US3699229A - 2-oxo-5-phenyl-4-oxazolidinone as an anti-depressant agent - Google Patents

2-oxo-5-phenyl-4-oxazolidinone as an anti-depressant agent Download PDF

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Publication number
US3699229A
US3699229A US99725A US3699229DA US3699229A US 3699229 A US3699229 A US 3699229A US 99725 A US99725 A US 99725A US 3699229D A US3699229D A US 3699229DA US 3699229 A US3699229 A US 3699229A
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oxazolidinone
phenyl
oxo
compound
activity
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US99725A
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Nicholas Peter Plotnikoff
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Abbott Laboratories
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Abbott Laboratories
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
    • C07D263/44—Two oxygen atoms

Definitions

  • the present invention provides a method for treating patients exhibiting these symptoms of depression.
  • This invention relates to a method of treating patients exhibiting symptoms of depression. More particularly, it relates to a method of administering to said patients at least an effective dosage of a composition of 2-ox0-5-phenyl-4-oxazolidinone.
  • CsHs-CH C The above compound can be administered orally or by injection.
  • solutions or suspensions may be prepared by slurrying l-l0 percent of compound in water containing 0.1-2.0 percent of carboxymethylcellulose.
  • Suspensions may also be prepared by using 0.05-0.5 percent tragacanth solutions.
  • tablets, pills, or capsules are easily prepared. Tablets may be prepared to contain between 5 and 25 mg. of the active material together with the usual tableting adjuvants, e.g., coloring agents, flavoring agents, diluents, lubricants, carriers and, if desired, dispersing agents or release retardants.
  • the compound may also be combined with other active compounds such as tranquilizers.
  • the anti-depression agent disclosed here when administered to mammals such as humans is effective in a dosage range of from about 0.1 toabout 200 mg./kg. of body weight daily, either in single or divided dosages. More often the daily dosage range is 0.1- mgJkg.
  • This oxazolidinone compound also exhibits a sedative-tranquilizing activity.
  • EXAMPLE 1 One excellent way of testing the compounds for its anti-depressant activity is via the modified dopa-test described by G. M. Everett et al., Proc. lst lntJSymp.
  • mice are pretreated with a monoamine oxidaseinhibitor, such as an oral administration of 40 ing/kg. of pargyline hydrochloride and then given 200 mg./kg. of dldopa orally, along with a known anti-depressant drug,
  • a monoamine oxidaseinhibitor such as an oral administration of 40 ing/kg. of pargyline hydrochloride and then given 200 mg./kg. of dldopa orally, along with a known anti-depressant drug
  • mice show maximum motor reaction, violent activity umping and fighting.
  • a method of treating a patient exhibiting symptomsof depression comprising administering to said patient at least an anti-depressant effective dosage of a composition comprising 2-oxo-5-phenyl-4-oxazolidinone.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Covers a method of treating patients exhibiting symptoms of depression by administering to said patients a compound comprising 2-oxo-5-phenyl-4-oxazolidinone.

Description

United States Patent Plotnikoff 51 Oct. 17, 1972 2-OXO-5-PHENYL-4-OXAZOLIDINONE [56] References Cited 0 AS AN PRE DE ss-ANT AGENT UNITED STATES PATENTS [72] Inventor: Nicholas Peter Plotnikoff, Village of r Lake Bl ff m 2,721,197 10/1955 'Sheehan ..260/ 239.l [73] Assignee: Abliott Laboratories, North a d, m s Friedman Chwago, Attorney-Robert L. Niblack [22] Filed: Dec. 18, 1970 [57] ABSTRACT [21] Appl. No.: 99,725
Covers a method of treating patients exhibiting symptoms of depression by administering to said patients a U-S- t on 2 xo 5 phenyl 4 0x [51 Int. Cl. ..A6lk 27/00 azolidinone. [58] Field of Search ..424/272; 260/307 C 4 Claims, No Drawings 2-OXO-5-PI'IENYL-4-OXAZOLIDINONE AS AN ANTI-DEPRESSANT AGENT BACKGROUND OF THE INVENTION Patients suffering from depression manifest one or more of a variety of symptoms. Generally speaking'a depressed patient feels incapable of dealing with his responsibilities. The predominate symptoms of depression are hypochondria, anoxeria, insomnia, anergia, an-
hedonia and pessimism. patients suffering from these symptoms are usually treated with anti-depressants. The present invention provides a method for treating patients exhibiting these symptoms of depression.
BRIEF SUMMARY OF THE INVENTION This invention relates to a method of treating patients exhibiting symptoms of depression. More particularly, it relates to a method of administering to said patients at least an effective dosage of a composition of 2-ox0-5-phenyl-4-oxazolidinone.
DETAILED DESCRIPTION OF THE INVENTION The just-mentioned'compound is known and its preparation disclosed, for example in US. Pat. No. 2,721,197. Its structure is as follows:
CsHs-CH C= The above compound can be administered orally or by injection. For the latter, solutions or suspensions may be prepared by slurrying l-l0 percent of compound in water containing 0.1-2.0 percent of carboxymethylcellulose. Suspensions may also be prepared by using 0.05-0.5 percent tragacanth solutions. For oral administration, tablets, pills, or capsules are easily prepared. Tablets may be prepared to contain between 5 and 25 mg. of the active material together with the usual tableting adjuvants, e.g., coloring agents, flavoring agents, diluents, lubricants, carriers and, if desired, dispersing agents or release retardants. The compound may also be combined with other active compounds such as tranquilizers.
The anti-depression agent disclosed here when administered to mammals such as humans is effective in a dosage range of from about 0.1 toabout 200 mg./kg. of body weight daily, either in single or divided dosages. More often the daily dosage range is 0.1- mgJkg.
This oxazolidinone compound also exhibits a sedative-tranquilizing activity.
EXAMPLE 1 One excellent way of testing the compounds for its anti-depressant activity is via the modified dopa-test described by G. M. Everett et al., Proc. lst lntJSymp.
' ing: when dl-dopa is given to untreated mice, no
Antidepressant Drugs, p. 164 (19661.
The above-modified dopa-test is based on the followresponse occurs because of the inactivation of the dopa by endogenous monoamine oxidase. However, if mice are pretreated with a monoamine oxidaseinhibitor, such as an oral administration of 40 ing/kg. of pargyline hydrochloride and then given 200 mg./kg. of dldopa orally, along with a known anti-depressant drug,
0 the mice show maximum motor reaction, violent activity umping and fighting.
TABLE I I Modified Dopa Oral Dose (mgJkgl) Test Rating 2S 1 slight activity 50 2 moderate activity 2 moderate activity 200 3 marked activity Eight hours after administration the activity of this compound was shown as follows:
TABLE II Modified Dopa Oral Dose (mg.(kg.) Test Rating 25 2 moderate activity 50 2 moderate activity 100 2 moderate activity What is claimed is:
1. A method of treating a patient exhibiting symptomsof depression comprising administering to said patient at least an anti-depressant effective dosage of a composition comprising 2-oxo-5-phenyl-4-oxazolidinone.
2. The method'of claim 1 wherein said dosage range is from about 0.1 to about 200 mg. /kg. of body weight daily.
3. The method of claim 2 wherein said dosage range is 0.1-20 mg./kg.
4. The method of claim 1 wherein said compound is administered in a unit dosage form in a pharmaceutically-acceptable carrier, said carrier comprising a major portion of said dosage form.
' Q a s I a a:

Claims (3)

  1. 2. The method of claim 1 wherein said dosage range is from about 0.1 to about 200 mg./kg. of body weight daily.
  2. 3. The method of claim 2 wherein said dosage range is 0.1-20 mg./kg.
  3. 4. The method of claim 1 wherein said compound is administered in a unit dosage form in a pharmaceutically-acceptable carrier, said carrier comprising a major portion of said dosage form.
US99725A 1970-12-18 1970-12-18 2-oxo-5-phenyl-4-oxazolidinone as an anti-depressant agent Expired - Lifetime US3699229A (en)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2487348A1 (en) * 1980-07-28 1982-01-29 Pfizer SUBSTITUTED OXAZOLIDINE-2,4-DIONES IN POSITION 5 WITH HYPOGLYCEMIC ACTIVITY
DE3129275A1 (en) * 1980-07-28 1982-04-22 Pfizer Inc., 10017 New York, N.Y. HYPOGLYKAEMIC 5-SUBSTITUTED OXAZOLIDIN-2,4-DIONE
US4332952A (en) * 1980-07-28 1982-06-01 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
US4342771A (en) * 1981-01-02 1982-08-03 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
US4381308A (en) * 1981-04-23 1983-04-26 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
US4407811A (en) * 1981-01-02 1983-10-04 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
EP0097453A2 (en) * 1982-06-23 1984-01-04 Pfizer Inc. Alicyclic substituted oxazolidine-2,4-diones having hypoglycemic activity
US4431810A (en) * 1981-01-02 1984-02-14 Pfizer Inc. Intermediates for the preparation of 5-substituted oxazolidine-2,4-diones
US4565820A (en) * 1980-07-28 1986-01-21 Pfizer Inc. Hypoglycemic 5-pyrrolyl, indolyl and quinolyl substituted oxazolidine-2,4-diones and their use
US4689336A (en) * 1981-01-02 1987-08-25 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine 2,4-diones
US4753956A (en) * 1981-01-02 1988-06-28 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
US4812471A (en) * 1980-07-28 1989-03-14 Pfizer Inc. Hypoglycemic 5-(isoxazolyl or isothiazolyl)-oxazolidine-2,4-diones

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2721197A (en) * 1953-01-05 1955-10-18 Bristol Lab Inc Bicyclic lactams

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2721197A (en) * 1953-01-05 1955-10-18 Bristol Lab Inc Bicyclic lactams

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2487348A1 (en) * 1980-07-28 1982-01-29 Pfizer SUBSTITUTED OXAZOLIDINE-2,4-DIONES IN POSITION 5 WITH HYPOGLYCEMIC ACTIVITY
DE3129309A1 (en) * 1980-07-28 1982-03-18 Pfizer Inc., 10017 New York, N.Y. HYPOGLYKAEMIC 5-SUBSTITUTED OXAZOLIDIN-2,4-DIONE
DE3129275A1 (en) * 1980-07-28 1982-04-22 Pfizer Inc., 10017 New York, N.Y. HYPOGLYKAEMIC 5-SUBSTITUTED OXAZOLIDIN-2,4-DIONE
US4332952A (en) * 1980-07-28 1982-06-01 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
US4812471A (en) * 1980-07-28 1989-03-14 Pfizer Inc. Hypoglycemic 5-(isoxazolyl or isothiazolyl)-oxazolidine-2,4-diones
US4367234A (en) * 1980-07-28 1983-01-04 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
US4565820A (en) * 1980-07-28 1986-01-21 Pfizer Inc. Hypoglycemic 5-pyrrolyl, indolyl and quinolyl substituted oxazolidine-2,4-diones and their use
US4431810A (en) * 1981-01-02 1984-02-14 Pfizer Inc. Intermediates for the preparation of 5-substituted oxazolidine-2,4-diones
US4407811A (en) * 1981-01-02 1983-10-04 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
US4689336A (en) * 1981-01-02 1987-08-25 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine 2,4-diones
US4753956A (en) * 1981-01-02 1988-06-28 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
US4342771A (en) * 1981-01-02 1982-08-03 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
US4381308A (en) * 1981-04-23 1983-04-26 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine-2,4-diones
EP0097453A2 (en) * 1982-06-23 1984-01-04 Pfizer Inc. Alicyclic substituted oxazolidine-2,4-diones having hypoglycemic activity
EP0097453A3 (en) * 1982-06-23 1985-06-12 Pfizer Inc. Alicyclic substituted oxazolidine-2,4-diones having hypoglycemic activity

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