HRP20200741T1 - Ciklički derivati estera boronske kiseline, postupak njihove proizvodnje i njihove terapeutske uporabe - Google Patents
Ciklički derivati estera boronske kiseline, postupak njihove proizvodnje i njihove terapeutske uporabe Download PDFInfo
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- HRP20200741T1 HRP20200741T1 HRP20200741TT HRP20200741T HRP20200741T1 HR P20200741 T1 HRP20200741 T1 HR P20200741T1 HR P20200741T T HRP20200741T T HR P20200741TT HR P20200741 T HRP20200741 T HR P20200741T HR P20200741 T1 HRP20200741 T1 HR P20200741T1
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- carbocyclyl
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- -1 Cyclic boronic acid ester Chemical class 0.000 title claims 37
- 238000000034 method Methods 0.000 title claims 18
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000001072 heteroaryl group Chemical group 0.000 claims 27
- 125000004452 carbocyclyl group Chemical group 0.000 claims 20
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 13
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 10
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000004423 acyloxy group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003368 amide group Chemical group 0.000 claims 6
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims 6
- 238000011905 homologation Methods 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 238000007363 ring formation reaction Methods 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 150000003952 β-lactams Chemical class 0.000 claims 4
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical class COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 3
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 3
- 101100439665 Arabidopsis thaliana SWI2 gene Proteins 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- JUZNIMUFDBIJCM-ANEDZVCMSA-N Invanz Chemical compound O=C([C@H]1NC[C@H](C1)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)NC1=CC=CC(C(O)=O)=C1 JUZNIMUFDBIJCM-ANEDZVCMSA-N 0.000 claims 3
- TYMABNNERDVXID-DLYFRVTGSA-N Panipenem Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1S[C@H]1CCN(C(C)=N)C1 TYMABNNERDVXID-DLYFRVTGSA-N 0.000 claims 3
- 229910006069 SO3H Inorganic materials 0.000 claims 3
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 229960003169 biapenem Drugs 0.000 claims 3
- MRMBZHPJVKCOMA-YJFSRANCSA-N biapenem Chemical compound C1N2C=NC=[N+]2CC1SC([C@@H]1C)=C(C([O-])=O)N2[C@H]1[C@@H]([C@H](O)C)C2=O MRMBZHPJVKCOMA-YJFSRANCSA-N 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 229960000484 ceftazidime Drugs 0.000 claims 3
- ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 238000006073 displacement reaction Methods 0.000 claims 3
- 229960000895 doripenem Drugs 0.000 claims 3
- AVAACINZEOAHHE-VFZPANTDSA-N doripenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](CNS(N)(=O)=O)C1 AVAACINZEOAHHE-VFZPANTDSA-N 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229960002770 ertapenem Drugs 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 claims 3
- 229960002182 imipenem Drugs 0.000 claims 3
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims 3
- 229960002260 meropenem Drugs 0.000 claims 3
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229950011346 panipenem Drugs 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- YWKJNRNSJKEFMK-PQFQYKRASA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCCC=4C=CC=3)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 YWKJNRNSJKEFMK-PQFQYKRASA-N 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 229950009592 cefquinome Drugs 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 238000005809 transesterification reaction Methods 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- MOILFCKRQFQVFS-BDNRQGISSA-N (1r,3s,4r,5r)-4,6,6-trimethylbicyclo[3.1.1]heptane-3,4-diol Chemical compound C1[C@@H]2C(C)(C)[C@H]1C[C@H](O)[C@@]2(O)C MOILFCKRQFQVFS-BDNRQGISSA-N 0.000 claims 1
- UUGRTBCTVUNWTN-DLRIENLKSA-N (2s,3s)-3-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-2-methyl-4-oxoazetidine-1-sulfonic acid Chemical compound O=C1N(S(O)(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(\C=1N=C(N)SC=1)=N/OCC1=CC(=O)C(O)=CN1O UUGRTBCTVUNWTN-DLRIENLKSA-N 0.000 claims 1
- KEDAXBWZURNCHS-GPODMPQUSA-N (4r,5s,6s)-3-[(3s,5s)-5-[(3s)-3-[[2-(diaminomethylideneamino)acetyl]amino]pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound O=C([C@@H]1C[C@@H](CN1C)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)N1CC[C@H](NC(=O)CN=C(N)N)C1 KEDAXBWZURNCHS-GPODMPQUSA-N 0.000 claims 1
- LZKPUSJSJVEXAW-WDXSGGTDSA-N (4s,5r,6s)-3-[7-[1-(2-amino-2-oxoethyl)pyridin-1-ium-3-carbonyl]imidazo[5,1-b][1,3]thiazol-2-yl]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C([O-])=O)=O)[C@H](O)C)C(SC1=2)=CN1C=NC=2C(=O)C1=CC=C[N+](CC(N)=O)=C1 LZKPUSJSJVEXAW-WDXSGGTDSA-N 0.000 claims 1
- FMZXNVLFJHCSAF-DNVCBOLYSA-N (6R,7R)-3-[(4-carbamoyl-1-pyridin-1-iumyl)methyl]-8-oxo-7-[(1-oxo-2-thiophen-2-ylethyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC(C(=O)N)=CC=[N+]1CC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CC=3SC=CC=3)[C@H]2SC1 FMZXNVLFJHCSAF-DNVCBOLYSA-N 0.000 claims 1
- SCSMAWFISUMSTO-ZTJYIHJESA-N (6R,7R)-3-[2-(2-aminoethylsulfanylmethyl)pyridin-3-yl]sulfanyl-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC1=NC(=NS1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)SC=2C(=NC=CC=2)CSCCN)C(=O)O)C1=O)=N/O SCSMAWFISUMSTO-ZTJYIHJESA-N 0.000 claims 1
- XSPUSVIQHBDITA-KXDGEKGBSA-N (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1CN1N=NC(C)=N1 XSPUSVIQHBDITA-KXDGEKGBSA-N 0.000 claims 1
- WDLWHQDACQUCJR-ZAMMOSSLSA-N (6r,7r)-7-[[(2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(e)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)/C=C/C)C(O)=O)=CC=C(O)C=C1 WDLWHQDACQUCJR-ZAMMOSSLSA-N 0.000 claims 1
- LTUWUNMGTLOPNC-RLQAYIIJSA-N (6r,7r)-7-[[(2z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-[3-(2-aminoethylsulfanylmethyl)pyridin-4-yl]sulfanyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NCCSCC1=CN=CC=C1SC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)C(=N/O)\C3=C(SC(N)=N3)Cl)[C@H]2SC1 LTUWUNMGTLOPNC-RLQAYIIJSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- UJDQGRLTPBVSFN-TVNHLQOTSA-N 2-[(z)-[2-[[(6r,7r)-3-[[3-amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl]methyl]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]amino]-1-(5-amino-1,2,4-thiadiazol-3-yl)-2-oxoethylidene]amino]oxy-2-methylpropanoate;sulfuric acid Chemical compound OS(O)(=O)=O.CN1C(N)=C(NC(=O)NCCN)C=[N+]1CC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)C(=N/OC(C)(C)C([O-])=O)\C=3N=C(N)SN=3)[C@H]2SC1 UJDQGRLTPBVSFN-TVNHLQOTSA-N 0.000 claims 1
- HGGAKXAHAYOLDJ-FHZUQPTBSA-N 6alpha-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid Chemical compound S([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1[C@H]1CCCO1 HGGAKXAHAYOLDJ-FHZUQPTBSA-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
- 229910015845 BBr3 Inorganic materials 0.000 claims 1
- 229910015844 BCl3 Inorganic materials 0.000 claims 1
- UQLLWWBDSUHNEB-CZUORRHYSA-N Cefaprin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CSC1=CC=NC=C1 UQLLWWBDSUHNEB-CZUORRHYSA-N 0.000 claims 1
- QYQDKDWGWDOFFU-IUODEOHRSA-N Cefotiam Chemical compound CN(C)CCN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC=3N=C(N)SC=3)[C@H]2SC1 QYQDKDWGWDOFFU-IUODEOHRSA-N 0.000 claims 1
- GNWUOVJNSFPWDD-XMZRARIVSA-M Cefoxitin sodium Chemical compound [Na+].N([C@]1(OC)C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)CC1=CC=CS1 GNWUOVJNSFPWDD-XMZRARIVSA-M 0.000 claims 1
- JWCSIUVGFCSJCK-CAVRMKNVSA-N Disodium Moxalactam Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CO[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C1=CC=C(O)C=C1 JWCSIUVGFCSJCK-CAVRMKNVSA-N 0.000 claims 1
- 238000006219 Matteson homologation reaction Methods 0.000 claims 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 1
- KLFSEZJCLYBFKQ-WXYNYTDUSA-N [(3s)-3-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-2,2-dimethyl-4-oxoazetidin-1-yl] hydrogen sulfate Chemical compound O=C1N(OS(O)(=O)=O)C(C)(C)[C@@H]1NC(=O)C(\C=1N=C(N)SC=1)=N/OCC1=CC(=O)C(O)=CN1O KLFSEZJCLYBFKQ-WXYNYTDUSA-N 0.000 claims 1
- 150000001412 amines Chemical class 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
- 229960000723 ampicillin Drugs 0.000 claims 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin 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=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000000043 antiallergic agent Substances 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 claims 1
- 239000003429 antifungal agent Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 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
- 229960003644 aztreonam Drugs 0.000 claims 1
- 229960002699 bacampicillin Drugs 0.000 claims 1
- PFOLLRNADZZWEX-FFGRCDKISA-N bacampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OC(C)OC(=O)OCC)=CC=CC=C1 PFOLLRNADZZWEX-FFGRCDKISA-N 0.000 claims 1
- 229960003669 carbenicillin Drugs 0.000 claims 1
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 claims 1
- 229960000717 carindacillin Drugs 0.000 claims 1
- JIRBAUWICKGBFE-MNRDOXJOSA-N carindacillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(=O)OC=1C=C2CCCC2=CC=1)C1=CC=CC=C1 JIRBAUWICKGBFE-MNRDOXJOSA-N 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- RRYMAQUWDLIUPV-BXKDBHETSA-N cefacetrile Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC#N)[C@@H]12 RRYMAQUWDLIUPV-BXKDBHETSA-N 0.000 claims 1
- 229960005361 cefaclor Drugs 0.000 claims 1
- QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 claims 1
- 229960004841 cefadroxil Drugs 0.000 claims 1
- NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 claims 1
- FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 claims 1
- 229950004030 cefaloglycin Drugs 0.000 claims 1
- 229960003866 cefaloridine Drugs 0.000 claims 1
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 claims 1
- 229960000603 cefalotin Drugs 0.000 claims 1
- 229960003012 cefamandole Drugs 0.000 claims 1
- OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 claims 1
- 229960004350 cefapirin Drugs 0.000 claims 1
- 229960002420 cefatrizine Drugs 0.000 claims 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 claims 1
- HGXLJRWXCXSEJO-GMSGAONNSA-N cefazaflur Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CSC(F)(F)F)[C@H]2SC1 HGXLJRWXCXSEJO-GMSGAONNSA-N 0.000 claims 1
- 229950004359 cefazaflur Drugs 0.000 claims 1
- 229960005312 cefazedone Drugs 0.000 claims 1
- VTLCNEGVSVJLDN-MLGOLLRUSA-N cefazedone Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3C=C(Cl)C(=O)C(Cl)=C3)[C@H]2SC1 VTLCNEGVSVJLDN-MLGOLLRUSA-N 0.000 claims 1
- 229960001139 cefazolin Drugs 0.000 claims 1
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- HOGISBSFFHDTRM-GHXIOONMSA-N cefdaloxime Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(O)=O)C(=O)C(=N/O)\C1=CSC(N)=N1 HOGISBSFFHDTRM-GHXIOONMSA-N 0.000 claims 1
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- RTXOFQZKPXMALH-GHXIOONMSA-N cefdinir Chemical compound S1C(N)=NC(C(=N\O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 RTXOFQZKPXMALH-GHXIOONMSA-N 0.000 claims 1
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- LNZMRLHZGOBKAN-KAWPREARSA-N cefpimizole Chemical compound N1=CNC(C(=O)N[C@@H](C(=O)N[C@@H]2C(N3C(=C(C[N+]=4C=CC(CCS(O)(=O)=O)=CC=4)CS[C@@H]32)C([O-])=O)=O)C=2C=CC=CC=2)=C1C(=O)O LNZMRLHZGOBKAN-KAWPREARSA-N 0.000 claims 1
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- 229960005090 cefpodoxime Drugs 0.000 claims 1
- WYUSVOMTXWRGEK-HBWVYFAYSA-N cefpodoxime Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(O)=O)C(=O)C(=N/OC)\C1=CSC(N)=N1 WYUSVOMTXWRGEK-HBWVYFAYSA-N 0.000 claims 1
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- RDMOROXKXONCAL-UEKVPHQBSA-N cefroxadine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)OC)C(O)=O)=CCC=CC1 RDMOROXKXONCAL-UEKVPHQBSA-N 0.000 claims 1
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- NNULBSISHYWZJU-LLKWHZGFSA-N ceftizoxime Chemical compound N([C@@H]1C(N2C(=CCS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 NNULBSISHYWZJU-LLKWHZGFSA-N 0.000 claims 1
- VOAZJEPQLGBXGO-SDAWRPRTSA-N ceftobiprole Chemical compound S1C(N)=NC(C(=N\O)\C(=O)N[C@@H]2C(N3C(=C(\C=C/4C(N([C@H]5CNCC5)CC\4)=O)CS[C@@H]32)C(O)=O)=O)=N1 VOAZJEPQLGBXGO-SDAWRPRTSA-N 0.000 claims 1
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- 229960004755 ceftriaxone Drugs 0.000 claims 1
- VAAUVRVFOQPIGI-SPQHTLEESA-N ceftriaxone Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C(=O)NN1C VAAUVRVFOQPIGI-SPQHTLEESA-N 0.000 claims 1
- 229960001668 cefuroxime Drugs 0.000 claims 1
- JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 claims 1
- CXHKZHZLDMQGFF-ZSDSSEDPSA-N cefuzonam Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=CN=NS1 CXHKZHZLDMQGFF-ZSDSSEDPSA-N 0.000 claims 1
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- 229940106164 cephalexin Drugs 0.000 claims 1
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 claims 1
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 claims 1
- RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 229960002457 epicillin Drugs 0.000 claims 1
- RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 claims 1
- 229960000379 faropenem Drugs 0.000 claims 1
- 229960002878 flomoxef Drugs 0.000 claims 1
- UHRBTBZOWWGKMK-DOMZBBRYSA-N flomoxef Chemical compound O([C@@H]1[C@@](C(N1C=1C(O)=O)=O)(NC(=O)CSC(F)F)OC)CC=1CSC1=NN=NN1CCO UHRBTBZOWWGKMK-DOMZBBRYSA-N 0.000 claims 1
- 229960003884 hetacillin Drugs 0.000 claims 1
- DXVUYOAEDJXBPY-NFFDBFGFSA-N hetacillin Chemical compound C1([C@@H]2C(=O)N(C(N2)(C)C)[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 DXVUYOAEDJXBPY-NFFDBFGFSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- 229960000433 latamoxef Drugs 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229960001977 loracarbef Drugs 0.000 claims 1
- JAPHQRWPEGVNBT-UTUOFQBUSA-N loracarbef Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CC[C@@H]32)C([O-])=O)=O)[NH3+])=CC=CC=C1 JAPHQRWPEGVNBT-UTUOFQBUSA-N 0.000 claims 1
- 229960003806 metampicillin Drugs 0.000 claims 1
- FZECHKJQHUVANE-MCYUEQNJSA-N metampicillin Chemical compound C1([C@@H](N=C)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 FZECHKJQHUVANE-MCYUEQNJSA-N 0.000 claims 1
- 229960003085 meticillin Drugs 0.000 claims 1
- 229960000515 nafcillin Drugs 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
- 125000002734 organomagnesium group Chemical group 0.000 claims 1
- 229960001019 oxacillin Drugs 0.000 claims 1
- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 claims 1
- 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
- 229960003342 pivampicillin Drugs 0.000 claims 1
- ZEMIJUDPLILVNQ-ZXFNITATSA-N pivampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OCOC(=O)C(C)(C)C)=CC=CC=C1 ZEMIJUDPLILVNQ-ZXFNITATSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- XFGOMLIRJYURLQ-GOKYHWASSA-N razupenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)SC(SC=1)=NC=1C1=C[C@H](C)NC1 XFGOMLIRJYURLQ-GOKYHWASSA-N 0.000 claims 1
- 229950000381 razupenem Drugs 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 229960002780 talampicillin Drugs 0.000 claims 1
- SOROUYSPFADXSN-SUWVAFIASA-N talampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)OC2C3=CC=CC=C3C(=O)O2)(C)C)=CC=CC=C1 SOROUYSPFADXSN-SUWVAFIASA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 229960004659 ticarcillin Drugs 0.000 claims 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims 1
- VAMSVIZLXJOLHZ-QWFSEIHXSA-N tigemonam Chemical compound O=C1N(OS(O)(=O)=O)C(C)(C)[C@@H]1NC(=O)C(=N/OCC(O)=O)\C1=CSC(N)=N1 VAMSVIZLXJOLHZ-QWFSEIHXSA-N 0.000 claims 1
- 229950010206 tigemonam Drugs 0.000 claims 1
- 229950003816 tomopenem Drugs 0.000 claims 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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Claims (23)
1. Postupak proizvodnje spoja formule (I):
[image]
ili njegove farmaceutski prihvatljive soli, naznačen time, da
Y je C2-4alkilen povezivač ili C2-4alkenilen povezivač;
R1 je odabran iz skupine koju čine sljedeći: -C1-9alkil, -C2-9alkenil, -C2-9alkinil, -NR9R!0, -C1-9alkilR11, -C2-9alkenilR11, -C2-9alkinilR11, -karbociklil-R11, -CH(OH)C1-9alkilR9, -CH(OH)C2-9alkenilR9, -CH(OH)C2-9alkinilR9, -CH(OH)karbociklil-R9, -C(=O)R9, -C(=O)C1-9alkilR9, -C(=O)C2-9alkenilR9, -C(=O)C2-9alkinilR9, -C(=O)C2-9karbociklil-R9, -C(=O)NR9R10, -N(R9)C(=O)R9, -N(R9)C(=O)NR9R10, -N(R9)C(=O)OR9, -N(R9)C(=O)C(=NRI0)R9, -N(R9)C(=O)C(=CR9R10)R9, -N(R9)C(=O)C1-4alkilN(R9)C(=O)R9, -N(R9)C(=NR10)R9, -C(=NR10)NR9R10, -N=C(R9)NR9R10, -N(R9)SO2R9, -N(R9)SO2NR9R10, -N=CHR9, aril, heteroaril, karbociklil i heterociklil;
R6 je H;
R7 je H,
R8 je H;
svaki R9 je neovisno odabran iz skupine koju čine sljedeći: H, -C1-9alkil, -C2-9alkenil, -C2-9alkinil, -C1-9alkilR11, -C2-9alkenilR11, -C2-9alkinilR11, -karbociklil-R11, aril, heteroaril, karbociklil i heterociklil;
svaki R10 je neovisno odabran iz skupine koju čine sljedeći: H, -C1-9alkil, -OR9, -CH(=NH), -C(=O)OR9, aril, heteroaril, karbociklil i heterociklil;
svaki R11 je neovisno odabran iz skupine koju čine sljedeći: aril, heteroaril, karbociklil i heterociklil;
X je odabran iz skupine koju čine sljedeći: -CO2R12, -P(O)(OR9)2, -P(O)(R9)(OR9), -P(O)(OR12')2, -P(O)(R9)(OR12'), -CON(R9)OH, SO3H, -SO2N(R9)OH, -CONHNHSO2R9, -COHNSO2R9, i izoster karboksilne kiseline odabran od 5-7-članog karbocikla ili heterocikla, pri čemu je 5-7-člani karbocikl ili heterocikl odabran iz skupine koja se sastoji od sljedećih:
