ES247882A1 - New 2-basically substituted indene compounds - Google Patents
New 2-basically substituted indene compoundsInfo
- Publication number
- ES247882A1 ES247882A1 ES0247882A ES247882A ES247882A1 ES 247882 A1 ES247882 A1 ES 247882A1 ES 0247882 A ES0247882 A ES 0247882A ES 247882 A ES247882 A ES 247882A ES 247882 A1 ES247882 A1 ES 247882A1
- Authority
- ES
- Spain
- Prior art keywords
- lower alkyl
- acid
- benzyl
- tertiary amino
- reacting
- 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
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- -1 alkyl Grignard reagent Chemical class 0.000 abstract 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000001204 N-oxides Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- 239000003826 tablet Substances 0.000 abstract 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
- HFLYLOMENQCOGF-UHFFFAOYSA-N 3-benzyl-5-(dimethylamino)-1-phenylpentan-2-one Chemical compound C(C1=CC=CC=C1)C(C(CC1=CC=CC=C1)=O)CCN(C)C HFLYLOMENQCOGF-UHFFFAOYSA-N 0.000 abstract 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 abstract 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000012445 acidic reagent Substances 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229940125715 antihistaminic agent Drugs 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0912684/IV (b)/1> and their acid addition and quaternary ammonium salts and N-oxides wherein A represents a C1-7 alkylene group, A1 represents a C2-7 alkylene chain containing at least 2 carbon atoms in the said chain, R1 and R2 represent hydrogen or halogen atoms, or C1-7 alkyl or alkoxy groups, R3 and R4 represent alkyl or cycloalkyl groups having at most 7 carbon atoms or they form together with the amino nitrogen atom a heterocyclic ring which can be interrupted by a further nitrogen, oxygen or sulphur atom, and R5 is a hydrogen atom or a methyl group. The compounds of the invention may be prepared by reacting an appropriate 2-tertiary amino-lower alkylindane-1-one with an aryl-lower alkyl Grignard reagent or with an aryl lower alkyl metal compound, especially an alkali metal compound, and if necessary, isolating and dehydrating the 3-aryl-lower alkyl-2-tertiary amino-lower alkyl-indane-1-ols so formed, by treatment with an acid reagent. The compounds may also be prepared by cyclizing a 3-aryl-5-tertiary amino-lower alkyl-1-phenylpentane-2-one with polyphosphoric acid. The N-oxides are prepared by reacting the bases with hydrogen peroxide and the quaternary ammonium salts by reacting the base with an ester formed from a hydroxylated hydrocarbon compound and a strong inorganic or organic base. The 2-tertiary amino-lower alkyl-indane-1-ones used as starting materials are prepared by esterifying an appropriate a -benzyl-malonic acid to form a lower alkyl or a tetrahydropyranyl ester, reacting this with a reactive ester of a tertiary amino alkanol and an acid to form the corresponding a -benzyl-tertiary amino-lower alkyl-malonic acid ester, hydrolysing this to the di-acid, decarboxylating the diacid to the mono-acid and cyclizing the lastnamed in the presence of polyphosphoric acid. The malonic ester may also be cyclized direct. 3-Benzyl-5-dimethylamino-1-phenyl-pentane-2-one is prepared by reacting diethyl a -benzyl-a -(21-dimethylaminoethyl)-malonate with potassium hydroxide to form ethyl a -(21-dimethylaminoethyl)b -phenyl propionate and treating this with benzyl magnesium chloride. Pharmaceutical compositions useful as antihistamines comprise compounds of the invention in admixture or in conjunction with a pharmaceutical carrier. The compositions may be in a form suitable for oral, parenteral or topical administration, e.g. tablets, capsules, dragees, solutions, suspensions, emulsions, salves and creams, and may contain other therapeutically useful substances. An example is given of a tablet containing 3-benzyl-2-(21-dimethylaminoethyl)indene hydrochloride.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72264158A | 1958-03-20 | 1958-03-20 | |
| US74432858A | 1958-06-25 | 1958-06-25 | |
| US78531459A | 1959-01-07 | 1959-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES247882A1 true ES247882A1 (en) | 1959-12-16 |
Family
ID=27419038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0247882A Expired ES247882A1 (en) | 1958-03-20 | 1959-03-13 | New 2-basically substituted indene compounds |
Country Status (3)
| Country | Link |
|---|---|
| CH (3) | CH394229A (en) |
| ES (1) | ES247882A1 (en) |
| GB (1) | GB912684A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10033459A1 (en) * | 2000-07-10 | 2002-01-24 | Gruenenthal Gmbh | Cyclic substituted aminomethyl compounds and drugs containing them |
-
1959
- 1959-03-11 CH CH7065659A patent/CH394229A/en unknown
- 1959-03-11 CH CH1416263A patent/CH391723A/en unknown
- 1959-03-11 CH CH1416163A patent/CH391722A/en unknown
- 1959-03-13 ES ES0247882A patent/ES247882A1/en not_active Expired
- 1959-03-20 GB GB9814/59A patent/GB912684A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB912684A (en) | 1962-12-12 |
| CH391723A (en) | 1965-05-15 |
| CH391722A (en) | 1965-05-15 |
| CH394229A (en) | 1965-06-30 |
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