USRE29934E - Derivatives of 5-carbamoyloxymethyl-3-substituted-2-oxazolidinones, process of preparation thereof and therapeutic application - Google Patents
Derivatives of 5-carbamoyloxymethyl-3-substituted-2-oxazolidinones, process of preparation thereof and therapeutic application Download PDFInfo
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- USRE29934E USRE29934E US05/663,563 US66356376A USRE29934E US RE29934 E USRE29934 E US RE29934E US 66356376 A US66356376 A US 66356376A US RE29934 E USRE29934 E US RE29934E
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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
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
Definitions
- the present invention concerns novel derivatives of 5-carbamoyloxy-methyl-3-substituted-2-oxazolidinone, their process of preparation and their therapeutic application.
- the compounds according to the present invention correspond to the general formula: ##STR5## .[.in which:.]. .[.R is a hydrogen atom, a halogen atom, an alkyl radical having 1 to 4 carbon atoms or a trifluoromethyl radical; and.].
- R 1 and R 2 each represent a hydrogen atom or a dialkylaminoalkyl radical, or together with the nitrogen atom to which they are attached form a methylpiperazino radical..].
- the process for the preparation of the compounds according to the present invention comprises treating an oxazolidinone of the general formula: ##STR9## in which R has the same significance as in Formula I, with phosgene in the presence of ammonia or an amine of formula: ##STR10## in which R 1 and R 2 have the same significance as in Formula I.
- the oxazolidinone of Formula II is prepared by cyclising, by the action of ethyl carbonate, a 1-phenylamino-2,3-propanediol of the general formula: ##STR11## in which R has the same significance as in Formula I.
- Empirical formula C 11 H 10 F 3 NO 3 .
- Empirical formula C 12 H 11 F 3 N 2 O 4 .
- Table I lists a certain number of intermediate compounds of Formula II prepared according to the first part of the above example, and Table II enumerates a certain number of compounds of Formula I prepared according to the second part of the above example.
- the compounds of Formula I experimentally exert anti-depressive, myorelaxing, tranquillising, sedative, analgesic, anti-convulsive, anti-pyretic, anti-inflammatory and uricosuric activities. Moreover, their toxic effects on animals in the laboratory are little marked.
- the compounds of Formula I are capable of opposing hypothermia and the ptosis provoked by reserpine in the rat and the mouse, as well as the ulcers provoked by reserpine in the rat. Moreover, they oppose the catalepsy provoked by prochlorperazine in the art.
- the compounds of Formula I provoke in the mouse the loss of the righting reflex and inhibit the traction reflexes and the maintenance on a rotating rod.
- the Ed 50 in the traction test and also on the rotating rod is 130 mg./kg./P.O.
- This activity is particularly pronounced against the painful stretching provoked in the mouse by the intraperitoneal administration of phenyl benzoquinone or acetic acid.
- the compounds of Formula I exert in the mouse an antagonism against the lethal effects of cardiazol, strychnine and nicotine. They equally show activity against the tonic hyperextension of an excessive electric shock.
- the compounds of Formula I provoke an augmentation of the urinary elimination of uric acid.
- the compounds of Formula I are indicated in the case of depression and neurosis by depressive and anxious components. They equally possess a favourable effect against contractural and inflammatory pains, with or without hyperthermia.
- They may be administered in the form of tablets and gelules containing 50 to 250 mg. of active ingredient.
- a therapeutic composition comprising a compound of Formula I together with a therapeutically-acceptable carrier.
- Compound No. 6901 in tablet form containing 100 mg. of active ingredient, was administered three times daily for 15 days. The cervical pains disappeared and he was able to hold his head in an upright position. Besides this myorelaxant action, there is equally ascertained a complete sedation of his depressive anxieties.
- Compound No. 6901 in tablet form containing 100 mg. of active ingredient was administered daily for three weeks, brought the subject back to a normal state, his hands no longer trembled, his sleep returned to normal and he no longer suffered from cardiac or digestive troubles. His troubles disappeared and he was able to attack his commercial problems with courage.
- Compound No. 68175 in tablet form containing 100 mg. of active ingredient, was administered 3 times a day for 12 days.
- the sedative and tranquillising action is rapidly manifested, causing the irritability to disappear as well as the pain and insomnia.
