IE33124L - Benzofuran and benzothiophene derivatives. - Google Patents
Benzofuran and benzothiophene derivatives.Info
- Publication number
- IE33124L IE33124L IE690731A IE73169A IE33124L IE 33124 L IE33124 L IE 33124L IE 690731 A IE690731 A IE 690731A IE 73169 A IE73169 A IE 73169A IE 33124 L IE33124 L IE 33124L
- Authority
- IE
- Ireland
- Prior art keywords
- prepared
- carboxylic acid
- benzofuran
- chloro
- compound
- Prior art date
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
1,265,882. Benzofuran and benzothiophan derivatives. J. R. GEIGY A.G. 29 May, 1969 [30 May, 1968], No. 27281/69. Heading C2C. 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-α-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.
[GB1265882A]
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 (2)
Publication Number | Publication Date |
---|---|
IE33124L true IE33124L (en) | 1969-11-30 |
IE33124B1 IE33124B1 (en) | 1974-03-20 |
Family
ID=4334080
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE731/69A IE33124B1 (en) | 1968-05-30 | 1969-05-29 | New heterocyclic carboxylic acids their derivatives and use |
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)
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 |
US4296122A (en) * | 1975-07-09 | 1981-10-20 | 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 |
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 |
US4213998A (en) * | 1979-06-07 | 1980-07-22 | Shell Oil Company | Inhibition of lipogenesis |
US4213999A (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 |
US4933351A (en) * | 1983-10-31 | 1990-06-12 | Merck Frosst Canada, Inc. | Benzofuran 2-carbox amides useful as inhibitors of leukoriene biosynthesis |
US4822803A (en) * | 1983-10-31 | 1989-04-18 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid hydrazides useful as inhibitors of leukotriene 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 |
US5703116A (en) * | 1995-04-18 | 1997-12-30 | Geron Corporation | Telomerase Inhibitors |
US5760062A (en) * | 1995-04-18 | 1998-06-02 | Geron Corporation | Telomerase inhibitors |
US5863936A (en) * | 1995-04-18 | 1999-01-26 | 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)
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 |
-
1968
- 1968-05-30 CH CH803068A patent/CH508615A/en not_active IP Right Cessation
-
1969
- 1969-05-23 NL NL6907966A patent/NL6907966A/xx unknown
- 1969-05-23 NO NO2125/69A patent/NO122753B/no unknown
- 1969-05-23 SE SE07336/69A patent/SE360359B/xx unknown
- 1969-05-23 DK DK283069AA patent/DK124129B/en unknown
- 1969-05-26 US US827941A patent/US3651094A/en not_active Expired - Lifetime
- 1969-05-29 FR FR6917584A patent/FR2009652A1/fr active Pending
- 1969-05-29 ES ES367837A patent/ES367837A1/en not_active Expired
- 1969-05-29 GB GB1265882D patent/GB1265882A/en not_active Expired
- 1969-05-29 IE IE731/69A patent/IE33124B1/en unknown
- 1969-05-29 IL IL32310A patent/IL32310A/en unknown
- 1969-05-29 AT AT511669A patent/AT284835B/en not_active IP Right Cessation
- 1969-05-29 BE BE733768D patent/BE733768A/xx unknown
- 1969-05-29 DE DE19691927393 patent/DE1927393A1/en active Pending
-
1971
- 1971-09-20 US US00182164A patent/US3751430A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
ES367837A1 (en) | 1971-12-01 |
DE1927393A1 (en) | 1969-12-04 |
SE360359B (en) | 1973-09-24 |
NO122753B (en) | 1971-08-09 |
IL32310A0 (en) | 1969-07-30 |
FR2009652A1 (en) | 1970-02-06 |
BE733768A (en) | 1969-12-01 |
CH508615A (en) | 1971-06-15 |
US3651094A (en) | 1972-03-21 |
GB1265882A (en) | 1972-03-08 |
IL32310A (en) | 1972-12-29 |
AT284835B (en) | 1970-09-25 |
DK124129B (en) | 1972-09-18 |
IE33124B1 (en) | 1974-03-20 |
NL6907966A (en) | 1969-12-02 |
US3751430A (en) | 1973-08-07 |
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