NO309478B1 - Fenyloksazolidinon-antimikrobielle midler - Google Patents

Fenyloksazolidinon-antimikrobielle midler Download PDF

Info

Publication number: NO309478B1
Authority: NO; Norway
Prior art keywords: mmol; treated; methanol; solution; give
Prior art date: 1994-10-26

Application number

NO971946A

Other languages

English (en)

Norwegian (no)

Other versions

NO971946L (no

NO971946D0 (no

Inventor

Douglas K Hutchinson

Michael Robert Barbachyn

Mikio Taniguchi

Kiyotaka Munesada

Hiroyoshi Yamada

Steven J Brickner

Original Assignee

Upjohn Co

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.)

1994-10-26

Filing date

1997-04-25

Publication date

2001-02-05

1997-04-25 Application filed by Upjohn Co filed Critical Upjohn Co

1997-04-25 Publication of NO971946D0 publication Critical patent/NO971946D0/no

1997-06-25 Publication of NO971946L publication Critical patent/NO971946L/no

2001-02-05 Publication of NO309478B1 publication Critical patent/NO309478B1/no

Links

239000004599 antimicrobial Substances 0.000 title abstract description 6
NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 154
150000003839 salts Chemical class 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 87
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
208000015181 infectious disease Diseases 0.000 claims description 2
230000000813 microbial effect Effects 0.000 claims description 2
239000003814 drug Substances 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
241001112696 Clostridia Species 0.000 abstract description 4
241000187479 Mycobacterium tuberculosis Species 0.000 abstract description 4
241000295644 Staphylococcaceae Species 0.000 abstract description 4
241000894007 species Species 0.000 abstract description 4
241000894006 Bacteria Species 0.000 abstract description 3
241000192125 Firmicutes Species 0.000 abstract description 3
244000052769 pathogen Species 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 306
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 252
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 181
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 134
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 123
239000000243 solution Substances 0.000 description 117
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 94
239000011541 reaction mixture Substances 0.000 description 89
239000000203 mixture Substances 0.000 description 87
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
239000007787 solid Substances 0.000 description 81
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 77
238000006243 chemical reaction Methods 0.000 description 76
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
230000002829 reductive effect Effects 0.000 description 64
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 61
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
239000000741 silica gel Substances 0.000 description 56
229910002027 silica gel Inorganic materials 0.000 description 56
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 51
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
239000002904 solvent Substances 0.000 description 46
238000004458 analytical method Methods 0.000 description 44
238000000034 method Methods 0.000 description 42
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
229910052938 sodium sulfate Inorganic materials 0.000 description 38
235000011152 sodium sulphate Nutrition 0.000 description 38
-1 heteroaryl phenyloxazolidinones Chemical class 0.000 description 35
238000004587 chromatography analysis Methods 0.000 description 31
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
239000012267 brine Substances 0.000 description 30
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 29
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
238000005481 NMR spectroscopy Methods 0.000 description 29
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 28
239000000706 filtrate Substances 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
239000002585 base Substances 0.000 description 26
239000011734 sodium Substances 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
239000012044 organic layer Substances 0.000 description 25
239000003054 catalyst Substances 0.000 description 24
238000003756 stirring Methods 0.000 description 23
239000003921 oil Substances 0.000 description 21
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 20
238000001816 cooling Methods 0.000 description 20
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 20
229910052757 nitrogen Inorganic materials 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
229920006395 saturated elastomer Polymers 0.000 description 20
150000001412 amines Chemical class 0.000 description 17
239000003242 anti bacterial agent Substances 0.000 description 17
239000000463 material Substances 0.000 description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 16
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 15
239000012359 Methanesulfonyl chloride Substances 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000543 intermediate Substances 0.000 description 15
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 15
GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 14
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
239000000284 extract Substances 0.000 description 14
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 14
125000006239 protecting group Chemical group 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 12
150000001540 azides Chemical class 0.000 description 12
238000010828 elution Methods 0.000 description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
238000010992 reflux Methods 0.000 description 12
230000000844 anti-bacterial effect Effects 0.000 description 11
239000012298 atmosphere Substances 0.000 description 11
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 11
238000005984 hydrogenation reaction Methods 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
238000001035 drying Methods 0.000 description 10
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 10
238000006722 reduction reaction Methods 0.000 description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
229960001760 dimethyl sulfoxide Drugs 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
125000002252 acyl group Chemical group 0.000 description 8
150000001448 anilines Chemical class 0.000 description 8
229940111685 dibasic potassium phosphate Drugs 0.000 description 8
238000000605 extraction Methods 0.000 description 8
238000011049 filling Methods 0.000 description 8
238000007327 hydrogenolysis reaction Methods 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000007858 starting material Substances 0.000 description 8
RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
239000000538 analytical sample Substances 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
125000000719 pyrrolidinyl group Chemical group 0.000 description 7
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
239000012065 filter cake Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
125000000547 substituted alkyl group Chemical group 0.000 description 6
239000006188 syrup Substances 0.000 description 6
235000020357 syrup Nutrition 0.000 description 6
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
239000007868 Raney catalyst Substances 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
239000006260 foam Substances 0.000 description 5
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 5
230000004048 modification Effects 0.000 description 5
238000012986 modification Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
150000003141 primary amines Chemical class 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
238000010792 warming Methods 0.000 description 5
BGKABGGFJSTLIL-UHFFFAOYSA-N 3-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical class OCN1CCOC1=O BGKABGGFJSTLIL-UHFFFAOYSA-N 0.000 description 4
YXOYOPPWBOGULQ-UHFFFAOYSA-N 3-phenyl-4-pyrrolidin-1-yl-1,3-oxazolidin-2-one Chemical class C=1C=CC=CC=1N1C(=O)OCC1N1CCCC1 YXOYOPPWBOGULQ-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
125000002393 azetidinyl group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
238000001914 filtration Methods 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
150000005181 nitrobenzenes Chemical class 0.000 description 4
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 3
HUHZAMBLEKHDBP-UHFFFAOYSA-N 5-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCC1CNC(=O)O1 HUHZAMBLEKHDBP-UHFFFAOYSA-N 0.000 description 3
LSYOFPBORRARMF-UHFFFAOYSA-N 5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical class OCC1CNC(=O)O1 LSYOFPBORRARMF-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 3
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
WCPHPMASJFEPFP-UHFFFAOYSA-N 4-(azetidin-1-yl)-4-hydroxy-3-phenyl-1,3-oxazolidin-2-one Chemical compound C1CCN1C1(O)COC(=O)N1C1=CC=CC=C1 WCPHPMASJFEPFP-UHFFFAOYSA-N 0.000 description 1
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241001148536 Bacteroides sp. Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000186359 Mycobacterium Species 0.000 description 1
241000186367 Mycobacterium avium Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
241000193998 Streptococcus pneumoniae Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000748245 Villanova Species 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000003869 acetamides Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
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238000005917 acylation reaction Methods 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
241001148470 aerobic bacillus Species 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
238000009635 antibiotic susceptibility testing Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
FDPKMJDUXJFKOI-UHFFFAOYSA-N azetidin-3-amine Chemical class NC1CNC1 FDPKMJDUXJFKOI-UHFFFAOYSA-N 0.000 description 1
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VMAXJDJIFGIBGH-UHFFFAOYSA-N azetidin-3-ylmethanamine Chemical compound NCC1CNC1 VMAXJDJIFGIBGH-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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FAQYQZVDJQCSCM-UHFFFAOYSA-N benzyl n-[4-[3-[tert-butyl(dimethyl)silyl]oxy-3-methylazetidin-1-yl]-3-fluorophenyl]carbamate Chemical compound C1C(O[Si](C)(C)C(C)(C)C)(C)CN1C(C(=C1)F)=CC=C1NC(=O)OCC1=CC=CC=C1 FAQYQZVDJQCSCM-UHFFFAOYSA-N 0.000 description 1
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230000003197 catalytic effect Effects 0.000 description 1
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HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
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238000000354 decomposition reaction Methods 0.000 description 1
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CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
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150000004678 hydrides Chemical class 0.000 description 1
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230000002401 inhibitory effect Effects 0.000 description 1
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MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
CTIFDBSJHUGEON-UHFFFAOYSA-N n-(2-fluoroethyl)-1-(2-fluoro-4-nitrophenyl)-n-methylazetidin-3-amine Chemical compound C1C(N(CCF)C)CN1C1=CC=C([N+]([O-])=O)C=C1F CTIFDBSJHUGEON-UHFFFAOYSA-N 0.000 description 1
IGBNXUZJNUEHGG-PYMCNQPYSA-N n-[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]pyrrolidin-3-yl]-2-hydroxyacetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC(NC(=O)CO)CC1 IGBNXUZJNUEHGG-PYMCNQPYSA-N 0.000 description 1
LIHOLEQEAIFLCI-QWAKEFERSA-N n-[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]pyrrolidin-3-yl]-2-phenylmethoxyacetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC(NC(=O)COCC=2C=CC=CC=2)CC1 LIHOLEQEAIFLCI-QWAKEFERSA-N 0.000 description 1
CNQWNQZBQYYILF-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC(O)C1 CNQWNQZBQYYILF-LBPRGKRZSA-N 0.000 description 1
GXOCFYPKUOCHAZ-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(3-oxoazetidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC(=O)C1 GXOCFYPKUOCHAZ-LBPRGKRZSA-N 0.000 description 1
IIBIPDSLMZYNEV-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-(3-oxopyrrolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC(=O)CC1 IIBIPDSLMZYNEV-ZDUSSCGKSA-N 0.000 description 1
OUXTXVBVAITFOL-KRWDZBQOSA-N n-[[(5s)-3-[4-[3-[tert-butyl(dimethyl)silyl]oxy-3-methylazetidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC(C)(O[Si](C)(C)C(C)(C)C)C1 OUXTXVBVAITFOL-KRWDZBQOSA-N 0.000 description 1
MHZOBDKSUPUOKL-INIZCTEOSA-N n-[[(5s)-3-[4-[3-[tert-butyl(dimethyl)silyl]oxyazetidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC(O[Si](C)(C)C(C)(C)C)C1 MHZOBDKSUPUOKL-INIZCTEOSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
238000006772 olefination reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
MRTAVLDNYYEJHK-UHFFFAOYSA-M sodium;2-chloro-2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)Cl MRTAVLDNYYEJHK-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
QRMKWVNXYORDRU-DZGCQCFKSA-N tert-butyl n-[(3s,4s)-1-benzyl-4-methylpyrrolidin-3-yl]carbamate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)[C@@H](C)CN1CC1=CC=CC=C1 QRMKWVNXYORDRU-DZGCQCFKSA-N 0.000 description 1
BKITXDSDJGOXPN-JGVFFNPUSA-N tert-butyl n-[(3s,4s)-4-methylpyrrolidin-3-yl]carbamate Chemical compound C[C@H]1CNC[C@H]1NC(=O)OC(C)(C)C BKITXDSDJGOXPN-JGVFFNPUSA-N 0.000 description 1
GQSCQZJQXHNUIV-UHFFFAOYSA-N tert-butyl-[1-(2-fluoro-4-nitrophenyl)-3-methylazetidin-3-yl]oxy-dimethylsilane Chemical compound C1C(O[Si](C)(C)C(C)(C)C)(C)CN1C1=CC=C([N+]([O-])=O)C=C1F GQSCQZJQXHNUIV-UHFFFAOYSA-N 0.000 description 1
CTAWTJKKRQBYAP-UHFFFAOYSA-N tert-butyl-[1-(2-fluoro-4-nitrophenyl)azetidin-3-yl]oxy-dimethylsilane Chemical compound C1C(O[Si](C)(C)C(C)(C)C)CN1C1=CC=C([N+]([O-])=O)C=C1F CTAWTJKKRQBYAP-UHFFFAOYSA-N 0.000 description 1
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- 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
- C07D413/10—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 linked by a carbon chain containing aromatic rings
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- 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

Landscapes

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

NO971946A 1994-10-26 1997-04-25 Fenyloksazolidinon-antimikrobielle midler NO309478B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US32971794A	1994-10-26	1994-10-26
PCT/US1995/010992 WO1996013502A1 (en)	1994-10-26	1995-09-12	Phenyloxazolidinone antimicrobials

Publications (3)

Publication Number	Publication Date
NO971946D0 NO971946D0 (no)	1997-04-25
NO971946L NO971946L (no)	1997-06-25
NO309478B1 true NO309478B1 (no)	2001-02-05

Family

ID=23286694

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO971946A NO309478B1 (no)	1994-10-26	1997-04-25	Fenyloksazolidinon-antimikrobielle midler

Country Status (22)

Country	Link
EP (1)	EP0788498B1 (de)
JP (1)	JP3933198B2 (de)
KR (1)	KR100383403B1 (de)
CN (1)	CN1068325C (de)
AT (1)	ATE204277T1 (de)
AU (1)	AU694271B2 (de)
BR (1)	BR9509136A (de)
CA (1)	CA2200433C (de)
CZ (1)	CZ291847B6 (de)
DE (1)	DE69522234T2 (de)
DK (1)	DK0788498T3 (de)
ES (1)	ES2162941T3 (de)
FI (1)	FI971774A7 (de)
HU (1)	HU224044B1 (de)
NO (1)	NO309478B1 (de)
NZ (1)	NZ293741A (de)
PL (1)	PL183512B1 (de)
PT (1)	PT788498E (de)
RU (1)	RU2134692C1 (de)
SI (1)	SI0788498T1 (de)
SK (1)	SK282869B6 (de)
WO (1)	WO1996013502A1 (de)

