JP2005533017A5 - - Google Patents
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- JP2005533017A5 JP2005533017A5 JP2004501418A JP2004501418A JP2005533017A5 JP 2005533017 A5 JP2005533017 A5 JP 2005533017A5 JP 2004501418 A JP2004501418 A JP 2004501418A JP 2004501418 A JP2004501418 A JP 2004501418A JP 2005533017 A5 JP2005533017 A5 JP 2005533017A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- thia
- oxo
- carboxylic acid
- ene
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 31
- -1 substituted Chemical class 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims 9
- 239000002132 β-lactam antibiotic Substances 0.000 claims 9
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- ZIHYVLFLVDRNED-UHFFFAOYSA-M sodium;2-methylhept-2-enoate Chemical compound [Na+].CCCCC=C(C)C([O-])=O ZIHYVLFLVDRNED-UHFFFAOYSA-M 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims 4
- FVUCWGGFZNLYLD-UHFFFAOYSA-M [Na+].C(C=CCCCC)C(=O)[O-] Chemical compound [Na+].C(C=CCCCC)C(=O)[O-] FVUCWGGFZNLYLD-UHFFFAOYSA-M 0.000 claims 3
- 229960003022 amoxicillin Drugs 0.000 claims 3
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims 3
- 229960002292 piperacillin Drugs 0.000 claims 3
- WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 claims 3
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims 2
- FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 229940088710 antibiotic agent Drugs 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000005325 aryloxy aryl group Chemical group 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- SUGVDSNWWQKWCE-LESAWYNJSA-M sodium (5R,6Z)-6-(4,6-dihydropyrazolo[1,5-c][1,3]thiazol-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound O=C1/C(/[C@H]2SC=C(N12)C(=O)[O-])=C/C1=NN2CSCC2=C1.[Na+] SUGVDSNWWQKWCE-LESAWYNJSA-M 0.000 claims 2
- JETQIUPBHQNHNZ-NJBDSQKTSA-N (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-phenyl-2-sulfoacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H](C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)S(O)(=O)=O)=CC=CC=C1 JETQIUPBHQNHNZ-NJBDSQKTSA-N 0.000 claims 1
- DWYDARUUOLMALM-TWLAMCEISA-N (5r,6z)-6-(6,7-dihydro-4h-pyrazolo[5,1-c][1,4]oxazin-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1=C2COCCN2N=C1/C=C1/C(=O)N2[C@@H]1SC=C2C(=O)O DWYDARUUOLMALM-TWLAMCEISA-N 0.000 claims 1
- QQDDJIUJAPMCCX-SIBGDRKGSA-N (5r,6z)-6-[(5-benzyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-2-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1([C@@H]2SC=C1C(=O)O)C(=O)\C2=C\C(SC=1CC2)=CC=1CN2CC1=CC=CC=C1 QQDDJIUJAPMCCX-SIBGDRKGSA-N 0.000 claims 1
- TZHYRIOYHMAWIJ-KGHNQEBZSA-N (5r,6z)-7-oxo-6-[(4-oxo-6,7-dihydropyrazolo[5,1-c][1,4]oxazin-2-yl)methylidene]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1=C2C(=O)OCCN2N=C1/C=C1/C(=O)N2[C@@H]1SC=C2C(=O)O TZHYRIOYHMAWIJ-KGHNQEBZSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 1
- VAEBCNPDQMGFNE-UHFFFAOYSA-N 6-(6,7-dihydro-4h-thieno[3,2-c]pyran-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1OCCC(S2)=C1C=C2C=C1C(=O)N2C1SC=C2C(=O)O VAEBCNPDQMGFNE-UHFFFAOYSA-N 0.000 claims 1
- YKGCKZGARDHVBE-UHFFFAOYSA-N 6-(6,7-dihydro-4h-thieno[3,2-c]thiopyran-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1SCCC(S2)=C1C=C2C=C1C(=O)N2C1SC=C2C(=O)O YKGCKZGARDHVBE-UHFFFAOYSA-N 0.000 claims 1
- GEBFRXZPTJKYPE-UHFFFAOYSA-N 6-[(5-ethoxycarbonyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-2-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1N(C(=O)OCC)CCC2=C1C=C(C=C1C(N3C(=CSC31)C(O)=O)=O)S2 GEBFRXZPTJKYPE-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- YCUYDSZGQWAXRY-UHFFFAOYSA-N CC(=CCCCC)C(=O)O.[Na] Chemical compound CC(=CCCCC)C(=O)O.[Na] YCUYDSZGQWAXRY-UHFFFAOYSA-N 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 claims 1
- JWCSIUVGFCSJCK-CAVRMKNVSA-N Disodium Moxalactam Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CO[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C1=CC=C(O)C=C1 JWCSIUVGFCSJCK-CAVRMKNVSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 229930182555 Penicillin Natural products 0.000 claims 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 229960000723 ampicillin Drugs 0.000 claims 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims 1
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 claims 1
- 229960003644 aztreonam Drugs 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 claims 1
- 229960003866 cefaloridine Drugs 0.000 claims 1
- 229960000603 cefalotin Drugs 0.000 claims 1
- 229960002420 cefatrizine Drugs 0.000 claims 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 claims 1
- 229960001139 cefazolin Drugs 0.000 claims 1
- MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 claims 1
- 229960002588 cefradine Drugs 0.000 claims 1
- 229940106164 cephalexin Drugs 0.000 claims 1
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 claims 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 claims 1
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 claims 1
- RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229960000433 latamoxef Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 229940049954 penicillin Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 230000002829 reductive effect Effects 0.000 claims 1
- PHMQLKCJGJCTLT-VLQAWENLSA-M sodium (5R,6Z)-6-(2,3-dihydropyrazolo[5,1-b][1,3]thiazol-6-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound S1C=2N(CC1)N=C(C=2)\C=C\1/[C@H]2SC=C(N2C/1=O)C(=O)[O-].[Na+] PHMQLKCJGJCTLT-VLQAWENLSA-M 0.000 claims 1
- ZDKUWOPXFSFLND-WBFSQFMTSA-M sodium (5R,6Z)-6-(5,7-dihydro-4H-pyrazolo[1,5-c][1,3]thiazin-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound N1=C(C=C2CCSCN12)\C=C\1/[C@H]2SC=C(N2C/1=O)C(=O)[O-].[Na+] ZDKUWOPXFSFLND-WBFSQFMTSA-M 0.000 claims 1
- PXKLWHWKLDQKEF-DZIFNFPVSA-M sodium (5R,6Z)-6-(5,7-dihydroimidazo[1,2-c][1,3]thiazol-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C1C2=NC(=CN2CS1)/C=C/3\[C@@H]4N(C3=O)C(=CS4)C(=O)[O-].[Na+] PXKLWHWKLDQKEF-DZIFNFPVSA-M 0.000 claims 1
- OUQLXWMNFXEEGF-UYTGOYFPSA-M sodium (6Z)-6-(5,6-dihydro-4H-cyclopenta[b]furan-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C1CC2=C(C1)OC(=C2)/C=C/3\C4N(C3=O)C(=CS4)C(=O)[O-].[Na+] OUQLXWMNFXEEGF-UYTGOYFPSA-M 0.000 claims 1
- HHGFWQVGBHTXHX-NGRDVXTNSA-M sodium (6Z)-6-(6,8-dihydro-5H-imidazo[2,1-c][1,4]thiazin-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound N=1C(=CN2C=1CSCC2)\C=C\1/C2SC=C(N2C/1=O)C(=O)[O-].[Na+] HHGFWQVGBHTXHX-NGRDVXTNSA-M 0.000 claims 1
