CH555845A - Verfahren zur herstellung von oxazolidinonen und deren verwendung. - Google Patents

Verfahren zur herstellung von oxazolidinonen und deren verwendung.

Info

Publication number: CH555845A
Authority: CH; Switzerland
Prior art keywords: oxazolidinone; methyl; compounds; formula; ethyl
Prior art date: 1966-06-13

Application number

CH764267A

Other languages

German (de)

English (en)

Original Assignee

Robins Co Inc A H

Priority date (The priority date 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 date listed.)

1966-06-13

Filing date

1967-05-30

Publication date

1974-11-15

1967-05-30 Application filed by Robins Co Inc A H filed Critical Robins Co Inc A H

1974-11-15 Publication of CH555845A publication Critical patent/CH555845A/de

Links

150000001875 compounds Chemical class 0.000 claims abstract description 115
239000002253 acid Substances 0.000 claims abstract description 52
239000000203 mixture Substances 0.000 claims abstract description 38
150000003839 salts Chemical class 0.000 claims abstract description 38
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 67
-1 3-Methyl-5- {2- [4- (3-trifluoromethylphenyl) -4-hydroxypiperidinyl] ethyl} -2-oxazolidinone hydrochloride Chemical compound 0.000 claims description 55
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 49
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 46
238000000034 method Methods 0.000 claims description 42
239000000047 product Substances 0.000 claims description 35
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
239000007858 starting material Substances 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
238000002844 melting Methods 0.000 claims description 20
230000008018 melting Effects 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 20
230000008569 process Effects 0.000 claims description 20
238000004458 analytical method Methods 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 18
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
238000001953 recrystallisation Methods 0.000 claims description 15
150000001412 amines Chemical class 0.000 claims description 14
239000000706 filtrate Substances 0.000 claims description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 13
LRNOHFSJYTYVGW-UHFFFAOYSA-N 5-(2-chloroethyl)-3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CC(CCCl)OC1=O LRNOHFSJYTYVGW-UHFFFAOYSA-N 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000004663 dialkyl amino group Chemical group 0.000 claims description 11
239000000155 melt Substances 0.000 claims description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
229910052943 magnesium sulfate Inorganic materials 0.000 claims description 9
235000019341 magnesium sulphate Nutrition 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
239000007795 chemical reaction product Substances 0.000 claims description 7
239000000284 extract Substances 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
239000012299 nitrogen atmosphere Substances 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
239000000538 analytical sample Substances 0.000 claims description 5
238000002425 crystallisation Methods 0.000 claims description 5
230000008025 crystallization Effects 0.000 claims description 5
239000000463 material Substances 0.000 claims description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 3
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
239000000523 sample Substances 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
238000004809 thin layer chromatography Methods 0.000 claims description 3
FPTKDIBNZLSEFE-UHFFFAOYSA-N 4-(4-methoxyphenyl)piperidin-4-ol;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1(O)CCNCC1 FPTKDIBNZLSEFE-UHFFFAOYSA-N 0.000 claims description 2
SBKPKQORDCJPSQ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]piperidin-4-ol;hydrochloride Chemical compound Cl.C=1C=CC(C(F)(F)F)=CC=1C1(O)CCNCC1 SBKPKQORDCJPSQ-UHFFFAOYSA-N 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 2
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
239000002026 chloroform extract Substances 0.000 claims description 2
238000004587 chromatography analysis Methods 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
238000000605 extraction Methods 0.000 claims description 2
238000001640 fractional crystallisation Methods 0.000 claims description 2
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims description 2
239000000391 magnesium silicate Substances 0.000 claims description 2
229910052919 magnesium silicate Inorganic materials 0.000 claims description 2
235000019792 magnesium silicate Nutrition 0.000 claims description 2
239000012452 mother liquor Substances 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 claims description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
125000004429 atom Chemical group 0.000 abstract 1
238000009472 formulation Methods 0.000 abstract 1
239000000243 solution Substances 0.000 description 29
239000003921 oil Substances 0.000 description 23
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 21
238000003756 stirring Methods 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
230000018044 dehydration Effects 0.000 description 14
238000006297 dehydration reaction Methods 0.000 description 14
150000003254 radicals Chemical class 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
239000007787 solid Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
GKEPFKCRSLWTLE-UHFFFAOYSA-N 5-(2-chloroethyl)-1,3-oxazolidin-2-one Chemical compound ClCCC1CNC(=O)O1 GKEPFKCRSLWTLE-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
229910052736 halogen Inorganic materials 0.000 description 9
150000002367 halogens Chemical class 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
239000012458 free base Substances 0.000 description 8
OMPXTQYWYRWWPH-UHFFFAOYSA-N 4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1NCCC(C=2C=CC=CC=2)=C1 OMPXTQYWYRWWPH-UHFFFAOYSA-N 0.000 description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
150000007513 acids Chemical class 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
229940125723 sedative agent Drugs 0.000 description 6
239000000932 sedative agent Substances 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
238000009835 boiling Methods 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 5
239000000725 suspension Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000012071 phase Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
LPLAYPUVAYUNJA-UHFFFAOYSA-N 3-benzyl-5-(2-chloroethyl)-1,3-oxazolidin-2-one Chemical compound O=C1OC(CCCl)CN1CC1=CC=CC=C1 LPLAYPUVAYUNJA-UHFFFAOYSA-N 0.000 description 3
PSPCRAWZJDRVAW-UHFFFAOYSA-N 3-benzyl-5-(3-chloropropyl)-1,3-oxazolidin-2-one Chemical compound C(C1=CC=CC=C1)N1C(OC(C1)CCCCl)=O PSPCRAWZJDRVAW-UHFFFAOYSA-N 0.000 description 3
CTTBTYWBXXWBMU-UHFFFAOYSA-N 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=CCNCC1 CTTBTYWBXXWBMU-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
238000004508 fractional distillation Methods 0.000 description 3
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
150000002440 hydroxy compounds Chemical class 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
238000002955 isolation Methods 0.000 description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
DIKTXJFSPMARMT-UHFFFAOYSA-N 3-benzyl-5-(3-hydroxypropyl)-1,3-oxazolidin-2-one Chemical compound C(C1=CC=CC=C1)N1C(OC(C1)CCCO)=O DIKTXJFSPMARMT-UHFFFAOYSA-N 0.000 description 2
AFQYBBFSDHKQJV-UHFFFAOYSA-N 3-phenylpyrrolidin-3-ol Chemical compound C=1C=CC=CC=1C1(O)CCNC1 AFQYBBFSDHKQJV-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
POGWXTJNUCZEPR-UHFFFAOYSA-N 4-phenyl-1,2,3,6-tetrahydropyridin-1-ium;chloride Chemical compound Cl.C1NCCC(C=2C=CC=CC=2)=C1 POGWXTJNUCZEPR-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
NPJOAZPLPUZLRF-UHFFFAOYSA-N 5-(1-chloropropan-2-yl)-1,3-oxazolidin-2-one Chemical compound CC(CCl)C1CNC(=O)O1 NPJOAZPLPUZLRF-UHFFFAOYSA-N 0.000 description 2
OQVYRNRFJKHUDI-UHFFFAOYSA-N 5-(2-chloroethyl)-3,4-dimethyl-1,3-oxazolidin-2-one Chemical compound CC1C(CCCl)OC(=O)N1C OQVYRNRFJKHUDI-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
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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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)

CH764267A 1966-06-13 1967-05-30 Verfahren zur herstellung von oxazolidinonen und deren verwendung. CH555845A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US55687266A	1966-06-13	1966-06-13
US75537068A	1968-08-26	1968-08-26

Publications (1)

Publication Number	Publication Date
CH555845A true CH555845A (de)	1974-11-15

Family

ID=27071276

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH764267A CH555845A (de)	1966-06-13	1967-05-30	Verfahren zur herstellung von oxazolidinonen und deren verwendung.

Country Status (11)

Country	Link
US (2)	US3455941A (da)
BE (1)	BE699845A (da)
CH (1)	CH555845A (da)
DE (1)	DE1695638A1 (da)
DK (1)	DK127066B (da)
ES (1)	ES341733A1 (da)
FR (1)	FR6693M (da)
GB (1)	GB1167392A (da)
IL (1)	IL28125A (da)
NL (2)	NL6708113A (da)
SE (1)	SE325576B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3856962A (en) *	1973-07-10	1974-12-24	R Alphin	Anti-inflammatory agents
US3895021A (en) *	1973-09-04	1975-07-15	Smithkline Corp	N-heterocyclic pulvinic acid amides
AU607735B2 (en) *	1987-05-07	1991-03-14	A.H. Robins Company, Incorporated	Novel cyclic carbamate derivatives
US5086055A (en) *	1990-12-24	1992-02-04	A. H. Robins Company, Incorporated	Series of 5-[-(4-aryl-1-piperazinyl)alkyl]-2-oxazolidinone derivatives useful in the treatment of allergic conditions
US5162322A (en) *	1991-03-06	1992-11-10	A. H. Robbins Company, Incorporated	Method of treating anxiety with 5-[(4-aryl or heteroaryl-1-piperazinyl]alkyl)-2-oxazolidinones
ES2111326T3 (es) *	1993-09-15	1998-03-01	Merck Sharp & Dohme	Derivados de imidazolona y oxazolona como antagonistas de dopamina.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2537854A (en) *	1949-07-08	1951-01-09	Hoffmann La Roche	Tetrahydropyridines and method of manufacture
US3085093A (en) *	1961-09-25	1963-04-09	Warner Lambert Pharmaceutical	1, 6-bis(2, 2, 6, 6-tetramethylpiperidino)-2, 4-hexadiyne
DE1210874B (de) *	1961-12-14	1966-02-17	Degussa	Verfahren zur Herstellung von Diarylaminoderivaten von Arylaminoalkanen

0
- NL NL130094D patent/NL130094C/xx active
1966
- 1966-06-13 US US556872A patent/US3455941A/en not_active Expired - Lifetime
1967
- 1967-05-30 CH CH764267A patent/CH555845A/de not_active IP Right Cessation
- 1967-06-09 NL NL6708113A patent/NL6708113A/xx unknown
- 1967-06-09 IL IL28125A patent/IL28125A/en unknown
- 1967-06-10 DE DE19671695638 patent/DE1695638A1/de active Pending
- 1967-06-12 FR FR109984A patent/FR6693M/fr not_active Expired
- 1967-06-12 DK DK304467AA patent/DK127066B/da not_active IP Right Cessation
- 1967-06-13 BE BE699845D patent/BE699845A/xx not_active IP Right Cessation
- 1967-06-13 SE SE08335/67A patent/SE325576B/xx unknown
- 1967-06-13 ES ES341733A patent/ES341733A1/es not_active Expired
- 1967-06-13 GB GB27291/67A patent/GB1167392A/en not_active Expired
1968
- 1968-08-26 US US755370A patent/US3513236A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE1695638A1 (de)	1972-03-02
DK127066B (da)	1973-09-17
BE699845A (da)	1967-11-16
US3513236A (en)	1970-05-19
US3455941A (en)	1969-07-15
NL6708113A (da)	1967-12-14
NL130094C (da)	1900-01-01
SE325576B (da)	1970-07-06
IL28125A (en)	1972-07-26
FR6693M (da)	1969-02-10
ES341733A1 (es)	1968-07-01
GB1167392A (en)	1969-10-15

Legal Events

Date	Code	Title	Description
1987-01-30	PL	Patent ceased

Publication	Publication Date	Title
DE1595915C3 (de)	1980-02-21	Pyrrolidinderivate
DE69623631T2 (de)	2003-08-07	4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridine als neurothophe und neuroprotektive wirkstoffe
DE3688827T2 (de)	1994-03-31	Piperidinderivat, seine Herstellung und seine Verwendung als Arzneimittel.
DE3001328C2 (da)	1989-06-08
DE69023928T2 (de)	1996-04-18	DIAMINVERBINDUNGEN UND ARZNEIMITTEL GEGEN CEREBRALE STöRUNGEN DIE DIESE ENTHALTEN.
DE69329894T2 (de)	2001-05-03	Arylamidderivate
DE3883387T2 (de)	1993-12-09	Bis(methylendioxy)biphenyl-Verbindungen.
DE2065636A1 (de)	1974-12-19	Neue tricyclische verbindungen
DE2807623C2 (de)	1982-07-01	2-Phenoxyphenyl-pyrrolidinderivate, deren Salze, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
CH631164A5 (de)	1982-07-30	Verfahren zur herstellung von neuem 1-cyclopropylmethyl-4-(3-jod-5h-dibenzo(a,d)cyclohepten-5-yliden)piperidin.
DE2719211C3 (de)	1982-01-07	1-(2-Phenylamino-äthyl)-4-(N-phenyl-N-propionylamino)-piperidine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2006978B2 (de)	1978-10-12	N- [H3-Trifluormethyl-phenyl)-propyl-(2)] -glycinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE69014064T2 (de)	1995-05-18	Benzopyranon-beta-D-thioxyloside, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung.
DE69119509T2 (de)	1997-01-09	Benzhydryloxyethylpiperidyl-Derivate aliphatischer Carbonsäuren und ihre Anwendung zur Behandlung von Allergien und Asthma
DE2618999C2 (de)	1985-01-03	1-{[5-(4-Hydroxy-2H-1,2-benzothiazin-3-yl)-1,2.4-oxadiazol-3-yl]methyl}-äthanon-S,S-dioxide, Verfahren zu ihrer Herstellung sowie Verfahren zu ihrer Weiterverarbeitung
DE2348973C3 (de)	1980-04-24	1 -(m-Trifluormethylphenyl)-4-propyIpiperazin-derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE69110217T2 (de)	1996-02-29	Derivate der Kaffeinsäure und sie enthaltende pharmazeutische Zusammensetzungen.
DE2017256A1 (de)	1970-10-08	l-Carbamoyl-3-pheny!pyrrolidine und Verfahren zu deren Herstellung
DE1695638A1 (de)	1972-03-02	5-[(Aryldehydropiperidyl- und Aryldehydropyrrolidyl)-niederes alkyl]-2-oxazolidinone,sowie deren Herstellung
CH610330A5 (en)	1979-04-12	Process for the preparation of novel ergopeptins
DE2907379A1 (de)	1979-09-06	Benzylidenderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2517020A1 (de)	1975-11-06	Alkanolaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2428200A1 (de)	1975-01-09	Essigsaeurederivate, verfahren zu deren herstellung und diese derivate enthaltende arzneimittel
DE1620746A1 (de)	1970-05-14	Verfahren zur Herstellung von Phenothiazin-Derivaten
CH535767A (de)	1973-04-15	Verfahren zur Herstellung neuer N-Phenäthylpiperidinderivate