BRPI0905601A2 - compostos de etinilindol - Google Patents

Info

Publication number

BRPI0905601A2

BRPI0905601A2 BRPI0905601-7A BRPI0905601A BRPI0905601A2 BR PI0905601 A2 BRPI0905601 A2 BR PI0905601A2 BR PI0905601 A BRPI0905601 A BR PI0905601A BR PI0905601 A2 BRPI0905601 A2 BR PI0905601A2

Authority

BR

Brazil

Prior art keywords

methyl

compound

indol

phenyl

butoxy

Prior art date

2008-12-22

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 324
• -1 3-carboxypropyl group Chemical group 0.000 claims description 135
• 239000002253 acid Substances 0.000 claims description 64
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 239000012453 solvate Substances 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 229940002612 prodrug Drugs 0.000 claims description 12
• 239000000651 prodrug Substances 0.000 claims description 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [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 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 4
• 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 4
• CUZTUQOWAJAZCQ-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C1=CC=C2C(CCCC(=O)O)=CN(CCCC(O)=O)C2=C1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F CUZTUQOWAJAZCQ-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• TXTOGNHBXCXSDY-UHFFFAOYSA-N 2-[1-[[1-(carboxymethyl)-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]methyl]cyclopropyl]acetic acid Chemical compound C12=CC=CC(C#CC=3C=CC(OCCCCC=4C(=C(F)C(F)=C(F)C=4F)F)=CC=3)=C2N(CC(O)=O)C(C)=C1CC1(CC(O)=O)CC1 TXTOGNHBXCXSDY-UHFFFAOYSA-N 0.000 claims 1
• URNRXOPHGYWKLX-UHFFFAOYSA-N 2-[1-[[1-(carboxymethyl)-7-[2-[4-[4-(3-chloro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]methyl]cyclopropyl]acetic acid Chemical compound C12=CC=CC(C#CC=3C=CC(OCCCCC=4C(=C(Cl)C=CC=4)C)=CC=3)=C2N(CC(O)=O)C(C)=C1CC1(CC(O)=O)CC1 URNRXOPHGYWKLX-UHFFFAOYSA-N 0.000 claims 1
• PYUVJTWRSZWPDP-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,5-tetrafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC(F)=C(F)C(F)=C1F PYUVJTWRSZWPDP-UHFFFAOYSA-N 0.000 claims 1
• HUIIHFBKBWWWJM-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C=C(F)C(F)=C1F HUIIHFBKBWWWJM-UHFFFAOYSA-N 0.000 claims 1
• OKNHXOCNFKQLBL-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-4-fluoro-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F OKNHXOCNFKQLBL-UHFFFAOYSA-N 0.000 claims 1
• SILHYVDKGHXGBL-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-4-fluoro-7-[2-[4-[4-(3-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=CC(F)=C1C SILHYVDKGHXGBL-UHFFFAOYSA-N 0.000 claims 1
• FHIWKHKLAOPBDE-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(3-chloro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=CC(Cl)=C1C FHIWKHKLAOPBDE-UHFFFAOYSA-N 0.000 claims 1
• AWYSEGZBFYYQQL-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(3-chloro-2-methylphenyl)butoxy]phenyl]ethynyl]-4-fluoro-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=CC(Cl)=C1C AWYSEGZBFYYQQL-UHFFFAOYSA-N 0.000 claims 1
• YWFJJZNSTFOQLJ-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(4-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=C(F)C=C1C YWFJJZNSTFOQLJ-UHFFFAOYSA-N 0.000 claims 1
• WUTFKAOZFRKFGO-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(4-fluoro-3-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=C(F)C(C)=C1 WUTFKAOZFRKFGO-UHFFFAOYSA-N 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 21
• 230000003042 antagnostic effect Effects 0.000 abstract description 16
• 208000006673 asthma Diseases 0.000 abstract description 16
• 201000010099 disease Diseases 0.000 abstract description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 10
• 208000030603 inherited susceptibility to asthma Diseases 0.000 abstract description 9
• 230000005923 long-lasting effect Effects 0.000 abstract description 8
• 230000003389 potentiating effect Effects 0.000 abstract description 8
• 208000023504 respiratory system disease Diseases 0.000 abstract description 7
• 206010011224 Cough Diseases 0.000 abstract description 6
• 230000002265 prevention Effects 0.000 abstract description 6
• 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 abstract description 5
• 206010039085 Rhinitis allergic Diseases 0.000 abstract description 4
• 201000010105 allergic rhinitis Diseases 0.000 abstract description 4
• 208000005069 pulmonary fibrosis Diseases 0.000 abstract description 4
• 201000009890 sinusitis Diseases 0.000 abstract description 4
• 206010006458 Bronchitis chronic Diseases 0.000 abstract description 3
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract description 3
• 206010014561 Emphysema Diseases 0.000 abstract description 3
• 206010035664 Pneumonia Diseases 0.000 abstract description 3
• 206010006451 bronchitis Diseases 0.000 abstract description 3
• 208000007451 chronic bronchitis Diseases 0.000 abstract description 3
• 201000002859 sleep apnea Diseases 0.000 abstract description 3
• 206010009137 Chronic sinusitis Diseases 0.000 abstract description 2
• 208000029523 Interstitial Lung disease Diseases 0.000 abstract description 2
• 208000013116 chronic cough Diseases 0.000 abstract description 2
• 208000027157 chronic rhinosinusitis Diseases 0.000 abstract description 2
• 206010001076 Acute sinusitis Diseases 0.000 abstract 1
• 206010038687 Respiratory distress Diseases 0.000 abstract 1
• 230000001154 acute effect Effects 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 245
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 186
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 183
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 165
• 238000005160 1H NMR spectroscopy Methods 0.000 description 95
• 238000000034 method Methods 0.000 description 75
• 230000000704 physical effect Effects 0.000 description 74
• 239000000243 solution Substances 0.000 description 71
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 66
• 230000002829 reductive effect Effects 0.000 description 58
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 55
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 50
• 238000003756 stirring Methods 0.000 description 45
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 44
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 43
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• 239000000203 mixture Substances 0.000 description 37
• 239000012044 organic layer Substances 0.000 description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• 239000003814 drug Substances 0.000 description 29
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 27
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 27
• 235000019341 magnesium sulphate Nutrition 0.000 description 27
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
• 239000003795 chemical substances by application Substances 0.000 description 23
• 238000001816 cooling Methods 0.000 description 22
• YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 22
• 238000009472 formulation Methods 0.000 description 21
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 18
• 102000005962 receptors Human genes 0.000 description 18
• 108020003175 receptors Proteins 0.000 description 18
• 229940079593 drug Drugs 0.000 description 16
• 238000000605 extraction Methods 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
• 235000011121 sodium hydroxide Nutrition 0.000 description 14
• 239000007787 solid Substances 0.000 description 14
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 13
• 229910000024 caesium carbonate Inorganic materials 0.000 description 13
• 238000006243 chemical reaction Methods 0.000 description 13
• 239000013078 crystal Substances 0.000 description 13
• 238000000634 powder X-ray diffraction Methods 0.000 description 13
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
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• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000007924 injection Substances 0.000 description 12
• 238000002347 injection Methods 0.000 description 12
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• 229940044551 receptor antagonist Drugs 0.000 description 12
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• ZWMQVBSLMQSMDH-UHFFFAOYSA-N (2-bromophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Br ZWMQVBSLMQSMDH-UHFFFAOYSA-N 0.000 description 10
• 206010006482 Bronchospasm Diseases 0.000 description 10
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• 230000007885 bronchoconstriction Effects 0.000 description 10
• 238000000113 differential scanning calorimetry Methods 0.000 description 10
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• 210000004027 cell Anatomy 0.000 description 9
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• 230000005764 inhibitory process Effects 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
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• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
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• 125000001424 substituent group Chemical group 0.000 description 8
• 238000007792 addition Methods 0.000 description 7
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• 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 6
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• 239000000043 antiallergic agent Substances 0.000 description 6
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 238000010576 medium-pressure preparative liquid chromatography Methods 0.000 description 6
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
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• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
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