NO327010B1 - Oksazolidinon og/eller isoksazolin anvendelse derav som antibakterielle midler, farmasoytisk sammensetning og fremgangsmate for fremstilling derav - Google Patents
Oksazolidinon og/eller isoksazolin anvendelse derav som antibakterielle midler, farmasoytisk sammensetning og fremgangsmate for fremstilling derav Download PDFInfo
- Publication number
- NO327010B1 NO327010B1 NO20041428A NO20041428A NO327010B1 NO 327010 B1 NO327010 B1 NO 327010B1 NO 20041428 A NO20041428 A NO 20041428A NO 20041428 A NO20041428 A NO 20041428A NO 327010 B1 NO327010 B1 NO 327010B1
- Authority
- NO
- Norway
- Prior art keywords
- het
- methyl
- group
- oxazolidin
- mmol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 51
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 239000003242 anti bacterial agent Substances 0.000 title description 9
- 230000008569 process Effects 0.000 title description 7
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 173
- -1 acetamidomethyl group Chemical group 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 31
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 22
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- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000003971 isoxazolinyl group Chemical group 0.000 claims description 14
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 12
- 230000000844 anti-bacterial effect Effects 0.000 claims description 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
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- 239000003814 drug Substances 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
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- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
- 125000005418 aryl aryl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
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- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
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- 150000002513 isocyanates Chemical class 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- FIFFVUYIGLBKNC-UXHICEINSA-N n-[[(5s)-3-[4-[4-[(5r)-5-(hydroxymethyl)-4,5-dihydro-1,2-oxazol-3-yl]phenyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2C=CC(=CC=2)C=2C[C@H](CO)ON=2)C=C1 FIFFVUYIGLBKNC-UXHICEINSA-N 0.000 claims description 2
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- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 239000012048 reactive intermediate Substances 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
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- 229960005286 carbaryl Drugs 0.000 claims 1
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- WZKQFCQAUZSVQN-GFCCVEGCSA-N tert-butyl n-[[(5r)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-n-(1,2-oxazol-3-yl)carbamate Chemical compound C([C@@H](OC1=O)CN(C(=O)OC(C)(C)C)C2=NOC=C2)N1C1=CC=C(I)C(F)=C1 WZKQFCQAUZSVQN-GFCCVEGCSA-N 0.000 description 1
- SEISUZDQTKBFHE-JTQLQIEISA-N tert-butyl n-acetyl-n-[[(5s)-3-(5-iodothiophen-2-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound O=C1O[C@@H](CN(C(=O)C)C(=O)OC(C)(C)C)CN1C1=CC=C(I)S1 SEISUZDQTKBFHE-JTQLQIEISA-N 0.000 description 1
- NKKYPXAAKOWVSE-UHFFFAOYSA-N tert-butyl-[[3-(3-fluoro-4-trimethylstannylphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methoxy]-dimethylsilane Chemical compound O1C(CO[Si](C)(C)C(C)(C)C)CC(C=2C=C(F)C(=CC=2)[Sn](C)(C)C)=N1 NKKYPXAAKOWVSE-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- YCBWXJZXFUKDPU-UHFFFAOYSA-N trimethyl(pyridin-4-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=NC=C1 YCBWXJZXFUKDPU-UHFFFAOYSA-N 0.000 description 1
- SMNUORJXCKOEJS-UHFFFAOYSA-N trimethyl-[4-[5-(triazol-1-ylmethyl)-4,5-dihydro-1,2-oxazol-3-yl]phenyl]stannane Chemical compound C1=CC([Sn](C)(C)C)=CC=C1C(C1)=NOC1CN1N=NC=C1 SMNUORJXCKOEJS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0121942A GB0121942D0 (en) | 2001-09-11 | 2001-09-11 | Chemical compounds |
GB0215420A GB0215420D0 (en) | 2002-07-04 | 2002-07-04 | Chemical compounds |
PCT/GB2002/004120 WO2003022824A1 (en) | 2001-09-11 | 2002-09-09 | Oxazolidinone and/or isoxazoline as antibacterial agents |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20041428L NO20041428L (no) | 2004-06-08 |
NO327010B1 true NO327010B1 (no) | 2009-04-06 |
Family
ID=26246531
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20041428A NO327010B1 (no) | 2001-09-11 | 2004-04-05 | Oksazolidinon og/eller isoksazolin anvendelse derav som antibakterielle midler, farmasoytisk sammensetning og fremgangsmate for fremstilling derav |
Country Status (26)
Country | Link |
---|---|
US (2) | US7396847B2 (es) |
EP (1) | EP1427711B1 (es) |
JP (1) | JP2005507386A (es) |
KR (1) | KR20040044886A (es) |
CN (1) | CN1639136A (es) |
AR (1) | AR036778A1 (es) |
