ES2272795T3 - 7-alquildieno-3-sustituidos-3-cefem-4-carboxilatos como inhibidores de beta-lactamasa. - Google Patents
7-alquildieno-3-sustituidos-3-cefem-4-carboxilatos como inhibidores de beta-lactamasa. Download PDFInfo
- Publication number
- ES2272795T3 ES2272795T3 ES02789149T ES02789149T ES2272795T3 ES 2272795 T3 ES2272795 T3 ES 2272795T3 ES 02789149 T ES02789149 T ES 02789149T ES 02789149 T ES02789149 T ES 02789149T ES 2272795 T3 ES2272795 T3 ES 2272795T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- alkyl
- alkanoyloxy
- aryl
- alkanoyl
- 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.)
- Expired - Lifetime
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- 239000003112 inhibitor Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- -1 nitro, mercapto Chemical class 0.000 claims abstract description 50
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 150000002978 peroxides Chemical class 0.000 claims abstract description 4
- 125000006413 ring segment Chemical group 0.000 claims abstract description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- IBAHLNWTOIHLKE-UHFFFAOYSA-N cyano cyanate Chemical compound N#COC#N IBAHLNWTOIHLKE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 29
- 230000003115 biocidal effect Effects 0.000 claims description 19
- 102000006635 beta-lactamase Human genes 0.000 claims description 17
- 150000003952 β-lactams Chemical class 0.000 claims description 16
- 108090000204 Dipeptidase 1 Proteins 0.000 claims description 14
- 239000003242 anti bacterial agent Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 description 34
- 239000000243 solution Substances 0.000 description 28
- 150000002148 esters Chemical class 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000007788 liquid Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003781 beta lactamase inhibitor Substances 0.000 description 12
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 239000002775 capsule Substances 0.000 description 10
- 238000010511 deprotection reaction Methods 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
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- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- 239000012267 brine Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 108020004256 Beta-lactamase Proteins 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007832 Na2SO4 Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
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- 235000019698 starch Nutrition 0.000 description 6
- 239000002132 β-lactam antibiotic Substances 0.000 description 6
- 229940124586 β-lactam antibiotics Drugs 0.000 description 6
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
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- 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 5
- 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 description 5
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- 230000002401 inhibitory effect Effects 0.000 description 5
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- 231100000252 nontoxic Toxicity 0.000 description 5
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 150000002334 glycols Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
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- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HDKCVDHYIIKWFM-UHFFFAOYSA-K octanoate;rhodium(3+) Chemical compound [Rh+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HDKCVDHYIIKWFM-UHFFFAOYSA-K 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229950009506 penicillinase Drugs 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 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
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- KAYCSCULGYYNFT-UHFFFAOYSA-N triphenyl(pyridin-2-ylmethyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=N1 KAYCSCULGYYNFT-UHFFFAOYSA-N 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero 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
-
- 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
Landscapes
- 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)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30740301P | 2001-07-24 | 2001-07-24 | |
| US307403P | 2001-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2272795T3 true ES2272795T3 (es) | 2007-05-01 |
Family
ID=23189607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02789149T Expired - Lifetime ES2272795T3 (es) | 2001-07-24 | 2002-07-24 | 7-alquildieno-3-sustituidos-3-cefem-4-carboxilatos como inhibidores de beta-lactamasa. |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6916801B2 (enExample) |
| EP (1) | EP1430060B1 (enExample) |
| JP (1) | JP2005502687A (enExample) |
| AT (1) | ATE339424T1 (enExample) |
| AU (1) | AU2002353768A1 (enExample) |
| CA (1) | CA2454413A1 (enExample) |
| DE (1) | DE60214740T2 (enExample) |
| ES (1) | ES2272795T3 (enExample) |
| WO (1) | WO2003020732A2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2178301T3 (es) | 1997-12-29 | 2002-12-16 | Res Corp Technologies Inc | Derivados del acido penicilanico 2-beta-sustituido-6-alquilideno como inhibidores de la beta-lactama. |
| US6407091B1 (en) | 1999-04-15 | 2002-06-18 | Research Corporation Technologies, Inc. | β-lactamase inhibiting compounds |
| US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
| US20020068078A1 (en) | 2000-10-13 | 2002-06-06 | Rudnic Edward M. | Antifungal product, use and formulation thereof |
| AU2002353768A1 (en) | 2001-07-24 | 2003-03-18 | Alamx, L.L.C. | 7-alkylidene-3-substituted-3-cephem-4-carboxylates as beta-lactamase inhibitors. |
| US7022691B2 (en) | 2002-04-04 | 2006-04-04 | John D. Buynak | Inhibitors of serine and metallo-β-lactamases |
| US7833998B2 (en) * | 2003-08-25 | 2010-11-16 | Revaax Pharmaceuticals, Llc | Oral neurotherapeutic cephalosporin sulfoxide and sulfone-containing compositions |
| US8299051B2 (en) * | 2008-05-13 | 2012-10-30 | Southern Methodist University | Beta-lactamase inhibitory compounds |
| KR20110095898A (ko) | 2008-11-20 | 2011-08-25 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 유기 화합물의 플루오르화 |
| EP2697204B1 (en) | 2011-04-12 | 2017-03-08 | President and Fellows of Harvard College | Fluorination of organic compounds |
| US9273083B2 (en) | 2012-09-26 | 2016-03-01 | President And Fellows Of Harvard College | Nickel fluorinating complexes and uses thereof |
| CN103387584B (zh) * | 2013-07-17 | 2015-02-25 | 盐城开元医药化工有限公司 | 一种7-氨基-3-氯-3-头孢环-4-羧酸的合成方法 |
| WO2015058047A2 (en) | 2013-10-18 | 2015-04-23 | President And Fellows Of Harvard College | Fluorination of organic compounds |
| CN105254648B (zh) * | 2015-11-13 | 2018-04-03 | 广东温氏大华农生物科技有限公司 | 一种头孢维星及其钠盐的合成方法 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4053468A (en) | 1976-02-25 | 1977-10-11 | Smithkline Corporation | Process for preparing 7-oxo cephalosporins and 6-oxo penicillins |
| IT1193922B (it) | 1979-02-24 | 1988-08-31 | Erba Farmitalia | Agenti antibatterici ed inibitori di beta -lattamasi e loro preparazione |
| ZA80993B (en) | 1979-02-24 | 1981-02-25 | Erba Farmitalia | -lactam-containing antibacterial agents and -lactamase inhibitors and preparation thereof |
| GB2076812A (en) | 1980-05-22 | 1981-12-09 | Ciba Geigy Ag | Penam-dioxide compounds, processes for their manufacture, and their use |
| DE3173613D1 (en) | 1980-07-04 | 1986-03-13 | Fujisawa Pharmaceutical Co | 7-oxo-cephalosporins and 6-oxo-penicillins, their analogues and process for their preparation |
| CA1180005A (en) | 1980-10-24 | 1984-12-27 | Solange Adam-Molina | .beta.-LACTAMS |
| ZA826687B (en) | 1981-09-14 | 1983-07-27 | Pfizer | Beta-lactamase inhibiting 2-beta-substituted-2-alpha-methyl 5(r)penam-3-alpha-carboxylic acid 1,1-dioxides and intermediates therefor |
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| PT79893B (en) | 1984-01-30 | 1987-02-03 | Pfizer | Process for preparing 6-(substituted)methylenepenicillanic and 6-(substituted)hydroxymethylpenicilanic and derivatives thereof |
| US4826833A (en) | 1984-01-30 | 1989-05-02 | Pfizer Inc. | 6-(Substituted)methylene-penicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof |
| DE3584015D1 (de) | 1984-01-30 | 1991-10-17 | Pfizer | 6-(substituierte) methylen-penicillansaeure und 6-(substituierte) hydroxymethyl-penicillansaeure und deren derivate. |
| EP0170192B1 (en) | 1984-07-30 | 1992-05-13 | Merck & Co. Inc. | Penicillin derivatives as anti-inflammatory and antidegenerative agents |
| JPS62198687A (ja) | 1986-02-27 | 1987-09-02 | Taiho Yakuhin Kogyo Kk | ２β−置換チオメチルペニシリン誘導体 |
| US4861768A (en) | 1986-02-27 | 1989-08-29 | Taiho Pharmaceutical Company, Limited | 2 β-substituted thiomethylpenicillin derivatives and their preparation and use |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| JP2603082B2 (ja) | 1987-09-07 | 1997-04-23 | 大塚化学株式会社 | ペニシラン酸誘導体の製造法 |
| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| IT1227462B (it) | 1988-11-04 | 1991-04-11 | Glaxo Spa | Procedimento di preparazione di 6-ossopenicillanati |
| TW383308B (en) | 1993-08-24 | 2000-03-01 | Hoffmann La Roche | 2-beta-alkenyl penam sulfones as beta-lactamase inhibitors |
| US5597817A (en) | 1994-12-09 | 1997-01-28 | Southern Methodist University | 7-vinylidene cephalosporins and methods of using the same |
| US5629306A (en) * | 1994-12-09 | 1997-05-13 | Research Corporation Technologies, Inc. | 7-alkylidene cephalosporanic acid derivatives and methods of using the same |
| US5760027A (en) | 1996-12-06 | 1998-06-02 | Research Corporation Technologies, Inc. | Use of 7-alkylidene cephalosporins to inhibit elastase activity |
| ES2178301T3 (es) | 1997-12-29 | 2002-12-16 | Res Corp Technologies Inc | Derivados del acido penicilanico 2-beta-sustituido-6-alquilideno como inhibidores de la beta-lactama. |
| AU773013B2 (en) | 1999-04-15 | 2004-05-13 | Research Corporation Technologies, Inc. | Beta-lactamase inhibiting compounds |
| US6391855B1 (en) * | 1999-06-02 | 2002-05-21 | Adherex Technologies, Inc. | Compounds and methods for modulating junctional adhesion molecule-mediated functions |
| AU2002353768A1 (en) * | 2001-07-24 | 2003-03-18 | Alamx, L.L.C. | 7-alkylidene-3-substituted-3-cephem-4-carboxylates as beta-lactamase inhibitors. |
-
2002
- 2002-07-24 AU AU2002353768A patent/AU2002353768A1/en not_active Abandoned
- 2002-07-24 AT AT02789149T patent/ATE339424T1/de not_active IP Right Cessation
- 2002-07-24 US US10/202,405 patent/US6916801B2/en not_active Expired - Fee Related
- 2002-07-24 JP JP2003525002A patent/JP2005502687A/ja active Pending
- 2002-07-24 DE DE60214740T patent/DE60214740T2/de not_active Expired - Fee Related
- 2002-07-24 EP EP02789149A patent/EP1430060B1/en not_active Expired - Lifetime
- 2002-07-24 ES ES02789149T patent/ES2272795T3/es not_active Expired - Lifetime
- 2002-07-24 WO PCT/US2002/023613 patent/WO2003020732A2/en not_active Ceased
- 2002-07-24 CA CA002454413A patent/CA2454413A1/en not_active Abandoned
-
2005
- 2005-05-10 US US11/126,061 patent/US7488724B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE339424T1 (de) | 2006-10-15 |
| WO2003020732A3 (en) | 2003-05-22 |
| US20060074065A1 (en) | 2006-04-06 |
| CA2454413A1 (en) | 2003-03-13 |
| WO2003020732A2 (en) | 2003-03-13 |
| EP1430060B1 (en) | 2006-09-13 |
| AU2002353768A1 (en) | 2003-03-18 |
| US6916801B2 (en) | 2005-07-12 |
| US7488724B2 (en) | 2009-02-10 |
| EP1430060A2 (en) | 2004-06-23 |
| JP2005502687A (ja) | 2005-01-27 |
| DE60214740D1 (en) | 2006-10-26 |
| US20030092696A1 (en) | 2003-05-15 |
| DE60214740T2 (de) | 2007-10-04 |
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