DE2526981C3 - lalpha^4-Dihyaroxycholecalciferol-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel - Google Patents
lalpha^4-Dihyaroxycholecalciferol-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische MittelInfo
- Publication number
- DE2526981C3 DE2526981C3 DE752526981A DE2526981A DE2526981C3 DE 2526981 C3 DE2526981 C3 DE 2526981C3 DE 752526981 A DE752526981 A DE 752526981A DE 2526981 A DE2526981 A DE 2526981A DE 2526981 C3 DE2526981 C3 DE 2526981C3
- Authority
- DE
- Germany
- Prior art keywords
- diene
- formula
- derivative
- hydrogen atom
- dhcc
- 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
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- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- DTGDZMYNKLTSKC-HKQCOZBKSA-N cholest-5-ene Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 DTGDZMYNKLTSKC-HKQCOZBKSA-N 0.000 description 1
- DTGDZMYNKLTSKC-UHFFFAOYSA-N cholest-5-ene Natural products C1C=C2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 DTGDZMYNKLTSKC-UHFFFAOYSA-N 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000004821 effect on bone Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000007904 elastic gelatin capsule Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000020189 fortified milk Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000012902 gut sac method Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000011507 gypsum plaster Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 208000011111 hypophosphatemic rickets Diseases 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000007903 liver failure Diseases 0.000 description 1
- 231100000835 liver failure Toxicity 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000849 parathyroid Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- YUGCAAVRZWBXEQ-WHTXLNIXSA-N previtamin D3 Chemical compound C=1([C@@H]2CC[C@@H]([C@]2(CCC=1)C)[C@H](C)CCCC(C)C)\C=C/C1=C(C)CC[C@H](O)C1 YUGCAAVRZWBXEQ-WHTXLNIXSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 201000006409 renal osteodystrophy Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000001162 steatorrhea Diseases 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000003826 tablet 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
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000005039 triarylmethyl group Chemical group 0.000 description 1
- 208000032349 type 2B vitamin D-dependent rickets Diseases 0.000 description 1
- 229950009811 ubenimex Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 208000030402 vitamin D-dependent rickets Diseases 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/174—Vitamins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6866474A JPS539222B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-18 | 1974-06-18 | |
| JP14133074A JPS5168557A (en) | 1974-12-09 | 1974-12-09 | 1 arufua 244 jihidorokishikorekarushifuerooruno seizoho |
| JP49141332A JPS5168560A (en) | 1974-12-09 | 1974-12-09 | 1 arufua 244 jihidorokishikorekarushifuerooruno bunriho |
| JP14133174A JPS5320989B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-12-09 | 1974-12-09 | |
| JP14132974A JPS5168556A (en) | 1974-12-09 | 1974-12-09 | 1 arufua 244 jihidorokishikorekarushifuerooruno seizohoho |
| JP14902174A JPS5176255A (en) | 1974-12-27 | 1974-12-27 | 1 arufua * 24 * s * jihidorokishikorekarushifueroorunoseizohoho |
| JP14901774A JPS5176252A (en) | 1974-12-27 | 1974-12-27 | 1 arufua *24 * r * jihidorokishikorekarushifueroorunoseizoho |
| JP14902274A JPS5176259A (en) | 1974-12-27 | 1974-12-27 | 244 benzoiruokishikoresuteroorujudotaino 24 iepimaanobunriho |
| JP14902074A JPS5176254A (en) | 1974-12-27 | 1974-12-27 | 1 arufua * 24 * s * jihidorokishikorekarushifueroorunoseizoho |
| JP14901874A JPS5176253A (en) | 1974-12-27 | 1974-12-27 | 1 arufua *24 * r * jihidorokishikorekarushifueroorunoseizohoho |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2526981A1 DE2526981A1 (de) | 1976-01-15 |
| DE2526981B2 DE2526981B2 (de) | 1978-06-29 |
| DE2526981C3 true DE2526981C3 (de) | 1979-03-01 |
Family
ID=27580092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE752526981A Expired DE2526981C3 (de) | 1974-06-18 | 1975-06-18 | lalpha^4-Dihyaroxycholecalciferol-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel |
Country Status (10)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1088094B (it) * | 1976-10-14 | 1985-06-04 | Hoffmann La Roche | Derivati del pregnano |
| JPS53147051A (en) * | 1977-05-24 | 1978-12-21 | Teijin Ltd | 1alpha-hydroxy-24-dehydro-vitamin d3 and its preparation |
| JPS5822479B2 (ja) * | 1977-09-07 | 1983-05-09 | 帝人株式会社 | １α−ヒドロキシ−２４−オキソ−ビタミンＤ↓３およびその製造法 |
| US4225596A (en) * | 1978-10-13 | 1980-09-30 | Wisconsin Alumni Research Foundation | Method for treating calcium imbalance and improving calcium absorption in mammals |
| LU80545A1 (de) * | 1978-11-17 | 1980-06-05 | Hoffmann La Roche | Verfahren zur herstellung von 1a,3s-dihydroxy->5-steroiden |
| US4230701A (en) * | 1979-03-21 | 1980-10-28 | Hoffmann-La Roche Inc. | Administration of biologically active vitamin D3 and vitamin D2 materials |
| US4335120A (en) * | 1979-03-21 | 1982-06-15 | Hoffmann-La Roche Inc. | Administration of biologically active vitamin D3 and vitamin D2 materials |
| JPS55136229A (en) * | 1979-04-10 | 1980-10-23 | Teijin Ltd | Adjustment of bone metabolism in warm-blooded animal and drug for it |
| JPS5626820A (en) * | 1979-08-10 | 1981-03-16 | Chugai Pharmaceut Co Ltd | Immunosuppressing agent |
| US4338250A (en) * | 1981-04-27 | 1982-07-06 | Wisconsin Alumni Research Foundation | 1-Hydroxylation process |
| CA1272953A (en) | 1984-10-08 | 1990-08-21 | Yuji Makino | Pharmaceutical composition for external use containing active-type vitamin d.sub.3 |
| JPH0749435B2 (ja) * | 1988-07-04 | 1995-05-31 | 帝人株式会社 | １α，３β，２４−トリヒドロキシ−△▲上５▼−ステロイド類の製造方法 |
| US5532228A (en) * | 1990-02-06 | 1996-07-02 | Schering Aktiengesellschaft | Side-chain homologous vitamin D derivatives, process for their production, pharmaceutical preparations containing these derivatives and their use as pharmaceutical agents |
| WO1992012165A1 (en) | 1991-01-08 | 1992-07-23 | Lunar Corporation | METHODS FOR PREPARATION AND USE OF 1α,24-DIHYDROXY VITAMIN D¿2? |
| US5786348A (en) * | 1991-01-08 | 1998-07-28 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-dihydroxy vitamin D2 |
| US6166000A (en) * | 1991-01-08 | 2000-12-26 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-Dihydroxy vitamin . D.sub2 |
| US6538037B2 (en) | 1991-01-08 | 2003-03-25 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-dihydroxyvitamin D2 |
| US20040009958A1 (en) * | 1991-01-08 | 2004-01-15 | Bone Care International, Inc. | Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2 |
| US6251883B1 (en) | 1991-01-08 | 2001-06-26 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-dihydroxy vitamin D2 |
| ES2134267T3 (es) * | 1992-08-28 | 1999-10-01 | Bone Care Int Inc | 1alfa,24(s)-dihidroxi vitamina d2, su preparacion y utilizacion. |
| IL107185A (en) * | 1992-10-06 | 1998-02-22 | Schering Ag | Vitamin d, 25-carboxylic acid derivatives and pharmaceutical compositions containing the same |
| US5869472A (en) * | 1994-07-18 | 1999-02-09 | Bone Care International, Inc. | Synthesis of 1α-hydroxy vitamin D |
| US6362350B1 (en) | 1999-07-01 | 2002-03-26 | Wisconsin Alumni Research Foundation | Crystalline 1α, 24(S)-dihydroxyvitamin D2 and method of purification thereof |
| US7129230B2 (en) | 2001-03-12 | 2006-10-31 | Nestec S.A. | Method and product for treating cancer in pets |
| US20060003950A1 (en) * | 2004-06-30 | 2006-01-05 | Bone Care International, Inc. | Method of treating prostatic diseases using a combination of vitamin D analogues and other agents |
| US7094775B2 (en) * | 2004-06-30 | 2006-08-22 | Bone Care International, Llc | Method of treating breast cancer using a combination of vitamin D analogues and other agents |
| TW200714580A (en) * | 2005-10-14 | 2007-04-16 | Formosa Lab Inc | Process for preparing vitamin D analogs |
| CN101998949B (zh) * | 2008-03-12 | 2015-11-25 | 赛特克罗公司 | 稳定化的1，25-二羟基维生素d2和其制备方法 |
| KR102300311B1 (ko) | 2017-04-18 | 2021-09-10 | 연성정밀화학(주) | 타칼시톨의 제조방법 및 그를 위한 중간체 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3901928A (en) * | 1973-01-10 | 1975-08-26 | Robert Henry Hesse | 1' ,3' -dihydroxy steroid-5-enes method of preparing same and their use for preparing 1' -hydroxy-25-hydrogen vitamin d compounds |
| US3928397A (en) * | 1973-03-02 | 1975-12-23 | Eisai Co Ltd | New 5-cholestene derivatives and preparation thereof |
-
1975
- 1975-06-02 US US05/583,115 patent/US4022891A/en not_active Expired - Lifetime
- 1975-06-04 GB GB24138/75A patent/GB1508042A/en not_active Expired
- 1975-06-04 GB GB44013/76A patent/GB1508043A/en not_active Expired
- 1975-06-09 SE SE7506560A patent/SE413096B/xx not_active IP Right Cessation
- 1975-06-17 CA CA229,466A patent/CA1051442A/en not_active Expired
- 1975-06-17 DK DK273375AA patent/DK142410B/da not_active IP Right Cessation
- 1975-06-17 NO NO752150A patent/NO145162C/no unknown
- 1975-06-18 NL NL7507268A patent/NL7507268A/xx unknown
- 1975-06-18 DE DE752526981A patent/DE2526981C3/de not_active Expired
- 1975-06-18 CH CH793875A patent/CH618669A5/de not_active IP Right Cessation
- 1975-06-18 FR FR7519074A patent/FR2275196A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1508042A (en) | 1978-04-19 |
| CA1051442A (en) | 1979-03-27 |
| DE2526981B2 (de) | 1978-06-29 |
| NL7507268A (nl) | 1975-12-22 |
| GB1508043A (en) | 1978-04-19 |
| FR2275196A1 (fr) | 1976-01-16 |
| NO145162C (no) | 1982-01-27 |
| DK273375A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-19 |
| DE2526981A1 (de) | 1976-01-15 |
| FR2275196B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-06 |
| US4022891A (en) | 1977-05-10 |
| NO145162B (no) | 1981-10-19 |
| SE7506560L (sv) | 1975-12-19 |
| CH618669A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-08-15 |
| NO752150L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-19 |
| DK142410B (da) | 1980-10-27 |
| SE413096B (sv) | 1980-04-14 |
| DK142410C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-03-23 |
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