CA2519853A1 - Procede de preparation de composes de 7-amino(p-hydroxyphenylglycyl) cephem - Google Patents

Procede de preparation de composes de 7-amino(p-hydroxyphenylglycyl) cephem Download PDF

Info

Publication number: CA2519853A1
Authority: CA; Canada
Prior art keywords: formula; group; methyl; alkyl; amino
Prior art date: 2003-03-21
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.): Abandoned

Application number

CA002519853A

Other languages

English (en)

Inventor

Neera Tewari

Shailendra Kumar Singh

Bishwa Prakash Rai

Yatendra Kumar

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.)

Ranbaxy Laboratories Ltd

Original Assignee

Individual

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.)

2003-03-21

Filing date

2004-03-22

Publication date

2004-09-30

2004-03-22 Application filed by Individual filed Critical Individual

2004-09-30 Publication of CA2519853A1 publication Critical patent/CA2519853A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 42
-1 cephem compounds Chemical class 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title abstract description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 12
239000012535 impurity Substances 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
RJFPBECTFIUTHB-BAFYGKSASA-N (6r)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC=C(C(O)=O)N2C(=O)C(N)[C@H]21 RJFPBECTFIUTHB-BAFYGKSASA-N 0.000 claims description 6
125000006017 1-propenyl group Chemical group 0.000 claims description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 6
229910052700 potassium Inorganic materials 0.000 claims description 6
239000011591 potassium Substances 0.000 claims description 6
QMWWAEFYIXXXQW-UHFFFAOYSA-M potassium;2-[(4-ethoxy-4-oxobut-2-en-2-yl)amino]-2-phenylacetate Chemical compound [K+].CCOC(=O)C=C(C)NC(C([O-])=O)C1=CC=CC=C1 QMWWAEFYIXXXQW-UHFFFAOYSA-M 0.000 claims description 6
238000006884 silylation reaction Methods 0.000 claims description 6
125000003107 substituted aryl group Chemical group 0.000 claims description 6
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
125000001072 heteroaryl group Chemical group 0.000 claims description 5
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
QHUOBLDKFGCVCG-UHFFFAOYSA-N n-methyl-n-trimethylsilylacetamide Chemical compound CC(=O)N(C)[Si](C)(C)C QHUOBLDKFGCVCG-UHFFFAOYSA-N 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
208000035143 Bacterial infection Diseases 0.000 claims 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 claims description 3
239000002253 acid Substances 0.000 claims description 3
208000022362 bacterial infectious disease Diseases 0.000 claims description 3
239000006184 cosolvent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
150000008282 halocarbons Chemical class 0.000 claims description 3
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
229940011051 isopropyl acetate Drugs 0.000 claims description 3
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
GGGUKEUZOYLABH-CYBMUJFWSA-N (2r)-2-[(4-ethoxy-4-oxobut-2-en-2-yl)amino]-2-(4-hydroxyphenyl)acetic acid Chemical compound CCOC(=O)C=C(C)N[C@@H](C(O)=O)C1=CC=C(O)C=C1 GGGUKEUZOYLABH-CYBMUJFWSA-N 0.000 claims description 2
QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 claims description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 2
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 2
150000002576 ketones Chemical class 0.000 claims 2
VXLHFWHJVCLKPT-GFCCVEGCSA-N (2r)-2-(4-hydroxyphenyl)-2-[(4-methoxy-4-oxobut-2-en-2-yl)amino]acetic acid Chemical compound COC(=O)C=C(C)N[C@@H](C(O)=O)C1=CC=C(O)C=C1 VXLHFWHJVCLKPT-GFCCVEGCSA-N 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
150000008064 anhydrides Chemical class 0.000 description 7
ALYUMNAHLSSTOU-CIRGZYLNSA-N (6r,7r)-7-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(e)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)/C=C/C)C(O)=O)=CC=C(O)C=C1 ALYUMNAHLSSTOU-CIRGZYLNSA-N 0.000 description 6
NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000012453 solvate Substances 0.000 description 6
229960004841 cefadroxil Drugs 0.000 description 5
229960002580 cefprozil Drugs 0.000 description 5
229940124587 cephalosporin Drugs 0.000 description 5
229930186147 Cephalosporin Natural products 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
150000001780 cephalosporins Chemical class 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZYLDQHILNOZKIF-OXLALJFOSA-N (6r,7r)-7-azaniumyl-8-oxo-3-[(z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC(\C=C/C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 ZYLDQHILNOZKIF-OXLALJFOSA-N 0.000 description 2
NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000002775 capsule Substances 0.000 description 2
UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 2
229960002420 cefatrizine Drugs 0.000 description 2
150000001782 cephems Chemical class 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
XUZTXXZGJMGKTN-UHFFFAOYSA-N (2-amino-4-hydroxyphenyl) acetate Chemical compound CC(=O)OC1=CC=C(O)C=C1N XUZTXXZGJMGKTN-UHFFFAOYSA-N 0.000 description 1
ZYLDQHILNOZKIF-IOJJLOCKSA-N (6R)-7-amino-8-oxo-3-prop-1-enyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC=CC1=C(N2[C@H](SC1)C(N)C2=O)C(O)=O ZYLDQHILNOZKIF-IOJJLOCKSA-N 0.000 description 1
125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 description 1
LQVXSNNAFNGRAH-QHCPKHFHSA-N BMS-754807 Chemical compound C([C@@]1(C)C(=O)NC=2C=NC(F)=CC=2)CCN1C(=NN1C=CC=C11)N=C1NC(=NN1)C=C1C1CC1 LQVXSNNAFNGRAH-QHCPKHFHSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LJCWONGJFPCTTL-ZETCQYMHSA-N L-4-hydroxyphenylglycine Chemical compound OC(=O)[C@@H](N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-ZETCQYMHSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229960001065 cefadroxil monohydrate Drugs 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
- C07D501/06—Acylation of 7-aminocephalosporanic acid
- 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
- 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
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
- 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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- 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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (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)

CA002519853A 2003-03-21 2004-03-22 Procede de preparation de composes de 7-amino(p-hydroxyphenylglycyl) cephem Abandoned CA2519853A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IN353DE2003		2003-03-21
IN353/DEL/2003		2003-03-21
PCT/IB2004/000850 WO2004083172A2 (fr)	2003-03-21	2004-03-22	Procede de preparation de composes de 7-amino(p-hydroxyphenylglycyl) cephem

Publications (1)

Publication Number	Publication Date
CA2519853A1 true CA2519853A1 (fr)	2004-09-30

Family

ID=33017825

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002519853A Abandoned CA2519853A1 (fr)	2003-03-21	2004-03-22	Procede de preparation de composes de 7-amino(p-hydroxyphenylglycyl) cephem

Country Status (3)

Country	Link
EP (1)	EP1608661A2 (fr)
CA (1)	CA2519853A1 (fr)
WO (1)	WO2004083172A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2213676A1 (fr) *	2004-11-01	2010-08-04	Hetero Drugs Limited	Nouveau procédé de préparation de cefprozil
CN102408438B (zh) *	2010-09-26	2015-01-07	石药集团中奇制药技术（石家庄）有限公司	一种头孢丙烯一水合物的制备方法
CN102443013B (zh) *	2010-10-10	2014-09-17	石药集团中奇制药技术（石家庄）有限公司	一种头孢丙烯二甲基甲酰胺溶剂化物的制备方法
CN102911187B (zh) *	2012-10-11	2015-03-11	南通康鑫药业有限公司	一种头孢丙烯的回收方法
CN112694487B (zh) *	2020-12-29	2022-04-22	苏州盛达药业有限公司	一种头孢丙烯的制备方法
CN113533591B (zh) *	2021-06-18	2022-08-23	山东罗欣药业集团恒欣药业有限公司	一种头孢丙烯中苯和三聚乙醛的gc分析方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3899394A (en) *	1972-12-26	1975-08-12	Bristol Myers Co	Production of antibacterial agents
FR2215939B1 (fr) *	1973-01-31	1976-07-02	Roussel Uclaf
GB1505345A (en) *	1974-04-10	1978-03-30	Beecham Group Ltd	Cephalosporins
US4148817A (en) *	1976-03-25	1979-04-10	Eli Lilly And Company	Process and intermediates for preparing cephalosporin antibiotics
IT1065387B (it) *	1976-12-16	1985-02-25	Dobfar Spa	Proccedimento per la preparazione di cefalosporine
KR820001564B1 (ko) *	1981-05-09	1982-09-02	동신제약 주식회사	새로운 실릴화제를 이용한 세팔로스포린 유도체의 제조방법
US20040077849A1 (en) *	2002-10-16	2004-04-22	Orchid Chemicals & Pharmaceuticals Limited	Process for the preparation of cefadroxil
US6903211B2 (en) *	2002-10-30	2005-06-07	Orchid Chemicals & Pharmaceuticals Limited	Process for the preparation of 3-propenyl cephalosporin DMF solvate

2004
- 2004-03-22 CA CA002519853A patent/CA2519853A1/fr not_active Abandoned
- 2004-03-22 EP EP04722335A patent/EP1608661A2/fr not_active Withdrawn
- 2004-03-22 WO PCT/IB2004/000850 patent/WO2004083172A2/fr not_active Ceased

Also Published As

Publication number	Publication date
EP1608661A2 (fr)	2005-12-28
WO2004083172A2 (fr)	2004-09-30
WO2004083172A3 (fr)	2004-12-02

Publication	Publication Date	Title
US6552186B2 (en)	2003-04-22	β-lactam production
EP0233271B1 (fr)	1993-03-17	Procede de preparation d'intermediaires de cephalosporine
EP0138552A2 (fr)	1985-04-24	Préparation de 3-biclyclipyridinium-méthyl céphalosporines
EP1068211B1 (fr)	2007-09-19	Procede de purification d'un derive de cephalosporine
US7427692B2 (en)	2008-09-23	Process for preparation of 7-[α-amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid
US5389627A (en)	1995-02-14	Cephem compounds
CA2519853A1 (fr)	2004-09-30	Procede de preparation de composes de 7-amino(p-hydroxyphenylglycyl) cephem
WO2002083634A2 (fr)	2002-10-24	Procede de preparation d'acide de cefpodoxime
EP1319009B1 (fr)	2008-10-22	Intermediaires dans la production de cephalosporine
CA2123788C (fr)	2001-03-13	Compose cepheme, methode de production et preparation pharmaceutique en contenant
HU221199B1 (en)	2002-08-28	Process for producing cephalosporin derivatives
US5998610A (en)	1999-12-07	Silylation process
CZ282160B6 (cs)	1997-05-14	Způsob přípravy cefalosporinového antibiotika
BG61163B1 (bg)	1997-01-31	Метод за получаване на цефалоспоринов антибиотикпри използване на син-изомер на тиазолилов междинен продукт
US4868294A (en)	1989-09-19	Process for preparing cephalosporin intermediates
WO2005040175A2 (fr)	2005-05-06	Procede de preparation d'acides carboxyliques de type cephem
CA1246545A (fr)	1988-12-13	Monohydrate de chlorocefadroxil
US20030162763A1 (en)	2003-08-28	Novel cephalosporin compounds and process for preparing the same
US20050267092A1 (en)	2005-12-01	Novel cephalosporin compounds and process for preparing the same
EP0953569A1 (fr)	1999-11-03	Préparation d'antibiotiques béta-lactamiques en présence d'urée ou d'amide
AU2002307885A1 (en)	2002-10-28	Process for the preparation of cefpodoxime acid
JPS6117837B2 (fr)	1986-05-09
HK1034078B (en)	2008-04-11	Process for purification of a cephalosporin derivative
HK1057542B (en)	2009-07-10	Intermediates in cephalosporin production
CA2411714A1 (fr)	2002-01-03	Nouveaux composes de cephalosporine et procede de preparation de ceux-ci

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2007-03-22	FZDE	Dead