ES2372540T3 - Activadores de glucocinasa. - Google Patents

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Publication number

ES2372540T3

ES2372540T3 ES06826456T ES06826456T ES2372540T3 ES 2372540 T3 ES2372540 T3 ES 2372540T3 ES 06826456 T ES06826456 T ES 06826456T ES 06826456 T ES06826456 T ES 06826456T ES 2372540 T3 ES2372540 T3 ES 2372540T3

Authority

ES

Spain

Prior art keywords

mmol

pyridin

benzyloxy

compound

formula

Prior art date

2005-11-01

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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• 239000012190 activator Substances 0.000 title description 10
• 150000001875 compounds Chemical class 0.000 claims abstract description 333
• 238000000034 method Methods 0.000 claims abstract description 152
• 102000030595 Glucokinase Human genes 0.000 claims abstract description 58
• 108010021582 Glucokinase Proteins 0.000 claims abstract description 58
• 238000011282 treatment Methods 0.000 claims abstract description 43
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 37
• 230000003213 activating effect Effects 0.000 claims abstract description 10
• -1 4-piperidyl Chemical group 0.000 claims description 273
• 239000000203 mixture Substances 0.000 claims description 106
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 67
• 150000003839 salts Chemical class 0.000 claims description 50
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 48
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 42
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 41
• 125000000623 heterocyclic group Chemical group 0.000 claims description 36
• 229920006395 saturated elastomer Polymers 0.000 claims description 33
• 229910052801 chlorine Inorganic materials 0.000 claims description 25
• 239000002585 base Substances 0.000 claims description 24
• 229910052794 bromium Inorganic materials 0.000 claims description 23
• 102000004877 Insulin Human genes 0.000 claims description 21
• 108090001061 Insulin Proteins 0.000 claims description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 201000010099 disease Diseases 0.000 claims description 21
• 229940125396 insulin Drugs 0.000 claims description 21
• 125000002947 alkylene group Chemical group 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 20
• 239000003153 chemical reaction reagent Substances 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
• 229910052740 iodine Inorganic materials 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 239000012453 solvate Substances 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 239000003054 catalyst Substances 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 125000004450 alkenylene group Chemical group 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 9
• 229910052751 metal Inorganic materials 0.000 claims description 9
• 239000002184 metal Substances 0.000 claims description 9
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 7
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
• 238000005859 coupling reaction Methods 0.000 claims description 6
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 230000008878 coupling Effects 0.000 claims description 5
• 238000010168 coupling process Methods 0.000 claims description 5
• 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 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 229910003827 NRaRb Inorganic materials 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 229910052705 radium Inorganic materials 0.000 claims description 4
• 229910052701 rubidium Inorganic materials 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 2
• 230000001419 dependent effect Effects 0.000 claims description 2
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 2
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
• 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims description 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 14
• 230000001404 mediated effect Effects 0.000 abstract description 10
• 208000037765 diseases and disorders Diseases 0.000 abstract description 7
• 230000002950 deficient Effects 0.000 abstract description 6
• 230000006806 disease prevention Effects 0.000 abstract description 3
• 206010011953 Decreased activity Diseases 0.000 abstract 1
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 247
• 238000005160 1H NMR spectroscopy Methods 0.000 description 187
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 152
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 143
• 238000001819 mass spectrum Methods 0.000 description 133
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 101
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 91
• 239000011541 reaction mixture Substances 0.000 description 81
• 239000007787 solid Substances 0.000 description 80
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 74
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
• 238000006243 chemical reaction Methods 0.000 description 67
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 66
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 64
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
• 235000019439 ethyl acetate Nutrition 0.000 description 58
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 54
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 53
• 239000008103 glucose Substances 0.000 description 53
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
• 230000015572 biosynthetic process Effects 0.000 description 47
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 239000012074 organic phase Substances 0.000 description 45
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 42
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
• 238000002360 preparation method Methods 0.000 description 39
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 31
• 239000000843 powder Substances 0.000 description 28
• 239000000243 solution Substances 0.000 description 28
• 208000035475 disorder Diseases 0.000 description 27
• 239000003814 drug Substances 0.000 description 27
• 150000003840 hydrochlorides Chemical class 0.000 description 27
• 239000000460 chlorine Substances 0.000 description 25
• 238000009472 formulation Methods 0.000 description 24
• 239000000741 silica gel Substances 0.000 description 24
• 229910002027 silica gel Inorganic materials 0.000 description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
• 239000002904 solvent Substances 0.000 description 23
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 22
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
• 239000012458 free base Substances 0.000 description 22
• 239000012071 phase Substances 0.000 description 21
• 229910052938 sodium sulfate Inorganic materials 0.000 description 21
• 235000011152 sodium sulphate Nutrition 0.000 description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• 239000012267 brine Substances 0.000 description 20
• 229910000027 potassium carbonate Inorganic materials 0.000 description 20
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
• 239000002253 acid Substances 0.000 description 19
• BVQJWGILQNRURY-UHFFFAOYSA-N n-(5-bromo-3-phenylmethoxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(Br)=CN=2)OCC=2C=CC=CC=2)=N1 BVQJWGILQNRURY-UHFFFAOYSA-N 0.000 description 19
• 239000008194 pharmaceutical composition Substances 0.000 description 19
• 150000002390 heteroarenes Chemical class 0.000 description 17
• 239000004480 active ingredient Substances 0.000 description 16
• 229940079593 drug Drugs 0.000 description 16
• 230000000670 limiting effect Effects 0.000 description 16
• 239000000463 material Substances 0.000 description 16
• 235000011181 potassium carbonates Nutrition 0.000 description 16
• 241000349731 Afzelia bipindensis Species 0.000 description 15
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 15
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 15
• 150000001412 amines Chemical class 0.000 description 15
• IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 15
• 150000003254 radicals Chemical class 0.000 description 15
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 15
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• 238000000926 separation method Methods 0.000 description 14
• 241000124008 Mammalia Species 0.000 description 13
• 239000008280 blood Substances 0.000 description 13
• 210000004369 blood Anatomy 0.000 description 13
• 229940002612 prodrug Drugs 0.000 description 13
• 239000000651 prodrug Substances 0.000 description 13
• 230000001225 therapeutic effect Effects 0.000 description 13
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 12
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 12
• 125000003118 aryl group Chemical group 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
• 239000004215 Carbon black (E152) Substances 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 229930195733 hydrocarbon Natural products 0.000 description 11
• 238000004519 manufacturing process Methods 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 238000010992 reflux Methods 0.000 description 11
• 238000012360 testing method Methods 0.000 description 11
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 239000003112 inhibitor Substances 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 239000000546 pharmaceutical excipient Substances 0.000 description 10
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 9
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
• 229910052736 halogen Inorganic materials 0.000 description 9
• 150000002367 halogens Chemical class 0.000 description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 9
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 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
• 206010006895 Cachexia Diseases 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 125000000753 cycloalkyl group Chemical group 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• 150000004820 halides Chemical class 0.000 description 8
• 239000002207 metabolite Substances 0.000 description 8
• 238000010898 silica gel chromatography Methods 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
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