10-21 | 1-(2,4-dichlorophenoxy)-3-(3,4-dimethoxy-beta-phenethylamino)-2-propanol and its additional salts with acids |
| BG8258364A BG40396A1 (en) | 1981-10-21 | 1982-10-21 | 1- (2, 4- dichlorphenoxy)- 3- (3, 4- dimetoxy- beta- phenetylamino)- propanol- (2), method for its preparation and use thereof |
| HU823371A HU190994B (en) | 1981-10-21 | 1982-10-21 | Process for producing 1-/-2,4-dichloro-phenoxy/-3-/-3,4-dimethoxy-beta-phenetyl-amino-/-2-propanol |
| ES529193A ES8500617A1 (es) | 1981-10-21 | 1984-01-26 | Procedimiento para la preparacion de 1-(2, 4-diclorofenoxi)-3-(3, 4-dimetoxi-b-fenetilamino)-propanol-(2) racemico y opticamente activo |
| ES529192A ES529192A0 (es) | 1981-10-21 | 1984-01-26 | Procedimiento para la preparacion de 1-(2,4-diciclorofenoxi)-3-(3,4-dimetoxi-b-fenetilamino)-propanol-2 racemico y op- ticamente activo. |
| YU00667/85A YU66785A (en) | 1981-10-21 | 1985-04-22 | Process for the manufacture of a new, recemic and opticall active 1-(2,4-dichlorophenxy)-3-(3,4-dimethoxy-beta-phenethylamino)-propanol-(2) |
| YU00666/85A YU66685A (en) | 1981-10-21 | 1985-04-22 | Process for the manufacturing of a new, racemic and optically active 1-(2,4-dichlorophenoxy)-3-(3,4-dimethoxy-beta-phenethylamino)-propanol-(2) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD81234259A DD204248A1 (de) | 1981-10-21 | 1981-10-21 | Verfahren zur herstellung von 1-(2,4-dichlorphenoxy)-3 (3,4-dimethoxy-beta-phenethylamino)-propanol-(2) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD204248A1 true DD204248A1 (de) | 1983-11-23 |
Family
ID=5534243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81234259A DD204248A1 (de) | 1981-10-21 | 1981-10-21 | Verfahren zur herstellung von 1-(2,4-dichlorphenoxy)-3 (3,4-dimethoxy-beta-phenethylamino)-propanol-(2) |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0086256B1 (en, 2012) |
| JP (1) | JPS58131946A (en, 2012) |
| AT (1) | ATE15031T1 (en, 2012) |
| BG (1) | BG40396A1 (en, 2012) |
| CS (1) | CS247552B1 (en, 2012) |
| DD (1) | DD204248A1 (en, 2012) |
| DE (1) | DE3265640D1 (en, 2012) |
| DK (1) | DK154209C (en, 2012) |
| ES (3) | ES8403855A1 (en, 2012) |
| FI (1) | FI79296C (en, 2012) |
| HU (1) | HU190994B (en, 2012) |
| NO (1) | NO155052C (en, 2012) |
| SU (1) | SU1507763A1 (en, 2012) |
| YU (3) | YU43530B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62156230A (ja) * | 1985-12-27 | 1987-07-11 | Nippon Steel Corp | 帯状物の蛇行修正方法 |
-
1981
- 1981-10-21 DD DD81234259A patent/DD204248A1/de unknown
-
1982
- 1982-10-18 FI FI823563A patent/FI79296C/fi not_active IP Right Cessation
- 1982-10-18 DE DE8282109607T patent/DE3265640D1/de not_active Expired
- 1982-10-18 EP EP82109607A patent/EP0086256B1/de not_active Expired
- 1982-10-18 AT AT82109607T patent/ATE15031T1/de not_active IP Right Cessation
- 1982-10-19 NO NO823477A patent/NO155052C/no unknown
- 1982-10-20 DK DK464982A patent/DK154209C/da not_active IP Right Cessation
- 1982-10-20 YU YU2356/82A patent/YU43530B/xx unknown
- 1982-10-21 CS CS827489A patent/CS247552B1/cs unknown
- 1982-10-21 BG BG8258364A patent/BG40396A1/xx unknown
- 1982-10-21 ES ES516723A patent/ES8403855A1/es not_active Expired
- 1982-10-21 HU HU823371A patent/HU190994B/hu not_active IP Right Cessation
- 1982-10-21 SU SU823506785A patent/SU1507763A1/ru active
- 1982-10-21 JP JP57185341A patent/JPS58131946A/ja active Granted
-
1984
- 1984-01-26 ES ES529192A patent/ES529192A0/es active Granted
- 1984-01-26 ES ES529193A patent/ES8500617A1/es not_active Expired
-
1985
- 1985-04-22 YU YU00666/85A patent/YU66685A/xx unknown
- 1985-04-22 YU YU00667/85A patent/YU66785A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU66685A (en) | 1985-10-31 |
| EP0086256B1 (de) | 1985-08-21 |
| DK154209B (da) | 1988-10-24 |
| BG40396A1 (en) | 1986-12-15 |
| NO155052C (no) | 1987-02-04 |
| ES529193A0 (es) | 1984-11-16 |
| FI823563L (fi) | 1983-04-22 |
| FI79296B (fi) | 1989-08-31 |
| HU190994B (en) | 1986-12-28 |
| ATE15031T1 (de) | 1985-09-15 |
| ES516723A0 (es) | 1984-05-01 |
| NO155052B (no) | 1986-10-27 |
| YU66785A (en) | 1985-10-31 |
| YU235682A (en) | 1985-08-31 |
| ES8403855A1 (es) | 1984-05-01 |
| DE3265640D1 (en) | 1985-09-26 |
| JPS6311347B2 (en, 2012) | 1988-03-14 |
| ES8500617A1 (es) | 1984-11-16 |
| ES8407317A1 (es) | 1984-10-01 |
| EP0086256A1 (de) | 1983-08-24 |
| NO823477L (no) | 1983-04-22 |
| JPS58131946A (ja) | 1983-08-06 |
| FI823563A0 (fi) | 1982-10-18 |
| DK464982A (da) | 1983-04-22 |
| ES529192A0 (es) | 1984-10-01 |
| FI79296C (fi) | 1989-12-11 |
| SU1507763A1 (ru) | 1989-09-15 |
| YU43530B (en) | 1989-08-31 |
| DK154209C (da) | 1989-03-20 |
| CS247552B1 (en) | 1987-01-15 |
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