SE434268B - Sett att framstella nya oximderivat av 3-tiadiazolyl-tiometyl-7-aminotiazolyl-acetamidocefalosporansyra - Google Patents
Sett att framstella nya oximderivat av 3-tiadiazolyl-tiometyl-7-aminotiazolyl-acetamidocefalosporansyraInfo
- Publication number
- SE434268B SE434268B SE7800790A SE7800790A SE434268B SE 434268 B SE434268 B SE 434268B SE 7800790 A SE7800790 A SE 7800790A SE 7800790 A SE7800790 A SE 7800790A SE 434268 B SE434268 B SE 434268B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- compound
- acid
- group
- methyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 28
- 150000002923 oximes Chemical class 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 89
- -1 3-methyl-1,2,4-thiadiazol-5-yl Chemical group 0.000 claims description 33
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052749 magnesium Inorganic materials 0.000 claims description 12
- 239000011777 magnesium Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
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- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 4
- 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 claims description 3
- 125000004436 sodium atom Chemical group 0.000 claims description 2
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 101150009274 nhr-1 gene Proteins 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
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- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 12
- 159000000000 sodium salts Chemical class 0.000 description 11
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 3
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- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
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- 229910000071 diazene Inorganic materials 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- POBMBNPEUPDXRS-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOC(=O)C(=NOC)C1=CSC(N)=N1 POBMBNPEUPDXRS-UHFFFAOYSA-N 0.000 description 1
- HZUYVNWQSAISMN-UHFFFAOYSA-N ethyl 2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=NOC)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 HZUYVNWQSAISMN-UHFFFAOYSA-N 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000012264 purified product Substances 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BLFQGGGGFNSJKA-XHXSRVRCSA-N sertraline hydrochloride Chemical group Cl.C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 BLFQGGGGFNSJKA-XHXSRVRCSA-N 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7704745A FR2381053A1 (fr) | 1977-02-18 | 1977-02-18 | Nouvelles oximes derivees de l'acide 3-thiadiazolyl thiomethyl 7-aminothiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7800790L SE7800790L (sv) | 1978-08-19 |
| SE434268B true SE434268B (sv) | 1984-07-16 |
Family
ID=9186946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7800790A SE434268B (sv) | 1977-02-18 | 1978-01-23 | Sett att framstella nya oximderivat av 3-tiadiazolyl-tiometyl-7-aminotiazolyl-acetamidocefalosporansyra |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS53108996A (de) |
| AT (1) | AT355722B (de) |
| AU (1) | AU516076B2 (de) |
| BE (1) | BE864074A (de) |
| CA (1) | CA1132537A (de) |
| CH (1) | CH633016A5 (de) |
| DE (1) | DE2806226A1 (de) |
| DK (1) | DK68978A (de) |
| ES (2) | ES467090A1 (de) |
| FI (1) | FI69468C (de) |
| FR (1) | FR2381053A1 (de) |
| GB (1) | GB1575180A (de) |
| GR (1) | GR71703B (de) |
| HU (1) | HU181961B (de) |
| IE (1) | IE46651B1 (de) |
| IL (1) | IL54043A (de) |
| LU (1) | LU79080A1 (de) |
| NL (1) | NL7801834A (de) |
| PT (1) | PT67673B (de) |
| SE (1) | SE434268B (de) |
| SU (1) | SU841590A3 (de) |
| YU (1) | YU41583B (de) |
| ZA (1) | ZA78847B (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE878433A (fr) * | 1978-08-31 | 1980-02-25 | Fujisawa Pharmaceutical Co | Procede de preparation de derives d'acide 3-cephem-4-carboxylique 3,7-disubstitue, nouveaux produits ainsi obtenus et leur utilisation pour leur activite antibacterienne |
