JPS6113478B2 - - Google Patents
Info
- Publication number
- JPS6113478B2 JPS6113478B2 JP49079044A JP7904474A JPS6113478B2 JP S6113478 B2 JPS6113478 B2 JP S6113478B2 JP 49079044 A JP49079044 A JP 49079044A JP 7904474 A JP7904474 A JP 7904474A JP S6113478 B2 JPS6113478 B2 JP S6113478B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acid
- aminoacetamidocephalosporin
- carboxylic acid
- group
- 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.)
- Expired
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)
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)
| 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)
| 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 FR FR7424795A patent/FR2237635B1/fr not_active Expired
- 1974-07-17 DK DK383974AA patent/DK142144B/da not_active IP Right Cessation
- 1974-07-17 ES ES428386A patent/ES428386A1/es not_active Expired
- 1974-07-17 DD DD179967A patent/DD112134A5/xx unknown
- 1974-07-18 SE SE7409415A patent/SE415765B/xx not_active IP Right Cessation
- 1974-07-18 SU SU742045556A patent/SU622409A3/ru active
- 1974-07-18 AR AR254755A patent/AR211686A1/es active
- 1974-07-18 HU HULI261A patent/HU168065B/hu unknown
- 1974-07-18 PL PL1974172840A patent/PL91364B1/pl unknown
- 1974-07-18 BE BE146673A patent/BE817790A/xx not_active IP Right Cessation
- 1974-07-19 BG BG7400027304A patent/BG25799A3/xx unknown
- 1974-07-19 AT AT597874A patent/AT338972B/de active
- 1974-07-19 RO RO7479536A patent/RO64483A/ro unknown
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