JPS6113478B2 - - Google Patents

Info

Publication number: JPS6113478B2
Authority: JP; Japan
Prior art keywords: compound; acid; aminoacetamidocephalosporin; carboxylic acid; group
Prior art date: 1973-07-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP49079044A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5040588A (nl

Inventor

Dauison Maikeru

Binfuiirudo Furankuhamu Deeuitsudo

Uiriamu Machesu Supensu Toomasu

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.)

Lilly Industries Ltd

Original Assignee

Lilly Industries Ltd

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.)

1973-07-19

Filing date

1974-07-10

Publication date

1986-04-14

1974-07-10 Application filed by Lilly Industries Ltd filed Critical Lilly Industries Ltd

1975-04-14 Publication of JPS5040588A publication Critical patent/JPS5040588A/ja

1986-04-14 Publication of JPS6113478B2 publication Critical patent/JPS6113478B2/ja

Status Expired legal-status Critical Current

Links

-1 dicarbonyl compound Chemical class 0.000 claims description 22
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
229930186147 Cephalosporin Natural products 0.000 claims description 11
229940124587 cephalosporin Drugs 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
150000002081 enamines Chemical class 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound 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 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 16
229940106164 cephalexin Drugs 0.000 description 16
238000000034 method Methods 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
150000001780 cephalosporins Chemical class 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
230000007423 decrease Effects 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
239000012535 impurity Substances 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
125000004149 thio group Chemical group *S* 0.000 description 4
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 3
UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000010933 acylation Effects 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000006242 amine protecting group Chemical group 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
125000006244 carboxylic acid protecting group Chemical group 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
125000001240 enamine group Chemical group 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 2
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000007257 deesterification reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical group NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical class COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
FMONNRDZPPUEOZ-GFCCVEGCSA-N (2r)-2-[(4-methoxy-4-oxobut-2-en-2-yl)amino]-2-phenylacetic acid Chemical compound COC(=O)C=C(C)N[C@@H](C(O)=O)C1=CC=CC=C1 FMONNRDZPPUEOZ-GFCCVEGCSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
JBJJTCGQCRGNOL-UHFFFAOYSA-N 2-azaniumyl-2-cyclohexa-1,4-dien-1-ylacetate Chemical compound OC(=O)C(N)C1=CCC=CC1 JBJJTCGQCRGNOL-UHFFFAOYSA-N 0.000 description 1
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
229960002588 cefradine Drugs 0.000 description 1
RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004989 dicarbonyl group Chemical group 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
VWAWMPXOFHGGMY-UTONKHPSSA-M sodium;(2r)-2-[(4-methoxy-4-oxobut-2-en-2-yl)amino]-2-phenylacetate Chemical compound [Na+].COC(=O)C=C(C)N[C@@H](C([O-])=O)C1=CC=CC=C1 VWAWMPXOFHGGMY-UTONKHPSSA-M 0.000 description 1
XWLVFYWUQZTUCK-OGFXRTJISA-M sodium;(2r)-2-amino-2-phenylacetate Chemical compound [Na+].[O-]C(=O)[C@H](N)C1=CC=CC=C1 XWLVFYWUQZTUCK-OGFXRTJISA-M 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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)
Cephalosporin Compounds (AREA)

JP49079044A 1973-07-19 1974-07-10 Expired JPS6113478B2 (nl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3433773A GB1473090A (nl)	1973-07-19	1973-07-19

Publications (2)

Publication Number	Publication Date
JPS5040588A JPS5040588A (nl)	1975-04-14
JPS6113478B2 true JPS6113478B2 (nl)	1986-04-14

Family

ID=10364389

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP49079044A Expired JPS6113478B2 (nl)	1973-07-19	1974-07-10

Country Status (25)

Country	Link
JP (1)	JPS6113478B2 (nl)
AR (1)	AR211686A1 (nl)
AT (1)	AT338972B (nl)
BE (1)	BE817790A (nl)
BG (1)	BG25799A3 (nl)
CA (1)	CA1024508A (nl)
CH (1)	CH582189A5 (nl)
CS (1)	CS188188B2 (nl)
DD (1)	DD112134A5 (nl)
DE (1)	DE2434017C3 (nl)
DK (1)	DK142144B (nl)
ES (1)	ES428386A1 (nl)
FR (1)	FR2237635B1 (nl)
GB (1)	GB1473090A (nl)
HU (1)	HU168065B (nl)
IE (1)	IE39506B1 (nl)
IL (1)	IL45101A (nl)
NL (1)	NL187811C (nl)
PH (1)	PH11147A (nl)
PL (1)	PL91364B1 (nl)
RO (1)	RO64483A (nl)
SE (1)	SE415765B (nl)
SU (1)	SU622409A3 (nl)
YU (1)	YU182574A (nl)
ZA (1)	ZA743890B (nl)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1126544B (it) *	1979-12-07	1986-05-21	Dobfar Spa	Procedimento per la preparazione di derivati dell'acido 7-amino-desacetossi cefalosporanico

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1602620A (en) *	1965-03-08	1971-01-04		Antibacterial cephalosporin cpds

1973
- 1973-07-19 GB GB3433773A patent/GB1473090A/en not_active Expired
1974
- 1974-06-17 IE IE1263/74A patent/IE39506B1/xx unknown
- 1974-06-18 ZA ZA00743890A patent/ZA743890B/xx unknown
- 1974-06-18 CA CA202,732A patent/CA1024508A/en not_active Expired
- 1974-06-21 IL IL45101A patent/IL45101A/en unknown
- 1974-06-28 YU YU01825/74A patent/YU182574A/xx unknown
- 1974-07-05 PH PH16018A patent/PH11147A/en unknown
- 1974-07-10 NL NLAANVRAGE7409299,A patent/NL187811C/nl not_active IP Right Cessation
- 1974-07-10 JP JP49079044A patent/JPS6113478B2/ja not_active Expired
- 1974-07-10 CS CS744896A patent/CS188188B2/cs unknown
- 1974-07-10 CH CH948774A patent/CH582189A5/xx not_active IP Right Cessation
- 1974-07-16 DE DE2434017A patent/DE2434017C3/de not_active Expired
- 1974-07-17 ES ES428386A patent/ES428386A1/es not_active Expired
- 1974-07-17 DK DK383974AA patent/DK142144B/da not_active IP Right Cessation
- 1974-07-17 DD DD179967A patent/DD112134A5/xx unknown
- 1974-07-17 FR FR7424795A patent/FR2237635B1/fr not_active Expired
- 1974-07-18 BE BE146673A patent/BE817790A/xx not_active IP Right Cessation
- 1974-07-18 SU SU742045556A patent/SU622409A3/ru active
- 1974-07-18 SE SE7409415A patent/SE415765B/xx not_active IP Right Cessation
- 1974-07-18 HU HULI261A patent/HU168065B/hu unknown
- 1974-07-18 PL PL1974172840A patent/PL91364B1/pl unknown
- 1974-07-18 AR AR254755A patent/AR211686A1/es active
- 1974-07-19 BG BG027304A patent/BG25799A3/xx unknown
- 1974-07-19 RO RO7479536A patent/RO64483A/ro unknown
- 1974-07-19 AT AT597874A patent/AT338972B/de active

Also Published As

Publication number	Publication date
IL45101A (en)	1977-01-31
CS188188B2 (en)	1979-02-28
IE39506B1 (en)	1978-10-25
AR211686A1 (es)	1978-02-28
RO64483A (fr)	1979-08-15
SE415765B (sv)	1980-10-27
DD112134A5 (nl)	1975-03-20
ES428386A1 (es)	1976-07-16
SU622409A3 (ru)	1978-08-30
NL187811B (nl)	1991-08-16
PL91364B1 (nl)	1977-02-28
NL187811C (nl)	1992-01-16
FR2237635B1 (nl)	1978-07-21
DE2434017A1 (de)	1975-02-06
HU168065B (nl)	1976-02-28
SE7409415L (nl)	1975-01-20
JPS5040588A (nl)	1975-04-14
GB1473090A (nl)	1977-05-11
YU182574A (en)	1982-05-31
CH582189A5 (nl)	1976-11-30
DK383974A (nl)	1975-03-17
NL7409299A (nl)	1975-01-21
AU7056574A (en)	1976-01-08
FR2237635A1 (nl)	1975-02-14
DK142144C (nl)	1981-02-09
DE2434017C3 (de)	1980-04-17
DE2434017B2 (de)	1979-08-02
ATA597874A (de)	1977-01-15
IL45101A0 (en)	1974-09-10
AT338972B (de)	1977-09-26
DK142144B (da)	1980-09-08
ZA743890B (en)	1976-01-28
PH11147A (en)	1977-10-27
BG25799A3 (en)	1978-12-12
CA1024508A (en)	1978-01-17
BE817790A (fr)	1975-01-20
IE39506L (en)	1975-01-19

Publication	Publication Date	Title
JP2005521634A (ja)	2005-07-21	レパグリニドの製法
JPS6027677B2 (ja)	1985-06-29	７−置換又は非置換アミノ−３−置換チオメチルセフエムカルボン酸類の新規製造法
AU658761B2 (en)	1995-04-27	A method for the acylation of the 7-amino group of the cephalosporanic ring
US3632850A (en)	1972-01-04	Cephalexin synthesis
JPS59130889A (ja)	1984-07-27	新規なセフアロスポリン中間体
US4708825A (en)	1987-11-24	Process for the production of penicillins
JP2505981B2 (ja)	1996-06-12	新規なチア（ジア）ゾル酢酸の反応性チオホスフェ―ト誘導体及びその製造方法
EP0986565B1 (en)	2009-01-14	Improved precipitation process of 7-aminocephalosporanic acid (7-aca)
JPS6113478B2 (nl)	1986-04-14
CN1298408A (zh)	2001-06-06	结晶β－内酰胺抗生素的方法
US3946002A (en)	1976-03-23	Process for preparing cephalosporins
JP2001294590A (ja)	2001-10-23	３−ビニル−セフェム化合物の製造方法
JPS6135199B2 (nl)	1986-08-12
KR790001872B1 (ko)	1979-12-27	세팔로스포린의 제조방법
JPH02167289A (ja)	1990-06-27	新規セフアロスポリン誘導体の製法
US3853861A (en)	1974-12-10	Cephalexin intermediate
US5162522A (en)	1992-11-10	Method for producing cephem compounds
US4304909A (en)	1981-12-08	Process for producing 7-(D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl)acetamido)-3-(5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl)-.DELTA.3 -cephem-4-carboxylic acid and a pharmaceutically acceptable salt thereof
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