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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NZ536189A (en) | 2002-05-29 | 2007-08-31 | Merck & Co Inc | Methylphenylsulfonyl amide derivative compounds useful in the treatment of anthrax and inhibiting lethal factor |
US7601351B1 (en) | 2002-06-26 | 2009-10-13 | Human Genome Sciences, Inc. | Antibodies against protective antigen |
EP1747212A4 (en) * | 2004-05-11 | 2009-03-25 | Merck & Co Inc | PROCESS FOR PRODUCING N-SULFINATED 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 |
EP2001838B1 (en) * | 2006-03-29 | 2014-03-12 | Novartis AG | Selective hydroxamate based mmp inhibitors |
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 |
WO2008147480A2 (en) * | 2007-02-01 | 2008-12-04 | Panthera Biopharna, Llc. | Hydroxamic acid derivatives of 3-phenyl propionic acids useful as thrapeutic agents for treating anthrax poisoning |
US8242174B2 (en) | 2007-02-01 | 2012-08-14 | Panthera Biopharma Llc | Hydroxamic acid derivatives of aniline useful as therapeutic agents for treating anthrax poisoning |
WO2009008920A2 (en) * | 2007-04-02 | 2009-01-15 | 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 |
EP2662353A3 (en) | 2007-06-12 | 2014-04-02 | Achaogen, Inc. | Antibacterial agents |
JP2011517313A (ja) | 2007-12-11 | 2011-06-02 | ビアメト ファーマシューティカルズ,インク. | 金属結合部分を標的化部分と組み合わせて使用する金属酵素阻害剤 |
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 |
WO2013170165A1 (en) | 2012-05-10 | 2013-11-14 | 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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