NO134437B - - Google Patents
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- Publication number
- NO134437B NO134437B NO498370A NO498370A NO134437B NO 134437 B NO134437 B NO 134437B NO 498370 A NO498370 A NO 498370A NO 498370 A NO498370 A NO 498370A NO 134437 B NO134437 B NO 134437B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- mcg
- staph
- solution
- ether
- Prior art date
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- 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 66
- 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 66
- 238000000034 method Methods 0.000 claims description 33
- -1 alkylsulfonyl radicals Chemical class 0.000 claims description 30
- 229930182555 Penicillin Natural products 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000002960 penicillins Chemical class 0.000 claims description 13
- 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 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000000855 fermentation Methods 0.000 claims description 4
- 230000004151 fermentation Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 241000191967 Staphylococcus aureus Species 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 199
- 239000000243 solution Substances 0.000 description 135
- 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 104
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 89
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 82
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 68
- 239000008346 aqueous phase Substances 0.000 description 62
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 55
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 54
- 159000000000 sodium salts Chemical class 0.000 description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 49
- 229940056360 penicillin g Drugs 0.000 description 49
- 235000019371 penicillin G benzathine Nutrition 0.000 description 46
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 44
- 235000017557 sodium bicarbonate Nutrition 0.000 description 44
- 238000007792 addition Methods 0.000 description 42
- 239000002253 acid Substances 0.000 description 40
- 239000007787 solid Substances 0.000 description 35
- 239000000203 mixture Substances 0.000 description 31
- 239000007864 aqueous solution Substances 0.000 description 27
- 238000010438 heat treatment Methods 0.000 description 23
- 230000007935 neutral effect Effects 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 229940049954 penicillin Drugs 0.000 description 16
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000010779 crude oil Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 238000004737 colorimetric analysis Methods 0.000 description 9
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- 239000012259 ether extract Substances 0.000 description 8
- 239000012258 stirred mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 4
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 4
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 description 3
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 3
- 229930195708 Penicillin V Natural products 0.000 description 3
- 108010087702 Penicillinase Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229940056367 penicillin v Drugs 0.000 description 3
- 229950009506 penicillinase 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
- 239000011591 potassium Substances 0.000 description 3
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 239000004552 water soluble powder Substances 0.000 description 3
- UOZBNMMELVBICG-UHFFFAOYSA-N 2,2,2-triphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)Cl)C1=CC=CC=C1 UOZBNMMELVBICG-UHFFFAOYSA-N 0.000 description 2
- WUVVBAGGJHUHCN-UHFFFAOYSA-N 2,2-diphenyl-2-propan-2-yloxyacetyl chloride Chemical compound C(C)(C)OC(C(=O)Cl)(C1=CC=CC=C1)C1=CC=CC=C1 WUVVBAGGJHUHCN-UHFFFAOYSA-N 0.000 description 2
- QFGJEMLJOJHIHH-UHFFFAOYSA-N 2-ethoxy-2,2-diphenylacetyl chloride Chemical compound C(C)OC(C(=O)Cl)(C1=CC=CC=C1)C1=CC=CC=C1 QFGJEMLJOJHIHH-UHFFFAOYSA-N 0.000 description 2
- WWIJGHHDQFJHQW-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=CC=C1 WWIJGHHDQFJHQW-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CRZOVMCPXBUWHS-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(=O)Cl)(OC)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(C(=O)Cl)(OC)C1=CC=CC=C1 CRZOVMCPXBUWHS-UHFFFAOYSA-N 0.000 description 2
- NUMSZXAKJYNZFR-UHFFFAOYSA-N CCSC(C(Cl)=O)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CCSC(C(Cl)=O)(C1=CC=CC=C1)C1=CC=CC=C1 NUMSZXAKJYNZFR-UHFFFAOYSA-N 0.000 description 2
- LXZKBEMDKCBDCO-UHFFFAOYSA-N COC1=CC=C(C=C1)C1(C(Cl)=O)C2=CC=CC=C2C2=C1C=CC=C2 Chemical compound COC1=CC=C(C=C1)C1(C(Cl)=O)C2=CC=CC=C2C2=C1C=CC=C2 LXZKBEMDKCBDCO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HXEPBVAIJSTAED-UHFFFAOYSA-N O=C(C(C1=CC=CC=C1)(C1=CC=CC=C1)SCC1=CC=CC=C1)Cl Chemical compound O=C(C(C1=CC=CC=C1)(C1=CC=CC=C1)SCC1=CC=CC=C1)Cl HXEPBVAIJSTAED-UHFFFAOYSA-N 0.000 description 2
