BRPI0614758A2 - rifamicinas fosfonadas e usos destas para a prevenção e tratamento de infecções na articulação e osso - Google Patents

Info

Publication number

BRPI0614758A2

BRPI0614758A2 BRPI0614758-5A BRPI0614758A BRPI0614758A2 BR PI0614758 A2 BRPI0614758 A2 BR PI0614758A2 BR PI0614758 A BRPI0614758 A BR PI0614758A BR PI0614758 A2 BRPI0614758 A2 BR PI0614758A2

Authority

BR

Brazil

Prior art keywords

formula

group

rifamycin

original document

substituted

Prior art date

2005-08-11

Links

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• 229930189077 Rifamycin Natural products 0.000 title claims abstract description 149
• 238000011282 treatment Methods 0.000 title claims abstract description 63
• HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 title claims description 142
• 229960003292 rifamycin Drugs 0.000 title claims description 135
• 206010031252 Osteomyelitis Diseases 0.000 title abstract description 27
• 230000002265 prevention Effects 0.000 title abstract description 10
• 206010060968 Arthritis infective Diseases 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 213
• 210000000988 bone and bone Anatomy 0.000 claims abstract description 113
• 239000003242 anti bacterial agent Substances 0.000 claims abstract description 59
• 238000000034 method Methods 0.000 claims abstract description 56
• 238000011321 prophylaxis Methods 0.000 claims abstract description 21
• 229940122361 Bisphosphonate Drugs 0.000 claims description 89
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 150000004663 bisphosphonates Chemical group 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 40
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
• 125000003118 aryl group Chemical group 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 239000003446 ligand Substances 0.000 claims description 35
• 239000008194 pharmaceutical composition Substances 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 230000000844 anti-bacterial effect Effects 0.000 claims description 25
• 125000001424 substituent group Chemical group 0.000 claims description 25
• 230000000845 anti-microbial effect Effects 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• 239000004599 antimicrobial Substances 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 208000035143 Bacterial infection Diseases 0.000 claims description 17
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 17
• 229960001225 rifampicin Drugs 0.000 claims description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 15
• SGHWBDUXKUSFOP-KYALZUAASA-N rifalazil Chemical class O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)N=C2C(=O)C=3C(O)=C4C)C)OC)C4=C1C=3C(NC1=C(O)C=3)=C2OC1=CC=3N1CCN(CC(C)C)CC1 SGHWBDUXKUSFOP-KYALZUAASA-N 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
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• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 239000004098 Tetracycline Substances 0.000 claims description 11
• 235000019364 tetracycline Nutrition 0.000 claims description 11
• 150000003522 tetracyclines Chemical class 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 150000003053 piperidines Chemical class 0.000 claims description 8
• NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical class OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 claims description 8
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• 229930101283 tetracycline Natural products 0.000 claims description 8
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• 108010059993 Vancomycin Proteins 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• UECIPBUIMXSXEI-BNSVOVDNSA-N eremomycin Chemical compound O([C@@H]1C2=CC=C(C=C2)OC=2C=C3C=C(C=2O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@@](C)(N)C2)OC2=CC=C(C=C2Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1 UECIPBUIMXSXEI-BNSVOVDNSA-N 0.000 claims description 7
• 108010013356 eremomycin Proteins 0.000 claims description 7
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• 150000002780 morpholines Chemical class 0.000 claims description 7
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• 229960003040 rifaximin Drugs 0.000 claims description 7
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• MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims description 7
• 108010013198 Daptomycin Proteins 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 claims description 6
• WDZCUPBHRAEYDL-GZAUEHORSA-N rifapentine Chemical class O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N(CC1)CCN1C1CCCC1 WDZCUPBHRAEYDL-GZAUEHORSA-N 0.000 claims description 6
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