BRPI0810244A2 - Molécula, e, métodos para tratar um paciente infectado com mycobacterium tuberculosis e com francisella tulerensis - Google Patents
Molécula, e, métodos para tratar um paciente infectado com mycobacterium tuberculosis e com francisella tulerensis Download PDFInfo
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- BRPI0810244A2 BRPI0810244A2 BRPI0810244-9A BRPI0810244A BRPI0810244A2 BR PI0810244 A2 BRPI0810244 A2 BR PI0810244A2 BR PI0810244 A BRPI0810244 A BR PI0810244A BR PI0810244 A2 BRPI0810244 A2 BR PI0810244A2
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- Prior art keywords
- aryl
- alkyl
- cycloalkyl
- formula
- heterocyclic
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 25
- 241000589601 Francisella Species 0.000 title claims description 8
- 241000187479 Mycobacterium tuberculosis Species 0.000 title claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 112
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 80
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 44
- 101100516563 Caenorhabditis elegans nhr-6 gene Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 125000002837 carbocyclic group Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 82
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 59
- 238000005160 1H NMR spectroscopy Methods 0.000 description 55
- -1 1-methyl-pentyl Chemical group 0.000 description 34
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- 230000015572 biosynthetic process Effects 0.000 description 18
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- 238000003786 synthesis reaction Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 15
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- 201000008827 tuberculosis Diseases 0.000 description 14
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 125000001475 halogen functional group Chemical group 0.000 description 9
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- 241000894006 Bacteria Species 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
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- 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
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- 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
- A61P31/06—Antibacterial agents for tuberculosis
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- 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
- A61P31/08—Antibacterial agents for leprosy
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91298007P | 2007-04-20 | 2007-04-20 | |
| US60/912980 | 2007-04-20 | ||
| PCT/US2008/005084 WO2008130669A1 (en) | 2007-04-20 | 2008-04-21 | Benzimidazoles and pharmaceutical compositions thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0810244A2 true BRPI0810244A2 (pt) | 2014-09-30 |
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| BRPI0810244-9A BRPI0810244A2 (pt) | 2007-04-20 | 2008-04-21 | Molécula, e, métodos para tratar um paciente infectado com mycobacterium tuberculosis e com francisella tulerensis |
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| PT (1) | PT2154966E (https=) |
| SI (1) | SI2154966T1 (https=) |
| WO (1) | WO2008130669A1 (https=) |
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| US8232310B2 (en) | 2006-12-29 | 2012-07-31 | Georgetown University | Targeting of EWS-FLI1 as anti-tumor therapy |
| US8039502B2 (en) | 2007-07-24 | 2011-10-18 | The Ohio State University Research Foundation | Anti-infective agents against intracellular pathogens |
| US20120108823A1 (en) | 2009-04-22 | 2012-05-03 | The Ohio State University Research Foundation | Anti-francisella agents |
| JP5934645B2 (ja) | 2009-09-11 | 2016-06-15 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのヘテロ環式誘導体 |
| WO2013116823A1 (en) * | 2012-02-02 | 2013-08-08 | The Research Foundation Of State University Of New York | Benzimidazoles and uses thereof |
| WO2013142326A1 (en) * | 2012-03-23 | 2013-09-26 | The Research Foundation Of State University Of New York | 5-carbonylamino-/(sulfonamido-) substituted benz imidazoles and use thereof treatment of tuberculosis |
| CN107011242B (zh) * | 2012-04-12 | 2020-08-07 | 乔治城大学 | 用于治疗尤文肉瘤家族肿瘤的方法和组合物 |
| CN103333170B (zh) * | 2013-06-14 | 2016-08-10 | 清华大学 | 苯并咪唑类化合物及其用途 |
| AU2014340398A1 (en) | 2013-10-24 | 2016-06-09 | Georgetown University | Methods and compositions for treating cancer |
| WO2015077276A1 (en) | 2013-11-22 | 2015-05-28 | The Research Foundation For The State University Of New York | Benzimidazoles and their use in the treatment of tuberculosis |
| US10287617B2 (en) | 2014-03-11 | 2019-05-14 | Colorado State University Research Foundation | Methods for in vitro—in vivo efficacy determination |
| WO2015193506A1 (en) * | 2014-06-20 | 2015-12-23 | Institut Pasteur Korea | Anti-infective compounds |
| CN107108580B (zh) | 2014-10-09 | 2020-06-30 | 英克特诺治疗公司 | 吲哚酮化合物及其用途 |
| EP3795563B1 (en) | 2016-03-31 | 2024-07-17 | Oncternal Therapeutics, Inc. | Indoline analogs and uses thereof |
| CA3029851A1 (en) | 2016-07-29 | 2018-02-01 | Oncternal Therapeutics, Inc. | Uses of indoline compounds such as tk216 for the treatment of cancer |
| CN111303092B (zh) * | 2020-04-07 | 2021-05-25 | 山东昌邑灶户盐化有限公司 | 2,4-二硝基-6-氯苯胺衍生物、合成方法及其应用 |
| KR20240035820A (ko) | 2021-07-09 | 2024-03-18 | 플렉시움 인코포레이티드 | Ikzf2를 조절하는 아릴 화합물 및 약학 조성물 |
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| EP1805147B1 (en) * | 2004-09-30 | 2014-08-13 | Janssen Pharmaceutica NV | Novel benzimidazole derivatives useful as selective androgen receptor modulators (sarms) |
| EP2008210A1 (en) | 2006-03-15 | 2008-12-31 | Csir | Modulation of phosphoryl transferase activity of glutamine synthetase |
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Also Published As
| Publication number | Publication date |
|---|---|
| US20100256203A1 (en) | 2010-10-07 |
| PL2154966T3 (pl) | 2014-03-31 |
| JP5400032B2 (ja) | 2014-01-29 |
| CA2684594C (en) | 2015-10-06 |
| CN101677553A (zh) | 2010-03-24 |
| IN2009KN03959A (https=) | 2015-08-28 |
| MX2009011281A (es) | 2010-03-08 |
| EP2154966A1 (en) | 2010-02-24 |
| EP2154966B1 (en) | 2013-08-21 |
| EA016726B1 (ru) | 2012-07-30 |
| AU2008242488A1 (en) | 2008-10-30 |
| ES2434693T3 (es) | 2013-12-17 |
| JP2010524947A (ja) | 2010-07-22 |
| AU2008242488B2 (en) | 2014-10-30 |
| PT2154966E (pt) | 2013-11-13 |
| EP2154966A4 (en) | 2010-12-15 |
| CA2684594A1 (en) | 2008-10-30 |
| US8232410B2 (en) | 2012-07-31 |
| SI2154966T1 (sl) | 2014-02-28 |
| WO2008130669A1 (en) | 2008-10-30 |
| EA200901423A1 (ru) | 2010-06-30 |
| HRP20131103T1 (hr) | 2013-12-20 |
| DK2154966T3 (da) | 2013-11-18 |
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