- VPGJCAZRMJTNIN-WONROIIJSA-M sodium (6Z)-6-[(5,5-dioxo-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C1CS(=O)(=O)CC2=CC(=NN21)/C=C/3\C4N(C3=O)C(=CS4)C(=O)[O-].[Na+] VPGJCAZRMJTNIN-WONROIIJSA-M 0.000 claims 1
- GVHDSAYSZMRHCR-WIMVAJRLSA-M sodium (6Z)-6-[(6,6-dimethyl-7,8-dihydro-5H-imidazo[1,2-a]pyridin-2-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound CC1(CCC2=NC(=CN2C1)/C=C/3\C4N(C3=O)C(=CS4)C(=O)[O-])C.[Na+] GVHDSAYSZMRHCR-WIMVAJRLSA-M 0.000 claims 1
- JNLPKXGXSAQCGN-ZTXYIFKNSA-M sodium (6Z)-6-[(7-benzyl-6,8-dihydro-5H-imidazo[1,2-a]pyrazin-2-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C1CN2C=C(N=C2CN1CC3=CC=CC=C3)/C=C/4\C5N(C4=O)C(=CS5)C(=O)[O-].[Na+] JNLPKXGXSAQCGN-ZTXYIFKNSA-M 0.000 claims 1
- XREVOTNYKGMPMS-WONROIIJSA-M sodium (6Z)-6-[(7-methyl-6,8-dihydro-5H-imidazo[1,2-a]pyrazin-2-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound CN1CCN2C=C(N=C2C1)/C=C/3\C4N(C3=O)C(=CS4)C(=O)[O-].[Na+] XREVOTNYKGMPMS-WONROIIJSA-M 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- MAOMPSXLHMNKJY-VLQAWENLSA-M sodium;(5r,6z)-6-(2,3-dihydropyrazolo[5,1-b][1,3]oxazol-6-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].C1=C2OCCN2N=C1/C=C1/C(=O)N2[C@@H]1SC=C2C(=O)[O-] MAOMPSXLHMNKJY-VLQAWENLSA-M 0.000 claims 1
- RFSWVJXWZXQOSW-NGRDVXTNSA-M sodium;(6z)-6-(6,8-dihydro-5h-imidazo[2,1-c][1,4]oxazin-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].C1COCC2=NC(/C=C3/C(=O)N4C3SC=C4C(=O)[O-])=CN21 RFSWVJXWZXQOSW-NGRDVXTNSA-M 0.000 claims 1
- MJECQFMGPFJWIJ-WENINEFDSA-M sodium;(6z)-6-[(7-methyl-6-oxo-5,8-dihydroimidazo[1,2-a]pyrazin-2-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].C1C(=O)N(C)CC2=NC(\C=C/3C(N4C(=CSC4\3)C([O-])=O)=O)=CN21 MJECQFMGPFJWIJ-WENINEFDSA-M 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 229960004932 sulbenicillin Drugs 0.000 claims 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims 1
- 229960004659 ticarcillin Drugs 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37705202P | 2002-05-01 | 2002-05-01 | |
| PCT/US2003/013428 WO2003093279A1 (en) | 2002-05-01 | 2003-04-30 | BICYCLIC 6-ALKYLIDENE-PENEMS AS ß-LACTAMASES INHIBITORS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010127126A Division JP2010215652A (ja) | 2002-05-01 | 2010-06-02 | β−ラクタマーゼ阻害剤としての二環式６−アルキリデン−ペネム |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005533017A JP2005533017A (ja) | 2005-11-04 |
| JP2005533017A5 true JP2005533017A5 (enExample) | 2006-03-23 |
| JP4602759B2 JP4602759B2 (ja) | 2010-12-22 |
Family
ID=29401437
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004501418A Expired - Fee Related JP4602759B2 (ja) | 2002-05-01 | 2003-04-30 | β−ラクタマーゼ阻害剤としての二環式６−アルキリデン−ペネム |
| JP2010127126A Pending JP2010215652A (ja) | 2002-05-01 | 2010-06-02 | β−ラクタマーゼ阻害剤としての二環式６−アルキリデン−ペネム |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010127126A Pending JP2010215652A (ja) | 2002-05-01 | 2010-06-02 | β−ラクタマーゼ阻害剤としての二環式６−アルキリデン−ペネム |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US7112582B2 (enExample) |
| EP (2) | EP1988093A1 (enExample) |