| BE878514A (fr) * | 1978-09-04 | 1980-02-29 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3-cephem-4-carboxylique a disubstitution en positions 3 et 7, nouveaux produits ainsi obtenus et leur utilisation pour leur activite antibacterienne |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| US4341775A (en) * | 1978-09-11 | 1982-07-27 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| DE2945248A1 (de) * | 1978-11-13 | 1980-05-22 | Fujisawa Pharmaceutical Co | Cephem-verbindungen, verfahren zu ihrer herstellung und sie enthaltende antibakterielle pharmazeutische mittel |
| CH642957A5 (de) | 1980-02-18 | 1984-05-15 | Lonza Ag | Verfahren zur herstellung von (2-aminothiazol-4-yl)-essigsaeure-hydrochlorid. |
| US4399132A (en) * | 1980-08-11 | 1983-08-16 | American Cyanamid Company | 7-Beta-[alpha-syn-methoxyimino-alpha-(2-aminothiazol-4-yl)-acetamido]-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-3-cephem-4-carboxylic acid and C1 -C6 alkyl derivatives thereof |
| US4761409A (en) * | 1984-08-16 | 1988-08-02 | Sumitomo Pharmaceuticals Company, Limited | Cephem derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| DK162391C (da) * | 1976-04-12 | 1992-03-09 | Fujisawa Pharmaceutical Co | Analogifremgangsmaade til fremstilling af syn-isomerer af 3,7-disubstituerede 3-cephem-4-carboxylsyreforbindelser |
| DE2760484C2 (de) * | 1976-04-14 | 1992-12-03 | Takeda Chemical Industries, Ltd., Osaka, Jp |
-
1977
- 1977-02-18 FR FR7704745A patent/FR2381053A1/fr active Granted
-
1978
- 1978-01-23 SE SE7800790A patent/SE434268B/sv not_active IP Right Cessation
- 1978-02-10 FI FI780444A patent/FI69468C/fi not_active IP Right Cessation
- 1978-02-13 IL IL54043A patent/IL54043A/xx unknown
- 1978-02-13 ZA ZA00780847A patent/ZA78847B/xx unknown
- 1978-02-14 YU YU336/78A patent/YU41583B/xx unknown
- 1978-02-14 DE DE19782806226 patent/DE2806226A1/de not_active Withdrawn
- 1978-02-14 SU SU782578251A patent/SU841590A3/ru active
- 1978-02-16 DK DK68978A patent/DK68978A/da not_active Application Discontinuation
- 1978-02-16 GR GR55474A patent/GR71703B/el unknown
- 1978-02-17 BE BE185267A patent/BE864074A/xx not_active IP Right Cessation
- 1978-02-17 ES ES467090A patent/ES467090A1/es not_active Expired
- 1978-02-17 LU LU79080A patent/LU79080A1/xx unknown
- 1978-02-17 HU HU78RO963A patent/HU181961B/hu unknown
- 1978-02-17 JP JP1666578A patent/JPS53108996A/ja active Pending
- 1978-02-17 NL NL7801834A patent/NL7801834A/xx not_active Application Discontinuation
- 1978-02-17 PT PT67673A patent/PT67673B/pt unknown
- 1978-02-17 AU AU33375/78A patent/AU516076B2/en not_active Expired
- 1978-02-17 CH CH178978A patent/CH633016A5/fr not_active IP Right Cessation
- 1978-02-17 CA CA297,248A patent/CA1132537A/fr not_active Expired
- 1978-02-20 AT AT120978A patent/AT355722B/de not_active IP Right Cessation
- 1978-02-20 IE IE364/78A patent/IE46651B1/en unknown
- 1978-02-20 GB GB6621/78A patent/GB1575180A/en not_active Expired
- 1978-12-13 ES ES475956A patent/ES475956A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI69468C (fi) | 1986-02-10 |
| BE864074A (fr) | 1978-08-17 |
| PT67673A (fr) | 1978-03-01 |
| PT67673B (fr) | 1980-03-03 |
| DE2806226A1 (de) | 1978-08-24 |
| IL54043A0 (en) | 1978-04-30 |
| SE7800790L (sv) | 1978-08-19 |
| CH633016A5 (en) | 1982-11-15 |
| YU41583B (en) | 1987-10-31 |
| GB1575180A (en) | 1980-09-17 |
| HU181961B (en) | 1983-11-28 |
| ZA78847B (en) | 1979-03-28 |
| ATA120978A (de) | 1979-08-15 |
| FR2381053B1 (de) | 1979-06-01 |
| AT355722B (de) | 1980-03-25 |
| JPS53108996A (en) | 1978-09-22 |
| FR2381053A1 (fr) | 1978-09-15 |
| YU33678A (en) | 1983-01-21 |
| GR71703B (de) | 1983-06-21 |
| IE780364L (en) | 1978-08-18 |
| IE46651B1 (en) | 1983-08-10 |
| AU516076B2 (en) | 1981-05-14 |
| LU79080A1 (fr) | 1978-09-28 |
| AU3337578A (en) | 1979-08-23 |
| FI780444A7 (fi) | 1978-08-19 |
| CA1132537A (fr) | 1982-09-28 |
| ES475956A1 (es) | 1979-12-16 |
| ES467090A1 (es) | 1979-06-01 |
| NL7801834A (nl) | 1978-08-22 |
| IL54043A (en) | 1983-02-23 |
| SU841590A3 (ru) | 1981-06-23 |
| FI69468B (fi) | 1985-10-31 |
| DK68978A (da) | 1978-08-19 |
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| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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