ES367837A1 - 2 3-dihydro-5-acylbenzofuran-2-carboxylic acids - Google Patents

2 3-dihydro-5-acylbenzofuran-2-carboxylic acids

Info

Publication number
ES367837A1
ES367837A1 ES367837A ES367837A ES367837A1 ES 367837 A1 ES367837 A1 ES 367837A1 ES 367837 A ES367837 A ES 367837A ES 367837 A ES367837 A ES 367837A ES 367837 A1 ES367837 A1 ES 367837A1
Authority
ES
Spain
Prior art keywords
prepared
carboxylic acid
chloro
benzofuran
dihydro
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
ES367837A
Other languages
Spanish (es)
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
JR 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 JR Geigy AG filed Critical JR Geigy AG
Publication of ES367837A1 publication Critical patent/ES367837A1/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • 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
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
    • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

Novel compounds I: in which R is C 2-7 alkyl, X is O or S, Y 1 is H, CH 3 or CH 3 O, Y 2 is H or CH 3 and Z 1 and Z 2 are H, F, Cl, Br, CH 3 , C 2 H 5 , CH 3 0, or C 2 H 5 O and their salts with bases are prepared by reaction of a compound II: with a halide R-CO-Q, Q being halo, or an anhydride (R-CO) 2 O, followed where desired by salt formation. Intermediates isolated are the compounds II prepared by reduction of the corresponding 2,3- double-bonded compound with sodium amalgam 6 - chloro - 2 - (2,3 - epoxypropyl) - phenol, prepared from 2-allyl-6-chlorophenol and peracetic acid 2,3 - dihydro - 2 - hydroxymethyl- 7-chlorobenzofuran, prepared by heating the above epoxy compound 2,3-dihydro-7-chlorobenzofuran-2-carboxylic acid prepared by oxidation of the 2-hydroxymethyl compound a mixture of 4- and 6-chloro-2,3-dihydro-2-hydroxymethyl-benzofuran, prepared similarly to the above hydroxymethyl derivative 2,3- dihydro - 6 - chloro - benzofuran - 2 - carboxylic acid, prepared by oxidation of the 2-hydroxymethyl compound (X) 7, 8-dimethyl-coumarin, prepared from 2,3-dimethylphenol and malic acid (Y) 6,7-dimethyl-benzofuran-2.carboxylic acid, prepared by reaction of the coumarin derivative with Br 2 and alcoholic potassium hydroxide 7 - ethyl coumarin 6 - ethyl - benzofuran - 2 - carboxylic acid 7 - chloro - 8 - methylcoumarin and 6 - chloro - 7 - methyl - benzofuran- 2-carboxylic acid, the latter four compounds being prepared similarly to (X) and (Y) above 6 - fluoro - benzofuran - 2 - carboxylic acid, prepared by reacting p -fluoro -salicylaldehyde with bromomalonic acid diethyl ester, followed by hydrolysis (P) 2-thioxo-5-(2,4-dichlorobenzyl. idene)-4-thiazolidinone, prepared from rhodanine and 2,4-diohlorobenzaldehyde 2,4-dichloro-[alpha]-mercapto-cinnamic acid, prepared from the above thiazolidinone by reaction with cone. HCl (Q) 6-chloro-benzo[b]thiophene-2- carboxylic acid, prepared from the above cinnamic acid by cyclization 2-thioxo.5.(2,6 dichlorobenzylidene)-4.thiazolidinone 2,3 - dihydro - 4 - chloro - benzo[b]thiophene - 2 - carboxylic acid, the latter two being prepared similarly to (P) and (Q) above 6-ethoxy-benzo[b]thiophene, prepared by reduction of the corresponding 3-one with NaBH 4 and 6-ethoxy-benzo[b] thiophene-2-carboxylic acid, prepared from the last-named intermediate by reaction with butyl lithium and solid CO 2 . Pharmaceutical compositions comprise a compound I together with a suitable carrier, are administered orally, rectally or parenterally, and have saluretic, antitussive and diuretic activity.
ES367837A 1968-05-30 1969-05-29 2 3-dihydro-5-acylbenzofuran-2-carboxylic acids Expired ES367837A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH803068A CH508615A (en) 1968-05-30 1968-05-30 Process for the preparation of new heterocyclic carboxylic acids

Publications (1)

Publication Number Publication Date
ES367837A1 true ES367837A1 (en) 1971-12-01

Family

ID=4334080

Family Applications (1)

