JPS609718B2 - チアジアゾリルチオセフアロスポリン類縁抗生物質 - Google Patents
チアジアゾリルチオセフアロスポリン類縁抗生物質Info
- Publication number
- JPS609718B2 JPS609718B2 JP52102261A JP10226177A JPS609718B2 JP S609718 B2 JPS609718 B2 JP S609718B2 JP 52102261 A JP52102261 A JP 52102261A JP 10226177 A JP10226177 A JP 10226177A JP S609718 B2 JPS609718 B2 JP S609718B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- parts
- acids
- add
- stir
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 229940088710 antibiotic agent Drugs 0.000 title 1
- -1 p-hydroxyphenyl Chemical group 0.000 claims description 29
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000002253 acid Substances 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000008282 halocarbons Chemical class 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000002516 radical scavenger Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 3
- JLAMDELLBBZOOX-UHFFFAOYSA-N 3h-1,3,4-thiadiazole-2-thione Chemical class SC1=NN=CS1 JLAMDELLBBZOOX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000219112 Cucumis Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000006178 methyl benzyl group Chemical group 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KHJCBAQZNYPHJJ-ZCFIWIBFSA-N (6R)-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O1CC=C(N2[C@H]1CC2=O)C(=O)O KHJCBAQZNYPHJJ-ZCFIWIBFSA-N 0.000 description 1
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 1
- OPXYNEYEDHAXOM-UHFFFAOYSA-N 3-oxobutanenitrile Chemical compound CC(=O)CC#N OPXYNEYEDHAXOM-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 101100537937 Caenorhabditis elegans arc-1 gene Proteins 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 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 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000271897 Viperidae Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008430 aromatic amides Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- WAVQOKDKPHYRDY-GOSISDBHSA-N benzhydryl (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C([C@H]1SCC=2)C(=O)N1C=2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 WAVQOKDKPHYRDY-GOSISDBHSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000004653 carbonic acids Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000004969 haloethyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- VICXMSDBVFXKGA-UHFFFAOYSA-N pentachloro-$l^{5}-phosphane;pyridine Chemical compound C1=CC=NC=C1.ClP(Cl)(Cl)(Cl)Cl VICXMSDBVFXKGA-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005039 triarylmethyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 239000000273 veterinary drug Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (34)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52102261A JPS609718B2 (ja) | 1977-08-25 | 1977-08-25 | チアジアゾリルチオセフアロスポリン類縁抗生物質 |
| GB17007/78A GB1576796A (en) | 1977-08-25 | 1978-04-28 | Thiadiazolyl cephalosporin analogues |
| NZ188173A NZ188173A (en) | 1977-08-25 | 1978-08-17 | 7-arylmalonamido-7 a-methoxy-3-(optionally alkylated-thiadiazol-2-yl) thiomethyl-1-oxadethiacephalosporins preparation and pharmaceutical and veterinary compositions |
| PT68434A PT68434A (en) | 1977-08-25 | 1978-08-17 | Process for preparing thiadiazolyl cephalosporin analogue |
| CA309,705A CA1101417A (en) | 1977-08-25 | 1978-08-21 | Thiadiazolyl cephalosporin analogues |
| ZA00784753A ZA784753B (en) | 1977-08-25 | 1978-08-21 | Thiadiazolyl cephalosporin analogues |
| CS785485A CS203927B2 (en) | 1977-08-25 | 1978-08-22 | Process for preparing 1-oxadethiacephalosporines |
| AR273406A AR220539A1 (es) | 1977-08-25 | 1978-08-23 | Procedimiento para obtener 7 beta-aril-malonamido-7 alpha-metoxi-3-(tiadiazoliltio)1-oxadetiacefalosporinas y sus sales |
| MX787347U MX5328E (es) | 1977-08-25 | 1978-08-23 | Proceso para la preparacion de analogos de tiadiazolil cefalosporina |
| NO782866A NO782866L (no) | 1977-08-25 | 1978-08-23 | Fremgangsmaate for fremstilling av cefalosporinderivater |
| IE1703/78A IE47630B1 (en) | 1977-08-25 | 1978-08-23 | Thiadiazolyl cephalosporin analogues |
| DD78207438A DD137230A5 (de) | 1977-08-25 | 1978-08-23 | Verfahren zur herstellung von 7 beta-arylmalonamido-7 alpha-methoxy-3-thiadiazolylthio-1-oxadethiacephalosporinen,ihren estern und salzen mit basen |
| FI782586A FI65432C (fi) | 1977-08-25 | 1978-08-24 | Foerfarande foer framstaellning av antibakteriella 7beta-arylmalonamido-7alfa-metoxi-3-tiadiazolyltiometyl-1-detia-1-oxa-3-cefem-4-karbonsyror eller derivat daerav |
| FR7824595A FR2401165A1 (fr) | 1977-08-25 | 1978-08-24 | Procede de preparation d'analogues de thiadiazolylcephalosporine et nouveaux produits ainsi obtenus, a activite antibacterienne |
| DK372878A DK372878A (da) | 1977-08-25 | 1978-08-24 | Thiadiazolylcephalosporinanaloge og fremgangsmaade til fremstilling deraf |
| IL7855429A IL55429A0 (en) | 1977-08-25 | 1978-08-24 | Thiadiaolyl cephalosporin analogs, processes for the preparation thereof,pharmaceutical or veterinary compositions containing the same and method of inhibiting the growth of bacteria therewith |
| ES472817A ES472817A1 (es) | 1977-08-25 | 1978-08-24 | Un procedimiento para preparar analogos de tiadiazolil-cefa-losporina |
| AU39238/78A AU517618B2 (en) | 1977-08-25 | 1978-08-24 | Thriadiazolyl cephalosporin analogues |
| IT68975/78A IT1118098B (it) | 1977-08-25 | 1978-08-24 | Analoghi delle tia diazotil cefalosporine particolarmente utili come antibatterici e procedimento per la loro preparazione |
| US05/936,506 US4201782A (en) | 1977-08-25 | 1978-08-24 | Thiadiazolyl cephalosporin analogs |
| SE7808950A SE452010B (sv) | 1977-08-25 | 1978-08-24 | 7beta-arylmalonamido-7alfa-metoxi-3-eventuellt alkylerade-tiadiazolyltiometyl-1-oxadetiacefalosporiner |
| BE190057A BE869955A (fr) | 1977-08-25 | 1978-08-24 | Thiadiazolyloxadethiacephalosporines |
| PH21699A PH17508A (en) | 1977-08-25 | 1978-08-25 | Thiadiazolyl cephalosporin analogues |
| PL1978209215A PL110656B1 (en) | 1977-08-25 | 1978-08-25 | Method of producing new derivatives of 1-oxadethiacephalosporines |
| AT620378A AT361121B (de) | 1977-08-25 | 1978-08-25 | Verfahren zur herstellung von neuen 7beta-aryl- malonamido-7alpha-methoxy-3-thiadiazolylthio-1- -oxadethiacephalosporinen und deren estern und salzen mit basen |
| GR57086A GR70260B (en, 2012) | 1977-08-25 | 1978-08-25 | |
| BG040749A BG34338A3 (bg) | 1977-08-25 | 1978-08-25 | Метод за получаване на тиадиазолилцефалоспорини |
| HU78SI1644A HU177900B (en) | 1977-08-25 | 1978-08-25 | Process for preparing 7alpha-methoxy-7beta-malonamido-3-/1,3,4-thiadiazoly-5-yl/-thiomethy/-1-dethia-1-oxa-3-cefem-4-carboxylic acid derivatives |
| YU2028/78A YU43999B (en) | 1977-08-25 | 1978-08-25 | Process for obtaining thiadiazolyl analogues of cephalosporin |
| SU782652750A SU812182A3 (ru) | 1977-08-25 | 1978-08-25 | Способ получени 7-метокси-1- ОКСАдЕТиАцЕфАлОСпОРиНОВ или иХСОлЕй |
| NLAANVRAGE7808802,A NL190554C (nl) | 1977-08-25 | 1978-08-25 | Cefalosporinederivaat, en farmaceutisch of veterinair preparaat met antibacteriële werking, dat dit cefalosporinederivaat bevat. |
| RO7895037A RO75070A (ro) | 1977-08-25 | 1978-08-25 | Procedeu de preparare a unor oxadetiacefalosporine |
| CH899678A CH637396A5 (de) | 1977-08-25 | 1978-08-25 | Thiadiazolyl-cephalosporin-analoge. |
| DE19782837264 DE2837264A1 (de) | 1977-08-25 | 1978-08-25 | 7 beta -arylmalonamido-7 alpha -methoxy-3-thiadiazolylthio-1-oxadethiacephalosporine, ihre ester und salze, sowie verfahren zu deren herstellung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52102261A JPS609718B2 (ja) | 1977-08-25 | 1977-08-25 | チアジアゾリルチオセフアロスポリン類縁抗生物質 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5436288A JPS5436288A (en) | 1979-03-16 |
| JPS609718B2 true JPS609718B2 (ja) | 1985-03-12 |
Family
ID=14322642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52102261A Expired JPS609718B2 (ja) | 1977-08-25 | 1977-08-25 | チアジアゾリルチオセフアロスポリン類縁抗生物質 |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4201782A (en, 2012) |
| JP (1) | JPS609718B2 (en, 2012) |
| AR (1) | AR220539A1 (en, 2012) |
| AT (1) | AT361121B (en, 2012) |
| AU (1) | AU517618B2 (en, 2012) |
| BE (1) | BE869955A (en, 2012) |
| BG (1) | BG34338A3 (en, 2012) |
| CA (1) | CA1101417A (en, 2012) |
| CH (1) | CH637396A5 (en, 2012) |
| CS (1) | CS203927B2 (en, 2012) |
| DD (1) | DD137230A5 (en, 2012) |
| DE (1) | DE2837264A1 (en, 2012) |
| DK (1) | DK372878A (en, 2012) |
| ES (1) | ES472817A1 (en, 2012) |
| FI (1) | FI65432C (en, 2012) |
| FR (1) | FR2401165A1 (en, 2012) |
| GB (1) | GB1576796A (en, 2012) |
| GR (1) | GR70260B (en, 2012) |
| HU (1) | HU177900B (en, 2012) |
| IE (1) | IE47630B1 (en, 2012) |
| IL (1) | IL55429A0 (en, 2012) |
| IT (1) | IT1118098B (en, 2012) |
| MX (1) | MX5328E (en, 2012) |
| NL (1) | NL190554C (en, 2012) |
| NO (1) | NO782866L (en, 2012) |
| NZ (1) | NZ188173A (en, 2012) |
| PH (1) | PH17508A (en, 2012) |
| PL (1) | PL110656B1 (en, 2012) |
| PT (1) | PT68434A (en, 2012) |
| RO (1) | RO75070A (en, 2012) |
| SE (1) | SE452010B (en, 2012) |
| SU (1) | SU812182A3 (en, 2012) |
| YU (1) | YU43999B (en, 2012) |
| ZA (1) | ZA784753B (en, 2012) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4259485A (en) * | 1979-04-24 | 1981-03-31 | Eli Lilly And Company | Crystallization process |
| FR2494279A1 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouvelles oxacephalosporines, leur preparation et les medicaments qui les contiennent |
| EP0112049B1 (en) * | 1982-12-14 | 1987-09-09 | Beecham Group Plc | Process for the preparation of beta-lactam compounds |
| JPS60123490A (ja) * | 1983-12-07 | 1985-07-02 | Shionogi & Co Ltd | マロニルオキサセフェムカルボン酸誘導体 |
| US6013835A (en) * | 1995-06-07 | 2000-01-11 | Hfm International, Inc. | Method and apparatus for preparing purified terephthalic acid |
| US6197794B1 (en) | 1998-01-08 | 2001-03-06 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| JP2002504534A (ja) | 1998-02-26 | 2002-02-12 | セルテック・セラピューティクス・リミテッド | α４インテグリンの阻害剤としてのフェニルアラニン誘導体 |
| GB9805655D0 (en) | 1998-03-16 | 1998-05-13 | Celltech Therapeutics Ltd | Chemical compounds |
| US6521626B1 (en) | 1998-03-24 | 2003-02-18 | Celltech R&D Limited | Thiocarboxamide derivatives |
| GB9811159D0 (en) | 1998-05-22 | 1998-07-22 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9811969D0 (en) | 1998-06-03 | 1998-07-29 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9812088D0 (en) | 1998-06-05 | 1998-08-05 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9814414D0 (en) | 1998-07-03 | 1998-09-02 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9821061D0 (en) | 1998-09-28 | 1998-11-18 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9821222D0 (en) | 1998-09-30 | 1998-11-25 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9821406D0 (en) * | 1998-10-01 | 1998-11-25 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9825652D0 (en) | 1998-11-23 | 1999-01-13 | Celltech Therapeutics Ltd | Chemical compounds |
| US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| US6534513B1 (en) | 1999-09-29 | 2003-03-18 | Celltech R&D Limited | Phenylalkanoic acid derivatives |
| US6455539B2 (en) | 1999-12-23 | 2002-09-24 | Celltech R&D Limited | Squaric acid derivates |
| DE60130910T2 (de) | 2000-04-17 | 2008-07-10 | Ucb Pharma, S.A. | Enamin-derivate als zell-adhäsionsmoleküle |
| US6545013B2 (en) | 2000-05-30 | 2003-04-08 | Celltech R&D Limited | 2,7-naphthyridine derivatives |
| US6403608B1 (en) | 2000-05-30 | 2002-06-11 | Celltech R&D, Ltd. | 3-Substituted isoquinolin-1-yl derivatives |
| US6740654B2 (en) | 2000-07-07 | 2004-05-25 | Celltech R & D Limited | Squaric acid derivatives |
| US6649756B2 (en) * | 2000-07-13 | 2003-11-18 | Wyeth, Five Giralda Farms | Process improvement in the preparation of (4r, 5s, 6s)-3-[[(2r,3r)-2-[[[(s)-2-amino-3-methyl-1-oxobutyl]amino]methyl]tetrahydro-3-furanyl]thio]-6-[(r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| AU2001275724A1 (en) | 2000-08-02 | 2002-02-13 | Celltech R&D Limited | 3-substituted isoquinolin-1-yl derivatives |
| CN102827191B (zh) * | 2012-09-24 | 2015-03-11 | 浙江东邦药业有限公司 | 一种氧头孢类化合物的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL178005C (nl) * | 1972-11-06 | 1986-01-02 | Merck & Co Inc | Werkwijze voor het bereiden van een farmaceutisch preparaat met antibacteriele werking, alsmede werkwijze ter bereiding van een cefalosporine-antibioticum. |
| US4045438A (en) * | 1975-10-24 | 1977-08-30 | Yeda Research And Development Co. Ltd. | Cephalosporin antibiotics |
| US4031083A (en) * | 1975-10-24 | 1977-06-21 | Yeda Research And Development Co., Ltd. | Cephalosporin antibiotics |
| FR2361114A1 (fr) * | 1975-11-12 | 1978-03-10 | Shionogi & Co | Procede de preparation d'analogues de cephalosporine a propriete antibacterienne et nouveaux produits ainsi obtenus |
| CA1085392A (en) * | 1976-03-25 | 1980-09-09 | Masayuki Narisada | Arylmalonamido-1-oxadethiacephalosporins |
-
1977
- 1977-08-25 JP JP52102261A patent/JPS609718B2/ja not_active Expired
-
1978
- 1978-04-28 GB GB17007/78A patent/GB1576796A/en not_active Expired
- 1978-08-17 PT PT68434A patent/PT68434A/pt unknown
- 1978-08-17 NZ NZ188173A patent/NZ188173A/xx unknown
- 1978-08-21 ZA ZA00784753A patent/ZA784753B/xx unknown
- 1978-08-21 CA CA309,705A patent/CA1101417A/en not_active Expired
- 1978-08-22 CS CS785485A patent/CS203927B2/cs unknown
- 1978-08-23 AR AR273406A patent/AR220539A1/es active
- 1978-08-23 DD DD78207438A patent/DD137230A5/xx unknown
- 1978-08-23 IE IE1703/78A patent/IE47630B1/en not_active IP Right Cessation
- 1978-08-23 MX MX787347U patent/MX5328E/es unknown
- 1978-08-23 NO NO782866A patent/NO782866L/no unknown
- 1978-08-24 US US05/936,506 patent/US4201782A/en not_active Expired - Lifetime
- 1978-08-24 BE BE190057A patent/BE869955A/xx not_active IP Right Cessation
- 1978-08-24 FR FR7824595A patent/FR2401165A1/fr active Granted
- 1978-08-24 IT IT68975/78A patent/IT1118098B/it active
- 1978-08-24 ES ES472817A patent/ES472817A1/es not_active Expired
- 1978-08-24 DK DK372878A patent/DK372878A/da not_active Application Discontinuation
- 1978-08-24 FI FI782586A patent/FI65432C/fi not_active IP Right Cessation
- 1978-08-24 AU AU39238/78A patent/AU517618B2/en not_active Expired
- 1978-08-24 IL IL7855429A patent/IL55429A0/xx not_active IP Right Cessation
- 1978-08-24 SE SE7808950A patent/SE452010B/sv not_active IP Right Cessation
- 1978-08-25 PL PL1978209215A patent/PL110656B1/pl unknown
- 1978-08-25 GR GR57086A patent/GR70260B/el unknown
- 1978-08-25 YU YU2028/78A patent/YU43999B/xx unknown
- 1978-08-25 CH CH899678A patent/CH637396A5/de not_active IP Right Cessation
- 1978-08-25 BG BG040749A patent/BG34338A3/xx unknown
- 1978-08-25 PH PH21699A patent/PH17508A/en unknown
- 1978-08-25 SU SU782652750A patent/SU812182A3/ru active
- 1978-08-25 HU HU78SI1644A patent/HU177900B/hu not_active IP Right Cessation
- 1978-08-25 RO RO7895037A patent/RO75070A/ro unknown
- 1978-08-25 AT AT620378A patent/AT361121B/de not_active IP Right Cessation
- 1978-08-25 DE DE19782837264 patent/DE2837264A1/de active Granted
- 1978-08-25 NL NLAANVRAGE7808802,A patent/NL190554C/xx not_active IP Right Cessation
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| JPS60197689A (ja) | オキサセフアロスポリンのビニルチオ誘導体 | |
| JPH0454673B2 (en, 2012) | ||
| JPS61130293A (ja) | ふつ素化アルキルセフアロスポリン類 |