CH505853A - Verfahren zur Herstellung von Penicillinen - Google Patents

Verfahren zur Herstellung von Penicillinen

Info

Publication number: CH505853A
Authority: CH; Switzerland
Prior art keywords: phenyl; mol; substd; acid; yield
Prior art date: 1966-11-05

Application number

CH1548867A

Other languages

German (de)

English (en)

Inventor

David Hardy Kenneth

Charles Nayler John Herbert

Raymond Stove Edward

Original Assignee

Beecham Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-11-05

Filing date

1967-11-06

Publication date

1971-04-15

1967-11-06 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1971-04-15 Publication of CH505853A publication Critical patent/CH505853A/de

Links

229930182555 Penicillin Natural products 0.000 title claims abstract description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 20
125000001624 naphthyl group Chemical group 0.000 title claims abstract description 8
125000000217 alkyl group Chemical group 0.000 title claims abstract description 4
125000001544 thienyl group Chemical group 0.000 title claims abstract description 4
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 title abstract description 55
229940049954 penicillin Drugs 0.000 title abstract description 21
125000002541 furyl group Chemical group 0.000 title abstract 2
-1 nitro- Chemical group 0.000 claims abstract description 38
150000003839 salts Chemical class 0.000 claims abstract description 9
231100000252 nontoxic Toxicity 0.000 claims abstract description 7
230000003000 nontoxic effect Effects 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical group 0.000 claims abstract description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
125000004970 halomethyl group Chemical group 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
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 26
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 26
238000000034 method Methods 0.000 claims description 14
150000002960 penicillins Chemical class 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000003141 primary amines Chemical class 0.000 claims description 2
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
229940056360 penicillin g Drugs 0.000 abstract description 23
235000019371 penicillin G benzathine Nutrition 0.000 abstract description 18
239000000203 mixture Substances 0.000 abstract description 10
150000001875 compounds Chemical class 0.000 abstract description 5
241000894006 Bacteria Species 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
229910052751 metal Inorganic materials 0.000 abstract description 2
239000002184 metal Substances 0.000 abstract description 2
244000144977 poultry Species 0.000 abstract description 2
230000000069 prophylactic effect Effects 0.000 abstract description 2
241001465754 Metazoa Species 0.000 abstract 1
150000003863 ammonium salts Chemical class 0.000 abstract 1
208000015181 infectious disease Diseases 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 114
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
239000000126 substance Substances 0.000 description 39
159000000000 sodium salts Chemical class 0.000 description 34
239000007787 solid Substances 0.000 description 29
WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 23
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 description 21
239000000243 solution Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 19
239000013078 crystal Substances 0.000 description 18
239000003208 petroleum Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
239000000284 extract Substances 0.000 description 11
239000007795 chemical reaction product Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
238000005303 weighing Methods 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000006286 aqueous extract Substances 0.000 description 4
RJMBEVGAJVTPDY-UHFFFAOYSA-N 3-oxo-3-phenoxy-2-thiophen-2-ylpropanoic acid Chemical compound C=1C=CSC=1C(C(=O)O)C(=O)OC1=CC=CC=C1 RJMBEVGAJVTPDY-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
GCOOGCQWQFRJEK-UHFFFAOYSA-N 2-thiophen-3-ylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)C=1C=CSC=1 GCOOGCQWQFRJEK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
NIBKDWIGIKUFKL-UHFFFAOYSA-N 1,2,2-trichloroethanol Chemical compound OC(Cl)C(Cl)Cl NIBKDWIGIKUFKL-UHFFFAOYSA-N 0.000 description 1
KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
QJFIXBNLKARINT-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonylethanol Chemical compound CC1=CC=C(S(=O)(=O)CCO)C=C1 QJFIXBNLKARINT-UHFFFAOYSA-N 0.000 description 1
KMNMQDSIICMJOJ-UHFFFAOYSA-N 2-[4-(2-methylphenyl)phenyl]propanedioic acid Chemical compound C1(=C(C=CC=C1)C1=CC=C(C=C1)C(C(=O)O)C(=O)O)C KMNMQDSIICMJOJ-UHFFFAOYSA-N 0.000 description 1
GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 description 1
LJNDRJPZYNGSKZ-UHFFFAOYSA-N 2-ethylsulfonylethanol Chemical compound CCS(=O)(=O)CCO LJNDRJPZYNGSKZ-UHFFFAOYSA-N 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
OIJPSMYQMUNKSB-UHFFFAOYSA-N 2-thiophen-2-ylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)C1=CC=CS1 OIJPSMYQMUNKSB-UHFFFAOYSA-N 0.000 description 1
ILCZVFZOSDGLMA-UHFFFAOYSA-N 3-O-(4-methoxyphenyl) 1-O-phenyl propanedioate Chemical compound COC1=CC=C(OC(=O)CC(=O)OC2=CC=CC=C2)C=C1 ILCZVFZOSDGLMA-UHFFFAOYSA-N 0.000 description 1
QPVAVQYXWABJQO-UHFFFAOYSA-N 3-naphthalen-2-yloxy-3-oxo-2-phenylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=O)C(C(=O)O)C1=CC=CC=C1 QPVAVQYXWABJQO-UHFFFAOYSA-N 0.000 description 1
IDJNJFYWPMDFNB-UHFFFAOYSA-N 3-oxo-3-phenoxy-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C(=O)OC1=CC=CC=C1 IDJNJFYWPMDFNB-UHFFFAOYSA-N 0.000 description 1
HNDJSZKHMKQXTR-UHFFFAOYSA-N 3-oxo-3-phenoxy-2-thiophen-3-ylpropanoic acid Chemical compound C1=CSC=C1C(C(=O)O)C(=O)OC1=CC=CC=C1 HNDJSZKHMKQXTR-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
YBEBCWKYTDYYOE-UHFFFAOYSA-N C(CC(=O)OC1=CC=CC=C1)(=O)OCC(CC)[N+](=O)[O-] Chemical compound C(CC(=O)OC1=CC=CC=C1)(=O)OCC(CC)[N+](=O)[O-] YBEBCWKYTDYYOE-UHFFFAOYSA-N 0.000 description 1
KYZXYBAQZYKRJR-UHFFFAOYSA-N CCC(CC(C(O)=O)(C(O)=O)C1=CC=CC=C1)[N+]([O-])=O Chemical compound CCC(CC(C(O)=O)(C(O)=O)C1=CC=CC=C1)[N+]([O-])=O KYZXYBAQZYKRJR-UHFFFAOYSA-N 0.000 description 1
LESDXRPGDLYRFK-UHFFFAOYSA-N CCOC(C(C=CC=C1)=C1OC(C(C(O)=O)C1=CC=CC=C1)=O)=O Chemical compound CCOC(C(C=CC=C1)=C1OC(C(C(O)=O)C1=CC=CC=C1)=O)=O LESDXRPGDLYRFK-UHFFFAOYSA-N 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
QKYLDFPYTFNYSI-UHFFFAOYSA-N ClC1=CC=C(C=C1)C(C(=O)O)(C(=O)O)C1=CC=CC=C1 Chemical compound ClC1=CC=C(C=C1)C(C(=O)O)(C(=O)O)C1=CC=CC=C1 QKYLDFPYTFNYSI-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-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
125000004423 acyloxy group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
OJYGBLRPYBAHRT-UHFFFAOYSA-N alphachloralose Chemical compound O1C(C(Cl)(Cl)Cl)OC2C(O)C(C(O)CO)OC21 OJYGBLRPYBAHRT-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
208000022362 bacterial infectious disease Diseases 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229950011260 betanaphthol Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
ASAWUXMEXFAFMU-DBDULZNHSA-N crotepoxide Chemical compound C([C@@]12O[C@@H]1[C@@H]1O[C@@H]1[C@H]([C@@H]2OC(C)=O)OC(=O)C)OC(=O)C1=CC=CC=C1 ASAWUXMEXFAFMU-DBDULZNHSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 1
SAXHIDRUJXPDOD-UHFFFAOYSA-N ethyl hydroxy(phenyl)acetate Chemical compound CCOC(=O)C(O)C1=CC=CC=C1 SAXHIDRUJXPDOD-UHFFFAOYSA-N 0.000 description 1
229940005667 ethyl salicylate Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229960005323 phenoxyethanol Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 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
239000000047 product Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—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

