DK142029B - Analogifremgangsmåde til fremstilling af 5-fluor-hexahydropyrimidin-5-carboxylsyrederivater. - Google Patents
Analogifremgangsmåde til fremstilling af 5-fluor-hexahydropyrimidin-5-carboxylsyrederivater. Download PDFInfo
- Publication number
- DK142029B DK142029B DK141177AA DK141177A DK142029B DK 142029 B DK142029 B DK 142029B DK 141177A A DK141177A A DK 141177AA DK 141177 A DK141177 A DK 141177A DK 142029 B DK142029 B DK 142029B
- Authority
- DK
- Denmark
- Prior art keywords
- fluoro
- dioxopyrimidine
- broad
- fluorine
- carboxylate
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
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- 238000002512 chemotherapy Methods 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- ONPSRCNNSZSSMH-UHFFFAOYSA-N chloroform;hexane;methanol Chemical compound OC.ClC(Cl)Cl.CCCCCC ONPSRCNNSZSSMH-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000431 effect on proliferation Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 239000010436 fluorite Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ZCWVHOWKQQGEPP-UHFFFAOYSA-N methyl 2,4-dioxo-1-(oxolan-2-yl)pyrimidine-5-carboxylate Chemical compound O=C1NC(=O)C(C(=O)OC)=CN1C1OCCC1 ZCWVHOWKQQGEPP-UHFFFAOYSA-N 0.000 description 1
- DZPVSYRDDPOTGO-UHFFFAOYSA-N methyl 2,4-dioxo-1h-pyrimidine-5-carboxylate;hydrate Chemical compound O.COC(=O)C1=CNC(=O)NC1=O DZPVSYRDDPOTGO-UHFFFAOYSA-N 0.000 description 1
- LIESVEXYQBSERF-UHFFFAOYSA-N methyl 5-fluoro-4-hydroxy-1-methyl-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound COC(=O)C1(F)C(O)NC(=O)N(C)C1=O LIESVEXYQBSERF-UHFFFAOYSA-N 0.000 description 1
- MUJVMVJSXYNXOE-UHFFFAOYSA-N methyl 5-fluoro-6-hydroxy-2,4-dioxo-1-(oxolan-2-yl)-1,3-diazinane-5-carboxylate Chemical compound O=C1NC(=O)C(C(=O)OC)(F)C(O)N1C1OCCC1 MUJVMVJSXYNXOE-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- XDJVPQDRNIXAEX-UHFFFAOYSA-N octadecyl 4-ethoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1(F)C(OCC)NC(=O)NC1=O XDJVPQDRNIXAEX-UHFFFAOYSA-N 0.000 description 1
- XEFSYBJBSHAHPU-UHFFFAOYSA-N octyl 2,4-dioxo-1h-pyrimidine-5-carboxylate Chemical compound CCCCCCCCOC(=O)C1=CNC(=O)NC1=O XEFSYBJBSHAHPU-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- AITJVHNPNLILEG-UHFFFAOYSA-N propan-2-yl 2,4-dioxo-1h-pyrimidine-5-carboxylate Chemical compound CC(C)OC(=O)C1=CNC(=O)NC1=O AITJVHNPNLILEG-UHFFFAOYSA-N 0.000 description 1
- AJUCOZCPWRGIFR-UHFFFAOYSA-N propan-2-yl 5-fluoro-4-hydroxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CC(C)OC(=O)C1(F)C(O)NC(=O)NC1=O AJUCOZCPWRGIFR-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 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
- 230000035484 reaction time Effects 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
- 210000002966 serum Anatomy 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK385878A DK143599C (da) | 1976-03-31 | 1978-08-31 | Analogifremgangsmaade til fremstilling af 5-fluor-hexahydropyrimidin-5-carboxylsyrederivater |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3665376 | 1976-03-31 | ||
| JP3665376A JPS52118480A (en) | 1976-03-31 | 1976-03-31 | Synthesis of uracil derivatives |
| JP12993276A JPS5353672A (en) | 1976-10-27 | 1976-10-27 | Fluoropyrimidine deivatives |
| JP12993276 | 1976-10-27 | ||
| JP14679576 | 1976-12-06 | ||
| JP14679576A JPS5371086A (en) | 1976-12-06 | 1976-12-06 | Preparation of uracil derivs. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK141177A DK141177A (pt) | 1977-10-01 |
| DK142029B true DK142029B (da) | 1980-08-11 |
| DK142029C DK142029C (pt) | 1981-01-05 |
Family
ID=27289176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK141177AA DK142029B (da) | 1976-03-31 | 1977-03-30 | Analogifremgangsmåde til fremstilling af 5-fluor-hexahydropyrimidin-5-carboxylsyrederivater. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4329460A (pt) |
| CA (1) | CA1081226A (pt) |
| CH (1) | CH632748A5 (pt) |
| DD (2) | DD137353A5 (pt) |
| DE (1) | DE2714392A1 (pt) |
| DK (1) | DK142029B (pt) |
| ES (1) | ES469098A1 (pt) |
| FI (1) | FI770904A (pt) |
| FR (1) | FR2346337A1 (pt) |
| GB (1) | GB1546346A (pt) |
| GR (1) | GR68935B (pt) |
| NL (1) | NL7703541A (pt) |
| NO (1) | NO771124L (pt) |
| PH (1) | PH14553A (pt) |
| PL (1) | PL106917B1 (pt) |
| PT (1) | PT66374B (pt) |
| SE (1) | SE7703721L (pt) |
| SU (1) | SU795467A3 (pt) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57179188A (en) * | 1981-04-28 | 1982-11-04 | Shionogi & Co Ltd | 5-fluorouracil derivative |
| DK167280B1 (da) * | 1985-03-20 | 1993-10-04 | Ciba Geigy Ag | 3-aryluracilderivater, fremgangsmaade til fremstilling deraf, ukrudtsbekaempelsesmidler indeholdende disse derivater samt anvendelsen af derivaterne til ukrudtsbekaempelse |
| US4669081A (en) * | 1986-02-04 | 1987-05-26 | Raytheon Company | LSI fault insertion |
| US4816585A (en) * | 1987-03-05 | 1989-03-28 | Olin Corporation | Tetraalkylpiperidinyl substituted uracil derivatives and their use as ultraviolet light stabilizers |
| US4904714A (en) * | 1987-10-02 | 1990-02-27 | Olin Corporation | Synthetic resin composition and its method of use |
| US4920126A (en) * | 1988-05-10 | 1990-04-24 | Uniroyal Chemical Ltd/Uniroyal Chemical Ltee | Barbituric acid derivative and treatment of leukemia and tumors therewith |
| US5312919A (en) * | 1992-06-12 | 1994-05-17 | Baylor Research Institute | Photooxidation products and derivatives thereof of merocyanine-540, their preparation and uses |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3221010A (en) * | 1963-05-02 | 1965-11-30 | Hoffmann La Roche | 5,6-substituted dihydro-5-fluoropyrimidine nucleosides |
| US3277092A (en) * | 1963-05-02 | 1966-10-04 | Hoffmann La Roche | 5, 6-substituted dihydro-5-fluoropyrimidines |
| US3201387A (en) * | 1963-09-18 | 1965-08-17 | Heidelberger Charles | 5-trifluoromethyluracil, derivatives thereof, and processes for preparing the same |
| US3360523A (en) * | 1964-06-17 | 1967-12-26 | Du Pont | 3, 5, 6-substituted hydrouracils |
| US3406023A (en) * | 1966-10-31 | 1968-10-15 | Du Pont | Herbicidal method |
| US3954758A (en) * | 1970-05-27 | 1976-05-04 | Pcr, Inc. | Process for fluorinating uracil and derivatives thereof |
