HRP20190980T1 - Derivati predlijeka (e)-n-metil-n((3-metilbenzofuran-2 il)metil)-3-(7-okso-5,6,7,8-tetrahidro-1,8-naftiridin-3-il)akrilamida - Google Patents
Derivati predlijeka (e)-n-metil-n((3-metilbenzofuran-2 il)metil)-3-(7-okso-5,6,7,8-tetrahidro-1,8-naftiridin-3-il)akrilamida Download PDFInfo
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- HRP20190980T1 HRP20190980T1 HRP20190980TT HRP20190980T HRP20190980T1 HR P20190980 T1 HRP20190980 T1 HR P20190980T1 HR P20190980T T HRP20190980T T HR P20190980TT HR P20190980 T HRP20190980 T HR P20190980T HR P20190980 T1 HRP20190980 T1 HR P20190980T1
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- QXTWSUQCXCWEHF-JXMROGBWSA-N (e)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(7-oxo-6,8-dihydro-5h-1,8-naphthyridin-3-yl)prop-2-enamide Chemical class N1C(=O)CCC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 QXTWSUQCXCWEHF-JXMROGBWSA-N 0.000 title claims 4
- 229940002612 prodrug Drugs 0.000 title 1
- 239000000651 prodrug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 10
- -1 cyano, nitro, azido, sulfhydryl Chemical group 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 229910019142 PO4 Inorganic materials 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 4
- 150000001340 alkali metals Chemical class 0.000 claims 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000003368 amide group Chemical group 0.000 claims 4
- 150000001409 amidines Chemical group 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 150000002466 imines Chemical group 0.000 claims 4
- AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic s-acid Chemical group SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 4
- 239000010452 phosphate Chemical group 0.000 claims 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 4
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 4
- 150000007970 thio esters Chemical group 0.000 claims 4
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical group CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 claims 4
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims 2
- 108010053950 Teicoplanin Proteins 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims 2
- 239000006185 dispersion Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- 238000001990 intravenous administration Methods 0.000 claims 2
- 239000000843 powder Substances 0.000 claims 2
- 229960001608 teicoplanin Drugs 0.000 claims 2
- 238000011200 topical administration Methods 0.000 claims 2
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 claims 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 239000007848 Bronsted acid Substances 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 108010013198 Daptomycin Proteins 0.000 claims 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims 1
- 229930182566 Gentamicin Natural products 0.000 claims 1
- 108010015899 Glycopeptides Proteins 0.000 claims 1
- 102000002068 Glycopeptides Human genes 0.000 claims 1
- 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 claims 1
- 108010004718 Lipoglycopeptides Proteins 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 229930182555 Penicillin Natural products 0.000 claims 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 1
- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229930189077 Rifamycin Natural products 0.000 claims 1
- 108010034396 Streptogramins Proteins 0.000 claims 1
- 239000004098 Tetracycline Substances 0.000 claims 1
- 108010059993 Vancomycin Proteins 0.000 claims 1
- ZWBTYMGEBZUQTK-PVLSIAFMSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(32),2,4,9,19,21,24,26,30-nonaene-28,4'-piperidine]-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c4NC5(CCN(CC(C)C)CC5)N=c4c(=NC(=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]1C)c(O)c2c(O)c3C ZWBTYMGEBZUQTK-PVLSIAFMSA-N 0.000 claims 1
- 229940126575 aminoglycoside Drugs 0.000 claims 1
- 229960003022 amoxicillin Drugs 0.000 claims 1
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims 1
- 229940058936 antimalarials diaminopyrimidines Drugs 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229960005397 arbekacin Drugs 0.000 claims 1
- MKKYBZZTJQGVCD-XTCKQBCOSA-N arbekacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)CC[C@H]1N MKKYBZZTJQGVCD-XTCKQBCOSA-N 0.000 claims 1
- 229960003644 aztreonam Drugs 0.000 claims 1
- WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 229940041011 carbapenems Drugs 0.000 claims 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 claims 1
- 229960003405 ciprofloxacin Drugs 0.000 claims 1
- DOAKLVKFURWEDJ-QCMAZARJSA-N daptomycin Chemical compound C([C@H]1C(=O)O[C@H](C)[C@@H](C(NCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@H](C(=O)N1)[C@H](C)CC(O)=O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCCCCCCCC)C(=O)C1=CC=CC=C1N DOAKLVKFURWEDJ-QCMAZARJSA-N 0.000 claims 1
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- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims 1
- 229960003907 linezolid Drugs 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 1
- 229940041033 macrolides Drugs 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- GPXLMGHLHQJAGZ-JTDSTZFVSA-N nafcillin Chemical compound C1=CC=CC2=C(C(=O)N[C@@H]3C(N4[C@H](C(C)(C)S[C@@H]43)C(O)=O)=O)C(OCC)=CC=C21 GPXLMGHLHQJAGZ-JTDSTZFVSA-N 0.000 claims 1
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- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims 1
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- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical compound C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 claims 1
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- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound 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\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 1
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- 229960003165 vancomycin Drugs 0.000 claims 1
- 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 1
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims 1
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Claims (19)
1. Spoj predstavljen s:
i njegove farmaceutski prihvatljive soli.
