DD152561A5 - Verfahren zur herstellung von penizillinderivaten - Google Patents

Verfahren zur herstellung von penizillinderivaten Download PDF

Info

Publication number: DD152561A5
Authority: DD; German Democratic Republic
Prior art keywords: group; formula; compound; reaction; protected
Prior art date: 1979-04-11

Application number

DD80220392A

Other languages

German (de)

English (en)

Other versions

DD152561B2 (de

Inventor

Eiji Ohki

Sadao Oida

Akira Yoshida

Teruo Hayashi

Shinichi Sugawara

Original Assignee

Eiji Ohki

Sadao Oida

Akira Yoshida

Teruo Hayashi

Shinichi Sugawara

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.)

1979-04-11

Filing date

1980-04-11

Publication date

1981-12-02

1980-04-11 Application filed by Eiji Ohki, Sadao Oida, Akira Yoshida, Teruo Hayashi, Shinichi Sugawara filed Critical Eiji Ohki

1981-12-02 Publication of DD152561B2 publication Critical patent/DD152561B2/xx

1981-12-02 Publication of DD152561A5 publication Critical patent/DD152561A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 38
238000002360 preparation method Methods 0.000 title claims abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 114
150000002960 penicillins Chemical class 0.000 claims abstract description 24
150000002148 esters Chemical class 0.000 claims abstract description 17
125000006239 protecting group Chemical group 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 15
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims abstract description 9
230000015572 biosynthetic process Effects 0.000 claims abstract 2
230000032050 esterification Effects 0.000 claims abstract 2
238000005886 esterification reaction Methods 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 121
-1 benzhydryloxycarbonyl group Chemical group 0.000 claims description 72
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 14
125000003277 amino group Chemical group 0.000 claims description 12
230000002829 reductive effect Effects 0.000 claims description 12
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000001768 cations Chemical class 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 3
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
125000005389 trialkylsiloxy group Chemical group 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 2
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 2
SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 claims 1
125000004423 acyloxy group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000003115 biocidal effect Effects 0.000 abstract description 7
230000000694 effects Effects 0.000 abstract description 7
241000894006 Bacteria Species 0.000 abstract description 6
239000003242 anti bacterial agent Substances 0.000 abstract description 6
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 abstract description 5
241000589516 Pseudomonas Species 0.000 abstract description 5
229940088710 antibiotic agent Drugs 0.000 abstract description 5
230000008030 elimination Effects 0.000 abstract description 3
238000003379 elimination reaction Methods 0.000 abstract description 3
238000007363 ring formation reaction Methods 0.000 abstract description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 abstract description 3
241001465754 Metazoa Species 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
239000000203 mixture Substances 0.000 description 66
239000002904 solvent Substances 0.000 description 63
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 25
238000000862 absorption spectrum Methods 0.000 description 24
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
238000007796 conventional method Methods 0.000 description 18
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
229930182555 Penicillin Natural products 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
238000000921 elemental analysis Methods 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 12
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 11
235000011054 acetic acid Nutrition 0.000 description 11
239000002585 base Substances 0.000 description 11
239000007858 starting material Substances 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
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 10
239000003638 chemical reducing agent Substances 0.000 description 10
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
238000001816 cooling Methods 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
238000012746 preparative thin layer chromatography Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical class [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
125000003710 aryl alkyl group Chemical group 0.000 description 6
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000008363 phosphate buffer Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 5
230000002411 adverse Effects 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
239000007788 liquid Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
244000005700 microbiome Species 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 5
125000005496 phosphonium group Chemical group 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000000039 preparative column chromatography Methods 0.000 description 5
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
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 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000000470 constituent Substances 0.000 description 4
239000002274 desiccant Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229940049954 penicillin Drugs 0.000 description 4
150000003003 phosphines Chemical class 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
