GB1292469A

GB1292469A – Antibacterial derivatives of coumermycin
– Google Patents

GB1292469A – Antibacterial derivatives of coumermycin
– Google Patents
Antibacterial derivatives of coumermycin

Info

Publication number
GB1292469A

GB1292469A
GB61268/69A
GB6126869A
GB1292469A
GB 1292469 A
GB1292469 A
GB 1292469A
GB 61268/69 A
GB61268/69 A
GB 61268/69A
GB 6126869 A
GB6126869 A
GB 6126869A
GB 1292469 A
GB1292469 A
GB 1292469A
Authority
GB
United Kingdom
Prior art keywords
compound
acid
formula
alkyl
amino
Prior art date
1968-12-16
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
GB61268/69A
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.)

Bristol Myers Co

Original Assignee
Bristol Myers Co
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.)
1968-12-16
Filing date
1969-12-16
Publication date
1972-10-11

1969-12-16
Application filed by Bristol Myers Co
filed
Critical
Bristol Myers Co

1972-10-11
Publication of GB1292469A
publication
Critical
patent/GB1292469A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS

C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals

C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms

C07H17/06—Benzopyran radicals

C07H17/065—Benzo[b]pyrans

C07H17/075—Benzo[b]pyran-2-ones

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds

C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation

C07C45/46—Friedel-Crafts reactions

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates

C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring

C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups

C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups

C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups

C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups

C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups

C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups

Abstract

1292469 Derivatives of coumermycin and intermediates therefor BRISTOL-MYERS CO 16 Dec 1969 [16 Dec 1968] 61268/69 Headings C2A and C2C Novel antibiotics having the Formula I and pharmaceutically acceptable cationic salts thereof, wherein R is H or CH3; R4 is OH; each of R5 and R6 is H, F, Cl, Br, I, CF 3 , CCl 3 , NH 2 , N0 2 , CN, OH, N-(C 1 -C 8 )alkylamino; N,N – di(C 1 -C 8 alkyl) – amino, carboxamido, N – (C 1 -C 8 ) – alkylcarboxamido, N,N – di- (C 1 -C 8 alkyl)-carboxamido, carboxy, carb- (C 1 -C 8 ) alkoxy or acetoxy ; and n is 0 to 8, are prepared by (a) subjecting a tetra-, tri- or ditetrahydrodropyranyl ether of coumermycin A 1 or A 2 , of Formula X wherein R is H or CH 3 and R2 and R3 are the same or different and are either H or to acylative cleavage with an acid halide of Formula XI or an acid anhydride of formula or mixed anhydride of formula wherein hal is Cl, Br or I; R14 is C 1 -C 8 alkanoyloxy; R5 and R6 are H, F, Cl, Br, I, CF 3 , CCl 3, NO 2 , CN, N,N-di(C 1 -C 8 alkyl)amino, N,N-di. (C 1 -C 8 alkyl)carboxamido or carb(C 1 -C 8 )- alkoxy; and n is 0-8, to give an intermediate compound of Formula III and (b) hydrolysing said intermediate by allowing it to stand in a polar solvent in the presence of an acid to produce a compound of Formula I, and if desired (c) when R5 or R6 is acetoxy or carb(C 1 -C 8 )alkoxy hydrolysing the compound obtained from (b) to produce the corresponding compound in which R5 or R6 is hydroxy or carboxy respectively; or when R5 or R6 is nitro reducing the compound obtained from (b) to produce the corresponding compound in which R5 or R6 is amino, and (d) if desired when R5 or R6 is carboxy aminating the compound to produce the corresponding compound in which R5 or R6 is N-substituted or unsubstituted carboxamido ; or when R5 or R6 is amino alkylating the compound to produce the corresponding compound in which R5 or R6 is N-C 1 to C 8 alkyl amino or N-di(C 1 to C 8 alkyl)amino. 4 – Hydroxy – 3 – phenylacetylbenzoic acid is prepared by reacting ethyl p-hydroxybenzoate with phenylacetyl chloride followed by hydrolysis; the said compound is then reduced to 4- hydroxy – 3 – # -phenylethylbenzoic acid with nascent hydrogen. This compound is acetylated with acetic anhydride in pyridine to 4-acetoxy- 3-#-phenylethylbenzoic acid and converted to the acid chloride with SOCl 2 . 2-Hydroxybiphenyl and acetic acid are heated with boron trifluoride, followed by treatment with ice-water to give 4-hydroxy-3- phenylacetophenone which is reacted with iodine in pyridine and acidified to give 4-hydroxy-3- phenylbenzoic acid. This is converted to 4- acetoxy-3-phenylbenzoic acid with acetic anhydride. Pharmaceutical compositions having antibiotic activity against Gram-positive and Gramnegative bacteria comprise an antibiotic of Formula (I) or a salt thereof together with a pharmaceutically acceptable carrier.

