GB923854A - New indene compounds and pharmaceutical preparation containing them - Google Patents
New indene compounds and pharmaceutical preparation containing themInfo
- Publication number
- GB923854A GB923854A GB2763059A GB2763059A GB923854A GB 923854 A GB923854 A GB 923854A GB 2763059 A GB2763059 A GB 2763059A GB 2763059 A GB2763059 A GB 2763059A GB 923854 A GB923854 A GB 923854A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lower alkyl
- tertiary amino
- pyridyl
- prepared
- indan
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises: indenes substituted in the 2-position by a tertiary amino-lower alkyl group (in which the tertiary amino group is a di-(C1-C5 alkyl)-amino group or an N,N-alkyleneimino group having 5 or 6 ring members, whose alkylene chain chain may be interrupted by nitrogen, oxygen or p sulphur and which may be substituted by methyl groups, and the lower alkylene linking group contains 1-5 carbon atoms of which preferably 2 or 3 are in a straight chain between the nucleus and the N atom), substituted in the 3-position by a pyridyl-lower alkyl group (in which the pyridine ring is preferably unsubstituted but may be halogen- or C1-C5 alkyl- or alkoxy-substituted, and the alkylene linking group contains 1-3 carbon atoms), unsubstituted or C1-C5 alkyl - substituted in the 1 - position, and unsubstituted or halogen or C1-C5 alkyl- or alkoxy-substituted in the benzene ring), and their acid addition salts, quaternary ammonium compounds and N-oxides (in which the oxygen atom is attached to the nitrogen atom of the tertiary amino group); the preparation thereof by the following processes: (1) dehydrating a correspondingly substituted indan-1-, -2- or -3-ol, or one containing, instead of a tertiary amino group, a substituent subsequently converted thereto or replaced thereby, (2) shifting the double bond, by the action of an acid or base and/or by heating, in a correspondingly substituted D 2-indene, or one containing, instead of a tertiary amino group, a substituent subsequently converted thereto or replaced thereby, or (3) reducing (with shifting of the D 2-double bond) a 1-(pyridyl-lower alkylidene)-D 2-indene substituted in the 2-position in the same way as the starting materials in (1) and (2), and in all cases, if desired, converting a resulting acid addition salt into a free base by the action of alkali, or converting a resulting free base into an addition salt by reaction with an acid, into a quaternary ammonium salt by the action of an ester of an alkanol with a strong inorganic or organic acid, or into an N-oxide by the action of hydrogen peroxide in alcoholic solution; and pharmaceutical preparations containing the products in admixture or conjunction with a pharmaceutically suitable diluent. 1-Pyridyl-lower alkyl-2-tertiary amino-lower alkyl-indan-1-ols are prepared by reacting 2-tertiary amino-lower alkyl-indan-1-ones with pyridyl-lower alkyl metal compounds of groups Ia, IIa or IIb of the periodic system, especially lithium compounds, or with alkali metal salts of alkali metal pyridine lower alkanoic acids. 2-Tertiary amino-lower alkyl-indan-1-ones are prepared by reacting an a -benzylmalonic ester with a reactive ester of a tertiary amino-lower alkanol, preferably in the presence of an alkali metal alcoholate, and cyclizing the resulting ester, e.g. by hydrolysing and decarboxylating it, and heating the resulting substituted acetic acid with a Lewis acid. a -Benzylmalonic esters are prepared by reacting benzyl halides with sodiomalonic esters. Pyridyl-lower alkyl lithium compounds are prepared by reacting a lower alkyl-pyridine with an aryl or alkyl lithium, or reacting an ether of a pyridyl-lower alkanol and a lower alkanol with lithium. 1-Pyridyl-lower alkyl-2-tertiary amino-lower alkyl-indan-2-ols are prepared by reacting 1-pyridyl-lower alkylindan-2-ones with etherified hydroxy-lower alkyl Grignard reagents and then replacing the etherified hydroxy group by a tertiary amino group. 1-Pyridyl-lower alkyl-indan-2-ones are prepared by condensing indan-2-ones with pyridyl-lower alkyl-aldehydes in the presence of a base and reducing the resulting alkylidene compounds. 1-Pyridyl-lower alkyl-2-tertiary amino-lower alkyl-indan-3-ones are prepared by reacting 2-lower alkoxy-lower alkyl-3-lower alkoxy-inden-1-ones with pyridyl-lower alkyl metal compounds, dehydrating the products, hydrogenating the resulting double bond, converting the enol ether group to a 3-oxo group and reducing this, and finally replacing the lower alkoxy group by a tertiary amino group. 2-Lower alkoxy-lower alkyl-3-lower alkoxyinden-1-ones are prepared by reacting a lower alkyl phthalate with a lower alkoxy-lower alkyl-nitrile in the presence of a base and converting the resulting lower alkoxy-lower alkyl-indane-1,3-dione to its enol ether by treatment with an alcohol in the presence of an acid, or with a diazoalkane. 1-Pyridyl-lower alkyl-2-tertiary amino lower alkyl-D 2-indenes are prepared by reacting a 1-methyl-2-tertiary amino-lower alkyl-indene with a pyridine-lower alkyl-aldehyde in the presence of a base and reducing the resulting alkylidene compound. 1-(Pyridyl-lower alkylidene)-2-tertiary amino-lower alkyl D 2-indenes are prepared by condensing a 2-tertiary amino-lower alkyl-indene with a pyridyl-lower alkanol or with a lower alkenyl-pyridine. Di-tetrahydropyranyl a -benzylmalonate is prepared by reacting a -benzylmalonic acid with dihydropyran in ether in the presence of p-toluenesulphonic acid. 2-(2- Dimethylaminoethyl)- indene hydrochloride is prepared by reducing 2-(2-dimeth aminoethyl)-indan-1-one with sodium borohydride and refluxing the resulting 2-(2-dimethylaminoethyl)-indan-1-ol (the picrate of which is described) with concentrated hydrochloric acid and glacial acetic acid. 2-(3-Dimethylaminoethyl)-indene hydrochloride is prepared analogously. The pharmaceutical preparations, which have antihistaminic, sedative, tranquillizing and local anaesthetic action, may be in forms suitable for enteral, parenteral or topical administration, e.g. tablets, dragees, salves, creams, solutions, suspensions or emulsions.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US75452658A | 1958-08-12 | 1958-08-12 | |
US771225A US2970149A (en) | 1958-11-03 | 1958-11-03 | Certain 1-[(2-pyridyl)-lower alkyl]-2-(tertamino-lower alkyl)-indan-1-ols, and acid addition salts |
US792263A US3076804A (en) | 1959-02-10 | 1959-02-10 | 2-(n, n-di-loweralkyl-amino-loweralkyl)-1-[pyridyl-methylidene]-indene and process |
US81099859A | 1959-05-05 | 1959-05-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB923854A true GB923854A (en) | 1963-04-18 |
Family
ID=27505666
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2763059A Expired GB923854A (en) | 1958-08-12 | 1959-08-12 | New indene compounds and pharmaceutical preparation containing them |
Country Status (3)
Country | Link |
---|---|
CH (3) | CH383378A (en) |
DE (1) | DE1283842B (en) |
GB (1) | GB923854A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2337518A (en) * | 1998-05-20 | 1999-11-24 | Samsung Electronics Co Ltd | Malonate dissolution inhibitor |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2441069A (en) * | 1943-08-20 | 1948-05-04 | Ciba Pharm Prod Inc | 2-amino-methyl-indenes and their production |
-
1959
- 1959-07-27 CH CH271664A patent/CH383378A/en unknown
- 1959-07-27 CH CH271764A patent/CH383969A/en unknown
- 1959-07-27 CH CH7624959A patent/CH384575A/en unknown
- 1959-08-01 DE DE1959C0019532 patent/DE1283842B/en active Pending
- 1959-08-12 GB GB2763059A patent/GB923854A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2337518A (en) * | 1998-05-20 | 1999-11-24 | Samsung Electronics Co Ltd | Malonate dissolution inhibitor |
US6165680A (en) * | 1998-05-20 | 2000-12-26 | Samsung Electronics Co., Ltd. | Dissolution inhibitor of chemically amplified photoresist and chemically amplified photoresist composition containing the same |
GB2337518B (en) * | 1998-05-20 | 2003-10-08 | Samsung Electronics Co Ltd | Dissolution inhibitor of chemically amplified photoresist and chemically amplified photoresist composition containing the same |
Also Published As
Publication number | Publication date |
---|---|
CH383969A (en) | 1964-11-15 |
CH384575A (en) | 1964-11-30 |
CH383378A (en) | 1964-10-31 |
DE1283842B (en) | 1968-11-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Smolinsky | Vinyl azene chemistry: Formation of azacyclopropene | |
US5646283A (en) | Tetracyclic compound | |
US3830803A (en) | 5-loweralkyl-1-phenyl-1,3,4,6-tetrahydro-5h-benz(f)-2,5-oxazocines and 4-ones | |
GB923854A (en) | New indene compounds and pharmaceutical preparation containing them | |
Tani | The Reaction of N-Alkoxypyridinium Derivatives.(2) | |
US3499901A (en) | Partially hydrogenated phenanthridines | |
GB1070362A (en) | Novel dibenzocycloheptatriene derivatives and a process for their manufacture | |
Potts et al. | Synthetic Experiments Related to the Indole Alkaloids. III. The Reductive Cyclization of 1-[2-(3-Indolyl)-2-oxoethyl] pyridinium Salts to Quinolizine Derivatives Related to the Indole Alkaloids1 | |
US2857394A (en) | Heterocyclic compounds | |
US3808263A (en) | 6,6-dimethyl-9-alkyl-9-azabicyclo(3.3.1)nonan-3-ols | |
TSUDA et al. | Studies on the Synthesis of Matrine. II. The Synthesis of Octadehydromatrine and Allomatridine1 | |
US3753992A (en) | Process and intermediates for quinine,quinidine and derivatives thereof | |
US2727907A (en) | Derivatives of 16-alkanoyloxy-17alpha-hydroxypregnen-20-ones | |
US3821214A (en) | Oxazine derivatives | |
US3301866A (en) | Substituted indenopyridines | |
US3518283A (en) | Pivaloyl and undecanoyl esters of griseofulvol | |
US3531491A (en) | Certain 6-hexanoyl or 6-(1-hydroxyhexyl)bicyclo(2.2.1)hept - 2 - ene - 5 - carboxylic acids,esters thereof and 5-ylketones | |
MAEDA et al. | Study on the Synthesis of rac-3-Methoxy-6-oxo-N-methylmorphinan | |
US3518272A (en) | Tetrahydro benzopyranoquinolines and process for their production | |
US2986562A (en) | Reserpic and deserpidic acid lactone dienes | |
US3502669A (en) | 3-azabicyclo(3,3,1)nonane derivatives | |
US3462447A (en) | Certain azadibenzocycloheptene-5-ols and ethers derivatives thereof | |
US3781311A (en) | Novel preparation of trienic steroids | |
US3479363A (en) | 1-naphthenyl- and 1-indenyl-4-substituted phenyl-4-carboxyalkyl piperidines | |
Bailey et al. | The constitution of conessine. Part VII. Degradation of some reduced quinoline and indole bases |