USRE29607E - Derivatives of 5-hydroxymethyl-3-substituted-2-oxazolidinones, process of preparation thereof and therapeutic application - Google Patents
Derivatives of 5-hydroxymethyl-3-substituted-2-oxazolidinones, process of preparation thereof and therapeutic application Download PDFInfo
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- USRE29607E USRE29607E US05/692,744 US69274476A USRE29607E US RE29607 E USRE29607 E US RE29607E US 69274476 A US69274476 A US 69274476A US RE29607 E USRE29607 E US RE29607E
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- 238000000034 method Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- -1 5-hydroxymethyl-3-substituted-2-oxazolidinones Chemical class 0.000 title description 3
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 claims 2
- 239000011737 fluorine Chemical group 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 101150108015 STR6 gene Proteins 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000202 analgesic effect Effects 0.000 abstract description 3
- 230000002082 anti-convulsion Effects 0.000 abstract description 3
- 230000001430 anti-depressive effect Effects 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 3
- 230000001624 sedative effect Effects 0.000 abstract description 3
- 230000003424 uricosuric effect Effects 0.000 abstract description 3
- 239000002221 antipyretic Substances 0.000 abstract description 2
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 14
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241001279009 Strychnos toxifera Species 0.000 description 2
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000002631 hypothermal effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 201000003004 ptosis Diseases 0.000 description 2
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
- 229960003147 reserpine Drugs 0.000 description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
- 229960005453 strychnine Drugs 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- NADYUTJVFHHOLA-UHFFFAOYSA-N 3-[3-(trifluoromethyl)anilino]propane-1,2-diol Chemical compound OCC(O)CNC1=CC=CC(C(F)(F)F)=C1 NADYUTJVFHHOLA-UHFFFAOYSA-N 0.000 description 1
- DOFPEWKUHZUFJE-UHFFFAOYSA-N 5-(hydroxymethyl)-3-[3-(trifluoromethyl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1OC(CO)CN1C1=CC=CC(C(F)(F)F)=C1 DOFPEWKUHZUFJE-UHFFFAOYSA-N 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 206010020843 Hyperthermia Diseases 0.000 description 1
- 206010065390 Inflammatory pain Diseases 0.000 description 1
- 101100060131 Mus musculus Cdk5rap2 gene Proteins 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- INHHFZUVCCBNTO-UHFFFAOYSA-N PAP Chemical compound OCC(O)CNC1=CC=CC=C1 INHHFZUVCCBNTO-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
- 229960003111 prochlorperazine Drugs 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012345 traction test Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000002485 urinary effect Effects 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
- C07D263/08—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-hydroxymethyl-3-substituted-2-oxazolidinones, their process of preparation and their therapeutic application.
- the compounds according to the present invention correspond to the general formula: ##STR3## in which R represents .[.a hydrogen atom, a halogen atom, an alkyl radical having 1 to 4 carbon atoms or a trifluoromethyl radical..]. .Iadd.m-F, p-F, o-F, p-Cl, p-CH 3 , m-CH 3 or m-CF 3 . .Iaddend.
- the process for the preparation of the compounds according to the present invention comprises cyclising, by the action of ethyl carbonate, a 1-phenylamino-2,3-propanediol of the general formula: ##STR4## in which R has the same significance as in Formula I.
- 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.
- Anti-depressive properties 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 rat.
- 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.
Abstract
Compounds of the formula ##STR1## in which R is H, .[.Cl, F, CH3 or CF3 .]. .Iadd.m-F, p-F, o-F, p-Cl, p-CH3, m-CH3 or m-CF3 .Iaddend.. The compounds are prepared by cyclizing with ethyl carbonate, a compound of the formula ##STR2## The compounds have anti-depressive, myorelaxing, tranquilizing, sedative, analgesic, anti-convulsive, anti-pyretic, anti-inflammatory and uricosuric activities.
Description
The present invention concerns novel derivatives of 5-hydroxymethyl-3-substituted-2-oxazolidinones, their process of preparation and their therapeutic application.
The compounds according to the present invention correspond to the general formula: ##STR3## in which R represents .[.a hydrogen atom, a halogen atom, an alkyl radical having 1 to 4 carbon atoms or a trifluoromethyl radical..]. .Iadd.m-F, p-F, o-F, p-Cl, p-CH3, m-CH3 or m-CF3. .Iaddend.
The process for the preparation of the compounds according to the present invention comprises cyclising, by the action of ethyl carbonate, a 1-phenylamino-2,3-propanediol of the general formula: ##STR4## in which R has the same significance as in Formula I.
The following preparation is given, by way of non-limitative example, to illustrate the present invention.
59 G. OF 1-(M-TRIFLUOROMETHYL PHENYLAMINO)-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 a 5% solution of sodium methylate in methanol is added thereto. The distillation of the ethanol formed during the course of the reaction is then observed. Upon completion thereof any excess ethyl carbonate is removed under reduced pressure and the residue obtained is crystallized 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.
The compounds listed in the following table have been prepared according to the process of the above example:
TABLE I
__________________________________________________________________________
##STR5##
Elementary analysis, percent
Empirical
Mol M.P.
Yield,
Calculated
Found
Code No.
R formula wt. ° C.
percent
C H N C H N
__________________________________________________________________________
67360
H C.sub.10 H.sub.11 NO.sub.3
192.20
129 75 62.16
5.74
7.25
62.20
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
.[. 9217
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.].
__________________________________________________________________________
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.
(1) Anti-depressive properties.--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 rat.
By way of example, several results obtained are listed in the following table:
TABLE II
__________________________________________________________________________
Ptosis
Hypothermia Rat Mouse Ulcers
Effect, Effect, Effect, Effect,
Code No.
Dose.sup.1
° C.
Dose.sup.1
percent
Dose.sup.1
percent
Dose.sup.1
percent
__________________________________________________________________________
67360 200 -3.3
200 70 200 55 -- --
68121 100 -3.3
-- -- 100 45 100 77
68292 100 -2.6
100 75 100 50 100 85
6922 -- -- 100 45 100 55 -- --
69201 100 -2.9
-- -- -- -- -- --
69276 -- -- -- -- -- -- 100 50
__________________________________________________________________________
.sup.1 Expressed in mg./kg./p.o.
(II) Myorelaxing properties.--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, the results obtained with two compounds of Formula I are listed in the following table:
TABLE III
______________________________________
Rotating rod
Code No. Traction test, ED.sub.50
test, ED.sub.50
______________________________________
67360 300 mg./kg./p.o. 160 mg./kg./p.o.
68121 110 mg./kg./p.o.
______________________________________
(III) Tranquillising and sedative action.--These effects are shown by a diminution of exploration curiosity in the enclose of an actimetric cage and of escape in an open field. The compound of Formula I reduce the aggressiveness provoked in 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
Actimetric cage Evasion test
penthiobarbital
Effect, Effect, Effect,
Code No.
Dose.sup.1
percent Dose.sup.1
percent
Dose.sup.1
percent
______________________________________
67360 90 50 200 70 200 80
68121 100 70 -- -- 80 50
______________________________________
.sup.1 Expressed in mg./kg./p.o.
(IV) Analgesic activity.--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
phenylbenzoquinone
Dose in Effect,
Code No. mg./kg./p.o. percent
______________________________________
67360 90 50
68121 45 50
______________________________________
(V) Anti-convulsive properties.--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
Cardizol Strychnine Nicotine
Effect, Effect, Effect,
Code No. Dose.sup.1
percent Dose.sup.1
percent
Dose.sup.1
percent
______________________________________
67360 -- -- 140 50 -- --
68121 120 50 100 50 100 80
68292 -- -- 100 70 100 60
6922 -- -- 100 100 -- --
69155 -- -- 100 65 -- --
______________________________________
.sup.1 Expressed in mg./kg./p.o.
(VI) Anti-pyretic action.--This action is manifested by a diminution of the experimental fever provoked by the administration of barm in the cat.
(VII) Anti-inflammatory effect.--The under-plantar oedema provoked in the rat by the administration of carraghenine is diminished by the compounds of the present invention.
(VIII) Uricosuric action.--After repeated oral administration in the rat, the compounds of Formula I provoke an augmentation of the urinary eliminations 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 VII ______________________________________ Code No. LD50 P.O. (mouse,) mg./kg. ______________________________________ 67360 >1600 68121 1400 68292 1500 6922 1050 69155 1200 69204 >4000 69276 1850 ______________________________________
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.
Claims (5)
- chlorine, fluorine, methyl and trifluoromethyl..]. .[.2. A compound as claimed in claim 1, in which R is chlorine or fluorine..]..Iadd. 3. A compound of the formula .Iadd. ##STR7##
- .Iaddend. .Iadd. 4. A compound of the formula .Iadd. ##STR8##
- .Iaddend. .Iadd. 5. A compound of the formula .Iadd. ##STR9##.Iaddend. in which R is selected from the group consisting of p-methyl and
- m-methyl. .Iadd. 6. A compound of the formula .Iadd. ##STR10##
- .Iaddend. .Iadd. 7. A compound of the formula .Iadd. ##STR11##.Iaddend.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1028770 | 1969-03-18 | ||
| GB1426069 | 1969-03-18 | ||
| UK14260/69 | 1969-03-18 | ||
| US2002070A | 1970-03-16 | 1970-03-16 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2002070A Reissue | 1969-03-18 | 1970-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE29607E true USRE29607E (en) | 1978-04-11 |
Family
ID=27256501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/692,744 Expired - Lifetime USRE29607E (en) | 1969-03-18 | 1976-06-04 | Derivatives of 5-hydroxymethyl-3-substituted-2-oxazolidinones, process of preparation thereof and therapeutic application |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE29607E (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382765A (en) | 1977-02-05 | 1983-05-10 | Henkel Kommanditgesellschaft Auf Aktien | Method of moisturizing the skin with carbamide acid esters |
