JP7437847B2 - レレバクタムの誘導体およびその使用 - Google Patents
レレバクタムの誘導体およびその使用 Download PDFInfo
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- JP7437847B2 JP7437847B2 JP2021517784A JP2021517784A JP7437847B2 JP 7437847 B2 JP7437847 B2 JP 7437847B2 JP 2021517784 A JP2021517784 A JP 2021517784A JP 2021517784 A JP2021517784 A JP 2021517784A JP 7437847 B2 JP7437847 B2 JP 7437847B2
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- Prior art keywords
- substituted
- alkyl
- formula
- compound
- heterocycloalkyl
- 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.)
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- SMOBCLHAZXOKDQ-ZJUUUORDSA-N [(2s,5r)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical class O=C([C@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])NC1CCNCC1 SMOBCLHAZXOKDQ-ZJUUUORDSA-N 0.000 title claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 840
- 125000000217 alkyl group Chemical group 0.000 claims description 537
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 224
- -1 alkyl arene Chemical class 0.000 claims description 216
- 239000001257 hydrogen Substances 0.000 claims description 196
- 229910052739 hydrogen Inorganic materials 0.000 claims description 196
- 125000003118 aryl group Chemical group 0.000 claims description 131
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 129
- 229910052799 carbon Inorganic materials 0.000 claims description 127
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 123
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 122
- 239000008194 pharmaceutical composition Substances 0.000 claims description 120
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 110
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 110
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 98
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 87
- 125000001072 heteroaryl group Chemical group 0.000 claims description 81
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 74
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 73
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 72
- 125000005842 heteroatom Chemical group 0.000 claims description 63
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 55
- 102000006635 beta-lactamase Human genes 0.000 claims description 54
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 54
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 52
- 208000035143 Bacterial infection Diseases 0.000 claims description 49
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 47
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 43
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 37
- 108090000204 Dipeptidase 1 Proteins 0.000 claims description 34
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 30
- 239000006186 oral dosage form Substances 0.000 claims description 29
- 229950011310 relebactam Drugs 0.000 claims description 23
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 21
- 239000002132 β-lactam antibiotic Substances 0.000 claims description 21
- 229940124586 β-lactam antibiotics Drugs 0.000 claims description 21
- 241000894006 Bacteria Species 0.000 claims description 18
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- PLELQZTXLRWERH-GQXIWKRZSA-N 1-(2-methylpropanoyloxy)ethyl 4-[[(2S,5R)-6-(3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]piperidine-1-carboxylate Chemical compound C(C)OC(C(COS(=O)(=O)ON1[C@@H]2CC[C@H](N(C1=O)C2)C(=O)NC1CCN(CC1)C(=O)OC(C)OC(C(C)C)=O)(C)C)=O PLELQZTXLRWERH-GQXIWKRZSA-N 0.000 claims description 13
- OVKXDANNQWXYKF-UHFFFAOYSA-N 2-methyloctanamide Chemical compound CCCCCCC(C)C(N)=O OVKXDANNQWXYKF-UHFFFAOYSA-N 0.000 claims description 11
- IIYCYETZYGVGCI-MOPGFXCFSA-N 2-methylpropanoyloxymethyl 4-[[(2S,5R)-6-(3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]piperidine-1-carboxylate Chemical compound C(C)OC(C(COS(=O)(=O)ON1[C@@H]2CC[C@H](N(C1=O)C2)C(=O)NC1CCN(CC1)C(=O)OCOC(C(C)C)=O)(C)C)=O IIYCYETZYGVGCI-MOPGFXCFSA-N 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- QVVKZTPNNZEJDV-GQXIWKRZSA-N 1-(2,2-dimethylpropanoyloxy)ethyl 4-[[(2S,5R)-6-(3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]piperidine-1-carboxylate Chemical compound C(C)OC(C(COS(=O)(=O)ON1[C@@H]2CC[C@H](N(C1=O)C2)C(=O)NC1CCN(CC1)C(=O)OC(C)OC(C(C)(C)C)=O)(C)C)=O QVVKZTPNNZEJDV-GQXIWKRZSA-N 0.000 claims description 6
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 4
- 208000022506 anaerobic bacteria infectious disease Diseases 0.000 claims description 3
- ORSUUSKLWWXEFQ-MSOLQXFVSA-N tert-butyl 4-[[(2S,5R)-6-(3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]piperidine-1-carboxylate Chemical compound C(C)OC(C(COS(=O)(=O)ON1[C@@H]2CC[C@H](N(C1=O)C2)C(=O)NC1CCN(CC1)C(=O)OC(C)(C)C)(C)C)=O ORSUUSKLWWXEFQ-MSOLQXFVSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 208000027136 gram-positive bacterial infections Diseases 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 125
- 150000001721 carbon Chemical group 0.000 description 118
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 99
- 239000000203 mixture Substances 0.000 description 92
- 239000003814 drug Substances 0.000 description 89
- 238000000034 method Methods 0.000 description 67
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 66
- 229940079593 drug Drugs 0.000 description 61
- 125000001424 substituent group Chemical group 0.000 description 60
- 125000003545 alkoxy group Chemical group 0.000 description 53
- 230000015572 biosynthetic process Effects 0.000 description 51
- 238000003786 synthesis reaction Methods 0.000 description 51
- 201000010099 disease Diseases 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 50
- 239000000047 product Substances 0.000 description 41
- 239000002552 dosage form Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- 125000000000 cycloalkoxy group Chemical group 0.000 description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 34
- 235000019439 ethyl acetate Nutrition 0.000 description 33
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 32
- 230000001225 therapeutic effect Effects 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 28
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 28
- 239000001301 oxygen Substances 0.000 description 28
