FR2470771A1 - Procede de preparation des derives de l'acide 7-amino-desacetoxy cephalosporanique - Google Patents
Procede de preparation des derives de l'acide 7-amino-desacetoxy cephalosporanique Download PDFInfo
- Publication number
- FR2470771A1 FR2470771A1 FR8011568A FR8011568A FR2470771A1 FR 2470771 A1 FR2470771 A1 FR 2470771A1 FR 8011568 A FR8011568 A FR 8011568A FR 8011568 A FR8011568 A FR 8011568A FR 2470771 A1 FR2470771 A1 FR 2470771A1
- Authority
- FR
- France
- Prior art keywords
- adca
- acetone
- mixture
- preparation
- mixed anhydride
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical class S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 title claims description 64
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 86
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 23
- 150000004682 monohydrates Chemical class 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 51
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 25
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- -1 ethoxyl Chemical group 0.000 claims description 12
- 229910001868 water Inorganic materials 0.000 claims description 8
- 239000012467 final product Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000003839 salts Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
- 125000001240 enamine group Chemical group 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 101150035983 str1 gene Proteins 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 28
- 150000001875 compounds Chemical group 0.000 abstract description 11
- 229940047526 cephalexin monohydrate Drugs 0.000 abstract description 8
- YGZIWEZFFBPCLN-UHFFFAOYSA-N n,3-bis(2-chloroethyl)-4-hydroperoxy-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine Chemical compound OOC1CCOP(=O)(NCCCl)N1CCCl YGZIWEZFFBPCLN-UHFFFAOYSA-N 0.000 abstract description 8
- 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 abstract description 3
- NVIAYEIXYQCDAN-UHFFFAOYSA-N 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)C12 NVIAYEIXYQCDAN-UHFFFAOYSA-N 0.000 abstract description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 abstract description 2
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 abstract 1
- ZHNUHDYFZUAESO-NJFSPNSNSA-N aminoformaldehyde Chemical compound N[14CH]=O ZHNUHDYFZUAESO-NJFSPNSNSA-N 0.000 abstract 1
- 229940113088 dimethylacetamide Drugs 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 18
- 238000004090 dissolution Methods 0.000 description 16
- 239000000725 suspension Substances 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 230000002906 microbiologic effect Effects 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 229940106164 cephalexin Drugs 0.000 description 10
- AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin 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=CC=C1 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 230000001960 triggered effect Effects 0.000 description 5
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000002081 enamines Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FPFFJBYKCLCHSC-UHFFFAOYSA-N [K]C Chemical class [K]C FPFFJBYKCLCHSC-UHFFFAOYSA-N 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- UQFHJDVUQSAVOQ-UHFFFAOYSA-N (2-aminophenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1N UQFHJDVUQSAVOQ-UHFFFAOYSA-N 0.000 description 1
- IAZPUJDTYUZJMI-OGFXRTJISA-N (2r)-2-amino-2-phenylacetic acid;hydrochloride Chemical compound Cl.OC(=O)[C@H](N)C1=CC=CC=C1 IAZPUJDTYUZJMI-OGFXRTJISA-N 0.000 description 1
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 1
- BQLUUGXNYOGDMW-UHFFFAOYSA-N 2-phenoxy-3-phenylpropanoic acid Chemical compound C=1C=CC=CC=1OC(C(=O)O)CC1=CC=CC=C1 BQLUUGXNYOGDMW-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 1
- QDIHWPOGZVZVEQ-UHFFFAOYSA-N ClO.OC1=CC=C(C(N)C(=O)Cl)C=C1 Chemical compound ClO.OC1=CC=C(C(N)C(=O)Cl)C=C1 QDIHWPOGZVZVEQ-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens 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
- HBVZRPAKZOLBPL-UHFFFAOYSA-N O-Acetylethanolamine Chemical compound CC(=O)OCCN HBVZRPAKZOLBPL-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- WSNSMPZJJIYZCV-UHFFFAOYSA-N [Na]C Chemical class [Na]C WSNSMPZJJIYZCV-UHFFFAOYSA-N 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT27962/79A IT1126544B (it) | 1979-12-07 | 1979-12-07 | Procedimento per la preparazione di derivati dell'acido 7-amino-desacetossi cefalosporanico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2470771A1 true FR2470771A1 (fr) | 1981-06-12 |
| FR2470771B1 FR2470771B1 (en, 2012) | 1984-04-27 |
Family
ID=11222690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8011568A Granted FR2470771A1 (fr) | 1979-12-07 | 1980-05-23 | Procede de preparation des derives de l'acide 7-amino-desacetoxy cephalosporanique |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4299955A (en, 2012) |
| JP (1) | JPS5683492A (en, 2012) |
| KR (1) | KR830002454B1 (en, 2012) |
| CH (1) | CH645647A5 (en, 2012) |
| DE (1) | DE3012669A1 (en, 2012) |
| FR (1) | FR2470771A1 (en, 2012) |
| GB (1) | GB2064511B (en, 2012) |
| IT (1) | IT1126544B (en, 2012) |
| NL (1) | NL191239C (en, 2012) |
| YU (1) | YU125780A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1532682A (en) * | 1976-04-27 | 1978-11-22 | Bristol Myers Co | Process for the preparation of cephadroxil |
| ES488286A0 (es) * | 1980-02-05 | 1980-12-16 | Liofilizaciones Esterilizacion | Procedimiento para la obtencion de una sal soluble en agua de cefadroxilo |
| YU44832B (en) * | 1981-08-03 | 1991-04-30 | Pliva Pharm & Chem Works | Process for preparing semisynthetic cephalosporins |
| HU221200B1 (en) * | 1990-01-22 | 2002-08-28 | Biochemie Gmbh | Process for producing beta-lactames |
| GB9115203D0 (en) * | 1991-07-15 | 1991-08-28 | Biochemie Gmbh | Improvements in or relating to beta lactam production |
| GB9423459D0 (en) * | 1994-11-21 | 1995-01-11 | Biochemie Gmbh | Silylation process |
| US5908929A (en) * | 1996-12-05 | 1999-06-01 | Vitara Chemicals Limited | Process for the manufacture of the antibiotic 7-(D-α-amino-α-phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid (cephalexin) and pharmaceutically acceptable salts thereof |
| US20040077849A1 (en) * | 2002-10-16 | 2004-04-22 | Orchid Chemicals & Pharmaceuticals Limited | Process for the preparation of cefadroxil |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985741A (en) * | 1972-09-15 | 1976-10-12 | Bristol-Myers Company | Production of p-hydroxycephalexin |
| EP0001133A1 (en) * | 1977-09-06 | 1979-03-21 | Gist-Brocades N.V. | Process for the preparation of 6- D-alpha-amino-(p-hydroxyphenyl)-acetamido penicillanic acid |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3531481A (en) * | 1969-04-21 | 1970-09-29 | Lilly Co Eli | Method for manufacture of crystalline cephalosporin |
| US3502663A (en) * | 1969-04-21 | 1970-03-24 | Lilly Co Eli | Crystalline cephalosporin,method for its manufacture |
| GB1327270A (en) | 1970-10-26 | 1973-08-22 | Osaka Univeristy President Of | Acylation of 6-aminopenicillanic acid and 7-aminocephalospor anic acids |
| BE793191A (fr) * | 1971-12-28 | 1973-06-22 | Toyama Chemical Co Ltd | Procede pour produire des acides 7-acylamido-3-cephem-4- carboxyliques |
| YU39709B (en) * | 1972-09-15 | 1985-04-30 | Bristol Myers Co | Process for producing cephalosporin |
| US3965098A (en) | 1972-11-29 | 1976-06-22 | American Home Products Corporation | Intermediates for preparing cephalosporins and methods of production |
| GB1472746A (en) * | 1973-07-05 | 1977-05-04 | Glaxo Lab Ltd | Cephalosporin compounds |
| GB1473090A (en, 2012) * | 1973-07-19 | 1977-05-11 | ||
| ES419149A1 (es) * | 1973-09-28 | 1976-07-01 | Fener S L Lab | Procedimiento para la obtencion de a-amino-penicilinas y cefalosporinas. |
| NL166831C (nl) * | 1974-07-17 | 1981-09-15 | Nederlanden Staat | Inrichting voor het bewaken van de kwaliteit van straalverbindingen. |
| JPS5129489A (en) * | 1974-08-30 | 1976-03-12 | Kanebo Ltd | Penishirinrui oyobi sefuarosuhorinrui no seizoho |
| JPS51105091A (en) * | 1975-03-12 | 1976-09-17 | Sangyo Kagaku Kenkyu Kyokai | Aminoashirukano kairyohoho |
| JPS5283490A (en) * | 1975-12-30 | 1977-07-12 | Tokyo Tanabe Co | Process for preparing 77glycylamino cephlospoline derivatives |
| GB1532682A (en) | 1976-04-27 | 1978-11-22 | Bristol Myers Co | Process for the preparation of cephadroxil |
| AT363594B (de) * | 1978-02-01 | 1981-08-10 | Biochemie Gmbh | Verfahren zur herstellung eines neuen formamidkomplexes von 7-beta-(d-2-amino-2-phenylacetamido)-3-methylceph-3-emcarbonsaeure |
-
1979
- 1979-12-07 IT IT27962/79A patent/IT1126544B/it active
-
1980
- 1980-03-24 US US06/132,761 patent/US4299955A/en not_active Expired - Lifetime
- 1980-04-01 DE DE19803012669 patent/DE3012669A1/de active Granted
- 1980-04-07 KR KR1019800001443A patent/KR830002454B1/ko not_active Expired
- 1980-04-11 JP JP4701280A patent/JPS5683492A/ja active Granted
- 1980-05-12 GB GB8015590A patent/GB2064511B/en not_active Expired
- 1980-05-12 YU YU01257/80A patent/YU125780A/xx unknown
- 1980-05-23 FR FR8011568A patent/FR2470771A1/fr active Granted
- 1980-05-29 CH CH417780A patent/CH645647A5/it not_active IP Right Cessation
- 1980-11-21 NL NL8006367A patent/NL191239C/xx not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985741A (en) * | 1972-09-15 | 1976-10-12 | Bristol-Myers Company | Production of p-hydroxycephalexin |
| EP0001133A1 (en) * | 1977-09-06 | 1979-03-21 | Gist-Brocades N.V. | Process for the preparation of 6- D-alpha-amino-(p-hydroxyphenyl)-acetamido penicillanic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| CH645647A5 (it) | 1984-10-15 |
| IT7927962A0 (it) | 1979-12-07 |
| DE3012669A1 (de) | 1981-06-11 |
| IT1126544B (it) | 1986-05-21 |
| KR830002454B1 (ko) | 1983-10-26 |
| US4299955A (en) | 1981-11-10 |
| FR2470771B1 (en, 2012) | 1984-04-27 |
| YU125780A (en) | 1983-04-30 |
| DE3012669C2 (en, 2012) | 1991-05-08 |
| NL191239C (nl) | 1995-04-03 |
| GB2064511A (en) | 1981-06-17 |
| JPH034555B2 (en, 2012) | 1991-01-23 |
| NL8006367A (nl) | 1981-07-01 |
| GB2064511B (en) | 1983-06-22 |
| NL191239B (nl) | 1994-11-01 |
| JPS5683492A (en) | 1981-07-08 |
| KR830002774A (ko) | 1983-05-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1926102B (zh) | N-保护的4-酮脯氨酸衍生物的制备方法 | |
| EP0088853B1 (fr) | Nouveaux dérivés de pyridinium thiométhyl céphalosporines, procédé pour leur préparation et compositions pharmaceutiques les contenant | |
| FR2470771A1 (fr) | Procede de preparation des derives de l'acide 7-amino-desacetoxy cephalosporanique | |
| FR2688506A1 (fr) | Procede de preparation de sels de l'acide clavulanique. | |
| FR2570702A1 (fr) | Derives des cephalosporines, procedes d'obtention et leur application a titre d'antibiotiques | |
| JPH10511377A (ja) | セフォタキシムの製造 | |
| KR100527648B1 (ko) | Ｎ-(1(ｓ)-에톡시카르보닐-3-페닐프로필)-ｌ-알라닌ｎ-카르복시무수물의 결정화 방법 | |
| EP0539460B1 (fr) | Sels derives de la dialcoylaminoalcoylsulfonyl-26 pristinamycine ii b | |
| FR2476090A1 (fr) | Procede de preparation de l'acide 7-(d(-)-a-amino-p-hydroxyphenyl-acetamido) desacetoxycephalosporanique | |
| FR2647446A1 (fr) | Procede pour la preparation selective de 1,4-diamino-2-nitrobenzenes substitues en n4 | |
| FR2468609A1 (fr) | Procede de fabrication de l'acide 6-d-a-amino-p-hydroxyphenylacetamido penicillanique | |
| EP0643056B1 (fr) | Procédé de préparation stéréospécifique de dérivés de 1,3-dioxane-4,6-diones précurseurs de dérivés d'acides tétramiques chiraux | |
| FR2501685A1 (fr) | Nouveaux derives du pyrazole | |
| CH637967A5 (fr) | Produit d'addition du n,n-dimethylacetamide et d'un derive d'un acide cephem-4-carboxylique et procede de sa preparation. | |
| FR2555989A1 (fr) | Monohydrate de chlorocephadroxyle | |
| BE886467A (fr) | Procede de preparation de derives d'antibiotiques de la serie des beta-lactames, produits intermediaires nouveaux et procede de preparation de ceux-ci | |
| BE876466A (fr) | Derive de l'acide penicillanique et son procede de preparation | |
| KR820001452B1 (ko) | 페니실란산 유도체의 제조방법 | |
| WO2005095332A1 (fr) | Derives d’amino-acides utiles comme agents de liaison a un support solide | |
| FR2653765A1 (fr) | Procede pour la preparation enantioselective de 2-aminotetralines. | |
| EP1151996A2 (fr) | Procédé de préparation des N,N'-carbonyl bis lactames | |
| FR2493837A1 (fr) | Nouveau procede de preparation d'un derive de glycine et produit obtenu par ce procede | |
| FR2536400A1 (fr) | 3-(1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxopurine-7-acetyl)-8-(2-phenylethyl)-1-oxa-3,8-diazaspiro (4,5) decane-2-one, utile comme bronchodilatateur ou anti-inflammatoire, et son procede de preparation | |
| FR2486943A1 (en, 2012) | ||
| FR2528832A1 (fr) | Nouveaux derives du benzene, leur preparation et leur utilisation comme medicaments |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |