ZA200600820B

ZA200600820B - Quinoline derivates and their use in therapy

Quinoline derivates and their use in therapy Download PDF

Info

Publication number: ZA200600820B
Authority: ZA; South Africa
Prior art keywords: formula; compound; chloro; group; quinolinyl
Prior art date: 2003-07-28

Application number

ZA200600820A

Other languages

English (en)

Inventor

Ford Rhonan

Willis Paul

Thompson Toby

Original Assignee

Astrazeneca Ab

Priority date

2003-07-28

Filing date

2006-01-27

Publication date

2007-04-25

2006-01-27 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2007-04-25 Publication of ZA200600820B publication Critical patent/ZA200600820B/en

Links

238000002560 therapeutic procedure Methods 0.000 title claims description 8
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 144
125000001424 substituent group Chemical group 0.000 claims description 96
125000000217 alkyl group Chemical group 0.000 claims description 80
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 71
-1 2-carboxy-phenyl group Chemical group 0.000 claims description 70
229910052736 halogen Inorganic materials 0.000 claims description 65
150000002367 halogens Chemical class 0.000 claims description 65
239000001257 hydrogen Substances 0.000 claims description 61
229910052739 hydrogen Inorganic materials 0.000 claims description 61
125000003545 alkoxy group Chemical group 0.000 claims description 48
229910052757 nitrogen Inorganic materials 0.000 claims description 46
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
125000000623 heterocyclic group Chemical group 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 38
238000000034 method Methods 0.000 claims description 35
238000011282 treatment Methods 0.000 claims description 33
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
239000012453 solvate Substances 0.000 claims description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
229910052760 oxygen Inorganic materials 0.000 claims description 29
239000000203 mixture Substances 0.000 claims description 28
125000005842 heteroatom Chemical group 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
125000004122 cyclic group Chemical group 0.000 claims description 24
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
239000005864 Sulphur Chemical group 0.000 claims description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
239000001301 oxygen Chemical group 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
125000004414 alkyl thio group Chemical group 0.000 claims description 20
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
230000008569 process Effects 0.000 claims description 19
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 12
229920006395 saturated elastomer Polymers 0.000 claims description 12
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000003831 tetrazolyl group Chemical group 0.000 claims description 8
125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
201000008482 osteoarthritis Diseases 0.000 claims description 6
206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
208000027771 Obstructive airways disease Diseases 0.000 claims description 5
239000002671 adjuvant Substances 0.000 claims description 5
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 4
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 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
WNYZCFCQFZXZHF-UHFFFAOYSA-N 1-[6-chloro-5-[2-(2-fluorophenyl)ethylcarbamoyl]quinolin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=CC=C(C(C(=O)NCCC=2C(=CC=CC=2)F)=C(Cl)C=C2)C2=N1 WNYZCFCQFZXZHF-UHFFFAOYSA-N 0.000 claims description 3
125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 3
PXFQSPCEISBBTQ-UHFFFAOYSA-N 6-chloro-2-methyl-n-(2-phenylethyl)quinoline-5-carboxamide Chemical compound ClC=1C=CC2=NC(C)=CC=C2C=1C(=O)NCCC1=CC=CC=C1 PXFQSPCEISBBTQ-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
238000006268 reductive amination reaction Methods 0.000 claims description 3
239000000377 silicon dioxide Substances 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 3
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
208000035475 disorder Diseases 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 2
JLSUJDXRJOLXMV-UHFFFAOYSA-N n-(6-chloro-2-piperazin-1-ylquinolin-5-yl)-3-(2-methoxyphenyl)propanamide Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(Cl)C=CC2=NC(N3CCNCC3)=CC=C12 JLSUJDXRJOLXMV-UHFFFAOYSA-N 0.000 claims description 2
125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims 15
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
GSAGYAQILPUYNV-UHFFFAOYSA-N 1-[6-chloro-5-[2-(2,6-dichlorophenyl)ethylcarbamoyl]quinolin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=CC=C(C(C(=O)NCCC=2C(=CC=CC=2Cl)Cl)=C(Cl)C=C2)C2=N1 GSAGYAQILPUYNV-UHFFFAOYSA-N 0.000 claims 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
PBIWLVXNUJLCQW-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(6-chloro-2-piperazin-1-ylquinolin-5-yl)propanamide Chemical compound C1=CC(Cl)=CC=C1CCC(=O)NC1=C(Cl)C=CC2=NC(N3CCNCC3)=CC=C12 PBIWLVXNUJLCQW-UHFFFAOYSA-N 0.000 claims 1
FKNRDGLGAVYQNE-CYBMUJFWSA-N 6-chloro-2-methyl-n-[(2s)-2-phenylpropyl]quinoline-5-carboxamide Chemical compound C1([C@@H](CNC(=O)C=2C3=CC=C(C)N=C3C=CC=2Cl)C)=CC=CC=C1 FKNRDGLGAVYQNE-CYBMUJFWSA-N 0.000 claims 1
UAVOXGQJGZBOBO-KRWDZBQOSA-N n-[6-chloro-2-[(3s)-3-(2-hydroxyethylamino)pyrrolidin-1-yl]quinolin-5-yl]-3-(2-chlorophenyl)propanamide Chemical compound C1[C@@H](NCCO)CCN1C1=CC=C(C(NC(=O)CCC=2C(=CC=CC=2)Cl)=C(Cl)C=C2)C2=N1 UAVOXGQJGZBOBO-KRWDZBQOSA-N 0.000 claims 1
229910052711 selenium Inorganic materials 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 21
239000000460 chlorine Substances 0.000 description 21
229910052801 chlorine Inorganic materials 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 16
229910052794 bromium Inorganic materials 0.000 description 16
229910052731 fluorine Inorganic materials 0.000 description 16
239000011737 fluorine Substances 0.000 description 16
239000003112 inhibitor Substances 0.000 description 16
239000011630 iodine Substances 0.000 description 16
229910052740 iodine Inorganic materials 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
150000002148 esters Chemical class 0.000 description 14
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
125000006606 n-butoxy group Chemical group 0.000 description 13
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
239000002904 solvent Substances 0.000 description 13
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 12
239000002585 base Substances 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 7
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000005557 antagonist Substances 0.000 description 6
239000011575 calcium Substances 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
229940044551 receptor antagonist Drugs 0.000 description 6
239000002464 receptor antagonist Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 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 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 5
239000000047 product Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229940111134 coxibs Drugs 0.000 description 4
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 4
125000002541 furyl group Chemical group 0.000 description 4
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
125000003386 piperidinyl group Chemical group 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
125000000719 pyrrolidinyl group Chemical group 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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 group 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 description 3
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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
208000001132 Osteoporosis Diseases 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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201000004681 Psoriasis Diseases 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
239000002253 acid Substances 0.000 description 3
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125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
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239000000284 extract Substances 0.000 description 3
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238000001727 in vivo Methods 0.000 description 3
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208000027866 inflammatory disease Diseases 0.000 description 3
230000002757 inflammatory effect Effects 0.000 description 3
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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