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 3
229960003669 carbenicillin Drugs 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
231100000989 no adverse effect Toxicity 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 description 3
125000002217 penem group Chemical group 0.000 description 3
235000019371 penicillin G benzathine Nutrition 0.000 description 3
229940056360 penicillin g Drugs 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000012989 trithiocarbonate Substances 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
HTSFUAPDRXCYDV-UHFFFAOYSA-N 4-(benzenesulfonyl)azetidin-2-one Chemical class N1C(=O)CC1S(=O)(=O)C1=CC=CC=C1 HTSFUAPDRXCYDV-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
GMKILTCHJLNKJJ-UHFFFAOYSA-N 4-sulfonylazetidin-2-one Chemical class O=C1CC(=S(=O)=O)N1 GMKILTCHJLNKJJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000588747 Klebsiella pneumoniae Species 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
241000228143 Penicillium Species 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
150000001340 alkali metals Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
150000001451 organic peroxides Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
150000002961 penems Chemical class 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
241000894007 species Species 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
OIHLWKOVIJPVHC-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-oxoacetate;hydrate Chemical compound O.[O-][N+](=O)C1=CC=C(COC(=O)C=O)C=C1 OIHLWKOVIJPVHC-UHFFFAOYSA-N 0.000 description 1
WZKJVDAVEBGOMU-UHFFFAOYSA-N (4-nitrophenyl)methyl n-(2-sulfanylethyl)carbamate Chemical compound [O-][N+](=O)C1=CC=C(COC(=O)NCCS)C=C1 WZKJVDAVEBGOMU-UHFFFAOYSA-N 0.000 description 1
OEYMQQDJCUHKQS-UHFFFAOYSA-N (4-oxoazetidin-2-yl) acetate Chemical compound CC(=O)OC1CC(=O)N1 OEYMQQDJCUHKQS-UHFFFAOYSA-N 0.000 description 1
DMEYZPJEFHGESJ-CPWLGJMPSA-M (5R,6Z)-6-(6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [O-]C(=O)C1=CS[C@H]2N1C(=O)\C2=C\C1=CN2CCOCC2=N1 DMEYZPJEFHGESJ-CPWLGJMPSA-M 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
PZBCENUAPNTHEM-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxyethanethiol Chemical compound CC(C)(C)[Si](C)(C)OCCS PZBCENUAPNTHEM-UHFFFAOYSA-N 0.000 description 1
UPYXKEAOXBAIFT-UHFFFAOYSA-N 3,4-dimethylazete-2-carboxamide Chemical compound CC1=C(C)C(C(N)=O)=N1 UPYXKEAOXBAIFT-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
OQVYMXCRDHDTTH-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)-2-[4-(diethoxyphosphorylmethyl)pyridin-2-yl]pyridine Chemical compound CCOP(=O)(OCC)CC1=CC=NC(C=2N=CC=C(CP(=O)(OCC)OCC)C=2)=C1 OQVYMXCRDHDTTH-UHFFFAOYSA-N 0.000 description 1
PMLNWWKKYGLTNQ-UHFFFAOYSA-N 4-methylsulfonylazetidin-2-one Chemical class CS(=O)(=O)C1CC(=O)N1 PMLNWWKKYGLTNQ-UHFFFAOYSA-N 0.000 description 1
IQVDSMUMVVBIQZ-UHFFFAOYSA-N 4-phenylsulfanylazetidin-2-one Chemical compound N1C(=O)CC1SC1=CC=CC=C1 IQVDSMUMVVBIQZ-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
101100356682 Caenorhabditis elegans rho-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
LPDCCJNPKJCPPR-UHFFFAOYSA-N ClC=1C(=C(C(=CC1)C(=O)OO)Cl)Cl Chemical compound ClC=1C(=C(C(=CC1)C(=O)OO)Cl)Cl LPDCCJNPKJCPPR-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
229910003317 GdCl3 Inorganic materials 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
241000147000 Shigella flexneri 2a Species 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
LQCYIQBYFCQMCH-UHFFFAOYSA-N [Li].C[Cu]C Chemical compound [Li].C[Cu]C LQCYIQBYFCQMCH-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 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
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
RCYUACIXZYDBGL-UHFFFAOYSA-N azetidine-2,3-dione Chemical compound O=C1CNC1=O RCYUACIXZYDBGL-UHFFFAOYSA-N 0.000 description 1
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
125000003460 beta-lactamyl group Chemical group 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000001934 cyclohexanes Chemical class 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical compound [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical class ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
MEANOSLIBWSCIT-UHFFFAOYSA-K gadolinium trichloride Chemical compound Cl[Gd](Cl)Cl MEANOSLIBWSCIT-UHFFFAOYSA-K 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910001503 inorganic bromide Inorganic materials 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
239000002075 main ingredient Substances 0.000 description 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
SWUGVGAANSBAQM-IMTBSYHQSA-N methyl 2-[(2r,3s)-3-bromo-2-methylsulfanyl-4-oxoazetidin-1-yl]-3-methylbut-2-enoate Chemical compound COC(=O)C(=C(C)C)N1[C@H](SC)[C@@H](Br)C1=O SWUGVGAANSBAQM-IMTBSYHQSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
239000001230 potassium iodate Substances 0.000 description 1
235000006666 potassium iodate Nutrition 0.000 description 1
229940093930 potassium iodate Drugs 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
102200016460 rs104894273 Human genes 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 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
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003952 β-lactams Chemical class 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
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

DD80220392A 1979-04-11 1980-04-11 Verfahren zur herstellung von penizillinderivaten DD152561A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4405079A JPS55153789A (en)	1979-04-11	1979-04-11	Penem-3-carboxylic acid derivative and its preparation

Publications (2)

