IL44903A - 71 - Hydroxy - 61, 61 - Dimethiester - 4 - An - 3 - On, its preparation and pharmaceutical preparations containing it - Google Patents
71 - Hydroxy - 61, 61 - Dimethiester - 4 - An - 3 - On, its preparation and pharmaceutical preparations containing itInfo
- Publication number
- IL44903A IL44903A IL44903A IL4490374A IL44903A IL 44903 A IL44903 A IL 44903A IL 44903 A IL44903 A IL 44903A IL 4490374 A IL4490374 A IL 4490374A IL 44903 A IL44903 A IL 44903A
- Authority
- IL
- Israel
- Prior art keywords
- dimethylestr
- hydroxy
- parts
- preparation
- pharmaceutical compositions
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- JYCITEUSLNKPHC-URNBORRASA-N metogest Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC(C)(C)[C@H](O)[C@@]1(C)CC2 JYCITEUSLNKPHC-URNBORRASA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 230000002280 anti-androgenic effect Effects 0.000 abstract description 4
- 230000002086 anti-sebum Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 150000003431 steroids Chemical class 0.000 description 9
- 210000002307 prostate Anatomy 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 4
- 230000001548 androgenic effect Effects 0.000 description 4
- 235000005687 corn oil Nutrition 0.000 description 4
- 239000002285 corn oil Substances 0.000 description 4
- 239000007937 lozenge Substances 0.000 description 4
- -1 monomethyl steroid Chemical class 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001195 anabolic effect Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000008174 sterile solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 210000004907 gland Anatomy 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- 210000001625 seminal vesicle Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960003604 testosterone Drugs 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 201000010653 vesiculitis Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-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
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000282346 Meles meles Species 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007943 implant Substances 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
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Dental Preparations (AREA)
- Detergent Compositions (AREA)
- Medicinal Preparation (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00364340A US3853926A (en) | 1973-05-29 | 1973-05-29 | 17{62 -hydroxy-16,16-dimethylester-4-en-3-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44903A0 IL44903A0 (en) | 1974-07-31 |
| IL44903A true IL44903A (en) | 1977-05-31 |
Family
ID=23434065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44903A IL44903A (en) | 1973-05-29 | 1974-05-28 | 71 - Hydroxy - 61, 61 - Dimethiester - 4 - An - 3 - On, its preparation and pharmaceutical preparations containing it |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3853926A (fr) |
| JP (1) | JPS5019745A (fr) |
| AR (1) | AR199619A1 (fr) |
| AT (1) | AT333990B (fr) |
| BE (1) | BE815626A (fr) |
| CA (1) | CA1033716A (fr) |
| CH (1) | CH609705A5 (fr) |
| DE (1) | DE2425822A1 (fr) |
| DK (1) | DK132328C (fr) |
| ES (1) | ES426711A1 (fr) |
| FI (1) | FI53218C (fr) |
| FR (1) | FR2231383B1 (fr) |
| GB (1) | GB1416839A (fr) |
| HU (1) | HU168555B (fr) |
| IE (1) | IE39292B1 (fr) |
| IL (1) | IL44903A (fr) |
| NL (1) | NL7407122A (fr) |
| NO (1) | NO140104C (fr) |
| PH (1) | PH10428A (fr) |
| SE (1) | SE401835B (fr) |
| ZA (1) | ZA743304B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1538227A (en) * | 1975-03-21 | 1979-01-10 | Beecham Group Ltd | 16,16-disubstituted steroids of the androstene series |
| FI59534C (fi) * | 1979-10-31 | 1981-09-10 | Orion Yhtymae Oy | Vaordmedel foer fraemjande av haorvaext och hindrande av mjaell |
| GB9021546D0 (en) * | 1990-10-04 | 1990-11-21 | Beecham Group Plc | Novel composition |
| US6355687B1 (en) * | 2000-06-30 | 2002-03-12 | Unilever Home And Personal Care Usa, Division Of Conopco, Inc. | Cosmetic compositions containing substituted iminodibenzyl or fluorene derivatives |
| US6355686B1 (en) * | 2000-06-30 | 2002-03-12 | Unilever Home And Personal Care Usa, Division Of Conopco, Inc. | Cosmetic compositions containing substituted amine derivatives |
| US6372795B1 (en) * | 2000-06-30 | 2002-04-16 | Unilever Home And Personal Care Usa, A Division Of Conopco, Inc. | Cosmetic compositions containing substituted amide derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3049555A (en) * | 1959-12-22 | 1962-08-14 | Searle & Co | 3-alkoxy-16-methyl-1, 3, 5 (10)-estratrien-17-ones |
| US3280156A (en) * | 1965-10-13 | 1966-10-18 | Searle & Co | 17beta-hydroxyspiro(estr-4-ene-16, 1'-cyclopropan)-3-ones |
-
1973
- 1973-05-29 US US00364340A patent/US3853926A/en not_active Expired - Lifetime
-
1974
- 1974-05-22 ZA ZA00743304A patent/ZA743304B/xx unknown
- 1974-05-28 FI FI1632/74A patent/FI53218C/fi active
- 1974-05-28 SE SE7407031A patent/SE401835B/xx unknown
- 1974-05-28 IL IL44903A patent/IL44903A/en unknown
- 1974-05-28 DE DE19742425822 patent/DE2425822A1/de not_active Withdrawn
- 1974-05-28 NO NO741929A patent/NO140104C/no unknown
- 1974-05-28 PH PH15876A patent/PH10428A/en unknown
- 1974-05-28 JP JP49060202A patent/JPS5019745A/ja active Pending
- 1974-05-28 NL NL7407122A patent/NL7407122A/xx not_active Application Discontinuation
- 1974-05-28 DK DK289274A patent/DK132328C/da active
- 1974-05-28 ES ES426711A patent/ES426711A1/es not_active Expired
- 1974-05-28 IE IE1123/74A patent/IE39292B1/xx unknown
- 1974-05-28 CA CA200,995A patent/CA1033716A/fr not_active Expired
- 1974-05-28 AT AT438674A patent/AT333990B/de not_active IP Right Cessation
- 1974-05-28 HU HUSE1731A patent/HU168555B/hu unknown
- 1974-05-28 FR FR7418471A patent/FR2231383B1/fr not_active Expired
- 1974-05-28 BE BE144827A patent/BE815626A/fr unknown
- 1974-05-28 GB GB2351174A patent/GB1416839A/en not_active Expired
- 1974-05-29 AR AR253974A patent/AR199619A1/es active
- 1974-05-29 CH CH735574A patent/CH609705A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT333990B (de) | 1976-12-27 |
| US3853926A (en) | 1974-12-10 |
| NO140104C (no) | 1979-07-11 |
| DE2425822A1 (de) | 1975-01-02 |
| IE39292L (en) | 1974-11-29 |
| HU168555B (fr) | 1976-05-28 |
| IL44903A0 (en) | 1974-07-31 |
| ZA743304B (en) | 1976-01-28 |
| DK132328C (da) | 1976-05-31 |
| NL7407122A (fr) | 1974-12-03 |
| NO140104B (no) | 1979-03-26 |
| FI163274A (fr) | 1974-11-30 |
| GB1416839A (en) | 1975-12-10 |
| FI53218C (fr) | 1978-03-10 |
| FR2231383B1 (fr) | 1977-11-04 |
| CA1033716A (fr) | 1978-06-27 |
| FI53218B (fr) | 1977-11-30 |
| AU6945474A (en) | 1975-12-04 |
| SE7407031L (fr) | 1974-12-02 |
| FR2231383A1 (fr) | 1974-12-27 |
| JPS5019745A (fr) | 1975-03-01 |
| BE815626A (fr) | 1974-11-28 |
| PH10428A (en) | 1977-03-16 |
| IE39292B1 (en) | 1978-09-13 |
| ATA438674A (de) | 1976-04-15 |
| CH609705A5 (fr) | 1979-03-15 |
| NO741929L (no) | 1974-12-02 |
| SE401835B (sv) | 1978-05-29 |
| ES426711A1 (es) | 1976-08-01 |
| DK289274A (fr) | 1975-01-13 |
| DK132328B (da) | 1975-11-24 |
| AR199619A1 (es) | 1974-09-13 |
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