JP2000514084A - ピリジル―ピペラジニル―フェニル―オキサゾリジノン誘導体および殺菌剤としてのその使用 - Google Patents

ピリジル―ピペラジニル―フェニル―オキサゾリジノン誘導体および殺菌剤としてのその使用

Info

Publication number: JP2000514084A
Authority: JP; Japan
Prior art keywords: formula; compound; alkyl; fluoro; phenyl
Prior art date: 1996-07-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP10504901A

Other languages

English (en)

Japanese (ja)

Inventor

ジョンベッツマイケル

ジェーンミドグレイキャサリン

Original Assignee

ゼネカ・リミテッド

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.)

1996-07-06

Filing date

1997-07-01

Publication date

2000-10-24

1997-07-01 Application filed by ゼネカ・リミテッド filed Critical ゼネカ・リミテッド

2000-10-24 Publication of JP2000514084A publication Critical patent/JP2000514084A/ja

Status Pending legal-status Critical Current

Links

239000000417 fungicide Substances 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 190
-1 carboxy, hydroxy , Amino Chemical group 0.000 claims abstract description 167
125000000217 alkyl group Chemical group 0.000 claims abstract description 112
150000003839 salts Chemical class 0.000 claims abstract description 47
150000001204 N-oxides Chemical class 0.000 claims abstract description 43
125000003545 alkoxy group Chemical group 0.000 claims abstract description 40
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
239000001257 hydrogen Substances 0.000 claims abstract description 34
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 30
150000002148 esters Chemical class 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 27
125000001424 substituent group Chemical group 0.000 claims abstract description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 24
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 20
125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 14
125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
125000004076 pyridyl group Chemical group 0.000 claims abstract description 13
238000001727 in vivo Methods 0.000 claims abstract description 11
125000005843 halogen group Chemical group 0.000 claims abstract description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 36
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 31
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
125000001309 chloro group Chemical group Cl* 0.000 claims description 16
125000006239 protecting group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
239000007858 starting material Substances 0.000 claims description 12
241001465754 Metazoa Species 0.000 claims description 11
230000000844 anti-bacterial effect Effects 0.000 claims description 11
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 11
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 10
150000001540 azides Chemical class 0.000 claims description 10
IYIGLWQQAMROOF-HHHXNRCGSA-N OSMI-1 Chemical compound COC1=C(C=CC=C1)[C@@H](NS(=O)(=O)C1=CC2=C(NC(=O)C=C2)C=C1)C(=O)N(CC1=CC=CO1)CC1=CC=CS1 IYIGLWQQAMROOF-HHHXNRCGSA-N 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
241000282412 Homo Species 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
238000010561 standard procedure Methods 0.000 claims description 5
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
230000001590 oxidative effect Effects 0.000 claims description 4
230000000845 anti-microbial effect Effects 0.000 claims description 3
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
ICCBZGUDUOMNOF-UHFFFAOYSA-N azidoamine Chemical compound NN=[N+]=[N-] ICCBZGUDUOMNOF-UHFFFAOYSA-N 0.000 claims 1
125000003963 dichloro group Chemical group Cl* 0.000 claims 1
YDSYNJAUDIUGAL-FQEVSTJZSA-N n-[[(5s)-2-oxo-3-[4-(4-pyridin-3-ylpiperazin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2CCN(CC2)C=2C=NC=CC=2)C=C1 YDSYNJAUDIUGAL-FQEVSTJZSA-N 0.000 claims 1
OXHRHWJFVQCUBR-FQEVSTJZSA-N n-[[(5s)-2-oxo-3-[4-(4-pyridin-4-ylpiperazin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2CCN(CC2)C=2C=CN=CC=2)C=C1 OXHRHWJFVQCUBR-FQEVSTJZSA-N 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 abstract description 8
238000002360 preparation method Methods 0.000 abstract description 6
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
239000000203 mixture Substances 0.000 description 47
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
239000002904 solvent Substances 0.000 description 31
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
239000000243 solution Substances 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
229910052786 argon Inorganic materials 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
239000003960 organic solvent Substances 0.000 description 12
239000000377 silicon dioxide Substances 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 11
238000010992 reflux Methods 0.000 description 11
