BR112014010583A2 - compostos heterocíclicos, seus usos, composição farmacêutica e combinações medicamentosas - Google Patents

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Publication number

BR112014010583A2

BR112014010583A2 BR112014010583A BR112014010583A BR112014010583A2 BR 112014010583 A2 BR112014010583 A2 BR 112014010583A2 BR 112014010583 A BR112014010583 A BR 112014010583A BR 112014010583 A BR112014010583 A BR 112014010583A BR 112014010583 A2 BR112014010583 A2 BR 112014010583A2

Authority

BR

Brazil

Prior art keywords

alkyl

hydrogen

group

phenyl

acid

Prior art date

2011-11-02

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
• 239000000890 drug combination Substances 0.000 title claims abstract description 5
• 150000002391 heterocyclic compounds Chemical class 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 134
• 150000003839 salts Chemical class 0.000 claims abstract description 77
• 239000002253 acid Substances 0.000 claims abstract description 61
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
• 201000010099 disease Diseases 0.000 claims abstract description 21
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 210000004072 lung Anatomy 0.000 claims abstract description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 277
• 239000001257 hydrogen Substances 0.000 claims description 276
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 218
• -1 halogen hydrogen Chemical class 0.000 claims description 120
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
• 150000002431 hydrogen Chemical class 0.000 claims description 52
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 206010006451 bronchitis Diseases 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 19
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 239000013543 active substance Substances 0.000 claims description 14
• 239000003112 inhibitor Substances 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 8
• 239000005557 antagonist Substances 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• 208000007451 chronic bronchitis Diseases 0.000 claims description 8
• 230000000172 allergic effect Effects 0.000 claims description 7
• 150000001450 anions Chemical class 0.000 claims description 7
• 230000001684 chronic effect Effects 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 102100029438 Nitric oxide synthase, inducible Human genes 0.000 claims description 6
• 101710089543 Nitric oxide synthase, inducible Proteins 0.000 claims description 6
• 206010035664 Pneumonia Diseases 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 206010001889 Alveolitis Diseases 0.000 claims description 5
• 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims description 5
• 208000010668 atopic eczema Diseases 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 239000000812 cholinergic antagonist Substances 0.000 claims description 5
• 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims description 5
• 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims description 5
• 206010009137 Chronic sinusitis Diseases 0.000 claims description 4
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 4
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
• 239000000808 adrenergic beta-agonist Substances 0.000 claims description 4
• 208000026935 allergic disease Diseases 0.000 claims description 4
• 201000010105 allergic rhinitis Diseases 0.000 claims description 4
• 230000003454 betamimetic effect Effects 0.000 claims description 4
• 201000009267 bronchiectasis Diseases 0.000 claims description 4
• 208000029771 childhood onset asthma Diseases 0.000 claims description 4
• 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 4
• 239000003246 corticosteroid Substances 0.000 claims description 4
• 229960001334 corticosteroids Drugs 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 229940121647 egfr inhibitor Drugs 0.000 claims description 4
• 239000003623 enhancer Substances 0.000 claims description 4
• 239000002713 epithelial sodium channel blocking agent Substances 0.000 claims description 4
• 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 claims description 4
• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims description 4
• 230000000414 obstructive effect Effects 0.000 claims description 4
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
• 206010052613 Allergic bronchitis Diseases 0.000 claims description 3
• 206010011224 Cough Diseases 0.000 claims description 3
• 206010014561 Emphysema Diseases 0.000 claims description 3
• 206010035742 Pneumonitis Diseases 0.000 claims description 3
• 206010037423 Pulmonary oedema Diseases 0.000 claims description 3
• 208000006682 alpha 1-Antitrypsin Deficiency Diseases 0.000 claims description 3
• 239000000739 antihistaminic agent Substances 0.000 claims description 3
• 229940125715 antihistaminic agent Drugs 0.000 claims description 3
• 229940052760 dopamine agonists Drugs 0.000 claims description 3
• 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 3
• 230000002757 inflammatory effect Effects 0.000 claims description 3
• 239000000463 material Substances 0.000 claims description 3
• 208000005333 pulmonary edema Diseases 0.000 claims description 3
• 230000000241 respiratory effect Effects 0.000 claims description 3
• 208000035143 Bacterial infection Diseases 0.000 claims description 2
• 241000233866 Fungi Species 0.000 claims description 2
• 208000036142 Viral infection Diseases 0.000 claims description 2
• 230000001580 bacterial effect Effects 0.000 claims description 2
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
• 238000012937 correction Methods 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 244000000013 helminth Species 0.000 claims description 2
• 208000037916 non-allergic rhinitis Diseases 0.000 claims description 2
• 210000002345 respiratory system Anatomy 0.000 claims description 2
• 231100000331 toxic Toxicity 0.000 claims description 2
• 230000002588 toxic effect Effects 0.000 claims description 2
• 230000009385 viral infection Effects 0.000 claims description 2
• BTIIGNUPPKUQAP-UHFFFAOYSA-N [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;diperchlorate Chemical compound [O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 BTIIGNUPPKUQAP-UHFFFAOYSA-N 0.000 claims 5
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 3
• 208000000592 Nasal Polyps Diseases 0.000 claims 1
• 150000007513 acids Chemical class 0.000 abstract description 11
• 239000011734 sodium Substances 0.000 abstract description 11
• 230000000144 pharmacologic effect Effects 0.000 abstract description 7
• 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 abstract description 6
• 229910052708 sodium Inorganic materials 0.000 abstract description 6
• 230000002401 inhibitory effect Effects 0.000 abstract description 3
• 150000007529 inorganic bases Chemical class 0.000 abstract description 2
• 150000007530 organic bases Chemical class 0.000 abstract description 2
• 238000000034 method Methods 0.000 description 66
• 239000000203 mixture Substances 0.000 description 64
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
• 239000000543 intermediate Substances 0.000 description 62
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 61
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 49
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 44
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
• 238000004128 high performance liquid chromatography Methods 0.000 description 31
• 239000000243 solution Substances 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 239000007858 starting material Substances 0.000 description 27
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 26
• 239000002904 solvent Substances 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
• 239000012071 phase Substances 0.000 description 22
• 239000011541 reaction mixture Substances 0.000 description 22
• 230000002829 reductive effect Effects 0.000 description 22
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 21
• 239000012453 solvate Substances 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 150000004677 hydrates Chemical class 0.000 description 18
• 229940002612 prodrug Drugs 0.000 description 18
• 239000000651 prodrug Substances 0.000 description 18
• 239000000460 chlorine Substances 0.000 description 17
• 125000005842 heteroatom Chemical group 0.000 description 17
• 239000003643 water by type Substances 0.000 description 17
• 150000002148 esters Chemical class 0.000 description 16
• 125000004432 carbon atom Chemical group C* 0.000 description 15
• 238000001819 mass spectrum Methods 0.000 description 15
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• 125000003118 aryl group Chemical group 0.000 description 13
• 125000004429 atom Chemical group 0.000 description 13
• 150000003254 radicals Chemical class 0.000 description 13
• 125000001424 substituent group Chemical group 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 230000014759 maintenance of location Effects 0.000 description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
• 239000003380 propellant Substances 0.000 description 12
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 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 10
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• 229910052717 sulfur Inorganic materials 0.000 description 10
• 0 *CC(CC[N+](*)*)(CN/C(/N)=N/C(C(C(N)=N)=N)=O)*c1c(*)c(*)c(*)c(*)c1* Chemical compound *CC(CC[N+](*)*)(CN/C(/N)=N/C(C(C(N)=N)=N)=O)*c1c(*)c(*)c(*)c(*)c1* 0.000 description 9
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 9
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
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• 239000000126 substance Substances 0.000 description 8
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• 150000003842 bromide salts Chemical class 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
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• 125000000524 functional group Chemical group 0.000 description 6
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• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
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• 239000000725 suspension Substances 0.000 description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 5
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• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 4
• BPXUIMFOWKBCMM-UHFFFAOYSA-N 3,5-diamino-6-chloro-n-[n'-[[4-(2-phenylethyl)piperidin-4-yl]methyl]carbamimidoyl]pyrazine-2-carboxamide Chemical compound N1=C(Cl)C(N)=NC(N)=C1C(=O)NC(=N)NCC1(CCC=2C=CC=CC=2)CCNCC1 BPXUIMFOWKBCMM-UHFFFAOYSA-N 0.000 description 4
• AGQOIYCTCOEHGR-UHFFFAOYSA-N 5-methyl-1,2-oxazole Chemical compound CC1=CC=NO1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 description 4
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• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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