MXPA05007130A

MXPA05007130A - Inhibidores benzamida del receptor p2x7.

Inhibidores benzamida del receptor p2x7.

Info

Publication number: MXPA05007130A
Authority: MX; Mexico
Prior art keywords: alkyl; hydroxy; methyl; cycloalkyl; formula
Prior art date: 2002-12-31

Application number

MXPA05007130A

Other languages

English (en)

Spanish (es)

Inventor

Mark A Dombroski

Original Assignee

Pfizer Prod Inc

Priority date

2002-12-31

Filing date

2003-12-30

Publication date

2005-08-26

2003-12-30 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2005-08-26 Publication of MXPA05007130A publication Critical patent/MXPA05007130A/es

Links

KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title claims abstract description 10
239000003112 inhibitor Substances 0.000 title abstract description 20
102100037602 P2X purinoceptor 7 Human genes 0.000 title abstract description 19
101710189965 P2X purinoceptor 7 Proteins 0.000 title abstract description 19
150000001875 compounds Chemical class 0.000 claims abstract description 257
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
102000000589 Interleukin-1 Human genes 0.000 claims abstract description 8
108010002352 Interleukin-1 Proteins 0.000 claims abstract description 8
230000001404 mediated effect Effects 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims description 334
-1 CN- Chemical group 0.000 claims description 244
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 151
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 126
229910052736 halogen Inorganic materials 0.000 claims description 122
150000002367 halogens Chemical class 0.000 claims description 121
125000000623 heterocyclic group Chemical group 0.000 claims description 110
229910052739 hydrogen Inorganic materials 0.000 claims description 108
239000001257 hydrogen Substances 0.000 claims description 108
229910052757 nitrogen Inorganic materials 0.000 claims description 86
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
125000000753 cycloalkyl group Chemical group 0.000 claims description 70
125000003545 alkoxy group Chemical group 0.000 claims description 68
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 67
125000003118 aryl group Chemical group 0.000 claims description 50
125000001424 substituent group Chemical group 0.000 claims description 44
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 28
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 25
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 20
229940002612 prodrug Drugs 0.000 claims description 20
239000000651 prodrug Substances 0.000 claims description 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
239000012453 solvate Substances 0.000 claims description 14
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 13
125000001153 fluoro group Chemical group F* 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 9
150000002431 hydrogen Chemical group 0.000 claims description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
150000002829 nitrogen Chemical class 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
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 1
239000012678 infectious agent Substances 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
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract description 5
208000006673 asthma Diseases 0.000 abstract description 5
206010020751 Hypersensitivity Diseases 0.000 abstract description 4
208000023275 Autoimmune disease 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
208000010125 myocardial infarction Diseases 0.000 abstract description 3
230000007815 allergy Effects 0.000 abstract description 2
208000027866 inflammatory disease Diseases 0.000 abstract description 2
208000028867 ischemia Diseases 0.000 abstract description 2
230000010410 reperfusion Effects 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 83
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
238000006243 chemical reaction Methods 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
238000000034 method Methods 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
239000000203 mixture Substances 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
239000002585 base Substances 0.000 description 17
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
210000004027 cell Anatomy 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 11
239000002253 acid Substances 0.000 description 11
239000000443 aerosol Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
239000003795 chemical substances by application 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
125000004104 aryloxy group Chemical group 0.000 description 8
235000019253 formic acid Nutrition 0.000 description 8
239000002609 medium Substances 0.000 description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
239000000725 suspension Substances 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
125000000539 amino acid group Chemical group 0.000 description 6
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000009472 formulation 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
125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 5
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
239000000556 agonist Substances 0.000 description 5
229910000024 caesium carbonate Inorganic materials 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
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
125000003277 amino group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000460 chlorine 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
210000002540 macrophage Anatomy 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
229920000642 polymer Polymers 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
229940044551 receptor antagonist Drugs 0.000 description 4
239000002464 receptor antagonist Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011734 sodium Substances 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
239000003981 vehicle Substances 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
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-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
229910019142 PO4 Inorganic materials 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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
208000010668 atopic eczema Diseases 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
210000004698 lymphocyte Anatomy 0.000 description 3
238000012423 maintenance Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229960000485 methotrexate Drugs 0.000 description 3
210000001616 monocyte Anatomy 0.000 description 3
125000002757 morpholinyl group Chemical group 0.000 description 3
239000006199 nebulizer Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000004007 reversed phase HPLC Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
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
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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
VSCBATMPTLKTOV-UHFFFAOYSA-N 2-tert-butylimino-n,n-diethyl-1,3-dimethyl-1,3,2$l^{5}-diazaphosphinan-2-amine Chemical compound CCN(CC)P1(=NC(C)(C)C)N(C)CCCN1C VSCBATMPTLKTOV-UHFFFAOYSA-N 0.000 description 2
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
BRMWTNUJHUMWMS-UHFFFAOYSA-N 3-Methylhistidine Natural products CN1C=NC(CC(N)C(O)=O)=C1 BRMWTNUJHUMWMS-UHFFFAOYSA-N 0.000 description 2
229940124125 5 Lipoxygenase inhibitor Drugs 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
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