[image]
i pritom je bilo koji atom iz prstenaste strukture od 5-7-članog karbocikla ili heterocikla, opcionalno supstituiran na jednoj ili više pozicija s R9;
R12' je odabran iz skupine koju čine sljedeći: H, R11, -C(R13)2OC(O)C1-9alkil, -C(R13)2OC(O)R11, -C(R13)2OC(O)OC1-9alkil i -C(R13)2OC(O)OR11;
R12 je odabran iz skupine koju čine sljedeći: H, C1-9alkil, -(CH2)0-3-R11, -C(R13)2OC(O)C1-9alkil, -C(R13)2OC(O)R11, -C(R13)2OC(O)OC1-9alkil i -C(R13)2OC(O)OR11;
svaki R13 je neovisno odabran iz skupine koju čine: H i –C1-4alkil; i
m je 1;
pri čemu je svaki -C1-9alkil, -C2-9alkenil i -C2-9alkinil, neovisno opcionalno supstituiran sa sljedećima: halogen, hidroksi, aciloksi, amino, amido, cijano, nitro, guanidino, amidino, merkapto, karboksi, sulfoniloksi, karbonil, benziloksi, aril, heteroaril, karbociklil, heterociklil;
gdje je svaki aril i heteroaril neovisno opcionalno supstituiran sa sljedećima: amino, cijano, hidroksi, -C1-9alkil, haloalkil, alkoksi, nitro, halogen, merkapto, karboksi, karbonil, benziloksi, aril ili heteroaril;
dok je svaki karbociklil i heterociklil neovisno opcionalno supstituiran sa sljedećima: halogen, alkoksi, aciloksi, amino, amido, cijano, nitro, hidroksi, merkapto, karboksi, karbonil, benziloksi, aril, heteroaril;
te time, da postupak obuhvaća sljedeće: uklanjanje zaštitne skupine i ciklizacija pinandiol estera boronske kiseline, u svrhu dobivanja spoja formule (I).
2. Postupak prema patentnom zahtjevu 1, naznačen time, da spoj formule (I) ima sljedeću strukturu:
[image]
R2 i R4 su H;
R3 i R5 su H,
R9 je odabran iz skupine koju čine sljedeći: -R9, -NR9R10, -OR9, -C(=NR10)R9, -C(=CR9R10)R9, -C1-4alkilN(R9)C(=O)R9, -C1-9alkilR11 i -C(=NOR9)R9';
R9 je odabran iz skupine koju čine sljedeći: -Ci.palkii, aril, heteroaril, karbociklil i heterociklil; i
R11 je aril ili heteroaril.
3. Postupak prema patentnom zahtjevu 2, naznačen time, da pinandiol ester boronske kiseline ima strukturu formule (XII):
[image]
te opcionalno pritom, uklanjanje zaštitne skupine i ciklizacija obuhvaćaju dovođenje u doticaj pinandiol estera boronske kiseline s reagensom koji je odabran iz skupine koju čine: HCl, BCl3, BBr3 i CF3COOH.
4. Postupak prema patentnom zahtjevu 3, naznačen time, da se pinandiol ester boronske kiseline dobiva putem koraka koji je odabran od spajanja bis- trimetilsilil (TMS)2 derivata amina s RaCOOH, ili reakcije bis-trimetilsilil (TMS)2 derivata amina s RaCOCl, pri čemu bis-trimetilsilil derivat amina ima strukturu formule (XI):
[image]
5. Postupak prema patentnom zahtjevu 4, naznačen time, da se bis- trimetilsilil (TMS)2 derivat amina dobiva pomoću premještanja kloro skupine od spoja formule (X):
[image]
te se opcionalno pritom, premještanje kloro skupine postiže u prisutnosti litijevog bis(trimetilsilil)amida.
6. Postupak prema patentnom zahtjevu 5, naznačen time, da se spoj formule (X) dobiva pomoću homologiranja spoja formule (IX):
[image]
te se opcionalno pritom, homologiranje postiže u prisutnosti diklorometana i n-butil-litija.
7. Postupak prema bilo kojem od patentnih zahtjeva 1 do 6, naznačen time, da spoj formule (I) ima sljedeću strukturu:
[image]
8. Postupak proizvodnje spoja formule (I) prema bilo kojem od prethodnih patentnih zahtjeva, pri čemu taj spoj ima sljedeću strukturu:
[image]
ili njegova farmaceutski prihvatljiva sol,
naznačen time, da postupak obuhvaća: uklanjanje zaštitne skupine i ciklizaciju pinandiol estrea boronske kiseline, u svrhu dobivanja spoja formule (I), gdje pinandiol ester boronske kiseline ima strukturu formule (XLII):
[image]
te se opcionalno pritom, uklanjanje zaštitne skupine i ciklizacija provode u prisutnosti 3N HCl i 1,4-dioksana.
9. Postupak prema patentnom zahtjevu 8, naznačen time, da se pinandiol ester boronske kiseline dobiva putem reakcije bis-trimetilsilil (TMS)2 derivata amina koji ima sljedeću strukturu:
[image]
sa spojem koji ima sljedeću strukturu:
[image]
gdje opcionalno, reakcija obuhvaća jedan korak koji se izvodi na -78°C u trajanju od 90 minuta, i jedan korak koji se izvodi na sobnoj temperaturi u trajanju od 90 minuta.
10. Postupak prema patentnom zahtjevu 9, naznačen time, da se bis- trimetilsilil (TMS)2 derivat amina dobiva pomoću premještanja kloro skupine iz spoja formule (XL):
[image]
te se opcionalno pritom, premještanje provodi u prisutnosti litijevog bis(trimetilsilil)amida (LiHMDS).