Publication Number	Publication Date
DD152561B2 DD152561B2 (de)	1981-12-02
DD152561A5 true DD152561A5 (de)	1981-12-02

Family

ID=12680777

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80220392A DD152561A5 (de)	1979-04-11	1980-04-11	Verfahren zur herstellung von penizillinderivaten

Country Status (16)

Country	Link
JP (1)	JPS55153789A (fr)
AU (1)	AU5729180A (fr)
BE (1)	BE882764A (fr)
DD (1)	DD152561A5 (fr)
DE (1)	DE3013997A1 (fr)
DK (1)	DK154180A (fr)
ES (1)	ES490510A0 (fr)
FI (1)	FI801168A7 (fr)
FR (1)	FR2453862A1 (fr)
GB (1)	GB2048261A (fr)
IT (1)	IT8067576A0 (fr)
NL (1)	NL8002147A (fr)
NO (1)	NO801046L (fr)
PL (1)	PL223390A1 (fr)
SE (1)	SE8002708L (fr)
ZA (1)	ZA802155B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5625110A (en) *	1978-12-18	1981-03-10	Bristol Myers Co	Antibacterial
DE3176517D1 (en) *	1980-04-24	1987-12-17	Beecham Group Plc	Beta-lactam compounds, their preparation and use
JPS58198486A (ja) *	1982-05-14	1983-11-18	Sankyo Co Ltd	ペネムまたはカルバペネム−３−カルボン酸誘導体およびその製法
JPS5835190A (ja) *	1981-08-25	1983-03-01	Sankyo Co Ltd	ペネム−３−カルボン酸誘導体
JPS5857360A (ja) *	1981-10-01	1983-04-05	Ajinomoto Co Inc	アゼチジノン誘導体
CA1190236A (fr)	1981-10-23	1985-07-09	Edward J.J. Grabowski	Synthese d'un antibiotique
NL8204720A (nl) *	1981-12-11	1983-07-01	Erba Farmitalia	Werkwijze voor het bereiden van optisch actieve penemverbindingen.
US4431654A (en) *	1982-04-05	1984-02-14	Schering Corporation	6-(Hydroxyethyl)-2-[(heterocyclyl or aryl)thioalkylthio]-penem-3-carboxylates
EP0115308A3 (fr) *	1983-01-25	1984-10-10	Merck & Co. Inc.	Acides pen-2-em-3-carboxyliques 2-alkylthio non-substitués et procédé pour préparer des 2-thioxopénames substitués et des thiopénèmes 2-substitués
US4610823A (en) *	1983-01-25	1986-09-09	Merck & Co., Inc.	Process for preparing substituted 2-thioxopenams and 2-substituted thiopenems
US4504485A (en) *	1983-04-04	1985-03-12	Schering Corporation	5R,6S,8R-6-(1-Hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxylic acid
GB8321004D0 (en) *	1983-08-04	1983-09-07	Erba Farmitalia	Azetidinones
US5075439A (en) *	1990-08-17	1991-12-24	Pfizer Inc.	Processes for (3S,4R)-3-[1(R)-t-butyl-dimethylsilyloxy)-ethyl]-4-[1-oxo-3-thiolanylthio(thiocarbonyl)thio]azetidin-2-ones and intermediates therefor
GB2252769A (en) *	1991-01-18	1992-08-19	Pfizer	Improved process for azetidin-2-ones and intermediates therefor
GB9103034D0 (en) *	1991-02-13	1991-03-27	Fujisawa Pharmaceutical Co	Processes for preparing carbapenem derivatives
GB9913932D0 (en) *	1999-06-15	1999-08-18	Pfizer Ltd	Purine derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3950357A (en) *	1974-11-25	1976-04-13	Merck & Co., Inc.	Antibiotics
US4168314A (en) *	1977-11-17	1979-09-18	Merck & Co., Inc.	6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid
EP0003960B1 (fr) *	1978-02-02	1983-06-29	Ciba-Geigy Ag	Composés thia-aza substitués en position 6, leur préparation et compositions pharmaceutiques les contenant
IL59081A0 (en) *	1979-01-10	1980-05-30	Schering Corp	2-penem compounds and a method for preparing them