2. Spoj prema patentnom zahtjevu 1, naznačen time što je predstavljen s formulom I:
pri čemu,
R1 i R2 su svaki neovisno odabrani iz skupine koju čine vodik, alkalijski metal, NH4+, NH3+-(R3), NH2+-(R3)2, i NH+-(R3)3, ili R1 i R2 uzeti zajedno su zemnoalkalijski metal; i
R3 je neovisno odabran iz skupine koju čine C1-6 alkil-, hidroksil C1-6 alkil-, fenil i benzil; i pri čemu su R1 i R2 poželjno svaki NH3+-CH2CH2OH,
i pri čemu izraz alkil obuhvaća alkilne dijelove koje imaju supstituente koji zamjenjuju vodik na jednom ili više ugljika okosnice ugljikovodika, pri čemu su takvi supstituenti odabrani iz skupine koju čine hidroksil, karbonil, uključujući karboksil, alkoksikarbonil, formil, ili acil, tiokarbonil, uključujući tioester, tioacetat, ili tioformat, alkoksil, fosforil, fosfonat, fosfinat, fosfat, amino, amido, amidin, imin, cijano, nitro, azido, sulfhidril, alkiltio, sulfat, sulfonat, sulfamoil, sulfonamido, sulfonil, heterociklil, aralkil, ili aromatski ili heteroaromatski dio.
3. Spoj prema zahtjevu 2, pri čemu je spoj naznačen time što ima jednu ili više od slijedećih značajki:
(i) R1 i R2 su svaki NH3+-(R3),
(ii) jedan od R1 i R2 je H; i jedan od R1 i R2 je NH4+ ili NH3+-(R3),
(iii) R3 je -CH2CH2OH,
(iv) R1 i R2 su alkalijski metal,
pri čemu je alkalijski metal poželjno odabran iz skupine koju čine litij, natrij i kalij,
(v) R1 i R2 uzeti zajedno su zemnoalkalijski metal,
pri čemu je zemnoalkalijski metal poželjno kalcij ili magnezij.
4. Spoj prema zahtjevu 2, naznačen time što je spoj odabran iz skupine koju čine
(i) spoj predstavljen s:
(ii) spoj predstavljen s:
(iii) spoj predstavljen s:
(iv) spoj predstavljen s:
5. Spoj prema bilo kojem od patentnih zahtjeva 1-4, naznačen time što spoj ima najmanje 2-puta veću oralnu biodostupnost na molarnoj osnovi u usporedbi s (E)-N-metil-N-((3-metilbenzofuran-2-il)metil)-3-(7-okso-5,6,7,8-tetrahidro-1,8-naftiridin-3-il)akrilamidom ili njegovim solima ili pri čemu spoj ima barem 2-puta veću biodostupnost na molarnoj osnovi u usporedbi s p-toluensulfonskom soli (E)-N-metil-N-((3-metilbenzofuran-2-il)metil)-3-(7-okso-5,6,7,8-tetrahidro-1,8-naftiridin-3-il)akrilamida.