11. Postupak prema patentnom zahtjevu 10, naznačen time, da se spoj formule (XL) dobiva putem homologiranja spoja formule (XXXIX):
[image]
te se opcionalno pritom, homologiranje provodi u prisutnosti cinkovog klorida.
12. Postupak prema patentnom zahtjevu 1, naznačen time, da pinandiol ester boronske kiseline ima strukturu formule (XV):
[image]
u kojoj:
R2 i R4 su H;
R3 i R5 su H;
Rc je R1; i opcionalno,
gdje se pinandiol ester boronske kiseline dobiva putem premještanja bromo skupine iz bromo-spoja formule (XIV):
[image]
i opcionalno,
pritom se premještanje bromo skupine postiže uporabom sredstva koje je odabrano iz skupine koju čine: α-alkoksi supstituirani alkil-litijev agens, organomagnezijev reagens, natrijeva sol derivata alkila, i natrijeva sol derivata arilkarbamata.
13. Postupak prema patentnom zahtjevu 1, naznačen time, da pinandiol ester boronske kiseline ima strukturu formule (XXV):
[image]
u kojoj:
R2 i R4 su H;
R3 i R5 su H9;
Ra, Rb, Rc i Rd su H;
R' je hidroksilna zaštitna skupina;
R" je odabran iz skupine koju čine sljedeći: H, -C1-9alkil, -(CH2)0-3-R11, -C(R13)2OC(O)C1-9alkil, -C(R13)2OC(O)R11, -C(R13)2OC(O)OC1-9alkil i -C(R13)2OC(O)OR11;
svaki R13 je neovisno odabran iz skupine koju čine sljedeći: H i –C1-4alkil;
p i q su odabrani od 0, 1 ili 2, tako da zbroj od p i q bude 1 ili 2; te opcionalno, pritom se pinandiol ester boronske kiseline dobiva putem Mattesonovog homologiranja formule (XXIV):
[image]
14. Postupak prema patentnom zahtjevu 1 ili 2, naznačen time, da pinandiol ester boronske kiseline ima strukturu formule (XXXIV):
[image]
u kojoj:
R2 i R4 su H;
R3 i R5 su H;
Ra je odabran iz skupine koju čine sljedeći: -R9, -NR9R10, -OR9, -C(=NR10)R9, -C(=CR9R10)R9, -C1-4 alkilN(R9)C(=O)R9, -C1-9 alkilR11 i -C(=NOR9)R9';
R9 je odabran iz skupine koju čine sljedeći: -C1-9alkil, aril, heteroaril, karbociklil i heterociklil;
te opcionalno,
pritom se pinandiol ester boronske kiseline dobiva putem trans-esterifikacije pinakol boronata formule (XXXIII):
[image]
te opcionalno,
pritom se trans-esterifikacija postiže putem reakcije pinakol boronata s pinandiolom u prisutnosti tetrahidrofurana; te opcionalno,
pritom se pinakol boronat dobiva uporabom iridijeve katalize s tert- butildimetilsilil spoja formule (XXXII):
[image]
15. Spoj, naznačen time, da je to spoj formule (I):
[image]
ili njegova farmaceutski prihvatljiva sol,
gdje:
Y je C2-4alkilen povezivač ili C2-4alkenilen povezivač;
R1 je odabran iz skupine koju čine sljedeći: -C1-9alkil, -C2-9alkenil, -C2-9alkinil, -NR9R10, -C1-9alkilR11, -C2-9alkenilRn, -C2-9alkinilR11, -karbociklil-R11, -CH(OH)C1-9alkilR9, -CH(OH)C2-9alkenilR9, -CH(OH)C2-9alkinilR9, -CH(OH)karbociklil-R9, -C(=O)R9, -C(=O)C1-9alkilR9, -C(=O)C2-9alkenilR9, -C(=O)C2-9alkinilR9, -C(=O)C2-9karbociklil-R9, -C(=O)NR9R10, -N(R9)C(=O)R9, -N(R9)C(=O)NR9R10, -N(R9)C(=O)OR9, -N(R9)C(=O)C(=NR10)R9, -N(R9)C(=O)C(=CR9R10)R9, -N(R9)C(=O)C1-4alkilN(R9)C(=O)R9, -N(R9)C(=NR10)R9, -C(=NR10)NR9R10, -N=C(R9)NR9R10, -N(R9)SO2R9, -N(R9)SO2NR9R10, -N=CHR9, aril, heteroaril, karbociklil i heterociklil;
R6 je H;
R7 je H,
R8 je H;
svaki R9 je neovisno odabran iz skupine koju čine sljedeći: H, -C1-9alkil, -C2-9alkenil, -C2-9alkinil, -C1-9alkilR11, -C2-9alkenilR11, -C2-9alkinilR11, -karbociklil-R11, aril, heteroaril, karbociklil i heterociklil;
svaki R10 je neovisno odabran iz skupine koju čine sljedeći: H, -C1-9alkil, -OR9, -CH(=NH), -C(=O)OR9, aril, heteroaril, karbociklil i heterociklil;
svaki R11 je neovisno odabran iz skupine koju čine sljedeći: aril, heteroaril, karbociklil i heterociklil;
