ES2991492T3 - Derivados de relebactam y usos de los mismos - Google Patents
Derivados de relebactam y usos de los mismos Download PDFInfo
- Publication number
- ES2991492T3 ES2991492T3 ES19787552T ES19787552T ES2991492T3 ES 2991492 T3 ES2991492 T3 ES 2991492T3 ES 19787552 T ES19787552 T ES 19787552T ES 19787552 T ES19787552 T ES 19787552T ES 2991492 T3 ES2991492 T3 ES 2991492T3
- Authority
- ES
- Spain
- 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 abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 118
- 150000001875 compounds Chemical class 0.000 claims description 854
- 125000000217 alkyl group Chemical group 0.000 claims description 371
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 233
- 229910052739 hydrogen Inorganic materials 0.000 claims description 194
- 239000001257 hydrogen Substances 0.000 claims description 194
- -1 (3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyl Chemical group 0.000 claims description 191
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 136
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 134
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 132
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 129
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 126
- 229910052799 carbon Inorganic materials 0.000 claims description 122
- 125000003118 aryl group Chemical group 0.000 claims description 121
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 90
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 87
- 125000001072 heteroaryl group Chemical group 0.000 claims description 85
- 150000003839 salts Chemical class 0.000 claims description 84
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 77
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 73
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 53
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 47
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 46
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 46
- 208000035143 Bacterial infection Diseases 0.000 claims description 43
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 43
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 38
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 35
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 29
- 230000003115 biocidal effect Effects 0.000 claims description 28
- 239000006186 oral dosage form Substances 0.000 claims description 28
- 239000003937 drug carrier Substances 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 21
- 239000003242 anti bacterial agent Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims 8
- 239000003782 beta lactam antibiotic agent Substances 0.000 abstract description 7
- 238000002560 therapeutic procedure Methods 0.000 abstract description 5
- 239000002132 β-lactam antibiotic Substances 0.000 abstract 1
- 229940124586 β-lactam antibiotics Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 132
- 150000001721 carbon Chemical group 0.000 description 113
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 97
- 239000003814 drug Substances 0.000 description 82
- 230000015572 biosynthetic process Effects 0.000 description 72
- 238000003786 synthesis reaction Methods 0.000 description 70
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 69
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 64
- 239000000243 solution Substances 0.000 description 62
- 239000000047 product Substances 0.000 description 59
- 125000001424 substituent group Chemical group 0.000 description 58
- 229940079593 drug Drugs 0.000 description 54
- 201000010099 disease Diseases 0.000 description 53
- 125000005842 heteroatom Chemical group 0.000 description 53
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 50
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 49
- 235000019439 ethyl acetate Nutrition 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 46
- 125000003545 alkoxy group Chemical group 0.000 description 43
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 42
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 39
- 239000002552 dosage form Substances 0.000 description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 33
- 230000001225 therapeutic effect Effects 0.000 description 33
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 31
- 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 30
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 30
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 28
- 239000001301 oxygen Substances 0.000 description 28
- 125000000000 cycloalkoxy group Chemical group 0.000 description 27
- 239000003480 eluent Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- UAXPWIIIZNAMSN-CABCVRRESA-N ethyl 2,2-dimethyl-3-[[(2S,5R)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl]oxysulfonyloxy]propanoate Chemical compound C(C)OC(C(COS(=O)(=O)ON1[C@@H]2CC[C@H](N(C1=O)C2)C(NC1CCNCC1)=O)(C)C)=O UAXPWIIIZNAMSN-CABCVRRESA-N 0.000 description 25
- 229940124597 therapeutic agent Drugs 0.000 description 25
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 23
- 210000004369 blood Anatomy 0.000 description 23
- 239000008280 blood Substances 0.000 description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000706 filtrate Substances 0.000 description 22
- 229950011310 relebactam Drugs 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 238000013268 sustained release Methods 0.000 description 21
- 239000012730 sustained-release form Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 241000894006 Bacteria Species 0.000 description 20
- 210000002381 plasma Anatomy 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
- 108090000790 Enzymes Proteins 0.000 description 17
- 102000004190 Enzymes Human genes 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 17
- 208000035475 disorder Diseases 0.000 description 16
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 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 description 16
- 238000009472 formulation Methods 0.000 description 15
- 229940002612 prodrug Drugs 0.000 description 15
- 239000000651 prodrug Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000012258 stirred mixture Substances 0.000 description 15
- 208000024891 symptom Diseases 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 239000012453 solvate Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 125000004122 cyclic group Chemical group 0.000 description 13
- 238000001727 in vivo Methods 0.000 description 13
- 239000003112 inhibitor Substances 0.000 description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 230000002411 adverse Effects 0.000 description 12
- 239000012267 brine Substances 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
- 230000000269 nucleophilic effect Effects 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 11
- 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
- 201000011510 cancer Diseases 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 10
- 241000282412 Homo Species 0.000 description 10
- 239000006260 foam Substances 0.000 description 10
- UDTUWSBTBPKKSP-UHFFFAOYSA-N hexyl 3-chlorosulfonyloxy-2,2-dimethylpropanoate Chemical compound ClS(=O)(=O)OCC(C(=O)OCCCCCC)(C)C UDTUWSBTBPKKSP-UHFFFAOYSA-N 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
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 208000015181 infectious disease Diseases 0.000 description 9
- WTKPJSROYKRESH-MSOLQXFVSA-N (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 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)OCC=1OC(OC=1C)=O)(C)C)=O WTKPJSROYKRESH-MSOLQXFVSA-N 0.000 description 8
- GQSZUUPRBBBHRI-UHFFFAOYSA-N 2,2-dimethylbutane-1,4-diol Chemical compound OCC(C)(C)CCO GQSZUUPRBBBHRI-UHFFFAOYSA-N 0.000 description 8
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 8
- 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 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
- AGZKZFGNNOGMLZ-UHFFFAOYSA-N hexyl 3-hydroxy-2,2-dimethylpropanoate Chemical compound CCCCCCOC(=O)C(C)(C)CO AGZKZFGNNOGMLZ-UHFFFAOYSA-N 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 230000000144 pharmacologic effect Effects 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000004434 sulfur atom Chemical group 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 230000001839 systemic circulation Effects 0.000 description 8
- IDAZPRDVYYFZMS-KZCZEQIWSA-N tert-butyl 4-[[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]piperidine-1-carboxylate hydrate Chemical compound O.ON1[C@@H]2CC[C@H](N(C1=O)C2)C(=O)NC1CCN(CC1)C(=O)OC(C)(C)C IDAZPRDVYYFZMS-KZCZEQIWSA-N 0.000 description 8
- 231100000419 toxicity Toxicity 0.000 description 8
- 230000001988 toxicity Effects 0.000 description 8
- QLLNUAHVXVPAIK-VITQDTLGSA-N 1-acetyloxyethyl 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)=O)(C)C)=O QLLNUAHVXVPAIK-VITQDTLGSA-N 0.000 description 7
- QCNSJUVSPXFSPR-MOPGFXCFSA-N 2,2-dimethylpropanoyloxymethyl 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)C)=O)(C)C)=O QCNSJUVSPXFSPR-MOPGFXCFSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 238000010171 animal model Methods 0.000 description 7
- 238000004113 cell culture Methods 0.000 description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 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
- XLZYKTYMLBOINK-UHFFFAOYSA-N 3-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC(O)=CC=2)=C1 XLZYKTYMLBOINK-UHFFFAOYSA-N 0.000 description 6
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 229930186147 Cephalosporin Natural products 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
- 229940123930 Lactamase inhibitor Drugs 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-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
- 229940088710 antibiotic agent Drugs 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 6
- 125000000732 arylene group Chemical group 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- 244000052616 bacterial pathogen Species 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
- 229940124587 cephalosporin Drugs 0.000 description 6
- 150000001780 cephalosporins Chemical class 0.000 description 6
- 150000001781 cephams Chemical class 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
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- 239000002699 waste material Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- KGPGQDLTDHGEGT-JCIKCJKQSA-N zeven Chemical compound C=1C([C@@H]2C(=O)N[C@H](C(N[C@H](C3=CC(O)=C4)C(=O)NCCCN(C)C)=O)[C@H](O)C5=CC=C(C(=C5)Cl)OC=5C=C6C=C(C=5O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@H](O5)C(O)=O)NC(=O)CCCCCCCCC(C)C)OC5=CC=C(C=C5)C[C@@H]5C(=O)N[C@H](C(N[C@H]6C(=O)N2)=O)C=2C(Cl)=C(O)C=C(C=2)OC=2C(O)=CC=C(C=2)[C@H](C(N5)=O)NC)=CC=C(O)C=1C3=C4O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O KGPGQDLTDHGEGT-JCIKCJKQSA-N 0.000 description 1
Classifications
-
- 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
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862739746P | 2018-10-01 | 2018-10-01 | |
| PCT/US2019/053990 WO2020072442A1 (en) | 2018-10-01 | 2019-10-01 | Derivatives of relebactam and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2991492T3 true ES2991492T3 (es) | 2024-12-03 |
Family
ID=68242885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES19787552T Active ES2991492T3 (es) | 2018-10-01 | 2019-10-01 | Derivados de relebactam y usos de los mismos |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11180500B2 (https=) |
| EP (1) | EP3860999B9 (https=) |
| JP (1) | JP7437847B2 (https=) |
| CA (1) | CA3114618C (https=) |
| ES (1) | ES2991492T3 (https=) |
| WO (1) | WO2020072442A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN119431373B (zh) * | 2024-07-24 | 2025-08-08 | 科睿迪(南京)医药科技有限公司 | 一种β-内酰胺酶抑制剂及其用途 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658849A (en) | 1969-02-19 | 1972-04-25 | Reynolds Tobacco Co R | Treatment of 2-substituted aldehydes with lead dioxide |
| DE3045373A1 (de) | 1980-12-02 | 1982-07-01 | Henkel KGaA, 4000 Düsseldorf | Verwendung von estern der 3-hydrody-2,2-dimethylpropionsaeure als riechstoffe, diese enthaltende riechstoffkompositionen und 3-hydroxy-2,2-dimethyl-propionsaeurepropylester |
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| IT1270594B (it) | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| TR200003199T2 (tr) * | 1998-05-01 | 2001-03-21 | Kyoto Pharmaceutical Industries, Ltd. | Karbapenem türevleri, bunların kullanımı ve ara birleşiği |
| FR2812635B1 (fr) | 2000-08-01 | 2002-10-11 | Aventis Pharma Sa | Nouveaux composes heterocycliques, preparation et utilisation comme medicaments notamment comme anti- bacteriens |
| WO2002092606A1 (en) | 2001-05-15 | 2002-11-21 | Takeda Chemical Industries, Ltd. | Fused imidazolidine derivatives, process for preparation of the same and use thereof |
| WO2009151392A1 (en) | 2008-06-14 | 2009-12-17 | Astrazeneca Ab | Novel derivatives of 11-piperazin-l-yldibenzo [b,f] [1,4] thiazepine for treating at least one syndrome or condition associated with schizophrenia and other psychotic disorders |