GB61268/69A
1968-12-16
1969-12-16
Antibacterial derivatives of coumermycin

Expired

GB1292469A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US78422468A

1968-12-16
1968-12-16

Publications (1)

Publication Number
Publication Date

GB1292469A
true

GB1292469A
(en)

1972-10-11

Family
ID=25131741
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB61268/69A
Expired

GB1292469A
(en)

1968-12-16
1969-12-16
Antibacterial derivatives of coumermycin

Country Status (3)

Country
Link

US
(1)

US3547902A
(en)

CH
(1)

CH542873A
(en)

GB
(1)

GB1292469A
(en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US5444161A
(en)

*

1989-08-16
1995-08-22
Microgenics Corporation
Substrates for β-galactosidase

Family Cites Families (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3428623A
(en)

*

1966-11-02
1969-02-18
Bristol Myers Co
Coumarin derivatives

US3454548A
(en)

*

1967-03-20
1969-07-08
Bristol Myers Co
Noviosyloxy coumarin containing compounds

1968

1968-12-16
US
US784224A
patent/US3547902A/en
not_active
Expired – Lifetime

1969

1969-12-16
CH
CH1868869A
patent/CH542873A/en
not_active
IP Right Cessation

1969-12-16
GB
GB61268/69A
patent/GB1292469A/en
not_active
Expired

Also Published As

Publication number
Publication date

US3547902A
(en)

1970-12-15

CH542873A
(en)

1973-10-15

Similar Documents

Publication
Publication Date
Title

GB1333222A
(en)

1973-10-10

Cephalosporin compounds

ES469425A1
(en)

1980-01-01

N-Alkyl-N-acyl derivatives of thienamycin

GB1348737A
(en)

1974-03-20

Cephalosporin derivatives

GB1292469A
(en)

1972-10-11

Antibacterial derivatives of coumermycin

GB1301243A
(en)

1972-12-29

GB1164555A
(en)

1969-09-17

New Tropine Derivatives

GB1460811A
(en)

1977-01-06

Bis-benzamido-benzoic acid derivatives

GB1411700A
(en)

1975-10-29

Penicillins and production thereof

GB1203538A
(en)

1970-08-26

Cubane derivatives

GB1347598A
(en)

1974-02-27

Lincomycin derivatives and the manufacture thereof

GB1467401A
(en)

1977-03-16

Kanamycin derivatives

GB1396748A
(en)

1975-06-04

4-4-biphenylyl – butyramides

GB1480082A
(en)

1977-07-20

Cephalosporin antibiotic

GB1325770A
(en)

1973-08-08

Pyrimidopyridazine derivatives

GB1388400A
(en)

1975-03-26

Derivatives of alpha-aminocephalosporins

IE36742B1
(en)

1977-02-16

Isoxazolo pyrimidine derivatives

GB1431024A
(en)

1976-04-07

Aminoglycoside antibiotic

GB1315633A
(en)

1973-05-02

Derivatives of l-hydroxyproline

GB1480374A
(en)

1977-07-20

Aminocyclitol-aminoglycoside antibiotics and process for their preparation

GB1388409A
(en)

1975-03-26

2-cephem-4-carboxylic acid esters

GB1334125A
(en)

1973-10-17

Aminopropionanilides and a process for the preparation thereof

GB1334079A
(en)

1973-10-17

7-alpha-2,6-dihalo-4-pyridylthio acetamido cephalosporanic acids and derivatives thereof

GB1441345A
(en)

1976-06-30

Azetidionone derivatives

GB1512574A
(en)

1978-06-01

N-substituted aminomethyl-methoxy penam and cephem compounds

GB1470289A
(en)

1977-04-14

Aminomethyl-arylmethylpenicillin derivatives

Legal Events

Date
Code
Title
Description

1973-02-21
PS
Patent sealed [section 19, patents act 1949]

1976-07-14
PLNP
Patent lapsed through nonpayment of renewal fees

Download PDF in English