| CH553195A (de) * | 1971-03-19 | 1974-08-30 | Sandoz Ag | Verfahren zur herstellung neuer 2,6-dichlor-benzaldoximo-(s-triazinyl-(6))-aether. |
| US3987045A (en) * | 1971-05-03 | 1976-10-19 | Basf Aktiengesellschaft | Disperse dyes based on isoindolene derivatives |
| US3954759A (en) * | 1972-07-13 | 1976-05-04 | Pcr, Inc. | Process for preparation of 6-substituted 5-fluorouracil derivatives |
| DE2401619C2 (de) * | 1974-01-14 | 1986-04-03 | Kailash Kumar Prof. Dr. 2359 Lentföhrden Gauri | Fungistatisch wirksame Uracilderivate und Verfahren zu ihrer Herstellung |
| DE2602175B2 (de) * | 1975-01-22 | 1978-05-03 | Asahi Kasei Kogyo K.K., Osaka (Japan) | 1 -Alkanoyl-5-fluor-uracilderivate und ihre Verwendung |
| US4071519A (en) * | 1975-11-05 | 1978-01-31 | Mitsui Toatsu Chemicals, Incorporated | 1-Carbamoyl-5-fluorouracil derivatives |
| US4080455A (en) * | 1975-12-16 | 1978-03-21 | Taisho Pharmaceutical Company Limited | 5-Fluoropyrimidin-4-one compositions |
-
1977
- 1977-03-17 GR GR53014A patent/GR68935B/el unknown
- 1977-03-22 FI FI770904A patent/FI770904A/fi not_active Application Discontinuation
- 1977-03-24 CA CA274,676A patent/CA1081226A/en not_active Expired
- 1977-03-24 CH CH373577A patent/CH632748A5/de not_active IP Right Cessation
- 1977-03-25 GB GB12789/77A patent/GB1546346A/en not_active Expired
- 1977-03-29 FR FR7709280A patent/FR2346337A1/fr active Granted
- 1977-03-30 SE SE7703721A patent/SE7703721L/xx unknown
- 1977-03-30 PT PT66374A patent/PT66374B/pt unknown
- 1977-03-30 DK DK141177AA patent/DK142029B/da not_active IP Right Cessation
- 1977-03-30 PL PL1977197045A patent/PL106917B1/pl unknown
- 1977-03-30 NO NO771124A patent/NO771124L/no unknown
- 1977-03-31 NL NL7703541A patent/NL7703541A/xx not_active Application Discontinuation
- 1977-03-31 SU SU772466666A patent/SU795467A3/ru active
- 1977-03-31 PH PH19603A patent/PH14553A/en unknown
- 1977-03-31 DD DD77206212A patent/DD137353A5/xx unknown
- 1977-03-31 DD DD7700198177A patent/DD132790A5/xx unknown
- 1977-03-31 DE DE19772714392 patent/DE2714392A1/de not_active Withdrawn
-
1978
- 1978-04-01 ES ES469098A patent/ES469098A1/es not_active Expired
-
1979
- 1979-06-13 US US06/048,169 patent/US4329460A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES469098A1 (es) | 1979-09-16 |
| FI770904A (pt) | 1977-10-01 |
| SU795467A3 (ru) | 1981-01-07 |
| NL7703541A (nl) | 1977-10-04 |
| NO771124L (no) | 1977-10-03 |
| PT66374A (en) | 1977-04-01 |
| PH14553A (en) | 1981-09-24 |
| DK141177A (pt) | 1977-10-01 |
| PT66374B (en) | 1978-08-25 |
| PL106917B1 (pl) | 1980-01-31 |
| FR2346337B1 (pt) | 1983-05-13 |
| DD132790A5 (de) | 1978-11-01 |
| DD137353A5 (de) | 1979-08-29 |
| GR68935B (pt) | 1982-03-29 |
| FR2346337A1 (fr) | 1977-10-28 |
| DK142029C (pt) | 1981-01-05 |
| US4329460A (en) | 1982-05-11 |
| SE7703721L (sv) | 1977-10-01 |
| PL197045A1 (pl) | 1978-02-13 |
| DE2714392A1 (de) | 1977-12-22 |
| CH632748A5 (de) | 1982-10-29 |
| CA1081226A (en) | 1980-07-08 |
| GB1546346A (en) | 1979-05-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed | ||
| PBP | Patent lapsed |