TW219936B

TW219936B -

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Publication number: TW219936B
Authority: TW; Taiwan
Prior art keywords: staphylococcus aureus; group; dup; staphylococcus; methyl
Prior art date: 1988-09-15

Application number

TW078106662A

Other languages

English (en)

Chinese (zh)

Original Assignee

Upjohn Co

Priority date

1988-09-15

Filing date

1989-08-29

Publication date

1994-02-01

1989-08-29 Application filed by Upjohn Co filed Critical Upjohn Co

1994-02-01 Application granted granted Critical

1994-02-01 Publication of TW219936B publication Critical patent/TW219936B/zh

Links

-1 phenyl furanyl Chemical group 0.000 claims abstract description 125
239000000203 mixture Substances 0.000 claims description 175
150000001875 compounds Chemical class 0.000 claims description 148
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 92
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 77
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 62
150000002576 ketones Chemical class 0.000 claims description 52
239000000243 solution Substances 0.000 claims description 50
229910052757 nitrogen Inorganic materials 0.000 claims description 47
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 44
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
238000000034 method Methods 0.000 claims description 32
239000000126 substance Substances 0.000 claims description 32
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 26
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
230000000694 effects Effects 0.000 claims description 18
239000000047 product Substances 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 13
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
238000012360 testing method Methods 0.000 claims description 12
125000001041 indolyl group Chemical group 0.000 claims description 11
SPVVYMJGMJYAGT-UHFFFAOYSA-N n-[(2-oxo-1,3-oxazolidin-3-yl)methyl]acetamide Chemical compound CC(=O)NCN1CCOC1=O SPVVYMJGMJYAGT-UHFFFAOYSA-N 0.000 claims description 11
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 9
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239000010931 gold Substances 0.000 claims description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
230000000844 anti-bacterial effect Effects 0.000 claims description 8
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 6
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XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims description 3
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125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 3
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 3
RDMYFBIIMTZCFO-UHFFFAOYSA-N 3-(1h-indazol-3-yl)-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=NNC2=CC=CC=C12 RDMYFBIIMTZCFO-UHFFFAOYSA-N 0.000 claims description 2
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AKZDAUCMQWYPAF-UHFFFAOYSA-N N1C(CCCC1)=O.O1N=NC=C1 Chemical compound N1C(CCCC1)=O.O1N=NC=C1 AKZDAUCMQWYPAF-UHFFFAOYSA-N 0.000 claims description 2
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229910052802 copper Inorganic materials 0.000 claims description 2
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125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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241000191967 Staphylococcus aureus Species 0.000 claims 49
POXUJOYUVLWPQN-ZDUSSCGKSA-N n-[[(5s)-3-(4-acetylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C(C)=O)C=C1 POXUJOYUVLWPQN-ZDUSSCGKSA-N 0.000 claims 23
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241000191963 Staphylococcus epidermidis Species 0.000 claims 15
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241000607715 Serratia marcescens Species 0.000 claims 6
241000589517 Pseudomonas aeruginosa Species 0.000 claims 5
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238000011160 research Methods 0.000 claims 5
229940031000 streptococcus pneumoniae Drugs 0.000 claims 5
241000191940 Staphylococcus Species 0.000 claims 4
241000194017 Streptococcus Species 0.000 claims 4
238000003466 welding Methods 0.000 claims 4
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims 3
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 3
241000606124 Bacteroides fragilis Species 0.000 claims 3
241000588919 Citrobacter freundii Species 0.000 claims 3
238000007865 diluting Methods 0.000 claims 3
238000001243 protein synthesis Methods 0.000 claims 3
NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical compound O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 claims 3
230000014616 translation Effects 0.000 claims 3
241000894006 Bacteria Species 0.000 claims 2
101100234547 Caenorhabditis elegans rod-1 gene Proteins 0.000 claims 2
241000588923 Citrobacter Species 0.000 claims 2
241000588697 Enterobacter cloacae Species 0.000 claims 2
241000186781 Listeria Species 0.000 claims 2
241000589516 Pseudomonas Species 0.000 claims 2
241001221452 Staphylococcus faecalis Species 0.000 claims 2
241001147691 Staphylococcus saprophyticus Species 0.000 claims 2
241000193996 Streptococcus pyogenes Species 0.000 claims 2
108010059993 Vancomycin Proteins 0.000 claims 2
230000001580 bacterial effect Effects 0.000 claims 2
238000001727 in vivo Methods 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
210000004072 lung Anatomy 0.000 claims 2
RYTTWOVTZKVWTO-ZOZMEPSFSA-N n-[[(5s)-3-(4-methylsulfinylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(S(C)=O)C=C1 RYTTWOVTZKVWTO-ZOZMEPSFSA-N 0.000 claims 2
MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 claims 2
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JJSQUEBGFNRLKO-UHFFFAOYSA-N 1h-indol-1-ium;methanesulfonate Chemical compound CS(O)(=O)=O.C1=CC=C2NC=CC2=C1 JJSQUEBGFNRLKO-UHFFFAOYSA-N 0.000 claims 1
YORKCBORGGOPFM-UHFFFAOYSA-N 1h-pyrazole;1h-pyridin-2-one Chemical compound C=1C=NNC=1.O=C1C=CC=CN1 YORKCBORGGOPFM-UHFFFAOYSA-N 0.000 claims 1
FQJRFSYYZAPSAU-UHFFFAOYSA-N 2,3-dihydroindole-1-sulfonic acid Chemical compound C1=CC=C2N(S(=O)(=O)O)CCC2=C1 FQJRFSYYZAPSAU-UHFFFAOYSA-N 0.000 claims 1
GUTWSYDQTBWGNK-UHFFFAOYSA-N 2-(1H-indol-2-yl)-1,3-oxazolidine Chemical compound N1C(=CC2=CC=CC=C12)C1OCCN1 GUTWSYDQTBWGNK-UHFFFAOYSA-N 0.000 claims 1
DOBIZWYVJFIYOV-UHFFFAOYSA-N 7-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(O)=CC=C21 DOBIZWYVJFIYOV-UHFFFAOYSA-N 0.000 claims 1
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