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AR038536A1 (es)	2002-02-25	2005-01-19	Upjohn Co	N-aril-2-oxazolidinona-5- carboxamidas y sus derivados
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CA2614105A1 (en) *	2005-07-06	2007-01-11	Pharmacia & Upjohn Company Llc	Oxazolidinone carboxamides containing azetidine and cyclobutane as antibacterial agents
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CN101754685B (zh)	2007-07-24	2015-09-16	陶氏环球技术公司	用于降低和抑制水基流体和与它们一起使用的系统中微生物浓度增加的方法和制剂
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EP2141162A1 (de) *	2008-07-01	2010-01-06	Ferrer Internacional, S.A.	3-(N-Heterocyclyl)-pyrrolidinyl-phenyl-oxazolidinone als antibakterielle Wirkstoffe
CN101798302B (zh) *	2009-02-06	2014-11-05	上海盟科药业有限公司	抗生素类药物1-(邻-氟苯基)二氢吡啶酮的合成及生产的方法和工艺
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1995
- 1995-09-12 DK DK95933718T patent/DK0788498T3/da active
- 1995-09-12 CN CN95195908A patent/CN1068325C/zh not_active Expired - Fee Related
- 1995-09-12 AT AT95933718T patent/ATE204277T1/de not_active IP Right Cessation
- 1995-09-12 PL PL95319873A patent/PL183512B1/pl not_active IP Right Cessation
- 1995-09-12 AU AU36254/95A patent/AU694271B2/en not_active Ceased
- 1995-09-12 SK SK494-97A patent/SK282869B6/sk unknown
- 1995-09-12 NZ NZ293741A patent/NZ293741A/en unknown
- 1995-09-12 KR KR1019970702729A patent/KR100383403B1/ko not_active Expired - Fee Related
- 1995-09-12 CZ CZ19971217A patent/CZ291847B6/cs not_active IP Right Cessation
- 1995-09-12 RU RU97108157A patent/RU2134692C1/ru not_active IP Right Cessation
- 1995-09-12 WO PCT/US1995/010992 patent/WO1996013502A1/en not_active Ceased
- 1995-09-12 HU HU9702015A patent/HU224044B1/hu not_active IP Right Cessation
- 1995-09-12 ES ES95933718T patent/ES2162941T3/es not_active Expired - Lifetime
- 1995-09-12 JP JP51454096A patent/JP3933198B2/ja not_active Expired - Fee Related
- 1995-09-12 CA CA002200433A patent/CA2200433C/en not_active Expired - Fee Related
- 1995-09-12 PT PT95933718T patent/PT788498E/pt unknown
- 1995-09-12 SI SI9530528T patent/SI0788498T1/xx unknown
- 1995-09-12 DE DE69522234T patent/DE69522234T2/de not_active Expired - Fee Related
- 1995-09-12 BR BR9509136A patent/BR9509136A/pt not_active IP Right Cessation
- 1995-09-12 EP EP95933718A patent/EP0788498B1/de not_active Expired - Lifetime
1997
- 1997-04-25 NO NO971946A patent/NO309478B1/no unknown
- 1997-04-25 FI FI971774A patent/FI971774A7/fi unknown

Also Published As

Publication number	Publication date
ATE204277T1 (de)	2001-09-15
FI971774A0 (fi)	1997-04-25
CN1068325C (zh)	2001-07-11
CA2200433A1 (en)	1996-05-09
JP3933198B2 (ja)	2007-06-20
CA2200433C (en)	2006-02-07
PL183512B1 (pl)	2002-06-28
ES2162941T3 (es)	2002-01-16
WO1996013502A1 (en)	1996-05-09
KR970707123A (ko)	1997-12-01
BR9509136A (pt)	1998-07-21
SK282869B6 (sk)	2003-01-09
JPH10508017A (ja)	1998-08-04
PT788498E (pt)	2002-02-28
NO971946L (no)	1997-06-25
HUT77602A (hu)	1998-06-29
EP0788498B1 (de)	2001-08-16
EP0788498A1 (de)	1997-08-13
HU224044B1 (hu)	2005-05-30
PL319873A1 (en)	1997-09-01
NO971946D0 (no)	1997-04-25
AU694271B2 (en)	1998-07-16
SK49497A3 (en)	1998-01-14
CZ291847B6 (cs)	2003-06-18
KR100383403B1 (ko)	2004-05-31
DE69522234T2 (de)	2002-05-16
FI971774A7 (fi)	1997-04-25
AU3625495A (en)	1996-05-23
DK0788498T3 (da)	2001-11-05
RU2134692C1 (ru)	1999-08-20
SI0788498T1 (en)	2001-12-31
CN1162312A (zh)	1997-10-15
NZ293741A (en)	1998-06-26
CZ121797A3 (en)	1997-07-16
DE69522234D1 (de)	2001-09-20

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JP3933198B2 (ja)	2007-06-20	フェニルオキサゾリジノン抗菌剤
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RU2128660C1 (ru)	1999-04-10	Бициклические оксазин- или тиазин-оксазолидиноны или их фармацевтически приемлемые соли и способы лечения микробных инфекций
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