| TW200808731A (en) | 2006-03-30 | 2008-02-16 | Tanabe Seiyaku Co | A process for preparing tetrahydroquinoline derivatives |
| US20090082464A1 (en) | 2007-09-07 | 2009-03-26 | Bernd Jandeleit | Externally masked neopentyl sulfonyl ester cyclization release prodrugs of acamprosate, compositions thereof, and methods of use |
| EP2217564A1 (en) | 2007-09-07 | 2010-08-18 | XenoPort, Inc. | Complex pantoic acid ester neopentyl sulfonyl ester cyclization release prodrugs of acamprosate, compositions thereof, and methods of use |
| US20090099253A1 (en) | 2007-10-15 | 2009-04-16 | Xenoport, Inc. | Internally Masked Neopentyl Sulfonyl Ester Cyclization Release Prodrugs of Acamprosate, Compositions Thereof, and Methods of Use |
| WO2009091856A2 (en) | 2008-01-18 | 2009-07-23 | Merck & Co., Inc. | Beta-lactamase inhibitors |
| GB0801401D0 (en) | 2008-01-25 | 2008-03-05 | Barry Callebaut Ag | Composition |
| WO2009100045A1 (en) | 2008-02-04 | 2009-08-13 | Translational Genomics Research Institute | Compounds, pharmaceutical compositions and methods of use of hydroxamic acid derivatives |
| WO2010032147A2 (en) | 2008-09-19 | 2010-03-25 | Pfizer Inc. | Hydroxamic acid derivatives useful as antibacterial agents |
| WO2010065709A2 (en) | 2008-12-03 | 2010-06-10 | Amin Khan | Hydroxamic acid derivatives, preparation and therapeutic uses thereof |
| US20120053350A1 (en) * | 2009-04-30 | 2012-03-01 | Ian Mangion | Preparation of alkyl esters of n-protected oxo-azacycloalkylcarboxylic acids |
| US8859776B2 (en) | 2009-10-14 | 2014-10-14 | Merck Sharp & Dohme Corp. | Substituted piperidines that increase p53 activity and the uses thereof |
| CA2796750C (en) | 2010-04-20 | 2017-09-19 | Taisho Pharmaceutical Co., Ltd. | Novel hydroxamic acid derivative |
| WO2011150380A1 (en) | 2010-05-28 | 2011-12-01 | Xenoport, Inc. | Methods of treatment of fragile x syndrome, down's syndrome, autism and related disorders |
| US8772490B2 (en) | 2010-12-22 | 2014-07-08 | Meiji Seika Pharma Co., Ltd. | Optically active diazabicyclooctane derivatives and process for preparing the same |
| PL2657234T3 (pl) | 2010-12-22 | 2017-06-30 | Meiji Seika Pharma Co., Ltd. | Optycznie czynna pochodna diazabicyklooktanowa i sposób jej wytwarzania |
| HUE027447T2 (en) | 2011-05-30 | 2016-09-28 | Sumitomo Chemical Co | Cyclohexanone compounds and herbicides containing them |
| US8796257B2 (en) | 2011-12-02 | 2014-08-05 | Naeja Pharmaceutical Inc. | Bicyclic compounds and their use as antibacterial agents and β-lactamase inhibitors |
| BR112017004796A2 (pt) | 2014-09-12 | 2017-12-12 | Toyama Chemical Co Ltd | método para utilizar derivados de ácido hidroxâmico e substância antibacterial em combinação |
| RU2017112319A (ru) | 2014-09-12 | 2018-10-12 | Тояма Кемикал Ко., Лтд. | Новая фармацевтическая композиция, содержащая производное гидроксамовой кислоты или его соль |
| WO2016116788A1 (en) | 2015-01-24 | 2016-07-28 | Wockhardt Limited | Nitrogen containing bicyclic compounds and their use in treatment of bacterial infections |
| EP3281942A4 (en) | 2015-09-16 | 2018-08-15 | Xuanzhu Pharma Co., Ltd. | B-lactamase inhibitor and application thereof |
| US20170165371A1 (en) | 2017-02-22 | 2017-06-15 | Joel Steven Goldberg | Novel synthesis of potential ester prodrugs |
| US10085999B1 (en) | 2017-05-10 | 2018-10-02 | Arixa Pharmaceuticals, Inc. | Beta-lactamase inhibitors and uses thereof |
| EP3676247B8 (en) | 2017-10-02 | 2023-04-12 | Arixa Pharmaceuticals, Inc. | Aztreonam derivatives and uses thereof |
-
2019
- 2019-10-01 CA CA3114618A patent/CA3114618C/en active Active
- 2019-10-01 EP EP19787552.9A patent/EP3860999B9/en active Active
- 2019-10-01 JP JP2021517784A patent/JP7437847B2/ja active Active
- 2019-10-01 WO PCT/US2019/053990 patent/WO2020072442A1/en not_active Ceased
- 2019-10-01 ES ES19787552T patent/ES2991492T3/es active Active
- 2019-10-01 US US16/589,498 patent/US11180500B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP3860999C0 (en) | 2024-06-05 |
| EP3860999A1 (en) | 2021-08-11 |
| CA3114618C (en) | 2023-09-05 |
| US11180500B2 (en) | 2021-11-23 |
| JP7437847B2 (ja) | 2024-02-26 |
| WO2020072442A1 (en) | 2020-04-09 |
| JP2022511392A (ja) | 2022-01-31 |
| EP3860999B9 (en) | 2024-08-14 |
| CA3114618A1 (en) | 2020-04-09 |
| EP3860999B1 (en) | 2024-06-05 |
| US20200102307A1 (en) | 2020-04-02 |
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