GB1017615A - Creación de Inventos y Patentes con Inteligencia Artificial

GB1017615A – Penicillins
– Google Patents

GB1017615A – Penicillins
– Google Patents
Penicillins

Info

Publication number
GB1017615A

GB1017615A
GB1639763A
GB1639763A
GB1017615A
GB 1017615 A
GB1017615 A
GB 1017615A
GB 1639763 A
GB1639763 A
GB 1639763A
GB 1639763 A
GB1639763 A
GB 1639763A
GB 1017615 A
GB1017615 A
GB 1017615A
Authority
GB
United Kingdom
Prior art keywords
amino
prepared
acetic acid
reacting
pyridyl
Prior art date
1962-04-27
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
GB1639763A
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.)
1962-04-27
Filing date
1963-04-25
Publication date
1966-01-19

1963-04-25
Application filed by Bristol Myers Co
filed
Critical
Bristol Myers Co

1966-01-19
Publication of GB1017615A
publication
Critical
patent/GB1017615A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

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

C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2

C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6

C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical

C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical

C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms

C07D499/70—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with hetero rings as additional substituents on the carbon chain

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6

C07D499/76—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with hetero rings directly attached to the carboxamido radical

Abstract

Penicillanic acids of the general formula wherein R1 has the formula in which R5 is hydrogen, alkyl, alkanoyl, alkyl-sulphonyl, cycloalkyl, phenyl, chlorophenyl or phenethyl, and R2, R3 and R4 are selected from hydrogen, and halogen, nitro, alkyl, alkoxy, alkylthio, dialkylamino, alkanoylamino, alkanoyl, alkylsulphonyl, cycloalkyl, cycloalkoxy or substituted or unsubstituted aryl, aralkyl, aryloxy or aralkyloxy groups, and non-toxic salts thereof, are prepared by reacting 6-amino-penicillanic acid or a salt thereof with an acid having the general formula or functional equivalent thereof wherein X is -NH2, -N3, or -NHB, where B is a blocking group removable by hydrogenation, in a suitable solvent and, if X is not -NH2, hydrogenating in the presence of a catalyst to produce the desired penicillin. Typical examples of the penicillanic acids of the above formula are D,L-6 – [a – amino – (2 – thienyl)acetamido] -, 6 – [(-) – a amino – (4 – pyridyl) – acetamido] – and D,L-6 – [a – amino (3 – pyrrolyl) acetamido] – penicillanic acid. a -Azido (3-thienyl) acetyl chloride is prepared by reacting a -azido (3-thienyl) acetic acid with thionyl chloride. a – Amino – (4 – pyridyl) acetic acid hydrochloride is prepared by reacting HCl with a -amino – (4 – pyridyl) acetonitrile which is prepared by reacting 4-pyridylaldehyde, ammonium chloride and potassium cyanide. a -Amino (3-pyridyl) acetic acid hydrochloride may be made similarly from 3-pyridylaldehyde. a – (N – Carbobenzoxyamino) – (3 – pyridyl) – acetic acid is prepared by reacting a -amino-(3-pyridyl) acetic acid with carbobenzoxy chloride. a – (N – Carbobenzoxyamino) – (2 – pyrrolyl) – acetic acid is prepared by reacting carbobenzoxy chloride with D,L-a -amino-(2-pyrrolyl)-acetic acid, which is prepared by refluxing in aqueous NaOH 5-(2-pyrrolyl)-hydantoin monoisopropanolate which is prepared by reacting sodium cyanide, ammonium carbonate and pyrrole-2-aldehyde and recrystallizing the product from isopropanol. (-) – a – amino (2 – thienyl) acetic acid is obtained from the D,L-acid by forming the d-10-camphor sulphonic acid salt, suspending it in water, adjusting the pH to 6.3 with conc. NH4OH and cooling in an ice bath.

GB1639763A
1962-04-27
1963-04-25
Penicillins

Expired

GB1017615A
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

US19077662A

1962-04-27
1962-04-27

US19078162A

1962-04-27
1962-04-27

Publications (1)

Publication Number
Publication Date

GB1017615A
true

GB1017615A
(en)

1966-01-19

Family
ID=26886430
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB1639763A
Expired

GB1017615A
(en)

1962-04-27
1963-04-25
Penicillins

Country Status (5)

Country
Link

CH
(1)

CH436298A
(en)

CY
(1)

CY475A
(en)

ES
(1)

ES287498A1
(en)

GB
(1)

GB1017615A
(en)

MY
(1)

MY6900181A
(en)

1963

1963-04-25
GB
GB1639763A
patent/GB1017615A/en
not_active
Expired

1963-04-26
CH
CH524063A
patent/CH436298A/en
unknown

1963-04-27
ES
ES287498A
patent/ES287498A1/en
not_active
Expired

1969

1969-02-26
CY
CY47569A
patent/CY475A/en
unknown

1969-12-31
MY
MY6900181A
patent/MY6900181A/en
unknown

Also Published As

Publication number
Publication date

ES287498A1
(en)

1963-12-01

CH436298A
(en)

1967-05-31

MY6900181A
(en)

1969-12-31

CY475A
(en)

1969-02-26

Información de contacto