FR2463143A1 - Nouveaux 7-phenyl-(1,2,4) - triazolo-(4,3-c) - pyrimidine-5-yl-amines et amides 8-substitues, utiles notamment comme diuretiques, et leur procede de preparation - Google Patents
Nouveaux 7-phenyl-(1,2,4) - triazolo-(4,3-c) - pyrimidine-5-yl-amines et amides 8-substitues, utiles notamment comme diuretiques, et leur procede de preparation Download PDFInfo
- Publication number
- FR2463143A1 FR2463143A1 FR8017582A FR8017582A FR2463143A1 FR 2463143 A1 FR2463143 A1 FR 2463143A1 FR 8017582 A FR8017582 A FR 8017582A FR 8017582 A FR8017582 A FR 8017582A FR 2463143 A1 FR2463143 A1 FR 2463143A1
- Authority
- FR
- France
- Prior art keywords
- phenyl
- triazolo
- pyrimidin
- amines
- group
- 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.)
- Granted
Links
- 150000001408 amides Chemical class 0.000 title claims abstract description 10
- 239000002934 diuretic Substances 0.000 title claims abstract description 5
- 229940030606 diuretics Drugs 0.000 title claims abstract description 4
- -1 USEFUL AS DIURETICS Chemical class 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 239000004480 active ingredient Substances 0.000 claims abstract description 8
- 239000002775 capsule Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 10
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 claims description 9
- 239000000829 suppository Substances 0.000 claims description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
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- FIPBRZXDWSODDX-UHFFFAOYSA-N 4-chloro-6-phenylpyrimidin-2-amine Chemical class NC1=NC(Cl)=CC(C=2C=CC=CC=2)=N1 FIPBRZXDWSODDX-UHFFFAOYSA-N 0.000 claims description 2
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- FWNFVGBOBJFHHJ-UHFFFAOYSA-N 8-methyl-7-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound N1=C(N)N2C=NN=C2C(C)=C1C1=CC=CC=C1 FWNFVGBOBJFHHJ-UHFFFAOYSA-N 0.000 claims 1
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- 125000000129 anionic group Chemical group 0.000 description 2
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- 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 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
- 238000007619 statistical method Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 230000002485 urinary effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000002348 vinylic group Chemical group 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)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6470779A | 1979-08-08 | 1979-08-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2463143A1 true FR2463143A1 (fr) | 1981-02-20 |
| FR2463143B1 FR2463143B1 (enExample) | 1983-12-16 |
Family
ID=22057763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8017582A Granted FR2463143A1 (fr) | 1979-08-08 | 1980-08-08 | Nouveaux 7-phenyl-(1,2,4) - triazolo-(4,3-c) - pyrimidine-5-yl-amines et amides 8-substitues, utiles notamment comme diuretiques, et leur procede de preparation |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5632479A (enExample) |
| AU (1) | AU531507B2 (enExample) |
| CA (2) | CA1246063B (enExample) |
| CH (1) | CH645898A5 (enExample) |
| DE (1) | DE3029871C2 (enExample) |
| FR (1) | FR2463143A1 (enExample) |
| GB (1) | GB2056449A (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU531507B2 (en) | 1979-08-08 | 1983-08-25 | G.D. Searle & Co. | 8-substituted 7-phenyl-1,2,4-triazolo(4,3-c) pyrimidines -5-amines and amides |
| DK135184A (da) * | 1983-03-03 | 1984-10-10 | Riker Laboratories Inc | Triazol(4,3-c)- og triazol(1,5-c)pyrimidiner |
| 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 |
| 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 |
| WO2012062704A1 (en) | 2010-11-09 | 2012-05-18 | Cellzome Limited | Pyridine compounds and aza analogues thereof as tyk2 inhibitors |
| KR102875195B1 (ko) * | 2019-04-03 | 2025-10-22 | 케미테라스, 인크. | 티민 핵산 염기를 베이스로 하는 트리아졸로피리미딘류 및 그 제조 방법 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1205144A (fr) * | 1957-06-14 | 1960-01-29 | Farmaceutici Italia | Procédé pour la synthèse de 7-méthyl-s. triazol (4, 3-c) pyrimidines substituéesen position 5 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU531507B2 (en) | 1979-08-08 | 1983-08-25 | G.D. Searle & Co. | 8-substituted 7-phenyl-1,2,4-triazolo(4,3-c) pyrimidines -5-amines and amides |
-
1980
- 1980-08-07 AU AU61153/80A patent/AU531507B2/en not_active Ceased
- 1980-08-07 GB GB8025795A patent/GB2056449A/en not_active Withdrawn
- 1980-08-07 DE DE3029871A patent/DE3029871C2/de not_active Expired
- 1980-08-08 FR FR8017582A patent/FR2463143A1/fr active Granted
- 1980-08-08 JP JP10910380A patent/JPS5632479A/ja active Granted
- 1980-08-08 CH CH603080A patent/CH645898A5/de not_active IP Right Cessation
-
1986
- 1986-12-04 CA CA000524601A patent/CA1246063B/en not_active Expired
- 1986-12-04 CA CA000524602A patent/CA1246064B/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1205144A (fr) * | 1957-06-14 | 1960-01-29 | Farmaceutici Italia | Procédé pour la synthèse de 7-méthyl-s. triazol (4, 3-c) pyrimidines substituéesen position 5 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1246063A (en) | 1988-12-06 |
| CH645898A5 (de) | 1984-10-31 |
| FR2463143B1 (enExample) | 1983-12-16 |
| AU531507B2 (en) | 1983-08-25 |
| GB2056449A (en) | 1981-03-18 |
| CA1246064A (en) | 1988-12-06 |
| DE3029871A1 (de) | 1981-02-26 |
| AU6115380A (en) | 1981-02-12 |
| CA1246063B (en) | 1988-12-06 |
| JPS5632479A (en) | 1981-04-01 |
| DE3029871C2 (de) | 1987-01-15 |
| JPH029592B2 (enExample) | 1990-03-02 |
| CA1246064B (en) | 1988-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |