CA1205405A - Substances de potentialisation de l'activite des antibiotiques et methode de production - Google Patents

Substances de potentialisation de l'activite des antibiotiques et methode de production

Info

Publication number: CA1205405A
Authority: CA; Canada
Prior art keywords: compound; process according; formula; salt; chemical equivalent
Prior art date: 1982-02-15
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

CA000421538A

Other languages

English (en)

Inventor

Susumu Shinagawa

Akira Imada

Kazuhiko Kintaka

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.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries 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.)

1982-02-15

Filing date

1983-02-14

Publication date

1986-06-03

1982-02-15 Priority claimed from JP57023099A external-priority patent/JPS58141786A/ja

1982-12-24 Priority claimed from JP57232055A external-priority patent/JPS59118799A/ja

1983-02-14 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1986-06-03 Application granted granted Critical

1986-06-03 Publication of CA1205405A publication Critical patent/CA1205405A/fr

Status Expired legal-status Critical Current

Links

239000000126 substance Substances 0.000 title claims description 42
238000004519 manufacturing process Methods 0.000 title claims description 11
230000003389 potentiating effect Effects 0.000 title abstract description 10
230000000694 effects Effects 0.000 title description 15
239000003242 anti bacterial agent Substances 0.000 title description 9
229940088710 antibiotic agent Drugs 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims abstract description 54
150000003839 salts Chemical class 0.000 claims abstract description 18
229910006069 SO3H Inorganic materials 0.000 claims abstract 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 32
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 20
244000005700 microbiome Species 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 10
241000927377 Pseudomonas acidophila Species 0.000 claims description 8
241000083686 [Pseudomonas] mesoacidophila Species 0.000 claims description 8
159000000000 sodium salts Chemical class 0.000 claims description 7
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 4
229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
230000000844 anti-bacterial effect Effects 0.000 abstract description 10
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HJJDBAOLQAWBMH-YCRCPZNHSA-N cefmenoxime Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NN=NN1C HJJDBAOLQAWBMH-YCRCPZNHSA-N 0.000 description 29
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BWWVAEOLVKTZFQ-ISVUSNJMSA-N chembl530 Chemical compound N(/[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)=C\N1CCCCCC1 BWWVAEOLVKTZFQ-ISVUSNJMSA-N 0.000 description 13
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YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 9
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235000013372 meat Nutrition 0.000 description 9
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 9
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XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 6
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ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
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GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 5
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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238000003556 assay Methods 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
230000006399 behavior Effects 0.000 description 1
MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
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229960002685 biotin Drugs 0.000 description 1
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239000011616 biotin Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000002962 chemical mutagen Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
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 1
229960003324 clavulanic acid Drugs 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
229960003067 cystine Drugs 0.000 description 1
238000011033 desalting Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
208000020612 escherichia coli infection Diseases 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000005291 magnetic effect Effects 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
229960004452 methionine Drugs 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
230000035772 mutation Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002898 organic sulfur compounds Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920001521 polyalkylene glycol ether Polymers 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229960003080 taurine Drugs 0.000 description 1
FAKFSJNVVCGEEI-UHFFFAOYSA-J tin(4+);disulfate Chemical compound [Sn+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FAKFSJNVVCGEEI-UHFFFAOYSA-J 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1

Classifications

- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

CA000421538A 1982-02-15 1983-02-14 Substances de potentialisation de l'activite des antibiotiques et methode de production Expired CA1205405A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP23099/1982		1982-02-15
JP57023099A JPS58141786A (ja)	1982-02-15	1982-02-15	抗菌性増強物質ｆ３およびその製造法
JP232055/1982		1982-12-24
JP57232055A JPS59118799A (ja)	1982-12-24	1982-12-24	抗菌性増強物質およびその製造法

Publications (1)

Publication Number	Publication Date
CA1205405A true CA1205405A (fr)	1986-06-03

Family

ID=26360395

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000421538A Expired CA1205405A (fr)	1982-02-15	1983-02-14	Substances de potentialisation de l'activite des antibiotiques et methode de production

Country Status (1)

Country	Link
CA (1)	CA1205405A (fr)

1983
- 1983-02-14 CA CA000421538A patent/CA1205405A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2003-06-03	MKEX	Expiry

Publication	Publication Date	Title
US4460765A (en)	1984-07-17	Enzyme inhibitor produced by cultivation of streptomyces microorganisms
EP0182315B1 (fr)	1989-04-05	Antibiotique NK84-0218, compositions pharmaceutiques le contenant et procédé pour sa production
US4042683A (en)	1977-08-16	Rifamycins P, Q and U
US3923977A (en)	1975-12-02	Antibiotic FR-1923 substance
JPS6133558B2 (fr)	1986-08-02
CA1205405A (fr)	1986-06-03	Substances de potentialisation de l'activite des antibiotiques et methode de production
Martin et al.	1978	GLYCOCINNAMOYLSPERMIDINES, A NEW CLASS OF ANTIBIOTICS II. ISOLATION, PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES OF LL-BM123β, γ 1, AND γ 2
US3674866A (en)	1972-07-04	Moenomycin and process for producing same
EP0128505A2 (fr)	1984-12-19	Difficidine et ses dérivés antibactériens
NL8000628A (nl)	1980-08-05	Antibiotica c-19393s2 en h2.
EP0086610A1 (fr)	1983-08-24	Une substance renforçant l'activité des antibiotiques et sa production
EP0083375B1 (fr)	1987-05-20	Substance accroissant l'effet antibacterien et son procede de preparation
US4504655A (en)	1985-03-12	Substances potentiating the activity of antibiotics and their production
US4160026A (en)	1979-07-03	Antibiotics SF-1130-x1 and -x2 substances and production and use thereof
GB2084158A (en)	1982-04-07	Peptide and production thereof
EP0085859B1 (fr)	1986-04-09	Substance antibiotique AM-2604-A et son procédé de préparation
IL39302A (en)	1974-11-29	Antibiotic em-49
US4495286A (en)	1985-01-22	Antibiotic complex producing bacterial culture
EP0253413B1 (fr)	1993-10-13	Antibiotiques appelés "Mureidomycines A,B,C et D", leur procédé de préparation et leur emploi thérapeutique
US3927211A (en)	1975-12-16	Antibiotic MYC 8003 and process for producing same
US4036696A (en)	1977-07-19	Preparation of antibiotics by fermentation
US3814795A (en)	1974-06-04	Antibiotic s 15-1 and process for producing the same
US4427655A (en)	1984-01-24	Antibiotics-875A and production thereof
EP0144238B1 (fr)	1988-08-17	Composé FR-900451, sa production et son emploi
HK1003573A1 (en)	1998-10-30	New antibiotics of the mureidomycin group, their preparation, and their therapeutic use