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GB1312470A - Benzofuran and benzothiophene carboxylic acids processes for their production and medicaments containing same - Google Patents

Benzofuran and benzothiophene carboxylic acids processes for their production and medicaments containing same

Info

Publication number
GB1312470A
GB1312470A GB5494670A GB5494670A GB1312470A GB 1312470 A GB1312470 A GB 1312470A GB 5494670 A GB5494670 A GB 5494670A GB 5494670 A GB5494670 A GB 5494670A GB 1312470 A GB1312470 A GB 1312470A
Authority
GB
United Kingdom
Prior art keywords
formula
reacting
compound
prepared
carboxylic acid
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
GB5494670A
Inventor
E Habicht
B Libis
J Zergenyi
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1312470A publication Critical patent/GB1312470A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/56—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
    • C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1312470 Benzofuran and benzothiophene derivatives CIBA GEIGY AG 19 Nov 1970 [20 Nov 1969] 54946/70 Heading C2C Novel compounds of Formula I (in which X is O or S, Y is H or CH 3 , Z 1 is CH 3 , CH 3 O, Cl or F, Z 2 is H or CH 3 and R is C 1-5 alkyl) and their salts with bases, are prepared by (a) reacting a compound of Formula II (in which Z 3 is an oxygen atom or an alkyl-, aryl- or aralkyl-imino group) with a nitroalkane of formula RCH 2 NO 2 , or (b) hydrolysing a corresponding ester of an acid of Formula I. The resulting acids and salts may be interconverted. Compounds of Formula II (in which Z 3 is an oxygen atom) are prepared by reacting a compound of Formula III with a dichloromethyl alkyl ether in the presence of a Friedel-Crafts catalyst in an inert solvent. Esters of acids of Formula I are prepared by reacting a compound of Formula II (in which Z 3 is an oxygen atom) with an alcohol, e.g. ethanol, to form the corresponding carboxylic acid ester, reacting this with an appropriate primary amine to give an ester of a compound of Formula II (in which Z 3 is an alkyl-, aryl- or aralkyl-imino group) and reacting this compound with a nitroalkane of formula RCH 2 NO 2 . 2,3 - Dihydro - 6,7 - dimethylfuran - 2 - carboxylic acid is prepared by reacting 2,3-dimethylphenol with malic acid to form 7,8-dimethylcoumarin, reacting this with bromine in chloroform to form 6,7-dimethylbenzofuran-2-carboxylic acid, and reducing this with sodium amalgam. 2,3 - Dihydro - 6 - chlorobenzothiophene - 2- carboxylic acid is prepared by reacting rhodanine with 2,4-dichlorobenzaldehyde to form 5-(2,4- dichlorobenzylidene)-rhodanine, hydrolysing this to form 2,4-dichloro-α-mercapto-cinnamic acid, cyclizing this by treatment with sodium methylate to form 6-chlorobenzothiophene-2-carboxylic acid and reducing this with sodium amalgam. Pharmaceutical compositions having diuretic and saluretic activity comprise a compound of Formula I, or a pharmaceutically acceptable salt thereof with a base, together with a pharmaceutical carrier. The compositions may be administered orally.
GB5494670A 1969-11-20 1970-11-19 Benzofuran and benzothiophene carboxylic acids processes for their production and medicaments containing same Expired GB1312470A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1727369A CH523236A (en) 1969-11-20 1969-11-20 Process for the preparation of new heterocyclic carboxylic acids

Publications (1)

Publication Number Publication Date
GB1312470A true GB1312470A (en) 1973-04-04

Family

ID=4424112

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5494670A Expired GB1312470A (en) 1969-11-20 1970-11-19 Benzofuran and benzothiophene carboxylic acids processes for their production and medicaments containing same

Country Status (15)

Country Link
AT (2) AT299937B (en)
BE (1) BE759138A (en)
BG (1) BG18182A3 (en)
CA (1) CA963016A (en)
CH (2) CH523237A (en)
DE (1) DE2056935A1 (en)
DK (1) DK126038B (en)
ES (2) ES385701A1 (en)
FR (1) FR2073396B1 (en)
GB (1) GB1312470A (en)
IL (1) IL35693A (en)
NL (1) NL7016683A (en)
SE (1) SE375531B (en)
SU (1) SU366609A3 (en)
ZA (1) ZA707819B (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH510008A (en) * 1968-05-30 1971-07-15 Ciba Geigy Ag Benzofuranyl-and benzothienyl-carboxylic acids

Also Published As

Publication number Publication date
ES385701A1 (en) 1973-10-01
BE759138A (en) 1971-05-19
IL35693A0 (en) 1971-01-28
CH523237A (en) 1972-05-31
ES385702A1 (en) 1973-04-01
DE2056935A1 (en) 1971-05-27
NL7016683A (en) 1971-05-24
BG18182A3 (en) 1974-09-02
CA963016A (en) 1975-02-18
DK126038B (en) 1973-06-04
AT299937B (en) 1972-07-10
AT305275B (en) 1973-02-26
SE375531B (en) 1975-04-21
FR2073396B1 (en) 1974-02-22
CH523236A (en) 1972-05-31
FR2073396A1 (en) 1971-10-01
ZA707819B (en) 1971-08-25
SU366609A3 (en) 1973-01-16
IL35693A (en) 1973-06-29

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee