DD143259A5 - Verfahren zur herstellung von penicillansaeurederivaten - Google Patents

Verfahren zur herstellung von penicillansaeurederivaten Download PDF

Info

Publication number: DD143259A5
Authority: DD; German Democratic Republic
Prior art keywords: group; item; formula; hydrogen atom; acid
Prior art date: 1978-05-26

Application number

DD79210631A

Other languages

German (de)

English (en)

Inventor

Nobuhiro Oi

Bunya Aoki

Teizo Shinozaki

Kanji Moro

Isao Matsunaga

Takao Noto

Toshiyuki Nebashi

Yusuke Harada

Hisao Endo

Takao Kimura

Hiroshi Okazaki

Haruki Ogawa

Minoru Shindo

Original Assignee

Chugai Pharmaceutical Co 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.)

1978-05-26

Filing date

1979-01-25

Publication date

1980-08-13

1978-05-26 Priority claimed from JP6216478A external-priority patent/JPS54154782A/ja

1978-06-13 Priority claimed from JP7036578A external-priority patent/JPS54163590A/ja

1978-08-11 Priority claimed from JP9730978A external-priority patent/JPS5524135A/ja

1978-08-29 Priority claimed from JP10436278A external-priority patent/JPS5531044A/ja

1978-09-07 Priority claimed from JP10915778A external-priority patent/JPS5536411A/ja

1979-01-25 Application filed by Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd

1980-08-13 Publication of DD143259A5 publication Critical patent/DD143259A5/de

Links

238000000034 method Methods 0.000 title claims description 67
238000002360 preparation method Methods 0.000 title claims description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 159
-1 benzoyl halide Chemical class 0.000 claims description 113
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 108
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 71
238000006243 chemical reaction Methods 0.000 claims description 62
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 60
150000001875 compounds Chemical class 0.000 claims description 58
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
239000002904 solvent Substances 0.000 claims description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 32
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
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125000004423 acyloxy group Chemical group 0.000 claims description 18
125000006239 protecting group Chemical group 0.000 claims description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
GIOUOHDKHHZWIQ-UHFFFAOYSA-N 2-(carbamoylamino)-2-phenylacetic acid Chemical class NC(=O)NC(C(O)=O)C1=CC=CC=C1 GIOUOHDKHHZWIQ-UHFFFAOYSA-N 0.000 claims description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
150000002148 esters Chemical group 0.000 claims description 13
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 12
125000001424 substituent group Chemical group 0.000 claims description 12
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 11
239000003960 organic solvent Substances 0.000 claims description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 claims description 4
230000035484 reaction time Effects 0.000 claims description 4
150000001408 amides Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
125000004018 acid anhydride group Chemical group 0.000 claims 1
235000019371 penicillin G benzathine Nutrition 0.000 claims 1
239000000243 solution Substances 0.000 description 70
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
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238000004809 thin layer chromatography Methods 0.000 description 37
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 35
239000000047 product Substances 0.000 description 35
238000002329 infrared spectrum Methods 0.000 description 31
238000003756 stirring Methods 0.000 description 31
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
239000012044 organic layer Substances 0.000 description 26
229920006395 saturated elastomer Polymers 0.000 description 26
239000007787 solid Substances 0.000 description 25
239000010410 layer Substances 0.000 description 24
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
229960003424 phenylacetic acid Drugs 0.000 description 20
239000003279 phenylacetic acid Substances 0.000 description 20
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 19
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 18
239000000843 powder Substances 0.000 description 17
239000011780 sodium chloride Substances 0.000 description 17
239000000126 substance Substances 0.000 description 17
238000002211 ultraviolet spectrum Methods 0.000 description 16
239000002585 base Substances 0.000 description 15
238000001816 cooling Methods 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
229910021578 Iron(III) chloride Inorganic materials 0.000 description 13
XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 11
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 10
238000001914 filtration Methods 0.000 description 10
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000005457 ice water Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
150000008065 acid anhydrides Chemical class 0.000 description 7
230000001476 alcoholic effect Effects 0.000 description 7
UNCACEGCFURZQB-UHFFFAOYSA-N (2-acetyloxy-4-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(Cl)=O)C=C1OC(C)=O UNCACEGCFURZQB-UHFFFAOYSA-N 0.000 description 6
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 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
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AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000003456 ion exchange resin Substances 0.000 description 6
229920003303 ion-exchange polymer Polymers 0.000 description 6
ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
229930182555 Penicillin Natural products 0.000 description 5
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 5
OKMHHBICYZAXBE-UHFFFAOYSA-N acetic acid;ethanol;ethyl acetate Chemical compound CCO.CC(O)=O.CCOC(C)=O OKMHHBICYZAXBE-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
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239000007864 aqueous solution Substances 0.000 description 5
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
238000002955 isolation Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
KCDXWFVBWDBQIE-UHFFFAOYSA-N (2-acetyloxy-4-carbamoylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(N)=O)C=C1OC(C)=O KCDXWFVBWDBQIE-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229910052742 iron Inorganic materials 0.000 description 4
229940049954 penicillin Drugs 0.000 description 4
150000002960 penicillins Chemical class 0.000 description 4
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
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SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 4
NVOKNDLZPHTWQO-UHFFFAOYSA-N (2,3-diacetyloxy-5-carbonisocyanatidoylphenyl) acetate Chemical compound CC(=O)OC1=CC(C(=O)N=C=O)=CC(OC(C)=O)=C1OC(C)=O NVOKNDLZPHTWQO-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
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241000894006 Bacteria Species 0.000 description 3
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238000005481 NMR spectroscopy Methods 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
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150000001340 alkali metals Chemical class 0.000 description 3
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LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 3
229960004920 amoxicillin trihydrate Drugs 0.000 description 3
229960003311 ampicillin trihydrate Drugs 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
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150000007529 inorganic bases Chemical class 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
238000010992 reflux Methods 0.000 description 3
SBGXXBVOLADOOR-UHFFFAOYSA-N (2-acetyloxy-3-carbonisocyanatidoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(=O)N=C=O)=C1OC(C)=O SBGXXBVOLADOOR-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
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LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000589516 Pseudomonas Species 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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229960000723 ampicillin Drugs 0.000 description 2
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230000000844 anti-bacterial effect Effects 0.000 description 2
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FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 2
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150000001718 carbodiimides Chemical class 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
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230000008018 melting Effects 0.000 description 2
VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
AHBNUYOASRDREM-UHFFFAOYSA-N (2,3-diacetyloxy-5-carbamoylphenyl) acetate Chemical compound CC(=O)OC1=CC(C(N)=O)=CC(OC(C)=O)=C1OC(C)=O AHBNUYOASRDREM-UHFFFAOYSA-N 0.000 description 1
RVJVBYRLRQOHCL-UHFFFAOYSA-N (2,3-diacetyloxy-5-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC(C(Cl)=O)=CC(OC(C)=O)=C1OC(C)=O RVJVBYRLRQOHCL-UHFFFAOYSA-N 0.000 description 1
LLGJUWCBCMAZRK-UHFFFAOYSA-N (2-acetyloxy-3-carbamoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(N)=O)=C1OC(C)=O LLGJUWCBCMAZRK-UHFFFAOYSA-N 0.000 description 1
JWIRVWSAMLMXIV-UHFFFAOYSA-N (2-acetyloxy-3-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(Cl)=O)=C1OC(C)=O JWIRVWSAMLMXIV-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-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
RMIJYCIGXVCHAF-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;n,n-diethylethanamine;n,n-dimethylformamide Chemical compound CN(C)C=O.CCN(CC)CC.OCCN(CCO)CCO RMIJYCIGXVCHAF-UHFFFAOYSA-N 0.000 description 1
YSMYHWBQQONPRD-UHFFFAOYSA-N 2-chlorofuran Chemical compound ClC1=CC=CO1 YSMYHWBQQONPRD-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 1
WNPVZANXRCPJPW-UHFFFAOYSA-N 5-[isocyano-(4-methylphenyl)sulfonylmethyl]-1,2,3-trimethoxybenzene Chemical compound COC1=C(OC)C(OC)=CC(C([N+]#[C-])S(=O)(=O)C=2C=CC(C)=CC=2)=C1 WNPVZANXRCPJPW-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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 1
150000007945 N-acyl ureas Chemical class 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
BFJSMSPRRMOLIE-UHFFFAOYSA-N [2,3-diacetyloxy-5-(methylcarbamoyl)phenyl] acetate Chemical compound CNC(=O)C1=CC(OC(C)=O)=C(OC(C)=O)C(OC(C)=O)=C1 BFJSMSPRRMOLIE-UHFFFAOYSA-N 0.000 description 1
CLXGFJDXCVPBHR-UHFFFAOYSA-N [2-acetyloxy-4-(ethylcarbamoyl)phenyl] acetate Chemical compound CCNC(=O)C1=CC=C(OC(C)=O)C(OC(C)=O)=C1 CLXGFJDXCVPBHR-UHFFFAOYSA-N 0.000 description 1
MHDYEKBSPRGXKV-UHFFFAOYSA-N [2-acetyloxy-4-(methylcarbamoyl)phenyl] acetate Chemical compound CNC(=O)C1=CC=C(OC(C)=O)C(OC(C)=O)=C1 MHDYEKBSPRGXKV-UHFFFAOYSA-N 0.000 description 1
NNFFSHMEYWJGHP-UHFFFAOYSA-N [2-acetyloxy-4-[carbonochloridoyl(methyl)carbamoyl]phenyl] acetate Chemical compound ClC(=O)N(C)C(=O)C1=CC=C(OC(C)=O)C(OC(C)=O)=C1 NNFFSHMEYWJGHP-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
235000012538 ammonium bicarbonate Nutrition 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
239000012847 fine chemical Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
YCOFRPYSZKIPBQ-UHFFFAOYSA-N penicillic acid Natural products COC1=CC(=O)OC1(O)C(C)=C YCOFRPYSZKIPBQ-UHFFFAOYSA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 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
238000000746 purification Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing 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)

DD79210631A 1978-05-26 1979-01-25 Verfahren zur herstellung von penicillansaeurederivaten DD143259A5 (de)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
JP6216478A JPS54154782A (en)	1978-05-26	1978-05-26	Penicillin derivative and its salt
JP7036578A JPS54163590A (en)	1978-06-13	1978-06-13	Penicilunic acid derivative and salt thereof
JP9730978A JPS5524135A (en)	1978-08-11	1978-08-11	Penicillin derivative and its preparation
JP10436278A JPS5531044A (en)	1978-08-29	1978-08-29	Penicillanic acid derivative and its preparation
JP10915778A JPS5536411A (en)	1978-09-07	1978-09-07	Benzylpenicillin derivative and their preparation

Publications (1)

Publication Number	Publication Date
DD143259A5 true DD143259A5 (de)	1980-08-13

Family

ID=27523696

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79210631A DD143259A5 (de)	1978-05-26	1979-01-25	Verfahren zur herstellung von penicillansaeurederivaten

Country Status (15)

Country	Link
US (1)	US4229348A (fr)
AU (1)	AU4689879A (fr)
CA (1)	CA1133896A (fr)
DD (1)	DD143259A5 (fr)
DE (1)	DE2921324C2 (fr)
DK (1)	DK179579A (fr)
FI (1)	FI791680A7 (fr)
FR (1)	FR2426691A1 (fr)
GB (1)	GB2021576B (fr)
HU (1)	HU176076B (fr)
IL (1)	IL57264A0 (fr)
IT (1)	IT1120970B (fr)
NL (1)	NL7904112A (fr)
NO (1)	NO791687L (fr)
PT (1)	PT69665A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5732289A (en) *	1980-08-05	1982-02-20	Chugai Pharmaceut Co Ltd	Alpha-substituted ureidobenzylpenicillin
DE3372208D1 (en) *	1982-04-29	1987-07-30	Beecham Group Plc	Beta-lactam antibiotics
CN1764374B (zh) *	2003-03-26	2010-09-22	拜尔作物科学股份公司	芳族羟基化合物用作安全剂的用途
EP4141110A4 (fr)	2020-04-24	2025-04-09	Sf Biotech Laboratuvar Danismanlik Anonim Sirketi	Procédé de production de particules de bactériophages de la famille levivirus

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE32700B1 (en) *	1968-02-03	1973-10-31	Beecham Group Ltd	Penicillins
GB1250611A (fr) *	1968-02-03	1971-10-20
DE1770620A1 (de) *	1968-06-12	1971-11-11	Bayer Ag	Neue Penicilline
US3479339A (en) *	1968-06-13	1969-11-18	Bristol Myers Co	6-(alpha-3 - acylureidophenylacetamido)- and 6-(alpha - 3 - acylureidothienylacetamido)-penicillanic acids
US3933795A (en) *	1970-05-25	1976-01-20	Hans-Bodo Konig	Ureidoacetamido-penicillins
US3978223A (en) *	1970-05-25	1976-08-31	Bayer Aktiengesellschaft	Ureidoacetamido-penicillins for treating bacterial infections
US3974140A (en) *	1970-05-25	1976-08-10	Bayer Aktiengesellschaft	Ureidoacetamido-penicillins
US4016282A (en) *	1970-05-25	1977-04-05	Bayer Aktiengesellschaft	Ureidoacetamido-penicillins
US3980792A (en) *	1970-05-25	1976-09-14	Bayer Aktiengesellschaft	Ureidoacetamido-penicillins
US3936442A (en) *	1970-05-25	1976-02-03	Bayer Aktiengesellschaft	Unreidoacetamido-penicilins
US3939149A (en) *	1970-05-25	1976-02-17	Bayer Aktiengesellschaft	Ureidoacetamido-penicillins
US3959258A (en) *	1970-05-25	1976-05-25	Bayer Aktiengesellschaft	Ureidoacetamido-penicillins
CH562249A5 (fr) *	1970-05-25	1975-05-30	Bayer Ag
GB1433131A (en) *	1972-03-13	1976-04-22	Astra Laekemedel Ab	Penicillins
DE2258973A1 (de) *	1972-12-01	1974-06-06	Bayer Ag	Penicilline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

1979
- 1979-01-23 US US06/005,832 patent/US4229348A/en not_active Expired - Lifetime
- 1979-01-23 CA CA320,106A patent/CA1133896A/fr not_active Expired
- 1979-01-25 DD DD79210631A patent/DD143259A5/de unknown
- 1979-01-26 HU HU79CU160A patent/HU176076B/hu unknown
- 1979-05-01 DK DK179579A patent/DK179579A/da unknown
- 1979-05-09 AU AU46898/79A patent/AU4689879A/en not_active Abandoned
- 1979-05-09 GB GB7916058A patent/GB2021576B/en not_active Expired
- 1979-05-14 IL IL57264A patent/IL57264A0/xx unknown
- 1979-05-22 NO NO791687A patent/NO791687L/no unknown
- 1979-05-24 PT PT69665A patent/PT69665A/pt unknown
- 1979-05-24 IT IT68103/79A patent/IT1120970B/it active
- 1979-05-25 FR FR7913332A patent/FR2426691A1/fr active Granted
- 1979-05-25 FI FI791680A patent/FI791680A7/fi not_active Application Discontinuation
- 1979-05-25 NL NL7904112BA patent/NL7904112A/xx not_active Application Discontinuation
- 1979-05-25 DE DE2921324A patent/DE2921324C2/de not_active Expired