6. Farmaceutski pripravak koji sadrži spoj prema kojem od patentnih zahtjeva 1-5 i farmaceutski prihvatljivu pomoćnu tvar, pri čemu je farmaceutski pripravak poželjno nadalje naznačen time što ima jednu ili više od slijedećih značajki:
(i) pripravak je formuliran za jedno od: intravensko davanje, injekcijsko davanje, topikalno davanje, sistemsko davanje, inhalacijsku primjenu ili oralnu primjenu;
(ii) pripravak je prašak, tableta, pilula ili kapsula;
(iii) pripravak je farmaceutski prihvatljiva sterilna izotonična vodena ili nevodena otopina, disperzija, suspenzija ili emulzija, ili sterilni prašak koji se može rekonstituirati u sterilne injekcijske otopine ili disperzije.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5 ili farmaceutski pripravak prema zahtjevu 6, naznačen time što je za uporabu za (a) liječenje bakterijske infekcije kod pacijenta ili (b) liječenje ili ublažavanje cistične fibroze kod pacijenta.
8. Spoj ili farmaceutski pripravak za uporabu prema zahtjevu 7, izvedba (a), naznačen time što liječenje osigurava prosječnu razinu spoja u plazmi koja je najmanje 2 puta veća od one dobivene upotrebom iste količine, (E)-N-metil-N-((3-metilbenzofuran-2-il)metil)-3-(7-okso-5,6,7,8-tetrahidro-1,8-naftiridin-3-il)akrilamida ili njegovih soli, 4 sata nakon upotrebe ili
pri čemu liječenje osigurava prosječnu razinu spoja u plazmi koja je najmanje 2 puta veća od one dobivene primjenom iste količine, na molarnoj osnovi, p-toluensulfonske soli (E)-N-metil-N-((3-metilbenzofuran-2-il)metil)-3-(7-okso-5,6,7,8-tetrahidro-1,8-naftiridin-3-il)akrilamida, 4 sata nakon upotrebe.
9. Spoj ili farmaceutski pripravak za uporabu prema bilo kojem od patentnih zahtjeva 7-8, naznačen time što je pacijent čovjek ili životinja pratilac ili životinja za prehranu.
10. Farmaceutski pripravak za uporabu prema bilo kojem od patentnih zahtjeva 7-9, naznačen time što je navedeno liječenje putem primjene koji je odabran iz skupine koju čine oralna primjena, intravenska primjena, supkutana primjena, topikalna primjena i inhalacija; te poželjno oralnom primjenom; ili injekcijom.
11. Farmaceutski pripravak za uporabu prema bilo kojem od patentnih zahtjeva 7-10, naznačen time što navedena uporaba nadalje sadrži upotrebu spoja odabranog iz skupine koju čine oksazolidinon, lipoglikopeptid, vankomicin, teikoplanin, glikopeptid, penicilin, cefalosporin, pleuromutilin, fusidan, linkozamid, rifamicin, arbekacin, linezolid, daptomicin, teikoplanin, telavancin, sulfametoksazol, gentamicin, ciprofloksin, levofloksin, aztreonam, tobramicin, amoksicilin, nafcilin, rifabutin, rifampin, rifapentin, kinoloni, fluorokinoloni, karbapenemi, aminoglikozidi, aminociklitoli, diaminopirimidini, tetraciklini, gliciklini, streptogramini, makrolidi, i/ili sulfonamidi.
12. Komplet naznačen time što sadrži farmaceutski pripravak prema zahtjevu 6 i upute za njegovu upotrebu.
13. Postupak za pripremanje spoja predstavljenog s formulom II:
naznačen time što postupak sadrži:
dovođenje u kontakt spoja s formulom III sa spojem s formulom IV ili njegovom soli; pri čemu:
formula III je predstavljena s:
formula IV je predstavljena s:
pri čemu:
X predstavlja izlaznu skupinu; i
Pg predstavlja zaštitnu skupinu,
pri čemu je X poželjno odabran iz skupine koja sadrži: halogen,
ili
pri čemu R4 je C1-6alkil-, fenil, benzil, ili haloC1-6alkil-, i pri čemu je X poželjnije klorid, i pri čemu je Pg odabran iz skupine koju čine-C1-6alkil-Si(R5)3 (pri čemu R5 za svaku pojavu je C1-6alkil), pri čemu izraz alkil obuhvaća alkilne dijelove koje imaju supstituente koji zamjenjuju vodik na jednom ili više ugljika okosnice ugljikovodika, pri čemu takvi supstituenti su odabrani iz skupine koju čine hidroksil, karbonil, uključujući karboksil, alkoksikarbonil, formil, ili acil, tiokarbonil, uključujući tioester, tioacetat, ili tioformat, alkoksil, fosforil, fosfonat, fosfinat, fosfat, amino, amido, amidin, imin, cijano, nitro, azido, sulfhidril, alkiltio, sulfat, sulfonat, sulfamoil, sulfonamido, sulfonil, heterociklil, aralkil, ili aromatski ili heteroaromatski dio, i
pri čemu Pg je poželjno -(CH2)2-Si(CH3)3.