- ORWFBNANOAZJJN-UHFFFAOYSA-N S1C(=CC=C1)C(C(=O)Cl)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound S1C(=CC=C1)C(C(=O)Cl)(C1=CC=CC=C1)C1=CC=CC=C1 ORWFBNANOAZJJN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 150000003939 benzylamines Chemical class 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000003946 cyclohexylamines Chemical class 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- XUZOAPJJYBDXIC-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonyl chloride Chemical compound C=1C=CC=CC=1C1(C(=O)Cl)CCCCC1 XUZOAPJJYBDXIC-UHFFFAOYSA-N 0.000 description 1
- NOYKUYNVZHTPCI-UHFFFAOYSA-N 1-phenylcyclopentane-1-carbonyl chloride Chemical compound C=1C=CC=CC=1C1(C(=O)Cl)CCCC1 NOYKUYNVZHTPCI-UHFFFAOYSA-N 0.000 description 1
- BDUZRQVRGUYXTQ-UHFFFAOYSA-N 2,2,2-tris(4-methoxyphenyl)acetic acid Chemical compound C1=CC(OC)=CC=C1C(C(O)=O)(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BDUZRQVRGUYXTQ-UHFFFAOYSA-N 0.000 description 1
- SRWRRMSFRFGNDQ-UHFFFAOYSA-N 2,2,2-tris(4-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(C=C1)C(C(=O)Cl)(C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC SRWRRMSFRFGNDQ-UHFFFAOYSA-N 0.000 description 1
- RKPSPRBQDXXYPM-UHFFFAOYSA-N 2,2-dibutylhexanoyl chloride Chemical compound CCCCC(CCCC)(CCCC)C(Cl)=O RKPSPRBQDXXYPM-UHFFFAOYSA-N 0.000 description 1
- MUXPPYATEKVUBJ-UHFFFAOYSA-N 2,2-diethylbutanoyl chloride Chemical compound CCC(CC)(CC)C(Cl)=O MUXPPYATEKVUBJ-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- ABUGEGRXTCTHSP-UHFFFAOYSA-N 2,2-diphenyl-2-propan-2-yloxyacetic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(OC(C)C)C1=CC=CC=C1 ABUGEGRXTCTHSP-UHFFFAOYSA-N 0.000 description 1
- DCKKPZRBDLWROD-UHFFFAOYSA-N 2,2-diphenyl-2-propan-2-ylsulfanylacetyl chloride Chemical compound C(C)(C)SC(C(=O)Cl)(C1=CC=CC=C1)C1=CC=CC=C1 DCKKPZRBDLWROD-UHFFFAOYSA-N 0.000 description 1
- NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 1
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 1
- YUFRSRYLPNQZRU-UHFFFAOYSA-N 2,2-dipropylpentanoyl chloride Chemical compound C(CC)C(C(=O)Cl)(CCC)CCC YUFRSRYLPNQZRU-UHFFFAOYSA-N 0.000 description 1
- LUTZMJZHVATZQM-UHFFFAOYSA-N 2-bromo-2-ethylbutanoyl bromide Chemical compound CCC(Br)(CC)C(Br)=O LUTZMJZHVATZQM-UHFFFAOYSA-N 0.000 description 1
- WCUMEPYJVQJQCR-UHFFFAOYSA-N 2-chloro-2-cyclohexyl-2-phenylacetyl chloride Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)Cl)C1CCCCC1 WCUMEPYJVQJQCR-UHFFFAOYSA-N 0.000 description 1
- SEUTWLXKEMEBTR-UHFFFAOYSA-N 2-ethoxy-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(OCC)C1=CC=CC=C1 SEUTWLXKEMEBTR-UHFFFAOYSA-N 0.000 description 1
- NGHYFCDORXGZOD-UHFFFAOYSA-N 2-ethylsulfanyl-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(SCC)C1=CC=CC=C1 NGHYFCDORXGZOD-UHFFFAOYSA-N 0.000 description 1
- YNDNIPMGZASSRG-UHFFFAOYSA-N 2-methoxy-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(OC)C1=CC=CC=C1 YNDNIPMGZASSRG-UHFFFAOYSA-N 0.000 description 1
- ROCLESYSBRXBIV-UHFFFAOYSA-N 9-(4-methoxyphenyl)fluorene-9-carboxylic acid Chemical compound COC1=CC=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C(=O)O ROCLESYSBRXBIV-UHFFFAOYSA-N 0.000 description 1
- SLDSXXJFNOYUOU-UHFFFAOYSA-N 9-methoxyfluorene-9-carboxylic acid Chemical compound C1=CC=C2C(OC)(C(O)=O)C3=CC=CC=C3C2=C1 SLDSXXJFNOYUOU-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- AWSPEMPXVRDTGI-UHFFFAOYSA-N CC1=CC=C(C2=CC=CC=C12)C(C(=O)Cl)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CC1=CC=C(C2=CC=CC=C12)C(C(=O)Cl)(C1=CC=CC=C1)C1=CC=CC=C1 AWSPEMPXVRDTGI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000228150 Penicillium chrysogenum Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- YSMHTFWPDRJCMN-UHFFFAOYSA-N butan-2-yl carbonochloridate Chemical compound CCC(C)OC(Cl)=O YSMHTFWPDRJCMN-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO498370A NO134437C (enrdf_load_html_response) | 1965-03-18 | 1970-12-30 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44075265A | 1965-03-18 | 1965-03-18 | |
| GB1185565A GB1102762A (en) | 1965-03-19 | 1965-03-19 | Phthalane, isochromane and isochromene derivatives |
| NO162148A NO123675B (enrdf_load_html_response) | 1965-03-18 | 1966-03-17 | |
| US75950368A | 1968-09-12 | 1968-09-12 | |
| NO498370A NO134437C (enrdf_load_html_response) | 1965-03-18 | 1970-12-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134437B true NO134437B (enrdf_load_html_response) | 1976-06-28 |
| NO134437C NO134437C (enrdf_load_html_response) | 1976-10-06 |
Family
ID=27516086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO498370A NO134437C (enrdf_load_html_response) | 1965-03-18 | 1970-12-30 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO134437C (enrdf_load_html_response) |
-
1970
- 1970-12-30 NO NO498370A patent/NO134437C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO134437C (enrdf_load_html_response) | 1976-10-06 |
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