- the myorelaxant action was equally evidenced, as shown by the complete disappearance of the interior tension and the pain in the legs.
- her sleep returned to normal.
Abstract
A compound of the formula ##STR1## .[.in which R is H, halogen, alkyl having 1 to 4 carbon atoms or trifluoromethyl, and R1 and R2 each is H or dialkylaminoalkyl or together with N comprise methylpiperazino..]. .Iadd.in which (1) .Iadd. ##STR2##.Iaddend. is -NH2 and R is H, m-CH3, o-CF3, m-Cl, p-Cl, m-Br, m-F, p-F, o-F, p-CH3 or m-CH3, or .Iadd. ##STR3##.Iaddend. and R is H, m-CF3 or m-F, or .Iadd. ##STR4##.Iaddend. and R is H, m-CF3 or m-F.
The compound is prepared by treating the corresponding 5-hydroxymethyl compound with ammonia or an amine in the presence of phosgene.
The compounds possess anti-depressive, myorelaxing, tranquilizing, sedative, analgesic, anti-convulsive, anti-pyretic, anti-inflammatory and uricosuric activities.
Description
This application is related to our application Ser. No. 20,020, filed Mar. 16, 1970 .Iadd.now abandoned. .Iaddend.
The present invention concerns novel derivatives of 5-carbamoyloxy-methyl-3-substituted-2-oxazolidinone, their process of preparation and their therapeutic application.
The compounds according to the present invention correspond to the general formula: ##STR5## .[.in which:.]. .[.R is a hydrogen atom, a halogen atom, an alkyl radical having 1 to 4 carbon atoms or a trifluoromethyl radical; and.].
.[.R1 and R2 each represent a hydrogen atom or a dialkylaminoalkyl radical, or together with the nitrogen atom to which they are attached form a methylpiperazino radical..].
.Iadd.in which (1) .Iadd. ##STR6##.Iaddend. is --NH2 and R is H, m-CF3, o-CF3, m-Cl, p-Cl, m-Br, m-F, p-F, o-F, p-CH3 or m-CH3, or .Iadd. ##STR7##.Iaddend. and R is H, m-CF3 or m-F, or .Iadd. ##STR8##.Iaddend. and R is H, m-CF3 or m-F.
The process for the preparation of the compounds according to the present invention comprises treating an oxazolidinone of the general formula: ##STR9## in which R has the same significance as in Formula I, with phosgene in the presence of ammonia or an amine of formula: ##STR10## in which R1 and R2 have the same significance as in Formula I.
The oxazolidinone of Formula II is prepared by cyclising, by the action of ethyl carbonate, a 1-phenylamino-2,3-propanediol of the general formula: ##STR11## in which R has the same significance as in Formula I.
The following preparation is given, by way of nonlimitative example, to illustrate the present invention.
5-carbamoyloxymethyl-3-m-trifluoromethylphenyl- 2-oxazolidinone (Code No. 68175).
(1) Preparation of 5-hydroxymethyl-3-(m-trifluoromethylphenyl)-2-oxazolidinone (Code No. 68121).
59 g. of 1-(m-trifluoromethylphenylamino)-2,3-propanediol and 118 g. of ethyl carbonate are introduced into a distillation apparatus. The mixture is progressively heated to about 110° C. when dissolution is obtained. Then, 12 ml. of 5% solution of sodium methylate in methanol is added thereto. The distillation of the ethanol formed in the course of the reaction is then observed. Upon completion thereof, any excess ethyl carbonate is removed under reduced pressure; the solid residue obtained is crystallised in isopropyl ether.
Melting point=80° C.
Yield=80%.
Empirical formula=C11 H10 F3 NO3.
Elementary analysis.--Calculated (percent): C, 50.58; H, 3.86; N, 5.36. Found (percent): C, 50.74; H, 3.76; N, 5.56.
(2) Preparation of 5-carbamoyloxymethyl-3-m-trifluoromethyl phenyl)-2-oxazolidinone.
300 ml. of a 20% solution of phosgene in toluene is rapidly added to a solution of 100 g. of 5-hydroxymethyl-3-(m-trifluoromethylphenyl)-2-oxazolidinone in 250 ml. of benzene. 63 g. of N,N-diethylaniline is then slowly added thereto with agitation. The hydrochloride which precipitates is dried and the clear organic solution also obtained is treated with a rapid current of gaseous ammonia. The solution is then treated with water, decanted and the organic phase is concentrated. The solid residue obtained is crystallised in absolute ethanol.
Melting point=123° C.
Yield=50%.
Empirical formula=C12 H11 F3 N2 O4.
Elementary analysis.--Calculated (percent): C, 47.37; H, 3.64; N, 9.21. Found (percent): C, 47.50; H, 3.86; N, 9.39.
The following Table I lists a certain number of intermediate compounds of Formula II prepared according to the first part of the above example, and Table II enumerates a certain number of compounds of Formula I prepared according to the second part of the above example.
TABLE I
__________________________________________________________________________
##STR12##
Elementary analysis
Code Empirical
Mol.
M.P.,
Yield,
Calculated
Found
No. R formula
Wt. ° C.
percent
C H N C H N
__________________________________________________________________________
67360
H C.sub.10 H.sub.11 NO.sub.3
193.20
129 75 62.16
5.74
7.25
63.20
5.87
7.40
68292
m.F.
C.sub.10 H.sub.10 FNO.sub.3
211.19
96 87 56.87
4.77
6.63
56.88
4.92
6.79
69155
p.F.
C.sub.10 H.sub.10 FNO.sub.3
211.19
116 68 56.87
4.77
6.63
56.97
4.77
6.83
69275
o.F.
C.sub.10 H.sub.10 FNO.sub.3
211.19
94 60 56.87
4.77
6.63
56.75
4.73
6.67
6922
p.Cl.
C.sub.10 H.sub.10 ClNO.sub.3
227.64
104 55 52.75
4.43
6.15
53.01
4.53
6.05
69204
p.CH.sub.3
C.sub.11 H.sub.13 NO.sub.3
207.22
145 66 63.75
6.32
6.76
63.93
6.10
6.88
69276
m.CH.sub.3
C.sub.11 H.sub.13 NO.sub.3
207.22
76 70 63.75
6.32
6.76
63.70
6.43
6.78
.[.69217
o.CH.sub.3
C.sub.11 H.sub.13 NO.sub.3
207.22
64 69 63.75
6.32
6.76
63.71
6.37
6.88.].
__________________________________________________________________________
table ii
__________________________________________________________________________
##STR13##
elementary analysis
Code Empirical
Mol.
M.P.,
Yield,
Calculated Found
No. R Salt
formula wt. ° C.
percent
C H N Cl C H N C.sub.1
__________________________________________________________________________
6878
H -- C.sub.11 H.sub.12 N.sub.2 O.sub.4
236.22
130 50 55.93
5.12
11.86
-- 55.73
5.27
11.72
--
6978
o.CF.sub.3
-- C.sub.12 H.sub.11 F.sub.3 N.sub.2 O.sub.4
304.22
135 -- 47.37
3.64
9.21
-- 47.40
3.82
9.41
--
68291
m.Cl
-- C.sub.11 H.sub.11 Cl N.sub.2 O.sub.4
270.67
102 40 48.81
4.10
10.35
-- 48.80
3.88
10.22
--
6902
p.Cl
-- C.sub.11 H.sub.11 Cl N.sub.2 O.sub.4
270.67
120 74 48.81
4.10
10.35
-- 49.01
4.25
10.35
--
6945
m.Br
-- C.sub.11 H.sub.11 Br N.sub.2 O.sub.4
315.12
132 50 41.92
3.52
8.89
-- 42.01
3.72
9.06
--
6901
m.F.
-- C.sub.11 H.sub.11 FN.sub.2 O.sub.4
254.21
110 70 51.97
4.36
11.02
-- 51.93
4.44
11.13
--
69254
p.F.
-- C.sub.11 H.sub.11 FN.sub.2 O.sub.4
254.21
140 60 51.97
4.36
11.02
-- 52.07
4.34
10.82
--
69263
o.F.
