GB1111336A - Aryl ketones - Google Patents
Aryl ketonesInfo
- Publication number
- GB1111336A GB1111336A GB29814/64A GB2981464A GB1111336A GB 1111336 A GB1111336 A GB 1111336A GB 29814/64 A GB29814/64 A GB 29814/64A GB 2981464 A GB2981464 A GB 2981464A GB 1111336 A GB1111336 A GB 1111336A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- phenyl
- carbon
- alkyl
- r8nr9r10
- 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 Aryl ketones Chemical class 0.000 title abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000011592 zinc chloride Substances 0.000 abstract 2
- 235000005074 zinc chloride Nutrition 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 abstract 1
- LBXGBNHUNHWYRM-UHFFFAOYSA-N 2,3-dimethoxybenzonitrile Chemical compound COC1=CC=CC(C#N)=C1OC LBXGBNHUNHWYRM-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000003569 amebicidal effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
-
- 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
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
-
- 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
- C07C45/74—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 combined with dehydration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Novel ketones of the formula <FORM:1111336/C2/1> in which X os a carbonyl group, one of R2 and R3 is a group OR7, R7 and R1 being H, alky or a group R8NR9R10, R8 being alkylene, R9 and R10 being H or alkyl or forming a heterocyclic ring at least one of R1 and R7 being a group R8NR9R10); R4, R5 and the othe of R2 and R3 are H, alkyl, aralkyl or halogen, R6 is naphthyl, phenyl, alkenyl and/or halogen-substituted aryl and Y is a carbon-carbon bond or a saturated or unsaturated divalent group containing carbon and hydrogen only Y having at least 2 carbon atoms when R6 is phenyl and R4, R5 and one of R2 and R3 are all hydrogen are prepared by (i) condensing a dihydroxy benzene with a carboxylic acid or its derivative R6YA, where A is -COOH, -COCl or -CN; or (ii) reacting a dimethoxybenzonitrile with a Grignard reagent R6YMgHal; or (iii) condensing a dimethoxyacetophenone with an aldehyde R6WCHO, in which W is a group corresponding to Y, to form an a -b unsaturated ketone which may be hydrogenated if desired. The reaction (i) preferably uses ZnCl2 as catalyst if the acid is used, AlCl3 with the chloride and HCl and ZnCl2 with the cyanide. The product of (i) may be etherified, e.g. using an alkyl halide in acetone solution in the presence of an acid binding agent. The product of (ii) or (iii) may be demethylated. Exemplified products have R1 and R2 hydroxy, either or both of which may be etherified to b -diethyl aminoethoxy or b -N-morpholinoethoxy, or R1 and R3 methoxy, and also may have R5 chloro, R6 phenyl and p-chlorophenyl and Y ethylene, propylene, butylene, butadienylene and -CH = CH-. Pharmaceutical preparations having amoebicidal activity comprise the above compounds in conjunction with a conventional diluent or carrier.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29814/64A GB1111336A (en) | 1964-07-24 | 1964-07-24 | Aryl ketones |
| GB34309/66A GB1111337A (en) | 1964-07-24 | 1964-07-24 | Substituted aralkyl alcohols |
| GB34310/66A GB1111338A (en) | 1964-07-24 | 1964-07-24 | Aralkyl substituted resorcinols |
| CH1016165A CH441370A (en) | 1964-07-24 | 1965-07-20 | Process for the preparation of new compounds |
| DE19651493729 DE1493729A1 (en) | 1964-07-24 | 1965-07-22 | Process for the production of pharmaceutical preparations |
| FR25801A FR5003M (en) | 1964-07-24 | 1965-07-23 | |
| FR25802A FR1499864A (en) | 1964-07-24 | 1965-07-23 | Process for the preparation of arylketones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29814/64A GB1111336A (en) | 1964-07-24 | 1964-07-24 | Aryl ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111336A true GB1111336A (en) | 1968-04-24 |
Family
ID=10297608
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34309/66A Expired GB1111337A (en) | 1964-07-24 | 1964-07-24 | Substituted aralkyl alcohols |
| GB29814/64A Expired GB1111336A (en) | 1964-07-24 | 1964-07-24 | Aryl ketones |
| GB34310/66A Expired GB1111338A (en) | 1964-07-24 | 1964-07-24 | Aralkyl substituted resorcinols |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34309/66A Expired GB1111337A (en) | 1964-07-24 | 1964-07-24 | Substituted aralkyl alcohols |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34310/66A Expired GB1111338A (en) | 1964-07-24 | 1964-07-24 | Aralkyl substituted resorcinols |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH441370A (en) |
| DE (1) | DE1493729A1 (en) |
| FR (2) | FR1499864A (en) |
| GB (3) | GB1111337A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4732896A (en) * | 1981-12-24 | 1988-03-22 | Delalande S.A. | Aromatic derivatives comprising an aminoalkoxy chain, the salts thereof, the process for preparing these derivatives and salts and the application thereof in therapeutics |
| US4945099A (en) * | 1987-01-12 | 1990-07-31 | Eli Lilly And Company | Anti-inflammatory agents |
| US5098613A (en) * | 1987-01-12 | 1992-03-24 | Eli Lilly And Company | Anti-inflammatory agents |
| EP0476658A1 (en) * | 1990-09-20 | 1992-03-25 | Merrell Dow Pharmaceuticals Inc. | 1-Phenyl-3-phenyl-2-propyne-1-ones |
| US5294613A (en) * | 1987-01-12 | 1994-03-15 | Eli Lilly And Company | Method of treating endotoxic shock in mammals |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2518992A1 (en) * | 1981-12-24 | 1983-07-01 | Delalande Sa | 1-Amino-omega-aryloxy substd. ethane and propane derivs. - with calcium antagonising activity e.g. for treating angina |
| FR2537970B1 (en) * | 1982-12-15 | 1986-08-14 | Delalande Sa | NOVEL AMINOALKOXY AROMATIC DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION IN THERAPEUTICS |
| CA1315279C (en) * | 1987-01-12 | 1993-03-30 | Nancy Grace Bollinger | Anti-inflammatory agents |
| DE3825559A1 (en) * | 1988-07-28 | 1990-02-01 | Basf Ag | P-HYDROXIPHENONE DERIVATIVES AND THEIR USE |
| FR2670205A1 (en) * | 1990-12-06 | 1992-06-12 | Rhone Poulenc Agrochimie | 2,6-ALKOXYPENYL ALKYLCETONE AND DERIVATIVES HERBICIDES. |
| NO300539B1 (en) * | 1992-11-30 | 1997-06-16 | Sankyo Co | alpha, omega-diarylalkane derivatives, with therapeutic activity for the treatment and prevention of circulatory disorders and psychoses, and pharmaceutical preparations containing these derivatives |
-
1964
- 1964-07-24 GB GB34309/66A patent/GB1111337A/en not_active Expired
- 1964-07-24 GB GB29814/64A patent/GB1111336A/en not_active Expired
- 1964-07-24 GB GB34310/66A patent/GB1111338A/en not_active Expired
-
1965
- 1965-07-20 CH CH1016165A patent/CH441370A/en unknown
- 1965-07-22 DE DE19651493729 patent/DE1493729A1/en active Pending
- 1965-07-23 FR FR25802A patent/FR1499864A/en not_active Expired
- 1965-07-23 FR FR25801A patent/FR5003M/fr not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4732896A (en) * | 1981-12-24 | 1988-03-22 | Delalande S.A. | Aromatic derivatives comprising an aminoalkoxy chain, the salts thereof, the process for preparing these derivatives and salts and the application thereof in therapeutics |
| US4945099A (en) * | 1987-01-12 | 1990-07-31 | Eli Lilly And Company | Anti-inflammatory agents |
| US5098613A (en) * | 1987-01-12 | 1992-03-24 | Eli Lilly And Company | Anti-inflammatory agents |
| US5294613A (en) * | 1987-01-12 | 1994-03-15 | Eli Lilly And Company | Method of treating endotoxic shock in mammals |
| EP0476658A1 (en) * | 1990-09-20 | 1992-03-25 | Merrell Dow Pharmaceuticals Inc. | 1-Phenyl-3-phenyl-2-propyne-1-ones |
Also Published As
| Publication number | Publication date |
|---|---|
| CH441370A (en) | 1967-08-15 |
| GB1111337A (en) | 1968-04-24 |
| DE1493729A1 (en) | 1969-01-30 |
| GB1111338A (en) | 1968-04-24 |
| FR5003M (en) | 1967-04-17 |
| FR1499864A (en) | 1967-11-03 |
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