CA2921427A1 - Substituted hydroxamic acid compounds - Google Patents
Substituted hydroxamic acid compounds Download PDFInfo
- Publication number
- CA2921427A1 CA2921427A1 CA2921427A CA2921427A CA2921427A1 CA 2921427 A1 CA2921427 A1 CA 2921427A1 CA 2921427 A CA2921427 A CA 2921427A CA 2921427 A CA2921427 A CA 2921427A CA 2921427 A1 CA2921427 A1 CA 2921427A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- compound according
- alkoxy
- aryl
- heterocyclyl
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 389
- 239000002253 acid Substances 0.000 title description 6
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 241000894006 Bacteria Species 0.000 claims abstract description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 319
- 125000000217 alkyl group Chemical group 0.000 claims description 212
- 125000000623 heterocyclic group Chemical group 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 91
- 125000001072 heteroaryl group Chemical group 0.000 claims description 81
- -1 -ON Chemical group 0.000 claims description 76
- 239000001257 hydrogen Substances 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 75
- 125000003545 alkoxy group Chemical group 0.000 claims description 74
- 229910052736 halogen Inorganic materials 0.000 claims description 61
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 56
- 150000002367 halogens Chemical group 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- 125000001188 haloalkyl group Chemical group 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
- 150000002431 hydrogen Chemical group 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 27
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 27
- 125000002757 morpholinyl group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 102000004190 Enzymes Human genes 0.000 claims description 7
- 108090000790 Enzymes Proteins 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 125000005959 diazepanyl group Chemical group 0.000 claims description 4
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
- 241000589291 Acinetobacter Species 0.000 claims description 3
- 241000588914 Enterobacter Species 0.000 claims description 3
- 241000588921 Enterobacteriaceae Species 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 241000589513 Burkholderia cepacia Species 0.000 claims description 2
- 241000046135 Cedecea Species 0.000 claims description 2
- 241000588923 Citrobacter Species 0.000 claims description 2
- 241001445332 Coxiella <snail> Species 0.000 claims description 2
- 241000607473 Edwardsiella <enterobacteria> Species 0.000 claims description 2
- 241000588697 Enterobacter cloacae Species 0.000 claims description 2
- 241000588722 Escherichia Species 0.000 claims description 2
- 241000606790 Haemophilus Species 0.000 claims description 2
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 2
- 241000588653 Neisseria Species 0.000 claims description 2
- 241000588769 Proteus <enterobacteria> Species 0.000 claims description 2
- 241000606697 Rickettsia prowazekii Species 0.000 claims description 2
- 241000607142 Salmonella Species 0.000 claims description 2
- 241000607720 Serratia Species 0.000 claims description 2
- 241000607768 Shigella Species 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229940046939 rickettsia prowazekii Drugs 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 6
- MPUWGYBPAMDEFO-UHFFFAOYSA-N 4-[4-(4-aminophenyl)buta-1,3-diynyl]-n-[3-hydroxy-1-(hydroxyamino)-2-methyl-1-oxobutan-2-yl]benzamide Chemical compound C1=CC(C(=O)NC(C)(C(O)C)C(=O)NO)=CC=C1C#CC#CC1=CC=C(N)C=C1 MPUWGYBPAMDEFO-UHFFFAOYSA-N 0.000 claims 1
- 241000588986 Alcaligenes Species 0.000 claims 1
- 241000722910 Burkholderia mallei Species 0.000 claims 1
- 241001136175 Burkholderia pseudomallei Species 0.000 claims 1
- IKGPVJUCVRQDSI-UHFFFAOYSA-N CC(O)(C(F)F)C(C)(NC(=O)c1ccc(cc1)C#Cc1ccc(CN2CCOCC2)cc1)C(=O)NO Chemical compound CC(O)(C(F)F)C(C)(NC(=O)c1ccc(cc1)C#Cc1ccc(CN2CCOCC2)cc1)C(=O)NO IKGPVJUCVRQDSI-UHFFFAOYSA-N 0.000 claims 1
