CH476708A - Verfahren zur Herstellung neuer 9B,10a-Steroide - Google Patents
Verfahren zur Herstellung neuer 9B,10a-SteroideInfo
- Publication number
- CH476708A CH476708A CH1333768A CH1333768A CH476708A CH 476708 A CH476708 A CH 476708A CH 1333768 A CH1333768 A CH 1333768A CH 1333768 A CH1333768 A CH 1333768A CH 476708 A CH476708 A CH 476708A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- acid
- steroids
- pregna
- new
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- -1 tetrahydropyranyloxy groups Chemical group 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000262 estrogen Substances 0.000 description 4
- 229940011871 estrogen Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RJKFOVLPORLFTN-NXMWLWCLSA-N (8s,9s,10s,13s,14s,17s)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-NXMWLWCLSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YXRFQWKNFFQPAQ-NXMWLWCLSA-N 1-[(8S,9S,10S,13S,14S,17S)-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound CC([C@H]1CC[C@H]2[C@@H]3CC=C4C=CCC[C@@]4(C)[C@H]3CC[C@]12C)=O YXRFQWKNFFQPAQ-NXMWLWCLSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003098 androgen Substances 0.000 description 2
- 230000001548 androgenic effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OIKWZAMGBNHJCU-UHFFFAOYSA-N 2,2-dimethylpropanoic acid Chemical compound CC(C)(C)C(O)=O.CC(C)(C)C(O)=O OIKWZAMGBNHJCU-UHFFFAOYSA-N 0.000 description 1
- GRYATKTXPZPERW-UHFFFAOYSA-N 2-(4-hexoxyphenyl)propanoic acid Chemical compound CCCCCCOC1=CC=C(C(C)C(O)=O)C=C1 GRYATKTXPZPERW-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- LKAJKIOFIWVMDJ-IYRCEVNGSA-N Stanazolol Chemical compound C([C@@H]1CC[C@H]2[C@@H]3CC[C@@]([C@]3(CC[C@@H]2[C@@]1(C)C1)C)(O)C)C2=C1C=NN2 LKAJKIOFIWVMDJ-IYRCEVNGSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 239000000051 antiandrogen Substances 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- BEZZFPOZAYTVHN-UHFFFAOYSA-N oxfendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1S(=O)C1=CC=CC=C1 BEZZFPOZAYTVHN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 230000001836 utereotrophic effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/12—Anthraquinone-azo dyes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/11—Preparation of azo dyes from other azo compounds by introducing hydrocarbon radicals or substituted hydrocarbon radicals on primary or secondary amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Arc Welding In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26744/64A GB1127601A (en) | 1964-06-29 | 1964-06-29 | Improvements in or relating to 10 ª‡-methyl steroid compounds |
| CH1233564A CH486437A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH476708A true CH476708A (de) | 1969-08-15 |
Family
ID=10248548
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1333768A CH476708A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1334068A CH476714A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1233564A CH486437A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1333668A CH478112A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1333568A CH480320A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1333968A CH476705A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1333868A CH476713A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1334068A CH476714A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1233564A CH486437A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1333668A CH478112A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1333568A CH480320A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1333968A CH476705A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
| CH1333868A CH476713A (de) | 1964-06-29 | 1964-09-23 | Verfahren zur Herstellung neuer 9B,10a-Steroide |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3422122A (en]) |
| AT (7) | AT266353B (en]) |
| BE (1) | BE652597A (en]) |
| CH (7) | CH476708A (en]) |
| DE (1) | DE1468421A1 (en]) |
| DK (1) | DK123768B (en]) |
| ES (1) | ES314750A1 (en]) |
| FI (1) | FI42438B (en]) |
| FR (2) | FR1481032A (en]) |
| GB (1) | GB1127601A (en]) |
| IL (1) | IL21824A (en]) |
| NL (1) | NL140849B (en]) |
| NO (1) | NO126081B (en]) |
| SE (2) | SE346312B (en]) |
| YU (4) | YU32256B (en]) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239540A (en) * | 1958-06-09 | 1966-03-08 | Upjohn Co | 1-dehydro-6-fluoroprogesterones |
| NL279866A (en]) * | 1961-08-08 |
-
1964
- 1964-06-29 GB GB26744/64A patent/GB1127601A/en not_active Expired
- 1964-08-01 NO NO154249A patent/NO126081B/no unknown
- 1964-08-03 IL IL21824A patent/IL21824A/en unknown
- 1964-08-06 FI FI1691/64A patent/FI42438B/fi active
- 1964-08-17 SE SE16758/68A patent/SE346312B/xx unknown
- 1964-08-17 SE SE09921/64A patent/SE332981B/xx unknown
- 1964-08-29 DK DK428464AA patent/DK123768B/da unknown
- 1964-09-02 BE BE652597D patent/BE652597A/fr unknown
- 1964-09-17 NL NL646410810A patent/NL140849B/xx not_active IP Right Cessation
- 1964-09-18 FR FR988630A patent/FR1481032A/fr not_active Expired
- 1964-09-23 CH CH1333768A patent/CH476708A/de not_active IP Right Cessation
- 1964-09-23 CH CH1334068A patent/CH476714A/de not_active IP Right Cessation
- 1964-09-23 CH CH1233564A patent/CH486437A/de not_active IP Right Cessation
- 1964-09-23 CH CH1333668A patent/CH478112A/de not_active IP Right Cessation
- 1964-09-23 CH CH1333568A patent/CH480320A/de not_active IP Right Cessation
- 1964-09-23 CH CH1333968A patent/CH476705A/de not_active IP Right Cessation
- 1964-09-23 CH CH1333868A patent/CH476713A/de not_active IP Right Cessation
- 1964-09-29 DE DE1964N0025595 patent/DE1468421A1/de active Granted
- 1964-09-29 AT AT275267A patent/AT266353B/de active
- 1964-09-29 AT AT275367A patent/AT266354B/de active
- 1964-09-29 AT AT275467A patent/AT268563B/de active
- 1964-09-29 AT AT275067A patent/AT266351B/de active
- 1964-09-29 AT AT831264A patent/AT270886B/de active
- 1964-09-29 AT AT275167A patent/AT266352B/de active
- 1964-09-29 AT AT275567A patent/AT266355B/de active
-
1965
- 1965-06-28 ES ES0314750A patent/ES314750A1/es not_active Expired
- 1965-06-29 FR FR22813A patent/FR4697M/fr not_active Expired
-
1966
- 1966-10-07 US US585720A patent/US3422122A/en not_active Expired - Lifetime
-
1968
- 1968-01-22 YU YU0150/68A patent/YU32256B/xx unknown
- 1968-01-22 YU YU0154/68A patent/YU31939B/xx unknown
- 1968-01-22 YU YU0148/68A patent/YU31938B/xx unknown
- 1968-01-22 YU YU149/68A patent/YU33973B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT266354B (de) | 1968-11-11 |
| AT266353B (de) | 1968-11-11 |
| NO126081B (en]) | 1972-12-18 |
| IL21824A (en) | 1968-10-24 |
| CH478112A (de) | 1969-09-15 |
| YU31939B (en) | 1974-02-28 |
| AT268563B (de) | 1969-02-10 |
| AT266351B (de) | 1968-11-11 |
| GB1127601A (en) | 1968-09-18 |
| NL6410810A (en]) | 1965-12-30 |
| DK123768B (da) | 1972-07-31 |
| YU15068A (en) | 1973-12-31 |
| YU33973B (en) | 1978-09-08 |
| BE652597A (en]) | 1965-03-02 |
| AT266352B (de) | 1968-11-11 |
| YU32256B (en) | 1974-06-30 |
| FI42438B (en]) | 1970-04-30 |
| YU15468A (en) | 1973-08-31 |
| NL140849B (nl) | 1974-01-15 |
| CH476714A (de) | 1969-08-15 |
| YU14868A (en) | 1973-08-31 |
| ES314750A1 (es) | 1966-02-01 |
| US3422122A (en) | 1969-01-14 |
| YU14968A (en) | 1978-02-28 |
| CH476705A (de) | 1969-08-15 |
| SE346312B (en]) | 1972-07-03 |
| YU31938B (en) | 1974-02-28 |
| CH476713A (de) | 1969-08-15 |
| CH486437A (de) | 1970-02-28 |
| AT270886B (de) | 1969-05-12 |
| FR1481032A (fr) | 1967-05-19 |
| AT266355B (de) | 1968-11-11 |
| SE332981B (en]) | 1971-03-01 |
| FR4697M (en]) | 1967-01-30 |
| DE1468421A1 (de) | 1969-01-02 |
| CH480320A (de) | 1969-10-31 |
Similar Documents
| Publication | Publication Date | Title |
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