BE549328A - - Google Patents
Info
- Publication number
- BE549328A BE549328A BE549328DA BE549328A BE 549328 A BE549328 A BE 549328A BE 549328D A BE549328D A BE 549328DA BE 549328 A BE549328 A BE 549328A
- Authority
- BE
- Belgium
- Prior art keywords
- bis
- methyl
- benzene
- penicillin
- benzylamino
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 17
- 229930182555 Penicillin Natural products 0.000 claims description 16
- 150000002960 penicillins Chemical class 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- -1 cyclic radical Chemical class 0.000 description 17
- 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 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 229940049954 penicillin Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229940056360 penicillin g Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229930195708 Penicillin V Natural products 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229940056367 penicillin v Drugs 0.000 description 3
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- PSMQNQWPTFFHIR-UHFFFAOYSA-N n-[[4-[(benzylamino)methyl]phenyl]methyl]-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CNCC(C=C1)=CC=C1CNCC1=CC=CC=C1 PSMQNQWPTFFHIR-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- BAVMXDNHWGQCSR-UHFFFAOYSA-N 1-[2-(2,3-dimethylphenyl)ethyl]-2,3-dimethylbenzene Chemical group CC1=CC=CC(CCC=2C(=C(C)C=CC=2)C)=C1C BAVMXDNHWGQCSR-UHFFFAOYSA-N 0.000 description 1
- STPLGCRETYJDSU-UHFFFAOYSA-N 1-[4-(1-amino-3-phenylpropyl)phenyl]-3-phenylpropan-1-amine Chemical compound C=1C=C(C(N)CCC=2C=CC=CC=2)C=CC=1C(N)CCC1=CC=CC=C1 STPLGCRETYJDSU-UHFFFAOYSA-N 0.000 description 1
- QHMGOVRVVGBUIK-UHFFFAOYSA-N 1-cyclohexyl-N-[[4-[(cyclohexylmethylamino)methyl]phenyl]methyl]methanamine Chemical compound C(NCc1ccc(CNCC2CCCCC2)cc1)C1CCCCC1 QHMGOVRVVGBUIK-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HVXURUHRMFCCHO-UHFFFAOYSA-N C(C1=CC=CC=C1)NCC1=NC=C(C=C1)CNCC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)NCC1=NC=C(C=C1)CNCC1=CC=CC=C1 HVXURUHRMFCCHO-UHFFFAOYSA-N 0.000 description 1
- ZGWGAMQJCZGAAN-UHFFFAOYSA-N C(C1=CC=CC=C1)NCC1=NC=CC=C1CNCC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)NCC1=NC=CC=C1CNCC1=CC=CC=C1 ZGWGAMQJCZGAAN-UHFFFAOYSA-N 0.000 description 1
- ZUNWEGCGRGHLMM-UHFFFAOYSA-N C(C1=CC=CC=C1)NCC=1C=NC=C(C=1)CNCC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)NCC=1C=NC=C(C=1)CNCC1=CC=CC=C1 ZUNWEGCGRGHLMM-UHFFFAOYSA-N 0.000 description 1
- DTPXVUBYGXKTED-UHFFFAOYSA-N COC1=CC=C(CNCC2=CC=C(C=C2)CNCC2=CC=C(C=C2)OC)C=C1 Chemical compound COC1=CC=C(CNCC2=CC=C(C=C2)CNCC2=CC=C(C=C2)OC)C=C1 DTPXVUBYGXKTED-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- ILYSEJOMOSGTHX-UHFFFAOYSA-N N-benzyl-2-[2-[2-(benzylamino)ethyl]phenyl]ethanamine Chemical compound C(C1=CC=CC=C1)NCCC1=C(C=CC=C1)CCNCC1=CC=CC=C1 ILYSEJOMOSGTHX-UHFFFAOYSA-N 0.000 description 1
- 229910003202 NH4 Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QRLCJUNAKLMRGP-UHFFFAOYSA-N Penicillin F Natural products S1C(C)(C)C(C(O)=O)N2C(=O)C(NC(=O)CC=CCC)C21 QRLCJUNAKLMRGP-UHFFFAOYSA-N 0.000 description 1
- QRLCJUNAKLMRGP-ZTWGYATJSA-N Penicillin F Chemical compound S1C(C)(C)[C@H](C(O)=O)N2C(=O)[C@@H](NC(=O)C/C=C/CC)[C@H]21 QRLCJUNAKLMRGP-ZTWGYATJSA-N 0.000 description 1
- AZCVBVRUYHKWHU-MBNYWOFBSA-N Penicillin X Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=C(O)C=C1 AZCVBVRUYHKWHU-MBNYWOFBSA-N 0.000 description 1
- ZSTKQVUYUFADTO-UHFFFAOYSA-N [Cl-].C(C1=CC=CC=C1)[NH2+]CC1=CC=C(C=C1)C[NH2+]CC1=CC=CC=C1.[Cl-] Chemical compound [Cl-].C(C1=CC=CC=C1)[NH2+]CC1=CC=C(C=C1)C[NH2+]CC1=CC=CC=C1.[Cl-] ZSTKQVUYUFADTO-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WDTGNYDDCJERKR-UHFFFAOYSA-N n-(furan-2-ylmethyl)-1-phenylmethanamine Chemical compound C=1C=COC=1CNCC1=CC=CC=C1 WDTGNYDDCJERKR-UHFFFAOYSA-N 0.000 description 1
- OWQVCMBDPJHIRG-UHFFFAOYSA-N n-[[3-[(benzylamino)methyl]phenyl]methyl]-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CNCC(C=1)=CC=CC=1CNCC1=CC=CC=C1 OWQVCMBDPJHIRG-UHFFFAOYSA-N 0.000 description 1
- RWUYDUOERYIKNW-UHFFFAOYSA-N n-[[3-[(cyclohexylamino)methyl]phenyl]methyl]cyclohexanamine Chemical compound C=1C=CC(CNC2CCCCC2)=CC=1CNC1CCCCC1 RWUYDUOERYIKNW-UHFFFAOYSA-N 0.000 description 1
- GQRIZKNDWBCPBL-UHFFFAOYSA-N n-[[5-[(benzylamino)methyl]thiophen-2-yl]methyl]-1-phenylmethanamine Chemical compound C=1C=C(CNCC=2C=CC=CC=2)SC=1CNCC1=CC=CC=C1 GQRIZKNDWBCPBL-UHFFFAOYSA-N 0.000 description 1
- JWHYMGGPFYBULZ-UHFFFAOYSA-N n-[[6-[(benzylamino)methyl]pyridin-2-yl]methyl]-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CNCC(N=1)=CC=CC=1CNCC1=CC=CC=C1 JWHYMGGPFYBULZ-UHFFFAOYSA-N 0.000 description 1
- VFBOEXXXPSQBJS-UHFFFAOYSA-N n-benzyl-2-[3-[2-(benzylamino)ethyl]phenyl]ethanamine Chemical compound C=1C=CC=CC=1CNCCC(C=1)=CC=CC=1CCNCC1=CC=CC=C1 VFBOEXXXPSQBJS-UHFFFAOYSA-N 0.000 description 1
- UCRCZYGBYIYSDA-UHFFFAOYSA-N n-benzyl-3-[4-[3-(benzylamino)propyl]phenyl]propan-1-amine Chemical compound C=1C=C(CCCNCC=2C=CC=CC=2)C=CC=1CCCNCC1=CC=CC=C1 UCRCZYGBYIYSDA-UHFFFAOYSA-N 0.000 description 1
- AZCVBVRUYHKWHU-UHFFFAOYSA-N penicillin X Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=C(O)C=C1 AZCVBVRUYHKWHU-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N xylylenediamine group Chemical group C=1(C(=CC=CC1)CN)CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 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)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE549328A true BE549328A (enExample) |
Family
ID=175598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE549328D BE549328A (enExample) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE549328A (enExample) |
-
0
- BE BE549328D patent/BE549328A/fr unknown
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