GB1266456A - - Google Patents
Info
- Publication number
- GB1266456A GB1266456A GB1266456DA GB1266456A GB 1266456 A GB1266456 A GB 1266456A GB 1266456D A GB1266456D A GB 1266456DA GB 1266456 A GB1266456 A GB 1266456A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacted
- give
- methyl
- benzyl
- methoxy
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract 2
- MKTXHNYIOYYOFA-UHFFFAOYSA-N 2-(3-benzoyl-2-hydroxyphenyl)acetic acid Chemical compound C(C1=CC=CC=C1)(=O)C=1C(=C(C=CC1)CC(=O)O)O MKTXHNYIOYYOFA-UHFFFAOYSA-N 0.000 abstract 1
- PNYKSCBMMRTDJD-UHFFFAOYSA-N 2-(3-benzoyl-2-hydroxyphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O PNYKSCBMMRTDJD-UHFFFAOYSA-N 0.000 abstract 1
- MIJYFLXOJQTGHU-UHFFFAOYSA-N 2-(3-benzoyl-2-methoxyphenyl)acetonitrile Chemical compound COC1=C(CC#N)C=CC=C1C(=O)C1=CC=CC=C1 MIJYFLXOJQTGHU-UHFFFAOYSA-N 0.000 abstract 1
- AULBUIGZOUKLJI-UHFFFAOYSA-N 2-(3-benzoyl-2-methoxyphenyl)propanoic acid Chemical compound COC1=C(C(C)C(O)=O)C=CC=C1C(=O)C1=CC=CC=C1 AULBUIGZOUKLJI-UHFFFAOYSA-N 0.000 abstract 1
- RQZFJVSLWPEOLL-UHFFFAOYSA-N 2-(3-benzyl-2-methoxyphenyl)propanoic acid Chemical compound C(C1=CC=CC=C1)C=1C(=C(C=CC1)C(C(=O)O)C)OC RQZFJVSLWPEOLL-UHFFFAOYSA-N 0.000 abstract 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 abstract 1
- HFNQVEWQLNIWJY-UHFFFAOYSA-N 7-benzyl-3-methyl-1-benzofuran-2-carbonyl azide Chemical compound N(=[N+]=[N-])C(=O)C=1OC2=C(C1C)C=CC=C2CC2=CC=CC=C2 HFNQVEWQLNIWJY-UHFFFAOYSA-N 0.000 abstract 1
- PVTYKAAGFXRHIX-UHFFFAOYSA-N 7-benzyl-3-methyl-1-benzofuran-2-carbonyl chloride Chemical compound ClC(=O)C=1OC2=C(C1C)C=CC=C2CC2=CC=CC=C2 PVTYKAAGFXRHIX-UHFFFAOYSA-N 0.000 abstract 1
- DIDRYYXGQBRXDJ-UHFFFAOYSA-N 7-benzyl-3-methyl-1-benzofuran-2-carboxylic acid Chemical compound C(=O)(O)C=1OC2=C(C1C)C=CC=C2CC2=CC=CC=C2 DIDRYYXGQBRXDJ-UHFFFAOYSA-N 0.000 abstract 1
- XAIFBLLJNTXJRW-UHFFFAOYSA-N 7-benzyl-3-methyl-3H-1-benzofuran-2-one Chemical compound O=C1OC2=C(C1C)C=CC=C2CC2=CC=CC=C2 XAIFBLLJNTXJRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- WAXNWQKNFZDHOM-UHFFFAOYSA-N [3-(bromomethyl)-2-methoxyphenyl]-phenylmethanone Chemical compound COC1=C(CBr)C=CC=C1C(=O)C1=CC=CC=C1 WAXNWQKNFZDHOM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001907 coumarones Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- DVHVUEKFAHRWLI-UHFFFAOYSA-N ethyl 7-benzyl-3-methyl-1-benzofuran-2-carboxylate Chemical compound C(C)OC(=O)C=1OC2=C(C1C)C=CC=C2CC2=CC=CC=C2 DVHVUEKFAHRWLI-UHFFFAOYSA-N 0.000 abstract 1
- HIEJPQDHSPOEEE-UHFFFAOYSA-N ethyl N-(7-benzyl-3-methyl-1-benzofuran-2-yl)carbamate Chemical compound C(C)OC(=O)NC=1OC2=C(C1C)C=CC=C2CC2=CC=CC=C2 HIEJPQDHSPOEEE-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- -1 ethyl α-chloroacetylacetate Chemical compound 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6916092A FR2043472A1 (cg-RX-API-DMAC10.html) | 1969-05-19 | 1969-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1266456A true GB1266456A (cg-RX-API-DMAC10.html) | 1972-03-08 |
Family
ID=9034230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1266456D Expired GB1266456A (cg-RX-API-DMAC10.html) | 1969-05-19 | 1970-05-19 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3621037A (cg-RX-API-DMAC10.html) |
| AT (1) | AT292687B (cg-RX-API-DMAC10.html) |
| BE (1) | BE750606A (cg-RX-API-DMAC10.html) |
| BR (1) | BR7019035D0 (cg-RX-API-DMAC10.html) |
| CH (1) | CH500965A (cg-RX-API-DMAC10.html) |
| CS (1) | CS158272B2 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2024389C3 (cg-RX-API-DMAC10.html) |
| DK (1) | DK125394B (cg-RX-API-DMAC10.html) |
| ES (1) | ES379793A1 (cg-RX-API-DMAC10.html) |
| FI (1) | FI51811C (cg-RX-API-DMAC10.html) |
| FR (1) | FR2043472A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1266456A (cg-RX-API-DMAC10.html) |
| IE (1) | IE34405B1 (cg-RX-API-DMAC10.html) |
| IL (1) | IL34549A (cg-RX-API-DMAC10.html) |
| LU (1) | LU60932A1 (cg-RX-API-DMAC10.html) |
| NL (1) | NL162907C (cg-RX-API-DMAC10.html) |
| OA (1) | OA03408A (cg-RX-API-DMAC10.html) |
| SE (1) | SE366740B (cg-RX-API-DMAC10.html) |
| YU (1) | YU33261B (cg-RX-API-DMAC10.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1035947B (it) * | 1975-06-05 | 1979-10-20 | Acraf | Sintesi dell acido m. benzoil idratropico |
| IT1222448B (it) * | 1987-08-06 | 1990-09-05 | Balschim S P A | Procedimento per preparare il ketoprofen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL279433A (cg-RX-API-DMAC10.html) * | 1961-06-08 | |||
| FR1546478A (fr) * | 1967-01-27 | 1968-11-22 | Rhone Poulenc Sa | Nouveaux dérivés de l'acide benzoyl-3 phénylacétique et leur préparation |
-
1969
- 1969-05-19 FR FR6916092A patent/FR2043472A1/fr not_active Withdrawn
-
1970
- 1970-04-28 CS CS297270A patent/CS158272B2/cs unknown
- 1970-05-11 NL NL7006784.A patent/NL162907C/xx not_active IP Right Cessation
- 1970-05-12 OA OA53917A patent/OA03408A/xx unknown
- 1970-05-15 DK DK248170AA patent/DK125394B/da unknown
- 1970-05-15 CH CH731170A patent/CH500965A/fr not_active IP Right Cessation
- 1970-05-15 BR BR219035/70A patent/BR7019035D0/pt unknown
- 1970-05-15 SE SE06737/70A patent/SE366740B/xx unknown
- 1970-05-18 IE IE643/70A patent/IE34405B1/xx unknown
- 1970-05-18 US US38595A patent/US3621037A/en not_active Expired - Lifetime
- 1970-05-18 IL IL34549A patent/IL34549A/xx unknown
- 1970-05-18 YU YU1265/70A patent/YU33261B/xx unknown
- 1970-05-19 BE BE750606D patent/BE750606A/xx unknown
- 1970-05-19 AT AT447070A patent/AT292687B/de not_active IP Right Cessation
- 1970-05-19 FI FI701397A patent/FI51811C/fi active
- 1970-05-19 GB GB1266456D patent/GB1266456A/en not_active Expired
- 1970-05-19 ES ES379793A patent/ES379793A1/es not_active Expired
- 1970-05-19 DE DE2024389A patent/DE2024389C3/de not_active Expired
- 1970-05-25 LU LU60932D patent/LU60932A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| OA03408A (fr) | 1970-12-15 |
| LU60932A1 (cg-RX-API-DMAC10.html) | 1970-08-04 |
| NL162907B (nl) | 1980-02-15 |
| FR2043472A1 (cg-RX-API-DMAC10.html) | 1971-02-19 |
| DE2024389C3 (de) | 1979-04-05 |
| CH500965A (fr) | 1970-12-31 |
| BE750606A (fr) | 1970-11-19 |
| DE2024389B2 (de) | 1978-07-27 |
| AT292687B (de) | 1971-09-10 |
| DE2024389A1 (de) | 1970-11-26 |
| NL162907C (nl) | 1980-07-15 |
| YU33261B (en) | 1976-08-31 |
| FI51811B (cg-RX-API-DMAC10.html) | 1976-12-31 |
| IE34405B1 (en) | 1975-04-30 |
| ES379793A1 (es) | 1972-09-16 |
| SE366740B (cg-RX-API-DMAC10.html) | 1974-05-06 |
| BR7019035D0 (pt) | 1973-04-26 |
| DK125394B (da) | 1973-02-12 |
| IL34549A0 (en) | 1970-07-19 |
| CS158272B2 (cg-RX-API-DMAC10.html) | 1974-10-15 |
| US3621037A (en) | 1971-11-16 |
| IE34405L (en) | 1970-11-19 |
| NL7006784A (cg-RX-API-DMAC10.html) | 1970-11-23 |
| YU126570A (en) | 1976-03-31 |
| FI51811C (fi) | 1977-04-12 |
| IL34549A (en) | 1973-03-30 |
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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 |