- 238000011282 treatment Methods 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 229940124597 therapeutic agent Drugs 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 210000004369 blood Anatomy 0.000 description 24
- 239000008280 blood Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 108020004256 Beta-lactamase Proteins 0.000 description 22
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 22
- 239000003981 vehicle Substances 0.000 description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 21
- 210000002381 plasma Anatomy 0.000 description 21
- 229910001868 water Inorganic materials 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000003480 eluent Substances 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 17
- 229940002612 prodrug Drugs 0.000 description 17
- 239000000651 prodrug Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
- 208000035475 disorder Diseases 0.000 description 16
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 16
- 238000013268 sustained release Methods 0.000 description 16
- 239000012730 sustained-release form Substances 0.000 description 16
- 150000003952 β-lactams Chemical class 0.000 description 16
- 239000003781 beta lactamase inhibitor Substances 0.000 description 15
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 239000012453 solvate Substances 0.000 description 14
- 208000024891 symptom Diseases 0.000 description 14
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 238000001727 in vivo Methods 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003242 anti bacterial agent Substances 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 125000004405 heteroalkoxy group Chemical group 0.000 description 12
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 230000000269 nucleophilic effect Effects 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 11
- 206010028980 Neoplasm Diseases 0.000 description 11
- 230000003115 biocidal effect Effects 0.000 description 11
- 201000011510 cancer Diseases 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 10
- 244000052616 bacterial pathogen Species 0.000 description 10
- 239000006260 foam Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000003937 drug carrier Substances 0.000 description 9
- DMJPMGIRCNBTLR-UHFFFAOYSA-N ethyl 3-chlorosulfonyloxy-2,2-dimethylpropanoate Chemical compound ClS(=O)(=O)OCC(C(=O)OCC)(C)C DMJPMGIRCNBTLR-UHFFFAOYSA-N 0.000 description 9
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000000099 in vitro assay Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000012258 stirred mixture Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 230000002411 adverse Effects 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- JBDMHPJPFPMZLI-UHFFFAOYSA-N ethyl 3-hydroxy-2,2-dimethylpropanoate Chemical compound CCOC(=O)C(C)(C)CO JBDMHPJPFPMZLI-UHFFFAOYSA-N 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 125000004434 sulfur atom Chemical group 0.000 description 8
- 230000001839 systemic circulation Effects 0.000 description 8
- 231100000419 toxicity Toxicity 0.000 description 8
- 230000001988 toxicity Effects 0.000 description 8
- FHELCJGBFSCFMZ-ZJUUUORDSA-N (2S,5R)-7-oxo-N-piperidin-4-yl-1,6-diazabicyclo[3.2.1]octane-2-carboxamide Chemical compound C1C[C@H](N2C[C@@H]1NC2=O)C(=O)NC3CCNCC3 FHELCJGBFSCFMZ-ZJUUUORDSA-N 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 241000282412 Homo Species 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 238000010171 animal model Methods 0.000 description 7
- 229940088710 antibiotic agent Drugs 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 108010068385 carbapenemase Proteins 0.000 description 7
- 238000004113 cell culture Methods 0.000 description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 210000001035 gastrointestinal tract Anatomy 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- VNMDQUKZJLFBDY-UHFFFAOYSA-N heptyl 3-chlorosulfonyloxy-2,2-dimethylpropanoate Chemical compound ClS(=O)(=O)OCC(C(=O)OCCCCCCC)(C)C VNMDQUKZJLFBDY-UHFFFAOYSA-N 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 7
- LLJNZJLFGYYGKV-UHFFFAOYSA-N (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 3-chlorosulfonyloxy-2,2-dimethylpropanoate Chemical compound ClS(=O)(=O)OCC(C(=O)OCC=1OC(OC=1C)=O)(C)C LLJNZJLFGYYGKV-UHFFFAOYSA-N 0.000 description 6
- WZPBZJONDBGPKJ-VEHQQRBSSA-L 2-[(z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2s,3s)-2-methyl-4-oxo-1-sulfonatoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoate 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(N)=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-L 0.000 description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 125000002837 carbocyclic group Chemical group 0.000 description 6
- XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 6
- FHAVVFKAHOSHKD-UHFFFAOYSA-N ethyl 1-(chlorosulfonyloxymethyl)cyclohexane-1-carboxylate Chemical compound ClS(=O)(=O)OCC1(CCCCC1)C(=O)OCC FHAVVFKAHOSHKD-UHFFFAOYSA-N 0.000 description 6
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 6
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 description 6
- 230000002496 gastric effect Effects 0.000 description 6
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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| WO2009033079A1 (en) | 2007-09-07 | 2009-03-12 | Xenoport, Inc. | Externally masked neopentyl sulfonyl ester cyclization release prodrugs of acamprosate, compositions thereof, and methods of use |
| TW200924746A (en) | 2007-09-07 | 2009-06-16 | Xenoport Inc | Complex pantoic acid ester neopentyl sulfonyl ester cyclization release prodrugs of acamprosate, compositions thereof, and methods of use |
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- 2019-10-01 US US16/589,498 patent/US11180500B2/en active Active
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| JP2011510012A (ja) | 2008-01-18 | 2011-03-31 | メルク・シャープ・エンド・ドーム・コーポレイション | β−ラクタマーゼ阻害剤 |
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| JP2022511392A (ja) | 2022-01-31 |
| WO2020072442A1 (en) | 2020-04-09 |
| EP3860999B9 (en) | 2024-08-14 |
| EP3860999B1 (en) | 2024-06-05 |
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| EP3860999A1 (en) | 2021-08-11 |
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| US20200102307A1 (en) | 2020-04-02 |
| US11180500B2 (en) | 2021-11-23 |
| ES2991492T3 (es) | 2024-12-03 |
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