GB2056449A - 8-substituted-7-phenyl-1,2,4- triazolo[4,3-c] pyrimidine-5-amines and amides - Google Patents
8-substituted-7-phenyl-1,2,4- triazolo[4,3-c] pyrimidine-5-amines and amides Download PDFInfo
- Publication number
- GB2056449A GB2056449A GB8025795A GB8025795A GB2056449A GB 2056449 A GB2056449 A GB 2056449A GB 8025795 A GB8025795 A GB 8025795A GB 8025795 A GB8025795 A GB 8025795A GB 2056449 A GB2056449 A GB 2056449A
- Authority
- GB
- United Kingdom
- Prior art keywords
- triazolo
- phenyl
- compound
- parts
- amine
- 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.)
- Withdrawn
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- -1 8-substituted-7-phenyl-1,2,4- triazolo[4,3-c] pyrimidine-5-amines Chemical class 0.000 title description 12
- 150000001408 amides Chemical class 0.000 title description 7
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- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- AOXKNJMJBRZSRZ-UHFFFAOYSA-N n-(4-chloro-5-methyl-6-phenylpyrimidin-2-yl)acetamide Chemical compound CC(=O)NC1=NC(Cl)=C(C)C(C=2C=CC=CC=2)=N1 AOXKNJMJBRZSRZ-UHFFFAOYSA-N 0.000 description 1
- VJOCYFUVZJLYJM-UHFFFAOYSA-N n-(8-methyl-7-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)acetamide Chemical compound CC=1C2=NN=CN2C(NC(=O)C)=NC=1C1=CC=CC=C1 VJOCYFUVZJLYJM-UHFFFAOYSA-N 0.000 description 1
- RSZDZHKPBDENGK-UHFFFAOYSA-N n-[4-chloro-5-(2-ethoxyethyl)-6-phenylpyrimidin-2-yl]acetamide Chemical compound CCOCCC1=C(Cl)N=C(NC(C)=O)N=C1C1=CC=CC=C1 RSZDZHKPBDENGK-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000036515 potency Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
Landscapes
- 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
Compounds corresponding to the following general formula: <IMAGE> wherein R represents hydrogen, C1-C4 alkyl, C2-C4 alkoxyalkyl, C2-C4 alkenyl or C2-C4 alkynyl; and R1 represents hydrogen or C1 or C2 1- oxoalkyl, are pharmaceutically active and may be used as diuretic agents, e.g. in pharmaceutical compositions.
Description
SPECIFICATION 8-substituted 7-phenyl-1 2,4-triazolo [4,3-c] pyrimidines-5-amines and amides, preparation and pharmaceutical use thereof
This invention relates to 8-substituted 7phenyl-1 ,2,4-triazolo[4,3-c]pyrimidines-5-amines and amides, preparation and pharmaceutical use thereof.
The present invention provides a compound corresponding to the following general formula:
wherein R represents hydrogen, alkyl containing from 1 to 4 carbon atoms, or alkoxyalkyl, alkenyl or alkynyl containing from 2 to 4 carbon atoms; and R1 represents hydrogen or 1-oxoalkyl containing 1 or 2 carbon atoms.
Those alkyl radicals containing from 1 to 4 carbon atoms and represented by R are typified by methyl, ethyl, propyl and butyl and the corresponding branched-chain isomers.
Those alkoxyalkyl radicals containing from 2 to 4 carbon atoms and represented by R are typified by methoxymethyl, methoxyethyl, 2methoxypropyl, 3-methoxypropyl, ethoxymethyl, 1-ethoxyethyl, 2-ethoxyethyl, ethoxymethyl, propoxymethyl and (1 -methylethoxyethyl).
Those alkenyl and alkynyl radicals containing from 2 to 4 carbon atoms and represented by R are typified by ethenyl, 1-propenyl, 2-propenyl, 1butenyl 2-butenyl, 3-butenyl, ethynyl, 1propynyl, 2-propynyl, 1-butynyl, 2-butynyl and 3butynyl and the corresponding branched chain isomers.
The 1 -oxoalkyl radicals containing 1 or 2 carbon atoms and represented by RX are carbonyl and acetyl.
Such compounds corresponding to the following general formula:
wherein R is defined above; are preferred. It is particularly preferred that R should represent alkyl containing from 1 to 4 carbon atoms or alkoxyalkyl containing from 1 to 4 carbon atoms.
The present compounds are useful because of the valuable pharmacological properties thereof.
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., 7997(1943)] and assigned potencies based upon parallel dose response curves in accordance with Finney (Statistical Method in
Biological Assay, 2nd ed., Charles Griffin 8
Company, Limited, London, 1964]. 8-methyl-7phenyl- 1 ,2,4-triazolo[4,3-c] pyri midine-5-amine and 8-(2-ethoxyethyl )-7-phenyl-[ 1 ,2 ,4]triazolo [4,3-c] pyrimidine-5-amine were found to be 1.2 and 2.7 times as potent as hydrochlorothiazide, respectively. The latter compound is particularly preferred. The typical dosage of hydrochlorothiazide as a diuretic for use in humans is 25 or 50 mg per oral administration.
ror therapeutic purposes, the present compounds are generally combined with one or more pharmaceutically acceptable carriers.
diluents or adjuvants appropriate 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, sodium and calcium salts of phosphoric and sulphuric acids, gelatin, acacia, sodium alginate, polyvinylpyrolidone, and/or polyvinyl alcohol, and thus tableted or encapsulated for convenient administration; alternatively, they maybe dissolved in water or a comparably innocuous liquid. Parenteral administration may be effected via sterile fluid admixture 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 Publishing Co., Eaton, Pa., 1965.
Appropriate dosages, in given instances of course depend upon the nature and severity of the condition treated, the route of administration and the species of mammal involved, including its size and individual idiosyncrasies which obtain.
The present invention also provides such compositions and such pharmaceutical use.
The amines according to the present invention may be prepared by reacting 4-chloro-6phenylpyrimidin-2-amines corresponding to the following general formula:
wherein R is defined as above; with formylhydrazine in dimethylforma mide. The resulting amines may be crystallized in water and recrystallized from methanol.
The amides according to the present invention may be prepared by reacting the corresponding amines with formic or acetic anhydride, depending upon the desired amide.
Alternatively, the present amides may be prepared by reacting appropriate N-(4-chloro-6phenylpipimidin-2-yl)amides corresponding to the following general formula:
wherein R is defined as above; and R1' represents formyl or acetyl; forformylhydrazine in dimethylformamide. The solid product is obtained by the addition of water.
The present invention also provides such a process for the preparation of the above compounds.
The following Examples illustrate the present invention. Unless otherwise indicated, temperatures are given in degrees centigrade and amounts in parts, by weight.
EXAMPLE 1
5.5 parts of 4-chloro-5-methyl-6phenylpyrimidin-2-amine and 3.0 parts of formylhydrazine are added to 50 parts, by volume of dimethylformamide containing 5.0 parts of molecular sieve 3A and refluxed under nitrogen for 2 hours. After standing for 16 hours at room temperature, the solution is poured into cold water. The yellow crystalline product is filtered off, washed with water and dried. The product is recrystallised from methanol to give, as bright yellow needles melting at 258-2600C, 8methyl-7-phenyl-1 ,2,4-triazolo[4,3-c]pyrimidin-5- amine:
EXAMPLE 2
10.0 parts of 4-chloro-5-(2-ethoxyethyl)-6phenylpyrimidin-2-amine and 3.0 parts of formylhydrazine are added to 80 parts, by volume, of dimethylformamide containing 8.0 parts of molecular sieve 3A and refluxed under nitrogen for 2 hours.After standing for 1 6 hours at room temperature, the solution is poured into cold water. The crystalline product is filtered off, washed with water and dried. The product is recrystallized from methanol to give 8-(2ethoxyethyl)-7-phenyl-] 1 ,2,4jtriazolo[4,3- c]pyrimidin-5-amine melting at 1540 C:
EXAMPLE 3
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, of dimethylformamide containing 2.0 parts of molecular sieve 3A and refluxed under nitrogen for 2 hours. The solution is allowed to cool and is poured into cold water. The crystalline product is filtered off, washed with water and dried.The product is recystallized from methanol to give 7phenyl-8-(2-propynyl) [1 ,2,4]triazolo[4,3- c]pyrimidin-5-amine melting at 2400 C:
EXAMPLE 4
6.6 parts of 8-methyl-7-phenyl-1 ,2,4- triazolo[4,3-cjpyrimidin-5-amine (Example 1) is suspended in 50 parts, by volume, of pyridine and 10 parts, by volume, of acetic anhydride. The solution is stirred at room temperature for about 18 hours until a clear solution is formed. After about 21 hours, turbidity develops and a solid gradually forms. After standing for about 40 hours, most of the solvent is removed in vacua. The residue is stirred in water, filtered, washed with water and dried. The product is recrystallized from methanol to give N-(8-methyl-7-phenyl [1 ,2,4]triazolo[4,3-c]pyrimidin-5-yl]aceta mide melting at 2100C:
EXAMPLE 5
Alternatively, the product of Example 4, N-(8 methyl-7-phenyl-[ 1 ,2,4]triazolo[4,3-cjpyrimidine- 5-yl] acetamide, may-be obtained using the appropriate chlorinated pyrimidine. 7.85 parts of N-(4-chloro-5-methyl-6-phenylpyrimidine-2- yl)acetamide:
is added to 6.0 parts of formylhydrazine and 60 parts, by volume, of dimethylformamide. The solution is heated to reflux under nitrogen for 2.5 hours. The solution is allowed to cool and stand at room temperature for 1 6 hours. The clear solution is poured into cold water with stirring. A bright yellow crystalline material is obtained.The material is filtered, washed with water, dried and recrystallized from methanol to give the desired product.
EXAMPLE 6
6.4 parts of N-[4-chloro-5-(2-ethoxyethyl)-6phenylpyrimidin-2-yl]acetamide and 2.4 parts of formylhydrazine are added to 60 parts, by volume, of dimethylformamide containing 6.0 parts of molecular sieve 3A and refluxed under nitrogen for 1 hour. The golden orange solution is then allowed to cool and is poured into water. A bright yellow material is obtained, which is then filtered off, washed with water and dried to give N-[8-(2 ethoxyethyl)-7-phenyl-[ ,2,4]triazolo[4,3- c]pyrimidin-2-yl) acetamide melting at 75-760C:
Having illustrated the preparation of the present compounds, the pharmaceutical use thereof will now be illustrated.
Pharmaceutical formulations were prepared in the following manner, amounts indicating the relative amounts per tablet, capsule, suppository or parenteral product.
Tablets
25 mg of a representative compound, e.g. 8-(2- ethoxyethyl)-7-phenyl-[1,2,4]triazolo[4,3- c]pyrimidine-5-amine were dissolved in isopropyl alcohol and distributed on 191.2 mg. of lactose.
The mixture was air-dried and passed through a 40 mesh screen. 25 mg of corn starch and 7.5 mg of polyvinylpyrrolidone were added to the drug substance lactose mixture, mixed thoroughly and passed through a 40 mesh screen. The mixture was then granulated using isopropyl alcohol, spread on trays and dried at about 490C (1200F.) for 1 6 hours. The dried granulation was then screened. The granules were mixed thoroughly with 1.3 mg of magnesium stearate and the mixture compressed into tablets of the appropriate size. There was thus obtained a tablet having a concentration of active ingredient of 25 mg/tablet.
CAPSULES
25 mg of 8-(2-ethoxyethyl)-7-phenyl [1 ,2,4]triazolo[4,3-c]pyrimidine-5-amine were mixed thoroughly with 1 77.5 mg of corn starch and 177.5 mg of lactose, screened through a 40 mesh screen and remixed. 20 mg of talc were added and the mixture was thoroughly mixed and filled into the appropriate hard gelatin capsule by hand or machine using 400 mg fill per capsule.
There was thus obtained a capsule having a concentration of active ingredients of 25 mg capsule.
In the preparation of tablets and capsules using the present compounds, a variety of excipients may be used. For example: Sugars, such as lactose, sucrose, mannitol, or sorbitol; starches, such as corn starch, tapioca starch, or potato starch; cellulose derivatives, such as sodium carboxymethyl cellulose, ethyl cellulose, or methyl cellulose; gelatine; calcium phosphates, such as dicalcium phosphate or tricalcium phosphate; sodium sulphate; calcium sulphate; polyvinylpyrrolidone; polyvinyl alcohol; stearic acid; alkaline earth metal stearates, such as magnesium stearate; stearic acid vegetable oils, such as peanut oil, cottonseed oil, sesame oil, olive oil, corn oil; surfactants (non-ionic, cationic, anionic); ethylene glycol polymers; betacyclodextrin; fatty alcohols; hydrolyzed cereal solids; as well as other non-toxic compatible fillers, binders, disintegrants, and lubricants commonly used in pharmaceutical formulations.
PARENTERAL PRODUCTS
10 mg of 8-(2-ethoxyethyl)-7-phenyl [1 ,2,4jtriazolo[4,3-c]pyrim din-S-amine was dissolived in 2 ml. of ethanol and 5 ml of sesame oil, filtered and filled into an ampoule and sealed.
the ampoule was then sterilized by an appropriate procedure. There was thus obtained an ampoule having a concentration of active ingredient 10 mg/5ml.
In the preparation of parenteral products using the present compounds a variety of vehicles and solublizers may be used. For example: Vegetable oils, such as peanut, corn, cottonseed, sesame oil, benzyl alcohol, saline, phosphate buffer, water, ethylene glycol polymers, urea, dimethylacetamide, "Triton" (Registered Trade
Mark), dioxolanes, ethyl carbonate ethyl lactate, glycerol formal, isopropyl myristate, surfactants (non-ionic, cationic, anionic), polyalcohols and ethanol.
SUPPOSITORIES
975 mg of cocoa butter were melted, preferably using a water or steam bath to avoid local overheating, then 25 mg of 8-(2 ethoxyethyl)-7-phenyl-[1,2,4]triazolo[4,3- c]pyrimidin-5-amine was either emulsified or suspended in the melt.
The mass was then poured into cooled chromeplated metal moulds and the suppository was readily solidified. The total weight of the suppository was 1000 mg.
In the preparation of suppositories using the present compounds a variety of vehicles and bases for suppository application may be used. For example; Triglycerides of oleic, palmitric, and stearic acids (cocoa butter), partially hydrogenated cottonseed oil, branched saturated fatty alcohols, such as Suppository base G, Hydrogenated coconut oil triglycerides of Ct2C, fatty acids, water dispersible vehicles, such as the polyethylene glycols, glycerin, gelatin, polyoxyl 40 sterarates, and polyethylene-4-sorbitan monostearates, and materials which may raise the melting point of the suppository base, such as beeswax and spermaceti.
Claims (13)
1.A compound corresponding to the following general formula:
wherein R represents hydrogen, C 1-c4alkyl C2-C4 alkoxyalkyl, C2-C4 alkenyl or C2-c4 alkynyl; and R1 represents hydrogen or C1-c2 1 - oxoalkyl.
2. A compound as claimed in claim 1 corresponding to the following general formula:
wherein R' represents C1 or C2 alkylene; R" represents C, or C2 alkyl; and P1 represents hydrogen or C, or C2 1 -oxoalkyl.
3. A compound as claimed in claim 2 corresponding to the following general formula:
wherein R' represents C, or C2 alkylene; and Rn represents CX or C2 alkyl.
4. A compound as claimed in claim 1 corresponding to the following general formula:
wherein R"' represents hydrogen, methyl, ethyl, ethyenyl or ethynyl.
5. N-(8-methyl-7-phenyl-[1 ,2,4]triazolo[4,3- cjpyrimidin-5-yljacetamide.
6. N-(8-(2-ethoxyethyl)-7-phenyl [1,2,4]triazolo[4,3-c] pyrimidin-5-amine.
7.8-rriethyl-7-phenyl-1,2,4-triazolo[4,3- c]pyrimidin-5-amine.
8. A process for the preparation of a compound as claimed in claim 1 substantially as herein described.
9. A process for the preparation of a compound as claimed in claim 1 substantially as herein described with reference to any one of the
Examples.
10. A compound as claimed in claim 1 when prepared by a process as claimed in claim 8 or claim 9.
11. A pharmaceutical composition which comprises a compound as claimed in any of claims 1 to 7 or 10 and a pharmaceutically-acceptable carrier or diluent.
12. A composition as claimed in claim 11 substantially as herein described.
13. The use of a compound as claimed in any of claims 1 to 7 or 10 as a pharmaceutical.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6470779A | 1979-08-08 | 1979-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2056449A true GB2056449A (en) | 1981-03-18 |
Family
ID=22057763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8025795A Withdrawn GB2056449A (en) | 1979-08-08 | 1980-08-07 | 8-substituted-7-phenyl-1,2,4- triazolo[4,3-c] pyrimidine-5-amines and amides |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5632479A (en) |
| AU (1) | AU531507B2 (en) |
| CA (2) | CA1246063B (en) |
| CH (1) | CH645898A5 (en) |
| DE (1) | DE3029871C2 (en) |
| FR (1) | FR2463143A1 (en) |
| GB (1) | GB2056449A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012062704A1 (en) | 2010-11-09 | 2012-05-18 | Cellzome Limited | Pyridine compounds and aza analogues thereof as tyk2 inhibitors |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2056449A (en) | 1979-08-08 | 1981-03-18 | Searle & Co | 8-substituted-7-phenyl-1,2,4- triazolo[4,3-c] pyrimidine-5-amines and amides |
| DK135184A (en) * | 1983-03-03 | 1984-10-10 | Riker Laboratories Inc | TRIAZOL (4.3-C) - AND TRIAZOL (1.5-C) PYRIMIDINES |
| US4528288A (en) * | 1983-05-02 | 1985-07-09 | Riker Laboratories, Inc. | Substituted triazolo[1,5-c]pyrimidines |
| US4532242A (en) * | 1983-05-02 | 1985-07-30 | Riker Laboratories, Inc. | Substituted triazolo[4,3-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 |
| TW440563B (en) * | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| US5958934A (en) * | 1996-05-23 | 1999-09-28 | Syntex (U.S.A.) Inc. | Aryl pyrimidine derivatives and uses thereof |
| US5952331A (en) * | 1996-05-23 | 1999-09-14 | Syntex (Usa) Inc. | Aryl pyrimidine derivatives |
| US12351583B2 (en) * | 2019-04-03 | 2025-07-08 | Chemiteras, Inc. | Triazolopyrimidines based on thymine nucleobase and methods for producing them |
Family Cites Families (5)
| 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 |
| US3284542A (en) | 1963-03-22 | 1966-11-08 | Rexall Drug Chemical | Preparation of high impact compositions from vinyl aromatic monomers and rubbery diolefin polymers |
| US3244715A (en) | 1964-10-30 | 1966-04-05 | Smith Kline French Lab | Phenylimidazo [4, 5-d] pyridazines |
| US3461123A (en) | 1968-04-12 | 1969-08-12 | Merck & Co Inc | 1h-imidazo(4,5-b)pyrazin-2-ones and processes for their preparation |
| GB2056449A (en) | 1979-08-08 | 1981-03-18 | Searle & Co | 8-substituted-7-phenyl-1,2,4- triazolo[4,3-c] pyrimidine-5-amines and amides |
-
1980
- 1980-08-07 GB GB8025795A patent/GB2056449A/en not_active Withdrawn
- 1980-08-07 AU AU61153/80A patent/AU531507B2/en not_active Ceased
- 1980-08-07 DE DE3029871A patent/DE3029871C2/en not_active Expired
- 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 CA000524601A patent/CA1246063B/en not_active Expired
- 1986-12-04 CA CA 524602 patent/CA1246064A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012062704A1 (en) | 2010-11-09 | 2012-05-18 | Cellzome Limited | Pyridine compounds and aza analogues thereof as tyk2 inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3029871A1 (en) | 1981-02-26 |
| FR2463143B1 (en) | 1983-12-16 |
| CH645898A5 (en) | 1984-10-31 |
| JPH029592B2 (en) | 1990-03-02 |
| CA1246063A (en) | 1988-12-06 |
| AU6115380A (en) | 1981-02-12 |
| AU531507B2 (en) | 1983-08-25 |
| CA1246064B (en) | 1988-12-06 |
| DE3029871C2 (en) | 1987-01-15 |
| FR2463143A1 (en) | 1981-02-20 |
| CA1246064A (en) | 1988-12-06 |
| JPS5632479A (en) | 1981-04-01 |
| CA1246063B (en) | 1988-12-06 |
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