FI66617C - Foerfarande foer framstaellning av 6-aminopenicillansyra 7-aminocefalosporansyra och dess derivat i 3-staeaeningen - Google Patents

Foerfarande foer framstaellning av 6-aminopenicillansyra 7-aminocefalosporansyra och dess derivat i 3-staeaeningen Download PDF

Info

Publication number: FI66617C
Authority: FI; Finland
Prior art keywords: group; acid; cephalosporin; imino; substrate
Prior art date: 1974-08-07

Application number

FI752191A

Other languages

English (en)

Finnish (fi)

Other versions

FI66617B (fi

FI752191A (no

Inventor

Ernesto Oppici

Anacleto Gianantonio

Original Assignee

Lepetit Spa

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.)

1974-08-07

Filing date

1975-07-31

Publication date

1984-11-12

1975-07-31 Application filed by Lepetit Spa filed Critical Lepetit Spa

1976-02-08 Publication of FI752191A publication Critical patent/FI752191A/fi

1984-07-31 Application granted granted Critical

1984-07-31 Publication of FI66617B publication Critical patent/FI66617B/fi

1984-11-12 Publication of FI66617C publication Critical patent/FI66617C/fi

Links

238000000034 method Methods 0.000 claims description 29
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
-1 imino halide Chemical class 0.000 claims description 21
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims description 19
239000000758 substrate Substances 0.000 claims description 17
229940124587 cephalosporin Drugs 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 16
229930186147 Cephalosporin Natural products 0.000 claims description 15
150000001780 cephalosporins Chemical class 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 12
229930182555 Penicillin Natural products 0.000 claims description 11
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 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 8
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 7
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229940049954 penicillin Drugs 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000003460 beta-lactamyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000003368 amide group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000003776 cleavage reaction Methods 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052751 metal Chemical group 0.000 claims description 2
239000002184 metal Chemical group 0.000 claims description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
150000007530 organic bases Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 20
HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 6
150000002960 penicillins Chemical class 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000003755 preservative agent Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 4
230000002140 halogenating effect Effects 0.000 description 4
230000002335 preservative effect Effects 0.000 description 4
239000003223 protective agent Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000002516 radical scavenger Substances 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000251730 Chondrichthyes Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002463 imidates Chemical class 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
230000002000 scavenging effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
OTLNPYWUJOZPPA-UHFFFAOYSA-M 4-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-M 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
238000007429 general method Methods 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
150000002485 inorganic esters Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
TVMXJQZBKOMFQK-OOARYINLSA-L zinc;(6r,7r)-3-(acetyloxymethyl)-7-[[(5r)-5-amino-5-carboxylatopentanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Zn+2].S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C([O-])=O)[C@@H]12 TVMXJQZBKOMFQK-OOARYINLSA-L 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
- 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
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

FI752191A 1974-08-07 1975-07-31 Foerfarande foer framstaellning av 6-aminopenicillansyra 7-aminocefalosporansyra och dess derivat i 3-staeaeningen FI66617C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB3475474		1974-08-07
GB3475474A GB1467355A (en)	1974-08-07	1974-08-07	Preparation of 6-aminopenicillanic acid 7-aminocephalospo ranic acid and derivatives thereof

Publications (3)

Publication Number	Publication Date
FI752191A FI752191A (no)	1976-02-08
FI66617B FI66617B (fi)	1984-07-31
FI66617C true FI66617C (fi)	1984-11-12

Family

ID=10369564

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI752191A FI66617C (fi)	1974-08-07	1975-07-31	Foerfarande foer framstaellning av 6-aminopenicillansyra 7-aminocefalosporansyra och dess derivat i 3-staeaeningen

Country Status (20)

Country	Link
US (1)	US4021426A (no)
JP (1)	JPS5141384A (no)
BE (1)	BE832218A (no)
BR (1)	BR7505032A (no)
CA (1)	CA1045115A (no)
CS (1)	CS183813B2 (no)
DD (1)	DD120445A5 (no)
DE (1)	DE2534337C2 (no)
DK (1)	DK357575A (no)
FI (1)	FI66617C (no)
FR (1)	FR2281367A1 (no)
GB (1)	GB1467355A (no)
HU (1)	HU170295B (no)
IL (1)	IL47868A (no)
NL (1)	NL180218C (no)
NO (1)	NO151747C (no)
SE (1)	SE433217B (no)
SU (1)	SU597339A3 (no)
YU (1)	YU192275A (no)
ZA (1)	ZA754609B (no)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS52124438A (en) *	1976-04-14	1977-10-19	Nitsutou Aen Metsuki Kk	Device for hot dipping long rod material
NL7908867A (nl) *	1979-12-10	1981-07-01	Gist Brocades Nv	Werkwijze voor het bereiden van 6-aminopenicillaanzuur- -1,1-dioxide en zijn zouten.
ATE31535T1 (de) *	1981-07-17	1988-01-15	Glaxo Group Ltd	Cephalosporinverbindungen.
JPH0586220U (ja) *	1991-04-05	1993-11-22	道夫山中	傘の止め紐
JPH07210079A (ja) *	1994-01-22	1995-08-11	Mitsuo Yoshizawa	幾つかの置換及びそれらの合成を表す教具兼知育玩具

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2062925A1 (en) *	1969-12-26	1971-07-01	President Of Osaka University, Osaka (Japan)	6-aminopenicillanic acid prepn
JPS5035079B1 (no) *	1970-10-17	1975-11-13
BE787618A (fr) *	1971-08-17	1973-02-16	Gist Brocades Nv	Procede pour preparer des composes heterocycliques

1974
- 1974-08-07 GB GB3475474A patent/GB1467355A/en not_active Expired
1975
- 1975-07-17 ZA ZA00754609A patent/ZA754609B/xx unknown
- 1975-07-17 US US05/596,699 patent/US4021426A/en not_active Expired - Lifetime
- 1975-07-28 YU YU01922/75A patent/YU192275A/xx unknown
- 1975-07-31 FI FI752191A patent/FI66617C/fi not_active IP Right Cessation
- 1975-08-01 DE DE2534337A patent/DE2534337C2/de not_active Expired
- 1975-08-04 IL IL47868A patent/IL47868A/xx unknown
- 1975-08-04 CS CS7500005430A patent/CS183813B2/cs unknown
- 1975-08-05 NO NO752748A patent/NO151747C/no unknown
- 1975-08-06 BR BR7505032A patent/BR7505032A/pt unknown
- 1975-08-06 DK DK357575A patent/DK357575A/da not_active Application Discontinuation
- 1975-08-06 JP JP50095710A patent/JPS5141384A/ja active Granted
- 1975-08-06 DD DD187715A patent/DD120445A5/xx unknown
- 1975-08-06 HU HULE777A patent/HU170295B/hu unknown
- 1975-08-06 SE SE7508880A patent/SE433217B/xx not_active IP Right Cessation
- 1975-08-06 CA CA232,939A patent/CA1045115A/en not_active Expired
- 1975-08-06 NL NLAANVRAGE7509348,A patent/NL180218C/xx not_active IP Right Cessation
- 1975-08-07 BE BE159019A patent/BE832218A/xx not_active IP Right Cessation
- 1975-08-07 FR FR7524699A patent/FR2281367A1/fr active Granted
- 1975-08-07 SU SU752163058A patent/SU597339A3/ru active

Also Published As

Publication number	Publication date
FR2281367B1 (no)	1977-12-16
YU192275A (en)	1982-05-31
BE832218A (fr)	1975-12-01
SU597339A3 (ru)	1978-03-05
DE2534337C2 (de)	1986-05-07
ZA754609B (en)	1976-07-28
NL180218B (nl)	1986-08-18
NL180218C (nl)	1987-01-16
GB1467355A (en)	1977-03-16
NO151747B (no)	1985-02-18
BR7505032A (pt)	1976-08-31
IL47868A (en)	1978-03-10
SE433217B (sv)	1984-05-14
CA1045115A (en)	1978-12-26
FR2281367A1 (fr)	1976-03-05
FI66617B (fi)	1984-07-31
NO752748L (no)	1976-02-10
SE7508880L (sv)	1976-02-09
JPS5141384A (en)	1976-04-07
NL7509348A (nl)	1976-02-10
US4021426A (en)	1977-05-03
HU170295B (no)	1977-05-28
CS183813B2 (en)	1978-07-31
IL47868A0 (en)	1975-11-25
DK357575A (da)	1976-02-08
DE2534337A1 (de)	1976-02-19
DD120445A5 (no)	1976-06-12
JPS6131113B2 (no)	1986-07-17
FI752191A (no)	1976-02-08
NO151747C (no)	1985-06-05

Publication	Publication Date	Title
FI66617C (fi)	1984-11-12	Foerfarande foer framstaellning av 6-aminopenicillansyra 7-aminocefalosporansyra och dess derivat i 3-staeaeningen
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KR20010045748A (ko)	2001-06-05	고순도 세프포독심 프록세틸의 제조방법
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CA1339312C (en)	1997-08-19	Process for the manufacture of carboxylic acid amides
EP0397212B1 (en)	1996-01-10	Process for preparing cephalosporin compounds
FI66186B (fi)	1984-05-31	Foerfarande foer framstaellning av penicillansyra- och cefalosporansyraderivat
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JP2595605B2 (ja)	1997-04-02	２−置換オキシイミノ−３−オキソ酪酸の製造法
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EP0300657B1 (en)	1993-03-31	4-substituted 3-oxobutanoate ester derivatives
JPS6135199B2 (no)	1986-08-12
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US4376200A (en)	1983-03-08	Heterocyclic thiomethylation of the 3-position of 7-aminocephalosporanic acids
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US5552542A (en)	1996-09-03	Preparation and use of 7-[(2-carboalkoxy-1-methylethenyl)amino]-3-hydroxymethyl-3-cephem-4-carboxylic acids
US4301072A (en)	1981-11-17	Process for preparing aminopenicillins
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US3946002A (en)	1976-03-23	Process for preparing cephalosporins
US4231954A (en)	1980-11-04	Dane salt and process for preparing aminopenicillins therefrom
KR790001872B1 (ko)	1979-12-27	세팔로스포린의 제조방법
FI62833C (fi)	1983-03-10	Som mellanprodukter vid framstaellning av antibakteriella penicillin- och cefalosporinderivat anvaendbara 2,3-dioxopiperazinderivat och foerfarande foer framstaellning av dem
JP4659959B2 (ja)	2011-03-30	３−セフェム化合物及びその製造法

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2004-08-31	MM	Patent lapsed	Owner name: GRUPPO LEPETIT S.P.A.