IL38550A - Noble history of digoxin and process for their production - Google Patents
Noble history of digoxin and process for their productionInfo
- Publication number
- IL38550A IL38550A IL38550A IL3855072A IL38550A IL 38550 A IL38550 A IL 38550A IL 38550 A IL38550 A IL 38550A IL 3855072 A IL3855072 A IL 3855072A IL 38550 A IL38550 A IL 38550A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- acid
- compound
- digoxin
- effected
- Prior art date
Links
- 229960005156 digoxin Drugs 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 41
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 title description 19
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 title description 19
- 238000004519 manufacturing process Methods 0.000 title description 8
- 125000002252 acyl group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 28
- 239000003826 tablet Substances 0.000 claims description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 238000005917 acylation reaction Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000000829 suppository Substances 0.000 claims description 12
- 230000010933 acylation Effects 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000012442 inert solvent Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 5
- 239000006196 drop Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical group 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 239000006188 syrup Substances 0.000 claims description 3
- 235000020357 syrup Nutrition 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 20
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 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 13
- 239000008101 lactose Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 229940085034 digoxin 0.25 mg Drugs 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- -1 phenylacetyl Chemical group 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940085080 digoxin 0.125 mg Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000009090 positive inotropic effect Effects 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
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- 235000019204 saccharin Nutrition 0.000 description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
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- 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 2
- 239000002562 thickening agent Substances 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- KOPMZTKUZCNGFY-UHFFFAOYSA-N 1,1,1-triethoxybutane Chemical compound CCCC(OCC)(OCC)OCC KOPMZTKUZCNGFY-UHFFFAOYSA-N 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- URFKLQSFBXBOQU-UHFFFAOYSA-N 2-chloro-1,1,1-triethoxyethane Chemical compound CCOC(CCl)(OCC)OCC URFKLQSFBXBOQU-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
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- 244000105624 Arachis hypogaea Species 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent 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
- A61K31/075—Ethers or acetals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712101595 DE2101595A1 (de) | 1971-01-14 | 1971-01-14 | Neue Acylderivate des Digoxins und Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL38550A0 IL38550A0 (en) | 1972-03-28 |
| IL38550A true IL38550A (en) | 1974-11-29 |
Family
ID=5795884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38550A IL38550A (en) | 1971-01-14 | 1972-01-13 | Noble history of digoxin and process for their production |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3804825A (forum.php) |
| AT (1) | AT317444B (forum.php) |
| AU (1) | AU465777B2 (forum.php) |
| BE (1) | BE778014A (forum.php) |
| BG (2) | BG18877A3 (forum.php) |
| CA (1) | CA962665A (forum.php) |
| CH (2) | CH571025A5 (forum.php) |
| CS (1) | CS178403B2 (forum.php) |
| DE (1) | DE2101595A1 (forum.php) |
| DK (1) | DK126938B (forum.php) |
| ES (2) | ES398804A1 (forum.php) |
| FI (1) | FI51359C (forum.php) |
| FR (1) | FR2121851B1 (forum.php) |
| GB (1) | GB1371937A (forum.php) |
| HU (1) | HU162743B (forum.php) |
