NO129909B - - Google Patents
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- Publication number
- NO129909B NO129909B NO15474364A NO15474364A NO129909B NO 129909 B NO129909 B NO 129909B NO 15474364 A NO15474364 A NO 15474364A NO 15474364 A NO15474364 A NO 15474364A NO 129909 B NO129909 B NO 129909B
- Authority
- NO
- Norway
- Prior art keywords
- acyl
- acid
- aps
- saccharin
- residue
- Prior art date
Links
- 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 11
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 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 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229930182555 Penicillin Natural products 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 229940049954 penicillin Drugs 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002960 penicillins Chemical class 0.000 description 3
- HEKURBKACCBNEJ-UHFFFAOYSA-M potassium;1,1-dioxo-1,2-benzothiazol-2-id-3-one Chemical compound [K+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 HEKURBKACCBNEJ-UHFFFAOYSA-M 0.000 description 3
- 229940081974 saccharin Drugs 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- -1 α-phenoxypropionyl-saccharin Chemical compound 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- CMWPBGIBHBCVSW-UHFFFAOYSA-N 2-phenoxybutanoyl chloride Chemical compound CCC(C(Cl)=O)OC1=CC=CC=C1 CMWPBGIBHBCVSW-UHFFFAOYSA-N 0.000 description 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0040759 | 1963-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129909B true NO129909B (fi) | 1974-06-10 |
Family
ID=7098378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15474364A NO129909B (fi) | 1963-09-14 | 1964-09-12 |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT259134B (fi) |
| BR (1) | BR6462546D0 (fi) |
| DE (1) | DE1745619B1 (fi) |
| DK (1) | DK131288B (fi) |
| FI (1) | FI46730C (fi) |
| GB (1) | GB1024809A (fi) |
| NL (1) | NL141514B (fi) |
| NO (1) | NO129909B (fi) |
| SE (1) | SE309041B (fi) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1317566A (fi) * | 1963-05-08 | |||
| FR61E (fr) * | 1901-08-21 | 1902-10-13 | Basf Ag | Production de colorants azoiques, susceptibles d'etre chromés sur la fibre |
| DE1146061C2 (de) * | 1958-07-31 | 1977-09-01 | Beecham-Group Limited, Brentford, Middlesex (Großbritannien) | Verfahren zur herstellung von derivaten der 6-aminopenicillansaeure |
| DE1149361B (de) * | 1959-09-24 | 1963-05-30 | Bayer Ag | Verfahren zur Herstellung von 6-Acylaminopenicillansaeuren auf enzymatischem Wege |
| DE1151803B (de) * | 1959-12-04 | 1963-07-25 | Bayer Ag | Verfahren zur Herstellung von 6-Acylaminopenicillansaeuren |
| US3161634A (en) * | 1960-12-21 | 1964-12-15 | Novo Terapeutisk Labor As | Process of making nu-acyl derivatives of 6-amino-penicillanic acid |
| US3094519A (en) * | 1961-01-16 | 1963-06-18 | Bristol Myers Co | Process for the preparation of derivatives of 6-amino-penicillanic acid |
| BE639104A (fi) * | 1962-11-02 |
-
1963
- 1963-09-14 DE DE19631745619 patent/DE1745619B1/de not_active Ceased
-
1964
- 1964-09-02 FI FI185564A patent/FI46730C/fi active
- 1964-09-08 NL NL6410449A patent/NL141514B/xx unknown
- 1964-09-11 DK DK450664A patent/DK131288B/da unknown
- 1964-09-11 BR BR16254664A patent/BR6462546D0/pt unknown
- 1964-09-12 NO NO15474364A patent/NO129909B/no unknown
- 1964-09-14 GB GB3743664A patent/GB1024809A/en not_active Expired
- 1964-09-14 AT AT786264A patent/AT259134B/de active
- 1964-09-14 SE SE1102264A patent/SE309041B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK131288C (fi) | 1975-11-17 |
| FI46730B (fi) | 1973-02-28 |
| DE1745619B1 (de) | 1969-09-11 |
| AT259134B (de) | 1967-12-27 |
| GB1024809A (en) | 1966-04-06 |
| NL141514B (nl) | 1974-03-15 |
| NL6410449A (fi) | 1965-03-15 |
| DK131288B (da) | 1975-06-23 |
| SE309041B (fi) | 1969-03-10 |
| BR6462546D0 (pt) | 1973-08-07 |
| FI46730C (fi) | 1973-06-11 |
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