CA1246064B - 8-substituted-7-phenyl-[1,2,4]triazolo[2,3- c]pyrimidines-5-amines and amides - Google Patents
8-substituted-7-phenyl-[1,2,4]triazolo[2,3- c]pyrimidines-5-amines and amidesInfo
- Publication number
- CA1246064B CA1246064B CA000524602A CA524602A CA1246064B CA 1246064 B CA1246064 B CA 1246064B CA 000524602 A CA000524602 A CA 000524602A CA 524602 A CA524602 A CA 524602A CA 1246064 B CA1246064 B CA 1246064B
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- formula
- compound
- triazolo
- phenyl
- carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
ABSTRACT
This invention relates to compounds having the formula:
This invention relates to compounds having the formula:
Description
8-SUBSTITUTED-7-PHENYL-[1,2,4]TRIAZOLo[2,3-c]PYRIMIDIN-Summary of Invention This invention relates to 8-substituted-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-amines and amides and a process for their preparation. More particularly, -this in-vention provides new, useful and unobvious chemical compounds of the formula:
~y NHRl R
N I!
wherein R represents hydrogen, alkyl containing 1 to 4 carbon 1~ atoms or alkenyl or alkynyl containing 2 to 4 carbon atoms and Rl represents hydrogen or l-oxoalkyl containing 1 or 2 carbon atoms.
Those alkyl radicals containing 1 to 4 carbon atoms and represented by R are typified by methyl, ethyl, propyl and butyl and the corresponding branched chain isomers.
Those alkenyl and alkynyl radicals containing 2 to 4 carbon atoms and represented by R are typified by ethenyl, l-propenyl, 2-propenyl, l-butenyl, 2-butenyl, 3-butenyl, ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl and 3-~0 butynyl and the corresponding branched chain isomers.
The l-oxoalkyl radicals containing 1 or 2 carbon atoms and represented by Rl are formyl and acetyl.
Embodiments of the present invention of the formula:
~ 2 ~
~NH2 N ~ N
N ~
~erein R is as earlier defined are preferred. In this lat-ter formula the embodiments represented by R equal to alkyl containing 1 to 4 carbon atoms are especially preferred.
The compounds of this invention are useful because of their valuable pharmacological properties. Thus, for example, they are potent diuretics: When assayed for the capacity to increase urine volume as described by Lipschitz et al. [J.
Pharmacol. Exp. Therap., 79:97 (1943)] and assigned potencies based upon parallel dose response curves in accordance with Finney [Statistical Method in Biological Assay, 2nd ed., Charles Griffin & Company, Limited, London, 1964], 8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-amine was found to be 1.2 times as potent as hydrochlorothiazide. The typical dosage of hydrochlorothiazide as a diuretic for use in humans is 25 or 50 mg per oral administration.
For therapeutic purposes, the compounds of this inven-tion are ordinarily combined with one or more adjuvants ap-propriate to the indicated route of administration. If per os, they may be admixed with lactose, sucrose, starch powder, cellulose esters of alkanoic acids~ cellulose alkyl esters, talc, stearic acid, magnesium stearate, magnesium oxide, so-dium and calcium salts of phosphoric and sulfuric acids, yel-atin, acacia, sodium alginate, polyvinylpyrrolidone, and/or polyvinyl alcohol, and thus tableted or encapsulated for con-- 3 - ~ 6~
venient administration; alternatively, they may be dissolved in water or a comparably innocuous liquid. Parenteral admin-istration may be effected via sterile fluid admix-ture with water, polyethylene glycol, propylene glycol, ethanol, corn oil, cottonseed oil, peanut oil, sesame oil, benzyl alcohol, sodium chloride, and/or various buffers. Other adjuvants and modes of administration are well and widely known in the pharmaceutical art; see, for example, F. W. Martin et al., "Remington's Pharmaceutical Sciences", 14th ed., Merck Pub-lishing Co., Eaton, Pa., 1965.
Appropriate dosages, in any given instance, of coursedepend upon the nature and severity of the condition trea-ted, the route of administration, and the species of mammal in-volved, including its size and any individual idiosyncrasies which obtain.
Description of Invention The amines of this invention can be prepared by heat-ing 4-chloro-6-phenylpyrimidin-2-amines of the formula:
~ N ~ NH2 ,~
Cl wherein R is defined as above, with formylhydrazine in dime-~0 thylformamide. The resulting amines can be crystallized in water and recrystallized from methanol.
The amides of this invention can be prepared by con-_ 4 _ ~2~6~
tacting the corresponding amines of this invention with for-mic or acetic anhydride, depending upon the desired amide.
An alternate process for the preparation of the amides of this invention is to heat the appropriate N-(4-chloro-6-phenylpyrimidin-2-yl)amide of the formula:
~NHRl R
Cl wherein R is defined as above and Rl is a formyl or acetyl radical, with formylhydrazine in dimethylformamide. The sol-id product is formed with the addition of water.
The following examples describe in detail compounds illustrative of the present invention and methods for their preparation. However, the invention is not to be construed as limited by the examples since it will be apparent to those skilled in the art of organic synthesis that many modifica-tions, both of materials and of methods, may be practiced without departing from the purpose and intent of this dis-closure. Throughout the examples, temperatures are given in degrees centigrade and relative amounts of materials in parts by weight, except as otherwise noted.
Example 1 5.5 Parts of 4-chloro-5-methyl-6-phenylpyrimidin-2-amine and 3.0 parts of formylhydrazine are added to 50 parts by volume dimethylformamide containing 5.0 parts of molecular sieve 3~ and refluxed under nitrogen for two hours. AEter standing ~or 16 hours at room temperature the solution is poured in cold water. The yellow crystalline product is fil-tered out~ washed with water and dried. The product is re-crystallized from methanol to give/ as bright yellow needles melting at 258C to 260C, the compound which is believed to be 8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-amine having the formula:
~,~ ~ ,~NH2 Example 2 1.7 Parts of 4-chloro-6-phenyl-5-(2-propynyl)pyrimidin-
~y NHRl R
N I!
wherein R represents hydrogen, alkyl containing 1 to 4 carbon 1~ atoms or alkenyl or alkynyl containing 2 to 4 carbon atoms and Rl represents hydrogen or l-oxoalkyl containing 1 or 2 carbon atoms.
Those alkyl radicals containing 1 to 4 carbon atoms and represented by R are typified by methyl, ethyl, propyl and butyl and the corresponding branched chain isomers.
Those alkenyl and alkynyl radicals containing 2 to 4 carbon atoms and represented by R are typified by ethenyl, l-propenyl, 2-propenyl, l-butenyl, 2-butenyl, 3-butenyl, ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl and 3-~0 butynyl and the corresponding branched chain isomers.
The l-oxoalkyl radicals containing 1 or 2 carbon atoms and represented by Rl are formyl and acetyl.
Embodiments of the present invention of the formula:
~ 2 ~
~NH2 N ~ N
N ~
~erein R is as earlier defined are preferred. In this lat-ter formula the embodiments represented by R equal to alkyl containing 1 to 4 carbon atoms are especially preferred.
The compounds of this invention are useful because of their valuable pharmacological properties. Thus, for example, they are potent diuretics: When assayed for the capacity to increase urine volume as described by Lipschitz et al. [J.
Pharmacol. Exp. Therap., 79:97 (1943)] and assigned potencies based upon parallel dose response curves in accordance with Finney [Statistical Method in Biological Assay, 2nd ed., Charles Griffin & Company, Limited, London, 1964], 8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-amine was found to be 1.2 times as potent as hydrochlorothiazide. The typical dosage of hydrochlorothiazide as a diuretic for use in humans is 25 or 50 mg per oral administration.
For therapeutic purposes, the compounds of this inven-tion are ordinarily combined with one or more adjuvants ap-propriate to the indicated route of administration. If per os, they may be admixed with lactose, sucrose, starch powder, cellulose esters of alkanoic acids~ cellulose alkyl esters, talc, stearic acid, magnesium stearate, magnesium oxide, so-dium and calcium salts of phosphoric and sulfuric acids, yel-atin, acacia, sodium alginate, polyvinylpyrrolidone, and/or polyvinyl alcohol, and thus tableted or encapsulated for con-- 3 - ~ 6~
venient administration; alternatively, they may be dissolved in water or a comparably innocuous liquid. Parenteral admin-istration may be effected via sterile fluid admix-ture with water, polyethylene glycol, propylene glycol, ethanol, corn oil, cottonseed oil, peanut oil, sesame oil, benzyl alcohol, sodium chloride, and/or various buffers. Other adjuvants and modes of administration are well and widely known in the pharmaceutical art; see, for example, F. W. Martin et al., "Remington's Pharmaceutical Sciences", 14th ed., Merck Pub-lishing Co., Eaton, Pa., 1965.
Appropriate dosages, in any given instance, of coursedepend upon the nature and severity of the condition trea-ted, the route of administration, and the species of mammal in-volved, including its size and any individual idiosyncrasies which obtain.
