NL8005293A - Werkwijze voor de bereiding van 6-d-alfa-amino-p- -hydroxyfenylaceetamido penicillaanzuur. - Google Patents
Werkwijze voor de bereiding van 6-d-alfa-amino-p- -hydroxyfenylaceetamido penicillaanzuur. Download PDFInfo
- Publication number
- NL8005293A NL8005293A NL8005293A NL8005293A NL8005293A NL 8005293 A NL8005293 A NL 8005293A NL 8005293 A NL8005293 A NL 8005293A NL 8005293 A NL8005293 A NL 8005293A NL 8005293 A NL8005293 A NL 8005293A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- preparation
- amino
- mixture
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 41
- 238000002360 preparation method Methods 0.000 title claims description 37
- 239000002253 acid Substances 0.000 title claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 31
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 4
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 4
- 125000001240 enamine group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- -1 silyl compound Chemical class 0.000 description 15
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 14
- 229910052796 boron Inorganic materials 0.000 description 12
- 150000004684 trihydrates Chemical class 0.000 description 12
- 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 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 description 6
- 230000002906 microbiologic effect Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- HVNYTMRNKOKJDT-UHFFFAOYSA-N 2-chloro-1,3,2-dioxaborolane Chemical compound ClB1OCCO1 HVNYTMRNKOKJDT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 3
- 150000001638 boron Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- HBMCQTHGYMTCOF-UHFFFAOYSA-N hydroquinone monoacetate Natural products CC(=O)OC1=CC=C(O)C=C1 HBMCQTHGYMTCOF-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960003022 amoxicillin Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- BIUBIOWCLCUGSQ-UHFFFAOYSA-N chloro(ethoxy)borinic acid Chemical compound CCOB(O)Cl BIUBIOWCLCUGSQ-UHFFFAOYSA-N 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- BCNBMSZKALBQEF-UHFFFAOYSA-N 1,3-dimethylpyrrolidin-2-one Chemical compound CC1CCN(C)C1=O BCNBMSZKALBQEF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MRFJAULKKHVIGF-UHFFFAOYSA-N 2-amino-2-(4-hydroxyphenyl)acetyl chloride;hydrochloride Chemical compound [Cl-].ClC(=O)C([NH3+])C1=CC=C(O)C=C1 MRFJAULKKHVIGF-UHFFFAOYSA-N 0.000 description 1
- ZAKRZZDABWCUGW-UHFFFAOYSA-N 2-aminoacetyl chloride;hydrochloride Chemical compound Cl.NCC(Cl)=O ZAKRZZDABWCUGW-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- XMMFBEWONDCTLD-UHFFFAOYSA-N acetyl(dimethyl)azanium;chloride Chemical compound Cl.CN(C)C(C)=O XMMFBEWONDCTLD-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229960004920 amoxicillin trihydrate Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 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
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2701379 | 1979-11-02 | ||
| IT27013/79A IT1193836B (it) | 1979-11-02 | 1979-11-02 | Procedimento per la produzione di acido 6-d-alfa-amino-p-idrossifenilacetamido enicillanico |
| KR800001442 | 1980-04-07 | ||
| KR1019800001442A KR830002453B1 (ko) | 1979-11-02 | 1980-04-07 | 6-D-α-아미노-P-하이드록시페닐아세트아미도 페니실란산의 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8005293A true NL8005293A (nl) | 1981-06-01 |
Family
ID=26328703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8005293A NL8005293A (nl) | 1979-11-02 | 1980-09-23 | Werkwijze voor de bereiding van 6-d-alfa-amino-p- -hydroxyfenylaceetamido penicillaanzuur. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4310460A (it) |
| JP (1) | JPS5671094A (it) |
| KR (1) | KR830002453B1 (it) |
| CH (1) | CH645377A5 (it) |
| DE (1) | DE3018535A1 (it) |
| FR (1) | FR2468609A1 (it) |
