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 PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- oxazolidinone
- phenyl
- oxo
- compound
- activity
- 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.)
- Expired - Lifetime
Links
- SBYYYVAMWBVIIX-UHFFFAOYSA-N 5-phenyl-1,3-oxazolidine-2,4-dione Chemical compound O1C(=O)NC(=O)C1C1=CC=CC=C1 SBYYYVAMWBVIIX-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000000935 antidepressant agent Substances 0.000 title description 7
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000002552 dosage form Substances 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 abstract description 7
- 230000001747 exhibiting effect Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 5
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- -1 e.g. Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 201000001916 Hypochondriasis Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940114166 dl dopa Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- BCXCABRDBBWWGY-UHFFFAOYSA-N n-benzyl-n-methylprop-2-yn-1-amine;hydrochloride Chemical compound Cl.C#CCN(C)CC1=CC=CC=C1 BCXCABRDBBWWGY-UHFFFAOYSA-N 0.000 description 1
- 229960004239 pargyline hydrochloride Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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.
Landscapes
- 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)
- 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.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9972570A | 1970-12-18 | 1970-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3699229A true US3699229A (en) | 1972-10-17 |
Family
ID=22276329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US99725A Expired - Lifetime US3699229A (en) | 1970-12-18 | 1970-12-18 | 2-oxo-5-phenyl-4-oxazolidinone as an anti-depressant agent |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3699229A (en) |
Cited By (12)
| 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 |
| US4431810A (en) * | 1981-01-02 | 1984-02-14 | Pfizer Inc. | Intermediates for the preparation of 5-substituted oxazolidine-2,4-diones |
| EP0097453A3 (en) * | 1982-06-23 | 1985-06-12 | Pfizer Inc. | Alicyclic substituted oxazolidine-2,4-diones having hypoglycemic activity |
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2721197A (en) * | 1953-01-05 | 1955-10-18 | Bristol Lab Inc | Bicyclic lactams |
-
1970
- 1970-12-18 US US99725A patent/US3699229A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2721197A (en) * | 1953-01-05 | 1955-10-18 | Bristol Lab Inc | Bicyclic lactams |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4367234A (en) * | 1980-07-28 | 1983-01-04 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| FR2487348A1 (en) * | 1980-07-28 | 1982-01-29 | Pfizer | SUBSTITUTED OXAZOLIDINE-2,4-DIONES IN POSITION 5 WITH HYPOGLYCEMIC ACTIVITY |
| US4812471A (en) * | 1980-07-28 | 1989-03-14 | Pfizer Inc. | Hypoglycemic 5-(isoxazolyl or isothiazolyl)-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 |
| 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 |
| US4407811A (en) * | 1981-01-02 | 1983-10-04 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| US4431810A (en) * | 1981-01-02 | 1984-02-14 | Pfizer Inc. | Intermediates for the preparation of 5-substituted oxazolidine-2,4-diones |
| US4689336A (en) * | 1981-01-02 | 1987-08-25 | 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 |
| EP0097453A3 (en) * | 1982-06-23 | 1985-06-12 | Pfizer Inc. | Alicyclic substituted oxazolidine-2,4-diones having hypoglycemic activity |
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