CA1086757A - 2,3-dihydrobenzofuran-2-one derivatives - Google Patents
2,3-dihydrobenzofuran-2-one derivativesInfo
- Publication number
- CA1086757A CA1086757A CA247,552A CA247552A CA1086757A CA 1086757 A CA1086757 A CA 1086757A CA 247552 A CA247552 A CA 247552A CA 1086757 A CA1086757 A CA 1086757A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- carbon atoms
- formula
- lower alkyl
- compounds
- 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
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- -1 methyl-thio, hydroxy Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 8
- FFPGKSCPXZYKFO-UHFFFAOYSA-N 5-chloro-6-cyclohexyl-3h-1-benzofuran-2-one Chemical compound ClC1=CC=2CC(=O)OC=2C=C1C1CCCCC1 FFPGKSCPXZYKFO-UHFFFAOYSA-N 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 4
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002241 furanones Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
- C07D307/83—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3129/75 | 1975-03-12 | ||
| CH312975A CH614707A5 (en) | 1975-03-12 | 1975-03-12 | Process for the preparation of novel dihydrobenzofuranone derivatives |
| CH9678/75 | 1975-07-24 | ||
| CH967875 | 1975-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1086757A true CA1086757A (en) | 1980-09-30 |
Family
ID=25692258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA247,552A Expired CA1086757A (en) | 1975-03-12 | 1976-03-10 | 2,3-dihydrobenzofuran-2-one derivatives |
Country Status (19)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514415A (en) * | 1981-10-28 | 1985-04-30 | Ciba Geigy Corporation | Benzofuran-2(3H)-ones used as anti-inflammatory agents |
| US4849428A (en) * | 1987-11-23 | 1989-07-18 | The Procter & Gamble Company | Cyclic anti-inflammatory derivatives of di-tert-butylphenol compounds, compositions and use |
-
1976
- 1976-03-03 DK DK92176AA patent/DK137274B/da not_active Application Discontinuation
- 1976-03-03 FI FI760548A patent/FI760548A7/fi not_active Application Discontinuation
- 1976-03-03 DE DE19762608697 patent/DE2608697A1/de not_active Withdrawn
- 1976-03-04 NO NO760745A patent/NO760745L/no unknown
- 1976-03-05 SE SE7603053A patent/SE7603053L/xx unknown
- 1976-03-08 NL NL7602393A patent/NL7602393A/xx not_active Application Discontinuation
- 1976-03-09 GB GB9315/76A patent/GB1546701A/en not_active Expired
- 1976-03-10 IE IE501/76A patent/IE43704B1/en unknown
- 1976-03-10 IL IL49192A patent/IL49192A/xx unknown
- 1976-03-10 AT AT173876A patent/AT357516B/de not_active IP Right Cessation
- 1976-03-10 CA CA247,552A patent/CA1086757A/en not_active Expired
- 1976-03-10 PT PT64886A patent/PT64886B/pt unknown
- 1976-03-10 NZ NZ180273A patent/NZ180273A/xx unknown
- 1976-03-10 ES ES445922A patent/ES445922A1/es not_active Expired
- 1976-03-10 FR FR7606829A patent/FR2303540A1/fr active Granted
- 1976-03-10 DD DD191782A patent/DD125210A5/xx unknown
- 1976-03-11 YU YU00635/76A patent/YU63576A/xx unknown
- 1976-03-11 JP JP51025655A patent/JPS51113864A/ja active Pending
- 1976-03-12 AU AU11970/76A patent/AU508681B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU508681B2 (en) | 1980-03-27 |
| NL7602393A (nl) | 1976-09-14 |
| DK92176A (enrdf_load_html_response) | 1976-09-13 |
| ES445922A1 (es) | 1977-08-16 |
| IL49192A (en) | 1981-01-30 |
| PT64886B (fr) | 1977-11-17 |
| IL49192A0 (en) | 1976-05-31 |
| YU63576A (en) | 1982-05-31 |
| DD125210A5 (enrdf_load_html_response) | 1977-04-06 |
| NZ180273A (en) | 1978-03-06 |
| NO760745L (enrdf_load_html_response) | 1976-09-14 |
| DK137274B (da) | 1978-02-13 |
| AT357516B (de) | 1980-07-10 |
| FR2303540A1 (fr) | 1976-10-08 |
| ATA173876A (de) | 1979-12-15 |
| DE2608697A1 (de) | 1976-09-23 |
| FI760548A7 (enrdf_load_html_response) | 1976-09-13 |
| DK137274C (enrdf_load_html_response) | 1978-07-17 |
| PT64886A (fr) | 1976-03-31 |
| SE7603053L (sv) | 1976-09-13 |
| JPS51113864A (en) | 1976-10-07 |
| FR2303540B1 (enrdf_load_html_response) | 1979-07-20 |
| GB1546701A (en) | 1979-05-31 |
| AU1197076A (en) | 1977-09-15 |
| IE43704B1 (en) | 1981-05-06 |
| IE43704L (en) | 1976-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |