GB532822A - Improvements in and relating to the production of ª‡-coumarilyl and ª‡-thionaphthenoyl-acetic acid esters - Google Patents
Improvements in and relating to the production of ª‡-coumarilyl and ª‡-thionaphthenoyl-acetic acid estersInfo
- Publication number
- GB532822A GB532822A GB2326339A GB2326339A GB532822A GB 532822 A GB532822 A GB 532822A GB 2326339 A GB2326339 A GB 2326339A GB 2326339 A GB2326339 A GB 2326339A GB 532822 A GB532822 A GB 532822A
- Authority
- GB
- United Kingdom
- Prior art keywords
- coumarilyl
- acetate
- ethyl
- general formula
- thionaphthenoyl
- 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
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- -1 nitro, amino, hydroxy Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
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
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
532,822. Coumarilyl- and thionaphthenoylacetic esters. KENDALL, J. D., and COLLINS, R. B. Aug. 11, 1939, No. 23263. [Class 2 (iii)] Coumarilyl- and thionaphthenoylacetic esters of the general formula where X is O or S, R 1 ... R 4 are the same or different and are hydrogen atoms or substituent groups e.g. hydrocarbon or substituted hydrocarbon groups, halogen atoms, nitro, amino, hydroxy or alkoxy group, and R 5 is a hydrocarbon radicle, are made by condensing an aldehyde of the general formula with a γ-halogenoacetoacetic ester. The aldehydes are preferably reacted in the form of their sodium salts. Two adjacent groups R 1 ... R 4 may together constitute the residue of a cyclic nucleus, e.g. a benz- or a methylenedioxygroup, fused on to the benzene ring of the general formula. The preparation of the following compounds is described in examples: ethyl coumarilyl acetate, ethyl 4-bromo- and 4:6- dibromo-coumarilyl acetate, ethyl 3:4-benzconmarilyl acetate (from 2-hydroxy-l-naphthaldehyde), and ethyl thionaphthenoyl acetate. The products are used, either themselves, or after conversion into the corresponding amides and.pyrozolones, as colour-formers as described in Specification 532,804.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2326339A GB532822A (en) | 1939-08-11 | 1939-08-11 | Improvements in and relating to the production of ª‡-coumarilyl and ª‡-thionaphthenoyl-acetic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2326339A GB532822A (en) | 1939-08-11 | 1939-08-11 | Improvements in and relating to the production of ª‡-coumarilyl and ª‡-thionaphthenoyl-acetic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB532822A true GB532822A (en) | 1941-01-31 |
Family
ID=10192821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2326339A Expired GB532822A (en) | 1939-08-11 | 1939-08-11 | Improvements in and relating to the production of ª‡-coumarilyl and ª‡-thionaphthenoyl-acetic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB532822A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814348A (en) * | 1983-01-24 | 1989-03-21 | Roussel Uclaf | Therapeutic compositions containing derivatives of acrylic acid having an oxygen-containing heterocycle, therapeutic treatment therewith and new compounds |
| US10414747B2 (en) * | 2016-10-04 | 2019-09-17 | Merck Sharp & Dohme Corp. | Benzo[b]thiophene compounds as sting agonists |
| US10793557B2 (en) | 2018-04-03 | 2020-10-06 | Merck Sharp & Dohme Corp. | Sting agonist compounds |
| US11285131B2 (en) | 2017-08-04 | 2022-03-29 | Merck Sharp & Dohme Corp. | Benzo[b]thiophene STING agonists for cancer treatment |
| US11312772B2 (en) | 2017-08-04 | 2022-04-26 | Merck Sharp & Dohme Corp. | Combinations of PD-1 antagonists and benzo [b] thiophene STING agonists for cancer treatment |
| US11702430B2 (en) | 2018-04-03 | 2023-07-18 | Merck Sharp & Dohme Llc | Aza-benzothiophene compounds as STING agonists |
-
1939
- 1939-08-11 GB GB2326339A patent/GB532822A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814348A (en) * | 1983-01-24 | 1989-03-21 | Roussel Uclaf | Therapeutic compositions containing derivatives of acrylic acid having an oxygen-containing heterocycle, therapeutic treatment therewith and new compounds |
| US10414747B2 (en) * | 2016-10-04 | 2019-09-17 | Merck Sharp & Dohme Corp. | Benzo[b]thiophene compounds as sting agonists |
| US10703738B2 (en) | 2016-10-04 | 2020-07-07 | Merck Sharp & Dohme Corp. | Benzo[b]thiophene compounds as STING agonists |
| US10730849B2 (en) | 2016-10-04 | 2020-08-04 | Merck Sharp & Dohme Corp. | Benzo[b]thiophene compounds as STING agonists |
| US11285131B2 (en) | 2017-08-04 | 2022-03-29 | Merck Sharp & Dohme Corp. | Benzo[b]thiophene STING agonists for cancer treatment |
| US11312772B2 (en) | 2017-08-04 | 2022-04-26 | Merck Sharp & Dohme Corp. | Combinations of PD-1 antagonists and benzo [b] thiophene STING agonists for cancer treatment |
| US10793557B2 (en) | 2018-04-03 | 2020-10-06 | Merck Sharp & Dohme Corp. | Sting agonist compounds |
| US11702430B2 (en) | 2018-04-03 | 2023-07-18 | Merck Sharp & Dohme Llc | Aza-benzothiophene compounds as STING agonists |
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