JPS5829320B2 - スピロラクトンステロイド ノ シンキナ セイゾウホウ - Google Patents
スピロラクトンステロイド ノ シンキナ セイゾウホウInfo
- Publication number
- JPS5829320B2 JPS5829320B2 JP49014627A JP1462774A JPS5829320B2 JP S5829320 B2 JPS5829320 B2 JP S5829320B2 JP 49014627 A JP49014627 A JP 49014627A JP 1462774 A JP1462774 A JP 1462774A JP S5829320 B2 JPS5829320 B2 JP S5829320B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- product
- compound
- following general
- alkyl group
- 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
- -1 Spirolactone steroid Chemical class 0.000 title description 11
- 229960002256 spironolactone Drugs 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 9
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 230000020477 pH reduction Effects 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 12
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical group 0.000 claims 2
- 239000000047 product Substances 0.000 description 91
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 125000003003 spiro group Chemical group 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000004364 calculation method Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000002609 medium Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000002211 ultraviolet spectrum Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005035 acylthio group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 2
- FUKMJJIEEBZZJC-DFXIMRFUSA-N 3-[(8s,9s,10r,13r,14s,17r)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]propanoic acid Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)CCC(O)=O)[C@@H]4[C@@H]3CCC2=C1 FUKMJJIEEBZZJC-DFXIMRFUSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000457 gamma-lactone group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- SYIOZFGXQZYCAW-HIIHSHPDSA-N 3-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-hydroxypropanoic acid Chemical compound OC(C[C@H]1CC[C@H]2[C@@H]3CCC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O)C(=O)O SYIOZFGXQZYCAW-HIIHSHPDSA-N 0.000 description 1
- CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 229930186657 Lat Natural products 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- DAKOBUIKDCTJEB-UHFFFAOYSA-L disodium;propanoate Chemical compound [Na+].[Na+].CCC([O-])=O.CCC([O-])=O DAKOBUIKDCTJEB-UHFFFAOYSA-L 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000003637 steroidlike Effects 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7304057A FR2216273B1 (enExample) | 1973-02-06 | 1973-02-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS49109365A JPS49109365A (enExample) | 1974-10-17 |
| JPS5829320B2 true JPS5829320B2 (ja) | 1983-06-22 |
Family
ID=9114388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49014627A Expired JPS5829320B2 (ja) | 1973-02-06 | 1974-02-06 | スピロラクトンステロイド ノ シンキナ セイゾウホウ |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3897417A (enExample) |
| JP (1) | JPS5829320B2 (enExample) |
| AT (1) | AT336811B (enExample) |
| BE (1) | BE810643A (enExample) |
| CA (1) | CA1026318A (enExample) |
| CH (2) | CH609710A5 (enExample) |
| DK (1) | DK134818B (enExample) |
| ES (2) | ES422921A1 (enExample) |
| FR (1) | FR2216273B1 (enExample) |
| GB (1) | GB1451843A (enExample) |
| IE (1) | IE39329B1 (enExample) |
| LU (1) | LU69328A1 (enExample) |
| NL (1) | NL179288C (enExample) |
| SE (2) | SE399270B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4058522A (en) * | 1973-07-09 | 1977-11-15 | Richter Gedeon Vegyeszeti Gyar Rt. | Steroids effective against heavy-metal poisoning |
| IT1130924B (it) * | 1980-03-06 | 1986-06-18 | Secifarma Spa | Procedimento per la preparazione di spironolattone micronizzato |
| US4501695A (en) * | 1983-05-16 | 1985-02-26 | The Upjohn Company | Spironalactone process |
| DK0973791T3 (da) * | 1995-12-11 | 2007-09-17 | Searle Llc | Fremgangsmåde til fremstilling af en epoxyforbindelse |
| US6887991B1 (en) | 1996-12-11 | 2005-05-03 | G. D. Searle & Company | Processes for preparation of 9, 11-epoxy steroids and intermediates useful therein |
| NZ336004A (en) | 1996-12-11 | 2001-04-27 | G | Process for preparation of 3-keto-7-alpha-alkoxycarbonyl substituted delta-4,5-steroid by reacting 4,5-dihydro-5,7-lactone steroid substrate in the presence of a base |
| RU2163606C1 (ru) * | 1999-12-08 | 2001-02-27 | Андрюшина Валентина Александровна | СПОСОБ ПОЛУЧЕНИЯ γ-ЛАКТОНА 3(7α-АЦЕТИЛТИО-17β-ГИДРОКСИ-3-ОКСОАНДРОСТ-4-ЕН-17α-ИЛ)ПРОПИОНОВОЙ КИСЛОТЫ |
| KR20050028907A (ko) * | 2002-03-22 | 2005-03-23 | 파마시아 코포레이션 | 스테로이드의 ｃ-17 스피롤락톤화 및 6,7 산화 |
| US7235655B2 (en) * | 2002-03-22 | 2007-06-26 | Pharmacia & Upjohn Company | Processes to prepare eplerenone |
| DE102005049393B4 (de) * | 2005-10-15 | 2019-08-08 | Kennametal Widia Produktions Gmbh & Co. Kg | Verfahren zur Herstellung eines beschichteten Substratkörpers, Substratkörper mit einer Beschichtung und Verwendung des beschichteten Substratkörpers |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1329570A (fr) * | 1959-12-10 | 1963-06-14 | Searle & Co | Procédé de préparation des lactones d'alcanoylthio-17alpha-carboxyéthyl-17bêta-hydroxy-3-oxoandrostènes |
| US3257390A (en) * | 1963-06-12 | 1966-06-21 | Merck & Co Inc | Ring a unsaturated 21-hydroxy-3-oxo-17alpha-pregnane-17-carboxylic acid lactone diuretic agents |
| US3300489A (en) * | 1964-07-24 | 1967-01-24 | Smith Kline French Lab | Steroidal c-17 spirolactones and processes and intermediates used in the preparation thereof |
-
1973
- 1973-02-06 FR FR7304057A patent/FR2216273B1/fr not_active Expired
-
1974
- 1974-02-01 US US438601A patent/US3897417A/en not_active Expired - Lifetime
- 1974-02-05 BE BE140580A patent/BE810643A/xx unknown
- 1974-02-05 ES ES422921A patent/ES422921A1/es not_active Expired
- 1974-02-05 CH CH385975A patent/CH609710A5/xx not_active IP Right Cessation
- 1974-02-05 CA CA191,844A patent/CA1026318A/en not_active Expired
- 1974-02-05 LU LU69328A patent/LU69328A1/xx unknown
- 1974-02-05 SE SE7401494A patent/SE399270B/xx not_active IP Right Cessation
- 1974-02-05 CH CH158474A patent/CH595399A5/xx not_active IP Right Cessation
- 1974-02-06 JP JP49014627A patent/JPS5829320B2/ja not_active Expired
- 1974-02-06 DK DK62574AA patent/DK134818B/da not_active IP Right Cessation
- 1974-02-06 AT AT92174A patent/AT336811B/de not_active IP Right Cessation
- 1974-02-06 NL NLAANVRAGE7401656,A patent/NL179288C/xx not_active IP Right Cessation
- 1974-02-06 IE IE226/74A patent/IE39329B1/xx unknown
- 1974-02-06 GB GB545174A patent/GB1451843A/en not_active Expired
-
1976
- 1976-01-07 ES ES444112A patent/ES444112A1/es not_active Expired
-
1977
- 1977-06-03 SE SE7706509A patent/SE440782B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH609710A5 (enExample) | 1979-03-15 |
| IE39329L (en) | 1974-08-06 |
| FR2216273A1 (enExample) | 1974-08-30 |
| CH595399A5 (enExample) | 1978-02-15 |
| ATA92174A (de) | 1976-09-15 |
| ES422921A1 (es) | 1976-09-16 |
| LU69328A1 (enExample) | 1974-09-25 |
| ES444112A1 (es) | 1977-08-16 |
| DK134818B (da) | 1977-01-24 |
| NL179288C (nl) | 1986-08-18 |
| IE39329B1 (en) | 1978-09-13 |
| US3897417A (en) | 1975-07-29 |
| DK134818C (enExample) | 1977-06-13 |
| CA1026318A (en) | 1978-02-14 |
| GB1451843A (en) | 1976-10-06 |
| AU6521174A (en) | 1975-08-07 |
| SE440782B (sv) | 1985-08-19 |
| BE810643A (fr) | 1974-08-05 |
| SE7706509L (sv) | 1977-06-03 |
| FR2216273B1 (enExample) | 1977-07-22 |
| JPS49109365A (enExample) | 1974-10-17 |
| NL179288B (nl) | 1986-03-17 |
| SE399270B (sv) | 1978-02-06 |
| NL7401656A (enExample) | 1974-08-08 |
| AT336811B (de) | 1977-05-25 |
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