SK8682002A3

SK8682002A3 - Use of benzopyrane substituted by benzoic acid for the production of medicament for the treatment of atherosclerosis and pharmaceutical composition

Use of benzopyrane substituted by benzoic acid for the production of medicament for the treatment of atherosclerosis and pharmaceutical composition Download PDF

Info

Publication number: SK8682002A3
Authority: SK; Slovakia
Prior art keywords: alkyl; formula; benzyl; carboxy; phenyl
Prior art date: 2001-06-28

Application number

SK868-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Robert Joseph Aiello

Patricia-Ann Bourassa

Saralyn Lindsey

Original Assignee

Pfizer Prod Inc

Priority date

2001-06-28

Filing date

2002-06-17

Publication date

2004-08-03

2002-06-17 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2004-08-03 Publication of SK8682002A3 publication Critical patent/SK8682002A3/sk

Links

201000001320 Atherosclerosis Diseases 0.000 title claims abstract description 30
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims description 18
239000003814 drug Substances 0.000 title claims description 13
239000005711 Benzoic acid Substances 0.000 title claims description 10
235000010233 benzoic acid Nutrition 0.000 title claims description 10
238000004519 manufacturing process Methods 0.000 title claims description 10
KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical group C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title description 6
241000124008 Mammalia Species 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 8
-1 phenylsulfinyl Chemical group 0.000 claims description 100
230000003902 lesion Effects 0.000 claims description 50
125000001153 fluoro group Chemical group F* 0.000 claims description 44
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000005557 antagonist Substances 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 16
230000015572 biosynthetic process Effects 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
150000003384 small molecules Chemical class 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
230000035605 chemotaxis Effects 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000000460 chlorine Chemical group 0.000 claims description 7
125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
108090000623 proteins and genes Proteins 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 2
230000000692 anti-sense effect Effects 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
150000001559 benzoic acids Chemical class 0.000 claims 4
150000002431 hydrogen Chemical class 0.000 claims 3
150000001875 compounds Chemical class 0.000 abstract description 111
238000000034 method Methods 0.000 abstract description 54
241000282414 Homo sapiens Species 0.000 abstract description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 92
239000000203 mixture Substances 0.000 description 64
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
239000011541 reaction mixture Substances 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 28
238000005481 NMR spectroscopy Methods 0.000 description 28
210000004027 cell Anatomy 0.000 description 26
239000007787 solid Substances 0.000 description 25
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
241000699670 Mus sp. Species 0.000 description 22
239000002552 dosage form Substances 0.000 description 22
239000010410 layer Substances 0.000 description 22
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
239000002585 base Substances 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
239000002904 solvent Substances 0.000 description 20
229940044551 receptor antagonist Drugs 0.000 description 18
239000002464 receptor antagonist Substances 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
230000002829 reductive effect Effects 0.000 description 17
239000012044 organic layer Substances 0.000 description 16
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
230000008569 process Effects 0.000 description 14
238000010992 reflux Methods 0.000 description 14
210000000329 smooth muscle myocyte Anatomy 0.000 description 14
102000003680 Leukotriene B4 receptors Human genes 0.000 description 13
108090000093 Leukotriene B4 receptors Proteins 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
239000003112 inhibitor Substances 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 13
239000012730 sustained-release form Substances 0.000 description 13
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
239000000047 product Substances 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 11
101710155857 C-C motif chemokine 2 Proteins 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
239000012267 brine Substances 0.000 description 11
150000002632 lipids Chemical class 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
239000000725 suspension Substances 0.000 description 11
238000013268 sustained release Methods 0.000 description 11
230000003143 atherosclerotic effect Effects 0.000 description 10
239000002105 nanoparticle Substances 0.000 description 10
101001046686 Homo sapiens Integrin alpha-M Proteins 0.000 description 9
102100022338 Integrin alpha-M Human genes 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
150000001562 benzopyrans Chemical class 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
239000000126 substance Substances 0.000 description 9
SERVTOXIOYSDQO-UHFFFAOYSA-N 2h-chromen-2-ol Chemical group C1=CC=C2C=CC(O)OC2=C1 SERVTOXIOYSDQO-UHFFFAOYSA-N 0.000 description 8
108010037362 Extracellular Matrix Proteins Proteins 0.000 description 8
102000010834 Extracellular Matrix Proteins Human genes 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 8
210000001765 aortic valve Anatomy 0.000 description 8
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 8
239000003480 eluent Substances 0.000 description 8
210000002744 extracellular matrix Anatomy 0.000 description 8
238000001914 filtration Methods 0.000 description 8
210000002540 macrophage Anatomy 0.000 description 8
230000005012 migration Effects 0.000 description 8
238000013508 migration Methods 0.000 description 8
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical group [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
230000035755 proliferation Effects 0.000 description 8
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 7
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 7
102100021943 C-C motif chemokine 2 Human genes 0.000 description 7
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
239000011248 coating agent Substances 0.000 description 7
238000000576 coating method Methods 0.000 description 7
239000011777 magnesium Substances 0.000 description 7
239000011159 matrix material Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
102000013918 Apolipoproteins E Human genes 0.000 description 6
108010025628 Apolipoproteins E Proteins 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 6
239000011260 aqueous acid Substances 0.000 description 6
150000001558 benzoic acid derivatives Chemical group 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
201000010099 disease Diseases 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
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229910052744 lithium Inorganic materials 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
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 6
229920000642 polymer Polymers 0.000 description 6
229940002612 prodrug Drugs 0.000 description 6
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210000001519 tissue Anatomy 0.000 description 6
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
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108010007622 LDL Lipoproteins Proteins 0.000 description 5
NPGIHFRTRXVWOY-UHFFFAOYSA-N Oil red O Chemical compound Cc1ccc(C)c(c1)N=Nc1cc(C)c(cc1C)N=Nc1c(O)ccc2ccccc12 NPGIHFRTRXVWOY-UHFFFAOYSA-N 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
210000000709 aorta Anatomy 0.000 description 5
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150000004820 halides Chemical group 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
239000003446 ligand Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
230000007170 pathology Effects 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
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NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 5
YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 4
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WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 4
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
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239000000010 aprotic solvent Substances 0.000 description 4
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XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical group [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
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MVLMPMUGCWJDLE-UHFFFAOYSA-M dibutylboron trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[B+]CCCC MVLMPMUGCWJDLE-UHFFFAOYSA-M 0.000 description 4
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