| EP0184170A2 (en) | 1984-12-05 | 1986-06-11 | E.I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| US4705799A (en) | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
| US4801600A (en) | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4921869A (en) | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4942183A (en) | 1987-10-16 | 1990-07-17 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
| US4965268A (en) | 1987-10-09 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4977173A (en) * | 1987-10-21 | 1990-12-11 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents |
| US4985429A (en) * | 1987-10-09 | 1991-01-15 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US5032605A (en) * | 1987-10-09 | 1991-07-16 | Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl oxa or thia cycloalkylbenzene derivatives useful as antibacterial agents |
| US5036092A (en) * | 1987-10-09 | 1991-07-30 | Du Pont Merck Pharmaceutical | Aminomethyl oxooxazolidinyl azacycloalkylbenzene derivatives useful as antibacterial agents |
| US5036093A (en) * | 1987-10-09 | 1991-07-30 | Du Pont Merck Pharmaceutical | Aminomethyl oxooxazolidinyl azacycloalkylbenzene derivatives useful as antibacterial agents |
| US5039690A (en) * | 1987-10-09 | 1991-08-13 | Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl oxa or thia cycloalkylbenzene derivatives useful as antibacterial agents |
| US5182403A (en) * | 1988-09-15 | 1993-01-26 | The Upjohn Company | Substituted 3(5'indazolyl) oxazolidin-2-ones |
| US5225565A (en) * | 1988-09-15 | 1993-07-06 | The Upjohn Company | Antibacterial 3-(fused-ring substituted)phenyl-5β-amidomethyloxazolidin-2-ones |
| US5231188A (en) * | 1989-11-17 | 1993-07-27 | The Upjohn Company | Tricyclic [6.5.51]-fused oxazolidinone antibacterial agents |
| US5254577A (en) * | 1988-07-29 | 1993-10-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| US5523403A (en) * | 1992-12-08 | 1996-06-04 | The Upjohn Company | Tropone-substituted phenyloxazolidinone antibacterial agents |
| US5654428A (en) * | 1991-11-01 | 1997-08-05 | Pharmacia & Upjohn Company | Substituted heteroarylphenyloxazolidinones |
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| US2437388A (en) * | 1948-03-09 | Z-oxazolidone compounds and proc | ||
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| 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 |
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Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382765A (en) | 1977-02-05 | 1983-05-10 | Henkel Kommanditgesellschaft Auf Aktien | Method of moisturizing the skin with carbamide acid esters |
| US4705799A (en) | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
| EP0184170A2 (en) | 1984-12-05 | 1986-06-11 | E.I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| US5036093A (en) * | 1987-10-09 | 1991-07-30 | Du Pont Merck Pharmaceutical | Aminomethyl oxooxazolidinyl azacycloalkylbenzene derivatives useful as antibacterial agents |
| US4801600A (en) | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4921869A (en) | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4965268A (en) | 1987-10-09 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US5039690A (en) * | 1987-10-09 | 1991-08-13 | Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl oxa or thia cycloalkylbenzene derivatives useful as antibacterial agents |
| US4985429A (en) * | 1987-10-09 | 1991-01-15 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US5032605A (en) * | 1987-10-09 | 1991-07-16 | Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl oxa or thia cycloalkylbenzene derivatives useful as antibacterial agents |
| US5036092A (en) * | 1987-10-09 | 1991-07-30 | Du Pont Merck Pharmaceutical | Aminomethyl oxooxazolidinyl azacycloalkylbenzene derivatives useful as antibacterial agents |
| US4942183A (en) | 1987-10-16 | 1990-07-17 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
| US4977173A (en) * | 1987-10-21 | 1990-12-11 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents |
| US5254577A (en) * | 1988-07-29 | 1993-10-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| US5182403A (en) * | 1988-09-15 | 1993-01-26 | The Upjohn Company | Substituted 3(5'indazolyl) oxazolidin-2-ones |
| US5225565A (en) * | 1988-09-15 | 1993-07-06 | The Upjohn Company | Antibacterial 3-(fused-ring substituted)phenyl-5β-amidomethyloxazolidin-2-ones |
| US5231188A (en) * | 1989-11-17 | 1993-07-27 | The Upjohn Company | Tricyclic [6.5.51]-fused oxazolidinone antibacterial agents |
| US5654428A (en) * | 1991-11-01 | 1997-08-05 | Pharmacia & Upjohn Company | Substituted heteroarylphenyloxazolidinones |
| US5654435A (en) * | 1991-11-01 | 1997-08-05 | Pharmacia & Upjohn Company | Substituted arylphenyloxazolindinones |
| US5756732A (en) * | 1991-11-01 | 1998-05-26 | Pharmacia & Upjohn Company | Substituted heteroarylphenyloxazolidinones |
| US5801246A (en) * | 1991-11-01 | 1998-09-01 | Pharmacia & Upjohn Company | Substituted heteroarylphenyloxazolidinones |
| US5929248A (en) | 1991-11-01 | 1999-07-27 | Pharmacia & Upjohn Company | Substituted heteroarylphenyloxazolidinones |
| US5523403A (en) * | 1992-12-08 | 1996-06-04 | The Upjohn Company | Tropone-substituted phenyloxazolidinone antibacterial agents |
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