BE517496A - - Google Patents
Info
- Publication number
- BE517496A BE517496A BE517496DA BE517496A BE 517496 A BE517496 A BE 517496A BE 517496D A BE517496D A BE 517496DA BE 517496 A BE517496 A BE 517496A
- Authority
- BE
- Belgium
- Prior art keywords
- penicillin
- salts
- water
- ethyl
- phenyl
- Prior art date
Links
- 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 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 229940049954 penicillin Drugs 0.000 claims description 30
- 229930182555 Penicillin Natural products 0.000 claims description 23
- -1 ester radical Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000002960 penicillins Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical class CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 claims description 6
- 150000003673 urethanes Chemical class 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229940056360 penicillin g Drugs 0.000 description 12
- 159000000000 sodium salts Chemical class 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 11
- 239000000155 melt Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000036765 blood level Effects 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 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 3
- 238000002360 preparation method Methods 0.000 description 3
- MSMJEQQYVMQBSR-UHFFFAOYSA-N (4-hydroxyphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(O)C=C1 MSMJEQQYVMQBSR-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000012928 buffer substance Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FTCSYRJOUNYMJL-UHFFFAOYSA-N (4-ethoxyphenyl)carbamic acid Chemical compound CCOC1=CC=C(NC(O)=O)C=C1 FTCSYRJOUNYMJL-UHFFFAOYSA-N 0.000 description 1
- CFPIUEJWNMSDRG-UHFFFAOYSA-N 1-[benzyl(butyl)amino]ethanol Chemical compound C(CCC)N(CC1=CC=CC=C1)C(C)O CFPIUEJWNMSDRG-UHFFFAOYSA-N 0.000 description 1
- IEQJDMSYHNQTRH-UHFFFAOYSA-N 1-[benzyl(propyl)amino]ethanol Chemical compound CCCN(C(C)O)CC1=CC=CC=C1 IEQJDMSYHNQTRH-UHFFFAOYSA-N 0.000 description 1
- DZCBKUAAGVVLOX-UHFFFAOYSA-N 1-morpholin-4-ylethanol Chemical compound CC(O)N1CCOCC1 DZCBKUAAGVVLOX-UHFFFAOYSA-N 0.000 description 1
- MSSFHHSZGOKYJS-UHFFFAOYSA-N 2-(butylamino)ethyl N-phenylcarbamate Chemical compound CCCCNCCOC(=O)NC1=CC=CC=C1 MSSFHHSZGOKYJS-UHFFFAOYSA-N 0.000 description 1
- ICMRDYSEHFJJAT-UHFFFAOYSA-N 2-(cyclohexylamino)ethyl n-phenylcarbamate;hydrochloride Chemical compound [Cl-].C1CCCCC1[NH2+]CCOC(=O)NC1=CC=CC=C1 ICMRDYSEHFJJAT-UHFFFAOYSA-N 0.000 description 1
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 239000004107 Penicillin G sodium Substances 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000019369 penicillin G sodium Nutrition 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 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)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE517496A true BE517496A (cs) |
Family
ID=154379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE517496D BE517496A (cs) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE517496A (cs) |
-
0
- BE BE517496D patent/BE517496A/fr unknown
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