CA2918487C - Azaindole compounds, synthesis thereof, and methods of using the same - Google Patents
Azaindole compounds, synthesis thereof, and methods of using the same Download PDFInfo
- Publication number
- CA2918487C CA2918487C CA2918487A CA2918487A CA2918487C CA 2918487 C CA2918487 C CA 2918487C CA 2918487 A CA2918487 A CA 2918487A CA 2918487 A CA2918487 A CA 2918487A CA 2918487 C CA2918487 C CA 2918487C
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- Prior art keywords
- methyl
- hydrogen
- compound
- mmol
- pyrrolo
- Prior art date
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- 230000015572 biosynthetic process Effects 0.000 title description 38
- 238000003786 synthesis reaction Methods 0.000 title description 31
- 238000000034 method Methods 0.000 title description 21
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 166
- 201000008827 tuberculosis Diseases 0.000 claims abstract description 53
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 208000031998 Mycobacterium Infections Diseases 0.000 claims abstract description 31
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 217
- 239000001257 hydrogen Substances 0.000 claims description 216
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 127
- 239000000203 mixture Substances 0.000 claims description 55
- 239000003814 drug Substances 0.000 claims description 50
- 229910052731 fluorine Inorganic materials 0.000 claims description 47
- 239000011737 fluorine Substances 0.000 claims description 47
- 238000011282 treatment Methods 0.000 claims description 40
- 208000015181 infectious disease Diseases 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 241000186359 Mycobacterium Species 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 102100028651 Tenascin-N Human genes 0.000 claims 1
- 101710087911 Tenascin-N Proteins 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 10
- 150000002431 hydrogen Chemical class 0.000 description 198
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 190
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 85
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 52
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- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 12
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- 238000004458 analytical method Methods 0.000 description 11
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- 238000003556 assay Methods 0.000 description 10
- 230000001684 chronic effect Effects 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- CRWGVNPMHWCPJG-UHFFFAOYSA-N ethyl 6-chloro-5-methylpyrimidine-4-carboxylate Chemical compound CCOC(=O)C1=NC=NC(Cl)=C1C CRWGVNPMHWCPJG-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
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- XREYIXULAVYZAT-UHFFFAOYSA-N [6-(dimethylamino)-5-methylpyrimidin-4-yl]methanol Chemical compound CN(C)C1=NC=NC(CO)=C1C XREYIXULAVYZAT-UHFFFAOYSA-N 0.000 description 9
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- LIMXEVCFAUTBCK-UHFFFAOYSA-N 2,5-dibromo-3-methylpyridine Chemical compound CC1=CC(Br)=CN=C1Br LIMXEVCFAUTBCK-UHFFFAOYSA-N 0.000 description 8
- YRRZGBOZBIVMJT-UHFFFAOYSA-N 2-fluoroethanamine;hydron;chloride Chemical compound Cl.NCCF YRRZGBOZBIVMJT-UHFFFAOYSA-N 0.000 description 8
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000065 noncytotoxic Toxicity 0.000 description 1
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- 238000010606 normalization Methods 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- HGASFNYMVGEKTF-UHFFFAOYSA-N octan-1-ol;hydrate Chemical compound O.CCCCCCCCO HGASFNYMVGEKTF-UHFFFAOYSA-N 0.000 description 1
- 229960001699 ofloxacin Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 238000002205 phenol-chloroform extraction Methods 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 239000002824 redox indicator Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229960000885 rifabutin Drugs 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010187 selection method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- MRTAVLDNYYEJHK-UHFFFAOYSA-M sodium;2-chloro-2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)Cl MRTAVLDNYYEJHK-UHFFFAOYSA-M 0.000 description 1
- XZPVPNZTYPUODG-UHFFFAOYSA-M sodium;chloride;dihydrate Chemical compound O.O.[Na+].[Cl-] XZPVPNZTYPUODG-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 238000007921 solubility assay Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- 229960002784 thioridazine Drugs 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- GXFAIFRPOKBQRV-GHXCTMGLSA-N viomycin Chemical compound N1C(=O)\C(=C\NC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)C[C@@H](N)CCCN)CNC(=O)[C@@H]1[C@@H]1NC(=N)N[C@@H](O)C1 GXFAIFRPOKBQRV-GHXCTMGLSA-N 0.000 description 1
- 229950001272 viomycin Drugs 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
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- 229940046008 vitamin d Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- 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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3196CH2013 | 2013-07-17 | ||
| IN3196/CHE/2013 | 2013-07-17 | ||
| PCT/US2014/046100 WO2015009525A1 (en) | 2013-07-17 | 2014-07-10 | Azaindole compounds, synthesis thereof, and methods of using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2918487A1 CA2918487A1 (en) | 2015-01-22 |
| CA2918487C true CA2918487C (en) | 2021-08-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2918487A Active CA2918487C (en) | 2013-07-17 | 2014-07-10 | Azaindole compounds, synthesis thereof, and methods of using the same |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9163020B2 (enExample) |
| EP (1) | EP3021947B1 (enExample) |
| JP (1) | JP6366709B2 (enExample) |
| KR (1) | KR102301753B1 (enExample) |
| CN (1) | CN105636646B (enExample) |
| AU (1) | AU2014290598B2 (enExample) |
| CA (1) | CA2918487C (enExample) |
| EA (1) | EA028611B1 (enExample) |
| ES (1) | ES2644025T3 (enExample) |
| WO (1) | WO2015009525A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201512197A (zh) * | 2013-08-30 | 2015-04-01 | Hoffmann La Roche | 吡咯并吡啶或吡唑并吡啶衍生物 |
| GB201317363D0 (en) * | 2013-10-01 | 2013-11-13 | Eisai Ltd | Novel compounds |
| US11173113B2 (en) | 2017-12-06 | 2021-11-16 | Prollergy Corporation | Composition and method for reducing allergic response |
| RU2702224C2 (ru) * | 2018-03-29 | 2019-10-07 | Общество С Ограниченной Ответственностью "Мт-Медикалс" | Производные фенил формамидина, обладающие антимикобактериальной активностью |
| WO2019239382A1 (en) | 2018-06-15 | 2019-12-19 | Cadila Healthcare Limited | Condensed azaheteroaryl compounds having antibacterial activity against tuberculosis bacteria |
| WO2020188405A1 (en) * | 2019-03-20 | 2020-09-24 | Foundation For Neglected Disease Research | Benzimidazoles derivatives as anti-tuberculosis agents |
| CN111393435A (zh) * | 2020-03-16 | 2020-07-10 | 青岛吉澳医药科技有限公司 | 氮杂吲哚酰胺类化合物及其制备方法和用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1532980A1 (en) * | 2003-11-24 | 2005-05-25 | Novo Nordisk A/S | N-heteroaryl indole carboxamides and analogues thereof, for use as glucokinase activators in the treatment of diabetes |
| UA99729C2 (en) * | 2007-08-10 | 2012-09-25 | Х. Луннбек А/С | Heteroaryl amide analogues |
| RU2576662C2 (ru) * | 2010-03-18 | 2016-03-10 | Энститю Пастер Корея | Противоинфекционные соединения |
-
2014
- 2014-07-10 JP JP2016526988A patent/JP6366709B2/ja active Active
- 2014-07-10 CN CN201480046182.4A patent/CN105636646B/zh active Active
- 2014-07-10 KR KR1020167004150A patent/KR102301753B1/ko active Active
- 2014-07-10 EA EA201690227A patent/EA028611B1/ru unknown
- 2014-07-10 CA CA2918487A patent/CA2918487C/en active Active
- 2014-07-10 ES ES14745305.4T patent/ES2644025T3/es active Active
- 2014-07-10 AU AU2014290598A patent/AU2014290598B2/en active Active
- 2014-07-10 WO PCT/US2014/046100 patent/WO2015009525A1/en not_active Ceased
- 2014-07-10 US US14/327,784 patent/US9163020B2/en active Active
- 2014-07-10 EP EP14745305.4A patent/EP3021947B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN105636646B (zh) | 2017-12-19 |
| WO2015009525A1 (en) | 2015-01-22 |
| CA2918487A1 (en) | 2015-01-22 |
| EP3021947B1 (en) | 2017-08-23 |
| KR102301753B1 (ko) | 2021-09-15 |
| CN105636646A (zh) | 2016-06-01 |
| BR112016000712A2 (pt) | 2022-03-22 |
| US20150025087A1 (en) | 2015-01-22 |
| AU2014290598A1 (en) | 2016-02-11 |
| EA201690227A1 (ru) | 2016-07-29 |
| ES2644025T3 (es) | 2017-11-27 |
| JP2016530242A (ja) | 2016-09-29 |
| JP6366709B2 (ja) | 2018-08-01 |
| EA028611B1 (ru) | 2017-12-29 |
| KR20160058757A (ko) | 2016-05-25 |
| EP3021947A1 (en) | 2016-05-25 |
| AU2014290598B2 (en) | 2018-11-08 |
| US9163020B2 (en) | 2015-10-20 |
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| EEER | Examination request |
Effective date: 20190708 |