X je odabran iz skupine koju čine sljedeći: -CO2R12, -P(O)(OR9)2, -P(O)(R9)(OR9), -P(O)(OR12')2, -P(O)(R9)(OR12'), -CON(R9)OH, -SO3H, -SO2N(R9)OH, -CONHNHSO2R9, -COHNSO2R9, i izoster karboksilne kiseline odabran od 5-7-članog karbocikla ili heterocikla, pri čemu je 5-7-člani karbocikl ili heterocikl odabran iz skupine koja se sastoji od sljedećih:
[image]
[image]
te je pritom bilo koji atom iz prstenaste strukture od 5-7-članog karbocikla ili heterocikla, opcionalno supstituiran na jednoj ili više pozicija s R9;
R12' je odabran iz skupine koju čine sljedeći: H, R11, -C(R13)2OC(O)C1-9alkil, -C(R13)2OC(O)R11, -C(R13)2OC(O)OC1-9alkil i -C(R13)2OC(O)OR11;
R12 je odabran iz skupine koju čine sljedeći: H, C1-9alkil, -(CH2)0-3-R11, -C(R13)2OC(O)C1-9alkil, -C(R13)2OC(O)R11, -C(R13)2OC(O)OC1-9alkil i -C(R13)2OC(O)OR11;
svaki R13 je neovisno odabran iz skupine koju čine: H i -C1-4alkil; i
m je 1;
pri čemu je svaki –C1-9alkii, -C2-9alkenil i -C2-9alkinil, neovisno opcionalno supstituiran sa sljedećima: halogen, hidroksi, aciloksi, amino, amido, cijano, nitro, guanidino, amidino, merkapto, karboksi, sulfoniloksi, karbonil, benziloksi, aril, heteroaril, karbociklil, heterociklil;
gdje je svaki aril i heteroaril neovisno opcionalno supstituiran sa sljedećima: amino, cijano, hidroksi, -C1-9alkil, haloalkil, alkoksi, nitro, halogen, merkapto, karboksi, karbonil, benziloksi, aril ili heteroaril;
dok je svaki karbociklil i heterociklil neovisno opcionalno supstituiran sa sljedećima: halogen, alkoksi, aciloksi, amino, amido, cijano, nitro, hidroksi, merkapto, karboksi, karbonil, benziloksi, aril, heteroaril;
te time, da se on upotrebljava u postupku liječenja i prevencije bakterijske infekcije.
16. Spoj formule (I):
[image]
ili njegova farmaceutski prihvatljiva sol,
gdje:
Y je C2-4alkilen povezivač ili C2-4alkenilen povezivač;
R1 je odabran iz skupine koju čine sljedeći: -C1-9alkil, -C2-9alkenil, -C2-9alkinil, -NR9R10, -C1-9alkilR11, -C2-9alkenilR11, -C2-9alkinilR11, -karbociklil-R11, -CH(OH)C1-9alkilR9, -CH(OH)C2-9alkenilR9, -CH(OH)C2-9alkinilR9, -CH(OH)karbociklil-R9, -C(=O)R9, -C(=O)C1-9alkilR9, -C(=O)C2-9alkenilR9, -C(-O)C2-9alkinilR9, -C(=O)C2-9karbociklil-R9, -C(=O)NR9R10, -N(R9)C(=O)R9, -N(R9)C(=O)NR9R10, -N(R9)C(=O)OR9, -N(R9)C(=O)C(=NR10)R9, -N(R9)C(=O)C(=CR9R10)R9, -N(R9)C(=O)C1-4alkilN(R9)C(=O)R9, -N(R9)C(=NR10)R9, -C(=NR10)NR9R10, -N=C(R9)NR9R10, -N(R9)SO2R9, -N(R9)SO2NR9R10, -N=CHR9, aril, heteroaril, karbociklil i heterociklil;
R6 je H;
R7 je H,
R8 je H;
svaki R9 je neovisno odabran iz skupine koju čine sljedeći: H, -C1-9alkil, -C2-9alkenil, -C2-9alkinil, -C1-9alkilR11, -C2-9alkenilR11, -C2-9alkinilR11, -karbociklil-R11, aril, heteroaril, karbociklil i heterociklil;
svaki R10 je neovisno odabran iz skupine koju čine sljedeći: H, -C1-9alkil, -OR9, -CH(=NH), -C(=O)OR9, aril, heteroaril, karbociklil i heterociklil;
svaki R11 je neovisno odabran iz skupine koju čine sljedeći: aril, heteroaril, karbociklil i heterociklil;
X je odabran iz skupine koju čine sljedeći: -CO2R12, -P(O)(OR9)2, -P(O)(R9)(OR9), -P(O)(OR12')2, -P(O)(R9)(OR12'), -CON(R9)OH, -SO3H, -SO2N(R9)OH, -CONHNHSO2R9, -COHNSO2R9, i izoster karboksilne kiseline odabran od 5-7-članog karbocikla ili heterocikla, pri čemu je 5-7-člani karbocikl ili heterocikl odabran iz skupine koja se sastoji od sljedećih:
[image]
te je pritom bilo koji atom iz prstenaste strukture od 5-7-članog karbocikla ili heterocikla, opcionalno supstituiran na jednoj ili više pozicija s R9;
R12' je odabran iz skupine koju čine sljedeći: H, R11, -C(R13)2OC(O)C1-9alkil, -C(R13)2OC(O)R11, -C(R13)2OC(O)OC1-9alkil i -C(R13)2OC(O)OR11;
R12 je odabran iz skupine koju čine sljedeći: H, C1-9alkil, -(CH2)0-3-R11, -C(R13)2OC(O)C1-9alkil, -C(R13)2OC(O)R11, -C(R13)2OC(O)OC1-9alkil i -C(R13)2OC(O)OR11;