Description of Invention The amines of this invention can be prepared by heat-ing 4-chloro-6-phenylpyrimidin-2-amines of the formula:
~ N ~ NH2 ,~
Cl wherein R is defined as above, with formylhydrazine in dime-~0 thylformamide. The resulting amines can be crystallized in water and recrystallized from methanol.
The amides of this invention can be prepared by con-_ 4 _ ~2~6~
tacting the corresponding amines of this invention with for-mic or acetic anhydride, depending upon the desired amide.
An alternate process for the preparation of the amides of this invention is to heat the appropriate N-(4-chloro-6-phenylpyrimidin-2-yl)amide of the formula:
~NHRl R
Cl wherein R is defined as above and Rl is a formyl or acetyl radical, with formylhydrazine in dimethylformamide. The sol-id product is formed with the addition of water.
The following examples describe in detail compounds illustrative of the present invention and methods for their preparation. However, the invention is not to be construed as limited by the examples since it will be apparent to those skilled in the art of organic synthesis that many modifica-tions, both of materials and of methods, may be practiced without departing from the purpose and intent of this dis-closure. Throughout the examples, temperatures are given in degrees centigrade and relative amounts of materials in parts by weight, except as otherwise noted.
Example 1 5.5 Parts of 4-chloro-5-methyl-6-phenylpyrimidin-2-amine and 3.0 parts of formylhydrazine are added to 50 parts by volume dimethylformamide containing 5.0 parts of molecular sieve 3~ and refluxed under nitrogen for two hours. AEter standing ~or 16 hours at room temperature the solution is poured in cold water. The yellow crystalline product is fil-tered out~ washed with water and dried. The product is re-crystallized from methanol to give/ as bright yellow needles melting at 258C to 260C, the compound which is believed to be 8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-amine having the formula:
~,~ ~ ,~NH2 Example 2 1.7 Parts of 4-chloro-6-phenyl-5-(2-propynyl)pyrimidin-
2-amine and 0.84 part of formylhydrazine are added to 20 parts by volume dimethylformamide containing 2.0 parts of molecular sieve 3A and refluxed under nitrogen for two hours. The solu-tion is allowed to cool and is poured in cold water. The cry-stalline product is fil-tered out, washed with water and dried.
The product is recrystallized from methanol to give the com-pound which is believed to be 7-phenyl-8-(2-propynyl)[1,2,4]-triazolo[2,3-c]pyrimidin-5-amine melting at 240C and having the formula:
- 6 ~
, NH 2 HC--CCH2 N~N
N
Example 3 6.6 Parts of the compound which is believed to be 8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-amine (Ex-ample 1) is suspended in 50 parts by volume pyridine and 10 parts by volume acetic anhydride. The solution is stirred at room temperature for approximately 18 hours until a clear solution is formed. After approximately 21 hours turbidity develops and a solid gradually forms. After standing for ap-proximately 40 hours most of the solvent is removed in vacuo.
The residue is stirred in water, filtered, washed With water and dried. The product is recrystallized from methanol to give the compound which is believed to be N-[8-methyl-7-phe-nyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-yl]acetamide melting at 210C and having the formula:
H3C~ N ~N
N ~
Example 4 An alternative process for synthesizing the product N-[8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-yl]ac-etamide of Example 3 is to start with the appropriate chlori-nated pyrimidine. 7.85 Parts of N-(4-chloro-5-methyl-6-phe-nylpyrimidin-2-yl)acetamide having the formula:
N ~ NHCOCH3 ~ N
Cl is added to 6.0 parts of formylhydrazine and 60 parts by vol-ume dimethylformamide. The solution is heated to reflux un-der nitrogen for 2.5 hours. The solution is allowed to cool and stand at room temperature for 16 hours. The clear solu-tion is poured into cold water, with stirring. A bright yel-low crystalline material is formed. The material is filtered, washed with water, dried and recrystallized from methanol to give the compound which is believed to be N-[8-methyl-7-phe-nyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-yl]acetamide.
The product is recrystallized from methanol to give the com-pound which is believed to be 7-phenyl-8-(2-propynyl)[1,2,4]-triazolo[2,3-c]pyrimidin-5-amine melting at 240C and having the formula:
- 6 ~
, NH 2 HC--CCH2 N~N
N
Example 3 6.6 Parts of the compound which is believed to be 8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-amine (Ex-ample 1) is suspended in 50 parts by volume pyridine and 10 parts by volume acetic anhydride. The solution is stirred at room temperature for approximately 18 hours until a clear solution is formed. After approximately 21 hours turbidity develops and a solid gradually forms. After standing for ap-proximately 40 hours most of the solvent is removed in vacuo.
The residue is stirred in water, filtered, washed With water and dried. The product is recrystallized from methanol to give the compound which is believed to be N-[8-methyl-7-phe-nyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-yl]acetamide melting at 210C and having the formula:
H3C~ N ~N
N ~
Example 4 An alternative process for synthesizing the product N-[8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-yl]ac-etamide of Example 3 is to start with the appropriate chlori-nated pyrimidine. 7.85 Parts of N-(4-chloro-5-methyl-6-phe-nylpyrimidin-2-yl)acetamide having the formula:
N ~ NHCOCH3 ~ N
Cl is added to 6.0 parts of formylhydrazine and 60 parts by vol-ume dimethylformamide. The solution is heated to reflux un-der nitrogen for 2.5 hours. The solution is allowed to cool and stand at room temperature for 16 hours. The clear solu-tion is poured into cold water, with stirring. A bright yel-low crystalline material is formed. The material is filtered, washed with water, dried and recrystallized from methanol to give the compound which is believed to be N-[8-methyl-7-phe-nyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-yl]acetamide.
Claims (10)
1. A process for the preparation of a compound of the formula:
wherein R is hydrogen, alkyl having 1 to 4 carbon atoms or alkenyl or alkynyl having 2 to 4 carbon atoms and R1 is hy-drogen or 1-oxoalkyl having 1 or 2 carbon atoms, which com-prises either a) heating a 4-chloro-6-phenylpyrimidin-2-amine of the formula:
wherein R and R1 are defined as above, with for-mylhydrazine in dimethylformamide; or b) reacting an amine of the formula:
with formic or acetic anhydride.
wherein R is hydrogen, alkyl having 1 to 4 carbon atoms or alkenyl or alkynyl having 2 to 4 carbon atoms and R1 is hy-drogen or 1-oxoalkyl having 1 or 2 carbon atoms, which com-prises either a) heating a 4-chloro-6-phenylpyrimidin-2-amine of the formula:
wherein R and R1 are defined as above, with for-mylhydrazine in dimethylformamide; or b) reacting an amine of the formula:
with formic or acetic anhydride.
2. The process according to claim 1a) wherein the heating is carried out under reflux conditions.
3. The process according to claim 1 wherein R is me-thyl and R1 is acetyl and there is thus prepared the compound N-[8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-yl]ac-etamide of the formula:
4. The process according to claim 1 wherein R1 is hy-drogen and R has the formula R"' wherein R"' is hydrogen, me-thyl, ethyl, ethenyl or ethynyl and there is thus prepared a compound of the formula:
wherein R"' has the meaning defined above.
wherein R"' has the meaning defined above.
5. The process according to claim 1 wherein R is me-thyl and R1 is hydrogen and there is thus prepared the com-pound 8-methyl-7-phenyl-[1,2,4]triazolo[2,3-c]pyrimidin-5-amine of the formula:
6. A compound of the formula:
wherein R is hydrogen, alkyl having 1 to 4 carbon atoms or alkenyl or alkynyl having 2 to 4 carbon atoms and R1 is hy-drogen or 1-oxoalkyl having 1 or 2 carbon atoms, whenever prepared according to the process of claim 1.
wherein R is hydrogen, alkyl having 1 to 4 carbon atoms or alkenyl or alkynyl having 2 to 4 carbon atoms and R1 is hy-drogen or 1-oxoalkyl having 1 or 2 carbon atoms, whenever prepared according to the process of claim 1.
7. A compound, as defined in claim 6, whenever pre-pared according to the process of claim 2.
8. The compound N-[8-methyl-7-phenyl-[1,2,4]triazolo-[2,3-c]pyrimidin-5-yl]acetamide having the formula:
whenever prepared according to the process of claim 3.
whenever prepared according to the process of claim 3.
9. A compound of the formula:
wherein R''' is hydrogen, methyl, ethyl, ethenyl or ethynyl, whenever prepared according to the process of claim 4.
wherein R''' is hydrogen, methyl, ethyl, ethenyl or ethynyl, whenever prepared according to the process of claim 4.
10. The compound 8-methyl-7-phenyl [1,2,4]triazolo-[2,3-c]pyrimidin-5-amine of the formula:
whenever prepared according to the process of claim 5.
whenever prepared according to the process of claim 5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6470779A | 1979-08-08 | 1979-08-08 | |
| US06/064,707 | 1979-08-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA1246064A CA1246064A (en) | 1988-12-06 |
| CA1246064B true CA1246064B (en) | 1988-12-06 |
Family
ID=22057763
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000524602A Expired CA1246064B (en) | 1979-08-08 | 1986-12-04 | 8-substituted-7-phenyl-[1,2,4]triazolo[2,3- c]pyrimidines-5-amines and amides |
| CA000524601A Expired CA1246063B (en) | 1979-08-08 | 1986-12-04 | 8-substituted-7-phenyl-[1,2,4]triazolo[2,3- c]pyrimidines-5-amines and amides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000524601A Expired CA1246063B (en) | 1979-08-08 | 1986-12-04 | 8-substituted-7-phenyl-[1,2,4]triazolo[2,3- c]pyrimidines-5-amines and amides |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5632479A (en) |
| AU (1) | AU531507B2 (en) |
| CA (2) | CA1246064B (en) |
| CH (1) | CH645898A5 (en) |
| DE (1) | DE3029871A1 (en) |
| FR (1) | FR2463143A1 (en) |
| GB (1) | GB2056449A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK135184A (en) * | 1983-03-03 | 1984-10-10 | Riker Laboratories Inc | TRIAZOL (4.3-C) - AND TRIAZOL (1.5-C) PYRIMIDINES |
| US4532242A (en) * | 1983-05-02 | 1985-07-30 | Riker Laboratories, Inc. | Substituted triazolo[4,3-c]pyrimidines |
| US4528288A (en) * | 1983-05-02 | 1985-07-09 | Riker Laboratories, Inc. | Substituted triazolo[1,5-c]pyrimidines |
| US4483987A (en) * | 1983-06-20 | 1984-11-20 | G. D. Searle & Co. | 8-Substituted 7-phenyl-1,2,4-triazolo[2,3-c]pyrimidines-5-amines and amides |
| US4866063A (en) * | 1988-12-22 | 1989-09-12 | G. D. Searle & Co. | Diol metabolites of 7-phenyl-1,2,4-triazolo[2,3-c]pyrimidines-5-amines |
| US5952331A (en) * | 1996-05-23 | 1999-09-14 | Syntex (Usa) Inc. | Aryl pyrimidine derivatives |
| US5958934A (en) * | 1996-05-23 | 1999-09-28 | Syntex (U.S.A.) Inc. | Aryl pyrimidine derivatives and uses thereof |
| TW440563B (en) * | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| EP2638018A1 (en) | 2010-11-09 | 2013-09-18 | Cellzome Limited | Pyridine compounds and aza analogues thereof as tyk2 inhibitors |
| EP3950064A4 (en) * | 2019-04-03 | 2023-01-04 | Tera Stone Co., Ltd | Thymine nucleobase-based triazolopyrimidines and production method therefor |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1205144A (en) * | 1957-06-14 | 1960-01-29 | Farmaceutici Italia | Process for the synthesis of 7-methyl-s. triazol (4, 3-c) pyrimidines substituted in position 5 |
-
1980
- 1980-08-07 AU AU61153/80A patent/AU531507B2/en not_active Ceased
- 1980-08-07 DE DE19803029871 patent/DE3029871A1/en active Granted
- 1980-08-07 GB GB8025795A patent/GB2056449A/en not_active Withdrawn
- 1980-08-08 CH CH603080A patent/CH645898A5/en not_active IP Right Cessation
- 1980-08-08 FR FR8017582A patent/FR2463143A1/en active Granted
- 1980-08-08 JP JP10910380A patent/JPS5632479A/en active Granted
-
1986
- 1986-12-04 CA CA000524602A patent/CA1246064B/en not_active Expired
- 1986-12-04 CA CA000524601A patent/CA1246063B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1246063A (en) | 1988-12-06 |
| FR2463143A1 (en) | 1981-02-20 |
| DE3029871C2 (en) | 1987-01-15 |
| JPH029592B2 (en) | 1990-03-02 |
| AU531507B2 (en) | 1983-08-25 |
| FR2463143B1 (en) | 1983-12-16 |
| GB2056449A (en) | 1981-03-18 |
| CA1246063B (en) | 1988-12-06 |
| CA1246064A (en) | 1988-12-06 |
| AU6115380A (en) | 1981-02-12 |
| DE3029871A1 (en) | 1981-02-26 |
| CH645898A5 (en) | 1984-10-31 |
| JPS5632479A (en) | 1981-04-01 |
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Effective date: 20050708 |