- 241000589875 Campylobacter jejuni Species 0.000 claims 1
- 241000588748 Klebsiella Species 0.000 claims 1
- 241000588915 Klebsiella aerogenes Species 0.000 claims 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims 1
- 241000122973 Stenotrophomonas maltophilia Species 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 229940074375 burkholderia mallei Drugs 0.000 claims 1
- 229940092559 enterobacter aerogenes Drugs 0.000 claims 1
- NNSZPSXJBHGUOI-UHFFFAOYSA-N n-[3-acetamido-4,4-difluoro-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide Chemical compound C1=CC(C(=O)NC(C(C)(C(F)F)NC(=O)C)C(=O)NO)=CC=C1C#CC(C=C1)=CC=C1CN1CCOCC1 NNSZPSXJBHGUOI-UHFFFAOYSA-N 0.000 claims 1
- JSIJWJKHTOHPHE-UHFFFAOYSA-N n-[3-amino-4,4-difluoro-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide Chemical compound C1=CC(C(=O)NC(C(N)(C(F)F)C)C(=O)NO)=CC=C1C#CC(C=C1)=CC=C1CN1CCOCC1 JSIJWJKHTOHPHE-UHFFFAOYSA-N 0.000 claims 1
- HKCVHALBVXMYJS-UHFFFAOYSA-N n-[4,4-difluoro-1-(hydroxyamino)-3-methoxy-3-methyl-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide Chemical compound C1=CC(C(=O)NC(C(C)(C(F)F)OC)C(=O)NO)=CC=C1C#CC(C=C1)=CC=C1CN1CCOCC1 HKCVHALBVXMYJS-UHFFFAOYSA-N 0.000 claims 1
- CISIHWLUROITKQ-UHFFFAOYSA-N n-[4,4-difluoro-1-(hydroxyamino)-3-methyl-3-(methylcarbamoylamino)-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide Chemical compound C1=CC(C(=O)NC(C(C)(C(F)F)NC(=O)NC)C(=O)NO)=CC=C1C#CC(C=C1)=CC=C1CN1CCOCC1 CISIHWLUROITKQ-UHFFFAOYSA-N 0.000 claims 1
- QNQLYOFTAZBSGC-UHFFFAOYSA-N n-[4,4-difluoro-3-hydroxy-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide Chemical compound C1=CC(C(=O)NC(C(O)(C(F)F)C)C(=O)NO)=CC=C1C#CC(C=C1)=CC=C1CN1CCOCC1 QNQLYOFTAZBSGC-UHFFFAOYSA-N 0.000 claims 1
- SQLYNXHSRIWJLS-UHFFFAOYSA-N n-hydroxy-2-methyl-2-methylsulfonyl-4-[2-oxo-4-(2-phenylethynyl)pyridin-1-yl]butanamide Chemical group O=C1N(CCC(C)(C(=O)NO)S(C)(=O)=O)C=CC(C#CC=2C=CC=CC=2)=C1 SQLYNXHSRIWJLS-UHFFFAOYSA-N 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 abstract description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 24
- 239000000203 mixture Substances 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 17
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- 125000005605 benzo group Chemical group 0.000 description 10
- HJZVHUQSQGITAM-UHFFFAOYSA-N butanamide Chemical compound CC[CH]C(N)=O HJZVHUQSQGITAM-UHFFFAOYSA-N 0.000 description 10
- 241000534944 Thia Species 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 230000000063 preceeding effect Effects 0.000 description 9
- 125000002619 bicyclic group Chemical group 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 241000282414 Homo sapiens Species 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000002207 metabolite Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 229950006780 n-acetylglucosamine Drugs 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000002759 chromosomal effect Effects 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000000844 transformation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 241001473877 Biserrula isolate Species 0.000 description 2
- 241001453380 Burkholderia Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- 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 2
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 2
- 241000607626 Vibrio cholerae Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
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- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003828 azulenyl group Chemical group 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
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- 239000000872 buffer Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 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 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- SONSSPAQDOLYEQ-UHFFFAOYSA-N heptanamide Chemical compound CCCCC[CH]C(N)=O SONSSPAQDOLYEQ-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 239000013612 plasmid Substances 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
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- 231100000419 toxicity Toxicity 0.000 description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- ILWJAOPQHOZXAN-UHFFFAOYSA-N 1,3-dithianyl Chemical group [CH]1SCCCS1 ILWJAOPQHOZXAN-UHFFFAOYSA-N 0.000 description 1
- FLOJNXXFMHCMMR-UHFFFAOYSA-N 1,3-dithiolanyl Chemical group [CH]1SCCS1 FLOJNXXFMHCMMR-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004564 2,3-dihydrobenzofuran-2-yl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000004565 2,3-dihydrobenzofuran-4-yl group Chemical group O1CCC2=C1C=CC=C2* 0.000 description 1
- 125000004563 2,3-dihydroindol-5-yl group Chemical group N1CCC2=CC(=CC=C12)* 0.000 description 1
- 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 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 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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- 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pyridine Compounds (AREA)
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| US201361867933P | 2013-08-20 | 2013-08-20 | |
| US61/867,933 | 2013-08-20 | ||
| PCT/US2014/051459 WO2015024010A2 (en) | 2013-08-16 | 2014-08-18 | Substituted hydroxamic acid compounds |
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| EP (1) | EP3041354A4 (enExample) |
| JP (2) | JP6458270B2 (enExample) |
| AU (1) | AU2014306451B2 (enExample) |
| CA (1) | CA2921427A1 (enExample) |
| WO (1) | WO2015024010A2 (enExample) |
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| US10647664B2 (en) * | 2013-08-16 | 2020-05-12 | Duke University | Substituted hydroxamic acid compounds |
| EP3143007B1 (en) | 2014-05-16 | 2018-07-11 | Idorsia Pharmaceuticals Ltd | Antibacterial quinazoline-4(3h)-one derivatives |
| WO2017083434A1 (en) | 2015-11-09 | 2017-05-18 | Forge Therapeutics, Inc. | Pyrone based compounds for treating bacterial infections |
| WO2017083431A2 (en) | 2015-11-09 | 2017-05-18 | Forge Therapeutics, Inc. | Hydroxypyridinone and hydroxypyrimidinone based compounds for treating bacterial infections |
| EP3448375B1 (en) * | 2016-04-25 | 2023-09-27 | Duke University | Benzoylglycine derivatives and methods of making and using same |
| WO2018115421A1 (en) * | 2016-12-23 | 2018-06-28 | Intervet International B.V. | Compounds useful for treating a mannheimia haemolytica or histophilus somni infection |
| EP3621962A4 (en) | 2017-05-10 | 2020-12-09 | Forge Therapeutics, Inc. | ANTIBACTERIAL COMPOUNDS |
| BR112020016270A2 (pt) * | 2018-02-10 | 2020-12-15 | Kbp Biosciences Co., Ltd. | Composto atuando como antibióticos |
| CA3113226A1 (en) * | 2018-09-20 | 2020-03-26 | Forge Therapeutics, Inc. | Antibacterial compounds |
| US12617767B2 (en) | 2019-07-17 | 2026-05-05 | Crinetics Pharmaceuticals, Inc. | Crystalline forms of somatostatin modulators |
| WO2021195260A1 (en) | 2020-03-25 | 2021-09-30 | Forge Therapeutics, Inc. | Lpxc inhibitor and methods of making |
| WO2022055880A1 (en) | 2020-09-09 | 2022-03-17 | Crinetics Pharmaceuticals, Inc. | Formulations of a somatostatin modulator |
| CA3233328A1 (en) | 2021-09-28 | 2023-04-06 | Min Teng | Lpxc inhibitors and uses thereof |
| US20260102415A1 (en) * | 2022-10-05 | 2026-04-16 | Duke University | Compositions comprising prodrugs of hydroxamate-based compounds and methods of making and using same |
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| WO1993014077A1 (en) | 1992-01-21 | 1993-07-22 | Glaxo Group Limited | Piperidineacetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation |
| TW448172B (en) | 1996-03-08 | 2001-08-01 | Pharmacia & Upjohn Co Llc | Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation |
| US5925659A (en) | 1996-05-07 | 1999-07-20 | Merck & Co., Inc. | Antibacterial agents |
| GB9725782D0 (en) | 1997-12-05 | 1998-02-04 | Pfizer Ltd | Therapeutic agents |
| JP2000344752A (ja) * | 1999-04-01 | 2000-12-12 | Sumitomo Pharmaceut Co Ltd | 点眼剤 |