AT (1) | ATE299502T1 (es) |
AU (1) | AU2002329393B2 (es) |
BR (1) | BR0212458A (es) |
CA (1) | CA2459766A1 (es) |
CO (1) | CO5560609A2 (es) |
DE (1) | DE60205030T2 (es) |
DK (1) | DK1427711T3 (es) |
ES (1) | ES2244802T3 (es) |
HK (1) | HK1065789A1 (es) |
HU (1) | HUP0401005A3 (es) |
IL (1) | IL160739A0 (es) |
IS (1) | IS7175A (es) |
MX (1) | MXPA04002303A (es) |
NO (1) | NO327010B1 (es) |
NZ (1) | NZ531621A (es) |
PL (1) | PL369183A1 (es) |
PT (1) | PT1427711E (es) |
RU (1) | RU2004111285A (es) |
SI (1) | SI1427711T1 (es) |
WO (1) | WO2003022824A1 (es) |
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JP2005531504A (ja) | 2002-02-28 | 2005-10-20 | アストラゼネカ アクチボラグ | 化学化合物 |
PL373888A1 (en) * | 2002-04-25 | 2005-09-19 | Basf Aktiengesellschaft | 3-heteroaryl substituted 5-methyloxymethyl isoxazolines used as herbicides |
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GB0227701D0 (en) * | 2002-11-28 | 2003-01-08 | Astrazeneca Ab | Chemical compounds |
KR20050084010A (ko) * | 2002-11-28 | 2005-08-26 | 아스트라제네카 아베 | 항균제로서의 옥사졸리디논 |
AU2003302404B2 (en) * | 2002-11-28 | 2008-06-19 | Astrazeneca Ab | Oxazolidinone and / or isoxazoline derivatives as antibacterial agents |
GB0229526D0 (en) * | 2002-12-19 | 2003-01-22 | Astrazeneca Ab | Chemical compounds |
GB0229522D0 (en) * | 2002-12-19 | 2003-01-22 | Astrazeneca Ab | Chemical compounds |
GB0229521D0 (en) * | 2002-12-19 | 2003-01-22 | Astrazeneca Ab | Chemical compounds |
TW200500360A (en) * | 2003-03-01 | 2005-01-01 | Astrazeneca Ab | Hydroxymethyl compounds |
GB0304723D0 (en) * | 2003-03-01 | 2003-04-02 | Astrazeneca Ab | Chemical compounds |
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-
2002
- 2002-09-09 HU HU0401005A patent/HUP0401005A3/hu unknown
- 2002-09-09 DE DE60205030T patent/DE60205030T2/de not_active Expired - Fee Related
- 2002-09-09 MX MXPA04002303A patent/MXPA04002303A/es active IP Right Grant
- 2002-09-09 CA CA002459766A patent/CA2459766A1/en not_active Abandoned
- 2002-09-09 BR BR0212458-0A patent/BR0212458A/pt not_active IP Right Cessation
- 2002-09-09 AU AU2002329393A patent/AU2002329393B2/en not_active Ceased
- 2002-09-09 SI SI200230188T patent/SI1427711T1/sl unknown
- 2002-09-09 PL PL02369183A patent/PL369183A1/xx not_active Application Discontinuation
- 2002-09-09 AT AT02765019T patent/ATE299502T1/de not_active IP Right Cessation
- 2002-09-09 CN CNA028223276A patent/CN1639136A/zh active Pending
- 2002-09-09 ES ES02765019T patent/ES2244802T3/es not_active Expired - Lifetime
- 2002-09-09 IL IL16073902A patent/IL160739A0/xx unknown
- 2002-09-09 US US10/489,266 patent/US7396847B2/en not_active Expired - Fee Related
- 2002-09-09 RU RU2004111285/04A patent/RU2004111285A/ru not_active Application Discontinuation
- 2002-09-09 NZ NZ531621A patent/NZ531621A/en unknown
- 2002-09-09 JP JP2003526899A patent/JP2005507386A/ja active Pending
- 2002-09-09 KR KR10-2004-7003558A patent/KR20040044886A/ko not_active Application Discontinuation
- 2002-09-09 DK DK02765019T patent/DK1427711T3/da active
- 2002-09-09 EP EP02765019A patent/EP1427711B1/en not_active Expired - Lifetime
- 2002-09-09 WO PCT/GB2002/004120 patent/WO2003022824A1/en active IP Right Grant
- 2002-09-09 PT PT02765019T patent/PT1427711E/pt unknown
- 2002-09-11 AR ARP020103440A patent/AR036778A1/es unknown
-
2004
- 2004-03-09 CO CO04021466A patent/CO5560609A2/es not_active Application Discontinuation
- 2004-03-10 IS IS7175A patent/IS7175A/is unknown
- 2004-04-05 NO NO20041428A patent/NO327010B1/no not_active IP Right Cessation
- 2004-10-29 HK HK04108506A patent/HK1065789A1/xx not_active IP Right Cessation
-
2008
- 2008-05-28 US US12/128,135 patent/US20100137243A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
ES2244802T3 (es) | 2005-12-16 |
HUP0401005A3 (en) | 2007-11-28 |
CN1639136A (zh) | 2005-07-13 |
RU2004111285A (ru) | 2005-10-10 |
IL160739A0 (en) | 2004-08-31 |
NZ531621A (en) | 2005-06-24 |
AU2002329393B2 (en) | 2008-06-12 |
US20050107435A1 (en) | 2005-05-19 |
EP1427711A1 (en) | 2004-06-16 |
US20100137243A1 (en) | 2010-06-03 |
US7396847B2 (en) | 2008-07-08 |
AR036778A1 (es) | 2004-10-06 |
DE60205030T2 (de) | 2006-04-20 |
CO5560609A2 (es) | 2005-09-30 |
PT1427711E (pt) | 2005-11-30 |
BR0212458A (pt) | 2004-10-19 |
HUP0401005A2 (hu) | 2004-08-30 |
DE60205030D1 (de) | 2005-08-18 |
IS7175A (is) | 2004-03-10 |
MXPA04002303A (es) | 2004-06-29 |
JP2005507386A (ja) | 2005-03-17 |
EP1427711B1 (en) | 2005-07-13 |
KR20040044886A (ko) | 2004-05-31 |
WO2003022824A1 (en) | 2003-03-20 |
HK1065789A1 (en) | 2005-03-04 |
ATE299502T1 (de) | 2005-07-15 |
PL369183A1 (en) | 2005-04-18 |
SI1427711T1 (sl) | 2005-12-31 |
CA2459766A1 (en) | 2003-03-20 |
DK1427711T3 (da) | 2005-10-17 |
NO20041428L (no) | 2004-06-08 |
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