Also Published As

Publication number	Publication date
AU4689879A (en)	1979-11-29
NL7904112A (nl)	1979-11-28
US4229348A (en)	1980-10-21
NO791687L (no)	1979-11-27
IT1120970B (it)	1986-03-26
IT7968103A0 (it)	1979-05-24
GB2021576A (en)	1979-12-05
HU176076B (en)	1980-12-28
IL57264A0 (en)	1979-09-30
FI791680A7 (fi)	1979-11-27
GB2021576B (en)	1982-09-29
DK179579A (da)	1979-11-27
DE2921324A1 (de)	1979-11-29
PT69665A (pt)	1979-06-01
CA1133896A (fr)	1982-10-19
FR2426691A1 (fr)	1979-12-21
DE2921324C2 (de)	1983-02-10
FR2426691B1 (fr)	1982-04-02

Publication	Publication Date	Title
DE69305322T2 (de)	1997-02-20	Salpetersäureester von 2-(2,6-dihalophenylamino)phenylessigsäurederivaten und verfahren zu ihrer herstellung
DE2903612C2 (fr)	1988-12-22
DE1795763A1 (de)	1974-11-21	Verfahren zur herstellung von desacylierten vielkernigen indolverbindungen sowie deren estern
DE2228012B2 (de)	1979-05-23	-Aminophenylacetamido] -penicülansäure und Verfahren zu seiner Herstellung
DE1568621B2 (de)	1975-01-30	Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende herbizide Mittel
DD148055A5 (de)	1981-05-06	Verfahren zur herstellung von o-substituierten derivaten des(+)-cyanidan-3-ols
EP0048911B1 (fr)	1984-12-05	Oximes o-substituées dérivées de l'acide alpha-cétocarboxylique, procédé de préparation et médicaments qui les contiennent
DD143259A5 (de)	1980-08-13	Verfahren zur herstellung von penicillansaeurederivaten
DE2225149C2 (de)	1981-12-03	Oxofurylesterderivate der 6-(&aogon;-Aminophenylacetamido)penicillansäure, Verfahren zu deren Herstellung und ihre Verwendung
DE2640615A1 (de)	1977-03-17	Verfahren zur herstellung von n-acylierten hydroxyarylglycinderivaten und die dabei erhaltenen produkte
DE2809594A1 (de)	1979-09-20	Neue penicillinderivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE69932269T2 (de)	2006-11-23	Herstellung optisch aktiver Cyclohexylphenylglykolsäureester
DE2559913C2 (de)	1984-02-09	Verfahren zur Herstellung von Cephalosporinderivaten
DE2325498A1 (de)	1973-12-06	Penicillinverbindungen und verfahren zu ihrer herstellung
DE69303333T2 (de)	1996-11-21	Substituierte Benzoate-Derivate
CH522651A (de)	1972-05-15	Verfahren zur Herstellung von Nitroimidazolcarbamaten bzw.-thiocarbamaten
DE2925302C2 (de)	1984-01-19	Acylureidocephalosporinderivate und ihre Verwendung
DD152130A5 (de)	1981-11-18	Verfahren zur herstellung von penicillansaeurederivaten
DD295162A5 (de)	1991-10-24	Verfahren zur herstellung von d-alpha-(4-ethyl-2,3-dioxo-piperazin-1-carbonylamino)-benzylpenicillin
BE876466A (fr)	1979-11-23	Derive de l'acide penicillanique et son procede de preparation
DE3137376C2 (de)	1986-02-27	Verfahren zur Herstellung von 1,5-Alkylen-3-aryl-hydantoin-Derivaten
AT264537B (de)	1968-09-10	Verfahren zur Herstellung von 7-Amino-3-desacetyloxymethyl-3-formyl-isocephalosporansäureverbindungen und ihren Salzen
AT400844B (de)	1996-03-25	Abreicherungsverfahren des e-isomeren in z/e-7-amino-3-(2-(4-methyl-5-thiazolyl)vinyl)-3 cephem-4-carbonsäure
AT340587B (de)	1977-12-27	Verfahren zur herstellung neuer cephemderivate
EP0184732A2 (fr)	1986-06-18	Utilisation d'alcoyl esters de N-maléinyl-phénylalanine et procédé de leur préparation