JP2009520813A - カルバメート系抗生物質 - Google Patents
カルバメート系抗生物質 Download PDFInfo
- Publication number
- JP2009520813A JP2009520813A JP2008547129A JP2008547129A JP2009520813A JP 2009520813 A JP2009520813 A JP 2009520813A JP 2008547129 A JP2008547129 A JP 2008547129A JP 2008547129 A JP2008547129 A JP 2008547129A JP 2009520813 A JP2009520813 A JP 2009520813A
- Authority
- JP
- Japan
- Prior art keywords
- ester
- carbamic acid
- dichlorophenyl
- pharmaceutically acceptable
- isobutoxycarbonylamino
- Prior art date
- 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.)
- Ceased
Links
- 239000003242 anti bacterial agent Substances 0.000 title claims description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title description 8
- 229940088710 antibiotic agent Drugs 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 208000015181 infectious disease Diseases 0.000 claims abstract description 13
- 230000003115 biocidal effect Effects 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- MZHXYMLBAOKCEG-UHFFFAOYSA-N 1-(2-methylpropoxycarbonylamino)propan-2-yl n-(3,4-dichlorophenyl)carbamate Chemical compound CC(C)COC(=O)NCC(C)OC(=O)NC1=CC=C(Cl)C(Cl)=C1 MZHXYMLBAOKCEG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000000651 prodrug Substances 0.000 claims description 20
- 229940002612 prodrug Drugs 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- -1 carbamoyloxyethyl ester Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- VTAQLGRULYHNQX-UHFFFAOYSA-N (3,4-dichlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(Cl)C(Cl)=C1 VTAQLGRULYHNQX-UHFFFAOYSA-N 0.000 claims description 2
- HCTWKIQZMDFPLN-UHFFFAOYSA-N 1-(2-methylpropoxycarbonylamino)propan-2-yl n-(3,4-difluorophenyl)carbamate Chemical compound CC(C)COC(=O)NCC(C)OC(=O)NC1=CC=C(F)C(F)=C1 HCTWKIQZMDFPLN-UHFFFAOYSA-N 0.000 claims description 2
- VMCONBRSKZRROA-UHFFFAOYSA-N 1-(2-methylpropoxycarbonylamino)propan-2-yl n-(3,4-dimethoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)CNC(=O)OCC(C)C)C=C1OC VMCONBRSKZRROA-UHFFFAOYSA-N 0.000 claims description 2
- MMZNRBAMSVYLJD-UHFFFAOYSA-N 1-(2-methylpropoxycarbonylamino)propan-2-yl n-(4-methoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)CNC(=O)OCC(C)C)C=C1 MMZNRBAMSVYLJD-UHFFFAOYSA-N 0.000 claims description 2
- ZPYHXTKICCKTGG-UHFFFAOYSA-N 1-(2-methylpropoxycarbonylamino)propan-2-yl n-(4-methylphenyl)carbamate Chemical compound CC(C)COC(=O)NCC(C)OC(=O)NC1=CC=C(C)C=C1 ZPYHXTKICCKTGG-UHFFFAOYSA-N 0.000 claims description 2
- WVYYYXWXXBTASQ-UHFFFAOYSA-N 1-(2-methylpropoxycarbonylamino)propan-2-yl n-[3,4-bis(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)COC(=O)NCC(C)OC(=O)NC1=CC=C(C(F)(F)F)C(C(F)(F)F)=C1 WVYYYXWXXBTASQ-UHFFFAOYSA-N 0.000 claims description 2
- HZOOXPKTLWEYMG-UHFFFAOYSA-N 1-(2-methylpropoxycarbonylamino)propan-2-yl n-[4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)COC(=O)NCC(C)OC(=O)NC1=CC=C(C(F)(F)F)C=C1 HZOOXPKTLWEYMG-UHFFFAOYSA-N 0.000 claims description 2
- IUBSDDOMRUJKMZ-UHFFFAOYSA-N 2-(ethylcarbamoyloxy)ethyl n-(3,4-dichlorophenyl)carbamate Chemical compound CCNC(=O)OCCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 IUBSDDOMRUJKMZ-UHFFFAOYSA-N 0.000 claims description 2
- CBXDYEDDMTVHCV-UHFFFAOYSA-N 2-(methylcarbamoyloxy)ethyl n-(3,4-dichlorophenyl)carbamate Chemical compound CNC(=O)OCCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 CBXDYEDDMTVHCV-UHFFFAOYSA-N 0.000 claims description 2
- VXCBKQMJHCDJOI-UHFFFAOYSA-N 2-(methylsulfonylcarbamoyloxy)ethyl n-(3,4-dichlorophenyl)carbamate Chemical compound CS(=O)(=O)NC(=O)OCCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 VXCBKQMJHCDJOI-UHFFFAOYSA-N 0.000 claims description 2
- DDYMMBCJOZYGDN-UHFFFAOYSA-N 2-(propan-2-ylcarbamoyloxy)ethyl n-(3,4-dichlorophenyl)carbamate Chemical compound CC(C)NC(=O)OCCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 DDYMMBCJOZYGDN-UHFFFAOYSA-N 0.000 claims description 2
- YXIDOVVARJVQDP-UHFFFAOYSA-N 2-acetamidoethyl n-(3,4-dichlorophenyl)carbamate Chemical compound CC(=O)NCCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 YXIDOVVARJVQDP-UHFFFAOYSA-N 0.000 claims description 2
- NLAAEBAZGBQFSA-UHFFFAOYSA-N 2-carbamoyloxyethyl n-(3,4-dichlorophenyl)carbamate Chemical compound NC(=O)OCCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 NLAAEBAZGBQFSA-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229940127557 pharmaceutical product Drugs 0.000 claims 2
- RCFJOIDKQQRXHU-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC=CC(C(F)(F)F)=C1 RCFJOIDKQQRXHU-UHFFFAOYSA-N 0.000 claims 1
- 241000192125 Firmicutes Species 0.000 abstract description 2
- 206010041925 Staphylococcal infections Diseases 0.000 abstract description 2
- 150000002611 lead compounds Chemical class 0.000 abstract 1
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000012467 final product Substances 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 125000006413 ring segment Chemical group 0.000 description 6
- 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 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 108010059993 Vancomycin Proteins 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 150000003857 carboxamides Chemical class 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 125000005309 thioalkoxy group Chemical group 0.000 description 4
- 210000000689 upper leg Anatomy 0.000 description 4
- 229960003165 vancomycin Drugs 0.000 description 4
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical group OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
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- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
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- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- GTIAMJDCVOKYGA-UHFFFAOYSA-N 2-(ethoxycarbonylamino)ethyl n-(3,4-dichlorophenyl)carbamate Chemical compound CCOC(=O)NCCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 GTIAMJDCVOKYGA-UHFFFAOYSA-N 0.000 description 2
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- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 2
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- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05077956A EP1803453A1 (en) | 2005-12-21 | 2005-12-21 | Carbamate antibiotics |
| PCT/NL2006/000651 WO2007073168A1 (en) | 2005-12-21 | 2006-12-21 | Carbamate antibiotics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009520813A true JP2009520813A (ja) | 2009-05-28 |
| JP2009520813A5 JP2009520813A5 (enExample) | 2010-02-12 |
Family
ID=36570860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008547129A Ceased JP2009520813A (ja) | 2005-12-21 | 2006-12-21 | カルバメート系抗生物質 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8058468B2 (enExample) |
| EP (2) | EP1803453A1 (enExample) |
| JP (1) | JP2009520813A (enExample) |
| WO (1) | WO2007073168A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012193132A (ja) * | 2011-03-15 | 2012-10-11 | Sumitomo Seika Chem Co Ltd | アルキルスルホニルカルバメートの製造方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2960875B1 (fr) | 2010-06-04 | 2012-12-28 | Sanofi Aventis | Derives de carbamates d'hexafluoroisopropyle, leur preparation et leur application en therapeutique |
| CA2845241A1 (en) | 2010-08-14 | 2012-02-23 | Versitech Limited | Anti-viral carbamimidothioic acid esters |
| KR102756165B1 (ko) * | 2019-07-16 | 2025-01-20 | 재단법인 한국파스퇴르연구소 | 항―메티실린 내성 황색포도상구균 화합물 및 이의 의약 용도 |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2703810A (en) * | 1951-09-05 | 1955-03-08 | Saint Gobain | Derivatives of glycol urethanes and methods of making them |
| US2777871A (en) * | 1952-08-05 | 1957-01-15 | Columbia Southern Chem Corp | Bis nu-substituted carbamic acid esters of polyhydric alcohols and process |
| FR1400995A (fr) * | 1964-07-16 | 1965-05-28 | Boots Pure Drug Co Ltd | Composition herbicide, nouveaux carbamates utilisables comme herbicides et leur préparation |
| DE1204456B (de) * | 1952-09-25 | 1965-11-04 | Pittsburgh Plate Glass Co | Pflanzenvertilgungsmittel |
| WO1991007381A1 (fr) * | 1989-11-14 | 1991-05-30 | Vsesojuzny Nauchno-Issledovatelsky Institut Khimicheskikh Sredstv Zaschity Rasteny | Derives carbamoyle d'alkanolamine et moyen antistress de regulation de croissance des vegetaux base sur lesdits derives |
| WO2000037434A1 (en) * | 1998-12-22 | 2000-06-29 | Mitsubishi Chemical Corporation | Amide derivatives |
| US6143471A (en) * | 1998-03-10 | 2000-11-07 | Mitsubishi Paper Mills Limited | Positive type photosensitive composition |
| US6294502B1 (en) * | 1998-05-22 | 2001-09-25 | Bayer Aktiengesellschaft | Thermally-responsive record material |
| JP2002030130A (ja) * | 2000-07-18 | 2002-01-31 | National Institute Of Advanced Industrial & Technology | 定序性ポリウレタン及びその製造法 |
| JP2002088135A (ja) * | 2000-02-21 | 2002-03-27 | Nitto Denko Corp | ウレタン共重合体及びこれを用いた光学材料 |
-
2005
- 2005-12-21 EP EP05077956A patent/EP1803453A1/en not_active Withdrawn
-
2006
- 2006-12-21 EP EP06835673A patent/EP1973537A1/en not_active Withdrawn
- 2006-12-21 WO PCT/NL2006/000651 patent/WO2007073168A1/en not_active Ceased
- 2006-12-21 JP JP2008547129A patent/JP2009520813A/ja not_active Ceased
- 2006-12-21 US US12/097,843 patent/US8058468B2/en not_active Expired - Fee Related
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2703810A (en) * | 1951-09-05 | 1955-03-08 | Saint Gobain | Derivatives of glycol urethanes and methods of making them |
| US2777871A (en) * | 1952-08-05 | 1957-01-15 | Columbia Southern Chem Corp | Bis nu-substituted carbamic acid esters of polyhydric alcohols and process |
| DE1204456B (de) * | 1952-09-25 | 1965-11-04 | Pittsburgh Plate Glass Co | Pflanzenvertilgungsmittel |
| FR1400995A (fr) * | 1964-07-16 | 1965-05-28 | Boots Pure Drug Co Ltd | Composition herbicide, nouveaux carbamates utilisables comme herbicides et leur préparation |
| WO1991007381A1 (fr) * | 1989-11-14 | 1991-05-30 | Vsesojuzny Nauchno-Issledovatelsky Institut Khimicheskikh Sredstv Zaschity Rasteny | Derives carbamoyle d'alkanolamine et moyen antistress de regulation de croissance des vegetaux base sur lesdits derives |
| US6143471A (en) * | 1998-03-10 | 2000-11-07 | Mitsubishi Paper Mills Limited | Positive type photosensitive composition |
| US6294502B1 (en) * | 1998-05-22 | 2001-09-25 | Bayer Aktiengesellschaft | Thermally-responsive record material |
| WO2000037434A1 (en) * | 1998-12-22 | 2000-06-29 | Mitsubishi Chemical Corporation | Amide derivatives |
| JP2002088135A (ja) * | 2000-02-21 | 2002-03-27 | Nitto Denko Corp | ウレタン共重合体及びこれを用いた光学材料 |
| JP2002030130A (ja) * | 2000-07-18 | 2002-01-31 | National Institute Of Advanced Industrial & Technology | 定序性ポリウレタン及びその製造法 |
Non-Patent Citations (5)
| Title |
|---|
| JPN5008021413; '"Interchim Intermediates"' DATABASE CHEMCATS,CHEMICAL ABSTRACTS SERVICE Accession No.(AN): 2005:1043693 CHEMCATS, 20050118 * |
| JPN6012051255; JOURNAL OF ORGANIC CHEMISTRY VOL.22,NO.12, 1957, PP.1706-1708 * |
| JPN7012003982; 'CAS Registry No.(RN): 331959-00-3' DATABASE REGISTRY,CHEMICAL ABSTRACTS SERVICE , 20010420 * |
| JPN7012003983; 'CAS Registry No.(RN): 306316-43-8' DATABASE REGISTRY,CHEMICAL ABSTRACTS SERVICE , 20001204 * |
| JPN7012003984; 'CAS Registry No.(RN): 136204-79-0' DATABASE REGISTRY,CHEMICAL ABSTRACTS SERVICE , 19910920 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012193132A (ja) * | 2011-03-15 | 2012-10-11 | Sumitomo Seika Chem Co Ltd | アルキルスルホニルカルバメートの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007073168A1 (en) | 2007-06-28 |
| US8058468B2 (en) | 2011-11-15 |
| EP1973537A1 (en) | 2008-10-01 |
| EP1803453A1 (en) | 2007-07-04 |
| US20090192221A1 (en) | 2009-07-30 |
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