GB1464242A - Benzoyl benzofurans and compositions comprising them - Google Patents
Benzoyl benzofurans and compositions comprising themInfo
- Publication number
- GB1464242A GB1464242A GB1041475A GB1041475A GB1464242A GB 1464242 A GB1464242 A GB 1464242A GB 1041475 A GB1041475 A GB 1041475A GB 1041475 A GB1041475 A GB 1041475A GB 1464242 A GB1464242 A GB 1464242A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- hydrogen
- alkoxyphenyl
- tri
- alkylphenyl
- 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
- DZRJNLPOTUVETG-UHFFFAOYSA-N 1-benzofuran-2-yl(phenyl)methanone Chemical class C=1C2=CC=CC=C2OC=1C(=O)C1=CC=CC=C1 DZRJNLPOTUVETG-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 4
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001907 coumarones Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 230000000304 vasodilatating effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy 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
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- 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
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1464242 Benzofurans SMITHKLINE CORP 13 March 1975 [18 April 1974 17 Oct 1974] 10414/75 Heading C2C Novel compounds of Formula I or a pharmaceutically acceptable acid addition salt thereof, in which: R 1 is phenyl, halophenyl, dihalophenyl, trihalophenyl, lower alkylphenyl, di-lower alkylphenyl, tri-lower alkylphenyl, lower alkoxyphenyl, di-lower alkoxyphenyl, tri-lower alkoxyphenyl, lower alkyl-di-lower alkoxyphenyl or lower alkoxy-di-lower alkylphenyl; R 2 is hydrogen, halo, lower alkyl, lower alkoxy, nitro or trifluoromethyl; R 3 is a group of Formula A R 4 is hydrogen, methyl, ethyl or propyl and R 5 is methyl, ethyl or propyl or R 4 and R 5 together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine, N-(lower alkyl)piperazine, morpholine or perhydroazepine ring; R 6 is hydrogen or hydroxy; m is 0 or 1 when R 6 is hydrogen and 1 when R 6 is hydroxy; n is 0 or 1; and Z is oxygen or sulphur are prepared by one of the following reaction schemes wherein R 1 , R 2 , R 4 , R 5 and n have the above significance and p is 2 or 3, X and Y are halogen, R 1 <SP>1</SP> is phenyl, mono-, di- or trihalo-phenyl or mono-, di- or tri-alkyl-phenyl. The benzothiophenes are similarly prepared by schemes analogous to reaction schemes 1 and 2 above. Pharmaceutical compositions in conventional forms for oral or parenteral administration and having vaso-dilatory activity comprise an above novel compound and a carrier or diluent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46200874A | 1974-04-18 | 1974-04-18 | |
| US51580874A | 1974-10-17 | 1974-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1464242A true GB1464242A (en) | 1977-02-09 |
Family
ID=27040202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1041475A Expired GB1464242A (en) | 1974-04-18 | 1975-03-13 | Benzoyl benzofurans and compositions comprising them |
Country Status (7)
| Country | Link |
|---|---|
| CA (1) | CA1053673A (en) |
| DE (1) | DE2517296A1 (en) |
| FR (1) | FR2267770B1 (en) |
| GB (1) | GB1464242A (en) |
| IE (1) | IE42353B1 (en) |
| IL (1) | IL46980A (en) |
| NL (1) | NL7504647A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663347A (en) * | 1983-10-31 | 1987-05-05 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene biosynthesis |
| US4822803A (en) * | 1983-10-31 | 1989-04-18 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid hydrazides useful as inhibitors of leukotriene biosynthesis |
| US4933351A (en) * | 1983-10-31 | 1990-06-12 | Merck Frosst Canada, Inc. | Benzofuran 2-carbox amides useful as inhibitors of leukoriene biosynthesis |
| WO2003000671A1 (en) * | 2001-06-20 | 2003-01-03 | Wyeth | Naphthyl benzofuran derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112015022787A2 (en) | 2013-03-15 | 2017-11-07 | Epizyme Inc | compounds, pharmaceutical compositions, kit or packaged pharmaceutical article, and method of treating a carm1-mediated disorder |
-
1975
- 1975-03-13 GB GB1041475A patent/GB1464242A/en not_active Expired
- 1975-03-25 CA CA223,045A patent/CA1053673A/en not_active Expired
- 1975-03-31 IL IL46980A patent/IL46980A/en unknown
- 1975-04-16 FR FR7511781A patent/FR2267770B1/fr not_active Expired
- 1975-04-18 NL NL7504647A patent/NL7504647A/en not_active Application Discontinuation
- 1975-04-18 IE IE886/75A patent/IE42353B1/en unknown
- 1975-04-18 DE DE19752517296 patent/DE2517296A1/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663347A (en) * | 1983-10-31 | 1987-05-05 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene biosynthesis |
| US4822803A (en) * | 1983-10-31 | 1989-04-18 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid hydrazides useful as inhibitors of leukotriene biosynthesis |
| US4933351A (en) * | 1983-10-31 | 1990-06-12 | Merck Frosst Canada, Inc. | Benzofuran 2-carbox amides useful as inhibitors of leukoriene biosynthesis |
| WO2003000671A1 (en) * | 2001-06-20 | 2003-01-03 | Wyeth | Naphthyl benzofuran derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| US6599925B2 (en) | 2001-06-20 | 2003-07-29 | Wyeth | Substituted naphthyl benzofuran derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2517296A1 (en) | 1975-11-06 |
| IL46980A0 (en) | 1975-05-22 |
| AU7985075A (en) | 1976-10-07 |
| IE42353L (en) | 1975-10-18 |
| CA1053673A (en) | 1979-05-01 |
| IE42353B1 (en) | 1980-07-30 |
| FR2267770B1 (en) | 1979-08-10 |
| IL46980A (en) | 1978-10-31 |
| FR2267770A1 (en) | 1975-11-14 |
| NL7504647A (en) | 1975-10-21 |
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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 |