CA1330094C - Composes intermediaires utilises pour la preparation de derives de la cephalosporine, a caracteristiques pharmacocinetiques ameliorees - Google Patents

Composes intermediaires utilises pour la preparation de derives de la cephalosporine, a caracteristiques pharmacocinetiques ameliorees

Info

Publication number: CA1330094C
Authority: CA; Canada
Prior art keywords: group; ppm; acid; product; compounds
Prior art date: 1987-10-08
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 - Fee Related

Application number

CA000616481A

Other languages

English (en)

Inventor

Bernard Labeeuw

Ali Salhi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi SA

Original Assignee

Sanofi SA

Priority date (The priority date 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 date listed.)

1987-10-08

Filing date

1992-09-03

Publication date

1994-06-07

1987-10-08 Priority claimed from FR8713925A external-priority patent/FR2621589B1/fr

1992-09-03 Application filed by Sanofi SA filed Critical Sanofi SA

1992-09-03 Priority to CA000616481A priority Critical patent/CA1330094C/fr

1994-06-07 Application granted granted Critical

1994-06-07 Publication of CA1330094C publication Critical patent/CA1330094C/fr

2008-10-07 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title abstract description 7
229930186147 Cephalosporin Natural products 0.000 title abstract description 6
229940124587 cephalosporin Drugs 0.000 title abstract description 6
150000001780 cephalosporins Chemical class 0.000 title abstract description 6
239000000543 intermediate Substances 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 27
125000003277 amino group Chemical group 0.000 claims abstract description 11
125000006239 protecting group Chemical group 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
239000000047 product Substances 0.000 description 32
150000003839 salts Chemical class 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
239000002253 acid Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
MBOSUUFPSTZLRU-MMZRWCAGSA-N (6r,7r)-3-[[4-(2-aminoethylsulfonylamino)-3-hydroxybenzoyl]oxymethyl]-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1COC(=O)C1=CC=C(NS(=O)(=O)CCN)C(O)=C1 MBOSUUFPSTZLRU-MMZRWCAGSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
-1 inner salts Chemical class 0.000 description 8
238000000034 method Methods 0.000 description 8
230000036470 plasma concentration Effects 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
244000052616 bacterial pathogen Species 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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 2
239000005711 Benzoic acid Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 2
239000005051 trimethylchlorosilane Substances 0.000 description 2
MBOSUUFPSTZLRU-KAEGIUTESA-N (6R)-3-[[4-(2-aminoethylsulfonylamino)-3-hydroxybenzoyl]oxymethyl]-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydrochloride Chemical compound Cl.Cl.NC=1SC=C(N1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)COC(C2=CC(=C(C=C2)NS(=O)(=O)CCN)O)=O)C(=O)O)C1=O)=NOC MBOSUUFPSTZLRU-KAEGIUTESA-N 0.000 description 1
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
NFPYJDZQOKCYIE-UHFFFAOYSA-N 4-amino-3-hydroxybenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1O NFPYJDZQOKCYIE-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
241000588722 Escherichia Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
QRBRBBWNWTZEQK-XGPZGZPHSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.NC=1SC=C(N1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)COC(C2=CC(=C(C=C2)NS(=O)(=O)CCN)O)=O)C(=O)O)C1=O)=NOC(C)(C)C(=O)O Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.NC=1SC=C(N1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)COC(C2=CC(=C(C=C2)NS(=O)(=O)CCN)O)=O)C(=O)O)C1=O)=NOC(C)(C)C(=O)O QRBRBBWNWTZEQK-XGPZGZPHSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
241000282520 Papio Species 0.000 description 1
241001504519 Papio ursinus Species 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000589516 Pseudomonas 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
241000826860 Trapezium Species 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
BHIKCGNWBYJCBR-UHFFFAOYSA-N benzyl n-ethylcarbamate;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.CCNC(=O)OCC1=CC=CC=C1 BHIKCGNWBYJCBR-UHFFFAOYSA-N 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
150000002496 iodine Chemical class 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000003544 oxime group Chemical group 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical group 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
CPKXHHBXZPXCNJ-QLHACJPQSA-N tert-butyl (6R)-3-(iodomethyl)-7-[[2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)CI)C(=O)OC(C)(C)C)C1=O)=NOC(C)(C)C(=O)OC(C)(C)C CPKXHHBXZPXCNJ-QLHACJPQSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
210000002700 urine Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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

Cephalosporin Compounds (AREA)

CA000616481A 1987-10-08 1992-09-03 Composes intermediaires utilises pour la preparation de derives de la cephalosporine, a caracteristiques pharmacocinetiques ameliorees Expired - Fee Related CA1330094C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000616481A CA1330094C (fr)	1987-10-08	1992-09-03	Composes intermediaires utilises pour la preparation de derives de la cephalosporine, a caracteristiques pharmacocinetiques ameliorees

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR8713925A FR2621589B1 (fr)	1987-10-08	1987-10-08	Derives des cephalosporines a pharmacocinetique amelioree, procede pour leur preparation et compositions pharmaceutiques les contenant
US8713925		1987-10-08
CA579575		1988-10-07
CA000616481A CA1330094C (fr)	1987-10-08	1992-09-03	Composes intermediaires utilises pour la preparation de derives de la cephalosporine, a caracteristiques pharmacocinetiques ameliorees

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616481A Division CA1330094C (fr)	1987-10-08	1992-09-03	Composes intermediaires utilises pour la preparation de derives de la cephalosporine, a caracteristiques pharmacocinetiques ameliorees

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616481A Division CA1330094C (fr)	1987-10-08	1992-09-03	Composes intermediaires utilises pour la preparation de derives de la cephalosporine, a caracteristiques pharmacocinetiques ameliorees

Publications (1)

Publication Number	Publication Date
CA1330094C true CA1330094C (fr)	1994-06-07

Family

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616481A Expired - Fee Related CA1330094C (fr)	1987-10-08	1992-09-03	Composes intermediaires utilises pour la preparation de derives de la cephalosporine, a caracteristiques pharmacocinetiques ameliorees

Country Status (1)

Country	Link
CA (1)	CA1330094C (fr)

1992
- 1992-09-03 CA CA000616481A patent/CA1330094C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1997-06-09	MKLA	Lapsed

Publication	Publication Date	Title
US4396620A (en)	1983-08-02	Cephalosporin quinolinium betaines
JPS5858354B2 (ja)	1983-12-24	セフェム誘導体
PL172835B1 (pl)	1997-12-31	Chlorowodorek kwasu 7- ß -[(Z)-2-(2-amino-4-tiazolilo)-2-hydroksyiminoacetamido]-3-(1,2,3-triazol-4-ilo)-tiometylotio-3 -cefemo-4-karboksylowego oraz sposób jego wytwarzania, krystaliczny wodzian chlorowodorku kwasu 7- ß -(Z)-2-(2-amino-4-tiazolilo)-2-hydroksyiminoacetamido]-3-(1,2,3-triazol-4-ilo)-tiometylotio-3-ce- femo-4-karboksylowego oraz sposób jego wytwarzania PL PL PL PL PL
CA1051799A (fr)	1979-04-03	Agents antibacteriens
KR830000853B1 (ko)	1983-04-21	아실 유도체의 제조방법
US4396619A (en)	1983-08-02	Cephalosporin betaines
CS232740B2 (en)	1985-02-14	Method of making pyridiniumthiomethylcephalosporine derivatives
US4476123A (en)	1984-10-09	Antibiotic derivatives, derived from cephalosporins with thiazolyl substituents, pharmaceutical preparations and salts thereof
PL151703B1 (en)	1990-09-28	7-( (meta-substituted) phenylglycine) 1-carba-1-dethiacephalosporins
US5104866A (en)	1992-04-14	Water-soluble antibiotic composition and water-soluble salts of cephem compounds
KR0178956B1 (ko)	1999-03-20	항균성 페넴 에스테르 유도체
CA1330094C (fr)	1994-06-07	Composes intermediaires utilises pour la preparation de derives de la cephalosporine, a caracteristiques pharmacocinetiques ameliorees
US4609654A (en)	1986-09-02	Derivatives of cephalosporins substituted in 3 position by a thiomethyl heterocycle group; and pharmaceutical compositions containing them
AU612414B2 (en)	1991-07-11	Cephalosporin derivatives with improved pharmacokinetics, process for their preparation, pharmaceutical compositions in which they are present and synthesis intermediate
US4929612A (en)	1990-05-29	Thiadiazolylacetamide cephem derivatives
RU2201933C2 (ru)	2003-04-10	Антибактериальные замещенные 7-ациламино-3-(метилгидразоно)метилцефалоспорины, способ их получения, фармацевтические композиции на их основе, промежуточные соединения и способ лечения заболеваний, вызванных микроорганизмами
US5250725A (en)	1993-10-05	Aromatic acid intermediates
US4311842A (en)	1982-01-19	Cephalosporin compounds
NZ204873A (en)	1985-12-13	Heterocyclic derivatives of cephalosporins and pharmaceutical compositions
US4124762A (en)	1978-11-07	7-[(Pyridylthiomethyl)phenyl]acetamido-cephalosporin derivatives
AU597748B2 (en)	1990-06-07	Novel cephalosporin derivatives with improved pharmacokinetics, process for their preparation and pharmaceutical compositions in which they are present
JPS62158289A (ja)	1987-07-14	新規セフアロスポリン誘導体
KR0177844B1 (ko)	1999-03-20	항균성 페넴화합물
KR840002046B1 (ko)	1984-11-06	세팔로스포린의 제조방법
US4107440A (en)	1978-08-15	Intermediates for preparing substituted phenylglycylcephalosporins