CA2737472A1 - Azaindazole compounds as ccr1 receptor antagonists - Google Patents
Azaindazole compounds as ccr1 receptor antagonists Download PDFInfo
- Publication number
- CA2737472A1 CA2737472A1 CA2737472A CA2737472A CA2737472A1 CA 2737472 A1 CA2737472 A1 CA 2737472A1 CA 2737472 A CA2737472 A CA 2737472A CA 2737472 A CA2737472 A CA 2737472A CA 2737472 A1 CA2737472 A1 CA 2737472A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridine
- pyrazolo
- fluorophenyl
- carboxylic acid
- amide
- 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.)
- Abandoned
Links
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title description 3
- 239000002464 receptor antagonist Substances 0.000 title description 2
- 229940044551 receptor antagonist Drugs 0.000 title description 2
- 102000004500 CCR1 Receptors Human genes 0.000 title 1
- 108010017319 CCR1 Receptors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 209
- 238000000034 method Methods 0.000 claims abstract description 102
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 34
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 303
- -1 -(CH2)n-CO2C1-6alkyl Chemical group 0.000 claims description 261
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 121
- 238000006243 chemical reaction Methods 0.000 claims description 89
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 68
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 68
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 48
- SECXISVLQFMRJM-UHFFFAOYSA-N NMP Substances CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 43
- 150000002431 hydrogen Chemical group 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 29
- 239000002585 base Substances 0.000 claims description 28
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000003386 piperidinyl group Chemical group 0.000 claims description 16
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 16
- 125000002757 morpholinyl group Chemical group 0.000 claims description 15
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 13
- 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 claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000012279 sodium borohydride Substances 0.000 claims description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 9
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims description 8
- 229910006069 SO3H Inorganic materials 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 8
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003880 polar aprotic solvent Substances 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims description 6
- 208000037976 chronic inflammation Diseases 0.000 claims description 6
- 230000006020 chronic inflammation Effects 0.000 claims description 6
- 239000002798 polar solvent Substances 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 229940102001 zinc bromide Drugs 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 239000007818 Grignard reagent Substances 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000532 dioxanyl group Chemical group 0.000 claims description 3
- 150000004795 grignard reagents Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 239000004210 ether based solvent Substances 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010064539 Autoimmune myocarditis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 102100031172 C-C chemokine receptor type 1 Human genes 0.000 abstract description 15
- 101710149814 C-C chemokine receptor type 1 Proteins 0.000 abstract description 15
- 208000037765 diseases and disorders Diseases 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 4
- 230000001404 mediated effect Effects 0.000 abstract description 3
- 230000002459 sustained effect Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 477
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 317
- 239000000243 solution Substances 0.000 description 249
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 248
- 239000000203 mixture Substances 0.000 description 218
- 235000019439 ethyl acetate Nutrition 0.000 description 197
- 229920006395 saturated elastomer Polymers 0.000 description 112
- 239000012044 organic layer Substances 0.000 description 105
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 103
- 229910001868 water Inorganic materials 0.000 description 103
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 102
- 239000007787 solid Substances 0.000 description 101
- 239000012267 brine Substances 0.000 description 100
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 100
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 94
- 238000010898 silica gel chromatography Methods 0.000 description 89
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 86
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 85
- 229910052938 sodium sulfate Inorganic materials 0.000 description 85
- 235000011152 sodium sulphate Nutrition 0.000 description 85
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 82
- 230000015572 biosynthetic process Effects 0.000 description 78
- 238000003786 synthesis reaction Methods 0.000 description 77
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 74
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 49
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- 235000019341 magnesium sulphate Nutrition 0.000 description 43
- 235000019270 ammonium chloride Nutrition 0.000 description 40
- 239000002904 solvent Substances 0.000 description 38
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- 239000010410 layer Substances 0.000 description 35
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 32
- GBFJKFNEZIXXHW-UHFFFAOYSA-N 1h-pyrazolo[3,4-c]pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CN=CC2=C1C=NN2 GBFJKFNEZIXXHW-UHFFFAOYSA-N 0.000 description 31
- 239000013058 crude material Substances 0.000 description 28
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- 238000000746 purification Methods 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 24
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- 239000000463 material Substances 0.000 description 20
- JTXOGWNTNOJMLN-UHFFFAOYSA-N 1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carboxylic acid Chemical compound N1=CC=2C(C(=O)O)=CN=CC=2N1C1=CC=C(F)C=C1 JTXOGWNTNOJMLN-UHFFFAOYSA-N 0.000 description 19
- 239000005909 Kieselgur Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 238000004007 reversed phase HPLC Methods 0.000 description 15
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
- 239000002002 slurry Substances 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 238000004809 thin layer chromatography Methods 0.000 description 13
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 239000007821 HATU Substances 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- YKNZTUQUXUXTLE-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(C(F)(F)F)=C1 YKNZTUQUXUXTLE-UHFFFAOYSA-N 0.000 description 12
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- IPGITANZCGHWNZ-UHFFFAOYSA-N [1-(4-fluorophenyl)pyrazolo[4,3-c]pyridin-4-yl]methanol Chemical compound N1=CC=2C(CO)=NC=CC=2N1C1=CC=C(F)C=C1 IPGITANZCGHWNZ-UHFFFAOYSA-N 0.000 description 2
- RLMKQMYJJGVJPR-UHFFFAOYSA-N [1-(4-methylphenyl)sulfonylpyrazol-4-yl]methanol Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1N=CC(CO)=C1 RLMKQMYJJGVJPR-UHFFFAOYSA-N 0.000 description 2
- WUNLPKAAJRLTFI-SFHVURJKSA-N [4-[(1s)-1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]propyl]-6-methylsulfonylpyridin-2-yl] trifluoromethanesulfonate Chemical compound N([C@@H](CC)C=1C=C(N=C(OS(=O)(=O)C(F)(F)F)C=1)S(C)(=O)=O)C(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 WUNLPKAAJRLTFI-SFHVURJKSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- JUDUWRVRNLTGEL-ADKAHSJRSA-N benzyl 2-carbamoyl-4-[(1s)-1-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]piperidine-1-carboxylate Chemical compound NC(=O)C1CC([C@@H](NC(=O)OC(C)(C)C)CC)CCN1C(=O)OCC1=CC=CC=C1 JUDUWRVRNLTGEL-ADKAHSJRSA-N 0.000 description 2
- PWXHVJCQQGTSAM-FQKSQLJCSA-N benzyl 2-carbamoyl-4-[(1s)-1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]propyl]piperidine-1-carboxylate Chemical compound N([C@@H](CC)C1CC(N(CC1)C(=O)OCC=1C=CC=CC=1)C(N)=O)C(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 PWXHVJCQQGTSAM-FQKSQLJCSA-N 0.000 description 2
- LEAUNMLXEXRAJI-SLTAFYQDSA-N benzyl 4-[(1s)-1-aminopropyl]-2-carbamoylpiperidine-1-carboxylate Chemical compound NC(=O)C1CC([C@@H](N)CC)CCN1C(=O)OCC1=CC=CC=C1 LEAUNMLXEXRAJI-SLTAFYQDSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- KHYOCKRDQZYFCO-UHFFFAOYSA-N ethyl 1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carboxylate Chemical compound N1=CC=2C(C(=O)OCC)=CN=CC=2N1C1=CC=C(F)C=C1 KHYOCKRDQZYFCO-UHFFFAOYSA-N 0.000 description 2
- VJQQLEHOZVDAML-UHFFFAOYSA-N ethyl 1-(4-methylphenyl)sulfonylpyrazole-4-carboxylate Chemical compound C1=C(C(=O)OCC)C=NN1S(=O)(=O)C1=CC=C(C)C=C1 VJQQLEHOZVDAML-UHFFFAOYSA-N 0.000 description 2
- AQBJFVCKUVWMLP-UHFFFAOYSA-N ethyl 2-ethylsulfanyl-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(SCC)O1 AQBJFVCKUVWMLP-UHFFFAOYSA-N 0.000 description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BUTPBERGMJVRBM-UHFFFAOYSA-N methanol;methylsulfinylmethane Chemical compound OC.CS(C)=O BUTPBERGMJVRBM-UHFFFAOYSA-N 0.000 description 2
- LCNJTEDEMZMQQD-DHUJRADRSA-N methyl (2r)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanylpropanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LCNJTEDEMZMQQD-DHUJRADRSA-N 0.000 description 2
- FGVXDAZBCFEAIU-HTIIIDOHSA-N methyl (2r)-2-[2-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]butanoylamino]-3-tritylsulfanylpropanoate Chemical compound N([C@@H](CSC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)OC)C(=O)C(CC)NC(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 FGVXDAZBCFEAIU-HTIIIDOHSA-N 0.000 description 2
- DXUZZMIANHJYIU-NRFANRHFSA-N methyl (2r)-2-amino-3-tritylsulfanylpropanoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@H](N)C(=O)OC)C1=CC=CC=C1 DXUZZMIANHJYIU-NRFANRHFSA-N 0.000 description 2
- DPHHQJVBVRRCBD-XZHSVTBWSA-N methyl (2s,3r)-2-[2-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]butanoylamino]-3-trityloxybutanoate Chemical compound N([C@@H]([C@@H](C)OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)OC)C(=O)C(CC)NC(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 DPHHQJVBVRRCBD-XZHSVTBWSA-N 0.000 description 2
- IXWMTFMQEQFTBZ-BKBNBNODSA-N methyl (4s,5s)-2-[1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]propyl]-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate Chemical compound O([C@@H](C)[C@H](N=1)C(=O)OC)C=1C(CC)NC(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 IXWMTFMQEQFTBZ-BKBNBNODSA-N 0.000 description 2
- DAPAXVAUEVRBGS-UHFFFAOYSA-N methyl 2-chloro-6-methoxypyridine-4-carboxylate Chemical compound COC(=O)C1=CC(Cl)=NC(OC)=C1 DAPAXVAUEVRBGS-UHFFFAOYSA-N 0.000 description 2
- CBIVNBJOYPWHPA-UHFFFAOYSA-N methyl 2-methoxy-6-methylsulfanylpyridine-4-carboxylate Chemical compound COC(=O)C1=CC(OC)=NC(SC)=C1 CBIVNBJOYPWHPA-UHFFFAOYSA-N 0.000 description 2
- FRCOQTNNXQOFFL-UHFFFAOYSA-N methyl 2-methoxy-6-methylsulfonylpyridine-4-carboxylate Chemical compound COC(=O)C1=CC(OC)=NC(S(C)(=O)=O)=C1 FRCOQTNNXQOFFL-UHFFFAOYSA-N 0.000 description 2
- OCVZFCSNRMHDOC-HNNXBMFYSA-N methyl 3-[4-[(1s)-1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]ethyl]pyridin-2-yl]sulfonylpropanoate Chemical compound C1=NC(S(=O)(=O)CCC(=O)OC)=CC([C@H](C)NC(=O)C=2C=3C=NN(C=3C=NC=2)C=2C=CC(F)=CC=2)=C1 OCVZFCSNRMHDOC-HNNXBMFYSA-N 0.000 description 2
- NZIQDZMMOJUDPG-QFIPXVFZSA-N methyl 3-[5-[(1s)-1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]propyl]pyridin-3-yl]sulfonylpropanoate Chemical compound N([C@@H](CC)C=1C=C(C=NC=1)S(=O)(=O)CCC(=O)OC)C(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 NZIQDZMMOJUDPG-QFIPXVFZSA-N 0.000 description 2
- DPKZVJZKOVXBFP-HNNXBMFYSA-N methyl 3-[6-[(1s)-1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]ethyl]pyridin-2-yl]sulfonylpropanoate Chemical compound COC(=O)CCS(=O)(=O)C1=CC=CC([C@H](C)NC(=O)C=2C=3C=NN(C=3C=NC=2)C=2C=CC(F)=CC=2)=N1 DPKZVJZKOVXBFP-HNNXBMFYSA-N 0.000 description 2
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- 210000001616 monocyte Anatomy 0.000 description 2
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- ILMRBTWLMIOLTI-UHFFFAOYSA-N n-[(6-bromopyridin-3-yl)methyl]-1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C2=CN=CC(C(=O)NCC=3C=NC(Br)=CC=3)=C2C=N1 ILMRBTWLMIOLTI-UHFFFAOYSA-N 0.000 description 2
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- WVRHBTPPATWMBW-JTQLQIEISA-N tert-butyl n-[(1s)-1-(2-carbamoylpyridin-4-yl)propyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CC)C1=CC=NC(C(N)=O)=C1 WVRHBTPPATWMBW-JTQLQIEISA-N 0.000 description 2
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- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 2
- XGORIBMDIYFFER-UHFFFAOYSA-N (1-methylsulfonylpyrrolo[2,3-b]pyridin-4-yl)methylcarbamic acid Chemical compound C1=CN=C2N(S(=O)(=O)C)C=CC2=C1CNC(O)=O XGORIBMDIYFFER-UHFFFAOYSA-N 0.000 description 1
- FGJKTUJHDASOLO-BYPYZUCNSA-N (1S)-1-(2-methylsulfonyl-1,3-oxazol-5-yl)ethanamine Chemical compound C[C@H](N)C1=CN=C(S(C)(=O)=O)O1 FGJKTUJHDASOLO-BYPYZUCNSA-N 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- GJPQPKKESVWENL-UHFFFAOYSA-L magnesium;ethanesulfinate;bromide Chemical compound [Mg+2].[Br-].CCS([O-])=O GJPQPKKESVWENL-UHFFFAOYSA-L 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- BQDJIDXAJSAAKU-SQSWPQCGSA-N methyl (2s,3r)-2-[2-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]butanoylamino]-3-hydroxybutanoate Chemical compound N1=CC=2C(C(=O)NC(CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)OC)=CN=CC=2N1C1=CC=C(F)C=C1 BQDJIDXAJSAAKU-SQSWPQCGSA-N 0.000 description 1
- HPNBULOPMFDFJG-IBGZPJMESA-N methyl (3s)-3-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]-3-(2-methylsulfonylpyridin-4-yl)propanoate Chemical compound N([C@@H](CC(=O)OC)C=1C=C(N=CC=1)S(C)(=O)=O)C(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 HPNBULOPMFDFJG-IBGZPJMESA-N 0.000 description 1
- WNGBQKLCSIRADR-DJNXLDHESA-N methyl (4r)-2-[1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]propyl]-4,5-dihydro-1,3-thiazole-4-carboxylate Chemical compound C([C@H](N=1)C(=O)OC)SC=1C(CC)NC(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 WNGBQKLCSIRADR-DJNXLDHESA-N 0.000 description 1
- VONGYFFEWFJHNP-UHFFFAOYSA-N methyl 1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC=CN1 VONGYFFEWFJHNP-UHFFFAOYSA-N 0.000 description 1
- XSKGHSUHOYEBTK-UHFFFAOYSA-N methyl 2,6-dichloropyridine-4-carboxylate Chemical compound COC(=O)C1=CC(Cl)=NC(Cl)=C1 XSKGHSUHOYEBTK-UHFFFAOYSA-N 0.000 description 1
- RDEKWBHRWHAELQ-UHFFFAOYSA-N methyl 2-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]acetate Chemical compound N1=CC=2C(C(=O)NCC(=O)OC)=CN=CC=2N1C1=CC=C(F)C=C1 RDEKWBHRWHAELQ-UHFFFAOYSA-N 0.000 description 1
- ITPUFNFIBBVAQG-UHFFFAOYSA-N methyl 2-[[4-[[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]methyl]phenyl]sulfonylamino]acetate Chemical compound C1=CC(S(=O)(=O)NCC(=O)OC)=CC=C1CNC(=O)C1=CN=CC2=C1C=NN2C1=CC=C(F)C=C1 ITPUFNFIBBVAQG-UHFFFAOYSA-N 0.000 description 1
- HTGDXQVCBISJRX-UHFFFAOYSA-N methyl 2-bromo-6-methylpyridine-4-carboxylate Chemical compound COC(=O)C1=CC(C)=NC(Br)=C1 HTGDXQVCBISJRX-UHFFFAOYSA-N 0.000 description 1
- GRGSOOAMCJDZLH-UHFFFAOYSA-N methyl 3-[5-[[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]methyl]pyridin-2-yl]sulfonylpropanoate Chemical compound C1=NC(S(=O)(=O)CCC(=O)OC)=CC=C1CNC(=O)C1=CN=CC2=C1C=NN2C1=CC=C(F)C=C1 GRGSOOAMCJDZLH-UHFFFAOYSA-N 0.000 description 1
- SCZZVFPBXDHKIV-FQEVSTJZSA-N methyl 3-[6-[(1s)-1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]propyl]pyridin-2-yl]sulfonylpropanoate Chemical compound N([C@@H](CC)C=1N=C(C=CC=1)S(=O)(=O)CCC(=O)OC)C(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 SCZZVFPBXDHKIV-FQEVSTJZSA-N 0.000 description 1
- FBPIDMAELBIRLE-UHFFFAOYSA-N methyl 5-bromofuran-2-carboxylate Chemical compound COC(=O)C1=CC=C(Br)O1 FBPIDMAELBIRLE-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000002297 mitogenic effect Effects 0.000 description 1
- ITFZASUFZUCDSU-UHFFFAOYSA-N n,n-diethylethanamine;methylsulfinylmethane Chemical compound CS(C)=O.CCN(CC)CC ITFZASUFZUCDSU-UHFFFAOYSA-N 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- KNVUXSKUAMRABV-UHFFFAOYSA-N n-(cyanomethyl)-2-[1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]propyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC#N)=COC=1C(CC)NC(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 KNVUXSKUAMRABV-UHFFFAOYSA-N 0.000 description 1
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- KZVLNAGYSAKYMG-UHFFFAOYSA-N pyridine-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=N1 KZVLNAGYSAKYMG-UHFFFAOYSA-N 0.000 description 1
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- YICFALDKKMHFLT-UHFFFAOYSA-M sodium;3-methoxy-3-oxopropane-1-sulfinate Chemical compound [Na+].COC(=O)CCS([O-])=O YICFALDKKMHFLT-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
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000008409 synovial inflammation Effects 0.000 description 1
- 210000005222 synovial tissue Anatomy 0.000 description 1
- CXNSSDVWOJFHGJ-UHFFFAOYSA-N tert-butyl 4-[1-[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]propyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(CC)NC(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 CXNSSDVWOJFHGJ-UHFFFAOYSA-N 0.000 description 1
- OPPPHASXHULEJN-UHFFFAOYSA-N tert-butyl n-[(1-methylsulfonylpyrrolo[2,3-b]pyridin-4-yl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=NC2=C1C=CN2S(C)(=O)=O OPPPHASXHULEJN-UHFFFAOYSA-N 0.000 description 1
- NCWCLCDTDRJSEH-YVNMAJEFSA-N tert-butyl n-[(1s)-1-(2-carbamoylpiperidin-4-yl)propyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CC)C1CCNC(C(N)=O)C1 NCWCLCDTDRJSEH-YVNMAJEFSA-N 0.000 description 1
- BXLLWUGZBLWBPE-UHFFFAOYSA-N tert-butyl n-[5-[[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]methyl]pyridin-2-yl]carbamate Chemical compound C1=NC(NC(=O)OC(C)(C)C)=CC=C1CNC(=O)C1=CN=CC2=C1C=NN2C1=CC=C(F)C=C1 BXLLWUGZBLWBPE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000010792 warming Methods 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
-
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- 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
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
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- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Endocrinology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (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 |
|---|---|---|---|
| US10040108P | 2008-09-26 | 2008-09-26 | |
| US61/100,401 | 2008-09-26 | ||
| PCT/US2009/057778 WO2010036632A1 (en) | 2008-09-26 | 2009-09-22 | Azaindazole compounds as ccr1 receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
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| CA2737472A1 true CA2737472A1 (en) | 2010-04-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CA2737472A Abandoned CA2737472A1 (en) | 2008-09-26 | 2009-09-22 | Azaindazole compounds as ccr1 receptor antagonists |
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| CA2722923C (en) | 2008-04-29 | 2016-08-02 | Boehringer Ingelheim International Gmbh | Indazole compounds as ccr1 receptor antagonists |
| EP2297112B1 (en) | 2008-05-06 | 2013-04-03 | Boehringer Ingelheim International GmbH | Pyrazole compounds as ccr1 antagonists |
| AP2739A (en) | 2008-09-26 | 2013-09-30 | Boehringer Ingelheim Int | Azaindazole compounds as CCRI receptor antagonists |
| US20100317646A1 (en) * | 2009-03-19 | 2010-12-16 | Medical Research Council Technology | Compounds |
| PL2491028T3 (pl) | 2009-10-21 | 2014-05-30 | Boehringer Ingelheim Int | Związki indazolowe i pirazolopirydynowe jako antagoniści receptora CCR1 |
| EP2493875B1 (en) | 2009-10-27 | 2014-08-06 | Boehringer Ingelheim International GmbH | Heterocyclic compounds as ccr1 receptor antagonists |
| PH12012501153A1 (en) * | 2009-12-08 | 2012-10-22 | Boehringer Ingelheim Int | Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds |
| US8871786B2 (en) | 2010-04-30 | 2014-10-28 | Boehringer Ingelheim International Gmbh | Azaindazole amide compounds as CCR1 receptor antagonists |
| EP2388260A1 (de) * | 2010-05-21 | 2011-11-23 | Archimica GmbH | Herstellungsverfahren für einen Inhibitor eines Blutgerinnungsfaktors |
| CN103384668B (zh) | 2010-09-03 | 2017-05-31 | 福马Tm有限责任公司 | 用于抑制nampt的化合物和组合物 |
| US8546442B2 (en) | 2010-12-23 | 2013-10-01 | Boehringer Ingelheim International Gmbh | Pyrazolopiperidine compounds as CCR1 receptor antagonists |
| JP2014511389A (ja) | 2011-02-28 | 2014-05-15 | エピザイム インコーポレイテッド | 置換６，５−縮合二環式ヘテロアリール化合物 |
| CN102775365A (zh) * | 2011-05-10 | 2012-11-14 | 无锡立诺康医药科技有限公司 | 5-氨基取代基-异噁唑类化合物或其酸式盐的合成工艺 |
| WO2012163848A1 (en) | 2011-05-27 | 2012-12-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of crohn's disease |
| EP2771011A4 (en) * | 2011-10-24 | 2015-04-15 | Glaxosmithkline Ip No 2 Ltd | CHEMICAL COMPOUNDS |
| EP2771484A1 (en) | 2011-10-28 | 2014-09-03 | Galderma Research & Development | New leukocyte infiltrate markers for rosacea and uses thereof |
| US9458172B2 (en) * | 2012-03-02 | 2016-10-04 | Kenneth W Bair | Pyridinyl and pyrimidinyl sulfoxide and sulfone derivatives |
| AR091858A1 (es) | 2012-07-25 | 2015-03-04 | Sova Pharmaceuticals Inc | INHIBIDORES DE CISTATIONIN-g-LIASA (CSE) |
| US9776996B2 (en) * | 2013-03-15 | 2017-10-03 | Epizyme, Inc. | Substituted 6,5-fused bicyclic heteroaryl compounds |
| US9045477B2 (en) * | 2013-03-15 | 2015-06-02 | Epizyme, Inc. | Substituted 6,5-fused bicyclic heteroaryl compounds |
| FR3016879A1 (fr) * | 2014-01-29 | 2015-07-31 | Guillaume Laconde | Procede de preparation de benzotriazole n-acyles |
| TR201809388T4 (tr) | 2014-03-17 | 2018-07-23 | Pfizer | Metabolik ve ilişkili hastalıkların tedavisinde kullanılmaya yönelik diasilgliserol asiltransferaz 2 inhibitörleri. |
| UA120094C2 (uk) | 2014-04-14 | 2019-10-10 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | Сполуки як модулятори ror-гамма |
| JP6810988B2 (ja) | 2015-10-23 | 2021-01-13 | ヴィフォール （インターナショナル） アクチェンゲゼルシャフトＶｉｆｏｒ （Ｉｎｔｅｒｎａｔｉｏｎａｌ） ＡＧ | 新規なフェロポーチン阻害剤 |
| BR112018009566A2 (pt) | 2015-11-13 | 2018-11-06 | Basf Se | compostos, mistura, composição agroquímica, uso de compostos e método para combater fungos nocivos fitopatogênicos |
| US20180354921A1 (en) | 2015-11-13 | 2018-12-13 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| CA3016068C (en) | 2016-03-07 | 2024-02-27 | The Global Alliance For Tb Drug Development, Inc. | Antibacterial compounds and uses thereof |
| JOP20180036A1 (ar) | 2017-04-18 | 2019-01-30 | Vifor Int Ag | أملاح لمثبطات فروبورتين جديدة |
| TWI853814B (zh) | 2018-05-31 | 2024-09-01 | 南韓商Ｃ＆Ｃ新藥研究所 | 雜環衍生物及其用途 |
| CN111393376B (zh) * | 2020-05-11 | 2022-05-13 | 安徽赛迪生物科技有限公司 | 一种2-氯嘧啶-4-甲酸的合成方法 |
| WO2021262878A1 (en) * | 2020-06-24 | 2021-12-30 | Oregon Health & Science University | Novel molecule for modulation of innate immune responses controlled by sting protein |
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2009
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- 2009-09-22 EA EA201100524A patent/EA201100524A1/ru unknown
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- 2009-09-22 UA UAA201105061A patent/UA103634C2/ru unknown
- 2009-09-22 BR BRPI0919844A patent/BRPI0919844A2/pt not_active IP Right Cessation
- 2009-09-22 AU AU2009296839A patent/AU2009296839A1/en not_active Abandoned
- 2009-09-22 NZ NZ591115A patent/NZ591115A/xx not_active IP Right Cessation
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- 2009-09-22 EP EP09792818.8A patent/EP2346868B1/en active Active
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- 2009-09-24 UY UY0001032140A patent/UY32140A/es not_active Application Discontinuation
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| IL210857A0 (en) | 2011-04-28 |
| ECSP11010932A (es) | 2011-04-29 |
| UY32140A (es) | 2010-04-30 |
| MA32655B1 (fr) | 2011-09-01 |
| US8063065B2 (en) | 2011-11-22 |
| MX2011002951A (es) | 2011-04-26 |
| NZ591115A (en) | 2012-10-26 |
| AP2011005685A0 (en) | 2011-04-30 |
| US20110086846A1 (en) | 2011-04-14 |
| AU2009296839A1 (en) | 2010-04-01 |
| AP2739A (en) | 2013-09-30 |
| US8163918B2 (en) | 2012-04-24 |
| EP2346868B1 (en) | 2016-01-27 |
| US7879873B2 (en) | 2011-02-01 |
| JP5507567B2 (ja) | 2014-05-28 |
| UA103634C2 (en) | 2013-11-11 |
| CO6351735A2 (es) | 2011-12-20 |
| EP2346868A1 (en) | 2011-07-27 |
| ZA201100625B (en) | 2011-09-28 |
| US20120035370A1 (en) | 2012-02-09 |
| TW201018683A (en) | 2010-05-16 |
| CL2011000668A1 (es) | 2011-10-28 |
| PE20110854A1 (es) | 2011-12-23 |
| CN102227425A (zh) | 2011-10-26 |
| AR073689A1 (es) | 2010-11-24 |
| US20120136158A1 (en) | 2012-05-31 |
| JP2012503664A (ja) | 2012-02-09 |
| BRPI0919844A2 (pt) | 2019-09-24 |
| WO2010036632A1 (en) | 2010-04-01 |
| KR20110060904A (ko) | 2011-06-08 |
| US20100093724A1 (en) | 2010-04-15 |
| EA201100524A1 (ru) | 2011-10-31 |
| US8338610B2 (en) | 2012-12-25 |
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