DE2653405A1 - 16beta-alkyl eckige klammer auf 16alpha,17-beta eckige klammer zu naphthalin-steroide der pregnanreihe, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
16beta-alkyl eckige klammer auf 16alpha,17-beta eckige klammer zu naphthalin-steroide der pregnanreihe, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE2653405A1 DE2653405A1 DE19762653405 DE2653405A DE2653405A1 DE 2653405 A1 DE2653405 A1 DE 2653405A1 DE 19762653405 DE19762653405 DE 19762653405 DE 2653405 A DE2653405 A DE 2653405A DE 2653405 A1 DE2653405 A1 DE 2653405A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- alkyl
- hydrogen
- atom
- dione
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 3
- JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 title claims description 3
- -1 NAPHTHALINE STEROIDS Chemical class 0.000 title description 10
- 229940126601 medicinal product Drugs 0.000 title description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 150000003431 steroids Chemical class 0.000 claims description 9
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BZWJDKJBAVXCMH-UHFFFAOYSA-N 1-diazopropane Chemical compound CCC=[N+]=[N-] BZWJDKJBAVXCMH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YVPGZUWNVLRAKT-XYNXPQAZSA-N [2-[(8s,9r,10s,11s,13s,14s)-9-fluoro-11-hydroxy-10,13-dimethyl-3-oxo-7,8,11,12,14,15-hexahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC=C(C(=O)COC(=O)C)[C@@]1(C)C[C@@H]2O YVPGZUWNVLRAKT-XYNXPQAZSA-N 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UVOTVQIUSZDLAM-GGLFOPPFSA-N (8s,9s,10r,11s,13s,14s)-17-acetyl-11-hydroxy-10,13-dimethyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)C[C@@H]2O UVOTVQIUSZDLAM-GGLFOPPFSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000003862 glucocorticoid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SFLFWFVCRZBSIC-HTQZYQBOSA-N (7r,8r)-7,8-dibromobicyclo[4.2.0]octa-1,3,5-triene Chemical compound C1=CC=C2[C@@H](Br)[C@H](Br)C2=C1 SFLFWFVCRZBSIC-HTQZYQBOSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- IHDRXDWUDBSDAN-UHFFFAOYSA-N 2-diazopropane Chemical compound CC(C)=[N+]=[N-] IHDRXDWUDBSDAN-UHFFFAOYSA-N 0.000 description 1
- XWIPDNKTOPDTBQ-UHFFFAOYSA-N 7-bicyclo[4.2.0]octa-1,3,5-trienyl acetate Chemical compound C1=CC=C2C(OC(=O)C)CC2=C1 XWIPDNKTOPDTBQ-UHFFFAOYSA-N 0.000 description 1
- KZQCCCQLHQIETD-UHFFFAOYSA-N 7-phenylbicyclo[4.2.0]octa-1,3,5-triene Chemical compound C12=CC=CC=C2CC1C1=CC=CC=C1 KZQCCCQLHQIETD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZDKMGZMVVKEAAJ-KCRBMJMASA-N CC(=O)OCC(=O)C1=CC[C@@H]2[C@@]1(CC[C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)C Chemical compound CC(=O)OCC(=O)C1=CC[C@@H]2[C@@]1(CC[C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)C ZDKMGZMVVKEAAJ-KCRBMJMASA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 201000009053 Neurodermatitis Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- UFEOMHFPJREVTP-PTRHGPIFSA-N [2-[(8s,10s,13s,14s)-10,13-dimethyl-3-oxo-6,7,8,12,14,15-hexahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound O=C1C=C[C@]2(C)C3=CC[C@]4(C)C(C(=O)COC(=O)C)=CC[C@H]4[C@@H]3CCC2=C1 UFEOMHFPJREVTP-PTRHGPIFSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- BKYGJFIVXHTOPC-UHFFFAOYSA-N cyclobutene Chemical compound [CH]1CC=C1 BKYGJFIVXHTOPC-UHFFFAOYSA-N 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 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
- 150000004702 methyl esters Chemical class 0.000 description 1
- HSPSCWZIJWKZKD-UHFFFAOYSA-N n-chloroacetamide Chemical compound CC(=O)NCl HSPSCWZIJWKZKD-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0042—Nitrogen only
- C07J71/0052—Nitrogen only at position 16(17)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/634,684 US3994935A (en) | 1975-11-24 | 1975-11-24 | Steroidal 16β-alkyl[16α,17-b]naphthalenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2653405A1 true DE2653405A1 (de) | 1977-05-26 |
Family
ID=24544809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762653405 Ceased DE2653405A1 (de) | 1975-11-24 | 1976-11-24 | 16beta-alkyl eckige klammer auf 16alpha,17-beta eckige klammer zu naphthalin-steroide der pregnanreihe, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3994935A (enExample) |
| JP (1) | JPS5265260A (enExample) |
| CA (1) | CA1088516A (enExample) |
| DE (1) | DE2653405A1 (enExample) |
| FR (1) | FR2332021A1 (enExample) |
| GB (1) | GB1569993A (enExample) |
| MX (1) | MX4033E (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091036A (en) * | 1977-05-12 | 1978-05-23 | E. R. Squibb & Sons, Inc. | 17-Alkylthio (and arylthio)-1',2',3',4'-tetrahydroandrosteno [16 α, 17 α-b]naphthalenes and derivatives |
| US4232013A (en) * | 1977-12-03 | 1980-11-04 | Lark S.P.A. | 16,17-Pyrazolino- and 16,17-isopyrazolino-1,4-pregnadiene derivatives |
| US4265815A (en) * | 1980-03-31 | 1981-05-05 | E. R. Squibb & Sons, Inc. | 17-(Substituted thio)androst-4-ene[16,17,-b]-[1,4]benzodioxin-3-ones |
| DE3510300A1 (de) * | 1985-03-22 | 1986-09-25 | Alfred Teves GmbH & Co oHG, 5275 Bergneustadt | Befestigungsschraube, insbesondere fuer stossfaenger von kraftfahrzeugen |
| DE102005061528B8 (de) * | 2005-12-22 | 2010-06-10 | Siemens Ag | Piezokeramisches Bauteil mit Bleizirkonattitanat mit Eisen-Wolfram-Dotierung, Verfahren zum Herstellen des piezokeramischen Bauteils und seine Verwendung |
| US8316865B2 (en) | 2008-07-31 | 2012-11-27 | Mcneil-Ppc, Inc. | Process for winding dental tape |
| HUE038046T2 (hu) * | 2010-12-17 | 2018-09-28 | Reata Pharmaceuticals Inc | Antioxidáns gyulladáscsökkentõ pirazolil és pirimidinil triciklusos enonok |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3944584A (en) * | 1975-02-03 | 1976-03-16 | E. R. Squibb & Sons, Inc. | Steroidal (16α,17-d)cyclohexenes |
-
1975
- 1975-11-24 US US05/634,684 patent/US3994935A/en not_active Expired - Lifetime
-
1976
- 1976-11-09 CA CA265,279A patent/CA1088516A/en not_active Expired
- 1976-11-10 GB GB46811/76A patent/GB1569993A/en not_active Expired
- 1976-11-23 MX MX765147U patent/MX4033E/es unknown
- 1976-11-24 JP JP51141751A patent/JPS5265260A/ja active Pending
- 1976-11-24 FR FR7635413A patent/FR2332021A1/fr active Granted
- 1976-11-24 DE DE19762653405 patent/DE2653405A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US3994935A (en) | 1976-11-30 |
| MX4033E (es) | 1981-11-18 |
| FR2332021A1 (fr) | 1977-06-17 |
| FR2332021B1 (enExample) | 1982-08-13 |
| JPS5265260A (en) | 1977-05-30 |
| CA1088516A (en) | 1980-10-28 |
| GB1569993A (en) | 1980-06-25 |
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