DK142367B - 7-Acylamidocephalosporanderivater til anvendelse som mellemprodukter ved fremstilling af 7-aminocephalosporansyre eller derivater deraf, samt fremgangsmåde til fremstilling deraf. - Google Patents
7-Acylamidocephalosporanderivater til anvendelse som mellemprodukter ved fremstilling af 7-aminocephalosporansyre eller derivater deraf, samt fremgangsmåde til fremstilling deraf. Download PDFInfo
- Publication number
- DK142367B DK142367B DK415069AA DK415069A DK142367B DK 142367 B DK142367 B DK 142367B DK 415069A A DK415069A A DK 415069AA DK 415069 A DK415069 A DK 415069A DK 142367 B DK142367 B DK 142367B
- Authority
- DK
- Denmark
- Prior art keywords
- derivatives
- cephalosporin
- amino acid
- preparation
- acid oxidase
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 16
- 239000002253 acid Substances 0.000 title claims description 6
- 239000000543 intermediate Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 20
- 102000004674 D-amino-acid oxidase Human genes 0.000 claims description 18
- 108010003989 D-amino-acid oxidase Proteins 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- -1 cephalosporin compound Chemical class 0.000 claims description 16
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- 108010053835 Catalase Proteins 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 229930186147 Cephalosporin Natural products 0.000 claims description 10
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- 230000002538 fungal effect Effects 0.000 claims description 5
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- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 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 51
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- 239000000284 extract Substances 0.000 description 18
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
- 102000004190 Enzymes Human genes 0.000 description 15
- 108090000790 Enzymes Proteins 0.000 description 15
- 229940088598 enzyme Drugs 0.000 description 15
- 238000000855 fermentation Methods 0.000 description 15
- 230000004151 fermentation Effects 0.000 description 15
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- 239000007788 liquid Substances 0.000 description 14
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- 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 description 9
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- 229940048086 sodium pyrophosphate Drugs 0.000 description 7
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- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- WVVOBOZHTQJXPB-UHFFFAOYSA-N N-anilino-N-nitronitramide Chemical compound [N+](=O)([O-])N(NC1=CC=CC=C1)[N+](=O)[O-] WVVOBOZHTQJXPB-UHFFFAOYSA-N 0.000 description 1
- 241000221960 Neurospora Species 0.000 description 1
- 239000004157 Nitrosyl chloride Substances 0.000 description 1
- 108090000526 Papain Proteins 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000228150 Penicillium chrysogenum Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- PIXDPLMASMRKFC-UHFFFAOYSA-N [N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[Na+].[Na+].[Na+] Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[Na+].[Na+].[Na+] PIXDPLMASMRKFC-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HYGWNUKOUCZBND-UHFFFAOYSA-N azanide Chemical compound [NH2-] HYGWNUKOUCZBND-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
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- 238000011088 calibration curve Methods 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
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- 229920002678 cellulose Polymers 0.000 description 1
- 150000001782 cephems Chemical class 0.000 description 1
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- 238000005947 deacylation reaction Methods 0.000 description 1
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- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 229950010030 dl-alanine Drugs 0.000 description 1
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- 239000001963 growth medium Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
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- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
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- 229940055729 papain Drugs 0.000 description 1
- 235000019834 papain Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
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- MPSUGQWRVNRJEE-UHFFFAOYSA-N triazol-1-amine Chemical compound NN1C=CN=N1 MPSUGQWRVNRJEE-UHFFFAOYSA-N 0.000 description 1
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- 230000003442 weekly effect Effects 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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3711368 | 1968-08-02 | ||
| GB37113/68A GB1272769A (en) | 1968-08-02 | 1968-08-02 | Improvements in or relating to cephalosporin derivatives |
| GB3711369 | 1969-07-18 | ||
| GB3711369 | 1969-07-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK142367B true DK142367B (da) | 1980-10-20 |
| DK142367C DK142367C (ja) | 1981-03-09 |
Family
ID=26263338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK415069AA DK142367B (da) | 1968-08-02 | 1969-08-01 | 7-Acylamidocephalosporanderivater til anvendelse som mellemprodukter ved fremstilling af 7-aminocephalosporansyre eller derivater deraf, samt fremgangsmåde til fremstilling deraf. |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS507158B1 (ja) |
| DK (1) | DK142367B (ja) |
| SE (1) | SE392105B (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK153554B (da) * | 1975-01-22 | 1988-07-25 | Asahi Chemical Ind | Fremgangsmaade til fremstilling af 7-aminocephalosporansyrederivater |
-
1969
- 1969-08-01 SE SE6910822A patent/SE392105B/xx unknown
- 1969-08-01 JP JP44060469A patent/JPS507158B1/ja active Pending
- 1969-08-01 DK DK415069AA patent/DK142367B/da not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK153554B (da) * | 1975-01-22 | 1988-07-25 | Asahi Chemical Ind | Fremgangsmaade til fremstilling af 7-aminocephalosporansyrederivater |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS507158B1 (ja) | 1975-03-22 |
| DK142367C (ja) | 1981-03-09 |
| SE392105B (sv) | 1977-03-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |