GB1377715A - Polycyclic lactones and their preparation - Google Patents

Polycyclic lactones and their preparation

Info

Publication number
GB1377715A
GB1377715A GB1958972A GB1958972A GB1377715A GB 1377715 A GB1377715 A GB 1377715A GB 1958972 A GB1958972 A GB 1958972A GB 1958972 A GB1958972 A GB 1958972A GB 1377715 A GB1377715 A GB 1377715A
Authority
GB
United Kingdom
Prior art keywords
compound
bromo
compounds
group
chloroacetyl
Prior art date
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
GB1958972A
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.)
Astra Lakemedel AB
Original Assignee
Astra Lakemedel AB
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.)
Filing date
Publication date
Application filed by Astra Lakemedel AB filed Critical Astra Lakemedel AB
Publication of GB1377715A publication Critical patent/GB1377715A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D463/02—Preparation
    • C07D463/04—Preparation by forming the ring or condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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
    • C07D477/24—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 with hetero atoms or carbon atoms 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 6
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Abstract

1377715 Bicyclic lactones; organomercury compounds ASTRA LAKEMEDEL AB 27 April 1972 [27 April 1971] 19589/72 Headings C2C and C2J Compounds of the general Formula (I) wherein X is halogen, N 3 - or H 2 N-; A is -S-, -S-CH 2 -, -O-, -O-CH 2 -, -CH 2 -, -CH 2 CH 2 -, or -NH-; and R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP>, which are the same or different, are each hydrogen, C 1-6 alkyl, or an aryl group and CO-R<SP>4</SP> represents a -COOH group or an ester group capable of being converted to a -COOH group, are obtained by reacting a compound of the Formula (II) wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are as above; CO-R<SP>12</SP> is an ester capable of having R<SP>12</SP> replaced with a hydroxy group; and Y<SP>1</SP> and Y<SP>2</SP>, which are the same or different, are each a halogen atom, with a compound of the general Formula (III)a: PhHgY wherein Ph is phenyl and Y is a halogen atom to form a compound having the Formula (IV) and decomposing said compound (IV) to provide the compound having the Formula (V) and, if desired, converting the ester group CO-R<SP>12</SP> to a -COOH group and/or converting the group Y<SP>1</SP> to N 3 or H 2 N. Compounds of Formula I defined above are novel, with the proviso that when A is -S-, R<SP>1</SP> and R<SP>2</SP> are C 1-6 alkyl with R<SP>1</SP> and R<SP>2</SP> together containing 3-12 carbon atoms. The compounds (I) are useful intermediates and may be acylated to form compounds having antibacterial activity. The preparation of intermediates is described as follows: bromochloroacetic acid is converted with SOCl 2 to bromo, chloroacetyl chloride which is reacted with 3-L-methoxy-carbonylthiazolidine and triethylamine to yield N-(α,α- bromo, chloroacetyl) - 3 - L - methoxy - carbonylthiazolidine; the latter was reacted with phenylmercury chloride in tetrahydrofuran under N 2 in the presence of potassium t-butoxide to give N- (α - phenylmercurio - α,α - bromochloroacetyl)- 3 - L - methoxycarbonyl - thiazolidine. Bromo, chloroacetyl chloride was reacted with DL-4- carbomethoxy - 5,5 - dimethylthiazolidine to form N - (α,α - bromo, chloroacetyl) - 4 - DL- methoxycarbonyl - 5,5 - dimethyl - thiazolidine. (The 4D-compound was similarly obtained.) The 4DL-compound was reacted with phenylmercury chloride as above to form N-(α- phenylmercurio - α,α - bromo chloroacetyl) - 4- DL-carbomethoxy-5,5-dimethylthiazolidine.
GB1958972A 1971-04-27 1972-04-27 Polycyclic lactones and their preparation Expired GB1377715A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE540571 1971-04-27

Publications (1)

Publication Number Publication Date
GB1377715A true GB1377715A (en) 1974-12-18

Family

ID=20266400

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1958972A Expired GB1377715A (en) 1971-04-27 1972-04-27 Polycyclic lactones and their preparation

Country Status (2)

Country Link
DE (1) DE2219601A1 (en)
GB (1) GB1377715A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4065623A (en) 1975-01-02 1977-12-27 Bristol-Myers Company O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
US4065622A (en) 1975-07-23 1977-12-27 Bristol-Myers Company O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
US4066832A (en) 1975-04-11 1978-01-03 Bristol-Myers Company 0-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
EP0031509A1 (en) * 1979-12-20 1981-07-08 Hoechst Uk Limited Penem derivatives
EP1082325A1 (en) * 1998-05-28 2001-03-14 Merck & Co., Inc. Naphthosulfamylmethyl penem antibacterials

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2361885A1 (en) * 1975-09-03 1978-03-17 Smithkline Corp ANALOGUES OF PENICILLIN, THEIR INTERMEDIARIES AND METHODS FOR OBTAINING THEM

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4065623A (en) 1975-01-02 1977-12-27 Bristol-Myers Company O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
US4066831A (en) 1975-01-02 1978-01-03 Bristol-Myers Company O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
US4066832A (en) 1975-04-11 1978-01-03 Bristol-Myers Company 0-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
US4068075A (en) 1975-04-11 1978-01-10 Bristol-Myers Company O-2-isocephem-4-carboxylic acid derivatives as antibacterial agents
US4068080A (en) 1975-04-11 1978-01-10 Bristol-Myers Company O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
US4068078A (en) 1975-04-11 1978-01-10 Bristol-Myers Corporation O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
US4065622A (en) 1975-07-23 1977-12-27 Bristol-Myers Company O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
US4068066A (en) 1975-07-23 1978-01-10 Bristol-Myers Company O-2-isocephem-4-carboxylic acid derivatives as antibacterial agents
EP0031509A1 (en) * 1979-12-20 1981-07-08 Hoechst Uk Limited Penem derivatives
US4576939A (en) * 1979-12-20 1986-03-18 Hoechst Ag Penem derivatives
EP1082325A1 (en) * 1998-05-28 2001-03-14 Merck & Co., Inc. Naphthosulfamylmethyl penem antibacterials
EP1082325A4 (en) * 1998-05-28 2002-02-06 Merck & Co Inc Naphthosulfamylmethyl penem antibacterials

Also Published As

Publication number Publication date
DE2219601A1 (en) 1972-11-16

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees