BR112016024467B1 - Compostos e métodos para a prevenção ou o tratamento da malária - Google Patents

Info

Publication number

BR112016024467B1

BR112016024467B1 BR112016024467-2A BR112016024467A BR112016024467B1 BR 112016024467 B1 BR112016024467 B1 BR 112016024467B1 BR 112016024467 A BR112016024467 A BR 112016024467A BR 112016024467 B1 BR112016024467 B1 BR 112016024467B1

Authority

BR

Brazil

Prior art keywords

methyl

cyclopropyl

diamine

fluoro

pyridyl

Prior art date

2014-04-28

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 127
• 238000000034 method Methods 0.000 title abstract description 57
• 201000004792 malaria Diseases 0.000 title abstract description 29
• 238000011282 treatment Methods 0.000 title abstract description 27
• 230000002265 prevention Effects 0.000 title abstract description 7
• 150000003839 salts Chemical class 0.000 claims abstract description 47
• 239000000203 mixture Substances 0.000 claims description 44
• 239000008194 pharmaceutical composition Substances 0.000 claims description 27
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 claims description 11
• 229960003677 chloroquine Drugs 0.000 claims description 11
• 239000002207 metabolite Substances 0.000 claims description 11
• WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 claims description 10
• 239000003430 antimalarial agent Substances 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 239000000460 chlorine Chemical group 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 claims description 5
• OVCDSSHSILBFBN-UHFFFAOYSA-N Amodiaquine Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C3=CC=C(Cl)C=C3N=CC=2)=C1 OVCDSSHSILBFBN-UHFFFAOYSA-N 0.000 claims description 5
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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• 238000005576 amination reaction Methods 0.000 claims description 3
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• 229930101531 artemisinin Natural products 0.000 claims description 3
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• XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• DLYPREQTTOHKSM-UHFFFAOYSA-N 7-chloro-n-[[2-[(dimethylamino)methyl]cyclopenta-1,4-dien-1-yl]methyl]quinolin-4-amine;cyclopenta-1,3-diene;iron(2+) Chemical compound [Fe+2].C1C=CC=[C-]1.C1=[C-]CC(CN(C)C)=C1CNC1=CC=NC2=CC(Cl)=CC=C12 DLYPREQTTOHKSM-UHFFFAOYSA-N 0.000 claims description 2
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