14. Postupak prema patentnom zahtjevu 13, naznačen time što je formula IV slobodna baza.
15. Postupak prema bilo kojem od patentnih zahtjeva 13-14, naznačen time što postupak nadalje obuhvaća dovođenje u kontakt formule IV s bazom, pri čemu se dovođenje u kontakt spoja s formulom III sa spojem s formulom IV poželjno odvija u otapalu.
16. Spoj predstavljen s:
naznačen time što:
Pg je -C1-6alkil-Si(R5)3; i
R5 svaki puta je C1-6alkil, pri čemu Pg je poželjno -(CH2)2-Si(CH3)3 i pri čemu izraz alkil obuhvaća alkilne dijelove koje imaju supstituente koji zamjenjuju vodik na jednom ili više ugljika okosnice ugljikovodika, pri čemu su takvi supstituenti odabrani iz skupine koju čine hidroksil, karbonil, uključujući karboksil, alkoksikarbonil, formil, ili acil, tiokarbonil, uključujući tioester, tioacetat, ili tioformat, alkoksil, fosforil, fosfonat, fosfinat, fosfat, amino, amido, amidin, imin, cijano, nitro, azido, sulfhidril, alkiltio, sulfat, sulfonat, sulfamoil, sulfonamido, sulfonil, heterociklil, aralkil, ili aromatski ili heteroaromatski dio.
17. Postupak za pripremanje spoja predstavljenog s formulom II prema zahtjevu 16, naznačen time što sadrži:
dovođenje u kontakt spoja
sa spojem predstavljenim s:
pod uvjetima prikladnim za pripravu spoja iz zahtjeva 16.
18. Postupak za pripremanje spoja predstavljenog s:
pri čemu,
R1 i R2 su svaki neovisno odabrani iz skupine koja sadrži vodik, alkalijski metal, NH4+, NH3+-(R3), NH2+-(R3)2, i NH+-(R3)3, ili R1 i R2 uzeti zajedno su zemnoalkalijski metal;
R3 je neovisno odabran za svaku pojavu iz skupine koja sadrži C1-6alkil-, hidroksiC1-6alkil-, fenil i benzil,
i pri čemu izraz alkil obuhvaća alkilne dijelove koje imaju supstituente koji zamjenjuju vodik na jednom ili više ugljika okosnice ugljikovodika, pri čemu su takvi supstituenti odabrani iz skupine koju čine hidroksil, karbonil, uključujući karboksil, alkoksikarbonil, formil, ili acil, tiokarbonil, uključujući tioester, tioacetat, ili tioformat, alkoksil, fosforil, fosfonat, fosfinat, fosfat, amino, amido, amidin, imin, cijano, nitro, azido, sulfhidril, alkiltio, sulfat, sulfonat, sulfamoil, sulfonamido, sulfonil, heterociklil, aralkil, ili aromatski ili heteroaromatski dio;
koji sadrži dovođenje u kontakt Bronstedove kiseline, poželjno trifluorooctene kiseline, i spoja formule II pripravljenog kao u zahtjevu 13 ili 17.
19. Spoj naznačen time što je predstavljen s:
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EP13806968.7A EP2861608B8 (en) | 2012-06-19 | 2013-06-19 | Prodrug derivatives of (e)-n-methyl-n-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
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2016
- 2016-11-22 JP JP2016226856A patent/JP2017105758A/ja active Pending
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2019
- 2019-05-29 HR HRP20190980TT patent/HRP20190980T1/hr unknown
- 2019-06-19 CY CY20191100629T patent/CY1122006T1/el unknown
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