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1548867A 1966-11-05 1967-11-06 Verfahren zur Herstellung von Penicillinen CH505853A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB4969766A GB1133886A (en)	1966-11-05	1966-11-05	Penicillins
GB407967		1967-01-27

Publications (1)

Publication Number	Publication Date
CH505853A true CH505853A (de)	1971-04-15

Family

ID=26238849

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1548867A CH505853A (de)	1966-11-05	1967-11-06	Verfahren zur Herstellung von Penicillinen

Country Status (10)

Country	Link
AT (1)	AT281284B (fr)
BE (1)	BE706051A (fr)
CH (1)	CH505853A (fr)
DK (1)	DK132085C (fr)
ES (1)	ES346793A1 (fr)
FI (1)	FI50426C (fr)
FR (1)	FR6819M (fr)
GB (1)	GB1133886A (fr)
NL (1)	NL153203B (fr)
NO (1)	NO131135C (fr)

1966
- 1966-11-05 GB GB4969766A patent/GB1133886A/en not_active Expired
1967
- 1967-10-27 FI FI289867A patent/FI50426C/fi active
- 1967-10-30 NL NL676714747A patent/NL153203B/xx not_active IP Right Cessation
- 1967-10-30 NO NO17032267A patent/NO131135C/no unknown
- 1967-10-31 AT AT983067A patent/AT281284B/de not_active IP Right Cessation
- 1967-11-03 FR FR126847A patent/FR6819M/fr not_active Expired
- 1967-11-03 DK DK548267A patent/DK132085C/da active
- 1967-11-03 BE BE706051D patent/BE706051A/xx not_active IP Right Cessation
- 1967-11-04 ES ES346793A patent/ES346793A1/es not_active Expired
- 1967-11-06 CH CH1548867A patent/CH505853A/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE706051A (fr)	1968-05-03
FI50426C (fi)	1976-03-10
DK132085B (da)	1975-10-20
GB1133886A (en)	1968-11-20
FR6819M (fr)	1969-03-24
NL6714747A (fr)	1968-05-06
DE1670284B2 (de)	1976-02-26
DE1670284A1 (de)	1971-01-28
NL153203B (nl)	1977-05-16
FI50426B (fr)	1975-12-01
ES346793A1 (es)	1969-02-16
NO131135C (fr)	1975-04-09
NO131135B (fr)	1974-12-30
DK132085C (da)	1976-03-15
AT281284B (de)	1970-05-11

Legal Events

Date	Code	Title	Description
1986-07-31	PL	Patent ceased

Publication	Publication Date	Title
DE2629752A1 (de)	1978-01-05	Neue carbonsaeurederivate und verfahren zu ihrer herstellung
DE2241012A1 (de)	1973-03-15	Neue 3,1-benzoxazin-4-on-derivate und verfahren zur herstellung derselben
DE1670222C3 (de)	1979-04-05	a-(Benzyloxycarbonyl)-thienyunethylpenicilline und deren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende antibakterielle Mittel
CH505853A (de)	1971-04-15	Verfahren zur Herstellung von Penicillinen
DE1670163C3 (de)	1973-11-29	Cephaloglycindenvat und Verfahren zu seiner Herstellung
DE946804C (de)	1956-08-09	Verfahren zur Herstellung von schwefelhaltigen Abkoemmlingen der Barbitursaeure
DE2033090C3 (de)	1981-01-29	deren Herstellung
CH394206A (de)	1965-06-30	Verfahren zur Herstellung von Abkömmlingen der 6-Amino-penicillansäure
AT207373B (de)	1960-01-25	Verfahren zur Herstellung von Äthyleniminderivaten
AT323161B (de)	1975-06-25	Verfahren zur herstellung neuer 2-carboxy-4-oxo-4h, 10h(2)-benzopyrano-(4,3-g)-(1)-benzopyrane und ihrer salze
AT267493B (de)	1968-12-27	Verfahren zur Herstellung der d,1-trans-Chrysanthemumsäure und ihrer funktionellen Derivate
DE2251290C3 (de)	1981-09-03	α-Sulfo-p-aminobenzylpenicillin
AT371457B (de)	1983-06-27	Verfahren zur herstellung von neuen 6-substituierten pyranon-verbindungen
AT332881B (de)	1976-10-25	Verfahren zur herstellung des neuen n-(4-(beta- (2-methoxy-5-chlor-benzamido) -athyl)-benzolsulfonyl) -n'-cyclopentylharnstoffs und seiner salze
AT259132B (de)	1967-12-27	Verfahren zur Herstellung von neuen Penicillinderivaten
DE1900948C (de)	1971-09-23	Cis- und trans-2-Methyl-5-(3, 4, S-trimethoxybenzamidoJ-decahydroisochinolin
AT296316B (de)	1972-02-10	Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten und deren N-4-Oxyden
AT214454B (de)	1961-04-10	Verfahren zur Herstellung neuer Phosphinsäurederivate
DE1954839A1 (de)	1970-05-06	Tetrazolderivate
DE2337446A1 (de)	1975-02-13	Hydroxythia-azabicyclo-octanone und verfahren zu ihrer herstellung
DE2058012A1 (de)	1971-06-03	alpha-Imidoacrylsaeureester,Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide oder in Insektiziden
DE1545807A1 (de)	1969-11-27	Verfahren zur Herstellung von 2-Halogen-1,3-benzothiazinonen-4-
DE1010531B (de)	1957-06-19	Verfahren zur Herstellung von Dioxanverbindungen
CH529087A (de)	1972-10-15	Verfahren zur Herstellung neuer a-Phenylcarbonsäuren und ihre Ester
DE2304536A1 (de)	1974-08-01	2-hydroxy-3-cyano-chinoxalin-di-noxide