CA1070675A - La polymyxinemethyltetracycline - Google Patents

La polymyxinemethyltetracycline

Info

Publication number: CA1070675A
Authority: CA; Canada
Prior art keywords: antibiotic; formula; salts; colistine; family
Prior art date: 1974-03-20
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

CA222,417A

Other languages

English (en)

Inventor

Pierre Niviere

Gerard A. Orillard

Jean Blum

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.)

Individual

Original Assignee

Individual

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.)

1974-03-20

Filing date

1975-03-18

Publication date

1980-01-29

1975-03-18 Application filed by Individual filed Critical Individual

1980-01-29 Application granted granted Critical

1980-01-29 Publication of CA1070675A publication Critical patent/CA1070675A/fr

Status Expired legal-status Critical Current

Links

239000004098 Tetracycline Substances 0.000 title claims abstract description 10
235000019364 tetracycline Nutrition 0.000 title claims abstract description 10
229960002180 tetracycline Drugs 0.000 title claims abstract description 9
229930101283 tetracycline Natural products 0.000 title claims abstract description 9
-1 methyl tetracycline Chemical class 0.000 title abstract description 6
108010040201 Polymyxins Proteins 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 14
230000003115 biocidal effect Effects 0.000 claims abstract description 13
YKQOSKADJPQZHB-RGYSVOEGSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(6r,9s,12r,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydr Chemical compound CCC(C)CCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)C([C@@H](C)O)NC(=O)[C@@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O YKQOSKADJPQZHB-RGYSVOEGSA-N 0.000 claims abstract description 12
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 9
229960004279 formaldehyde Drugs 0.000 claims abstract description 9
235000019256 formaldehyde Nutrition 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 9
239000004100 Oxytetracycline Substances 0.000 claims abstract description 8
229960000625 oxytetracycline Drugs 0.000 claims abstract description 8
235000019366 oxytetracycline Nutrition 0.000 claims abstract description 8
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 claims abstract description 8
239000003242 anti bacterial agent Substances 0.000 claims abstract description 6
239000000047 product Substances 0.000 claims abstract description 5
150000003522 tetracyclines Chemical class 0.000 claims abstract description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 3
239000011707 mineral Substances 0.000 claims abstract description 3
150000002891 organic anions Chemical class 0.000 claims abstract description 3
150000003140 primary amides Chemical group 0.000 claims abstract 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical group C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 claims description 6
OFVLGDICTFRJMM-WESIUVDSSA-N tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims 2
239000000126 substance Substances 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 4
229940079593 drug Drugs 0.000 abstract description 2
238000002483 medication Methods 0.000 abstract description 2
238000001228 spectrum Methods 0.000 abstract description 2
ZOBLCVKESRYZRS-UHFFFAOYSA-N Cl.Cl.Cl.S(=O)(=O)(O)O Chemical compound Cl.Cl.Cl.S(=O)(=O)(O)O ZOBLCVKESRYZRS-UHFFFAOYSA-N 0.000 abstract 1
239000013067 intermediate product Substances 0.000 abstract 1
238000002955 isolation Methods 0.000 abstract 1
241000699670 Mus sp. Species 0.000 description 4
230000004888 barrier function Effects 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
238000007918 intramuscular administration Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
241000894006 Bacteria Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
238000013019 agitation Methods 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
230000002485 urinary effect Effects 0.000 description 2
XIYOPDCBBDCGOE-IWVLMIASSA-N (4s,4ar,5s,5ar,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C=C1C2=CC=CC(O)=C2C(O)=C2[C@@H]1[C@H](O)[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O XIYOPDCBBDCGOE-IWVLMIASSA-N 0.000 description 1
SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 description 1
FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 description 1
PPJYSSNKSXAVDB-UHFFFAOYSA-N 3,3',5,5'-tetraiodothyroacetic acid Chemical compound IC1=CC(CC(=O)O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 PPJYSSNKSXAVDB-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000581364 Clinitrachus argentatus Species 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
241000792859 Enema Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
241000700605 Viruses Species 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000001408 amides Chemical group 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000003515 anti-microbian Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
229960003722 doxycycline Drugs 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940042016 methacycline Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229960004023 minocycline Drugs 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
229960005009 rolitetracycline Drugs 0.000 description 1
HMEYVGGHISAPJR-IAHYZSEUSA-N rolitetracycline Chemical compound O=C([C@@]1(O)C(O)=C2[C@@H]([C@](C3=CC=CC(O)=C3C2=O)(C)O)C[C@H]1[C@@H](C=1O)N(C)C)C=1C(=O)NCN1CCCC1 HMEYVGGHISAPJR-IAHYZSEUSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)

CA222,417A 1974-03-20 1975-03-18 La polymyxinemethyltetracycline Expired CA1070675A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7409510A FR2264558A1 (en)	1974-03-20	1974-03-20	Polymixin-methyl tetracycline salt antibiotics - active against Gram positive and negative bacteria, viruses and protozoa

Publications (1)

Publication Number	Publication Date
CA1070675A true CA1070675A (fr)	1980-01-29

Family

ID=9136607

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA222,417A Expired CA1070675A (fr)	1974-03-20	1975-03-18	La polymyxinemethyltetracycline

Country Status (4)

Country	Link
JP (1)	JPS51125715A (fr)
CA (1)	CA1070675A (fr)
DE (1)	DE2511852A1 (fr)
FR (1)	FR2264558A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1994009806A1 (fr) *	1992-10-29	1994-05-11	Rainer Denecke	Preparation permettant d'assurer la therapie et notamment la prophylaxie de maladies du tractus digestif
DE4307352A1 (de) *	1992-10-29	1994-05-05	Denecke Rainer Dr Med Vet	Präparat zur Therapie und insbesondere Prophylaxe von Erkrankungen des Verdauungstraktes
JP4917210B2 (ja) *	2001-04-11	2012-04-18	ロンシール工業株式会社	見切り材
JP4917214B2 (ja) *	2001-05-14	2012-04-18	ロンシール工業株式会社	腰壁用巾木及びその施工方法

1974
- 1974-03-20 FR FR7409510A patent/FR2264558A1/fr active Granted
1975
- 1975-03-18 CA CA222,417A patent/CA1070675A/fr not_active Expired
- 1975-03-18 DE DE19752511852 patent/DE2511852A1/de active Pending
- 1975-03-19 JP JP50034211A patent/JPS51125715A/ja active Pending

Also Published As

Publication number	Publication date
FR2264558B1 (fr)	1979-07-13
JPS51125715A (en)	1976-11-02
DE2511852A1 (de)	1975-10-09
FR2264558A1 (en)	1975-10-17

Legal Events

Date	Code	Title	Description
1997-01-29	MKEX	Expiry

Publication	Publication Date	Title
CA2516471C (fr)	2013-04-09	Composes organiques ferriques, utilisations desdits composes et procedes de fabrication associes
IL234755A (en)	2017-03-30	Tetracycline derivatives for the treatment of bacterial, viral and parasitic infections
JP2016196483A (ja)	2016-11-24	５−アミノ−２，３−ジヒドロフタラジン−１，４−ジオンナトリウム塩の結晶形ｉまたはｉｉを含有する医薬製剤
JPH0334979A (ja)	1991-02-14	１０―デアザミノプテリンおよびその１０―アルキル誘導体の製造方法
HU197295B (en)	1989-03-28	Process for production of new derivatives of n-/2'-aminphenil/-benzamid and medical preparatives containing those as active substance
US4452800A (en)	1984-06-05	Salts of 3(n-butyl)-4-hydroxy-1-phenyl-1,8-naphthyridine-2(1H)-one and their use in treating chronic obstructive lung diseases
CA1070675A (fr)	1980-01-29	La polymyxinemethyltetracycline
IE52717B1 (en)	1988-02-03	Novel indanyl derivatives and their manufacture and use
CN102918051B (zh)	2015-09-09	N6-(甲基二茂铁)喹唑啉-2,4,6-三胺(h2)和其衍生物,以及用作抗菌剂、抗寄生虫剂、抗原虫和抗利什曼虫剂的药物前体
US2770617A (en)	1956-11-13	2, 5-bis-ethyleneimino-hydroquinone and process for preparing same
US4039519A (en)	1977-08-02	Broad spectrum antibiotics and method
WO2019170046A1 (fr)	2019-09-12	Composés glycopeptidiques ayant une activité de résistance à des bactéries résistantes aux médicaments, leur procédé de préparation et leur utilisation
US4127671A (en)	1978-11-28	P-acetamidophenyl diethylaminoacetate
US9475759B2 (en)	2016-10-25	Tigecycline crystalline hydrate and preparation method therefor and use thereof
CN107141255A (zh)	2017-09-08	恩诺沙星‑钙螯合物及其合成方法和应用
US3373197A (en)	1968-03-12	Substituted 6-epitetracyclines and 5a-epi-6-epitetracyclines
JPH03128380A (ja)	1991-05-31	Ｎ↑５，ｎ↑１↑０―メチレン―５，６，７，８―テトラヒドロ葉酸の塩およびその製造方法
JPS5899490A (ja)	1983-06-13	リン酸アミド誘導体およびその製造方法ならびにそれを含有する医薬
JPS60501561A (ja)	1985-09-19	アゾ−ビス−サリチル酸およびその塩、該酸および該塩の薬学的処方および使用、並びに該酸の製造
JPS5838299A (ja)	1983-03-05	アミノグリコシド誘導体、その製造法およびそれを含む医薬組成物
US3658989A (en)	1972-04-25	Antibacterial composition containing tetracycline sulfamate and derivatives thereof
CN111072755B (zh)	2023-09-05	力肽络合物、其药物组合物、其制备方法和应用
JPS62228078A (ja)	1987-10-06	マイトマイシン誘導体及び抗腫瘍剤
US3526629A (en)	1970-09-01	Beta-hydroxyethylpiperazinocarboxymethyl - 7 - dimethylamino - 6 - deoxy-6-demethyltetracycline
US2746972A (en)	1956-05-22	Thiophene-2-carboxaldehyde thiosemicarbazone and certain substitution derivatives