CS203193B2 - Method of producing n 1-glucofuranosid-6-yl-n 3-nitrosoureas - Google Patents
Method of producing n 1-glucofuranosid-6-yl-n 3-nitrosoureas Download PDFInfo
- Publication number
- CS203193B2 CS203193B2 CS783897A CS389778A CS203193B2 CS 203193 B2 CS203193 B2 CS 203193B2 CS 783897 A CS783897 A CS 783897A CS 389778 A CS389778 A CS 389778A CS 203193 B2 CS203193 B2 CS 203193B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- ethyl
- hydrogen
- acid
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- -1 straight or branched Chemical group 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 208000032839 leukemia Diseases 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 238000000576 coating method Methods 0.000 description 4
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- 239000012362 glacial acetic acid Substances 0.000 description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AVVWPBAENSWJCB-IVMDWMLBSA-N D-glucofuranose Chemical class OC[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O AVVWPBAENSWJCB-IVMDWMLBSA-N 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
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- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
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- CNFITXRNLNVOAR-ILAIQSSSSA-N 1-[(2R)-2-[(2R,3R,4R,5S)-5-ethoxy-4-hydroxy-3-methoxyoxolan-2-yl]-2-methoxyethyl]-3-methylurea Chemical compound CCO[C@H]1O[C@H]([C@@H](CNC(=O)NC)OC)[C@H](OC)[C@H]1O CNFITXRNLNVOAR-ILAIQSSSSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
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- OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical class NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 1
- ZAOCWQZQPKGTRN-UHFFFAOYSA-N nitrous acid;sodium Chemical class [Na].ON=O ZAOCWQZQPKGTRN-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
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 150000008504 β-D-glucofuranosides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS793337A CS203194B2 (cs) | 1977-06-15 | 1979-05-15 | Způsob výroby Ni-glukofuranosid-6-yl-N3-nitrosomočovin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH735977 | 1977-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203193B2 true CS203193B2 (en) | 1981-02-27 |
Family
ID=4323894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS783897A CS203193B2 (en) | 1977-06-15 | 1978-06-14 | Method of producing n 1-glucofuranosid-6-yl-n 3-nitrosoureas |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4273766A (el) |
| EP (1) | EP0000126B1 (el) |
| JP (1) | JPS545909A (el) |
| AR (2) | AR221845A1 (el) |
| AT (1) | AT358601B (el) |
| AU (1) | AU517665B2 (el) |
| CA (1) | CA1096859A (el) |
| CS (1) | CS203193B2 (el) |
| CY (1) | CY1263A (el) |
| DD (1) | DD137360A5 (el) |
| DE (1) | DE2862098D1 (el) |
| DK (1) | DK267078A (el) |
| ES (1) | ES470738A1 (el) |
| FI (1) | FI65781C (el) |
| GR (1) | GR73054B (el) |
| HK (1) | HK2285A (el) |
| HU (1) | HU179686B (el) |
| IE (1) | IE47090B1 (el) |
| IL (1) | IL54909A (el) |
| MY (1) | MY8700029A (el) |
| NO (1) | NO145843C (el) |
| NZ (1) | NZ187571A (el) |
| PL (2) | PL112747B1 (el) |
| PT (1) | PT68164A (el) |
| SG (1) | SG44284G (el) |
| SU (2) | SU910118A3 (el) |
| ZA (1) | ZA783430B (el) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2961524D1 (en) * | 1978-02-21 | 1982-02-04 | Ciba Geigy Ag | Glycofuranosyl-nitrosourea derivatives, process for their manufacture and their pharmaceutical preparations |
| FR2487343A1 (fr) * | 1980-07-25 | 1982-01-29 | Anvar | Nouveaux nitroso-carbamates, procede pour leur preparation et application a la synthese selective de n-nitrosourees |
| JPS57165398A (en) * | 1981-04-02 | 1982-10-12 | Tanabe Seiyaku Co Ltd | Nitrosourea derivative and its preparation |
| JPS57200397A (en) * | 1981-06-03 | 1982-12-08 | Akira Kimura | Novel aldohexopyranose-, aldopentopyranose-, or and medicament composition comprising it aldopentofuranose- nitrosourea compound, its preparation |
| US4902791A (en) * | 1983-08-30 | 1990-02-20 | Sanofi S.A. | Nitrosourea derivatives, process for their preparation and medicaments containing them |
| US4613590A (en) * | 1985-08-19 | 1986-09-23 | Abbott Laboratories | Amino D-manno-2-octulopyranosidonate containing compounds, pharmaceutical compositions and method of use |
| FR2614304A1 (fr) * | 1987-04-22 | 1988-10-28 | Sanofi Sa | Derives de nitrosourees, leur nouveau procede de preparation et leurs applications therapeutiques. |
| ATE238804T1 (de) * | 1993-06-11 | 2003-05-15 | Boston Life Sciences Inc | Immunomodulierende, entzündungshemmende und antiproliferative verbindungen:5,6-dideoxy, 5- aminoderivate von idose und 6-deoxy, 6- aminoderivate von glukose |
| EP1671620B1 (en) * | 2004-12-17 | 2011-02-16 | Kao Corporation | Makeup composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5230491B2 (el) * | 1974-07-05 | 1977-08-09 | ||
| JPS5126819A (en) * | 1974-08-08 | 1976-03-05 | Tokyo Tanabe Co | Arukiru nn karubamiru n**22 kuroruechiru n** nitoroso dd gurukopiranoshidojudotaino seizoho |
| JPS5126876A (en) * | 1974-08-08 | 1976-03-05 | Suami T | Shinkina nitorosonyosojudotaino seizohoho |
| US3940383A (en) * | 1974-12-12 | 1976-02-24 | Stanford Research Institute | Streptozotocin analogs |
| JPS5175072A (ja) * | 1974-12-18 | 1976-06-29 | Tokyo Tanabe Co | Ribofuranoozunonitorosokarubamirujudotaino seizoho |
-
1978
- 1978-06-05 FI FI781779A patent/FI65781C/fi not_active IP Right Cessation
- 1978-06-07 CY CY1263A patent/CY1263A/xx unknown
- 1978-06-07 DE DE7878100115T patent/DE2862098D1/de not_active Expired
- 1978-06-07 EP EP78100115A patent/EP0000126B1/de not_active Expired
- 1978-06-12 PT PT68164A patent/PT68164A/pt unknown
- 1978-06-13 CA CA305,315A patent/CA1096859A/en not_active Expired
- 1978-06-13 ES ES470738A patent/ES470738A1/es not_active Expired
- 1978-06-14 NO NO782069A patent/NO145843C/no unknown
- 1978-06-14 IE IE1193/78A patent/IE47090B1/en unknown
- 1978-06-14 DK DK267078A patent/DK267078A/da not_active Application Discontinuation
- 1978-06-14 AT AT433378A patent/AT358601B/de not_active IP Right Cessation
- 1978-06-14 GR GR56521A patent/GR73054B/el unknown
- 1978-06-14 SU SU782626797A patent/SU910118A3/ru active
- 1978-06-14 IL IL54909A patent/IL54909A/xx unknown
- 1978-06-14 CS CS783897A patent/CS203193B2/cs unknown
- 1978-06-14 DD DD78206000A patent/DD137360A5/xx unknown
- 1978-06-14 HU HU78CI1835A patent/HU179686B/hu unknown
- 1978-06-14 PL PL1978207625A patent/PL112747B1/pl not_active IP Right Cessation
- 1978-06-14 AU AU37089/78A patent/AU517665B2/en not_active Expired
- 1978-06-14 PL PL1978217114A patent/PL113378B1/pl unknown
- 1978-06-14 ZA ZA00783430A patent/ZA783430B/xx unknown
- 1978-06-14 NZ NZ187571A patent/NZ187571A/xx unknown
- 1978-06-15 JP JP7158978A patent/JPS545909A/ja active Pending
- 1978-06-18 AR AR272607A patent/AR221845A1/es active
-
1979
- 1979-03-12 SU SU792737152A patent/SU917699A3/ru active
- 1979-04-12 US US06/029,495 patent/US4273766A/en not_active Expired - Lifetime
- 1979-11-02 AR AR278757A patent/AR222844A1/es active
-
1984
- 1984-06-18 SG SG442/84A patent/SG44284G/en unknown
-
1985
- 1985-01-10 HK HK22/85A patent/HK2285A/xx unknown
-
1987
- 1987-12-30 MY MY29/87A patent/MY8700029A/xx unknown
Also Published As
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