FR2224141A2 - 1,3-diphenyl-4-hydroxymethylene-pyrazolinones - their salts and formyl derivs, with analgesic and antiinflammatory activity - Google Patents
1,3-diphenyl-4-hydroxymethylene-pyrazolinones - their salts and formyl derivs, with analgesic and antiinflammatory activityInfo
- Publication number
- FR2224141A2 FR2224141A2 FR7312268A FR7312268A FR2224141A2 FR 2224141 A2 FR2224141 A2 FR 2224141A2 FR 7312268 A FR7312268 A FR 7312268A FR 7312268 A FR7312268 A FR 7312268A FR 2224141 A2 FR2224141 A2 FR 2224141A2
- Authority
- FR
- France
- Prior art keywords
- hydroxymethylene
- formyl
- diphenyl
- salts
- analgesic
- 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
- 230000000202 analgesic effect Effects 0.000 title abstract 2
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 2
- KJTDYKOIYQOORE-UHFFFAOYSA-N 4-(hydroxymethylidene)-2,5-diphenylpyrazolidin-3-one Chemical class C1(=CC=CC=C1)N1NC(C(C1=O)=CO)C1=CC=CC=C1 KJTDYKOIYQOORE-UHFFFAOYSA-N 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical class CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 150000004031 phenylhydrazines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Cpds of formulae (I): (where r1, R2 are H,CF3 provided that both are not H), also their salts with alkali metals and alkaline earth metals, also their formyl deriv. They have antiinflammatory and analgesic activity and are used in clinical doses of 0.25-2g/day. Prepd by reaction of phenylhydrazines with ethyl benzoylacetates, reaction of the prod. with POCl3 and dimethylformamide to give a 1,3-diphenyl-4-dimethylaminolmethyl-2-pyrazolin-5-one which is hydrolysed with NaOH to give the 4-hydroxymethylene (I).
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7312268A FR2224141A2 (en) | 1973-04-05 | 1973-04-05 | 1,3-diphenyl-4-hydroxymethylene-pyrazolinones - their salts and formyl derivs, with analgesic and antiinflammatory activity |
BE145665A BE816611Q (en) | 1970-03-31 | 1974-06-20 | 1,3-diphenyl-4-hydroxymethylene-pyrazolinones - their salts and formyl derivs, with analgesic and antiinflammatory activity |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7312268A FR2224141A2 (en) | 1973-04-05 | 1973-04-05 | 1,3-diphenyl-4-hydroxymethylene-pyrazolinones - their salts and formyl derivs, with analgesic and antiinflammatory activity |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2224141A2 true FR2224141A2 (en) | 1974-10-31 |
FR2224141B2 FR2224141B2 (en) | 1976-07-02 |
Family
ID=9117459
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7312268A Granted FR2224141A2 (en) | 1970-03-31 | 1973-04-05 | 1,3-diphenyl-4-hydroxymethylene-pyrazolinones - their salts and formyl derivs, with analgesic and antiinflammatory activity |
Country Status (1)
Country | Link |
---|---|
FR (1) | FR2224141A2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001032653A1 (en) * | 1999-11-04 | 2001-05-10 | Cephalon, Inc. | Heterocyclic substituted pyrazolones |
-
1973
- 1973-04-05 FR FR7312268A patent/FR2224141A2/en active Granted
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001032653A1 (en) * | 1999-11-04 | 2001-05-10 | Cephalon, Inc. | Heterocyclic substituted pyrazolones |
US6455525B1 (en) | 1999-11-04 | 2002-09-24 | Cephalon, Inc. | Heterocyclic substituted pyrazolones |
US6831075B2 (en) | 1999-11-04 | 2004-12-14 | Cephalon, Inc. | Heterocyclic substituted pyrazolones |
Also Published As
Publication number | Publication date |
---|---|
FR2224141B2 (en) | 1976-07-02 |
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