CA2511189A1

CA2511189A1 - Benzamide inhibitors of the p2x7 receptor

Benzamide inhibitors of the p2x7 receptor Download PDF

Info

Publication number: CA2511189A1
Authority: CA; Canada
Prior art keywords: alkyl; hydroxy; methyl; cycloalkyl; formula
Prior art date: 2002-12-31
Legal status : Abandoned

Application number

CA002511189A

Other languages

English (en)

French (fr)

Inventor

Allen J. Duplantier

Chakrapani Subramanyam

Mark A. Dombroski

Current Assignee

Pfizer Products Inc

Original Assignee

Individual

Priority date

2002-12-31

Filing date

2003-12-30

Publication date

2004-07-15

2003-12-30 Application filed by Individual filed Critical Individual

2004-07-15 Publication of CA2511189A1 publication Critical patent/CA2511189A1/en

Status Abandoned legal-status Critical Current

Links

KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title abstract description 22
239000003112 inhibitor Substances 0.000 title abstract description 17
102100037602 P2X purinoceptor 7 Human genes 0.000 title abstract description 3
101710189965 P2X purinoceptor 7 Proteins 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 259
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
102000000589 Interleukin-1 Human genes 0.000 claims abstract description 12
108010002352 Interleukin-1 Proteins 0.000 claims abstract description 12
230000001404 mediated effect Effects 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims description 294
229910052736 halogen Inorganic materials 0.000 claims description 122
150000002367 halogens Chemical class 0.000 claims description 122
229910052739 hydrogen Inorganic materials 0.000 claims description 109
239000001257 hydrogen Substances 0.000 claims description 109
125000000623 heterocyclic group Chemical group 0.000 claims description 104
-1 CN- Chemical group 0.000 claims description 101
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 93
229910052757 nitrogen Inorganic materials 0.000 claims description 92
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 91
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 81
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 66
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 64
125000001424 substituent group Chemical group 0.000 claims description 44
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
150000003839 salts Chemical class 0.000 claims description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
238000000034 method Methods 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
229940002612 prodrug Drugs 0.000 claims description 20
239000000651 prodrug Substances 0.000 claims description 20
239000012453 solvate Substances 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
241000124008 Mammalia Species 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
150000002431 hydrogen Chemical group 0.000 claims description 7
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
RCTDSGVXRWTORZ-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-(3-oxo-1h-1,2,4-triazol-2-yl)benzamide Chemical compound C=1C(N2C(NC=N2)=O)=CC=C(Cl)C=1C(=O)NCC1(O)CCCCCC1 RCTDSGVXRWTORZ-UHFFFAOYSA-N 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
RGQPEMBJOFTNNB-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-3-methoxypropyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]benzamide Chemical compound O=C1N(CC(O)COC)C(C)=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 RGQPEMBJOFTNNB-UHFFFAOYSA-N 0.000 claims description 3
BSEXMMRAAYVYCM-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-methoxyethyl)-5-oxo-1,2,4-triazol-1-yl]benzamide Chemical compound O=C1N(CCOC)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 BSEXMMRAAYVYCM-UHFFFAOYSA-N 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
RFPJMKABSJEKPH-UHFFFAOYSA-N 2-chloro-5-[4-(cyanomethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound O=C1N(CC#N)C(C)=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 RFPJMKABSJEKPH-UHFFFAOYSA-N 0.000 claims description 2
UKDIGJHGQVHHHP-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxy-3,3-dimethylcyclohexyl)methyl]-5-(5-methyl-3-oxo-1h-1,2,4-triazol-2-yl)benzamide Chemical compound O=C1NC(C)=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CC(C)(C)CCC2)=C1 UKDIGJHGQVHHHP-UHFFFAOYSA-N 0.000 claims description 2
ODDRUCRDLYREEQ-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-2-methylpropyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]benzamide Chemical compound O=C1N(CC(C)(C)O)C(C)=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 ODDRUCRDLYREEQ-UHFFFAOYSA-N 0.000 claims description 2
FHLQCVGMVRPOSI-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxyethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]benzamide Chemical compound O=C1N(CCO)C(C)=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 FHLQCVGMVRPOSI-UHFFFAOYSA-N 0.000 claims description 2
MRMLNNAIOKJQAQ-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxyethyl)-5-oxo-1,2,4-triazol-1-yl]benzamide Chemical compound O=C1N(CCO)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 MRMLNNAIOKJQAQ-UHFFFAOYSA-N 0.000 claims description 2
CSWDVEPPNDYGGX-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-methoxyethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]benzamide Chemical compound O=C1N(CCOC)C(C)=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 CSWDVEPPNDYGGX-UHFFFAOYSA-N 0.000 claims description 2
QDEDDXCROYTHCC-UHFFFAOYSA-N 5-[4-(2-amino-2-oxoethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-2-chloro-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound O=C1N(CC(N)=O)C(C)=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 QDEDDXCROYTHCC-UHFFFAOYSA-N 0.000 claims description 2
JZGBEXCGSAJKCR-UHFFFAOYSA-N 5-[4-(2-aminoethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-2-chloro-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound O=C1N(CCN)C(C)=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 JZGBEXCGSAJKCR-UHFFFAOYSA-N 0.000 claims description 2
150000002829 nitrogen Chemical class 0.000 claims description 2
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 9
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 7
125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims 6
125000000041 C6-C10 aryl group Chemical group 0.000 claims 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
YOSWOAOSZWTECO-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-(5-methyl-3-oxo-1h-1,2,4-triazol-2-yl)benzamide Chemical compound O=C1NC(C)=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 YOSWOAOSZWTECO-UHFFFAOYSA-N 0.000 claims 1
208000035475 disorder Diseases 0.000 abstract description 8
201000008482 osteoarthritis Diseases 0.000 abstract description 6
206010039073 rheumatoid arthritis Diseases 0.000 abstract description 6
208000006673 asthma Diseases 0.000 abstract description 5
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract description 4
208000023275 Autoimmune disease Diseases 0.000 abstract description 3
206010020751 Hypersensitivity Diseases 0.000 abstract description 3
206010028980 Neoplasm Diseases 0.000 abstract description 3
208000006011 Stroke Diseases 0.000 abstract description 3
201000011510 cancer Diseases 0.000 abstract description 3
208000027866 inflammatory disease Diseases 0.000 abstract description 3
208000010125 myocardial infarction Diseases 0.000 abstract description 3
230000007815 allergy Effects 0.000 abstract description 2
230000010410 reperfusion Effects 0.000 abstract description 2
125000000753 cycloalkyl group Chemical group 0.000 description 167
125000003545 alkoxy group Chemical group 0.000 description 74
125000003118 aryl group Chemical group 0.000 description 63
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
238000006243 chemical reaction Methods 0.000 description 35
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
238000002360 preparation method Methods 0.000 description 18
239000002585 base Substances 0.000 description 17
239000000203 mixture Substances 0.000 description 17
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
108020003175 receptors Proteins 0.000 description 14
102000005962 receptors Human genes 0.000 description 14
210000004027 cell Anatomy 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
125000003342 alkenyl group Chemical group 0.000 description 12
125000001072 heteroaryl group Chemical group 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000443 aerosol Substances 0.000 description 11
125000000304 alkynyl group Chemical group 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000005557 antagonist Substances 0.000 description 9
125000001309 chloro group Chemical group Cl* 0.000 description 9
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
125000004104 aryloxy group Chemical group 0.000 description 8
235000019253 formic acid Nutrition 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000002609 medium Substances 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
BURJIEWNHIKROD-FWDYTFEUSA-N [[(2r,3r,4r,5s)-5-(6-aminopurin-9-yl)-4,5-dibenzoyl-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O=C([C@@]1(O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@]1(N1C=2N=CN=C(C=2N=C1)N)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 BURJIEWNHIKROD-FWDYTFEUSA-N 0.000 description 6
125000000539 amino acid group Chemical group 0.000 description 6
239000003814 drug Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000009472 formulation Methods 0.000 description 6
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
230000008569 process Effects 0.000 description 6
229940044551 receptor antagonist Drugs 0.000 description 6
239000002464 receptor antagonist Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
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206010001052 Acute respiratory distress syndrome Diseases 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 4
206010040070 Septic Shock Diseases 0.000 description 4
239000002671 adjuvant Substances 0.000 description 4
201000000028 adult respiratory distress syndrome Diseases 0.000 description 4
239000000556 agonist Substances 0.000 description 4
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
229910000024 caesium carbonate Inorganic materials 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
229940111134 coxibs Drugs 0.000 description 4
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 4
ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 4
229960005542 ethidium bromide Drugs 0.000 description 4
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000004007 reversed phase HPLC Methods 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
201000001320 Atherosclerosis Diseases 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
208000001132 Osteoporosis Diseases 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
201000004681 Psoriasis Diseases 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
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IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 2
MMSNEKOTSJRTRI-LLVKDONJSA-N 1-[(2r)-4-[5-[(4-fluorophenyl)methyl]thiophen-2-yl]but-3-yn-2-yl]-1-hydroxyurea Chemical compound S1C(C#C[C@@H](C)N(O)C(N)=O)=CC=C1CC1=CC=C(F)C=C1 MMSNEKOTSJRTRI-LLVKDONJSA-N 0.000 description 2
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 2
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