MXPA06000882A

MXPA06000882A - Derivados de quinolina y su uso en terapia.

Derivados de quinolina y su uso en terapia.

Info

Publication number: MXPA06000882A
Authority: MX; Mexico
Prior art keywords: chloro; formula; compound; group; quinolinyl
Prior art date: 2003-07-28

Application number

MXPA06000882A

Other languages

English (en)

Spanish (es)

Inventor

Paul Willis

Original Assignee

Astrazeneca Ab

Priority date

2003-07-28

Filing date

2004-07-21

Publication date

2006-03-30

2004-07-21 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2006-03-30 Publication of MXPA06000882A publication Critical patent/MXPA06000882A/es

Links

238000002560 therapeutic procedure Methods 0.000 title claims abstract description 9
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 203
238000000034 method Methods 0.000 claims abstract description 58
230000008569 process Effects 0.000 claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 6
-1 substituent halogen Chemical class 0.000 claims description 110
125000001424 substituent group Chemical group 0.000 claims description 93
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 71
229910052739 hydrogen Inorganic materials 0.000 claims description 67
229910052736 halogen Inorganic materials 0.000 claims description 66
150000002367 halogens Chemical class 0.000 claims description 65
239000001257 hydrogen Substances 0.000 claims description 63
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 63
125000000217 alkyl group Chemical group 0.000 claims description 52
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 48
229910052757 nitrogen Inorganic materials 0.000 claims description 47
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
125000003545 alkoxy group Chemical group 0.000 claims description 43
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
125000000623 heterocyclic group Chemical group 0.000 claims description 38
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
150000003839 salts Chemical class 0.000 claims description 35
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 31
238000011282 treatment Methods 0.000 claims description 30
229910052717 sulfur Chemical group 0.000 claims description 29
125000005842 heteroatom Chemical group 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
229910052760 oxygen Inorganic materials 0.000 claims description 27
239000012453 solvate Substances 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 25
125000004122 cyclic group Chemical group 0.000 claims description 25
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
239000011593 sulfur Chemical group 0.000 claims description 23
125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
125000004414 alkyl thio group Chemical group 0.000 claims description 20
229920006395 saturated elastomer Polymers 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 19
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
239000000377 silicon dioxide Substances 0.000 claims description 12
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
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 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
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
239000003814 drug Substances 0.000 claims description 9
125000003831 tetrazolyl group Chemical group 0.000 claims description 8
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 7
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 7
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
239000002671 adjuvant Substances 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
201000008482 osteoarthritis Diseases 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
KCWSDKICODBYRE-UHFFFAOYSA-N 1-[6-chloro-5-(2-phenylethylcarbamoyl)quinolin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=CC=C(C(C(=O)NCCC=2C=CC=CC=2)=C(Cl)C=C2)C2=N1 KCWSDKICODBYRE-UHFFFAOYSA-N 0.000 claims description 4
PPDLJZBXSGMJNN-UHFFFAOYSA-N 1-[6-chloro-5-[2-(4-chlorophenyl)ethylcarbamoyl]quinolin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=CC=C(C(C(=O)NCCC=2C=CC(Cl)=CC=2)=C(Cl)C=C2)C2=N1 PPDLJZBXSGMJNN-UHFFFAOYSA-N 0.000 claims description 4
208000006545 Chronic Obstructive Pulmonary Disease 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
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 claims description 4
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
230000000414 obstructive effect Effects 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
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
201000001320 Atherosclerosis Diseases 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 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
201000010099 disease Diseases 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 3
FWEPRJAGHDPQGK-UHFFFAOYSA-N n-(6-chloro-2-piperazin-1-ylquinolin-5-yl)-3-phenylpropanamide Chemical compound ClC1=CC=C2N=C(N3CCNCC3)C=CC2=C1NC(=O)CCC1=CC=CC=C1 FWEPRJAGHDPQGK-UHFFFAOYSA-N 0.000 claims description 3
QIPHOMBDWJEGDN-HNNXBMFYSA-N n-[2-[(3s)-3-aminopyrrolidin-1-yl]-6-chloroquinolin-5-yl]-3-(2-chlorophenyl)propanamide Chemical compound C1[C@@H](N)CCN1C1=CC=C(C(NC(=O)CCC=2C(=CC=CC=2)Cl)=C(Cl)C=C2)C2=N1 QIPHOMBDWJEGDN-HNNXBMFYSA-N 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
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
125000004432 carbon atom Chemical group C* 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
208000023504 respiratory system disease Diseases 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
241001024304 Mino Species 0.000 claims 1
125000004344 phenylpropyl group Chemical group 0.000 claims 1
ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 183
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 162
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
239000007787 solid Substances 0.000 description 58
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
238000000746 purification Methods 0.000 description 41
239000003480 eluent Substances 0.000 description 39
239000000243 solution Substances 0.000 description 36
239000000203 mixture Substances 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
229910052681 coesite Inorganic materials 0.000 description 30
229910052906 cristobalite Inorganic materials 0.000 description 30
229910052682 stishovite Inorganic materials 0.000 description 30
229910052905 tridymite Inorganic materials 0.000 description 30
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
238000001914 filtration Methods 0.000 description 17
239000003112 inhibitor Substances 0.000 description 17
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 16
150000002148 esters Chemical class 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 13
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
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 13
239000002904 solvent Substances 0.000 description 13
102100037602 P2X purinoceptor 7 Human genes 0.000 description 12
101710189965 P2X purinoceptor 7 Proteins 0.000 description 12
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
229910052794 bromium Inorganic materials 0.000 description 11
125000001309 chloro group Chemical group Cl* 0.000 description 11
239000011630 iodine Substances 0.000 description 11
229910052740 iodine Inorganic materials 0.000 description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
229910052731 fluorine Inorganic materials 0.000 description 10
239000011737 fluorine Substances 0.000 description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 9
239000000284 extract Substances 0.000 description 9
235000012239 silicon dioxide Nutrition 0.000 description 9
239000000725 suspension Substances 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
239000005557 antagonist Substances 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
239000002585 base Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000000047 product Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
229910021529 ammonia Inorganic materials 0.000 description 6
125000001246 bromo group Chemical group Br* 0.000 description 6
125000001153 fluoro group Chemical group F* 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
238000001953 recrystallisation Methods 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
125000004494 ethyl ester group Chemical group 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
125000002346 iodo group Chemical group I* 0.000 description 5
125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 5
229940044551 receptor antagonist Drugs 0.000 description 5
239000002464 receptor antagonist Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
239000005695 Ammonium acetate Substances 0.000 description 4
208000022559 Inflammatory bowel disease Diseases 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
235000019257 ammonium acetate Nutrition 0.000 description 4
229940043376 ammonium acetate Drugs 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
230000000694 effects Effects 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
239000003960 organic solvent Substances 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
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