AU2014306451B2 - Substituted hydroxamic acid compounds - Google Patents
Substituted hydroxamic acid compounds Download PDFInfo
- Publication number
- AU2014306451B2 AU2014306451B2 AU2014306451A AU2014306451A AU2014306451B2 AU 2014306451 B2 AU2014306451 B2 AU 2014306451B2 AU 2014306451 A AU2014306451 A AU 2014306451A AU 2014306451 A AU2014306451 A AU 2014306451A AU 2014306451 B2 AU2014306451 B2 AU 2014306451B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- heteroaryl
- aryl
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 225
- 239000002253 acid Substances 0.000 title description 7
- 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 14
- 125000000217 alkyl group Chemical group 0.000 claims description 252
- 125000003545 alkoxy group Chemical group 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 125000001072 heteroaryl group Chemical group 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 33
- 125000001188 haloalkyl group Chemical group 0.000 claims description 32
- 150000002367 halogens Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 241000894006 Bacteria Species 0.000 claims description 10
- 241000588724 Escherichia coli Species 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 102000004190 Enzymes Human genes 0.000 claims description 7
- 108090000790 Enzymes Proteins 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
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- 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 4
- 241001673062 Achromobacter xylosoxidans Species 0.000 claims description 2
- 241000589291 Acinetobacter Species 0.000 claims description 2
- 241000589513 Burkholderia cepacia Species 0.000 claims description 2
- 241000722910 Burkholderia mallei Species 0.000 claims description 2
- 241001136175 Burkholderia pseudomallei Species 0.000 claims description 2
- 241000589875 Campylobacter jejuni Species 0.000 claims description 2
- 241000046135 Cedecea Species 0.000 claims description 2
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- 241000588923 Citrobacter Species 0.000 claims description 2
- 241000607473 Edwardsiella <enterobacteria> Species 0.000 claims description 2
- 241000588914 Enterobacter Species 0.000 claims description 2
- 241000588697 Enterobacter cloacae Species 0.000 claims description 2
- 241000589602 Francisella tularensis Species 0.000 claims description 2
- 241000606790 Haemophilus Species 0.000 claims description 2
- 241000588748 Klebsiella Species 0.000 claims description 2
- 241000588915 Klebsiella aerogenes Species 0.000 claims description 2
- 241000588771 Morganella <proteobacterium> Species 0.000 claims description 2
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- 241000607142 Salmonella Species 0.000 claims description 2
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- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 229940074375 burkholderia mallei Drugs 0.000 claims description 2
- 229940038705 chlamydia trachomatis Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
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- 229940118764 francisella tularensis Drugs 0.000 claims description 2
- 229940046939 rickettsia prowazekii Drugs 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 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
- 241001445332 Coxiella <snail> Species 0.000 claims 1
- 241000588655 Moraxella catarrhalis Species 0.000 claims 1
- 241000122973 Stenotrophomonas maltophilia Species 0.000 claims 1
- -1 ary!(Ci-C6 alkyl) Chemical group 0.000 description 66
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 24
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 23
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 17
- 229910002092 carbon dioxide Inorganic materials 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- 125000002950 monocyclic group Chemical group 0.000 description 12
- HJZVHUQSQGITAM-UHFFFAOYSA-N butanamide Chemical compound CC[CH]C(N)=O HJZVHUQSQGITAM-UHFFFAOYSA-N 0.000 description 11
- 201000010099 disease Diseases 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 241000534944 Thia Species 0.000 description 9
- 125000005605 benzo group Chemical group 0.000 description 9
- 125000002619 bicyclic group Chemical group 0.000 description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 230000000063 preceeding effect Effects 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
- 125000002757 morpholinyl group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 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
- 239000003814 drug Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 6
- 239000002207 metabolite Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 125000004193 piperazinyl group Chemical group 0.000 description 5
- 125000003386 piperidinyl group Chemical group 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
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- 125000005842 heteroatom Chemical group 0.000 description 4
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- 230000001225 therapeutic effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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- 241000588088 Francisella tularensis subsp. novicida U112 Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000588652 Neisseria gonorrhoeae Species 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
- 125000002393 azetidinyl group Chemical group 0.000 description 3
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- 125000001624 naphthyl group Chemical group 0.000 description 3
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
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- 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
- 241001302584 Escherichia coli str. K-12 substr. W3110 Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000907681 Morpho Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- SONSSPAQDOLYEQ-UHFFFAOYSA-N heptanamide Chemical compound CCCCC[CH]C(N)=O SONSSPAQDOLYEQ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (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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| WO (1) | WO2015024010A2 (cg-RX-API-DMAC7.html) |
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| EP3041354A4 (en) * | 2013-08-16 | 2017-06-14 | Duke University | Substituted hydroxamic acid compounds |
| CA2948077A1 (en) | 2014-05-16 | 2015-11-19 | Actelion Pharmaceuticals Ltd | Antibacterial quinazoline-4(3h)-one derivatives |
| ES2909122T3 (es) | 2015-11-09 | 2022-05-05 | Forge Therapeutics Inc | Compuestos a base de hidroxipiridinona e hidroxipirimidinona para el tratamiento de infecciones bacterianas |
| US10611747B2 (en) | 2015-11-09 | 2020-04-07 | Forge Therapeutics, Inc. | Pyrone based compounds for treating bacterial infections |
| AU2017257755B2 (en) * | 2016-04-25 | 2021-05-06 | 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 |
| US11021471B2 (en) | 2017-05-10 | 2021-06-01 | Forge Therapeutics, Inc. | Antibacterial compounds |
| CA3090833A1 (en) * | 2018-02-10 | 2019-08-15 | Kbp Biosciences Co., Ltd. | Compound acting as antibiotics |
| CA3113226A1 (en) * | 2018-09-20 | 2020-03-26 | Forge Therapeutics, Inc. | Antibacterial compounds |
| WO2021195260A1 (en) | 2020-03-25 | 2021-09-30 | Forge Therapeutics, Inc. | Lpxc inhibitor and methods of making |
| MA66139B1 (fr) | 2020-09-09 | 2025-09-30 | Crinetics Pharmaceuticals, Inc. | Formulations d'un modulateur de somatostatine |
| JP2024536864A (ja) | 2021-09-28 | 2024-10-08 | ブラックスミス メディシンズ，インク． | Ｌｐｘｃ阻害剤およびその使用 |
| WO2024077160A2 (en) * | 2022-10-05 | 2024-04-11 | Duke University | Compositions comprising prodrugs of hydroxyamate-based compounds and methods of making and using same |
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| 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 |
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- 2014-08-18 AU AU2014306451A patent/AU2014306451B2/en not_active Ceased
- 2014-08-18 CA CA2921427A patent/CA2921427A1/en not_active Abandoned
- 2014-08-18 US US14/912,134 patent/US10647664B2/en not_active Expired - Fee Related
- 2014-08-18 JP JP2016534884A patent/JP6458270B2/ja not_active Expired - Fee Related
- 2014-08-18 WO PCT/US2014/051459 patent/WO2015024010A2/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2016535758A (ja) | 2016-11-17 |
| WO2015024010A3 (en) | 2015-04-16 |
| JP2019077688A (ja) | 2019-05-23 |
| WO2015024010A2 (en) | 2015-02-19 |
| AU2014306451A1 (en) | 2016-03-03 |
| CA2921427A1 (en) | 2015-02-19 |
| EP3041354A4 (en) | 2017-06-14 |
| US20160221934A1 (en) | 2016-08-04 |
| EP3041354A2 (en) | 2016-07-13 |
| JP6458270B2 (ja) | 2019-01-30 |
| US10647664B2 (en) | 2020-05-12 |
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