SK50096A3 - Benzocyclopentanoxyzolidinones which contains hetero-atom, process for producing them, their use and pharmaceutical composition containing these substances - Google Patents

Benzocyclopentanoxyzolidinones which contains hetero-atom, process for producing them, their use and pharmaceutical composition containing these substances Download PDF

Info

Publication number: SK50096A3
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; straight; formula; different
Prior art date: 1995-04-21

Application number

SK500-96A

Other languages

English (en)

Slovak (sk)

Inventor

Andreas Stolle

Dieter Haebich

Stephan Bartel

Bernd Riedl

Martin Ruppelt

Hanno Wild

Rainer Endermann

Klaus-Dieter Bremm

Hein-Peter Kroll

Harald Labischinski

Klaus Schaller

Hans-Otto Werling

Original Assignee

Bayer Ag

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.)

1995-04-21

Filing date

1996-04-19

Publication date

1997-05-07

1995-11-27 Priority claimed from DE19544106A external-priority patent/DE19544106A1/de

1996-04-19 Application filed by Bayer Ag filed Critical Bayer Ag

1997-05-07 Publication of SK50096A3 publication Critical patent/SK50096A3/sk

Links

125000005842 heteroatom Chemical group 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims description 27
239000000126 substance Substances 0.000 title description 5
239000008194 pharmaceutical composition Substances 0.000 title description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 79
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 65
-1 NHSO2R Chemical group 0.000 claims abstract description 50
229910052717 sulfur Inorganic materials 0.000 claims abstract description 28
125000002252 acyl group Chemical group 0.000 claims abstract description 23
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 22
125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 15
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
125000003944 tolyl group Chemical group 0.000 claims abstract description 13
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 7
125000004001 thioalkyl group Chemical group 0.000 claims abstract description 7
125000005843 halogen group Chemical group 0.000 claims abstract description 5
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 161
125000004432 carbon atom Chemical group C* 0.000 claims description 124
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 119
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 89
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 63
229910052739 hydrogen Inorganic materials 0.000 claims description 59
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 28
239000000460 chlorine Substances 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 26
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
239000012442 inert solvent Substances 0.000 claims description 22
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
229910052801 chlorine Inorganic materials 0.000 claims description 18
125000004434 sulfur atom Chemical group 0.000 claims description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
125000004430 oxygen atom Chemical group O* 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000006239 protecting group Chemical group 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 12
150000001298 alcohols Chemical class 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 12
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
150000007513 acids Chemical class 0.000 claims description 11
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 9
238000007127 saponification reaction Methods 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
229910052721 tungsten Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
238000007796 conventional method Methods 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
230000029936 alkylation Effects 0.000 claims description 6
238000005804 alkylation reaction Methods 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
238000007363 ring formation reaction Methods 0.000 claims description 6
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 6
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
150000001540 azides Chemical class 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 4
KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical group [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 4
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 4
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 4
238000005886 esterification reaction Methods 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000005936 piperidyl group Chemical group 0.000 claims description 4
239000002671 adjuvant Substances 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 3
150000001351 alkyl iodides Chemical class 0.000 claims description 3
ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical compound OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
150000001805 chlorine compounds Chemical class 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
238000006479 redox reaction Methods 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
238000001149 thermolysis Methods 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
125000001725 pyrenyl group Chemical group 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
229910052720 vanadium Inorganic materials 0.000 claims description 2
150000002118 epoxides Chemical class 0.000 claims 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
125000001246 bromo group Chemical group Br* 0.000 claims 1
229920001577 copolymer Chemical group 0.000 claims 1
238000010511 deprotection reaction Methods 0.000 claims 1
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims 1
125000002346 iodo group Chemical group I* 0.000 claims 1
229910002091 carbon monoxide Inorganic materials 0.000 abstract description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
125000006163 5-membered heteroaryl group Chemical group 0.000 abstract 1
101100134925 Gallus gallus COR6 gene Proteins 0.000 abstract 1
101150020251 NR13 gene Proteins 0.000 abstract 1
229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 abstract 1
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 110
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 57
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
239000000243 solution Substances 0.000 description 40
239000002904 solvent Substances 0.000 description 37
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
238000005160 1H NMR spectroscopy Methods 0.000 description 33
235000019441 ethanol Nutrition 0.000 description 31
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
239000011541 reaction mixture Substances 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
229910052799 carbon Inorganic materials 0.000 description 23
239000000203 mixture Substances 0.000 description 23
239000002244 precipitate Substances 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical compound C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 description 20
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 20
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 18
239000002585 base Substances 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
150000002431 hydrogen Chemical class 0.000 description 11
238000010992 reflux Methods 0.000 description 11
239000012074 organic phase Substances 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 8
239000007858 starting material Substances 0.000 description 8
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
239000008096 xylene Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
230000010933 acylation Effects 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 6
150000008282 halocarbons Chemical class 0.000 description 6
239000005457 ice water Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
YTSRSHZBPTWWPQ-YBTMIULGSA-N N-[[(5S)-3-(3-methyl-2-methylsulfanyl-2H-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide hydroiodide Chemical compound I.C=1C=C2N(C)C(SC)SC2=CC=1N1C[C@H](CNC(C)=O)OC1=O YTSRSHZBPTWWPQ-YBTMIULGSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
230000009435 amidation Effects 0.000 description 5
238000007112 amidation reaction Methods 0.000 description 5
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 5
229910052744 lithium Inorganic materials 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
230000009467 reduction Effects 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
BPXSNWOACLQLLY-QRPNPIFTSA-N (5s)-5-(aminomethyl)-3-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-1,3-oxazolidin-2-one;hydrochloride Chemical compound Cl.C1=C2SC(=O)N(C)C2=CC=C1N1C[C@H](CN)OC1=O BPXSNWOACLQLLY-QRPNPIFTSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
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239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
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XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
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150000003869 acetamides Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
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229910000102 alkali metal hydride Inorganic materials 0.000 description 1
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150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
ATVVHUOUPURNSX-UHFFFAOYSA-N benzyl n-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)carbamate Chemical compound C1=C2SC(=O)N(C)C2=CC=C1NC(=O)OCC1=CC=CC=C1 ATVVHUOUPURNSX-UHFFFAOYSA-N 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
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150000001718 carbodiimides Chemical class 0.000 description 1
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239000007795 chemical reaction product Substances 0.000 description 1
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239000000470 constituent Substances 0.000 description 1
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238000000354 decomposition reaction Methods 0.000 description 1
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UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
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239000003937 drug carrier Substances 0.000 description 1
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230000000694 effects Effects 0.000 description 1
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229940047650 haemophilus influenzae Drugs 0.000 description 1
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238000005658 halogenation reaction Methods 0.000 description 1
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238000007327 hydrogenolysis reaction Methods 0.000 description 1
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
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HPSFKDOGSINCBK-NSHDSACASA-N n-[[(5s)-3-(3-ethyl-2-oxo-1h-benzimidazol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C=C2NC(=O)N(CC)C2=CC=1N1C[C@H](CNC(C)=O)OC1=O HPSFKDOGSINCBK-NSHDSACASA-N 0.000 description 1
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XSWONDWTMHPWDY-NSHDSACASA-N n-[[(5s)-3-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]cyclopropanecarboxamide Chemical compound C([C@H]1CN(C(O1)=O)C1=CC=C2N(C(SC2=C1)=O)C)NC(=O)C1CC1 XSWONDWTMHPWDY-NSHDSACASA-N 0.000 description 1
APLLIOGENPXINE-JTQLQIEISA-N n-[[(5s)-3-[3-(hydroxymethyl)-2-oxo-1,3-benzothiazol-6-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N(CO)C(=O)S2)C2=C1 APLLIOGENPXINE-JTQLQIEISA-N 0.000 description 1
ULPARROWLACLIQ-LBPRGKRZSA-N n-[[(5s)-3-[3-hydroxy-4-(propan-2-ylamino)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1=C(O)C(NC(C)C)=CC=C1N1C(=O)O[C@@H](CNC(C)=O)C1 ULPARROWLACLIQ-LBPRGKRZSA-N 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
HJKYXKSLRZKNSI-UHFFFAOYSA-I pentapotassium;hydrogen sulfate;oxido sulfate;sulfuric acid Chemical compound [K+].[K+].[K+].[K+].[K+].OS([O-])(=O)=O.[O-]S([O-])(=O)=O.OS(=O)(=O)O[O-].OS(=O)(=O)O[O-] HJKYXKSLRZKNSI-UHFFFAOYSA-I 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000010626 work up procedure Methods 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
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Oncology (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK500-96A 1995-04-21 1996-04-19 Benzocyclopentanoxyzolidinones which contains hetero-atom, process for producing them, their use and pharmaceutical composition containing these substances SK50096A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19514769		1995-04-21
DE19544106A DE19544106A1 (de)	1995-04-21	1995-11-27	Heteroatomhaltige Benzocyclopentanoxazolidinone

Publications (1)

Publication Number	Publication Date
SK50096A3 true SK50096A3 (en)	1997-05-07

Family

ID=26014539

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK500-96A SK50096A3 (en)	1995-04-21	1996-04-19	Benzocyclopentanoxyzolidinones which contains hetero-atom, process for producing them, their use and pharmaceutical composition containing these substances

Country Status (21)

Country	Link
US (1)	US6069160A (fr)
EP (1)	EP0738726B1 (fr)
JP (1)	JP3967401B2 (fr)
CN (1)	CN1138582A (fr)
AT (1)	ATE206120T1 (fr)
AU (1)	AU705071B2 (fr)
BG (1)	BG100525A (fr)
CA (1)	CA2174473A1 (fr)
CZ (1)	CZ114296A3 (fr)
EE (1)	EE9600043A (fr)
ES (1)	ES2164182T3 (fr)
HR (1)	HRP960159A2 (fr)
HU (1)	HUP9601001A3 (fr)
IL (1)	IL117954A0 (fr)
MA (1)	MA23845A1 (fr)
MX (1)	MX9601399A (fr)
NO (1)	NO305909B1 (fr)
NZ (1)	NZ286400A (fr)
SG (1)	SG52774A1 (fr)
SK (1)	SK50096A3 (fr)
TR (1)	TR199600319A2 (fr)

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1996
- 1996-04-04 HR HR19544106.0A patent/HRP960159A2/hr not_active Application Discontinuation
- 1996-04-09 ES ES96105539T patent/ES2164182T3/es not_active Expired - Lifetime
- 1996-04-09 AT AT96105539T patent/ATE206120T1/de not_active IP Right Cessation
- 1996-04-09 EP EP96105539A patent/EP0738726B1/fr not_active Expired - Lifetime
- 1996-04-12 US US08/631,516 patent/US6069160A/en not_active Expired - Fee Related
- 1996-04-15 MX MX9601399A patent/MX9601399A/es unknown
- 1996-04-16 JP JP11711796A patent/JP3967401B2/ja not_active Expired - Fee Related
- 1996-04-17 HU HU9601001A patent/HUP9601001A3/hu unknown
- 1996-04-17 TR TR96/00319A patent/TR199600319A2/xx unknown
- 1996-04-17 AU AU50735/96A patent/AU705071B2/en not_active Ceased
- 1996-04-18 IL IL11795496A patent/IL117954A0/xx unknown
- 1996-04-18 CA CA002174473A patent/CA2174473A1/fr not_active Abandoned
- 1996-04-18 NZ NZ286400A patent/NZ286400A/en unknown
- 1996-04-19 CZ CZ961142A patent/CZ114296A3/cs unknown
- 1996-04-19 SG SG1996009312A patent/SG52774A1/en unknown
- 1996-04-19 MA MA24205A patent/MA23845A1/fr unknown
- 1996-04-19 NO NO961559A patent/NO305909B1/no unknown
- 1996-04-19 BG BG100525A patent/BG100525A/xx unknown
- 1996-04-19 CN CN96106152A patent/CN1138582A/zh active Pending
- 1996-04-19 EE EE9600043A patent/EE9600043A/xx unknown
- 1996-04-19 SK SK500-96A patent/SK50096A3/sk unknown

Also Published As

Publication number	Publication date
HU9601001D0 (en)	1996-06-28
EP0738726B1 (fr)	2001-09-26
SG52774A1 (en)	1998-09-28
IL117954A0 (en)	1996-08-04
TR199600319A2 (tr)	1996-11-21
HUP9601001A2 (hu)	1998-04-28
AU705071B2 (en)	1999-05-13
JP3967401B2 (ja)	2007-08-29
ATE206120T1 (de)	2001-10-15
HUP9601001A3 (en)	1999-03-01
HRP960159A2 (en)	1997-08-31
JPH08301869A (ja)	1996-11-19
CZ114296A3 (en)	1997-07-16
NO961559L (no)	1996-10-22
MA23845A1 (fr)	1996-12-31
CA2174473A1 (fr)	1996-10-22
BG100525A (en)	1997-03-31
CN1138582A (zh)	1996-12-25
US6069160A (en)	2000-05-30
MX9601399A (es)	1997-04-30
EE9600043A (et)	1996-12-16
NZ286400A (en)	1998-04-27
ES2164182T3 (es)	2002-02-16
NO305909B1 (no)	1999-08-16
NO961559D0 (no)	1996-04-19
AU5073596A (en)	1996-10-31
EP0738726A1 (fr)	1996-10-23

Publication	Publication Date	Title
SK50096A3 (en)	1997-05-07	Benzocyclopentanoxyzolidinones which contains hetero-atom, process for producing them, their use and pharmaceutical composition containing these substances
US5869659A (en)	1999-02-09	Heteroatom-containing cyclopentanopyridyl-oxazolidinones
AU2004299413C1 (en)	2009-07-02	Novel oxazolidinone derivatives
CZ187395A3 (en)	1996-02-14	Five-membered heteroaryl-oxazolidinones, their use and medicaments in which said compounds are comprised
US5684023A (en)	1997-11-04	Benzofuranyl -and benzothienyloxazolidinones
MXPA97000886A (en)	1998-04-01	New oxazolidinones sustitui
RO115263B1 (ro)	1999-12-30	Benzoxazolil- si benztiazoliloxazolidinone, procedeu pentru prepararea acestora si compozitie farmaceutica, antibacteriana
SK15897A3 (en)	1997-10-08	Substituted oxazolidinones, process for producing them, their use and pharmaceutical composition containing these substances
CZ12997A3 (en)	1997-08-13	Pyrido-annelated and thienyl- and furanyl-oxazolidinones, process of their preparation, their use and pharmaceutical composition containing thereof
MXPA97000885A (es)	1998-04-01	Nuevas heteroariloxazolidinonas
CZ34197A3 (en)	1997-08-13	Heteroaryl-oxazolidinones, process of their preparation, their use and pharmaceutical composition containing thereof
MXPA97000388A (en)	1997-12-01	Ciclopentanopiridil-oxazolidinones that containheteroate
DE19544106A1 (de)	1996-10-24	Heteroatomhaltige Benzocyclopentanoxazolidinone