GB1380089A - 2-aryl-1,3-indandiones - Google Patents
2-aryl-1,3-indandionesInfo
- Publication number
- GB1380089A GB1380089A GB275872A GB275872A GB1380089A GB 1380089 A GB1380089 A GB 1380089A GB 275872 A GB275872 A GB 275872A GB 275872 A GB275872 A GB 275872A GB 1380089 A GB1380089 A GB 1380089A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- halogen
- reacting
- indandiones
- alkyl
- 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
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000000954 anitussive effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229940124584 antitussives Drugs 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- -1 m-anisyl Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000014508 negative regulation of coagulation Effects 0.000 abstract 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
-
- 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
- C07C45/63—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 introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07C45/673—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 change of size of the carbon skeleton
-
- 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
- C07C45/72—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1380089 2-aryl-1,3-indandiones ISTITUTO GENTILI-PISA SpA 20 Jan 1972 2758/72 Heading C2C The invention comprises compounds of formula wherein R is H, halogen, CH 2 OH or alkyl; Ar is Ph, 1 or 2 naphthyl, or m-anisyl, -halophenyl, -tolyl or -trifluoromethylphenyl; and X is 4- or 5- halogen, alkyl, CF 3 , CO 2 H, OH, NH 2 , NO 2 or OCOR<SP>11</SP> where R<SP>11</SP> is Me, Et, CF 3 , Ph or PhCH 2 . In examples, these compounds are prepared by (1) reacting an X-substituted phthalic acid or anhydride with ArCH 2 CO 2 H in presence of Ac 2 O and Et 3 N (for R=H); (2) reacting I (R = H) with Br 2 or CH 2 O (for R=Br or OH 2 OH, respectively); or (3) hydrolysing I (X=OAc), to give I(X=OH). Therapeutic compositions comprise compounds of the above formula, and are stated to have antiinflammatory, analgesic, antitussive, uricosuri and (in certain cases) anticoagulant activity.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB275872A GB1380089A (en) | 1972-01-20 | 1972-01-20 | 2-aryl-1,3-indandiones |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB275872A GB1380089A (en) | 1972-01-20 | 1972-01-20 | 2-aryl-1,3-indandiones |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1380089A true GB1380089A (en) | 1975-01-08 |
Family
ID=9745341
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB275872A Expired GB1380089A (en) | 1972-01-20 | 1972-01-20 | 2-aryl-1,3-indandiones |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1380089A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0008540A2 (en) * | 1978-08-24 | 1980-03-05 | Union Carbide Corporation | 2-aryl-1,3-indandione derivatives and compositions comprising them for controlling ectoparasitic acarina |
EP0138272A1 (en) * | 1983-10-14 | 1985-04-24 | Akzo N.V. | Diarylindane-1,3-diones, their preparation and use |
EP0398258A1 (en) * | 1989-05-16 | 1990-11-22 | Mitsubishi Kasei Corporation | Indan-1,3-dione derivative and herbicidal composition containing the same as active ingredient |
WO1998055439A1 (en) * | 1997-06-05 | 1998-12-10 | Venantius Limited | Indane compounds and their pharmaceutical use |
-
1972
- 1972-01-20 GB GB275872A patent/GB1380089A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0008540A2 (en) * | 1978-08-24 | 1980-03-05 | Union Carbide Corporation | 2-aryl-1,3-indandione derivatives and compositions comprising them for controlling ectoparasitic acarina |
EP0008540B1 (en) * | 1978-08-24 | 1984-10-24 | Union Carbide Corporation | 2-aryl-1,3-indandione derivatives and compositions comprising them for controlling ectoparasitic acarina |
EP0138272A1 (en) * | 1983-10-14 | 1985-04-24 | Akzo N.V. | Diarylindane-1,3-diones, their preparation and use |
EP0398258A1 (en) * | 1989-05-16 | 1990-11-22 | Mitsubishi Kasei Corporation | Indan-1,3-dione derivative and herbicidal composition containing the same as active ingredient |
US5076830A (en) * | 1989-05-16 | 1991-12-31 | Mitsubishi Kasei Corporation | Indan-1,3-dione derivative and herbicidal composition containing the same as active ingredient |
US5110342A (en) * | 1989-05-16 | 1992-05-05 | Mitsubishi Kasei Corporation | Indan-1,3-dione derivative and herbicidal composition containing the same as active ingredient |
WO1998055439A1 (en) * | 1997-06-05 | 1998-12-10 | Venantius Limited | Indane compounds and their pharmaceutical use |
US6433021B1 (en) | 1997-06-05 | 2002-08-13 | Venantius Limited | Indane compounds and their pharmaceutical use |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |