KR830001903B1 - 페니실란산유도체의 제조방법 - Google Patents

페니실란산유도체의 제조방법 Download PDF

Info

Publication number: KR830001903B1
Authority: KR; South Korea
Prior art keywords: compound; amino; acid; ethyl acetate; mmol
Prior art date: 1979-02-13
Legal status (The legal status 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 status listed.): Expired

Application number

KR1019800000546A

Other languages

English (en)

Korean (ko)

Other versions

KR830001947A (ko

Inventor

올르 고츠프레드센 와근

본 대느 웰프

Original Assignee

레오 파마슈티칼 프로덕츠 리미티드

에르링그 쥬을 니엘슨

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.)

1979-02-13

Filing date

1980-02-12

Publication date

1983-09-19

1980-02-12 Application filed by 레오 파마슈티칼 프로덕츠 리미티드, 에르링그 쥬을 니엘슨 filed Critical 레오 파마슈티칼 프로덕츠 리미티드

1983-05-21 Publication of KR830001947A publication Critical patent/KR830001947A/ko

1983-09-19 Application granted granted Critical

1983-09-19 Publication of KR830001903B1 publication Critical patent/KR830001903B1/ko

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 133
-1 silane ester Chemical class 0.000 claims description 90
239000002253 acid Substances 0.000 claims description 51
229930182555 Penicillin Natural products 0.000 claims description 20
229940049954 penicillin Drugs 0.000 claims description 14
239000003781 beta lactamase inhibitor Substances 0.000 claims description 13
229940126813 beta-lactamase inhibitor Drugs 0.000 claims description 13
230000007062 hydrolysis Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
229910000077 silane Inorganic materials 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000003460 beta-lactamyl group Chemical group 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
150000001768 cations Chemical class 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
238000007327 hydrogenolysis reaction Methods 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 162
239000000203 mixture Substances 0.000 description 79
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 63
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
229940093499 ethyl acetate Drugs 0.000 description 54
235000019439 ethyl acetate Nutrition 0.000 description 54
239000000243 solution Substances 0.000 description 40
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 39
238000000034 method Methods 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
239000003921 oil Substances 0.000 description 33
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 31
229960003975 potassium Drugs 0.000 description 31
229910052700 potassium Inorganic materials 0.000 description 31
239000011591 potassium Substances 0.000 description 31
239000008346 aqueous phase Substances 0.000 description 30
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 30
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
238000003756 stirring Methods 0.000 description 20
150000003839 salts Chemical class 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 16
238000009472 formulation Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
238000004440 column chromatography Methods 0.000 description 13
239000013078 crystal Substances 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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 12
229960000723 ampicillin Drugs 0.000 description 12
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 12
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 11
239000003054 catalyst Substances 0.000 description 11
239000000543 intermediate Substances 0.000 description 11
239000000843 powder Substances 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
102000006635 beta-lactamase Human genes 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
239000000047 product Substances 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
108090000204 Dipeptidase 1 Proteins 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000007788 liquid Substances 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
150000002960 penicillins Chemical class 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
OPYGFNJSCUDTBT-PMLPCWDUSA-N sultamicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)OCOC(=O)[C@H]2C(S(=O)(=O)[C@H]3N2C(C3)=O)(C)C)(C)C)=CC=CC=C1 OPYGFNJSCUDTBT-PMLPCWDUSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000003480 eluent Substances 0.000 description 6
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
235000015497 potassium bicarbonate Nutrition 0.000 description 6
229910000028 potassium bicarbonate Inorganic materials 0.000 description 6
239000011736 potassium bicarbonate Substances 0.000 description 6
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
235000009518 sodium iodide Nutrition 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
238000007865 diluting Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
230000002000 scavenging effect Effects 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 5
210000002700 urine Anatomy 0.000 description 5
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
241001465754 Metazoa Species 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
239000002585 base Substances 0.000 description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 4
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
229940086066 potassium hydrogencarbonate Drugs 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 3
229930186147 Cephalosporin Natural products 0.000 description 3
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 3
208000035473 Communicable disease Diseases 0.000 description 3
208000022362 bacterial infectious disease Diseases 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
239000000969 carrier Substances 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
150000001780 cephalosporins Chemical class 0.000 description 3
PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
230000029142 excretion Effects 0.000 description 3
210000001035 gastrointestinal tract Anatomy 0.000 description 3
239000010410 layer Substances 0.000 description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
239000012925 reference material Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 3
RYAGQMSEMGVLGY-UHFFFAOYSA-N 1-chloro-1-iodoethane Chemical compound CC(Cl)I RYAGQMSEMGVLGY-UHFFFAOYSA-N 0.000 description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000003973 alkyl amines 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
239000011230 binding agent Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
PJBIHXWYDMFGCV-UHFFFAOYSA-N chloro(chlorosulfonyloxy)methane Chemical compound ClCOS(Cl)(=O)=O PJBIHXWYDMFGCV-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229940090805 clavulanate Drugs 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
235000013305 food Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
230000007774 longterm Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229960003085 meticillin Drugs 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000008024 pharmaceutical diluent Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000012730 sustained-release form Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
125000004665 trialkylsilyl group Chemical group 0.000 description 2
229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 2
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
VTNDHSZKSSVBGD-TYNCELHUSA-N (2s,5r,6r)-6-[(3-carboxyquinoxaline-2-carbonyl)amino]-3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1=CC=C2N=C(C(O)=O)C(C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4(=O)=O)(C)C)C(O)=O)=NC2=C1 VTNDHSZKSSVBGD-TYNCELHUSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OBQPKGCVMCIETH-UHFFFAOYSA-N 1-chloro-1-(1-chloroethoxy)ethane Chemical compound CC(Cl)OC(C)Cl OBQPKGCVMCIETH-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
108010087765 Antipain Proteins 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
108020004256 Beta-lactamase Proteins 0.000 description 1
208000031462 Bovine Mastitis Diseases 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
241000590988 Danainae Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-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
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-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
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
206010034133 Pathogen resistance Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
JIADKDBYMRAFHF-UHFFFAOYSA-N [As].C1=CC=CC=C1 Chemical compound [As].C1=CC=CC=C1 JIADKDBYMRAFHF-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
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 1
229960003022 amoxicillin Drugs 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000000954 anitussive effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
SDNYTAYICBFYFH-TUFLPTIASA-N antipain Chemical compound NC(N)=NCCC[C@@H](C=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 SDNYTAYICBFYFH-TUFLPTIASA-N 0.000 description 1
239000003434 antitussive agent Substances 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000003939 benzylamines Chemical class 0.000 description 1
239000003782 beta lactam antibiotic agent Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
ZYASDBCEYAHPMS-UHFFFAOYSA-N bis(chloromethyl) sulfate Chemical compound ClCOS(=O)(=O)OCCl ZYASDBCEYAHPMS-UHFFFAOYSA-N 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
208000030270 breast disease Diseases 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
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 1
229960003669 carbenicillin Drugs 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
SWYHWRRXAKMZLK-UHFFFAOYSA-N chloromethyl thiohypochlorite Chemical compound ClCSCl SWYHWRRXAKMZLK-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229960003324 clavulanic acid Drugs 0.000 description 1
238000002648 combination therapy Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
RUXBQPVRMIMAJE-UHFFFAOYSA-N hydroxy(oxo)silicon Chemical compound O[Si]=O RUXBQPVRMIMAJE-UHFFFAOYSA-N 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000008176 lyophilized powder Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
229940124583 pain medication Drugs 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000008063 pharmaceutical solvent Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
WVULZDFWPQCPPJ-UHFFFAOYSA-N potassium;hydrochloride Chemical compound Cl.[K] WVULZDFWPQCPPJ-UHFFFAOYSA-N 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 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
238000011084 recovery Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
210000005239 tubule Anatomy 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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
- 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
- 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)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

KR1019800000546A 1979-02-13 1980-02-12 페니실란산유도체의 제조방법 Expired KR830001903B1 (ko)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB5020/79		1979-02-13
GB7905020		1979-02-13
GB05020/79		1979-02-13

Publications (2)

Publication Number	Publication Date
KR830001947A KR830001947A (ko)	1983-05-21
KR830001903B1 true KR830001903B1 (ko)	1983-09-19

Family

ID=10503160

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1019800000546A Expired KR830001903B1 (ko)	1979-02-13	1980-02-12	페니실란산유도체의 제조방법

Country Status (4)

Country	Link
JP (2)	JPS55113790A (zh)
KR (1)	KR830001903B1 (zh)
BE (1)	BE881675A (zh)
ZA (1)	ZA80796B (zh)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4714761A (en) *	1979-03-05	1987-12-22	Pfizer Inc.	6,6-dihalopenicillanic acid 1,1-dioxides and process
US4420426A (en)	1979-03-05	1983-12-13	Pfizer Inc.	6-Alpha-halopenicillanic acid 1,1-dioxides
US4244951A (en) *	1979-05-16	1981-01-13	Pfizer Inc.	Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide
US4309347A (en)	1979-05-16	1982-01-05	Pfizer Inc.	Penicillanoyloxymethyl penicillanate 1,1,1',1'-tetraoxide
US4364957A (en)	1979-09-26	1982-12-21	Pfizer Inc.	Bis-esters of alkanediols as antibacterial agents
US4432970A (en) *	1979-11-23	1984-02-21	Pfizer Inc.	6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors
IE51516B1 (en) *	1980-10-06	1987-01-07	Leo Pharm Prod Ltd	1,1-dioxapenicillanoyloxymethyl 6-(d-alpha-amino-alpha-phenylacetamido)penicillanate napsylate
IL64009A (en) *	1980-10-31	1984-09-30	Rech Applications Therap	Crystalline 1,1-dioxopenicillanoyloxymethyl 6-(d-alpha-amino-alpha-phenylacetamido)penicillanate tosylate hydrates,their production and pharmaceutical compositions containing them
US4478748A (en) *	1981-02-20	1984-10-23	Pfizer Inc.	Bis-esters of alkanediols
HU196412B (en) *	1981-03-23	1988-11-28	Pfizer	Process for production of penicillin-acid-penicillakiroloximethil-esthers
US4381263A (en)	1981-03-23	1983-04-26	Pfizer Inc.	Process for the preparation of penicillanic acid esters
US4419284A (en) *	1981-03-23	1983-12-06	Pfizer Inc.	Preparation of halomethyl esters (and related esters) of penicillanic acid 1,1-dioxide
IN159362B (zh) *	1981-03-23	1987-05-09	Pfizer
JPS5857384A (ja) *	1981-09-09	1983-04-05	フアイザ−・インコ−ポレ−テツド	抗菌性のペニシラン酸６′‐（２‐アミノ‐２‐〔４‐アシルオキシフェニル〕アセタミド）ペニシラノイルオキシメチル１，１‐ジオキシド化合物
US4540687A (en) *	1981-09-09	1985-09-10	Pfizer Inc.	Antibacterial 6'-(2-amino-2-[4-acyloxyphenyl]acetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds
US4582829A (en) *	1981-09-09	1986-04-15	Pfizer Inc.	Antibacterial 6'-(2-amino-2-[4-acyloxyphenyl]acetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds
US4351840A (en) *	1981-09-18	1982-09-28	Pfizer Inc.	Antibacterial esters of resorcinol with ampicillin and penicillanic acid 1,1-dioxide derivatives
US4359472A (en) *	1981-12-22	1982-11-16	Pfizer Inc.	Bis-hydroxymethyl carbonate bridged antibacterial agents
US4444686A (en) *	1982-01-25	1984-04-24	Pfizer Inc.	Crystalline penicillin ester intermediate
US4432987A (en) *	1982-04-23	1984-02-21	Pfizer Inc.	Crystalline benzenesulfonate salts of sultamicillin
PH20068A (en) *	1982-12-06	1986-09-18	Pfizer	Process and intermediates for sultamicillin and analogs
US4835674A (en) *	1986-07-28	1989-05-30	Bull Hn Information Systems Inc.	Computer network system for multiple processing elements
KR20020028298A (ko) *	2000-10-09	2002-04-17	황해용	초배지 및 그 제조장치
DE102004021281A1 (de) *	2004-04-29	2005-11-24	Boehringer Ingelheim Vetmedica Gmbh	Verwendung von Meloxicam-Formulierungen in der Veterinärmedizin

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1578128A (en) *	1976-03-30	1980-11-05	Leo Pharm Prod Ltd	Amidinopenicillanoyloxyalkyl amoxycillinates

1980
- 1980-02-12 BE BE0/199363A patent/BE881675A/fr not_active IP Right Cessation
- 1980-02-12 ZA ZA00800796A patent/ZA80796B/xx unknown
- 1980-02-12 KR KR1019800000546A patent/KR830001903B1/ko not_active Expired
- 1980-02-13 JP JP1719780A patent/JPS55113790A/ja active Granted
1987
- 1987-05-11 JP JP62114399A patent/JPS62281879A/ja active Granted

Also Published As

Publication number	Publication date
JPH0470315B2 (zh)	1992-11-10
JPS55113790A (en)	1980-09-02
ZA80796B (en)	1981-02-25
JPS62281879A (ja)	1987-12-07
JPS6259709B2 (zh)	1987-12-12
BE881675A (fr)	1980-08-12
KR830001947A (ko)	1983-05-21

Publication	Publication Date	Title
KR830001903B1 (ko)	1983-09-19	페니실란산유도체의 제조방법
US4342772A (en)	1982-08-03	β-Lactam compounds, antibacterial compositions thereof and method of use
JPH0222076B2 (zh)	1990-05-17
US4189493A (en)	1980-02-19	N-heterocyclic derivatives of thienamycin
JPH0662529B2 (ja)	1994-08-17	アミノ酸誘導体
JPH0140837B2 (zh)	1989-08-31
ES2218557T3 (es)	2004-11-16	Derivados del acido 7-alquilideno cefalosporanico y metodos para su utilizacion.
JPS62283974A (ja)	1987-12-09	置換６−ヒドロキシメチル−カルバペネム抗生物質
FR2585704A1 (fr)	1987-02-06	Alkylcarbamoyloxymethylcephemes
JPH0819135B2 (ja)	1996-02-28	安定なオキサペネム‐３‐カルボン酸
DE69016719T2 (de)	1995-06-01	Cephalosporinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate und Zwischenverbindungen.
IE45559B1 (en)	1982-09-22	Lactam antibiotics
US4277482A (en)	1981-07-07	3-Substituted thio-6-amido-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid s-oxides
SU1015830A3 (ru)	1983-04-30	Способ получени сложных эфиров 6-амидинопенициллановых кислот или их аддитивных солей с кислотами и его вариант
NZ230827A (en)	1991-05-28	Pharmaceutical composition containing an oxapenem-3-carboxylic acid derivative as beta-lactamase inhibitor
LU86678A1 (fr)	1987-06-26	Carbapenemes portant en position 2 un substituant heterothioalcoylthio quaternise
US4407751A (en)	1983-10-04	Processes for preparing β-lactams
US4372965A (en)	1983-02-08	6-, 1- And 2-substituted-thio-1-carbadethiapen-2-em-3-carboxylic acid S-oxides
JP3148235B2 (ja)	2001-03-19	抗菌性ペネム化合物
JPS59199693A (ja)	1984-11-12	インドリルグリシルセフアロスポリン誘導体
KR830001902B1 (ko)	1983-09-19	폐니실란산유도체의 제조방법
US4341791A (en)	1982-07-27	6-, 2- and 1,1-Disubstituted-1-carbadethiapen-2-em-3-carboxylic acid S-oxides
GB2157284A (en)	1985-10-23	6- beta -halopenicillanic acid salts
GB2144126A (en)	1985-02-27	Penem carboxylix acids and the preparation thereof
JPH0414679B2 (zh)	1992-03-13

Legal Events

Date	Code	Title	Description
1980-02-12	PA0109	Patent application	Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19800212
1983-05-19	PG1501	Laying open of application
1983-09-19	PG1605	Publication of application before grant of patent	Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19830819
1983-12-05	PE0701	Decision of registration	Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19831205
1983-12-13	PR0701	Registration of establishment	Comment text: Registration of Establishment Patent event date: 19831213 Patent event code: PR07011E01D
1983-12-13	PR1002	Payment of registration fee	Payment date: 19831213 End annual number: 3 Start annual number: 1
1986-07-08	PR1001	Payment of annual fee	Payment date: 19860708 Start annual number: 4 End annual number: 4
1987-07-08	PR1001	Payment of annual fee	Payment date: 19870708 Start annual number: 5 End annual number: 5
1988-07-08	PR1001	Payment of annual fee	Payment date: 19880708 Start annual number: 6 End annual number: 6
1989-07-10	PR1001	Payment of annual fee	Payment date: 19890710 Start annual number: 7 End annual number: 7
1990-07-30	PR1001	Payment of annual fee	Payment date: 19900730 Start annual number: 8 End annual number: 8
1991-07-09	PR1001	Payment of annual fee	Payment date: 19910709 Start annual number: 9 End annual number: 9
1992-07-11	PR1001	Payment of annual fee	Payment date: 19920711 Start annual number: 10 End annual number: 10
1993-07-13	PR1001	Payment of annual fee	Payment date: 19930713 Start annual number: 11 End annual number: 11
1994-07-19	PR1001	Payment of annual fee	Payment date: 19940719 Start annual number: 12 End annual number: 12
1995-02-13	PC1801	Expiration of term