BRPI0811745B1 - Compostos de 4-(pirrolidin-1-il)quinolina, uso e processo para a preparação dos mesmos, formulação farmacêutica -- - Google Patents

Info

Publication number

BRPI0811745B1

BRPI0811745B1 BRPI0811745-4A BRPI0811745A BRPI0811745B1 BR PI0811745 B1 BRPI0811745 B1 BR PI0811745B1 BR PI0811745 A BRPI0811745 A BR PI0811745A BR PI0811745 B1 BRPI0811745 B1 BR PI0811745B1

Authority

BR

Brazil

Prior art keywords

methyl

phenylpyrrolidin

quinolin

formula

compound

Prior art date

2007-05-17

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 342
• 238000002360 preparation method Methods 0.000 title claims abstract description 36
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
• 238000000034 method Methods 0.000 title claims description 134
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims description 31
• 230000008569 process Effects 0.000 title claims description 6
• 208000015181 infectious disease Diseases 0.000 claims abstract description 52
• 239000003814 drug Substances 0.000 claims abstract description 22
• 230000000813 microbial effect Effects 0.000 claims abstract description 16
• 125000001424 substituent group Chemical group 0.000 claims description 158
• -1 methoxy, ethoxy Chemical group 0.000 claims description 153
• 125000005843 halogen group Chemical group 0.000 claims description 99
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
• 238000006243 chemical reaction Methods 0.000 claims description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
• 229910052740 iodine Inorganic materials 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 20
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
• 239000000460 chlorine Substances 0.000 claims description 16
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 201000004700 rosacea Diseases 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 230000001580 bacterial effect Effects 0.000 claims description 12
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• JSPGOCCUWIFPKZ-UHFFFAOYSA-N n-benzyl-2-methyl-4-(3-phenylpyrrolidin-1-yl)quinolin-6-amine Chemical compound C=12C=C(NCC=3C=CC=CC=3)C=CC2=NC(C)=CC=1N(C1)CCC1C1=CC=CC=C1 JSPGOCCUWIFPKZ-UHFFFAOYSA-N 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
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• 125000005842 heteroatom Chemical group 0.000 claims description 11
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• 201000010099 disease Diseases 0.000 claims description 10
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• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 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 claims description 6
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• CLRGDQOAQCSKCU-UHFFFAOYSA-N 4-[3-(4-methoxyphenyl)pyrrolidin-1-yl]-2-methyl-6-phenoxyquinoline;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1CN(C=2C3=CC(OC=4C=CC=CC=4)=CC=C3N=C(C)C=2)CC1 CLRGDQOAQCSKCU-UHFFFAOYSA-N 0.000 claims description 5
• VIRNFJCOOYYCEL-UHFFFAOYSA-N 4-[[[2-methyl-4-(3-phenylpyrrolidin-1-yl)quinolin-6-yl]amino]methyl]benzonitrile Chemical compound C=12C=C(NCC=3C=CC(=CC=3)C#N)C=CC2=NC(C)=CC=1N(C1)CCC1C1=CC=CC=C1 VIRNFJCOOYYCEL-UHFFFAOYSA-N 0.000 claims description 5
• WSMQKESQZFQMFW-UHFFFAOYSA-N 5-methyl-pyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1 WSMQKESQZFQMFW-UHFFFAOYSA-N 0.000 claims description 5
• BEBQWTBVHVMBOH-UHFFFAOYSA-N 6-chloro-2-methyl-4-(3-phenylpyrrolidin-1-yl)quinoline Chemical compound C=12C=C(Cl)C=CC2=NC(C)=CC=1N(C1)CCC1C1=CC=CC=C1 BEBQWTBVHVMBOH-UHFFFAOYSA-N 0.000 claims description 5
• 241000193738 Bacillus anthracis Species 0.000 claims description 5
• 241000194032 Enterococcus faecalis Species 0.000 claims description 5
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• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
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