GB1499323A - 6-substituted chromones and chromanones - Google Patents
6-substituted chromones and chromanonesInfo
- Publication number
- GB1499323A GB1499323A GB12784/74A GB1278474A GB1499323A GB 1499323 A GB1499323 A GB 1499323A GB 12784/74 A GB12784/74 A GB 12784/74A GB 1278474 A GB1278474 A GB 1278474A GB 1499323 A GB1499323 A GB 1499323A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- hydrogen
- methyl
- propionate
- 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
- -1 6-substituted chromones Chemical class 0.000 title abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 16
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- ARQVRCKIVSELCG-UHFFFAOYSA-N methyl 2-(4-methoxyphenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=C(OC)C=C1 ARQVRCKIVSELCG-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 abstract 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 2
- 239000012346 acetyl chloride Substances 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- OTTYFDRFBJPGRW-ONEGZZNKSA-N (e)-pent-2-enoyl chloride Chemical compound CC\C=C\C(Cl)=O OTTYFDRFBJPGRW-ONEGZZNKSA-N 0.000 abstract 1
- DCGRLMABSSGAPH-UHFFFAOYSA-N 2-(3-acetyl-4-hydroxyphenyl)ethyl acetate Chemical compound CC(=O)OCCC1=CC=C(O)C(C(C)=O)=C1 DCGRLMABSSGAPH-UHFFFAOYSA-N 0.000 abstract 1
- VIPNDDUFWVYIPH-UHFFFAOYSA-N 2-(4-methoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(C(C)CO)C=C1 VIPNDDUFWVYIPH-UHFFFAOYSA-N 0.000 abstract 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 abstract 1
- IDXXXGKJJBRGBL-UHFFFAOYSA-N 2-ethoxy-1-[2-hydroxy-5-(2-hydroxyethyl)phenyl]ethanone Chemical compound CCOCC(=O)C1=CC(CCO)=CC=C1O IDXXXGKJJBRGBL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 229940125904 compound 1 Drugs 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- HLSADYVXHNXEJS-UHFFFAOYSA-N methyl 2-(3-acetyl-4-hydroxyphenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=C(O)C(C(C)=O)=C1 HLSADYVXHNXEJS-UHFFFAOYSA-N 0.000 abstract 1
- MCPJAILZXPQXGM-UHFFFAOYSA-N methyl 2-(4-hydroxy-3-pent-2-enoylphenyl)propanoate Chemical compound CCC=CC(=O)C1=CC(C(C)C(=O)OC)=CC=C1O MCPJAILZXPQXGM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229940090181 propyl acetate Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12784/74A GB1499323A (en) | 1974-03-22 | 1974-03-22 | 6-substituted chromones and chromanones |
| NO750819A NO750819L (en:Method) | 1974-03-22 | 1975-03-11 | |
| ZA00751546A ZA751546B (en) | 1974-03-22 | 1975-03-12 | Anti-inflammatory chromone and compounds |
| US05/557,897 US4057641A (en) | 1974-03-22 | 1975-03-12 | Method of treating inflammation with 2-(2,3-dihydro-2-isopropyl-4-oxo-4H-1-benzopyran-6-yl)propionic acid |
| BE154400A BE826765A (fr) | 1974-03-22 | 1975-03-17 | Composes polycycliques |
| DE19752511647 DE2511647A1 (de) | 1974-03-22 | 1975-03-17 | Neue benzopyranderivate |
| GB2714277A GB1499324A (en) | 1974-03-22 | 1975-03-18 | Phenyl-acetic acid and ethanol derivatives |
| AU79296/75A AU490932B2 (en) | 1975-03-19 | 4-oxo-ben zopyran derivatives | |
| JP50033072A JPS50154264A (en:Method) | 1974-03-22 | 1975-03-20 | |
| FI750841A FI750841A7 (en:Method) | 1974-03-22 | 1975-03-21 | |
| DK120475A DK120475A (en:Method) | 1974-03-22 | 1975-03-21 | |
| ES435855A ES435855A1 (es) | 1974-03-22 | 1975-03-21 | Un procedimiento para la obtencion de derivados de benzopi-rano. |
| SE7503291A SE7503291L (en:Method) | 1974-03-22 | 1975-03-21 | |
| IL46893A IL46893A (en) | 1974-03-22 | 1975-03-21 | Pharmaceutical compositions containing 4-oxo- benzopyran-6-etanol or 6-acetic acid derivatives, certain novel compounds of this type and their preparation |
| CH753678A CH608798A5 (en:Method) | 1974-03-22 | 1975-03-21 | |
| NL7503397A NL7503397A (nl) | 1974-03-22 | 1975-03-21 | Nieuwe benzopyranderivaten en werkwijze voor de bereiding daarvan. |
| FR7508851A FR2264528B1 (en:Method) | 1974-03-22 | 1975-03-21 | |
| IE648/75A IE42116B1 (en) | 1974-03-22 | 1975-03-24 | 6-substituted chromones and chromanones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12784/74A GB1499323A (en) | 1974-03-22 | 1974-03-22 | 6-substituted chromones and chromanones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1499323A true GB1499323A (en) | 1978-02-01 |
Family
ID=10011064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12784/74A Expired GB1499323A (en) | 1974-03-22 | 1974-03-22 | 6-substituted chromones and chromanones |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4057641A (en:Method) |
| JP (1) | JPS50154264A (en:Method) |
| BE (1) | BE826765A (en:Method) |
| CH (1) | CH608798A5 (en:Method) |
| DE (1) | DE2511647A1 (en:Method) |
| DK (1) | DK120475A (en:Method) |
| ES (1) | ES435855A1 (en:Method) |
| FI (1) | FI750841A7 (en:Method) |
| FR (1) | FR2264528B1 (en:Method) |
| GB (1) | GB1499323A (en:Method) |
| IE (1) | IE42116B1 (en:Method) |
| IL (1) | IL46893A (en:Method) |
| NL (1) | NL7503397A (en:Method) |
| NO (1) | NO750819L (en:Method) |
| SE (1) | SE7503291L (en:Method) |
| ZA (1) | ZA751546B (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0087858A1 (en) * | 1982-02-05 | 1983-09-07 | Nippon Zoki Pharmaceutical Co. Ltd. | New chromanone compounds and pharmaceutical compositions containing them |
| EP0228172A1 (en) * | 1985-12-24 | 1987-07-08 | Mallinckrodt, Inc. (a Delaware corporation) | Preparation of 6-substituted 4-chromanones |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2549745A1 (de) * | 1974-11-20 | 1976-05-26 | Lipha | Durch einen chromonylrest substituierte propionsaeuren sowie deren derivate und verwendungen |
| US4151179A (en) * | 1975-03-12 | 1979-04-24 | Fisons Limited | 2-(4H-1-Benzopyran-6-yl)propionic acids |
| JPH0753725B2 (ja) * | 1987-10-08 | 1995-06-07 | 富山化学工業株式会社 | ４ｈ―１―ベンゾピラン―４―オン誘導体およびその塩、それらの製造法並びにそれらを含有する抗炎症剤 |
| US6051586A (en) * | 1997-12-19 | 2000-04-18 | Bayer Corporation | Sulfonamide substituted chroman derivatives useful as beta 3 adrenoreceptor agonists |
| US6469031B1 (en) | 1998-12-18 | 2002-10-22 | Bayer Corporation | Carboxyl substituted chroman derivatives useful as beta 3 adrenoreceptor agonists |
| CA2389924A1 (en) | 2000-01-24 | 2001-07-26 | Jozef S. Mruk | Use of flavone 8-acetic acid in vascular and cardiovascular interventions and acute coronary syndromes |
| AR035605A1 (es) | 2000-12-11 | 2004-06-16 | Bayer Corp | Derivados de aminometil cromano di-sustituidos, un metodo para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la manufactura de medicamentos utiles como agonistas beta-3-adreno-receptores |
| AR035858A1 (es) | 2001-04-23 | 2004-07-21 | Bayer Corp | Derivados de cromano 2,6-sustituidos,composiciones farmaceuticas,uso de dichos derivados para la manufactura de medicamentos utiles como agonistas adrenorreceptores beta-3 |
| JP2016516004A (ja) * | 2013-02-22 | 2016-06-02 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | 抗糖尿病二環式化合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2897211A (en) * | 1955-11-02 | 1959-07-28 | Recordati Lab Farmacologico S | Hydroxychromone derivatives and method of preparing the same |
| FR95487E (fr) * | 1967-07-26 | 1971-01-15 | Rech S Ind Sori Soc D | Nouveaux dérives flavoniques. |
| BE757821A (fr) * | 1970-08-01 | 1971-04-01 | Recordati Chem Pharm | Procede de preparation de l'acide 3-propionyl-salicylique et dederives de cet acide |
| US3775435A (en) * | 1971-08-26 | 1973-11-27 | American Home Prod | 5,6,7,8-tetrahydro-2,5(and 4,5)-dioxo-1-benzopyrans |
| GB1403487A (en) * | 1972-07-21 | 1975-08-28 | Yoshitomi Pharmaceutical | Heterocyclic substituted alkanoic acids and derivatives |
| US3825574A (en) * | 1972-12-04 | 1974-07-23 | Warner Lambert Co | Process for preparing substituted chromone-3-carbonitriles,carboxamides and carboxylic acids |
| US3862143A (en) * | 1972-12-04 | 1975-01-21 | Warner Lambert Co | Substituted chromone-3-carbonitriles, carboxamides and carboxylic acids |
| US3912760A (en) * | 1973-04-18 | 1975-10-14 | Warner Lambert Co | Process for the production of chromone derivatives and intermediates produced thereby |
-
1974
- 1974-03-22 GB GB12784/74A patent/GB1499323A/en not_active Expired
-
1975
- 1975-03-11 NO NO750819A patent/NO750819L/no unknown
- 1975-03-12 US US05/557,897 patent/US4057641A/en not_active Expired - Lifetime
- 1975-03-12 ZA ZA00751546A patent/ZA751546B/xx unknown
- 1975-03-17 DE DE19752511647 patent/DE2511647A1/de not_active Ceased
- 1975-03-17 BE BE154400A patent/BE826765A/xx unknown
- 1975-03-20 JP JP50033072A patent/JPS50154264A/ja active Pending
- 1975-03-21 SE SE7503291A patent/SE7503291L/xx unknown
- 1975-03-21 FR FR7508851A patent/FR2264528B1/fr not_active Expired
- 1975-03-21 IL IL46893A patent/IL46893A/xx unknown
- 1975-03-21 ES ES435855A patent/ES435855A1/es not_active Expired
- 1975-03-21 NL NL7503397A patent/NL7503397A/xx not_active Application Discontinuation
- 1975-03-21 FI FI750841A patent/FI750841A7/fi not_active Application Discontinuation
- 1975-03-21 CH CH753678A patent/CH608798A5/xx not_active IP Right Cessation
- 1975-03-21 DK DK120475A patent/DK120475A/da not_active Application Discontinuation
- 1975-03-24 IE IE648/75A patent/IE42116B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0087858A1 (en) * | 1982-02-05 | 1983-09-07 | Nippon Zoki Pharmaceutical Co. Ltd. | New chromanone compounds and pharmaceutical compositions containing them |
| EP0228172A1 (en) * | 1985-12-24 | 1987-07-08 | Mallinckrodt, Inc. (a Delaware corporation) | Preparation of 6-substituted 4-chromanones |
Also Published As
| Publication number | Publication date |
|---|---|
| IE42116L (en) | 1975-09-22 |
| FR2264528A1 (en:Method) | 1975-10-17 |
| IL46893A0 (en) | 1975-05-22 |
| ES435855A1 (es) | 1976-11-16 |
| IE42116B1 (en) | 1980-06-04 |
| SE7503291L (en:Method) | 1975-09-23 |
| BE826765A (fr) | 1975-09-17 |
| CH608798A5 (en:Method) | 1979-01-31 |
| AU7929675A (en) | 1976-09-23 |
| IL46893A (en) | 1978-08-31 |
| NL7503397A (nl) | 1975-09-24 |
| ZA751546B (en) | 1976-05-26 |
| DK120475A (en:Method) | 1975-09-23 |
| US4057641A (en) | 1977-11-08 |
| FI750841A7 (en:Method) | 1975-09-23 |
| NO750819L (en:Method) | 1975-09-23 |
| JPS50154264A (en:Method) | 1975-12-12 |
| FR2264528B1 (en:Method) | 1978-11-10 |
| DE2511647A1 (de) | 1975-09-25 |
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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 |