Application Number Title Priority Date Filing Date
ES367837A Expired ES367837A1 (en) 1968-05-30 1969-05-29 2 3-dihydro-5-acylbenzofuran-2-carboxylic acids

Country Status (14)

Country Link
US (2) US3651094A (en)
AT (1) AT284835B (en)
BE (1) BE733768A (en)
CH (1) CH508615A (en)
DE (1) DE1927393A1 (en)
DK (1) DK124129B (en)
ES (1) ES367837A1 (en)
FR (1) FR2009652A1 (en)
GB (1) GB1265882A (en)
IE (1) IE33124B1 (en)
IL (1) IL32310A (en)
NL (1) NL6907966A (en)
NO (1) NO122753B (en)
SE (1) SE360359B (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3954748A (en) * 1968-07-29 1976-05-04 Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France 3-Alkoxy-thianapthene-2-carboxamides
US3969529A (en) * 1969-10-10 1976-07-13 C.E.R.P.H.A. Phenoxyacetic acid derivatives as diuretic agents
USB353986I5 (en) * 1969-10-10 1975-01-28
US4087542A (en) * 1975-07-09 1978-05-02 Merck & Co., Inc. 2,3-Dihydro-6,7-disubstituted-5-acyl benzofuran-2-carboxylic acids
US4181727A (en) * 1975-07-09 1980-01-01 Merck & Co., Inc. 2,3-Dihydro-6,7-disubstituted-5-acyl benzofuran-2-carboxylic acids
US4296122A (en) * 1975-07-09 1981-10-20 Merck & Co., Inc. 2,3-Dihydro-6,7-disubstituted-5-(acyl)benzofuran-2-carboxylic acids
US4401669A (en) * 1978-01-27 1983-08-30 Merck & Co., Inc. 2,3-Dihydro-substituted-5-benzoyl benzofuran-2-carboxylic acids and their use in treating hypertension
US4213999A (en) * 1979-06-07 1980-07-22 Shell Oil Company Inhibition of lipogenesis
US4213998A (en) * 1979-06-07 1980-07-22 Shell Oil Company Inhibition of lipogenesis
US4237144A (en) * 1979-06-21 1980-12-02 Merck & Co., Inc. 2,3-Dihydro-2,6,7-trisubstituted-5-acylbenzofurans
US4552891A (en) * 1983-09-13 1985-11-12 Eli Lilly And Company Benzothiophene derivatives
US4822803A (en) * 1983-10-31 1989-04-18 Merck Frosst Canada, Inc. Benzofuran 2-carboxylic acid hydrazides useful as inhibitors of leukotriene biosynthesis
US4933351A (en) * 1983-10-31 1990-06-12 Merck Frosst Canada, Inc. Benzofuran 2-carbox amides useful as inhibitors of leukoriene biosynthesis
US4654365A (en) * 1985-09-26 1987-03-31 Merck & Co., Inc. 2,3-dihydro-5-(3-oxo-2-cyclohexen-1-yl)-2-benzofurancarboxylic acids, and their salts useful in the treatment of brain injury
US5863936A (en) * 1995-04-18 1999-01-26 Geron Corporation Telomerase inhibitors
US5760062A (en) * 1995-04-18 1998-06-02 Geron Corporation Telomerase inhibitors
US5703116A (en) * 1995-04-18 1997-12-30 Geron Corporation Telomerase Inhibitors
US5770613A (en) * 1995-09-29 1998-06-23 Geron Corporation Telomerase inhibitors
US5767278A (en) * 1995-10-06 1998-06-16 Geron Corporation Telomerase inhibitors
US20040071797A1 (en) * 2002-10-09 2004-04-15 Dennis Donald P. Method and formulation for suppressing mold

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3255241A (en) * 1961-01-19 1966-06-07 Merck & Co Inc (2-alkylidene acyl)phenoxy-and (2-alkylidene acyl)phenylmercaptocarboxylic acids

Also Published As

Publication number Publication date
AT284835B (en) 1970-09-25
US3751430A (en) 1973-08-07
FR2009652A1 (en) 1970-02-06
IE33124L (en) 1969-11-30
DE1927393A1 (en) 1969-12-04
BE733768A (en) 1969-12-01
IL32310A (en) 1972-12-29
NO122753B (en) 1971-08-09
GB1265882A (en) 1972-03-08
IL32310A0 (en) 1969-07-30
SE360359B (en) 1973-09-24
DK124129B (en) 1972-09-18
IE33124B1 (en) 1974-03-20
NL6907966A (en) 1969-12-02
CH508615A (en) 1971-06-15
US3651094A (en) 1972-03-21

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