| GB (1) | GB2061260B (it) |
| IT (1) | IT1193836B (it) |
| NL (1) | NL8005293A (it) |
| YU (1) | YU113280A (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1035435C (zh) * | 1993-03-16 | 1997-07-16 | 沈阳医药工业研究所 | 半合成青霉素缩合新工艺 |
| US7230097B2 (en) * | 2003-03-10 | 2007-06-12 | Lupin Ltd. | Process for preparation of 7-[α-Amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB978178A (en) | 1958-10-06 | 1964-12-16 | Beecham Res Lab | Penicillins |
| GB1241844A (en) | 1968-08-23 | 1971-08-04 | Beecham Group Ltd | Penicillins |
| GB1494902A (en) | 1974-05-09 | 1977-12-14 | Glaxo Lab Ltd | Penicillins |
| US3980637A (en) * | 1975-03-17 | 1976-09-14 | Bristol-Myers Company | Production of amoxicillin |
| IT1065394B (it) * | 1976-12-16 | 1985-02-25 | Dobfar Spa | Procedimento per la preparazione di penicilline |
-
1979
- 1979-11-02 IT IT27013/79A patent/IT1193836B/it active
-
1980
- 1980-02-20 JP JP1926680A patent/JPS5671094A/ja active Pending
- 1980-03-24 US US06/133,442 patent/US4310460A/en not_active Expired - Lifetime
- 1980-04-07 KR KR1019800001442A patent/KR830002453B1/ko not_active Expired
- 1980-04-24 YU YU01132/80A patent/YU113280A/xx unknown
- 1980-05-01 GB GB8014460A patent/GB2061260B/en not_active Expired
- 1980-05-14 DE DE19803018535 patent/DE3018535A1/de not_active Withdrawn
- 1980-05-23 FR FR8011567A patent/FR2468609A1/fr active Granted
- 1980-05-29 CH CH417980A patent/CH645377A5/it not_active IP Right Cessation
- 1980-09-23 NL NL8005293A patent/NL8005293A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US4310460A (en) | 1982-01-12 |
| KR830002453B1 (ko) | 1983-10-26 |
| FR2468609A1 (fr) | 1981-05-08 |
| GB2061260A (en) | 1981-05-13 |
| FR2468609B1 (it) | 1984-02-17 |
| DE3018535A1 (de) | 1981-05-14 |
| IT7927013A0 (it) | 1979-11-02 |
| JPS5671094A (en) | 1981-06-13 |
| CH645377A5 (it) | 1984-09-28 |
| IT1193836B (it) | 1988-08-24 |
| YU113280A (en) | 1983-02-28 |
| KR830002771A (ko) | 1983-05-30 |
| GB2061260B (en) | 1983-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3421354B2 (ja) | 結晶性セフジニルアミン塩 | |
| US4504658A (en) | Epimerization of malonic acid esters | |
| EP0188255A2 (en) | Cephem derivatives | |
| CA1269655A (en) | Alkeneamidocephalosporin esters | |
| US5840885A (en) | Processes for the production of 6-α-aminoacyl-penicillin and 7-.alpha. | |
| HK217196A (en) | Diamine salts of clavulanic acid | |
| EP3543236B1 (en) | Method for preparing avibactam intermediate | |
| SU546282A3 (ru) | Способ получени 7- -амино-7 метокси-цефалоспориновых эфиров | |
| US4122086A (en) | Isopenicillins | |
| KR0178280B1 (ko) | 세팔로스포린 항생제의 제조방법 | |
| US5608055A (en) | Beta lactam production | |
| NL8005293A (nl) | Werkwijze voor de bereiding van 6-d-alfa-amino-p- -hydroxyfenylaceetamido penicillaanzuur. | |
| US4299955A (en) | Process for preparing derivatives of 7-amino-desacetoxy cephalosporanic acid | |
| KR20090018892A (ko) | 안정화된 ２-요오도옥시벤조산(ｓｉｂｘ)에 의한 목시덱틴 제조시 유용한 향상된 안전성을 갖는 개선된 산화 방법 | |
| US5142043A (en) | Process for preparing cephalexin monohydrate | |
| RO109652B1 (ro) | Procedeu pentru prepararea unui antibiotic cefepim dihidroclorura hidrat | |
| US3925362A (en) | {60 -Alkylsulfobenzyl penicillins and production thereof | |
| JP3514495B2 (ja) | ハロゲン化アミノチアジアゾリル酢酸誘導体の製造法 | |
| SU1056903A3 (ru) | Способ получени 1-оксадетиацефалоспоринов или их солей | |
| KR830002896B1 (ko) | 세팔로스포린 유도체의 제조방법 | |
| GB2121408A (en) | Tetrazolylalkanohydroxamic acid derivatives | |
| CA1042421A (en) | Process for producting 7-acylamido-7-alkoxycephalosporins | |
| US4231954A (en) | Dane salt and process for preparing aminopenicillins therefrom | |
| KR800001554B1 (ko) | 세펨유도체의 제조방법 | |
| KR800000791B1 (ko) | 세펨유도체의 제조법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |