IE33124B1 - New heterocyclic carboxylic acids their derivatives and use - Google Patents
New heterocyclic carboxylic acids their derivatives and useInfo
- Publication number
- IE33124B1 IE33124B1 IE731/69A IE73169A IE33124B1 IE 33124 B1 IE33124 B1 IE 33124B1 IE 731/69 A IE731/69 A IE 731/69A IE 73169 A IE73169 A IE 73169A IE 33124 B1 IE33124 B1 IE 33124B1
- Authority
- IE
- Ireland
- Prior art keywords
- prepared
- carboxylic acid
- benzofuran
- chloro
- compound
- Prior art date
Links
- -1 heterocyclic carboxylic acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 238000006243 chemical reaction Methods 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- WEVPVZMJEYAFKM-UHFFFAOYSA-N (6-chloro-2,3-dihydro-1-benzofuran-2-yl)methanol Chemical compound C1=C(Cl)C=C2OC(CO)CC2=C1 WEVPVZMJEYAFKM-UHFFFAOYSA-N 0.000 abstract 1
- HDILUVUJBIHXQV-UHFFFAOYSA-N (7-chloro-2,3-dihydro-1-benzofuran-2-yl)methanol Chemical compound C1=CC(Cl)=C2OC(CO)CC2=C1 HDILUVUJBIHXQV-UHFFFAOYSA-N 0.000 abstract 1
- DAXJNUBSBFUTRP-RTQNCGMRSA-N (8r,9s,10r,13s,14s)-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(CO)C2=C1 DAXJNUBSBFUTRP-RTQNCGMRSA-N 0.000 abstract 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 abstract 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- ITZMIRCWGDWDCI-UHFFFAOYSA-N 2-chloro-6-(oxiran-2-ylmethyl)phenol Chemical compound OC1=C(Cl)C=CC=C1CC1OC1 ITZMIRCWGDWDCI-UHFFFAOYSA-N 0.000 abstract 1
- UPEBXJHGPMUFKU-UHFFFAOYSA-N 2-chloro-6-prop-2-enylphenol Chemical compound OC1=C(Cl)C=CC=C1CC=C UPEBXJHGPMUFKU-UHFFFAOYSA-N 0.000 abstract 1
- LQWJCKLAJRCTRP-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-2-sulfanylprop-2-enoic acid Chemical compound ClC1=C(C=CC(=C1)Cl)C=C(C(=O)O)S LQWJCKLAJRCTRP-UHFFFAOYSA-N 0.000 abstract 1
- DEXIXUHOXHEGAO-UHFFFAOYSA-N 4-chloro-2,3-dihydro-1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C(Cl)C2=C1SC(C(=O)O)C2 DEXIXUHOXHEGAO-UHFFFAOYSA-N 0.000 abstract 1
- GBJJCODOZGPTBC-UHFFFAOYSA-N 4-fluoro-2-hydroxybenzaldehyde Chemical compound OC1=CC(F)=CC=C1C=O GBJJCODOZGPTBC-UHFFFAOYSA-N 0.000 abstract 1
- AVAGKGZNBMZOLD-UHFFFAOYSA-N 6-chloro-1-benzothiophene-2-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(C(=O)O)=CC2=C1 AVAGKGZNBMZOLD-UHFFFAOYSA-N 0.000 abstract 1
- ADCSXAUMFOOIRE-UHFFFAOYSA-N 6-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(Cl)C=C2OC(C(=O)O)CC2=C1 ADCSXAUMFOOIRE-UHFFFAOYSA-N 0.000 abstract 1
- AAOIETLWISYSNR-UHFFFAOYSA-N 6-chloro-7-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(Cl)C=CC2=C1OC(C(O)=O)=C2 AAOIETLWISYSNR-UHFFFAOYSA-N 0.000 abstract 1
- CTZIOFMIHKGJHZ-UHFFFAOYSA-N 6-ethoxy-1-benzothiophene Chemical compound CCOC1=CC=C2C=CSC2=C1 CTZIOFMIHKGJHZ-UHFFFAOYSA-N 0.000 abstract 1
- CYSOQVHPWPQGAD-UHFFFAOYSA-N 6-ethoxy-1-benzothiophene-2-carboxylic acid Chemical compound CCOC1=CC=C2C=C(C(O)=O)SC2=C1 CYSOQVHPWPQGAD-UHFFFAOYSA-N 0.000 abstract 1
- FECWAUVNWRDABN-UHFFFAOYSA-N 6-ethyl-1-benzofuran-2-carboxylic acid Chemical compound CCC1=CC=C2C=C(C(O)=O)OC2=C1 FECWAUVNWRDABN-UHFFFAOYSA-N 0.000 abstract 1
- GWBDBIRTRPIXJV-UHFFFAOYSA-N 6-fluoro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(F)C=C2OC(C(=O)O)=CC2=C1 GWBDBIRTRPIXJV-UHFFFAOYSA-N 0.000 abstract 1
- QXBQJXVMLMPNHS-UHFFFAOYSA-N 7,8-dimethylchromen-2-one Chemical compound C1=CC(=O)OC2=C(C)C(C)=CC=C21 QXBQJXVMLMPNHS-UHFFFAOYSA-N 0.000 abstract 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 abstract 1
- KSSRTMJGUNWSTN-UHFFFAOYSA-N 7-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=CC(Cl)=C2OC(C(=O)O)CC2=C1 KSSRTMJGUNWSTN-UHFFFAOYSA-N 0.000 abstract 1
- VHOAUUCXGIKDJV-UHFFFAOYSA-N 7-chloro-8-methylchromen-2-one Chemical compound ClC1=CC=C2C=CC(OC2=C1C)=O VHOAUUCXGIKDJV-UHFFFAOYSA-N 0.000 abstract 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000000954 anitussive effect Effects 0.000 abstract 1
- 229940124584 antitussives Drugs 0.000 abstract 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229930016911 cinnamic acid Natural products 0.000 abstract 1
- 235000013985 cinnamic acid Nutrition 0.000 abstract 1
- 235000001671 coumarin Nutrition 0.000 abstract 1
- 229960000956 coumarin Drugs 0.000 abstract 1
- FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 abstract 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000001630 malic acid Substances 0.000 abstract 1
- 235000011090 malic acid Nutrition 0.000 abstract 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 abstract 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 230000000894 saliuretic effect Effects 0.000 abstract 1
- 229910001023 sodium amalgam Inorganic materials 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH803068A CH508615A (de) | 1968-05-30 | 1968-05-30 | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33124L IE33124L (en) | 1969-11-30 |
| IE33124B1 true 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)
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 |
| USB353986I5 (enrdf_load_stackoverflow) * | 1969-10-10 | 1975-01-28 | ||
| US3969529A (en) * | 1969-10-10 | 1976-07-13 | C.E.R.P.H.A. | Phenoxyacetic acid derivatives as diuretic agents |
| 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 |
| 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 |
| US5760062A (en) * | 1995-04-18 | 1998-06-02 | Geron Corporation | Telomerase inhibitors |
| US5703116A (en) * | 1995-04-18 | 1997-12-30 | 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/de not_active IP Right Cessation
-
1969
- 1969-05-23 SE SE07336/69A patent/SE360359B/xx unknown
- 1969-05-23 NO NO2125/69A patent/NO122753B/no unknown
- 1969-05-23 DK DK283069AA patent/DK124129B/da unknown
- 1969-05-23 NL NL6907966A patent/NL6907966A/xx unknown
- 1969-05-26 US US827941A patent/US3651094A/en not_active Expired - Lifetime
- 1969-05-29 AT AT511669A patent/AT284835B/de not_active IP Right Cessation
- 1969-05-29 GB GB1265882D patent/GB1265882A/en not_active Expired
- 1969-05-29 ES ES367837A patent/ES367837A1/es not_active Expired
- 1969-05-29 BE BE733768D patent/BE733768A/xx unknown
- 1969-05-29 IL IL32310A patent/IL32310A/xx unknown
- 1969-05-29 DE DE19691927393 patent/DE1927393A1/de active Pending
- 1969-05-29 IE IE731/69A patent/IE33124B1/xx unknown
- 1969-05-29 FR FR6917584A patent/FR2009652A1/fr active Pending
-
1971
- 1971-09-20 US US00182164A patent/US3751430A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO122753B (enrdf_load_stackoverflow) | 1971-08-09 |
| CH508615A (de) | 1971-06-15 |
| SE360359B (enrdf_load_stackoverflow) | 1973-09-24 |
| NL6907966A (enrdf_load_stackoverflow) | 1969-12-02 |
| US3651094A (en) | 1972-03-21 |
| ES367837A1 (es) | 1971-12-01 |
| BE733768A (enrdf_load_stackoverflow) | 1969-12-01 |
| US3751430A (en) | 1973-08-07 |
| GB1265882A (enrdf_load_stackoverflow) | 1972-03-08 |
| DK124129B (da) | 1972-09-18 |
| DE1927393A1 (de) | 1969-12-04 |
| IE33124L (en) | 1969-11-30 |
| FR2009652A1 (enrdf_load_stackoverflow) | 1970-02-06 |
| IL32310A0 (en) | 1969-07-30 |
| AT284835B (de) | 1970-09-25 |
| IL32310A (en) | 1972-12-29 |
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