| IE (1) | IE36060B1 (forum.php) |
| IL (1) | IL38550A (forum.php) |
| NL (1) | NL7200446A (forum.php) |
| PH (1) | PH10692A (forum.php) |
| PL (1) | PL82940B1 (forum.php) |
| RO (2) | RO62477A (forum.php) |
| SE (1) | SE379048B (forum.php) |
| SU (1) | SU511015A3 (forum.php) |
| ZA (1) | ZA72241B (forum.php) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987031A (en) * | 1970-12-23 | 1976-10-19 | Boehringer Ingelheim Gmbh | Acyl derivatives of proscillaridin a |
| DE2354119A1 (de) * | 1973-10-29 | 1975-05-15 | Boehringer Sohn Ingelheim | Neue orthoformiatderivate des digitoxins, verfahren zu deren herstellung sowie diese enthaltende arzneimittel |
| US3884905A (en) * | 1974-05-02 | 1975-05-20 | Interx Research Corp | Pro-drug forms of digoxin |
| US4021535A (en) * | 1975-01-14 | 1977-05-03 | Beckman Instruments, Inc. | Reagents used in the radioimmunoassay of digoxin |
| EP1202056A1 (en) * | 2000-10-30 | 2002-05-02 | Vrije Universiteit Amsterdam | Continuous-flow homogeneous bio-chemical assays based on mass spectrometric detection of known ligands |
| CN112552367B (zh) * | 2020-12-11 | 2023-06-06 | 郑州安图生物工程股份有限公司 | 一种地高辛衍生物及其制备方法 |
-
1971
- 1971-01-14 DE DE19712101595 patent/DE2101595A1/de active Pending
-
1972
- 1972-01-03 BG BG022617A patent/BG18877A3/xx unknown
- 1972-01-05 US US00215666A patent/US3804825A/en not_active Expired - Lifetime
- 1972-01-11 BG BG019442A patent/BG18190A3/xx unknown
- 1972-01-12 HU HUBO1345A patent/HU162743B/hu unknown
- 1972-01-12 PH PH13181A patent/PH10692A/en unknown
- 1972-01-12 NL NL7200446A patent/NL7200446A/xx unknown
- 1972-01-12 SE SE7200327A patent/SE379048B/xx unknown
- 1972-01-12 ES ES398804A patent/ES398804A1/es not_active Expired
- 1972-01-13 PL PL1972152879A patent/PL82940B1/pl unknown
- 1972-01-13 FI FI720070A patent/FI51359C/fi active
- 1972-01-13 ZA ZA720241A patent/ZA72241B/xx unknown
- 1972-01-13 GB GB172972A patent/GB1371937A/en not_active Expired
- 1972-01-13 AU AU37868/72A patent/AU465777B2/en not_active Expired
- 1972-01-13 CH CH46072A patent/CH571025A5/xx not_active IP Right Cessation
- 1972-01-13 IL IL38550A patent/IL38550A/en unknown
- 1972-01-13 CS CS230A patent/CS178403B2/cs unknown
- 1972-01-13 CA CA132,333A patent/CA962665A/en not_active Expired
- 1972-01-13 DK DK16872AA patent/DK126938B/da unknown
- 1972-01-13 BE BE778014A patent/BE778014A/xx unknown
- 1972-01-13 CH CH720075A patent/CH575435A5/xx not_active IP Right Cessation
- 1972-01-14 SU SU1737660A patent/SU511015A3/ru active
- 1972-01-14 AT AT32772A patent/AT317444B/de not_active IP Right Cessation
- 1972-01-14 RO RO7200069393A patent/RO62477A/ro unknown
- 1972-01-14 FR FR7201256A patent/FR2121851B1/fr not_active Expired
- 1972-01-14 IE IE55/72A patent/IE36060B1/xx unknown
- 1972-01-14 RO RO7271661A patent/RO68217A/ro unknown
- 1972-04-17 ES ES401836A patent/ES401836A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES398804A1 (es) | 1974-08-16 |
| CH571025A5 (forum.php) | 1975-12-31 |
| CH575435A5 (forum.php) | 1976-05-14 |
| FR2121851A1 (forum.php) | 1972-08-25 |
| CS178403B2 (forum.php) | 1977-09-15 |
| IL38550A0 (en) | 1972-03-28 |
| BG18877A3 (bg) | 1975-03-20 |
| RO68217A (ro) | 1982-02-26 |
| SE379048B (forum.php) | 1975-09-22 |
| BE778014A (fr) | 1972-07-13 |
| PL82940B1 (forum.php) | 1975-10-31 |
| RO62477A (fr) | 1978-03-15 |
| AU3786872A (en) | 1973-07-19 |
| CA962665A (en) | 1975-02-11 |
| ES401836A1 (es) | 1975-03-16 |
| FR2121851B1 (forum.php) | 1975-10-31 |
| HU162743B (forum.php) | 1973-04-28 |
| IE36060B1 (en) | 1976-08-04 |
| DK126938B (da) | 1973-09-03 |
| FI51359C (fi) | 1976-12-10 |
| PH10692A (en) | 1977-08-10 |
| AT317444B (de) | 1974-08-26 |
| GB1371937A (en) | 1974-10-30 |
| NL7200446A (forum.php) | 1972-07-18 |
| BG18190A3 (bg) | 1974-09-02 |
| IE36060L (en) | 1972-07-14 |
| AU465777B2 (en) | 1975-10-09 |
| ZA72241B (en) | 1973-09-26 |
| US3804825A (en) | 1974-04-16 |
| SU511015A3 (ru) | 1976-04-15 |
| FI51359B (forum.php) | 1976-08-31 |
| DE2101595A1 (de) | 1972-07-27 |
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