| JP (2) | JP4602759B2 (enExample) |
| KR (1) | KR20050007368A (enExample) |
| CN (2) | CN1649883B (enExample) |
| AR (1) | AR039774A1 (enExample) |
| AU (1) | AU2003231205A1 (enExample) |
| BR (1) | BR0309757A (enExample) |
| CA (1) | CA2483538A1 (enExample) |
| CR (3) | CR7508A (enExample) |
| EC (1) | ECSP045397A (enExample) |
| IL (1) | IL164899A0 (enExample) |
| MX (1) | MXPA04010663A (enExample) |
| NO (1) | NO20044549L (enExample) |
| NZ (1) | NZ536182A (enExample) |
| RU (1) | RU2339640C2 (enExample) |
| SG (1) | SG162614A1 (enExample) |
| TW (1) | TW200307687A (enExample) |
| UA (1) | UA79117C2 (enExample) |
| WO (1) | WO2003093279A1 (enExample) |
| ZA (1) | ZA200409686B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR039476A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | Proceso para preparar derivados de 6-alquiliden penem |
| US20040132708A1 (en) * | 2002-05-01 | 2004-07-08 | Wyeth | Process for preparing 6-alkylidene penem derivatives |
| AR039774A1 (es) | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| AR039475A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
| CA2536910A1 (en) * | 2003-08-25 | 2005-03-10 | Revaax Pharmaceuticals, Llc | Oral neurotherapeutic cefazolin compositions |
| TW200716104A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Tricyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| TW200716102A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| PE20070403A1 (es) * | 2005-07-27 | 2007-05-15 | Wyeth Corp | COMPOSICION FARMACEUTICA QUE COMPRENDE CEFEPIME Y DERIVADOS DE 6-ALQUILIDEN-PENEM BICICLICOS COMO INHIBIDORES DE ß-LACTAMASA |
| MX2008001083A (es) * | 2005-07-27 | 2008-03-19 | Wyeth Corp | Inhibidores de 6-alquiliden-penem b-lactamasa triciclicos y combinacion de antibioticos de beta-lactama: un antibiotico de amplio espectro. |
| GT200600380A (es) * | 2005-08-24 | 2007-03-29 | Proceso para la preparacion de inhibidores de beta-lactamasa | |
| US20090018332A1 (en) * | 2007-06-28 | 2009-01-15 | Wyeth | Processes For Preparing Bicyclic Oxazine Carboxaldehyde and Beta-Lactamase Inhibitors |
| CN104119858A (zh) * | 2013-04-27 | 2014-10-29 | 海洋王照明科技股份有限公司 | 一种铱金属配合物有机电致磷光材料及其制备方法和有机电致发光器件 |
| CN104119857A (zh) * | 2013-04-27 | 2014-10-29 | 海洋王照明科技股份有限公司 | 一种铱金属配合物有机电致磷光材料及其制备方法和有机电致发光器件 |
| KR102148587B1 (ko) | 2016-02-23 | 2020-08-26 | 화이자 인코포레이티드 | 6,7-디히드로-5H-피라졸로[5,1-b][1,3]옥사진-2-카르복스아미드 화합물 |
| CN108473510B (zh) * | 2016-04-28 | 2021-10-29 | 豪夫迈·罗氏有限公司 | 制备2-吡唑并[1,5-a]吡嗪-2-基吡啶并[1,2-a]嘧啶-4-酮的方法 |
| AU2017314083B2 (en) | 2016-08-15 | 2020-12-10 | Bayer Aktiengesellschaft | Condensed bicyclic heterocycle derivatives as pest control agents |
| CN114957258A (zh) * | 2021-02-25 | 2022-08-30 | 华东理工大学 | 基于碳青霉烯结构的广谱丝氨酸β-内酰胺酶抑制剂的合成及其在耐药细菌抑制中的应用 |
| CN117279917A (zh) * | 2021-05-21 | 2023-12-22 | 成都百裕制药股份有限公司 | 哌嗪衍生物及其在医药上的应用 |
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| US2004A (en) * | 1841-03-12 | Improvement in the manner of constructing and propelling steam-vessels | ||
| US4206067A (en) * | 1978-10-02 | 1980-06-03 | Chevron Research Company | Thermally stabilized erosion-inhibited functional fluids containing perhalometal compounds and an organic base |
| DE3176517D1 (en) | 1980-04-24 | 1987-12-17 | Beecham Group Plc | Beta-lactam compounds, their preparation and use |
| EP0120613A1 (en) | 1983-03-02 | 1984-10-03 | Beecham Group Plc | Penem derivatives and precursors |
| GB8402086D0 (en) | 1984-01-26 | 1984-02-29 | Beecham Group Plc | Compounds |
| FI82471C (fi) | 1984-01-26 | 1991-03-11 | Beecham Group Plc | Foerfarande foer framstaellning av farmakologiskt aktiva 6-metylenpenemderivater. |
| EP0150984B1 (en) | 1984-01-30 | 1991-09-11 | Pfizer Inc. | 6-(substituted) methylenepenicillanic and 6-(substituted) hydroxymethylpenicillanic acids and derivatives thereof |
| EP0167050A1 (en) * | 1984-06-21 | 1986-01-08 | Beecham Group Plc | Clavulanate compounds, their preparation and use and intermediates thereof |
| GB8518421D0 (en) | 1985-07-22 | 1985-08-29 | Beecham Group Plc | Compounds |
| GB8518422D0 (en) | 1985-07-22 | 1985-08-29 | Beecham Group Plc | Compounds |
| GB8518416D0 (en) * | 1985-07-22 | 1985-08-29 | Beecham Group Plc | Compounds |
| DE3752124T2 (de) | 1986-01-17 | 1998-03-26 | Beecham Group Plc | Verfahren zur Herstellung von Penem Derivaten und Zwischenprodukte zu dieser Herstellung |
| US4891369A (en) * | 1986-12-03 | 1990-01-02 | Taiho Pharmaceutical Company, Limited | 2β-Substituted-methylpenicillanic acid derivatives, and salts and esters thereof |
| DE3725375A1 (de) * | 1987-07-31 | 1989-02-09 | Bayer Ag | Stabile oxapenem-3-carbonsaeuren |
| GB8724566D0 (en) | 1987-10-20 | 1987-11-25 | Roussel Lab Ltd | Chemical compounds |
| GB8729613D0 (en) | 1987-12-18 | 1988-02-03 | Beecham Group Plc | Novel compounds |
| GB8729614D0 (en) | 1987-12-18 | 1988-02-03 | Beecham Group Plc | Novel compounds |
| NZ237202A (en) | 1990-02-23 | 1994-01-26 | Bristol Myers Squibb Co | Composition containing beta-lactam antibiotic and cationic oligopeptide |
| EP0447704A1 (en) | 1990-03-21 | 1991-09-25 | Smithkline Beecham Farmaceutici S.p.A. | N-Acylated azacyclic compounds, processes for their preparations and their use as medications |
| GB9116236D0 (en) | 1991-07-27 | 1991-09-11 | Smithkline Beecham Plc | Novel compounds |
| GB9222700D0 (en) * | 1992-10-29 | 1992-12-09 | Smithkline Beecham Plc | Chemical compounds |
| US5349045A (en) | 1993-01-26 | 1994-09-20 | United States Surgical Corporation | Polymer derived from cyclic amide and medical devices manufactured therefrom |
| GB9326248D0 (en) * | 1993-12-23 | 1994-02-23 | Smithkline Beecham Plc | Pharmaceutical formulations |
| CZ286898B6 (en) | 1994-04-25 | 2000-07-12 | Smithkline Beecham Plc | Pharmaceutical preparation |
| US5629322A (en) | 1994-11-15 | 1997-05-13 | Merck & Co., Inc. | Cyclic amidine analogs as inhibitors of nitric oxide synthase |
| WO2000021514A2 (en) * | 1998-10-15 | 2000-04-20 | Sarawak Medichem Pharmaceuticals, Inc. | Method and composition for treating and preventing tuberculosis |
| GB9928290D0 (en) * | 1999-12-01 | 2000-01-26 | Univ Belfast | Process for preparing ambient temperature ionic liquids |
| EP1199077A1 (en) * | 2000-10-19 | 2002-04-24 | Amura Limited | Stable compositions of oxapenem-3-carboxylic acids by Co-lyophilisation with pharmaceutical carriers |
| GB0106428D0 (en) * | 2001-03-15 | 2001-05-02 | Amura Ltd | Antibacterial composition |
| AR039476A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | Proceso para preparar derivados de 6-alquiliden penem |
| AR039774A1 (es) | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| US20040132708A1 (en) * | 2002-05-01 | 2004-07-08 | Wyeth | Process for preparing 6-alkylidene penem derivatives |
| AR039475A1 (es) | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
| AR046041A1 (es) * | 2003-10-03 | 2005-11-23 | Aventis Pharma Inc | Procedimiento para la preparacion de compuestos heterociclicos n-amino sustituidos |
| TW200716102A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| TW200716104A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Tricyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| PE20070403A1 (es) * | 2005-07-27 | 2007-05-15 | Wyeth Corp | COMPOSICION FARMACEUTICA QUE COMPRENDE CEFEPIME Y DERIVADOS DE 6-ALQUILIDEN-PENEM BICICLICOS COMO INHIBIDORES DE ß-LACTAMASA |
-
2003
- 2003-04-28 AR ARP030101471A patent/AR039774A1/es unknown
- 2003-04-29 TW TW092110033A patent/TW200307687A/zh unknown
- 2003-04-30 MX MXPA04010663A patent/MXPA04010663A/es active IP Right Grant
- 2003-04-30 BR BR0309757-9A patent/BR0309757A/pt not_active IP Right Cessation
- 2003-04-30 RU RU2004135082/04A patent/RU2339640C2/ru not_active IP Right Cessation
- 2003-04-30 CA CA002483538A patent/CA2483538A1/en not_active Abandoned
- 2003-04-30 JP JP2004501418A patent/JP4602759B2/ja not_active Expired - Fee Related
- 2003-04-30 WO PCT/US2003/013428 patent/WO2003093279A1/en not_active Ceased
- 2003-04-30 CN CN038097338A patent/CN1649883B/zh not_active Expired - Fee Related
- 2003-04-30 EP EP08004917A patent/EP1988093A1/en not_active Withdrawn
- 2003-04-30 EP EP03724340A patent/EP1499621A1/en not_active Ceased
- 2003-04-30 SG SG200607462-9A patent/SG162614A1/en unknown
- 2003-04-30 AU AU2003231205A patent/AU2003231205A1/en not_active Abandoned
- 2003-04-30 UA UA20041109833A patent/UA79117C2/uk unknown
- 2003-04-30 NZ NZ536182A patent/NZ536182A/en not_active IP Right Cessation
- 2003-04-30 KR KR10-2004-7017597A patent/KR20050007368A/ko not_active Ceased
- 2003-04-30 CN CNA2009101331547A patent/CN101570545A/zh active Pending
- 2003-05-01 US US10/427,380 patent/US7112582B2/en not_active Expired - Fee Related
-
2004
- 2004-10-06 CR CR7508A patent/CR7508A/es not_active Application Discontinuation
- 2004-10-22 NO NO20044549A patent/NO20044549L/no not_active Application Discontinuation
- 2004-10-28 IL IL16489904A patent/IL164899A0/xx unknown
- 2004-10-29 EC EC2004005397A patent/ECSP045397A/es unknown
- 2004-11-30 ZA ZA200409686A patent/ZA200409686B/xx unknown
-
2006
- 2006-06-06 US US11/447,814 patent/US20060217361A1/en not_active Abandoned
-
2008
- 2008-08-21 US US12/195,706 patent/US7812014B2/en not_active Expired - Fee Related
-
2009
- 2009-08-21 CR CR10986A patent/CR10986A/es not_active Application Discontinuation
- 2009-08-21 CR CR10983A patent/CR10983A/es not_active Application Discontinuation
-
2010
- 2010-06-02 JP JP2010127126A patent/JP2010215652A/ja active Pending
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