AP832A - 3-Tetrahydrofuran and tetrohydropyrinol ephynolsporens and analogues. - Google Patents
3-Tetrahydrofuran and tetrohydropyrinol ephynolsporens and analogues. Download PDFInfo
- Publication number
- AP832A AP832A APAP/P/1991/000305A AP9100305A AP832A AP 832 A AP832 A AP 832A AP 9100305 A AP9100305 A AP 9100305A AP 832 A AP832 A AP 832A
- Authority
- AP
- ARIPO
- Prior art keywords
- carboxylate
- tetrahydrofuran
- ceph
- compound
- aminothiazol
- Prior art date
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title description 35
- -1 formamido Chemical group 0.000 claims abstract description 69
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 150
- 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 description 32
- 229910052708 sodium Inorganic materials 0.000 claims description 32
- 239000011734 sodium Substances 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 31
- 150000002148 esters Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- 238000001727 in vivo Methods 0.000 claims description 29
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 238000005917 acylation reaction Methods 0.000 claims description 10
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 5
- 239000003781 beta lactamase inhibitor Substances 0.000 claims description 5
- 229940126813 beta-lactamase inhibitor Drugs 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000004292 cyclic ethers Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- MYJSNLKUTOLHSV-SVLLLCHKSA-N tert-butyl (6r,7r)-7-amino-8-oxo-3-(oxolan-2-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound O=C([C@@H](N)[C@H]1SC2)N1C(C(=O)OC(C)(C)C)=C2C1CCCO1 MYJSNLKUTOLHSV-SVLLLCHKSA-N 0.000 claims description 2
- MOMMCCDMOQXKGH-NZMWDFQUSA-N 1-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2S)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)[C@H]2OCCC2)C(=O)OC(C)OC(=O)OC(C)C)C1=O)=N/OC MOMMCCDMOQXKGH-NZMWDFQUSA-N 0.000 claims 1
- FMSUTPHWDFNQNO-MBVQEMHOSA-N 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2r)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@@H]1[C@@H](C(N1C=1C(=O)OCOC(=O)C(C)(C)C)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1[C@H]1CCCO1 FMSUTPHWDFNQNO-MBVQEMHOSA-N 0.000 claims 1
- FMSUTPHWDFNQNO-NBXBADPDSA-N 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2s)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@@H]1[C@@H](C(N1C=1C(=O)OCOC(=O)C(C)(C)C)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1[C@@H]1CCCO1 FMSUTPHWDFNQNO-NBXBADPDSA-N 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 14
- 239000001257 hydrogen Substances 0.000 abstract description 12
- 208000035143 Bacterial infection Diseases 0.000 abstract description 8
- 208000022362 bacterial infectious disease Diseases 0.000 abstract description 8
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 3
- 239000003782 beta lactam antibiotic agent Substances 0.000 abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 108
- 229940093499 ethyl acetate Drugs 0.000 description 84
- 235000019439 ethyl acetate Nutrition 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
- 239000000203 mixture Substances 0.000 description 72
- 239000000243 solution Substances 0.000 description 67
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- 238000001819 mass spectrum Methods 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 150000002500 ions Chemical class 0.000 description 41
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
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- 125000000217 alkyl group Chemical group 0.000 description 24
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- 239000000741 silica gel Substances 0.000 description 24
- 229910002027 silica gel Inorganic materials 0.000 description 24
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 238000003818 flash chromatography Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 16
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 16
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- 229940035024 thioglycerol Drugs 0.000 description 16
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
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- 235000017281 sodium acetate Nutrition 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- CWNPOQFCIIFQDM-UHFFFAOYSA-N 3-nitrobenzyl alcohol Chemical compound OCC1=CC=CC([N+]([O-])=O)=C1 CWNPOQFCIIFQDM-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 150000001780 cephalosporins Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
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- 229940124587 cephalosporin Drugs 0.000 description 9
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 9
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
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- 238000010626 work up procedure Methods 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
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- 239000007858 starting material Substances 0.000 description 6
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- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 5
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- QRIBXVGHDLFNNE-DQJGWHCYSA-M sodium;(6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(oxolan-2-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C1CCCO1 QRIBXVGHDLFNNE-DQJGWHCYSA-M 0.000 description 1
- QRIBXVGHDLFNNE-PEMQHITISA-M sodium;(6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2r)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1[C@H]1CCCO1 QRIBXVGHDLFNNE-PEMQHITISA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GAMMOYWIGOUVQR-MDLDFJCZSA-N tert-butyl (6r,7r)-7-amino-3-(oxan-2-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound O=C([C@@H](N)[C@H]1SC2)N1C(C(=O)OC(C)(C)C)=C2C1CCCCO1 GAMMOYWIGOUVQR-MDLDFJCZSA-N 0.000 description 1
- VDIBVAKPTLIVJC-QHNQYTFYSA-N tert-butyl (6r,7r)-8-oxo-3-(oxolan-2-yl)-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound N([C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)OC(C)(C)C)C1OCCC1)C(=O)COC1=CC=CC=C1 VDIBVAKPTLIVJC-QHNQYTFYSA-N 0.000 description 1
- MTOYIDLPMZXRBE-HJSRJYPHSA-N tert-butyl 2-chloro-2-[(2r,3r)-2-[2-(oxan-2-yl)-2-oxoethyl]sulfanyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]acetate Chemical compound S([C@H]1N(C([C@H]1NC(=O)CC=1C=CC=CC=1)=O)C(Cl)C(=O)OC(C)(C)C)CC(=O)C1CCCCO1 MTOYIDLPMZXRBE-HJSRJYPHSA-N 0.000 description 1
- YCXJNMHYSAAGSG-ITYAMSQCSA-N tert-butyl 2-hydroxy-2-[(2r,3r)-2-[2-(oxan-2-yl)-2-oxoethyl]sulfanyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]acetate Chemical compound S([C@H]1N(C([C@H]1NC(=O)CC=1C=CC=CC=1)=O)C(O)C(=O)OC(C)(C)C)CC(=O)C1CCCCO1 YCXJNMHYSAAGSG-ITYAMSQCSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- GYNCCYBVXKBGJL-UHFFFAOYSA-N tributyl(oxolan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1CCCO1 GYNCCYBVXKBGJL-UHFFFAOYSA-N 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical group CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- DGIJAZGPLFOQJE-UHFFFAOYSA-N trimethylsilyl n-trimethylsilylcarbamate Chemical compound C[Si](C)(C)NC(=O)O[Si](C)(C)C DGIJAZGPLFOQJE-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hetero atoms directly attached in position 7
- C07D463/16—Nitrogen atoms
- C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
- C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D463/22—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen further substituted by nitrogen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909016189A GB9016189D0 (en) | 1990-07-24 | 1990-07-24 | Novel compounds |
| GB919109540A GB9109540D0 (en) | 1991-05-02 | 1991-05-02 | Novel compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9100305A0 AP9100305A0 (en) | 1991-07-31 |
| AP832A true AP832A (en) | 2000-05-03 |
Family
ID=26297372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1991/000305A AP832A (en) | 1990-07-24 | 1991-07-22 | 3-Tetrahydrofuran and tetrohydropyrinol ephynolsporens and analogues. |
Country Status (26)
| Country | Link |
|---|---|
| EP (2) | EP0540606A1 (fr) |
| JP (2) | JPH05509089A (fr) |
| KR (1) | KR100189075B1 (fr) |
| CN (2) | CN1061046C (fr) |
| AP (1) | AP832A (fr) |
| AT (1) | ATE185567T1 (fr) |
| AU (1) | AU648329B2 (fr) |
| CA (2) | CA2087967C (fr) |
| CZ (1) | CZ6493A3 (fr) |
| DE (2) | DE69131714T2 (fr) |
| DK (1) | DK0540609T3 (fr) |
| ES (1) | ES2137162T3 (fr) |
| FI (1) | FI930270L (fr) |
| GR (1) | GR3031711T3 (fr) |
| HU (1) | HUT63628A (fr) |
| IE (1) | IE912569A1 (fr) |
| IL (1) | IL98909A0 (fr) |
| LU (1) | LU91290I2 (fr) |
| MX (1) | MX9100317A (fr) |
| MY (1) | MY106399A (fr) |
| NL (1) | NL300249I1 (fr) |
| NO (1) | NO930226L (fr) |
| NZ (1) | NZ239061A (fr) |
| PT (1) | PT98426A (fr) |
| WO (2) | WO1992001696A1 (fr) |
| YU (1) | YU129691A (fr) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9125645D0 (en) * | 1991-12-03 | 1992-01-29 | Smithkline Beecham Plc | Novel compounds |
| EP0624160B1 (fr) * | 1992-01-22 | 2001-10-31 | Pfizer Inc. | Derives de 2-isocephem et d'oxacephem, procedes de preparation, les intermediaires de ceux-ci et leur utilisation comme agents antibacteriens |
| GB9212609D0 (en) * | 1992-06-13 | 1992-07-29 | Smithkline Beecham Plc | Novel compounds |
| GB9213567D0 (en) * | 1992-06-26 | 1992-08-12 | Smithkline Beecham Plc | Novel compounds |
| GB9424847D0 (en) * | 1994-12-09 | 1995-02-08 | Smithkline Beecham Plc | Novel process |
| GB2300856A (en) * | 1995-05-16 | 1996-11-20 | Pfizer Ltd | Beta-lactam preparation |
| WO1998014421A1 (fr) * | 1996-10-02 | 1998-04-09 | Daiichi Pharmaceutical Co., Ltd. | Procede d'esterification de composes carboxyliques |
| FR2776292B1 (fr) | 1998-03-20 | 2004-09-10 | Oncopharm | Cephalotaxanes porteurs de chaine laterale et leur procede de synthese |
| GB0019124D0 (en) * | 2000-08-03 | 2000-09-27 | Pfizer | Novel process |
| RU2237670C1 (ru) * | 2000-12-04 | 2004-10-10 | Пфайзер Продактс Инк. | Способ взаимодействия и промежуточные продукты, пригодные для получения цефалоспоринов |
| BR0115872A (pt) * | 2000-12-04 | 2003-10-28 | Pfizer Prod Inc | Processo e derivados de éster úteis para a preparação de cefalosporinas |
| US7378408B2 (en) * | 2001-11-30 | 2008-05-27 | Pfizer Inc. | Methods of treatment and formulations of cephalosporin |
| KR100710555B1 (ko) | 2001-12-04 | 2007-04-24 | 에스케이 주식회사 | 광학적으로 순수한 (ｒ)-폼 또는 (ｓ)-폼의테트라히드로퓨라닐 케톤의 제조방법 |
| SI2794627T1 (sl) | 2011-12-22 | 2019-02-28 | Alios Biopharma, Inc. | Substituirani nukleozidi, nukleotidi in njihovi analogi |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| PL2861611T3 (pl) | 2012-05-25 | 2017-08-31 | Janssen Sciences Ireland Uc | Nukleozydy uracylowe spirooksetanu |
| ES2865402T3 (es) | 2012-12-21 | 2021-10-15 | Janssen Biopharma Inc | 4'-fluoronucleósidos, 4'-fluoronucleótidos y análogos de los mismos para el tratamiento del VHC |
| CN105254648B (zh) * | 2015-11-13 | 2018-04-03 | 广东温氏大华农生物科技有限公司 | 一种头孢维星及其钠盐的合成方法 |
| GB2575261B (en) | 2018-07-02 | 2022-03-09 | Norbrook Lab Ltd | Intermediates in the synthesis of C3-substituted cephalosporins |
| AU2019324170A1 (en) | 2018-08-23 | 2021-02-18 | Seagen, Inc. | Anti-TIGIT antibodies |
| CR20220316A (es) | 2019-12-06 | 2022-10-07 | Vertex Pharma | Tetrahidrofuranos sustituidos como moduladores de canales de sodio |
| TWI775313B (zh) | 2020-02-18 | 2022-08-21 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| TWI883391B (zh) | 2020-02-18 | 2025-05-11 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| AU2021224588B2 (en) | 2020-02-18 | 2024-07-18 | Gilead Sciences, Inc. | Antiviral compounds |
| CN114213433B (zh) * | 2020-06-08 | 2023-03-24 | 重庆医药高等专科学校 | C-3位四氢呋喃取代的头孢菌素-铁载体耦合物的制备方法 |
| KR20230170745A (ko) | 2021-04-16 | 2023-12-19 | 길리애드 사이언시즈, 인코포레이티드 | 아미드를 사용한 카르바뉴클레오시드를 제조하는 방법 |
| JP2024522292A (ja) | 2021-06-04 | 2024-06-13 | バーテックス ファーマシューティカルズ インコーポレイテッド | ナトリウムチャネルのモジュレーターとしてのｎ－（ヒドロキシアルキル（ヘテロ）アリール）テトラヒドロフランカルボキサミド |
| US12116380B2 (en) | 2021-08-18 | 2024-10-15 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2300009A1 (de) * | 1971-12-31 | 1973-07-12 | Roussel Uclaf | Verfahren zur herstellung neuer cephalosporinderivate sowie die erhaltenen produkte |
| GB1385831A (en) * | 1972-05-05 | 1975-03-05 | Hoechst Ag | Acylamino-cephem-carboxylic acids and process for their preparation |
| EP0075805A1 (fr) * | 1981-09-18 | 1983-04-06 | Kyowa Hakko Kogyo Co., Ltd | Composé beta-lactame et une composition pharmaceutique le contenant |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2197573A1 (en) * | 1972-09-07 | 1974-03-29 | Roussel Uclaf | 7-substd-phenylacetamido-cephalosporin derivs - - antibiotics active against streptococci and staphylococci |
| BE791160A (fr) * | 1972-01-03 | 1973-05-09 | Beecham Group Ltd | Nouveaux cephemes substitues |
| BE791161A (fr) * | 1972-01-03 | 1973-05-09 | Beecham Group Ltd | Procede pour la preparation d'analogues des cephalosporines |
| GB8821797D0 (en) * | 1988-09-16 | 1988-10-19 | Beecham Group Plc | Novel compounds |
| ATE171705T1 (de) * | 1989-03-30 | 1998-10-15 | Pfizer | Cephalosporine und ihre homologen, verfahren zu ihrer herstellung und pharmazeutische präparate |
-
1991
- 1991-07-16 MY MYPI91001321A patent/MY106399A/en unknown
- 1991-07-22 MX MX9100317A patent/MX9100317A/es unknown
- 1991-07-22 DE DE69131714T patent/DE69131714T2/de not_active Expired - Lifetime
- 1991-07-22 WO PCT/GB1991/001228 patent/WO1992001696A1/fr not_active Ceased
- 1991-07-22 FI FI930270A patent/FI930270L/fi unknown
- 1991-07-22 JP JP3512255A patent/JPH05509089A/ja active Pending
- 1991-07-22 NZ NZ239061A patent/NZ239061A/en not_active IP Right Cessation
- 1991-07-22 EP EP91913545A patent/EP0540606A1/fr not_active Withdrawn
- 1991-07-22 CZ CS9364A patent/CZ6493A3/cs unknown
- 1991-07-22 DK DK91913583T patent/DK0540609T3/da active
- 1991-07-22 JP JP3512368A patent/JP2851428B2/ja not_active Expired - Lifetime
- 1991-07-22 AT AT91913583T patent/ATE185567T1/de active
- 1991-07-22 AP APAP/P/1991/000305A patent/AP832A/en active
- 1991-07-22 EP EP91913583A patent/EP0540609B1/fr not_active Expired - Lifetime
- 1991-07-22 AU AU82224/91A patent/AU648329B2/en not_active Expired
- 1991-07-22 DE DE200612000065 patent/DE122006000065I2/de active Active
- 1991-07-22 IL IL98909A patent/IL98909A0/xx unknown
- 1991-07-22 HU HU93177A patent/HUT63628A/hu unknown
- 1991-07-22 CA CA002087967A patent/CA2087967C/fr not_active Expired - Lifetime
- 1991-07-22 WO PCT/GB1991/001227 patent/WO1992001695A1/fr not_active Ceased
- 1991-07-22 IE IE256991A patent/IE912569A1/en not_active IP Right Cessation
- 1991-07-22 KR KR1019930700216A patent/KR100189075B1/ko not_active Expired - Lifetime
- 1991-07-22 CA CA002359744A patent/CA2359744C/fr not_active Expired - Lifetime
- 1991-07-22 ES ES91913583T patent/ES2137162T3/es not_active Expired - Lifetime
- 1991-07-23 YU YU129691A patent/YU129691A/sh unknown
- 1991-07-23 PT PT98426A patent/PT98426A/pt not_active Application Discontinuation
- 1991-07-24 CN CN91105783A patent/CN1061046C/zh not_active Expired - Lifetime
-
1993
- 1993-01-22 NO NO93930226A patent/NO930226L/no unknown
-
1998
- 1998-11-14 CN CN98122407A patent/CN1111410C/zh not_active Expired - Lifetime
-
1999
- 1999-11-03 GR GR990402803T patent/GR3031711T3/el unknown
-
2006
- 2006-11-22 LU LU91290C patent/LU91290I2/fr unknown
- 2006-11-27 NL NL300249C patent/NL300249I1/nl unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2300009A1 (de) * | 1971-12-31 | 1973-07-12 | Roussel Uclaf | Verfahren zur herstellung neuer cephalosporinderivate sowie die erhaltenen produkte |
| GB1385831A (en) * | 1972-05-05 | 1975-03-05 | Hoechst Ag | Acylamino-cephem-carboxylic acids and process for their preparation |
| EP0075805A1 (fr) * | 1981-09-18 | 1983-04-06 | Kyowa Hakko Kogyo Co., Ltd | Composé beta-lactame et une composition pharmaceutique le contenant |
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