| US6511993B1 (en) | 1999-06-03 | 2003-01-28 | Kevin Neil Dack | Metalloprotease inhibitors |
| ATE510817T1 (de) * | 2002-01-29 | 2011-06-15 | Merck Serono Sa | Substituierte methylenamidderivate als modulatoren von proteintyrosinphosphatasen (ptps) |
| BR0309671A (pt) | 2002-04-25 | 2005-05-03 | Pharmacia Corp | ácidos de piperidinil- e piperazinil-sulfonilmetil hidroxâmicos e seu uso como inibidores de protease |
| AU2003267991B2 (en) | 2002-07-11 | 2009-10-08 | Vicuron Pharmaceuticals, Inc. | N-hydroxyamide derivatives possessing antibacterial activity |
| SG159388A1 (en) | 2003-01-08 | 2010-03-30 | Chiron Corp | Antibacterial agents |
| US20050154022A1 (en) | 2004-01-14 | 2005-07-14 | H. Lundbeck A/S | 4-aryl piperidines |
| US7638513B2 (en) | 2004-06-02 | 2009-12-29 | Schering Corporation | Compounds for the treatment of inflammatory disorders |
| AT502219B1 (de) | 2005-08-04 | 2007-04-15 | Sanochemia Pharmazeutika Ag | Verfahren zur reindarstellung von 5-substituierten tetrazolen |
| US7553864B2 (en) | 2005-12-01 | 2009-06-30 | Schering Corporation | Compounds for the treatment of inflammatory disorders and microbial diseases |
| JP2010502617A (ja) | 2006-08-31 | 2010-01-28 | シェーリング コーポレイション | 抗菌物質として有用なヒダントイン誘導体 |
| JP5227304B2 (ja) | 2007-02-28 | 2013-07-03 | 大正製薬株式会社 | 新規なヒドロキサム酸誘導体 |
| CA2934114A1 (en) | 2007-06-12 | 2008-12-18 | Achaogen, Inc. | Antibacterial agents |
| WO2009158369A1 (en) | 2008-06-25 | 2009-12-30 | Schering Corporation | Synthesis and use of heterocyclic antibacterial agents |
| EP2315746A1 (en) | 2008-08-04 | 2011-05-04 | Schering Corporation | Urea derivatives as antibacterial agents |
| JP5455913B2 (ja) | 2008-08-27 | 2014-03-26 | 大正製薬株式会社 | ナフチリジン−ｎ−オキシドを有する新規ヒドロキサム酸誘導体 |
| US8372885B2 (en) | 2008-09-17 | 2013-02-12 | Novartis Ag | Organic compounds and their uses |
| WO2010100475A1 (en) | 2009-03-02 | 2010-09-10 | Astrazeneca Ab | Hydroxamic acid derivatives as gram-negative antibacterial agents |
| WO2011005355A1 (en) | 2009-05-07 | 2011-01-13 | Achaogen, Inc. | Combinations comprising a lpxc inhibitor and an antibiotic for use in the treatment of infections caused by gram-negative bacteria |
| CA2774250C (en) * | 2009-10-13 | 2013-12-17 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| US8389536B2 (en) | 2009-10-27 | 2013-03-05 | Hoffmann-La Roche Inc. | Positive allosteric modulators (PAM) |
| PL2512474T3 (pl) | 2009-12-16 | 2015-03-31 | Pfizer | N-przyłączone pochodne kwasu hydroksamowego użyteczne jako środki przeciwbakteryjne |
| SG184958A1 (en) * | 2010-04-20 | 2012-11-29 | Taisho Pharmaceutical Co Ltd | Novel hydroxamic acid derivative |
| WO2012031298A2 (en) | 2010-09-03 | 2012-03-08 | Duke University | Ethynylbenzene derivatives |
| US8772300B2 (en) * | 2011-04-19 | 2014-07-08 | Hoffmann-La Roche Inc. | Phenyl or pyridinyl-ethynyl derivatives |
| WO2013049255A1 (en) * | 2011-09-26 | 2013-04-04 | Vanderbilt University | Substitued 5-(prop-1-yn-1-yl)picolinamide analogs as allosteric modulators of mglur5 receptors |
| JP6006609B2 (ja) * | 2011-10-19 | 2016-10-12 | 大正製薬株式会社 | 新規なヒドロキサム酸誘導体を含有する医薬 |
| EP2847168A1 (en) * | 2012-05-10 | 2015-03-18 | Achaogen, Inc. | Antibacterial agents |
| LT2975022T (lt) * | 2013-03-15 | 2019-07-25 | Fujifilm Toyama Chemical Co., Ltd. | Naujas hidroksamo rūgšties darinys arba jo druska |
| US10647664B2 (en) * | 2013-08-16 | 2020-05-12 | Duke University | Substituted hydroxamic acid compounds |
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2015024010A3 (en) | 2015-04-16 |
| JP2019077688A (ja) | 2019-05-23 |
| WO2015024010A2 (en) | 2015-02-19 |
| EP3041354A4 (en) | 2017-06-14 |
| JP6458270B2 (ja) | 2019-01-30 |
| US20160221934A1 (en) | 2016-08-04 |
| JP2016535758A (ja) | 2016-11-17 |
| AU2014306451A1 (en) | 2016-03-03 |
| EP3041354A2 (en) | 2016-07-13 |
| AU2014306451B2 (en) | 2019-01-17 |
| US10647664B2 (en) | 2020-05-12 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
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| FZDE | Discontinued |
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