-- C.sub.11 H.sub.11 FN.sub.2 O.sub.4
251.21
80 40 51.97
4.36
11.02
-- 52.16
4.34
10.94
--
69252
p.CH.sub.3
-- C.sub.12 H.sub.14 N.sub.2 O.sub.4
250.25
148 60 57.59
5.64
11,20
-- 57.40
5.56
11.40
--
59237
m.CH.sub.3
-- C.sub.12 H.sub.14 N.sub.2 O.sub.4
250.25
105 70 57.59
5.64
11.20
-- 57.40
5.44
11.13
--
.[.69239
O.CH.sub.3
-- C.sub.12 H.sub.14 N.sub.2 O.sub.4
250.25
126 35 57.59
5.64
11.20
-- 57.79
5.72
11.26
--.].
__________________________________________________________________________
##STR14##
__________________________________________________________________________
68327
H -- C.sub.15 H.sub.21 N.sub.3 O.sub.4
307.34
77 50 58.62
6.89
19.67
-- 59.18
7.14
-- --
-- HCl C.sub.15 H.sub.22 Cl N.sub.3 O.sub.4
313.80
168 90 52.40
6.45
12.22
-- 52.32
6.68
12.43
--
6985
m.CF.sub.1
-- C.sub.16 H.sub.20 F.sub.3 N.sub.2 O.sub.4
375.34
78 40 51.20
5.37
11.20
-- 51.18
5.52
11.40
--
69253
m.F -- C.sub.15 H.sub.20 FN.sub.3 O.sub.4
325.33
78 35 55.37
6.20
12.92
-- 55.27
6.13
12.96
--
-- HCl C.sub.15 H.sub.21 Cl FN.sub.3 O.sub.4
361.80
140 -- 49.79
5.85
11.62
-- 49.59
5.97
11.50
--
__________________________________________________________________________
##STR15##
__________________________________________________________________________
68306
H -- C.sub.16 H.sub.21 N.sub.3 O.sub.4
319.35
70 50 60.17
6.63
13.16
-- 59.98
6.42
13.36
--
-- HCl C.sub.16 H.sub.22 ClN.sub.3 O.sub.4
355.82
220 98 54.01
6.23
11.81
9.96
53.81
6.39
11.78
10.13
6089
m.CF.sub.3
-- C.sub.17 H.sub.20 F.sub.3 N.sub.3 O.sub.4
359.34
66 -- 52.71
5.20
10.85
-- 52.71
5.33
10.76
--
-- Maleate
C.sub.21 H.sub.24 F.sub.3 N.sub.3 O.sub.4
503.43
120 80 50.10
4.81
8.35
-- 49.96
5.12
8.54
--
69235
m.F -- C.sub.16 H.sub.20 FN.sub.3 O.sub.4
337.34
75 31 56.96
5.98
12.46
-- 56.77
5.79
12.58
--
-- HCl C.sub.16 H.sub.21 FN.sub.3 O.sub.4
373.81
210 40 51.41
5.66
11.24
-- 51.33
5.46
11.26
--
__________________________________________________________________________
the compounds of Formula I experimentally exert anti-depressive, myorelaxing, tranquillising, sedative, analgesic, anti-convulsive, anti-pyretic, anti-inflammatory and uricosuric activities. Moreover, their toxic effects on animals in the laboratory are little marked.
The compounds of Formula I are capable of opposing hypothermia and the ptosis provoked by reserpine in the rat and the mouse, as well as the ulcers provoked by reserpine in the rat. Moreover, they oppose the catalepsy provoked by prochlorperazine in the art.
By way of example, several results obtained are listed in the following table:
TABLE III
__________________________________________________________________________
Ptosis
Hypothermia Rat Mouse Ulcers Catalepsy
Code Effect, Effect, Effect Effect, Effect,
Number
Dose.sup.1
° C.
Dose.sup.1
percent
Dose.sup.1
percent
Dose.sup.1
percent
Dose.sup.1
percent
__________________________________________________________________________
6878 200 -3.4
200 53 200 55 200 60 -- --
68175
100 -4 -- -- 100 85 -- -- -- --
6901 100 -2.4
100 50 100 60 100 55 200 2.9
68921
100 -3 100 60 100 50 -- -- -- --
6902 100 -2.7
100 45 100 50 -- -- -- --
6945 100 -2.5
100 55 100 45 -- -- -- --
69237
-- -- 100 45 100 45 -- -- -- --
69252
-- -- 100 50 100 50 -- -- -- --
6985 100 -2 -- -- -- -- -- -- -- --
69254
-- -- -- -- 100 54 -- -- -- --
69263
-- -- -- -- 100 50 -- -- -- --
__________________________________________________________________________
.sup.1 Expressed in mg./kg./P.O.
The compounds of Formula I provoke in the mouse the loss of the righting reflex and inhibit the traction reflexes and the maintenance on a rotating rod.
By way of example, for the compound No. 68175, the Ed50 in the traction test and also on the rotating rod is 130 mg./kg./P.O.
These effects are shown by a diminution of the exploration curosity in the enclosure of an actimetric cage and of escape in an open field. The compounds of Formula I reduce the aggresiveness provoked by the passage of an electric current and lower the body temperature of animals. The narcotic effects of penthiobarbital are equally reinforced.
The results obtained with two compounds of Formula I are listed in the following table:
TABLE IV
______________________________________
Potentialisation
of penthio-
Actimetric Evasion test
barbital
Code Effect, Effect, Effect,
Number Dose.sup.1
percent Dose.sup.1
percent
Dose.sup.1
percent
______________________________________
6878 -- -- -- -- 180 50
68175 95 50 200 50 100 60
______________________________________
.sup.1 Expressed in mg./kg./P.O.
This activity is particularly pronounced against the painful stretching provoked in the mouse by the intraperitoneal administration of phenyl benzoquinone or acetic acid.
The results obtained with two compounds of Formula I are shown in the following table:
TABLE V
______________________________________
Protection against
phenyl benzoquinone
Dose in Effect,
Code Number mg./kg./P.O. percent
______________________________________
68175 62 60
6902 100 40
______________________________________
The compounds of Formula I exert in the mouse an antagonism against the lethal effects of cardiazol, strychnine and nicotine. They equally show activity against the tonic hyperextension of an excessive electric shock.
By way of example, the results obtained with several compounds of Formula I are listed in the following table:
TABLE VI
__________________________________________________________________________
Antagonism against-
Cardiazol
Strychnine
Nicotine
Electric shock
Effect, Effect, Effect, Effect,
Code Number
Dose.sup.1
percent
Dose.sup.1
percent
Dose.sup.1
percent
Dose.sup.1
percent
__________________________________________________________________________
6878 -- -- 43 60 -- -- -- --
68175 90 50 20 50 100 90 100 80
6901 -- -- 50 90 -- -- -- --
68291 -- -- 100 100 100 90 -- --
6902 100 60 100 100 100 80 -- --
6945 -- -- 100 100 100 75 -- --
.[.69239
-- -- -- -- 100 40 -- --.].
69237 -- -- 100 80 -- -- -- --
69252 -- -- 100 80 -- -- -- --
6985 -- -- -- -- 100 70 -- --
69254 -- -- 100 100 100 55 -- --
69263 -- -- 100 90 -- -- -- --
__________________________________________________________________________
.sup.1 Expressed in mg./kg./P.O.
This action is manifested by a diminution of the experimental fever provoked by the administration of barm in the cat.
The under-planatar oedema provoked in the rat by the administration of carraghenine is diminished by the compounds of the present invention.
The results obtained with two of the compounds of Formula I are shown in the following table:
TABLE VII
______________________________________
Reduction of
Dose in the oedema,
Code Number mg./kg./P.O. percent
______________________________________
68175 200 65
68291 100 40
______________________________________
After repeated oral administration in the rat, the compounds of Formula I provoke an augmentation of the urinary elimination of uric acid.
In consequence of the results shown above, and the values appearing in the following table, the difference between the pharmacologically-active dose and the lethal dose is sufficiently great to enable the compounds of Formula I to be utilised in therapeutics.
TABLE VIII
______________________________________
L.D..sub.60 P.O. (mouse)
Code No.: Mg./kg.
______________________________________
6878 2,700
68175 2,100
6901 2,800
68291 >3,200
6902 1,500
6945 >3,200
.[.69239 >4,000.].
69237 4,000
69252 >4,000
6985 1,350
69254 2,500
69263 3,400
______________________________________
The compounds of Formula I are indicated in the case of depression and neurosis by depressive and anxious components. They equally possess a favourable effect against contractural and inflammatory pains, with or without hyperthermia.
They may be administered in the form of tablets and gelules containing 50 to 250 mg. of active ingredient.
Hence, according to the present invention there is also provided a therapeutic composition comprising a compound of Formula I together with a therapeutically-acceptable carrier.
Several clinical tests to show the activity of the compounds of the present invention are given below:
1st observation: Mr. M. aged 46.
An intellectual, working in a scientific field of high precision, this man was affected by a spasmodic stiff neck due to anxious and hypochondriac grounds. He complained of cervical pains which prevented him from keeping his head upright and concentrating on his work. As a result, he became apathetic, depressed and profoundly restless about his future.
Compound No. 6901, in tablet form containing 100 mg. of active ingredient, was administered three times daily for 15 days. The cervical pains disappeared and he was able to hold his head in an upright position. Besides this myorelaxant action, there is equally ascertained a complete sedation of his depressive anxieties.
2nd observation: Mr. Z. aged 55.
Professional and financial worries were provoked by a reactive neurosis, manifesting itself by an important irritability making family life very difficult. He complained as well as obstinate insomnia and particularly of diverse symptoms characterised by extra-systoles and occasionally of paroxysmic tachycardia, of globus epigastrus and of transient intestinal troubles. His hands trembled uncontrollably. He sometimes had autolysis notions.
Compound No. 6901 in tablet form containing 100 mg. of active ingredient, was administered daily for three weeks, brought the subject back to a normal state, his hands no longer trembled, his sleep returned to normal and he no longer suffered from cardiac or digestive troubles. His troubles disappeared and he was able to attack his commercial problems with courage.
Observation: Mrs. A. aged 48.
This woman was in a pre-menopause phase. For two years, she complained apart from menstrual troubles, exacerbated nervousness, interior tension sensations and trouble with precordial striction. She also complained of insomnia and a certain pain in the legs in the sleeping position.
Compound No. 68175, in tablet form containing 100 mg. of active ingredient, was administered 3 times a day for 12 days.
The sedative and tranquillising action is rapidly manifested, causing the irritability to disappear as well as the pain and insomnia. Simultaneously, the myorelaxant action was equally evidenced, as shown by the complete disappearance of the interior tension and the pain in the legs. Moreover, her sleep returned to normal.
Claims (2)
- and the pharmaceutically acceptable acid addition salts thereof..]. .[.2. A compound as claimed in claim 1, in which R is a chlorine, bromine or
- fluorine atom..]. .Iadd.3. A compound of the formula .Iadd. ##STR18##.Iaddend. in which (1) .Iadd. ##STR19##.Iaddend. is --NH2 and R is H, m-CF3, o-CF3, m-Cl, p-Cl, m-Br, m-F, p-F, o-F, p-CH3 or m-CH3, or .Iadd. ##STR20##.Iaddend. and R is H, m-CF3 or m-F, or .Iadd. ##STR21##.Iaddend. and R is H, m-CF3 or m-F, and the pharmaceutically acceptable acid addition salts thereof.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB14260/69 | 1969-03-18 | ||
| GB1028770 | 1969-03-18 | ||
| GB1426069 | 1969-03-18 | ||
| US2040170A | 1970-03-17 | 1970-03-17 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2040170A Reissue | 1969-03-18 | 1970-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE29934E true USRE29934E (en) | 1979-03-13 |
Family
ID=27256502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/663,563 Expired - Lifetime USRE29934E (en) | 1969-03-18 | 1976-03-03 | Derivatives of 5-carbamoyloxymethyl-3-substituted-2-oxazolidinones, process of preparation thereof and therapeutic application |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE29934E (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5547950A (en) * | 1992-05-08 | 1996-08-20 | The Upjohn Company | Oxazolidinone antimicrobials containing substituted diazine moieties |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641036A (en) * | 1969-03-18 | 1972-02-08 | Delalande Sa | De ivatives of 5-carbamoyloxymethyl-3-substitutea dd-oxazoli1 0 01 dinoncess of thereof preparation and their therapeutic application |
-
1976
- 1976-03-03 US US05/663,563 patent/USRE29934E/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5547950A (en) * | 1992-05-08 | 1996-08-20 | The Upjohn Company | Oxazolidinone antimicrobials containing substituted diazine moieties |
| US5700799A (en) * | 1992-05-08 | 1997-12-23 | Pharmacia & Upjohn Company | Oxazolidinone antimicrobials containing substituted diazine moieties |
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