ES2603198T3 - Derivados de 1,6-diazabiciclo [3,2,1]octan-7-ona y su uso en el tratamiento de infecciones bacterianas - Google Patents
Derivados de 1,6-diazabiciclo [3,2,1]octan-7-ona y su uso en el tratamiento de infecciones bacterianas Download PDFInfo
- Publication number
- ES2603198T3 ES2603198T3 ES12772808.7T ES12772808T ES2603198T3 ES 2603198 T3 ES2603198 T3 ES 2603198T3 ES 12772808 T ES12772808 T ES 12772808T ES 2603198 T3 ES2603198 T3 ES 2603198T3
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- alkyl
- aryl
- oso2
- halogen
- independently selected
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- 208000035143 Bacterial infection Diseases 0.000 title description 12
- 208000022362 bacterial infectious disease Diseases 0.000 title description 12
- LTBMTKNTTYEJSD-UHFFFAOYSA-N 1,6-diazabicyclo[3.2.1]octan-7-one Chemical class C1N2C(=O)NC1CCC2 LTBMTKNTTYEJSD-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 150000003839 salts Chemical class 0.000 abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 7
- 239000001257 hydrogen Substances 0.000 abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 17
- 229910052736 halogen Inorganic materials 0.000 abstract 17
- 150000002367 halogens Chemical class 0.000 abstract 17
- 125000001424 substituent group Chemical group 0.000 abstract 16
- 125000003118 aryl group Chemical group 0.000 abstract 7
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 7
- 125000001072 heteroaryl group Chemical group 0.000 abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 7
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- 150000001768 cations Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000565 sulfonamide group Chemical group 0.000 abstract 1
- -1 N '- (3-amino-propyl) -hydrazinocarbonyl Chemical group 0.000 description 49
- 238000000034 method Methods 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 28
- 239000002253 acid Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000003242 anti bacterial agent Substances 0.000 description 14
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 230000002265 prevention Effects 0.000 description 10
- FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 10
- 229960005256 sulbactam Drugs 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 241000588724 Escherichia coli Species 0.000 description 8
- 102000006635 beta-lactamase Human genes 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
- 108090000204 Dipeptidase 1 Proteins 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 6
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMHGLONVYIYIOU-VXGBXAGGSA-N (2r,5r)-7-oxo-6-phenylmethoxy-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid Chemical compound C([C@]1(CC[C@@H]2C(O)=O)[H])N2C(=O)N1OCC1=CC=CC=C1 UMHGLONVYIYIOU-VXGBXAGGSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 description 3
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 3
- XQSAEPZYVKWWRC-HRDYMLBCSA-N (2S)-2-[[[(2R,5R)-7-oxo-6-sulfooxy-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]carbamoyl]pyrrolidine-1-carboxylic acid Chemical compound O=C([C@@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])NNC(=O)[C@@H]1CCCN1C(O)=O XQSAEPZYVKWWRC-HRDYMLBCSA-N 0.000 description 2
- XXQPTJLXNNCWNR-OPRDCNLKSA-N (3R)-3-[[[(2R,5R)-7-oxo-6-sulfooxy-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]carbamoyl]piperidine-1-carboxylic acid Chemical compound O(S(=O)(=O)O)N1[C@@H]2CC[C@@H](N(C1=O)C2)C(=O)NNC(=O)[C@H]1CN(CCC1)C(=O)O XXQPTJLXNNCWNR-OPRDCNLKSA-N 0.000 description 2
- 108020004256 Beta-lactamase Proteins 0.000 description 2
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000003781 beta lactamase inhibitor Substances 0.000 description 2
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 description 2
- 229960000484 ceftazidime Drugs 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 2
- 229960003324 clavulanic acid Drugs 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LPQZKKCYTLCDGQ-WEDXCCLWSA-N tazobactam Chemical compound C([C@]1(C)S([C@H]2N(C(C2)=O)[C@H]1C(O)=O)(=O)=O)N1C=CN=N1 LPQZKKCYTLCDGQ-WEDXCCLWSA-N 0.000 description 2
- 229960003865 tazobactam Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 2
- NXILIHONWRXHFA-MRVPVSSYSA-N (3r)-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-3-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H](C(O)=O)C1 NXILIHONWRXHFA-MRVPVSSYSA-N 0.000 description 1
- HRMRQBJUFWFQLX-SSDOTTSWSA-N (3r)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](C(O)=O)C1 HRMRQBJUFWFQLX-SSDOTTSWSA-N 0.000 description 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- 241000589291 Acinetobacter Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 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 description 1
- 208000031729 Bacteremia Diseases 0.000 description 1
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- 208000002633 Febrile Neutropenia Diseases 0.000 description 1
- 208000036209 Intraabdominal Infections Diseases 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010062255 Soft tissue infection Diseases 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 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 description 1
- 229960003644 aztreonam Drugs 0.000 description 1
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- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 1
- 229960002182 imipenem Drugs 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- DZBBETFUSYTYBU-ZETCQYMHSA-N tert-butyl n-amino-n-[(2s)-pyrrolidine-2-carbonyl]carbamate Chemical compound CC(C)(C)OC(=O)N(N)C(=O)[C@@H]1CCCN1 DZBBETFUSYTYBU-ZETCQYMHSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- FPZLLRFZJZRHSY-HJYUBDRYSA-N tigecycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O FPZLLRFZJZRHSY-HJYUBDRYSA-N 0.000 description 1
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- 239000002132 β-lactam antibiotic Substances 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A—HUMAN NECESSITIES
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- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
- A61K31/546—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, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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| KR20180110181A (ko) | 2010-09-10 | 2018-10-08 | 셈프라 파마슈티컬스, 인크. | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
| US8772490B2 (en) | 2010-12-22 | 2014-07-08 | Meiji Seika Pharma Co., Ltd. | Optically active diazabicyclooctane derivatives and process for preparing the same |
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| CN104470527B (zh) | 2012-03-27 | 2019-05-28 | 森普拉制药公司 | 用于施用大环内酯抗生素的肠胃外制剂 |
| AR090539A1 (es) | 2012-04-02 | 2014-11-19 | Astrazeneca Ab | COMPUESTOS INHIBIDORES DE b LACTAMASA |
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| UA111925C2 (uk) | 2012-12-11 | 2016-06-24 | Федора Фармасьютікалз Інк. | БІЦИКЛІЧНІ СПОЛУКИ ТА ЇХ ВИКОРИСТАННЯ ЯК АНТИБАКТЕРІАЛЬНИХ АГЕНТІВ ТА ІНГІБІТОРІВ β-ЛАКТАМАЗИ |
| KR20150089086A (ko) | 2013-01-14 | 2015-08-04 | 욱크하르트 리미티드 | 박테리아 감염을 치료하기 위한 조성물 및 방법 |
| WO2014135931A1 (en) * | 2013-03-08 | 2014-09-12 | Wockhardt Limited | A process for preparation of (2s, 5r)-7-oxo-6-sulphooxy-2-[((3r)-piperidine-3-carbonyl)-hydrazino carbonyl]-1,6-diaza-bicyclo [3.2.1]- octane |
| BR112015021393A2 (pt) * | 2013-03-08 | 2017-07-18 | Wockhardt Ltd | processo para a preparação de (2s,5r)-7-oxo-6-sulfoóxi-2-[(((3r)-piperidina-3-carbonil)-hidrazina carbonil]-1,6-diaza-biciclo[3.2.1]- octano |
| KR101774132B1 (ko) * | 2013-03-08 | 2017-09-01 | 욱크하르트 리미티드 | (2s, 5r)-7-옥소-6-술포옥시-2-[((3r)-피페리딘-3-카보닐)-히드라지노 카보닐]-1,6-디아자-비사이클로[3.2.1]-옥탄의 제조 방법 |
| WO2014135932A1 (en) * | 2013-03-08 | 2014-09-12 | Wockhardt Limited | A process for preparation of (2s, 5r)-7-oxo-6-sulphooxy-2-[((3r)-pyrrolidine-3-carbonyl)-hydrazino carbonyl]-1,6-diaza-bicyclo[3.2.1]octane |
| CN105163785A (zh) | 2013-03-14 | 2015-12-16 | 森普拉制药公司 | 用于治疗呼吸道疾病的方法及其制剂 |
| WO2014145210A1 (en) | 2013-03-15 | 2014-09-18 | Cempra Pharmaceuticals, Inc. | Convergent processes for preparing macrolide antibacterial agents |
| US9320740B2 (en) | 2013-03-15 | 2016-04-26 | Merck Sharp & Dohme Corp. | Ceftolozane-tazobactam pharmaceutical compositions |
| ES2793201T3 (es) | 2013-09-24 | 2020-11-13 | Meiji Seika Pharma Co Ltd | Procedimiento de producción de derivados y productos intermedios de diazabiciclooctano |
| EP3613740A1 (en) | 2013-10-08 | 2020-02-26 | Meiji Seika Pharma Co., Ltd. | Preparation of a diazabicyclooctane derivative |
| KR102340010B1 (ko) | 2013-10-22 | 2021-12-16 | 욱크하르트 리미티드 | 항균제를 포함하는 제약학적 조성물 |
| AU2014343327A1 (en) * | 2013-10-30 | 2016-05-12 | Wockhardt Limited | Pharmaceutical compositions comprising antibacterial agents |
| CN106715429A (zh) * | 2014-01-21 | 2017-05-24 | 沃克哈特有限公司 | 7‑氧代‑二氮杂二环[3.2.1]辛烷衍生物及其作为抗菌剂的用途 |
| IN2014MU00193A (enExample) * | 2014-01-21 | 2015-08-28 | Wockhardt Ltd | |
| IN2014MU00195A (enExample) | 2014-01-21 | 2015-08-28 | Wockhardt Ltd | |
| MX2016012646A (es) * | 2014-03-29 | 2016-10-28 | Wockhardt Ltd | Composiciones farmaceuticas que comprenden agentes antibacterianos. |
| BR112016024235A2 (pt) * | 2014-04-18 | 2017-08-15 | Wockhardt Ltd | composições farmacêuticas compreendendo agentes antibacterianos |
| SG11201700827RA (en) * | 2014-08-05 | 2017-03-30 | Cempra Pharmaceuticals Inc | Powder oral suspension formulations of antibacterial agents |
| TR201905233T4 (tr) | 2014-11-17 | 2019-05-21 | Entasis Therapeutics Ltd | Dirençli bakteriyel enfeksiyonların tedavisine yönelik kombinasyon tedavisi. |
| TWI691499B (zh) | 2014-12-05 | 2020-04-21 | 日商明治製菓藥業股份有限公司 | 二氮雜雙環辛烷衍生物之結晶及安定的凍結乾燥製劑的製造法 |
| WO2016116788A1 (en) * | 2015-01-24 | 2016-07-28 | Wockhardt Limited | Nitrogen containing bicyclic compounds and their use in treatment of bacterial infections |
| WO2016151543A1 (en) * | 2015-03-25 | 2016-09-29 | Wockhardt Limited | Pharmaceutical compositions comprising antibacterial agents |
| EP3075734A1 (en) * | 2015-03-31 | 2016-10-05 | Mutabilis | Heterocyclic compounds and their use in preventing or treating bacterial infections |
| TW201639853A (zh) | 2015-03-31 | 2016-11-16 | 木塔比利斯公司 | 雜環化合物及其於預防或治療細菌感染之用途 |
| WO2017002083A1 (en) * | 2015-07-02 | 2017-01-05 | Wockhardt Limited | Nitrogen containing bicyclic compounds and their use in treatment of bacterial infections |
| WO2017002086A1 (en) * | 2015-07-02 | 2017-01-05 | Wockhardt Limited | Nitrogen containing bicyclic compounds and their use in treatment of bacterial infections |
| WO2017002089A1 (en) | 2015-07-02 | 2017-01-05 | Wockhardt Limited | Nitrogen containing bicyclic compounds and their use in treatment of bacterial infections |
| US10167283B2 (en) | 2015-09-16 | 2019-01-01 | Suanzhu Pharma Co., Ltd. | β-lactamase inhibitors and uses thereof |
| US9951072B2 (en) | 2015-10-02 | 2018-04-24 | Legochem Biosciences, Inc. | Compositions and methods for inhibiting beta-lactamase |
| US20190077802A1 (en) * | 2015-10-06 | 2019-03-14 | Wockhardt Limited | Difluoro-(2-substituted carbamoyl-1,6-diaza-bicyclo [3.2.1] oct-6-yloxy) acetic acid compounds and their use in treatment of bacterial infections |
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| DE102016005299A1 (de) * | 2016-05-02 | 2017-11-02 | Eisele Pneumatics Gmbh & Co. Kg | Verfahren zum Herstellen eines gebogenen rohrförmigen Verbindungselementes |
| WO2017216764A1 (en) * | 2016-06-17 | 2017-12-21 | Wockhardt Limited | N-(alkanoyl)-7-oxo-6-sulfooxy-1,6-diazabicyclo[3.2.1]octane-2-carbonylhydrazide derivatives and their use as antibacterial agents |
| WO2018053215A1 (en) * | 2016-09-16 | 2018-03-22 | Entasis Therapeutics Limited | Beta-lactamase inhibitor compounds |
| RU2019124705A (ru) * | 2017-02-06 | 2021-02-05 | Мутабилис | Новые гетероциклические соединения и их применение в профилактике или лечении бактериальных инфекций |
| EA037916B1 (ru) * | 2017-02-08 | 2021-06-07 | Энтасис Терапеутикс Лимитед | Соединения-ингибиторы бета-лактамаз |
| US10500195B2 (en) * | 2017-03-02 | 2019-12-10 | Wockhardt Limited | Antibacterial compounds |
| SG11201909443YA (en) | 2017-05-08 | 2019-11-28 | Entasis Therapeutics Inc | Compounds and methods for treating bacterial infections |
| WO2018234962A1 (en) | 2017-06-20 | 2018-12-27 | Wockhardt Limited | Process for o-sulfonation of 1,6-diazabicyclo[3.2.1]octane compounds |
| ES2928152T3 (es) | 2017-12-01 | 2022-11-15 | Qilu Pharmaceutical Co Ltd | Forma cristalina de un inhibidor de beta-lactamasa y método de preparación de la misma |
| CN115151544B (zh) * | 2020-09-01 | 2024-08-16 | 宁夏农林科学院 | β-内酰胺酶抑制剂及其制备 |
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| CN117700415B (zh) * | 2024-02-06 | 2024-04-30 | 成都四面体药物研究有限公司 | 含脲双环化合物、其用途、其制备的药物、其联合用药物及其复方制剂 |
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| FI941212A0 (fi) * | 1991-09-26 | 1994-03-15 | Pfizer | Fuusioituneet trisykliset, typpeä sisältävät heterosykliset yhdisteet |
| CN1046515C (zh) * | 1993-12-29 | 1999-11-17 | 辉瑞大药厂 | 二氮杂双环神经激肽拮抗剂 |
| FR2812635B1 (fr) * | 2000-08-01 | 2002-10-11 | Aventis Pharma Sa | Nouveaux composes heterocycliques, preparation et utilisation comme medicaments notamment comme anti- bacteriens |
| FR2835186B1 (fr) * | 2002-01-28 | 2006-10-20 | Aventis Pharma Sa | Nouveaux composes heterocycliques, actifs comme inhibiteurs de beta-lactamases |
| RS53862B1 (sr) * | 2008-01-18 | 2015-08-31 | Merck Sharp & Dohme Corp. | Inhibitori beta-laktamaze |
| FR2937034B1 (fr) * | 2008-10-10 | 2012-11-23 | Novexel | Nouveaux composes heterocycliques azotes, leur preparation et leur utilisation comme medicaments antibacteriens |
| FR2951171A1 (fr) * | 2009-10-09 | 2011-04-15 | Novexel | Nouveau sel de sodium d'un compose azabicyclique sous forme enantiomere cristallisee et nouvelles formes polymorphes et pseudopolymorphes ainsi que leur preparation |
| US8822450B2 (en) * | 2011-08-27 | 2014-09-02 | Wockhardt Ltd. | 1,6-diazabicyclo [3,2,1] octan-7-one derivatives and their use in the treatment of bacterial infections |
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