FR2500450A1 - Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique - Google Patents
Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2500450A1 FR2500450A1 FR8103797A FR8103797A FR2500450A1 FR 2500450 A1 FR2500450 A1 FR 2500450A1 FR 8103797 A FR8103797 A FR 8103797A FR 8103797 A FR8103797 A FR 8103797A FR 2500450 A1 FR2500450 A1 FR 2500450A1
- Authority
- FR
- France
- Prior art keywords
- formula
- compounds
- group
- phenyl
- meta
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 9
- 229940053194 antiepileptics oxazolidine derivative Drugs 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 PHENYL GROUP Chemical group 0.000 claims abstract description 6
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 3
- 230000009758 senescence Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- HDWLUGYOLUHEMN-UHFFFAOYSA-N Dinobuton Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC(C)C HDWLUGYOLUHEMN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 229940126601 medicinal product Drugs 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 230000004927 fusion Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 102000010909 Monoamine Oxidase Human genes 0.000 description 3
- 108010062431 Monoamine oxidase Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GJDYTSVYMHISTE-UHFFFAOYSA-N [Cu]C#C Chemical class [Cu]C#C GJDYTSVYMHISTE-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 2
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
- HTRVALPKPVGOSZ-UHFFFAOYSA-N 4-(4-fluorophenyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(F)C=C1 HTRVALPKPVGOSZ-UHFFFAOYSA-N 0.000 description 1
- OZPIDARUDRKJOF-UHFFFAOYSA-N 4-[2-(3-fluorophenyl)ethyl]aniline Chemical compound C1=CC(N)=CC=C1CCC1=CC=CC(F)=C1 OZPIDARUDRKJOF-UHFFFAOYSA-N 0.000 description 1
- 102100028116 Amine oxidase [flavin-containing] B Human genes 0.000 description 1
- 101710185931 Amine oxidase [flavin-containing] B Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 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 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- NSTWBJKGHIWBTI-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]aniline Chemical compound C1=CC(Cl)=CC=C1CCNC1=CC=CC=C1 NSTWBJKGHIWBTI-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000816 toxic dose Toxicity 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8103797A FR2500450A1 (fr) | 1981-02-25 | 1981-02-25 | Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique |
| IT19730/82A IT1153437B (it) | 1981-02-25 | 1982-02-18 | Derivati 5-amminometil-ossazolidinici, procedimento per la loro preparazione, e loro applicazione in terapia |
| GB8205181A GB2094299B (en) | 1981-02-25 | 1982-02-22 | Oxazolidines |
| LU83963A LU83963A1 (fr) | 1981-02-25 | 1982-02-23 | Nouveaux derives aminomethyl-5 oxazolidiniques,leur procede de preparation et leur application en therapeutique |
| US06/351,888 US4476136A (en) | 1981-02-25 | 1982-02-24 | Aminomethyl-5 oxazolidinic derivatives and therapeutic use thereof |
| CA000396983A CA1178594A (en) | 1981-02-25 | 1982-02-24 | Aminomethyl-5 oxazolidinic derivatives, the process for preparing same and the use thereof in therapeutics |
| CH1139/82A CH653999A5 (fr) | 1981-02-25 | 1982-02-24 | Derives aminomethyl-5 oxazolidiniques, procede de preparation et composition pharmaceutique. |
| SE8201145A SE457258B (sv) | 1981-02-25 | 1982-02-24 | Nya 5-aminometyl-3-aryl-2-oxazolidinoner, foerfarande foer framstaellning daerav samt farmaceutiska kompositioner |
| ES509848A ES509848A0 (es) | 1981-02-25 | 1982-02-24 | "procedimiento para la preparacion de nuevos derivados de la aminometil-5-aril-3-oxazolidinona-2-" |
| NL8200732A NL8200732A (nl) | 1981-02-25 | 1982-02-24 | Nieuwe 5-aminomethyl oxazolidineverbindingen, werkwijze ter bereiding daarvan en hun therapeutische toepassing. |
| AU80756/82A AU553462B2 (en) | 1981-02-25 | 1982-02-24 | Oxazolidinone-2 derivatives |
| BE0/207402A BE892270A (fr) | 1981-02-25 | 1982-02-25 | Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique |
| DE19823206770 DE3206770A1 (de) | 1981-02-25 | 1982-02-25 | Neue derivate des aminomethyl-5 oxazolidins, verfahren zu ihrer herstellung und ihre anwendung zu therapeutischen zwecken |
| JP57028234A JPS5838273A (ja) | 1981-02-25 | 1982-02-25 | 新規な５−アミノメチルオキサゾリジン誘導体及びその製造法並びにこれを含有する薬剤 |
| ES520180A ES8400729A1 (es) | 1981-02-25 | 1983-02-16 | Procedimiento para la preparacion de nuevos derivados de la aminometil-5-aril-3-oxazolidinona-2. |
| GB08417905A GB2141716B (en) | 1981-02-25 | 1984-07-13 | Oxazolidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8103797A FR2500450A1 (fr) | 1981-02-25 | 1981-02-25 | Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2500450A1 true FR2500450A1 (fr) | 1982-08-27 |
| FR2500450B1 FR2500450B1 (en, 2012) | 1983-12-02 |
Family
ID=9255633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8103797A Granted FR2500450A1 (fr) | 1981-02-25 | 1981-02-25 | Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4476136A (en, 2012) |
| JP (1) | JPS5838273A (en, 2012) |
| AU (1) | AU553462B2 (en, 2012) |
| BE (1) | BE892270A (en, 2012) |
| CA (1) | CA1178594A (en, 2012) |
| CH (1) | CH653999A5 (en, 2012) |
| DE (1) | DE3206770A1 (en, 2012) |
| ES (2) | ES509848A0 (en, 2012) |
| FR (1) | FR2500450A1 (en, 2012) |
| GB (2) | GB2094299B (en, 2012) |
| IT (1) | IT1153437B (en, 2012) |
| LU (1) | LU83963A1 (en, 2012) |
| NL (1) | NL8200732A (en, 2012) |
| SE (1) | SE457258B (en, 2012) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0127902A3 (en) * | 1983-06-07 | 1987-09-02 | E.I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| EP0184170A3 (en) * | 1984-12-05 | 1987-09-02 | E.I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| FR2603279A1 (fr) * | 1986-09-03 | 1988-03-04 | Rech Ind | Benzyloxy-phenyl-oxazolidinones, procede de preparation et utilisation en therapeutique |
| EP0259228A1 (fr) * | 1986-09-03 | 1988-03-09 | Delalande S.A. | Dérivés 5-aminoéthylés de l'oxazolidinone-2, leur procédé de préparation et leur application en thérapeutique |
| FR2609029A1 (fr) * | 1986-12-30 | 1988-07-01 | Delalande Sa | Derives 5-aminoethyles de l'oxazolidinone-2, leur procede de preparation et leur application en therapeutique |
| EP0311090A1 (en) * | 1987-10-09 | 1989-04-12 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| EP0312000A1 (en) * | 1987-10-16 | 1989-04-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
| EP0316594A1 (en) * | 1987-10-21 | 1989-05-24 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents |
| EP0352781A3 (en) * | 1988-07-29 | 1990-07-11 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| EP0599023A3 (en) * | 1992-09-30 | 1994-11-23 | Minnesota Mining & Mfg | Fluorochemical amino alcohols. |
| US6051716A (en) * | 1995-09-01 | 2000-04-18 | Pharmacia & Upjohn, Inc. | Phenyloxazolidinones having a c-c bond to 4-8 membered heterocyclic rings |
| US6069145A (en) * | 1996-01-27 | 2000-05-30 | Zeneca Limited | Piperazinonephenyloxazolidinone derivatives and their use as antibacterial agents |
| US6110936A (en) * | 1996-05-11 | 2000-08-29 | Zeneca Limited | 3-phenyl-furan-(5H)-2-one and dihydrofuran-2-one derivatives as antibacterial agents |
| US6194441B1 (en) | 1997-08-22 | 2001-02-27 | Zeneca Ltd. | Oxazolidinone derivatives and their use as antibacterial agents |
| US6271383B1 (en) | 1996-02-24 | 2001-08-07 | Zeneca Limited | Antibiotic oxazolidinone derivatives |
| US6495551B1 (en) | 1997-11-29 | 2002-12-17 | Michael John Betts | Substituted phenyloxazolidinones and their use as antibiotics |
| US6605630B1 (en) | 1997-08-22 | 2003-08-12 | Syngenta Limited | Antibiotic oxazolidinone derivatives |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705799A (en) * | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
| DE3723797A1 (de) * | 1987-07-18 | 1989-01-26 | Merck Patent Gmbh | Oxazolidinone |
| US4965268A (en) * | 1987-10-09 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene 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 |
| US4921869A (en) * | 1987-10-09 | 1990-05-01 | 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 |
| US4985429A (en) * | 1987-10-09 | 1991-01-15 | 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 |
| 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 |
| US5225565A (en) * | 1988-09-15 | 1993-07-06 | The Upjohn Company | Antibacterial 3-(fused-ring substituted)phenyl-5β-amidomethyloxazolidin-2-ones |
| US5182403A (en) * | 1988-09-15 | 1993-01-26 | The Upjohn Company | Substituted 3(5'indazolyl) oxazolidin-2-ones |
| US5231188A (en) * | 1989-11-17 | 1993-07-27 | The Upjohn Company | Tricyclic [6.5.51]-fused oxazolidinone antibacterial agents |
| JP3176626B2 (ja) * | 1991-11-01 | 2001-06-18 | ファルマシア・アンド・アップジョン・カンパニー | 抗菌剤として有用な置換アリール−およびヘテロアリールフェニルオキサゾリジノン類 |
| DK0673370T3 (da) * | 1992-12-08 | 1998-09-07 | Upjohn Co | Troponsubstituerede phenyloxazolidinoner som antibakterielle midler |
| TW286317B (en, 2012) * | 1993-12-13 | 1996-09-21 | Hoffmann La Roche | |
| US5668286A (en) * | 1994-03-15 | 1997-09-16 | Pharmacia & Upjohn Company | Oxazolidinone derivatives and pharmaceutical compositions containing them |
| MX9703040A (es) * | 1995-09-12 | 1997-07-31 | Upjohn Co | Antimicrobianos de feniloxazolidinona. |
| FR2741071B1 (fr) * | 1995-11-09 | 1997-12-12 | Synthelabo | Derives de 3-(benzofuran-5-yl)oxazolidin-2-one, leur preparation et leur application en therapeutique |
| JP2000508312A (ja) * | 1996-04-11 | 2000-07-04 | ファルマシア・アンド・アップジョン・カンパニー | オキサゾリジノンの製法 |
| HUP0004388A3 (en) * | 1997-11-07 | 2001-10-29 | Upjohn Co | Process for the preparation of oxazolidinones, intermediates and preparation thereof |
| US6617339B1 (en) * | 1998-06-05 | 2003-09-09 | Syngenta Limited | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| US6444813B2 (en) * | 2000-02-02 | 2002-09-03 | Pharmacia & Upjohn Company | Linezolid-crystal form II |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| WO2002018354A1 (en) * | 2000-08-31 | 2002-03-07 | Abbott Laboratories | Oxazolidinones and their use as antibacterial agents |
| US6410728B1 (en) * | 2000-08-31 | 2002-06-25 | Abbott Laboratories | Oxazolidinone chemotherapeutic agents |
| ES2256318T3 (es) | 2000-10-17 | 2006-07-16 | PHARMACIA & UPJOHN COMPANY LLC | Metodos de produccion de compuestos de oxazolidinona. |
| KR100854211B1 (ko) | 2003-12-18 | 2008-08-26 | 동아제약주식회사 | 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물 |
| WO2006013049A2 (en) * | 2004-08-02 | 2006-02-09 | F.Hoffmann-La Roche Ag | Benzyloxy derivatives as maob inhibitors |
| EP2346858B1 (en) * | 2008-10-10 | 2019-08-07 | Merck Sharp & Dohme Corp. | Methods for preparing oxazolidinones and compositions containing them |
| SG173497A1 (en) | 2009-02-03 | 2011-09-29 | Trius Therapeutics | Crystalline form of r)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate |
| US8580767B2 (en) * | 2009-05-28 | 2013-11-12 | Trius Therapeutics, Inc. | Oxazolidinone containing dimer compounds, compositions and methods to make and use |
| WO2017066964A1 (en) * | 2015-10-22 | 2017-04-27 | Merck Sharp & Dohme Corp. | Oxazolidinone compounds and methods of use thereof as antibacterial agents |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2021204A1 (en, 2012) * | 1968-10-22 | 1970-07-17 | Delalande Sa | |
| FR2428032A1 (fr) * | 1978-06-09 | 1980-01-04 | Delalande Sa | Nouvelles oxazolidimones, oxazolidinethiones et pyrrolidinones, leur procede de preparation et leur application en therapeutique |
| FR2435473A2 (fr) * | 1978-08-17 | 1980-04-04 | Delalande Sa | Nouvelles n-aryle oxazolidinones, oxazolidinethiones et pyrrolidinones, leur procede de preparation et leur application en therapeutique |
| FR2458547A2 (fr) * | 1978-06-09 | 1981-01-02 | Delalande Sa | Nouvelles n-aryle azolones, leur procede de preparation et leur application en therapeutique |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1180089A (en) * | 1967-10-20 | 1970-02-04 | Delalande Sa | Acetylenic Derivatives of 2-Oxazolidinones and processes of preparation |
| LU80081A1 (fr) * | 1977-08-26 | 1979-05-15 | Delalande Sa | Nouvelles hydroxymethyl-5 oxazolidinones-2,leur procede de preparation et leur application therapeutique |
| US4348393A (en) * | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
| CA1171865A (en) * | 1980-06-04 | 1984-07-31 | Alain Lacour | N-aryl azolone derivatives, the process for preparing the same and their application in therapeutics |
-
1981
- 1981-02-25 FR FR8103797A patent/FR2500450A1/fr active Granted
-
1982
- 1982-02-18 IT IT19730/82A patent/IT1153437B/it active
- 1982-02-22 GB GB8205181A patent/GB2094299B/en not_active Expired
- 1982-02-23 LU LU83963A patent/LU83963A1/fr unknown
- 1982-02-24 CH CH1139/82A patent/CH653999A5/fr not_active IP Right Cessation
- 1982-02-24 ES ES509848A patent/ES509848A0/es active Granted
- 1982-02-24 AU AU80756/82A patent/AU553462B2/en not_active Ceased
- 1982-02-24 NL NL8200732A patent/NL8200732A/nl not_active Application Discontinuation
- 1982-02-24 CA CA000396983A patent/CA1178594A/en not_active Expired
- 1982-02-24 US US06/351,888 patent/US4476136A/en not_active Expired - Fee Related
- 1982-02-24 SE SE8201145A patent/SE457258B/sv not_active IP Right Cessation
- 1982-02-25 JP JP57028234A patent/JPS5838273A/ja active Granted
- 1982-02-25 DE DE19823206770 patent/DE3206770A1/de not_active Withdrawn
- 1982-02-25 BE BE0/207402A patent/BE892270A/fr unknown
-
1983
- 1983-02-16 ES ES520180A patent/ES8400729A1/es not_active Expired
-
1984
- 1984-07-13 GB GB08417905A patent/GB2141716B/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2021204A1 (en, 2012) * | 1968-10-22 | 1970-07-17 | Delalande Sa | |
| FR2428032A1 (fr) * | 1978-06-09 | 1980-01-04 | Delalande Sa | Nouvelles oxazolidimones, oxazolidinethiones et pyrrolidinones, leur procede de preparation et leur application en therapeutique |
| FR2458547A2 (fr) * | 1978-06-09 | 1981-01-02 | Delalande Sa | Nouvelles n-aryle azolones, leur procede de preparation et leur application en therapeutique |
| FR2435473A2 (fr) * | 1978-08-17 | 1980-04-04 | Delalande Sa | Nouvelles n-aryle oxazolidinones, oxazolidinethiones et pyrrolidinones, leur procede de preparation et leur application en therapeutique |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0127902A3 (en) * | 1983-06-07 | 1987-09-02 | E.I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| EP0184170A3 (en) * | 1984-12-05 | 1987-09-02 | E.I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| FR2603279A1 (fr) * | 1986-09-03 | 1988-03-04 | Rech Ind | Benzyloxy-phenyl-oxazolidinones, procede de preparation et utilisation en therapeutique |
| EP0259228A1 (fr) * | 1986-09-03 | 1988-03-09 | Delalande S.A. | Dérivés 5-aminoéthylés de l'oxazolidinone-2, leur procédé de préparation et leur application en thérapeutique |
| US4897409A (en) * | 1986-09-03 | 1990-01-30 | Delalande S.A. | 5-aminoethyloxazolidin-2-one derivatives |
| FR2609029A1 (fr) * | 1986-12-30 | 1988-07-01 | Delalande Sa | Derives 5-aminoethyles de l'oxazolidinone-2, leur procede de preparation et leur application en therapeutique |
| EP0311090A1 (en) * | 1987-10-09 | 1989-04-12 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| EP0312000A1 (en) * | 1987-10-16 | 1989-04-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
| EP0316594A1 (en) * | 1987-10-21 | 1989-05-24 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents |
| EP0352781A3 (en) * | 1988-07-29 | 1990-07-11 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| EP0599023A3 (en) * | 1992-09-30 | 1994-11-23 | Minnesota Mining & Mfg | Fluorochemical amino alcohols. |
| US6051716A (en) * | 1995-09-01 | 2000-04-18 | Pharmacia & Upjohn, Inc. | Phenyloxazolidinones having a c-c bond to 4-8 membered heterocyclic rings |
| US6166056A (en) * | 1995-09-01 | 2000-12-26 | Pharmacia | Phenyloxazolidinones having a C-C bond to 4-8 membered heterocyclic rings |
| US6313307B1 (en) | 1995-09-01 | 2001-11-06 | Pharmacia & Upjohn Company | Phenyloxazolidinones having a C-C bond to 4-8 membered heterocyclic rings |
| US6358942B1 (en) | 1995-09-01 | 2002-03-19 | Pharmacia & Upjohn Company | Phenyloxazolidinones having a c-c bond 4-8 membered heterocyclic rings |
| US6069145A (en) * | 1996-01-27 | 2000-05-30 | Zeneca Limited | Piperazinonephenyloxazolidinone derivatives and their use as antibacterial agents |
| US6271383B1 (en) | 1996-02-24 | 2001-08-07 | Zeneca Limited | Antibiotic oxazolidinone derivatives |
| US6638955B2 (en) | 1996-02-24 | 2003-10-28 | Syngenta Limited | Antibiotic oxazolidinone derivatives |
| US6110936A (en) * | 1996-05-11 | 2000-08-29 | Zeneca Limited | 3-phenyl-furan-(5H)-2-one and dihydrofuran-2-one derivatives as antibacterial agents |
| US6350775B1 (en) | 1996-05-11 | 2002-02-26 | Zeneca Limited | 3-phenyl-furan-(5H)-2-one and dihydrofuran-2-one derivatives as antibacterial agents |
| US6194441B1 (en) | 1997-08-22 | 2001-02-27 | Zeneca Ltd. | Oxazolidinone derivatives and their use as antibacterial agents |
| US6605630B1 (en) | 1997-08-22 | 2003-08-12 | Syngenta Limited | Antibiotic oxazolidinone derivatives |
| US6495551B1 (en) | 1997-11-29 | 2002-12-17 | Michael John Betts | Substituted phenyloxazolidinones and their use as antibiotics |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0261465B2 (en, 2012) | 1990-12-20 |
| ES520180A0 (es) | 1983-12-01 |
| SE8201145L (sv) | 1982-08-26 |
| NL8200732A (nl) | 1982-09-16 |
| LU83963A1 (fr) | 1983-09-02 |
| BE892270A (fr) | 1982-08-25 |
| IT8219730A0 (it) | 1982-02-18 |
| ES8306707A1 (es) | 1983-06-16 |
| GB2141716B (en) | 1985-08-29 |
| ES509848A0 (es) | 1983-06-16 |
| AU8075682A (en) | 1982-09-02 |
| US4476136A (en) | 1984-10-09 |
| ES8400729A1 (es) | 1983-12-01 |
| CA1178594A (en) | 1984-11-27 |
| AU553462B2 (en) | 1986-07-17 |
| DE3206770A1 (de) | 1982-11-11 |
| SE457258B (sv) | 1988-12-12 |
| JPS5838273A (ja) | 1983-03-05 |
| FR2500450B1 (en, 2012) | 1983-12-02 |
| CH653999A5 (fr) | 1986-01-31 |
| GB8417905D0 (en) | 1984-08-15 |
| GB2094299B (en) | 1985-08-21 |
| GB2094299A (en) | 1982-09-15 |
| GB2141716A (en) | 1985-01-03 |
| IT1153437B (it) | 1987-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |