CA1134298A - COMPOSE ANTIBIOTIQUE DE .beta.-LACTAM, PRODUCTION ET UTILISATION COMME AGENT ANTIMICROBIEN - Google Patents

COMPOSE ANTIBIOTIQUE DE .beta.-LACTAM, PRODUCTION ET UTILISATION COMME AGENT ANTIMICROBIEN

Info

Publication number: CA1134298A
Authority: CA; Canada
Prior art keywords: ene; oxo; hept; azabicyclo; carboxylate
Prior art date: 1978-11-01
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

CA383,283A

Other languages

English (en)

Inventor

Yasuyuki Kato

Kaoru Yamada

Tomoyuki Ishikura

Yasutaka Shimauchi

Takeo Yoshioka

Kenichi Yamamoto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanraku Ocean Co Ltd

Original Assignee

Sanraku Ocean Co Ltd

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

1978-11-01

Filing date

1981-08-05

Publication date

1982-10-26

1978-11-01 Priority claimed from JP13377378A external-priority patent/JPS5562088A/ja

1979-07-27 Priority claimed from JP9489179A external-priority patent/JPS5622787A/ja

1979-10-31 Priority claimed from CA000338878A external-priority patent/CA1142867A/fr

1981-08-05 Application filed by Sanraku Ocean Co Ltd filed Critical Sanraku Ocean Co Ltd

1981-08-05 Priority to CA383,283A priority Critical patent/CA1134298A/fr

1982-10-26 Application granted granted Critical

1982-10-26 Publication of CA1134298A publication Critical patent/CA1134298A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 24
230000003115 biocidal effect Effects 0.000 title abstract description 60
239000004599 antimicrobial Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 154
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 75
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
-1 compound p-nitrobenzyl 3-(2-acetamidoethylsulfinyl)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical class 0.000 claims description 80
238000000034 method Methods 0.000 claims description 58
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 21
239000000126 substance Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 10
244000005700 microbiome Species 0.000 claims description 8
238000007254 oxidation reaction Methods 0.000 claims description 7
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 6
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238000005886 esterification reaction Methods 0.000 claims description 5
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JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 4
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YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 3
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QJUDAQJJOGPBKD-UHFFFAOYSA-N (4-nitrophenyl)methyl 3-(2-acetamidoethylsulfanyl)-7-oxo-6-propan-2-yl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound N12C(=O)C(C(C)C)C2CC(SCCNC(C)=O)=C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QJUDAQJJOGPBKD-UHFFFAOYSA-N 0.000 claims 1
YYZHSGVQRIXRDQ-UHFFFAOYSA-N (4-nitrophenyl)methyl 3-(2-acetamidoethylsulfinyl)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound N12C(=O)C(CC)C2CC(S(=O)CCNC(C)=O)=C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 YYZHSGVQRIXRDQ-UHFFFAOYSA-N 0.000 claims 1
UEFPBOANMBFLNT-UHFFFAOYSA-N (4-nitrophenyl)methyl 3-(2-acetamidoethylsulfinyl)-7-oxo-6-propan-2-yl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound N12C(=O)C(C(C)C)C2CC(S(=O)CCNC(C)=O)=C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 UEFPBOANMBFLNT-UHFFFAOYSA-N 0.000 claims 1
YQIHGZPREMIHOC-UHFFFAOYSA-N benzhydryl 3-(2-acetamidoethylsulfanyl)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound N12C(=O)C(CC)C2CC(SCCNC(C)=O)=C1C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 YQIHGZPREMIHOC-UHFFFAOYSA-N 0.000 claims 1
CEPJMJAPRCYKRI-UHFFFAOYSA-N benzhydryl 3-(2-acetamidoethylsulfinyl)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound N12C(=O)C(CC)C2CC(S(=O)CCNC(C)=O)=C1C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 CEPJMJAPRCYKRI-UHFFFAOYSA-N 0.000 claims 1
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 59
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101150041968 CDC13 gene Proteins 0.000 description 53
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 52
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239000000203 mixture Substances 0.000 description 36
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150000003839 salts Chemical class 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
MHSNTZYKSLYGOM-RKDXNWHRSA-N PS-5 Chemical compound C1C(SCCNC(C)=O)=C(C(O)=O)N2C(=O)[C@H](CC)[C@H]21 MHSNTZYKSLYGOM-RKDXNWHRSA-N 0.000 description 31
239000008363 phosphate buffer Substances 0.000 description 30
SUMQHCXEWHRKGG-MWLCHTKSSA-N PS-6 Chemical compound C1C(SCCNC(C)=O)=C(C(O)=O)N2C(=O)[C@H](C(C)C)[C@H]21 SUMQHCXEWHRKGG-MWLCHTKSSA-N 0.000 description 29
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
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239000011734 sodium Substances 0.000 description 23
239000003826 tablet Substances 0.000 description 23
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 22
239000002904 solvent Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000012360 testing method Methods 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000007864 aqueous solution Substances 0.000 description 18
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230000002829 reductive effect Effects 0.000 description 17
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XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000003242 anti bacterial agent Substances 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
229940088710 antibiotic agent Drugs 0.000 description 14
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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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 11
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239000008101 lactose Substances 0.000 description 11
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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 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
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SUMQHCXEWHRKGG-UHFFFAOYSA-N Antibiotic PS 6 Natural products C1C(SCCNC(C)=O)=C(C(O)=O)N2C(=O)C(C(C)C)C21 SUMQHCXEWHRKGG-UHFFFAOYSA-N 0.000 description 7
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SHFGJEQAOUMGJM-UHFFFAOYSA-N dialuminum dipotassium disodium dioxosilane iron(3+) oxocalcium oxomagnesium oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Na+].[Na+].[Al+3].[Al+3].[K+].[K+].[Fe+3].[Fe+3].O=[Mg].O=[Ca].O=[Si]=O SHFGJEQAOUMGJM-UHFFFAOYSA-N 0.000 description 4
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MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
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TXRBBCHUDHOJCP-UHFFFAOYSA-M sodium;6-ethyl-3-(4-hydroxybutylsulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].C1C(SCCCCO)=C(C([O-])=O)N2C(=O)C(CC)C21 TXRBBCHUDHOJCP-UHFFFAOYSA-M 0.000 description 1
UFPSVZOMBSEMAA-UHFFFAOYSA-M sodium;6-ethyl-7-oxo-3-phenylsulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].[O-]C(=O)C=1N2C(=O)C(CC)C2CC=1SC1=CC=CC=C1 UFPSVZOMBSEMAA-UHFFFAOYSA-M 0.000 description 1
VTLWRSNWWLIJTQ-UHFFFAOYSA-M sodium;butane-1-thiolate Chemical compound [Na+].CCCC[S-] VTLWRSNWWLIJTQ-UHFFFAOYSA-M 0.000 description 1
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
150000003512 tertiary amines Chemical class 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000012137 tryptone Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA383,283A 1978-11-01 1981-08-05 COMPOSE ANTIBIOTIQUE DE .beta.-LACTAM, PRODUCTION ET UTILISATION COMME AGENT ANTIMICROBIEN Expired CA1134298A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA383,283A CA1134298A (fr)	1978-11-01	1981-08-05	COMPOSE ANTIBIOTIQUE DE .beta.-LACTAM, PRODUCTION ET UTILISATION COMME AGENT ANTIMICROBIEN

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP13377378A JPS5562088A (en)	1978-11-01	1978-11-01	Novel beta-lactam derivative and its intermediate
JP133,773		1978-11-01
JP9489179A JPS5622787A (en)	1979-07-27	1979-07-27	Beta-lactam compound
JP94,891		1979-07-27
CA000338878A CA1142867A (fr)	1978-11-01	1979-10-31	COMPOSE DE .beta.-LACTAM ANTIBIOTIQUE, PROCEDE DE PRODUCTION ET APPLICATION COMME AGENT ANTIMICROBIEN
CA383,283A CA1134298A (fr)	1978-11-01	1981-08-05	COMPOSE ANTIBIOTIQUE DE .beta.-LACTAM, PRODUCTION ET UTILISATION COMME AGENT ANTIMICROBIEN

Publications (1)

Publication Number	Publication Date
CA1134298A true CA1134298A (fr)	1982-10-26

Family

ID=27426191

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA383,283A Expired CA1134298A (fr)	1978-11-01	1981-08-05	COMPOSE ANTIBIOTIQUE DE .beta.-LACTAM, PRODUCTION ET UTILISATION COMME AGENT ANTIMICROBIEN

Country Status (1)

Country	Link
CA (1)	CA1134298A (fr)

1981
- 1981-08-05 CA CA383,283A patent/CA1134298A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-10-26	MKEX	Expiry

Publication	Publication Date	Title
EP0072710B1 (fr)	1986-02-19	Dérivés de Carbapénème, leur préparation et compositions les contenant
CA1142867A (fr)	1983-03-15	COMPOSE DE .beta.-LACTAM ANTIBIOTIQUE, PROCEDE DE PRODUCTION ET APPLICATION COMME AGENT ANTIMICROBIEN
CA1164460A (fr)	1984-03-27	Composes de beta-lactam et procede de production
US4189493A (en)	1980-02-19	N-heterocyclic derivatives of thienamycin
US5583218A (en)	1996-12-10	Carbapenem derivatives
EP0001567B1 (fr)	1981-12-02	Antibiotiques PS-6 et PS-7 apparentés à la thiénamycine, procédé pour leur préparation et compositions les contenant
CA1123767A (fr)	1982-05-18	Ps-5 antibiotique et derives inhibiteurs de la beta-lactamase et production dudit antibiotique
US4374144A (en)	1983-02-15	β-Lactam compounds, their preparation and use
EP0017970B1 (fr)	1982-07-07	Dérivés de bêta-lactame et procédé pour leur préparation
EP0273747B1 (fr)	1994-12-07	Dérivés de pénème, leur préparation et leur application
EP0061231A1 (fr)	1982-09-29	Procédé pour la préparation de dérivés de l'azabicyclo-(3.2.0) heptène-2
DE2652679C2 (fr)	1990-03-01
DE3650221T2 (de)	1995-06-22	Penemderivate.
US4426390A (en)	1984-01-17	Novel β-lactam compounds, process for producing thereof, and use thereof as medicines
GB2105329A (en)	1983-03-23	Penem-3-carboxylic acid derivatives their preparation and their use as antimicrobial agents
CA1260945A (fr)	1989-09-26	Antibiotiques de carbapenem
GB1570987A (en)	1980-07-09	Thienamycin derivatives
GB2118183A (en)	1983-10-26	Carbapenem antibiotics
GB1570986A (en)	1980-07-09	Derivatives of thienamycin and its isomers
Nakayama et al.	1983	New β-lactam antibiotics, carpetimycins C and D
US4387052A (en)	1983-06-07	Antibiotic PA-39504-X3 and production thereof
CH661730A5 (de)	1987-08-14	Penemcarbonsaeuren und verfahren zu deren herstellung.
DE3880660T2 (de)	1993-09-23	In 2-stellung substituierte (1r,5s,6s)-2-thio-6-((r)-1-hydroxyethyl)-1-methyl-carbapenem-carbonsaeure-derivate.
GB2180238A (en)	1987-03-25	Carbapenem antibiotics
Basker et al.	1983	Comparative biological properties of some synthetic olivanic acid analogues