CA1052271A - 1,2 - and 2,3 - epoxy alkanes - Google Patents
1,2 - and 2,3 - epoxy alkanesInfo
- Publication number
- CA1052271A CA1052271A CA221,651A CA221651A CA1052271A CA 1052271 A CA1052271 A CA 1052271A CA 221651 A CA221651 A CA 221651A CA 1052271 A CA1052271 A CA 1052271A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- formula
- epoxy
- carbon atoms
- epoxy alkanes
- 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
- 239000004593 Epoxy Substances 0.000 title abstract description 16
- 150000001335 aliphatic alkanes Chemical class 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 210000002307 prostate Anatomy 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
- 230000003248 secreting effect Effects 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 16
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract description 6
- 206010036940 Prostatic adenoma Diseases 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 16
- 210000000981 epithelium Anatomy 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 230000000875 corresponding effect Effects 0.000 description 10
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000003981 vehicle Substances 0.000 description 7
- VHMBMZSDFOQAHR-HWKANZROSA-N (e)-icos-2-ene Chemical compound CCCCCCCCCCCCCCCCC\C=C\C VHMBMZSDFOQAHR-HWKANZROSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 150000004965 peroxy acids Chemical class 0.000 description 5
- VGYBKPBFRIXAST-UHFFFAOYSA-N 2-heptadecyl-3-methyloxirane Chemical compound CCCCCCCCCCCCCCCCCC1OC1C VGYBKPBFRIXAST-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229940073584 methylene chloride Drugs 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- INJRDZMWIAYEMM-UHFFFAOYSA-N 9-Oxo-2-decenoic acid Natural products CC(=O)CCCCCC=CC(O)=O INJRDZMWIAYEMM-UHFFFAOYSA-N 0.000 description 2
- INJRDZMWIAYEMM-SOFGYWHQSA-N 9-Oxo-2E-decenoic acid Chemical compound CC(=O)CCCCC\C=C\C(O)=O INJRDZMWIAYEMM-SOFGYWHQSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- -1 chloromethylene Chemical group 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 210000004907 gland Anatomy 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- RHEVFAMQJMWLFS-UHFFFAOYSA-N icosan-2-ol Chemical compound CCCCCCCCCCCCCCCCCCC(C)O RHEVFAMQJMWLFS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- HFOFYNMWYRXIBP-MOPGFXCFSA-N 2-methyl-7S,8R-Epoxy-octadecane Chemical compound CCCCCCCCCC[C@H]1O[C@H]1CCCCC(C)C HFOFYNMWYRXIBP-MOPGFXCFSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 206010061926 Purulence Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000027326 copulation Effects 0.000 description 1
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036732 histological change Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1068374A GB1453392A (en) | 1974-03-11 | 1974-03-11 | Epoxides and their therapeutic application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052271A true CA1052271A (en) | 1979-04-10 |
Family
ID=9972360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,651A Expired CA1052271A (en) | 1974-03-11 | 1975-03-10 | 1,2 - and 2,3 - epoxy alkanes |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS50135008A (es) |
| AR (1) | AR206223A1 (es) |
| AT (1) | AT342612B (es) |
| BE (1) | BE826488A (es) |
| CA (1) | CA1052271A (es) |
| CH (1) | CH594652A5 (es) |
| DE (2) | DE2509503C3 (es) |
| DK (1) | DK80375A (es) |
| ES (1) | ES435479A1 (es) |
| FI (1) | FI60001C (es) |
| FR (1) | FR2263761B1 (es) |
| GB (1) | GB1453392A (es) |
| IE (1) | IE40822B1 (es) |
| IL (1) | IL46785A (es) |
| NL (1) | NL7502845A (es) |
| NO (1) | NO144151C (es) |
| SE (1) | SE420724B (es) |
| ZA (1) | ZA751489B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3633655A (en) * | 1970-09-23 | 1972-01-11 | United States Steel Corp | Construction for connecting and aligning sections of a guide-roll rack |
| US4890714A (en) * | 1986-02-14 | 1990-01-02 | Brown H Gary | Conveying system |
-
1974
- 1974-03-11 GB GB1068374A patent/GB1453392A/en not_active Expired
-
1975
- 1975-01-01 AR AR257927A patent/AR206223A1/es active
- 1975-02-28 DK DK80375*#A patent/DK80375A/da not_active Application Discontinuation
- 1975-03-05 DE DE2509503A patent/DE2509503C3/de not_active Expired
- 1975-03-05 FR FR7506913A patent/FR2263761B1/fr not_active Expired
- 1975-03-05 DE DE2559764A patent/DE2559764C2/de not_active Expired
- 1975-03-10 SE SE7502641A patent/SE420724B/xx unknown
- 1975-03-10 NO NO750785A patent/NO144151C/no unknown
- 1975-03-10 IL IL46785A patent/IL46785A/xx unknown
- 1975-03-10 BE BE154179A patent/BE826488A/xx not_active IP Right Cessation
- 1975-03-10 ES ES435479A patent/ES435479A1/es not_active Expired
- 1975-03-10 CA CA221,651A patent/CA1052271A/en not_active Expired
- 1975-03-11 NL NL7502845A patent/NL7502845A/xx not_active Application Discontinuation
- 1975-03-11 JP JP50029975A patent/JPS50135008A/ja active Pending
- 1975-03-11 IE IE525/75A patent/IE40822B1/xx unknown
- 1975-03-11 FI FI750692A patent/FI60001C/fi not_active IP Right Cessation
- 1975-03-11 ZA ZA00751489A patent/ZA751489B/xx unknown
- 1975-03-11 CH CH308675A patent/CH594652A5/xx not_active IP Right Cessation
- 1975-03-11 AT AT185975A patent/AT342612B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA751489B (en) | 1976-02-25 |
| NO750785L (es) | 1975-09-12 |
| FI60001B (fi) | 1981-07-31 |
| AR206223A1 (es) | 1976-07-07 |
| DE2509503C3 (de) | 1980-12-18 |
| JPS50135008A (es) | 1975-10-25 |
| BE826488A (fr) | 1975-06-30 |
| FR2263761A1 (es) | 1975-10-10 |
| IL46785A (en) | 1978-06-15 |
| NO144151B (no) | 1981-03-23 |
| DE2509503B2 (de) | 1980-04-24 |
| ES435479A1 (es) | 1977-01-01 |
| IE40822L (en) | 1975-09-11 |
| SE7502641L (sv) | 1975-09-12 |
| DK80375A (es) | 1975-09-12 |
| IE40822B1 (en) | 1979-08-29 |
| AU7897575A (en) | 1976-09-16 |
| DE2509503A1 (de) | 1975-09-18 |
| FI750692A (es) | 1975-09-12 |
| AT342612B (de) | 1978-04-10 |
| NL7502845A (nl) | 1975-09-15 |
| IL46785A0 (en) | 1975-05-22 |
| FR2263761B1 (es) | 1980-02-22 |
| GB1453392A (en) | 1976-10-20 |
| DE2559764C2 (de) | 1983-05-05 |
| NO144151C (no) | 1981-07-01 |
| CH594652A5 (es) | 1978-01-13 |
| SE420724B (sv) | 1981-10-26 |
| FI60001C (fi) | 1981-11-10 |
| ATA185975A (de) | 1977-08-15 |
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