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)
- 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 (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 (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 |
| KR20210021042A (ko) * | 2018-06-15 | 2021-02-24 | 카딜라 핼쓰캐어 리미티드 | 포유동물 감염 치료를 위한 신규한 화합물 |
| 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 |
| BRPI0812594A2 (pt) * | 2007-08-10 | 2015-06-23 | Lundbeck & Co As H | Composto ou sal ou hidrato do mesmo, composição farmacêutica, métodos para modulação da atividade de um receptor p2x7, para tratamento de uma condição responsiva á modulação do receptor p2x7 em um paciente, para inibição de morte de células gangliônicas retinais em um paciente, para determinação da presença ou ausência de receptor p2x7 em uma amostra, preparação farmacêutica acondicionada, e, uso de um composto ou sal ou hidrato do mesmo. |
| MX345762B (es) * | 2010-03-18 | 2017-02-15 | Pasteur Institut Korea | Compuestos antiinfecciosos. |
-
2014
- 2014-07-10 KR KR1020167004150A patent/KR102301753B1/ko active Active
- 2014-07-10 AU AU2014290598A patent/AU2014290598B2/en active Active
- 2014-07-10 EA EA201690227A patent/EA028611B1/ru unknown
- 2014-07-10 WO PCT/US2014/046100 patent/WO2015009525A1/en not_active Ceased
- 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 EP EP14745305.4A patent/EP3021947B1/en active Active
- 2014-07-10 ES ES14745305.4T patent/ES2644025T3/es active Active
- 2014-07-10 JP JP2016526988A patent/JP6366709B2/ja active Active
- 2014-07-10 CA CA2918487A patent/CA2918487C/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| AU2014290598B2 (en) | 2018-11-08 |
| EP3021947A1 (en) | 2016-05-25 |
| CA2918487A1 (en) | 2015-01-22 |
| AU2014290598A1 (en) | 2016-02-11 |
| CN105636646A (zh) | 2016-06-01 |
| BR112016000712A2 (pt) | 2022-03-22 |
| CA2918487C (en) | 2021-08-03 |
| JP2016530242A (ja) | 2016-09-29 |
| WO2015009525A1 (en) | 2015-01-22 |
| US9163020B2 (en) | 2015-10-20 |
| EA201690227A1 (ru) | 2016-07-29 |
| JP6366709B2 (ja) | 2018-08-01 |
| CN105636646B (zh) | 2017-12-19 |
| KR20160058757A (ko) | 2016-05-25 |
| KR102301753B1 (ko) | 2021-09-15 |
| EP3021947B1 (en) | 2017-08-23 |
| EA028611B1 (ru) | 2017-12-29 |
| US20150025087A1 (en) | 2015-01-22 |
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