CA1118355A - Compsitions containing alkannin derivatives for treating skin disorders - Google Patents
Compsitions containing alkannin derivatives for treating skin disordersInfo
- Publication number
- CA1118355A CA1118355A CA000294371A CA294371A CA1118355A CA 1118355 A CA1118355 A CA 1118355A CA 000294371 A CA000294371 A CA 000294371A CA 294371 A CA294371 A CA 294371A CA 1118355 A CA1118355 A CA 1118355A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- extract
- methyl
- lipophil
- alkannin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- NEZONWMXZKDMKF-JTQLQIEISA-N Alkannin Chemical class C1=CC(O)=C2C(=O)C([C@@H](O)CC=C(C)C)=CC(=O)C2=C1O NEZONWMXZKDMKF-JTQLQIEISA-N 0.000 title claims abstract description 30
- 208000017520 skin disease Diseases 0.000 title claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000004480 active ingredient Substances 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 150000001735 carboxylic acids Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- PQJUMPXLDAZULJ-UHFFFAOYSA-N 4-hydroxy-4-methylpentanoic acid Chemical group CC(C)(O)CCC(O)=O PQJUMPXLDAZULJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012298 atmosphere Substances 0.000 claims abstract description 3
- UNNKKUDWEASWDN-UHFFFAOYSA-N alkannin Natural products CC(=CCC(O)c1cc(O)c2C(=O)C=CC(=O)c2c1O)C UNNKKUDWEASWDN-UHFFFAOYSA-N 0.000 claims description 30
- 239000004229 Alkannin Substances 0.000 claims description 24
- 235000019232 alkannin Nutrition 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 239000002674 ointment Substances 0.000 claims description 21
- 239000000284 extract Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 16
- 241000196324 Embryophyta Species 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 241000118825 Alkanna tinctoria Species 0.000 claims description 8
- 241001071917 Lithospermum Species 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000004006 olive oil Substances 0.000 claims description 8
- 235000008390 olive oil Nutrition 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000001993 wax Substances 0.000 claims description 5
- 239000000419 plant extract Substances 0.000 claims description 4
- 150000003626 triacylglycerols Chemical class 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920000175 Pistacia lentiscus Polymers 0.000 claims description 3
- 235000013871 bee wax Nutrition 0.000 claims description 3
- 239000012166 beeswax Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 241000130781 Arnebia Species 0.000 claims description 2
- 241000167854 Bourreria succulenta Species 0.000 claims description 2
- 241000785079 Jatropha glandulifera Species 0.000 claims description 2
- 235000019693 cherries Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims 3
- 239000008158 vegetable oil Substances 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 206010040943 Skin Ulcer Diseases 0.000 abstract description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 230000035876 healing Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- -1 Desoxy alkannin Chemical compound 0.000 description 5
- 206010052428 Wound Diseases 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003883 ointment base Substances 0.000 description 2
- 230000004526 pharmaceutical effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
- 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 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 235000017847 Anchusa officinalis Nutrition 0.000 description 1
- 241001072256 Boraginaceae Species 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000505344 Macrotomia Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 206010072170 Skin wound Diseases 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 206010053615 Thermal burn Diseases 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- CFZLNSBZTUMWNS-UHFFFAOYSA-N benzene;chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl.C1=CC=CC=C1 CFZLNSBZTUMWNS-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- LLHRMWHYJGLIEV-UHFFFAOYSA-N desoxy Chemical group COC1=CC(CCN)=CC(OC)=C1C LLHRMWHYJGLIEV-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 231100000019 skin ulcer Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/32—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
-
- 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
- A61K31/12—Ketones
-
- 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
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2700448.4-41 | 1977-01-07 | ||
| DE2700448A DE2700448C2 (de) | 1977-01-07 | 1977-01-07 | Salbe zur Behandlung von Ulcus Cruris |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1118355A true CA1118355A (en) | 1982-02-16 |
Family
ID=5998230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000294371A Expired CA1118355A (en) | 1977-01-07 | 1978-01-05 | Compsitions containing alkannin derivatives for treating skin disorders |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4282250A (en, 2012) |
| JP (1) | JPS5391141A (en, 2012) |
| AT (1) | AT367295B (en, 2012) |
| CA (1) | CA1118355A (en, 2012) |
| CH (1) | CH633182A5 (en, 2012) |
| DE (1) | DE2700448C2 (en, 2012) |
| FR (1) | FR2376660A1 (en, 2012) |
| GB (1) | GB1574397A (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59175449A (ja) * | 1983-03-26 | 1984-10-04 | Kyushu Kogyo Daigaku | シコニンの製造法 |
| DE3340806C2 (de) * | 1983-11-11 | 1986-04-10 | NATEC Institut für naturwissenschaftlich-technische Dienste GmbH, 2000 Hamburg | Platinkomplexverbindungen substituierter 5,8-Dihydroxy-1,4-naphtochinone, Verfahren zu ihrer Herstellung und ihre Verwendung |
| GB2159056A (en) * | 1984-04-04 | 1985-11-27 | Alan Alaexander Torrance Sime | Biocidal compositions comprising polyhydroxynaphthoquinones |
| US4588831A (en) * | 1984-11-09 | 1986-05-13 | Natec | Platinum complex compounds of substituted 5,8-dihydroxyl-1,4-naphthoquinone, and process for their production and use |
| US4778787A (en) * | 1985-12-20 | 1988-10-18 | Trustees Of Boston University | Method for treatment of angina and myocardial infarctions with omental lipids |
| DE3620685A1 (de) * | 1986-06-20 | 1987-12-23 | Henkel Kgaa | Neue mittel zur abdeckung unverletzter und/oder verletzter bereiche menschlicher oder tierischer haut |
| CN1045059C (zh) * | 1993-01-15 | 1999-09-15 | 徐荣祥 | 一种治疗温血动物或人类热损伤的药用组合物及其制法 |
| GB2276392B (en) * | 1993-02-22 | 1997-03-26 | D G P | Improved production of natural flavours and fragrances |
| CN1046631C (zh) * | 1995-03-18 | 1999-11-24 | 新疆维吾尔自治区林业科学研究院 | 紫草色素抑菌唇膏 |
| GR1003550B (el) * | 1999-09-22 | 2001-03-13 | Σταθερο παρασκευασμα ισοεξυλοναφθαζαρινων με πεντα- και τετρα-κυκλικα τριτερπενια, συστατικα φυτικων ελαιορητινων και κομμεων | |
| WO2002078652A1 (en) * | 2001-03-30 | 2002-10-10 | Council Of Scientific And Industrial Research | Safe, eco-friendly, health protective herbal colours and aroma useful for cosmaceutical applications |
| TWI401098B (zh) * | 2010-09-09 | 2013-07-11 | Univ China Medical | 傷口敷料 |
| EP3364988B1 (en) * | 2015-10-22 | 2021-07-28 | Karaman Ozlu, Zeynep | Wound care composition |
| WO2017142491A1 (en) * | 2016-02-18 | 2017-08-24 | Özkök Gufran | Enhanced burn treatment cream and production method |
-
1977
- 1977-01-07 DE DE2700448A patent/DE2700448C2/de not_active Expired
-
1978
- 1978-01-05 AT AT0009678A patent/AT367295B/de not_active IP Right Cessation
- 1978-01-05 CH CH9978A patent/CH633182A5/de not_active IP Right Cessation
- 1978-01-05 CA CA000294371A patent/CA1118355A/en not_active Expired
- 1978-01-06 US US05/867,532 patent/US4282250A/en not_active Expired - Lifetime
- 1978-01-07 JP JP39578A patent/JPS5391141A/ja active Pending
- 1978-01-09 FR FR7800406A patent/FR2376660A1/fr active Granted
- 1978-01-09 GB GB778/78A patent/GB1574397A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2376660A1 (fr) | 1978-08-04 |
| DE2700448A1 (de) | 1978-07-20 |
| JPS5391141A (en) | 1978-08-10 |
| ATA9678A (de) | 1981-11-15 |
| CH633182A5 (de) | 1982-11-30 |
| DE2700448C2 (de) | 1982-11-11 |
| GB1574397A (en) | 1980-09-03 |
| FR2376660B1 (en, 2012) | 1981-11-06 |
| US4282250A (en) | 1981-08-04 |
| AT367295B (de) | 1982-06-25 |
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