1979
- 1979-04-11 JP JP4405079A patent/JPS55153789A/ja active Granted
1980
- 1980-04-10 SE SE8002708A patent/SE8002708L/xx unknown
- 1980-04-10 DK DK154180A patent/DK154180A/da not_active IP Right Cessation
- 1980-04-10 ZA ZA00802155A patent/ZA802155B/xx unknown
- 1980-04-11 PL PL22339080A patent/PL223390A1/xx unknown
- 1980-04-11 BE BE0/200208A patent/BE882764A/fr unknown
- 1980-04-11 DE DE19803013997 patent/DE3013997A1/de not_active Withdrawn
- 1980-04-11 FR FR8008137A patent/FR2453862A1/fr not_active Withdrawn
- 1980-04-11 FI FI801168A patent/FI801168A7/fi not_active Application Discontinuation
- 1980-04-11 IT IT8067576A patent/IT8067576A0/it unknown
- 1980-04-11 NL NL8002147A patent/NL8002147A/xx not_active Application Discontinuation
- 1980-04-11 AU AU57291/80A patent/AU5729180A/en not_active Abandoned
- 1980-04-11 GB GB8012001A patent/GB2048261A/en not_active Withdrawn
- 1980-04-11 ES ES490510A patent/ES490510A0/es active Granted
- 1980-04-11 NO NO80801046A patent/NO801046L/no unknown
- 1980-04-11 DD DD80220392A patent/DD152561A5/de unknown

Also Published As

Publication number	Publication date
DD152561B2 (de)	1981-12-02
NL8002147A (nl)	1980-10-14
BE882764A (fr)	1980-10-13
ZA802155B (en)	1981-05-27
AU5729180A (en)	1980-10-16
GB2048261A (en)	1980-12-10
SE8002708L (sv)	1980-10-12
DE3013997A1 (de)	1980-10-30
IT8067576A0 (it)	1980-04-11
DK154180A (da)	1980-10-12
JPH0372630B2 (fr)	1991-11-19
PL223390A1 (fr)	1981-01-30
ES8202015A1 (es)	1981-04-16
ES490510A0 (es)	1981-04-16
NO801046L (no)	1980-10-13
FR2453862A1 (fr)	1980-11-07
FI801168A7 (fi)	1981-01-01
JPS55153789A (en)	1980-11-29

Legal Events

Date	Code	Title	Description
1981-12-02	C	Prov. exclusive patent (sect. 19)

Publication	Publication Date	Title
EP0003960B1 (fr)	1983-06-29	Composés thia-aza substitués en position 6, leur préparation et compositions pharmaceutiques les contenant
DE3587126T2 (de)	1993-10-07	Carbapenem-Derivate und sie enthaltende Zusammensetzung.
CH646173A5 (de)	1984-11-15	Thia-azaverbindungen mit beta-lactamring.
DD152339A5 (de)	1981-11-25	Verfahren zur herstellung von 2-penem-verbindungen
DE3013997A1 (de)	1980-10-30	Penem-3-carbonsaeurederivate, verfahren zu deren herstellung und pharmazeutische zusammensetzung
JPS61207387A (ja)	1986-09-13	抗菌剤
DE3122523C2 (fr)	1990-10-18
DE3109086A1 (de)	1981-12-24	2-penem-3-carbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung
EP0247431B1 (fr)	1990-08-01	Antibiotiques du 6-hydroxyméthylcarbapénème substitués, leur procédé de préparation et leur application
EP0301394B1 (fr)	1993-10-06	Acides oxapénèm-3-carboxyliques stables
AT395590B (de)	1993-01-25	2-methoxymethylpenemverbindungen, verfahren zu deren herstellung und sie enthaltende pharmazeutische zusammensetzungen
DE3750842T2 (de)	1995-05-18	Penem-Derivate, ihre Herstellung und Verwendung.
EP0195963A1 (fr)	1986-10-01	Procédé de préparation d'intermédiaires de carbapénème
EP0080162A1 (fr)	1983-06-01	Pénèmes 2-(fluoroalkylthio) substitués, procédés pour leur préparation et compositions pharmaceutiques les contenant
DE3201957A1 (de)	1982-09-09	Derivate der 7-oxo-1-azabicyclo-(3.2.0)-hept-2-en-2-carbonsaeure
DE3231596C2 (fr)	1989-03-09
EP0362622B1 (fr)	1995-03-29	Utilisation d'acides oxapenem-3-carboxyliques stables pour l'obtention d'un médicament destiné à l'inhibition de beta-lactamase
DE3245270A1 (de)	1983-06-23	Verfahren zur herstellung von optisch aktiven penemen
CH659072A5 (de)	1986-12-31	Penemderivate.
AT396472B (de)	1993-09-27	Verfahren zur herstellung neuer carbapenem-antibiotika
EP0023887B1 (fr)	1984-11-07	Dérivés d'azétidinone bicycliques substitués en 3, procédé pour leur préparation et intermédiaires ainsi que leur préparation
EP0170019A1 (fr)	1986-02-05	Carbapenems avec un groupe éther en position 4
EP0112283B1 (fr)	1987-08-12	Dérivés hétérocyclylthio, procédé pour leur préparation, compositions pharmaceutiques les contenant et leur application
CH643265A5 (en)	1984-05-30	Antibacterial penem compounds
EP0252885A1 (fr)	1988-01-13	Composés thia-aza-bicycliques