DE2535023A1 - Neue oxazolidinone, verfahren zu ihrer herstellung, und ihre verwendung in arzneimitteln - Google Patents
Neue oxazolidinone, verfahren zu ihrer herstellung, und ihre verwendung in arzneimittelnInfo
- Publication number
- DE2535023A1 DE2535023A1 DE19752535023 DE2535023A DE2535023A1 DE 2535023 A1 DE2535023 A1 DE 2535023A1 DE 19752535023 DE19752535023 DE 19752535023 DE 2535023 A DE2535023 A DE 2535023A DE 2535023 A1 DE2535023 A1 DE 2535023A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- compounds
- dose
- manufacture
- 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.)
- Withdrawn
Links
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 24
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 230000000949 anxiolytic effect Effects 0.000 description 5
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 5
- 229960003529 diazepam Drugs 0.000 description 5
- 229960004815 meprobamate Drugs 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000002249 anxiolytic agent Substances 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VHNHOAFXJMMMHV-UHFFFAOYSA-N 3-(phenoxymethyl)-1,3-oxazolidin-2-one Chemical class O=C1OCCN1COC1=CC=CC=C1 VHNHOAFXJMMMHV-UHFFFAOYSA-N 0.000 description 2
- 229910014033 C-OH Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910014570 C—OH Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- JWDYCNIAQWPBHD-UHFFFAOYSA-N 1-(2-methylphenyl)glycerol Chemical compound CC1=CC=CC=C1OCC(O)CO JWDYCNIAQWPBHD-UHFFFAOYSA-N 0.000 description 1
- CASCSTLKRAIFKN-UHFFFAOYSA-N 2-methyl-3-phenoxyoxirane Chemical compound CC1OC1OC1=CC=CC=C1 CASCSTLKRAIFKN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000001914 calming effect Effects 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
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960003861 mephenesin Drugs 0.000 description 1
- ZMNSRFNUONFLSP-UHFFFAOYSA-N mephenoxalone Chemical compound COC1=CC=CC=C1OCC1OC(=O)NC1 ZMNSRFNUONFLSP-UHFFFAOYSA-N 0.000 description 1
- 229960001030 mephenoxalone Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7427702A FR2281114A1 (fr) | 1974-08-09 | 1974-08-09 | Oxazolidinones, leur preparation et leurs applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2535023A1 true DE2535023A1 (de) | 1976-03-04 |
Family
ID=9142294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752535023 Withdrawn DE2535023A1 (de) | 1974-08-09 | 1975-08-06 | Neue oxazolidinone, verfahren zu ihrer herstellung, und ihre verwendung in arzneimitteln |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5143757A (enExample) |
| BE (1) | BE832274A (enExample) |
| CH (1) | CH595344A5 (enExample) |
| DE (1) | DE2535023A1 (enExample) |
| FR (1) | FR2281114A1 (enExample) |
| GB (1) | GB1471809A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2655369A1 (de) * | 1976-12-03 | 1978-06-08 | Schering Ag | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
| US6022926A (en) * | 1997-06-05 | 2000-02-08 | Th. Goldschmidt Ag | Organosilanes and organopolysiloxanes containing 2-oxazolidinone groups, their use as surface-active substances and their use for preparing organosilanes and organopolysiloxanes containing amino or carbamido groups |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0559022A (ja) * | 1991-09-05 | 1993-03-09 | Nippon Paint Co Ltd | ５位に置換基を有する２−オキサゾリジノン化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1284520A (fr) * | 1958-11-03 | 1962-02-16 | American Cyanamid Co | Procédé de préparation de nouveaux composés de 2-oxazolidinones |
| GB893252A (en) * | 1959-07-08 | 1962-04-04 | Robins Co Inc A H | 5-polysubstituted phenoxymethyl-2-oxazolidones |
| US3251836A (en) * | 1961-09-26 | 1966-05-17 | Szabo Hnos Kessler & Cia S R L | Oxazolidone derivatives and their preparation |
-
1974
- 1974-08-09 FR FR7427702A patent/FR2281114A1/fr active Granted
-
1975
- 1975-08-06 DE DE19752535023 patent/DE2535023A1/de not_active Withdrawn
- 1975-08-08 BE BE159069A patent/BE832274A/xx unknown
- 1975-08-08 CH CH1039375A patent/CH595344A5/xx not_active IP Right Cessation
- 1975-08-08 JP JP9712575A patent/JPS5143757A/ja active Pending
- 1975-08-08 GB GB3316475A patent/GB1471809A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2655369A1 (de) * | 1976-12-03 | 1978-06-08 | Schering Ag | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
| US6022926A (en) * | 1997-06-05 | 2000-02-08 | Th. Goldschmidt Ag | Organosilanes and organopolysiloxanes containing 2-oxazolidinone groups, their use as surface-active substances and their use for preparing organosilanes and organopolysiloxanes containing amino or carbamido groups |
Also Published As
| Publication number | Publication date |
|---|---|
| CH595344A5 (enExample) | 1978-02-15 |
| GB1471809A (en) | 1977-04-27 |
| FR2281114A1 (fr) | 1976-03-05 |
| BE832274A (fr) | 1976-02-09 |
| JPS5143757A (ja) | 1976-04-14 |
| FR2281114B1 (enExample) | 1978-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |