OA08105A - New process for the preparation of 4 H-1,2,4-triazole derivatives, new triazoles thus obtained, their application as medicaments and the pharmaceutical compositions containing them. - Google Patents
New process for the preparation of 4 H-1,2,4-triazole derivatives, new triazoles thus obtained, their application as medicaments and the pharmaceutical compositions containing them.Info
- Publication number
- OA08105A OA08105A OA58685A OA58685A OA08105A OA 08105 A OA08105 A OA 08105A OA 58685 A OA58685 A OA 58685A OA 58685 A OA58685 A OA 58685A OA 08105 A OA08105 A OA 08105A
- Authority
- OA
- OAPI
- Prior art keywords
- formula
- see diagramm
- radical
- carbon atoms
- alkyl radical
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003852 triazoles Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 1
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 1
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Packaging Of Special Articles (AREA)
- Signal Processing For Digital Recording And Reproducing (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1. Process for the preparation of compounds of formula (IA ) : see diagramm : EP0176444,P12,F1 in which R1 , R2 , R3 and R4 identical or different, in whatever position on the benzene nuclei, represent a hydrogen atom, an hydroxyl radical, an alkyl radical containing from 1 to 4 carbon atoms, an Oalk1, radical, alk1 representing an alkyl radical containing from 1 to 4 carbon atoms, an NH2 , NHalk2 radical, alk2 representing an alkyl radical containing from 1 to 4 carbon atoms ; a radical see diagramm : EP0176444,P12,F2 alk3 and alk'3 , identical or different, representing an alkyl radical containing from 1 to 4 carbon atoms, a halogen atom, a CF3 radical or an NO2 radical, or R1 and R2 and/or R3 and R4 together form a methylenedioxy radical, RA represents a -CHOH-alk4 radical, or a see diagramm : EP0176444,P12,F3 radical, alk4 and alk5 , identical or different, representing an alkyl radical containing from 1 to 4 carbon atoms, in their racemic or optically active forms, as well as their addition salts with acids characterized in that a compound of formula (II) : see diagramm : EP0176444,P13,F3 in which R1 , R2 , R3 and R4 have the significances already indicated, is submitted to the action of a chlorination agent so as to obtain an imidyl chloride of formula (III) : see diagramm : EP0176444,P13,F4 which is submitted to the action of a hydrazide of formula (IV) see diagramm : EP0176444,P13,F5 in racemic or optically active form, in which Z is a see diagramm : EP0176444,P13,F6 group, alk4 being an alkyl radical containing from 1 to 4 carbon atoms, so as to obtain a compound of formula (V), in racemic or optically active form : see diagramm : EP0176444,P13,F7 which is cyclized by heating so as to obtain a compound of formula (I), in racemic or optionally active form, in which R is a see diagramm : EP0176444,P13,F8 group, which if desired is esterified so as to obtain a product of formula (I) in which RA is a see diagramm : EP0176444,P13,F9 group, which products of formula (I) are submitted, if desired, to the cation of an acid so as to form a salt.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8414598A FR2570699B1 (en) | 1984-09-24 | 1984-09-24 | NOVEL PROCESS FOR THE PREPARATION OF 4H-1,2,4-TRIAZOLE DERIVATIVES, NOVEL TRIAZOLES THUS OBTAINED, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA08105A true OA08105A (en) | 1987-03-31 |
Family
ID=9307987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA58685A OA08105A (en) | 1984-09-24 | 1985-09-24 | New process for the preparation of 4 H-1,2,4-triazole derivatives, new triazoles thus obtained, their application as medicaments and the pharmaceutical compositions containing them. |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0176444B1 (en) |
| JP (1) | JPS6185370A (en) |
| AT (1) | ATE40886T1 (en) |
| AU (1) | AU585895B2 (en) |
| CA (1) | CA1256113A (en) |
| DE (1) | DE3568331D1 (en) |
| DK (1) | DK429085A (en) |
| ES (1) | ES8704907A1 (en) |
| FI (1) | FI86178C (en) |
| FR (1) | FR2570699B1 (en) |
| GR (1) | GR852310B (en) |
| HU (1) | HU194188B (en) |
| IE (1) | IE58497B1 (en) |
| OA (1) | OA08105A (en) |
| PT (1) | PT81180B (en) |
| ZA (1) | ZA857294B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8429307D0 (en) * | 1984-11-20 | 1984-12-27 | Shell Int Research | Heterocyclic herbicides |
| BR9105867A (en) * | 1990-08-22 | 1992-11-10 | Central Glass Co Ltd | N-ACYL-N-PHENYLTETRAHYDROFTALAMIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION OF THE SAME, HERBICIDE CONTAINING DERIVATIOVITES AS EFFECTIVE COMPONENTS AND METHOD FOR THE PRODUCTION OF IMIDOILA CHLORIDE |
| US5523325A (en) * | 1993-09-09 | 1996-06-04 | Jacobson; Richard M. | Amidrazones and their use as pesticides |
| KR100470076B1 (en) | 2002-11-27 | 2005-02-05 | 씨제이 주식회사 | 1,2,4-triazole derivatives, processes for the preparation thereof, and pharmaceutical compositions containing the same |
| US8530488B2 (en) * | 2007-10-24 | 2013-09-10 | Generics [Uk] Limited | Crystalline forms of bosentan |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2884424A (en) * | 1957-11-18 | 1959-04-28 | American Cyanamid Co | Production of triazoles and amidrazones of the anthraquinone series |
| FR2244462A1 (en) * | 1973-09-25 | 1975-04-18 | Delalande Sa | Antihypertensive, 5-hydroxy methyl 1,2,4-triazoles - prepd. from aniline and a hydroxy methyl 1,3,4-oxadiazole |
| FR2269938A2 (en) * | 1974-05-08 | 1975-12-05 | Delalande Sa | 5-Hydroxymethyl-3,4-diphenyl-1,2,4-triazoles - with anticholinergic, bronchodilator, antidepressant, analgesic, vasodilator activity, etc. |
| GB1510647A (en) * | 1975-10-10 | 1978-05-10 | Commw Scient Ind Res Org | Triazoles |
| FR2512022A2 (en) * | 1980-08-22 | 1983-03-04 | Roussel Uclaf | 3,4-Di:phenyl 4H-1,2,4-triazole analgesics - e.g. 3-ethyl-4-4 methoxy-phenyl 5-4-di:methylamino-phenyl-4H-1,2,4-triazole |
| FR2488891A1 (en) * | 1980-08-22 | 1982-02-26 | Roussel Uclaf | NOVEL 4H-1,2,4-TRIAZOLE DERIVATIVES, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS A MEDICINAL PRODUCT |
| FR2539127B1 (en) * | 1983-01-10 | 1985-08-23 | Roussel Uclaf | NOVEL 4H-1,2,4-TRIAZOLE DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICAMENTS |
-
1984
- 1984-09-24 FR FR8414598A patent/FR2570699B1/en not_active Expired
-
1985
- 1985-09-23 AT AT85401844T patent/ATE40886T1/en active
- 1985-09-23 EP EP85401844A patent/EP0176444B1/en not_active Expired
- 1985-09-23 GR GR852310A patent/GR852310B/el unknown
- 1985-09-23 DK DK429085A patent/DK429085A/en not_active Application Discontinuation
- 1985-09-23 DE DE8585401844T patent/DE3568331D1/en not_active Expired
- 1985-09-23 ZA ZA857294A patent/ZA857294B/en unknown
- 1985-09-23 HU HU853577A patent/HU194188B/en not_active IP Right Cessation
- 1985-09-23 ES ES547209A patent/ES8704907A1/en not_active Expired
- 1985-09-23 FI FI853643A patent/FI86178C/en not_active IP Right Cessation
- 1985-09-23 CA CA000491319A patent/CA1256113A/en not_active Expired
- 1985-09-23 IE IE233885A patent/IE58497B1/en not_active IP Right Cessation
- 1985-09-24 OA OA58685A patent/OA08105A/en unknown
- 1985-09-24 PT PT81180A patent/PT81180B/en unknown
- 1985-09-24 AU AU47840/85A patent/AU585895B2/en not_active Ceased
- 1985-09-24 JP JP60209044A patent/JPS6185370A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK429085D0 (en) | 1985-09-23 |
| ES547209A0 (en) | 1987-04-16 |
| IE852338L (en) | 1986-03-24 |
| FI86178C (en) | 1992-07-27 |
| AU4784085A (en) | 1986-04-10 |
| FI853643A0 (en) | 1985-09-23 |
| AU585895B2 (en) | 1989-06-29 |
| FI853643L (en) | 1986-03-25 |
| GR852310B (en) | 1986-01-24 |
| CA1256113A (en) | 1989-06-20 |
| ES8704907A1 (en) | 1987-04-16 |
| PT81180B (en) | 1988-01-22 |
| PT81180A (en) | 1985-10-01 |
| HU194188B (en) | 1988-01-28 |
| EP0176444A1 (en) | 1986-04-02 |
| FR2570699B1 (en) | 1987-08-28 |
| JPS6185370A (en) | 1986-04-30 |
| DE3568331D1 (en) | 1989-03-30 |
| DK429085A (en) | 1986-03-25 |
| FR2570699A1 (en) | 1986-03-28 |
| ATE40886T1 (en) | 1989-03-15 |
| IE58497B1 (en) | 1993-10-06 |
| FI86178B (en) | 1992-04-15 |
| HUT40090A (en) | 1986-11-28 |
| ZA857294B (en) | 1986-11-26 |
| EP0176444B1 (en) | 1989-02-22 |
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