IE47594B1 - Medicaments acting notably on the central nervous system based on ethyl 2-aryl allophanates - Google Patents
Medicaments acting notably on the central nervous system based on ethyl 2-aryl allophanatesInfo
- Publication number
- IE47594B1 IE47594B1 IE2353/78A IE235378A IE47594B1 IE 47594 B1 IE47594 B1 IE 47594B1 IE 2353/78 A IE2353/78 A IE 2353/78A IE 235378 A IE235378 A IE 235378A IE 47594 B1 IE47594 B1 IE 47594B1
- Authority
- IE
- Ireland
- Prior art keywords
- scs
- ethyl
- allophanate
- aryl
- phenyl
- Prior art date
Links
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims abstract description 32
- 239000003814 drug Substances 0.000 title claims abstract description 21
- 210000003169 central nervous system Anatomy 0.000 title claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims abstract 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract 2
- VCGUVRCFKLUCRS-UHFFFAOYSA-N ethyl n-carbamoyl-n-phenylcarbamate Chemical group CCOC(=O)N(C(N)=O)C1=CC=CC=C1 VCGUVRCFKLUCRS-UHFFFAOYSA-N 0.000 claims description 27
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 24
- FTERQIIEPDJLQN-UHFFFAOYSA-N ethyl n-carbamoyl-n-[2-(trifluoromethyl)phenyl]carbamate Chemical group CCOC(=O)N(C(N)=O)C1=CC=CC=C1C(F)(F)F FTERQIIEPDJLQN-UHFFFAOYSA-N 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 8
- 241001465754 Metazoa Species 0.000 abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 208000035475 disorder Diseases 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 43
- KQPKPCNLIDLUMF-UHFFFAOYSA-N secobarbital Chemical compound CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O KQPKPCNLIDLUMF-UHFFFAOYSA-N 0.000 description 32
- 229960002060 secobarbital Drugs 0.000 description 32
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 28
- 229960004815 meprobamate Drugs 0.000 description 28
- 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 22
- 229960003529 diazepam Drugs 0.000 description 22
- BTPKCEPCEQYPJZ-UHFFFAOYSA-N ethyl n-(2-bromophenyl)-n-carbamoylcarbamate Chemical compound CCOC(=O)N(C(N)=O)C1=CC=CC=C1Br BTPKCEPCEQYPJZ-UHFFFAOYSA-N 0.000 description 20
- -1 aryl cyanamides Chemical class 0.000 description 17
- 230000000949 anxiolytic effect Effects 0.000 description 13
- UFLRKWJTMZTORL-UHFFFAOYSA-N ethyl n-carbamoyl-n-(4-methylphenyl)carbamate Chemical compound CCOC(=O)N(C(N)=O)C1=CC=C(C)C=C1 UFLRKWJTMZTORL-UHFFFAOYSA-N 0.000 description 13
- NYCSDKZTPBDZGE-UHFFFAOYSA-N ethyl n-(3-bromophenyl)-n-carbamoylcarbamate Chemical compound CCOC(=O)N(C(N)=O)C1=CC=CC(Br)=C1 NYCSDKZTPBDZGE-UHFFFAOYSA-N 0.000 description 12
- OPCVVGLOBPMWQG-UHFFFAOYSA-N ethyl n-(4-bromophenyl)-n-carbamoylcarbamate Chemical compound CCOC(=O)N(C(N)=O)C1=CC=C(Br)C=C1 OPCVVGLOBPMWQG-UHFFFAOYSA-N 0.000 description 12
- IMULWFGAZXIYLS-UHFFFAOYSA-N ethyl n-carbamoyl-n-(2,3-dimethylphenyl)carbamate Chemical compound CCOC(=O)N(C(N)=O)C1=CC=CC(C)=C1C IMULWFGAZXIYLS-UHFFFAOYSA-N 0.000 description 12
- NEGMEIHYNPTRGY-UHFFFAOYSA-N ethyl n-carbamoyl-n-(3-chlorophenyl)carbamate Chemical compound CCOC(=O)N(C(N)=O)C1=CC=CC(Cl)=C1 NEGMEIHYNPTRGY-UHFFFAOYSA-N 0.000 description 12
- JBXRVPQIENCZJO-UHFFFAOYSA-N ethyl n-carbamoyl-n-(4-chlorophenyl)carbamate Chemical compound CCOC(=O)N(C(N)=O)C1=CC=C(Cl)C=C1 JBXRVPQIENCZJO-UHFFFAOYSA-N 0.000 description 12
- 230000011514 reflex Effects 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- DIPOJLBMCDRHCA-UHFFFAOYSA-N ethyl n-carbamoyl-n-(2-chlorophenyl)carbamate Chemical compound CCOC(=O)N(C(N)=O)C1=CC=CC=C1Cl DIPOJLBMCDRHCA-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- XIKPYGNPUIVKGX-UHFFFAOYSA-N ethyl n-carbamoyl-n-[3-(trifluoromethyl)phenyl]carbamate Chemical compound CCOC(=O)N(C(N)=O)C1=CC=CC(C(F)(F)F)=C1 XIKPYGNPUIVKGX-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000002249 anxiolytic agent Substances 0.000 description 8
- 230000000147 hypnotic effect Effects 0.000 description 8
- 239000003158 myorelaxant agent Substances 0.000 description 8
- 231100000419 toxicity Toxicity 0.000 description 8
- 230000001988 toxicity Effects 0.000 description 8
- 206010010904 Convulsion Diseases 0.000 description 7
- 230000001079 digestive effect Effects 0.000 description 7
- 208000002193 Pain Diseases 0.000 description 6
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 6
- 230000001773 anti-convulsant effect Effects 0.000 description 6
- 239000003179 convulsant agent Substances 0.000 description 6
- 230000036461 convulsion Effects 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000036407 pain Effects 0.000 description 6
- 229960005152 pentetrazol Drugs 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 5
- 239000001961 anticonvulsive agent Substances 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 230000003387 muscular Effects 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 229960005453 strychnine Drugs 0.000 description 5
- 208000019901 Anxiety disease Diseases 0.000 description 4
- 241001279009 Strychnos toxifera Species 0.000 description 4
- 229960003965 antiepileptics Drugs 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000932 sedative agent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000036506 anxiety Effects 0.000 description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 230000001665 lethal effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000012345 traction test Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000001448 anilines Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000003001 depressive effect Effects 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010043994 Tonic convulsion Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000000146 antalgic effect Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000035874 hyperreactivity Effects 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 238000005303 weighing Methods 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7735907A FR2409752A1 (fr) | 1977-11-29 | 1977-11-29 | Medicament agissant notamment sur le systeme nerveux central a base d'aryl-2 allophanates d'ethyle |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE782353L IE782353L (en) | 1979-05-29 |
| IE47594B1 true IE47594B1 (en) | 1984-05-02 |
Family
ID=9198212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2353/78A IE47594B1 (en) | 1977-11-29 | 1978-11-28 | Medicaments acting notably on the central nervous system based on ethyl 2-aryl allophanates |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS606331B2 (ja) |
| BE (1) | BE872163A (ja) |
| CH (1) | CH635746A5 (ja) |
| DE (1) | DE2851495C2 (ja) |
| FR (1) | FR2409752A1 (ja) |
| GB (1) | GB2010812B (ja) |
| IE (1) | IE47594B1 (ja) |
| IT (1) | IT1107673B (ja) |
| LU (1) | LU80573A1 (ja) |
| NL (1) | NL7811642A (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2572726B1 (fr) * | 1984-11-08 | 1986-12-19 | Francaise Sucrerie | Phenyl-2 allophanate d'isopropyle, son procede d'obtention et son application dans le domaine pharmaceutique |
| WO2026057953A1 (fr) | 2024-09-13 | 2026-03-19 | Lesaffre Et Compagnie | Synthese d'ethanol par hydrogenation de dioxyde de carbone |
-
1977
- 1977-11-29 FR FR7735907A patent/FR2409752A1/fr active Granted
-
1978
- 1978-11-21 BE BE191846A patent/BE872163A/xx not_active IP Right Cessation
- 1978-11-23 GB GB7845728A patent/GB2010812B/en not_active Expired
- 1978-11-24 LU LU80573A patent/LU80573A1/xx unknown
- 1978-11-27 NL NL7811642A patent/NL7811642A/xx not_active Application Discontinuation
- 1978-11-28 IT IT52098/78A patent/IT1107673B/it active
- 1978-11-28 JP JP53147065A patent/JPS606331B2/ja not_active Expired
- 1978-11-28 IE IE2353/78A patent/IE47594B1/en unknown
- 1978-11-28 DE DE2851495A patent/DE2851495C2/de not_active Expired
- 1978-11-28 CH CH1218578A patent/CH635746A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2010812B (en) | 1982-05-19 |
| JPS606331B2 (ja) | 1985-02-18 |
| IE782353L (en) | 1979-05-29 |
| JPS5492939A (en) | 1979-07-23 |
| CH635746A5 (fr) | 1983-04-29 |
| FR2409752B1 (ja) | 1982-11-12 |
| LU80573A1 (fr) | 1979-06-15 |
| BE872163A (fr) | 1979-05-21 |
| FR2409752A1 (fr) | 1979-06-22 |
| IT7852098A0 (it) | 1978-11-28 |
| DE2851495C2 (de) | 1982-06-24 |
| NL7811642A (nl) | 1979-05-31 |
| IT1107673B (it) | 1985-11-25 |
| DE2851495A1 (de) | 1979-05-31 |
| GB2010812A (en) | 1979-07-04 |
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