ES2644025T3 - Compuestos de azaindol, síntesis de los mismos, y procedimientos de uso de los mismos - Google Patents
Compuestos de azaindol, síntesis de los mismos, y procedimientos de uso de los mismos Download PDFInfo
- Publication number
- ES2644025T3 ES2644025T3 ES14745305.4T ES14745305T ES2644025T3 ES 2644025 T3 ES2644025 T3 ES 2644025T3 ES 14745305 T ES14745305 T ES 14745305T ES 2644025 T3 ES2644025 T3 ES 2644025T3
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- ES
- Spain
- Prior art keywords
- methyl
- hydrogen
- mmol
- compound
- pyrrolo
- 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.)
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- 230000015572 biosynthetic process Effects 0.000 title description 40
- 238000003786 synthesis reaction Methods 0.000 title description 33
- 238000000034 method Methods 0.000 title description 25
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title 1
- 239000001257 hydrogen Substances 0.000 claims abstract description 223
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 223
- 150000001875 compounds Chemical class 0.000 claims abstract description 174
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 118
- -1 -OH Chemical group 0.000 claims abstract description 91
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 67
- 239000011737 fluorine Chemical group 0.000 claims abstract description 47
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims abstract description 5
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims abstract description 5
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 201000008827 tuberculosis Diseases 0.000 claims description 50
- 239000003814 drug Substances 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 31
- 208000031998 Mycobacterium Infections Diseases 0.000 claims description 24
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 description 200
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 188
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 89
- 239000000543 intermediate Substances 0.000 description 77
- 239000000243 solution Substances 0.000 description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 61
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 60
- 239000011541 reaction mixture Substances 0.000 description 60
- 239000000203 mixture Substances 0.000 description 54
- 239000012267 brine Substances 0.000 description 53
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 53
- 230000002829 reductive effect Effects 0.000 description 47
- 239000012074 organic phase Substances 0.000 description 46
- 235000019439 ethyl acetate Nutrition 0.000 description 44
- 241000699670 Mus sp. Species 0.000 description 39
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 39
- 229910052938 sodium sulfate Inorganic materials 0.000 description 38
- 235000011152 sodium sulphate Nutrition 0.000 description 38
- 239000007787 solid Substances 0.000 description 38
- 238000005160 1H NMR spectroscopy Methods 0.000 description 35
- 150000003857 carboxamides Chemical class 0.000 description 34
- 239000002904 solvent Substances 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- 229940079593 drug Drugs 0.000 description 30
- 239000002253 acid Substances 0.000 description 28
- 210000004027 cell Anatomy 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 239000012071 phase Substances 0.000 description 25
- 239000000725 suspension Substances 0.000 description 25
- 208000015181 infectious disease Diseases 0.000 description 23
- 238000000746 purification Methods 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 20
- 241000700159 Rattus Species 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 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 14
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 13
- ZDWPBMJZDNXTPG-UHFFFAOYSA-N 2h-benzotriazol-4-amine Chemical compound NC1=CC=CC2=C1NN=N2 ZDWPBMJZDNXTPG-UHFFFAOYSA-N 0.000 description 13
- 241000699666 Mus <mouse, genus> Species 0.000 description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 12
- 230000001580 bacterial effect Effects 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 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 12
- 210000004072 lung Anatomy 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 241000894006 Bacteria Species 0.000 description 10
- 230000001684 chronic effect Effects 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 229940126214 compound 3 Drugs 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 230000008030 elimination Effects 0.000 description 10
- 238000003379 elimination reaction Methods 0.000 description 10
- LIMXEVCFAUTBCK-UHFFFAOYSA-N 2,5-dibromo-3-methylpyridine Chemical compound CC1=CC(Br)=CN=C1Br LIMXEVCFAUTBCK-UHFFFAOYSA-N 0.000 description 9
- LDQOJCWKNPRQRD-UHFFFAOYSA-N 6-(chloromethyl)-n,n,5-trimethylpyrimidin-4-amine Chemical compound CN(C)C1=NC=NC(CCl)=C1C LDQOJCWKNPRQRD-UHFFFAOYSA-N 0.000 description 9
- PJVBBXRJBOJURT-UHFFFAOYSA-N CCOC(=O)c1ncnc(N(C)C)c1C Chemical compound CCOC(=O)c1ncnc(N(C)C)c1C PJVBBXRJBOJURT-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001727 in vivo Methods 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 8
- 229920000053 polysorbate 80 Polymers 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 7
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- FURHRJBOFNDYTG-UHFFFAOYSA-N 2-fluoroethanamine Chemical compound NCCF FURHRJBOFNDYTG-UHFFFAOYSA-N 0.000 description 7
- YRRZGBOZBIVMJT-UHFFFAOYSA-N 2-fluoroethanamine;hydron;chloride Chemical compound Cl.NCCF YRRZGBOZBIVMJT-UHFFFAOYSA-N 0.000 description 7
- 239000000443 aerosol Substances 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 210000003494 hepatocyte Anatomy 0.000 description 7
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 7
- WADLLLSMEPLCNO-UHFFFAOYSA-N methyl 2,6-dichloro-5-fluoropyridine-3-carboxylate Chemical compound COC(=O)C1=CC(F)=C(Cl)N=C1Cl WADLLLSMEPLCNO-UHFFFAOYSA-N 0.000 description 7
- AARWZYFWYNJHOQ-UHFFFAOYSA-N methyl 2-chloro-5-fluoro-6-methylpyridine-3-carboxylate Chemical compound COC(=O)C1=CC(F)=C(C)N=C1Cl AARWZYFWYNJHOQ-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 239000003643 water by type Substances 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- FTRQCCAMRDXXGH-UHFFFAOYSA-N 3-nitro-1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CN=C2C([N+](=O)[O-])=CNC2=C1 FTRQCCAMRDXXGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- MSGLTNPWXHMGSD-UHFFFAOYSA-N COC(=O)c1cc(F)c(C)nc1OC Chemical compound COC(=O)c1cc(F)c(C)nc1OC MSGLTNPWXHMGSD-UHFFFAOYSA-N 0.000 description 6
- WFZXXYZKMULQOU-UHFFFAOYSA-N COc1nc(C)c(F)cc1CO Chemical compound COc1nc(C)c(F)cc1CO WFZXXYZKMULQOU-UHFFFAOYSA-N 0.000 description 6
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- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 6
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- XKLOLWKHCLHTCC-UHFFFAOYSA-N methyl 2-methoxy-5-(trifluoromethyl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC(C(F)(F)F)=CN=C1OC XKLOLWKHCLHTCC-UHFFFAOYSA-N 0.000 description 6
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- 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
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)
- Oncology (AREA)
- Communicable Diseases (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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3196CH2013 | 2013-07-17 | ||
| IN3196CH2013 | 2013-07-17 | ||
| INCH31962013 | 2014-04-30 | ||
| PCT/US2014/046100 WO2015009525A1 (en) | 2013-07-17 | 2014-07-10 | Azaindole compounds, synthesis thereof, and methods of using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2644025T3 true ES2644025T3 (es) | 2017-11-27 |
Family
ID=51261257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14745305.4T Active ES2644025T3 (es) | 2013-07-17 | 2014-07-10 | Compuestos de azaindol, síntesis de los mismos, y procedimientos de uso de los mismos |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9163020B2 (https=) |
| EP (1) | EP3021947B1 (https=) |
| JP (1) | JP6366709B2 (https=) |
| KR (1) | KR102301753B1 (https=) |
| CN (1) | CN105636646B (https=) |
| AU (1) | AU2014290598B2 (https=) |
| CA (1) | CA2918487C (https=) |
| EA (1) | EA028611B1 (https=) |
| ES (1) | ES2644025T3 (https=) |
| WO (1) | WO2015009525A1 (https=) |
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 |
| ES2997871T3 (en) | 2017-12-06 | 2025-02-18 | Prollergy Corp | 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 |
Family Cites Families (3)
| 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 |
| CA2691512A1 (en) * | 2007-08-10 | 2009-02-19 | H. Lundbeck A/S | Heteroaryl amide analogues |
| CA2793086C (en) * | 2010-03-18 | 2018-08-21 | Institut Pasteur Korea | Substituted imidazo[1,2-a]pyridine compounds and their use in the treatment of bacterial infections |
-
2014
- 2014-07-10 CA CA2918487A patent/CA2918487C/en active Active
- 2014-07-10 ES ES14745305.4T patent/ES2644025T3/es active Active
- 2014-07-10 EP EP14745305.4A patent/EP3021947B1/en active Active
- 2014-07-10 CN CN201480046182.4A patent/CN105636646B/zh active Active
- 2014-07-10 US US14/327,784 patent/US9163020B2/en active Active
- 2014-07-10 JP JP2016526988A patent/JP6366709B2/ja active Active
- 2014-07-10 KR KR1020167004150A patent/KR102301753B1/ko 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 EA EA201690227A patent/EA028611B1/ru unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US9163020B2 (en) | 2015-10-20 |
| EP3021947A1 (en) | 2016-05-25 |
| US20150025087A1 (en) | 2015-01-22 |
| KR20160058757A (ko) | 2016-05-25 |
| AU2014290598A1 (en) | 2016-02-11 |
| JP2016530242A (ja) | 2016-09-29 |
| EP3021947B1 (en) | 2017-08-23 |
| WO2015009525A1 (en) | 2015-01-22 |
| KR102301753B1 (ko) | 2021-09-15 |
| CA2918487C (en) | 2021-08-03 |
| CN105636646A (zh) | 2016-06-01 |
| EA028611B1 (ru) | 2017-12-29 |
| CA2918487A1 (en) | 2015-01-22 |
| CN105636646B (zh) | 2017-12-19 |
| JP6366709B2 (ja) | 2018-08-01 |
| EA201690227A1 (ru) | 2016-07-29 |
| BR112016000712A2 (pt) | 2022-03-22 |
| AU2014290598B2 (en) | 2018-11-08 |
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