svaki Ri3 je neovisno odabran iz skupine koju čine: H i –C1-4alkil; i
m je 1;
pri čemu je svaki -C1-9alkil, -C2-9alkenil i -C2-9alkinil, neovisno opcionalno supstituiran sa sljedećima: halogen, hidroksi, aciloksi, amino, amido, cijano, nitro, guanidino, amidino, merkapto, karboksi, sulfoniloksi, karbonil, benziloksi, aril, heteroaril, karbociklil, heterociklil;
gdje je svaki aril i heteroaril neovisno opcionalno supstituiran sa sljedećima: amino, cijano, hidroksi, -C1-9alkil, haloalkil, alkoksi, nitro, halogen, merkapto, karboksi, karbonil, benziloksi, aril ili heteroaril;
dok je svaki karbociklil i heterociklil neovisno opcionalno supstituiran sa sljedećima: halogen, alkoksi, aciloksi, amino, amido, cijano, nitro, hidroksi, merkapto, karboksi, karbonil, benziloksi, aril, heteroaril;
naznačen time, da se on upotrebljava u kombinaciji s dodatnim lijekom u postupku liječenja ili prevencije bakterijske infekcije.
17. Spoj za uporabu u skladu s patentnim zahtjevom 16, naznačen time, da je dodatni lijek odabran iz skupine koja se sastoji od sljedećih: antibakterijsko sredstvo, protugljivično sredstvo, protuvirusno sredstvo, protuupalno sredstvo, antialergijsko sredstvo.
18. Spoj za uporabu u skladu s patentnim zahtjevom 17, naznačen time, da dodatni lijek je β-laktam antibakterijsko sredstvo.
19. Spoj za uporabu u skladu s patentnim zahtjevom 18, naznačen time, da je β-laktam odabran iz skupine koja se sastoji od sljedećih: amoksicilin, ampicilin, pivampicilin, hetacilin, bakampicilin, metampicilin, talampicilin, epicilin, karbenicilin, karindacilin, tikarcilin, temocilin, azlocilin, piperacilin, mezlocilin, mecilinam, pivmecilinam, sulbenicilin, benzilpenicilin (G), klometocilin, benzatin benzilpenicilin, prokain benzilpenicilin, azidocilin, penamecilin, fenoksimetilpenicilin (V), propicilin, benzatin fenoksimetilpenicilin, feneticilin, kloksacilin, dikloksacilin, flukloksacilin, oksacilin, meticilin, nafcilin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cefacetril, cefadroksil, cefaleksin, cefaloglicin, cefalonium, cefaloridin, cefalotin, cefapirin, cefatrizin, cefazedon, cefazaflur, cefradin, cefroksadin, ceftezol, cefaklor, cefamandol, cefminoks, cefonicid, ceforanid, cefotiam, cefprozil, cefbuperazon, cefuroksim, cefuzonam, cefoksitin, cefotetan, cefmetazol, lorakarbef, cefiksim, ceftazidim, ceftriakson, cefcapen, cefdaloksim, cefdinir, cefditoren, cefetamet, cefmenoksim, cefodizim, cefoperazon, cefotaksim, cefpimizol, cefpiramid, cefpodoksim, cefsulodin, cefteram, ceftibuten, ceftiolen, ceftizoksim, flomoksef, latamoksef, cefepim, cefozopran, cefpirom, cefkvinom, ceftobiprol, ceftarolin, CXA-101, RWJ-54428, MC-04, 546, ME1036, BAL30072, SYN 2416, ceftiofur, cefkvinom, cefovecin, aztreonam, tigemonam, carumonam, RWJ-442831, RWJ-333441, i RWJ- 333442.
20. Spoj za uporabu u skladu s patentnim zahtjevom 19, naznačen time, da je β-laktam odabran iz skupine koju čine sljedeći: ceftazidim, biapenem, doripenem, ertapenem, imipenem, meropenem i panipenem.
21. Spoj za uporabu u skladu s bilo kojim od patentnih zahtjeva 15-16, naznačen time, da spoj formule (I) ima sljedeću strukturu:
[image]
22. Spoj za uporabu u skladu s patentnim zahtjevom 19, naznačen time, da β-laktam je meropenem i spoj formule (I) ima sljedeću strukturu:
[image]
23. Spoj za uporabu u skladu s patentnim zahtjevom 20, naznačen time, da je β-laktam odabran iz skupine koju čine sljedeći: ceftazidim, biapenem, doripenem, ertapenem, imipenem i panipenem, i pritom spoj formule (I) ima sljedeću strukturu:
[image]
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