239000007787 solid Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
244000000059 gram-positive pathogen Species 0.000 description 9
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
238000001819 mass spectrum Methods 0.000 description 8
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
239000000284 extract Substances 0.000 description 7
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
239000012267 brine Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
241000295644 Staphylococcaceae Species 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
238000001914 filtration Methods 0.000 description 5
150000002440 hydroxy compounds Chemical class 0.000 description 5
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
125000004193 piperazinyl group Chemical group 0.000 description 5
238000012360 testing method Methods 0.000 description 5
125000004149 thio group Chemical group *S* 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229920002785 Croscarmellose sodium Polymers 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 4
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
230000003115 biocidal effect Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
229960001681 croscarmellose sodium Drugs 0.000 description 4
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 4
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 4
238000010828 elution Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000008101 lactose Substances 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
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 4
238000004809 thin layer chromatography Methods 0.000 description 4
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000194032 Enterococcus faecalis Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
108010059993 Vancomycin Proteins 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
125000004849 alkoxymethyl group Chemical group 0.000 description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
125000005104 aryl silyl group Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000002054 inoculum Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000010255 intramuscular injection Methods 0.000 description 3
239000007927 intramuscular injection Substances 0.000 description 3
238000010253 intravenous injection Methods 0.000 description 3
239000010410 layer Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000010254 subcutaneous injection Methods 0.000 description 3
239000007929 subcutaneous injection Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000004665 trialkylsilyl group Chemical group 0.000 description 3
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BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
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230000015843 photosynthesis, light reaction Effects 0.000 description 1
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XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
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229920001223 polyethylene glycol Polymers 0.000 description 1
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NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 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
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125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
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QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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238000002390 rotary evaporation Methods 0.000 description 1
238000009666 routine test Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
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239000012279 sodium borohydride Substances 0.000 description 1
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BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008279 sol Substances 0.000 description 1
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YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
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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
- C07D413/12—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 chain containing hetero atoms as chain links
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP10504901A 1996-07-06 1997-07-01 ピリジル―ピペラジニル―フェニル―オキサゾリジノン誘導体および殺菌剤としてのその使用 Pending JP2000514084A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9614236.9A GB9614236D0 (en)	1996-07-06	1996-07-06	Chemical compounds
GB9614236.9		1996-07-06
PCT/GB1997/001769 WO1998001447A1 (fr)	1996-07-06	1997-07-01	Derives de pyridyle-piperazinyle-phenyle-oxazolidinone et leur utilisation en tant qu'antibacteriens

Publications (1)

Publication Number	Publication Date
JP2000514084A true JP2000514084A (ja)	2000-10-24

Family

ID=10796484

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10504901A Pending JP2000514084A (ja)	1996-07-06	1997-07-01	ピリジル―ピペラジニル―フェニル―オキサゾリジノン誘導体および殺菌剤としてのその使用

Country Status (6)

Country	Link
EP (1)	EP0918770A1 (fr)
JP (1)	JP2000514084A (fr)
AU (1)	AU3352197A (fr)
GB (1)	GB9614236D0 (fr)
WO (1)	WO1998001447A1 (fr)
ZA (1)	ZA975951B (fr)

Cited By (1)

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JP2001521025A (ja) *	1997-10-27	2001-11-06	ニューロサーチ、アクティーゼルスカブ	ニコチン性アセチルコリンレセプターに於けるコリン作動性リガンドとしてのヘテロアリールジアザシクロアルカン

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GB9609919D0 (en)	1996-05-11	1996-07-17	Zeneca Ltd	Chemical compounds
GB9717807D0 (en)	1997-08-22	1997-10-29	Zeneca Ltd	Chemical compounds
GB9717804D0 (en)	1997-08-22	1997-10-29	Zeneca Ltd	Chemical compounds
GB9725244D0 (en)	1997-11-29	1998-01-28	Zeneca Ltd	Chemical compounds
US6562844B2 (en)	1998-01-23	2003-05-13	Pharmacia & Upjohn Company	Oxazolidinone combinatorial libraries, compositions and methods of preparation
CN1288462A (zh) *	1998-01-23	2001-03-21	法玛西雅厄普约翰美国公司	噁唑烷酮组合库、组合物和制备方法
US7002020B1 (en)	1998-01-23	2006-02-21	Pharmacia & Upjohn Company	Oxazolidinone combinatorial libraries, compositions and methods of preparation
DE19905278A1 (de) *	1999-02-09	2000-08-10	Bayer Ag	Oxazolidinone und ihre Verwendung als antibakterielle Mittel
GB9928568D0 (en)	1999-12-03	2000-02-02	Zeneca Ltd	Chemical compounds
GB0009803D0 (en)	2000-04-25	2000-06-07	Astrazeneca Ab	Chemical compounds
ES2186550B2 (es) *	2001-06-27	2003-11-16	Vita Lab	Nuevos derivados de oxazolidinonas como antibacterianos.
EP1427711B1 (fr)	2001-09-11	2005-07-13	AstraZeneca AB	Oxazolidinone et/ou isoxazoline utilises comme agents antibacteriens
WO2003035073A1 (fr)	2001-10-25	2003-05-01	Astrazeneca Ab	Dérivés d'isoxazoline utilisés en tant qu'agents antimicrobiens
EP2258687B1 (fr) *	2002-02-12	2012-12-26	Glaxosmithkline LLC	Dérivés de nicotinamide utiles comme inhibiteurs de P38
BR0308018A (pt)	2002-02-28	2005-01-04	Astrazeneca Ab	Composto ou um seu sal farmaceuticamente aceitável ou um seu éster hidrolisável in vivo, pró-droga, método para produzir um efeito antibacteriano em um animal de sangue quente, uso de um composto ou um seu sal farmaceuticamente aceitável ou um seu éster hirolisável in vivo, composição farmacêutica, e, processo para a preparação de um composto ou um seu sal farmaceuticamente aceitável ou um seu éster hidrolisável in vivo
AU2003207340A1 (en)	2002-02-28	2003-09-09	Astrazeneca Ab	3-cyclyl-5-(nitrogen-containing 5-membered ring) methyl-oxazolidinone derivatives and their use as antibacterial agents
EA200401289A1 (ru) *	2002-04-01	2005-04-28	Кадила Хелзкэр Лимитед	Новые противоинфекционные соединения, способы их получения и фармацевтические композиции, содержащие эти соединения
US7217726B2 (en) *	2002-08-22	2007-05-15	Orchid Chemicals & Pharmaceuticals Limited	Antibacterial agents
WO2004026848A1 (fr)	2002-09-20	2004-04-01	Lupin Limited	Derives d'oxazolidinone, leur procede de preparation et leur utilisation comme agents antimycobacterients
WO2005051933A1 (fr) *	2003-11-28	2005-06-09	Ranbaxy Laboratories Limited	Procede ameliore de synthese d'ester test-butylique d'acide 4-(4-benzyloxy-carbonylamino-2-fluorophenyl)-piperazine-1-carboxylique, compose intermediaire cle de la preparation d'agents antimicrobiens a l'oxazolidinone, et composes ainsi prepares
DE102007004709B4 (de)	2007-01-31	2024-04-04	Schaeffler Technologies AG & Co. KG	Leichtbau-Stirnraddifferential in Dünnblechbauweise
CN101619061B (zh) *	2009-08-11	2014-12-17	沈阳药科大学	氰基吡啶基取代的噁唑烷酮类化合物

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KR100257418B1 (ko) *	1991-11-01	2000-05-15	로렌스 티. 마이젠헬더	치환된 아릴-및 헤테로아릴-페닐옥사졸리디논
SK283420B6 (sk) *	1992-05-08	2003-07-01	Pharmacia & Upjohn Company	Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny
US5652238A (en) *	1993-11-22	1997-07-29	Pharmacia & Upjohn Company	Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones

1996
- 1996-07-06 GB GBGB9614236.9A patent/GB9614236D0/en active Pending
1997
- 1997-07-01 EP EP97929405A patent/EP0918770A1/fr not_active Withdrawn
- 1997-07-01 WO PCT/GB1997/001769 patent/WO1998001447A1/fr not_active Ceased
- 1997-07-01 JP JP10504901A patent/JP2000514084A/ja active Pending
- 1997-07-01 AU AU33521/97A patent/AU3352197A/en not_active Abandoned
- 1997-07-03 ZA ZA9705951A patent/ZA975951B/xx unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001521025A (ja) *	1997-10-27	2001-11-06	ニューロサーチ、アクティーゼルスカブ	ニコチン性アセチルコリンレセプターに於けるコリン作動性リガンドとしてのヘテロアリールジアザシクロアルカン

Also Published As

Publication number	Publication date
WO1998001447A1 (fr)	1998-01-15
EP0918770A1 (fr)	1999-06-02
GB9614236D0 (en)	1996-09-04
ZA975951B (en)	1998-01-06
AU3352197A (en)	1998-02-02

Publication	Publication Date	Title
JP2000514084A (ja)	2000-10-24	ピリジル―ピペラジニル―フェニル―オキサゾリジノン誘導体および殺菌剤としてのその使用
JP2000514083A (ja)	2000-10-24	置換ピペラジニル―フェニル―オキサゾリジノン誘導体および抗菌剤としてのその利用
US6194441B1 (en)	2001-02-27	Oxazolidinone derivatives and their use as antibacterial agents
EP0882041B1 (fr)	2003-03-26	Derives de piperazinonephenyloxazolidinone et leur utilisation en tant qu'agents antibacteriens
US7192974B2 (en)	2007-03-20	Hydroxymethyl substituted dihydroisoxazole derivatives useful as antibiotic agents
US6495551B1 (en)	2002-12-17	Substituted phenyloxazolidinones and their use as antibiotics
DE60205030T2 (de)	2006-04-20	Oxazolidinon- und/oder isoxazolinderivate als antibakterielle mittel
EP1082322B1 (fr)	2004-01-28	Derives d'oxazolidinone comme antibiotiques, leur procede de preparation et compositions pharmaceutiques contenant ceux-ci
JP2903292B2 (ja)	1999-06-07	抗菌性医薬
KR100882377B1 (ko)	2009-02-05	치환된 이속사졸 및 항생제로서의 이들의 용도
US20020133022A1 (en)	2002-09-19	Antibiotic oxazolidinone derivatives
CN102164912B (zh)	2015-08-19	制备喹诺酮类化合物的工艺
DE60210654T2 (de)	2007-01-25	Aryl substituierte oxazolidinone mit antibacterieller activität
RS60662B1 (sr)	2020-09-30	Peptidni makrocikli protiv acinetobacter baumannii
WO2005005398A2 (fr)	2005-01-20	Antibiotiques a base d'oxazolidinone substituee par un groupe cyclipropyl et derives
JP2008500315A (ja)	2008-01-10	抗菌剤としての、３−［４−（６−｛４，５−ジヒドロイソオキサゾール−３−イル｝ピリジン−３−イル）−３−フェニル］−５−（１ｈ−１，２，３−トリアゾール−１−イルメチル）−１，３−オキサゾリジン−２−オン
KR100529815B1 (ko)	2005-11-22	피리도벤즈옥사진 유도체 및 이를 포함하는 항균제
JP4619952B2 (ja)	2011-01-26	８−シアノキノロンカルボン酸誘導体
HK1083097B (en)	2009-01-02	Hydroxymethyl substituted dihydroisoxazole derivatives useful as antibiotic agents
CN1989136A (zh)	2007-06-27	作为抗菌剂的3－[4－(6－{4,5－二氢异唑－3－基}吡啶－3－基)－3－苯基]－5－(1h－1,2,3－三唑－1－基－甲基)－1,3－唑烷－2－酮类

JP2000514084A - ピリジル―ピペラジニル―フェニル―オキサゾリジノン誘導体および殺菌剤としてのその使用 - Google Patents

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Publications (1)

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ID=10796484

Family Applications (1)

Country Status (6)

Cited By (1)

Families Citing this family (22)

Family Cites Families (3)

Cited By (1)

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