UA76059C2 - Compounds used for treating anthrax or inhibiting lethal factor - Google Patents
Compounds used for treating anthrax or inhibiting lethal factor Download PDFInfo
- Publication number
- UA76059C2 UA76059C2 UA20041210878A UA20041210878A UA76059C2 UA 76059 C2 UA76059 C2 UA 76059C2 UA 20041210878 A UA20041210878 A UA 20041210878A UA 20041210878 A UA20041210878 A UA 20041210878A UA 76059 C2 UA76059 C2 UA 76059C2
- Authority
- UA
- Ukraine
- Prior art keywords
- amino
- fluoro
- methylphenylsulfonyl
- hydroxy
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 65
- 231100000518 lethal Toxicity 0.000 title claims abstract description 28
- 230000001665 lethal effect Effects 0.000 title claims abstract description 28
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 6
- 241000193738 Bacillus anthracis Species 0.000 title abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000003937 drug carrier Substances 0.000 claims abstract description 4
- -1 nitro, amino Chemical group 0.000 claims description 49
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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- 229940079593 drug Drugs 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- DHSUYTOATWAVLW-WFVMDLQDSA-N cilastatin Chemical compound CC1(C)C[C@@H]1C(=O)N\C(=C/CCCCSC[C@H](N)C(O)=O)C(O)=O DHSUYTOATWAVLW-WFVMDLQDSA-N 0.000 claims description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- 150000001413 amino acids Chemical class 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 claims description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
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- 229960003081 probenecid Drugs 0.000 claims description 3
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
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- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- LSYHYRZLEVTRSL-UHFFFAOYSA-N 2-amino-2-(oxan-4-yl)acetamide Chemical compound NC(=O)C(N)C1CCOCC1 LSYHYRZLEVTRSL-UHFFFAOYSA-N 0.000 claims 1
- KIBXQUHWYAUSKP-UHFFFAOYSA-N 4,6,6-trimethylbicyclo[3.1.1]hept-2-yne Chemical compound C12C(C#CC(C1(C)C)C2)C KIBXQUHWYAUSKP-UHFFFAOYSA-N 0.000 claims 1
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- 208000022338 anthrax infection Diseases 0.000 abstract description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/31—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
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ES2323527T3 (es) | 2002-05-29 | 2009-07-20 | MERCK & CO., INC. | Compuestos utiles en el tratamiento del carbunco y en la inhibicion del factor letal. |
US7601351B1 (en) | 2002-06-26 | 2009-10-13 | Human Genome Sciences, Inc. | Antibodies against protective antigen |
CA2566191A1 (en) * | 2004-05-11 | 2005-12-15 | Merck & Co., Inc. | Process for making n-sulfonated-amino acid derivatives |
ITFI20040174A1 (it) * | 2004-08-03 | 2004-11-03 | Protera S R L | Derivati arilsolfonammidici dell'acido idrossammico ad azione inibitoria di metalloproteinasi |
US20100003276A1 (en) * | 2004-12-07 | 2010-01-07 | Hermes Jeffery D | Methods for treating anthrax and inhibiting lethal factor |
EP2597083A3 (en) * | 2006-03-29 | 2014-09-17 | Novartis AG | Selective hydroxamate based MMP inhibitors |
US8242174B2 (en) | 2007-02-01 | 2012-08-14 | Panthera Biopharma Llc | Hydroxamic acid derivatives of aniline useful as therapeutic agents for treating anthrax poisoning |
US7807720B2 (en) | 2007-02-01 | 2010-10-05 | Panthera Biopharma, Llc | Hydroxamic acid derivatives of 3-phenyl propionic acids useful as therapeutic agents for treating anthrax poisoning |
WO2009008905A1 (en) * | 2007-02-01 | 2009-01-15 | Panthera Biopharma, Llc. | Hydroxamic acid derivatives of phenoxy-acetic acids and analogs useful as therapeutic agents for treating anthrax poisoning |
US8119692B2 (en) | 2007-04-02 | 2012-02-21 | Panthera Biopharma Llc | Hydroxamic acid derivatives of 4-phenyl 4-hydroxy, 4-phenyl 4-alkoxy and 4-phenyl 4-arylalkoxy butyric acid useful as therapeutic agents for treating anthrax poisoning |
TW201716375A (zh) | 2007-06-12 | 2017-05-16 | Achaogen Inc | 抗菌劑 |
EP2234608A2 (en) | 2007-12-11 | 2010-10-06 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
CN101503475B (zh) * | 2009-03-12 | 2013-06-19 | 中国人民解放军军事医学科学院生物工程研究所 | 炭疽致死因子结构域(LFn)与炭疽水肿因子结构域(EFn)的融合蛋白及其应用 |
EP2847168A1 (en) | 2012-05-10 | 2015-03-18 | Achaogen, Inc. | Antibacterial agents |
CN111377849A (zh) * | 2018-12-28 | 2020-07-07 | 中国人民解放军军事科学院军事医学研究院 | 化合物、其可药用盐及其医药用途 |
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