GB1167712A - Diarylcyclopropane Derivatives - Google Patents
Diarylcyclopropane DerivativesInfo
- Publication number
- GB1167712A GB1167712A GB3819/67A GB381967A GB1167712A GB 1167712 A GB1167712 A GB 1167712A GB 3819/67 A GB3819/67 A GB 3819/67A GB 381967 A GB381967 A GB 381967A GB 1167712 A GB1167712 A GB 1167712A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- amino
- compound
- diphenylcyclopropane
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
Abstract
1,167,712. Diarylcyclopropane derivatives. WHITEFIN HOLDING S.A. 25 Jan., 1967 [26 Jan., 1966], No. 3819/67. Divided out of 1,167,711. Heading C2C. Novel diaryloyclopropane derivatives of Formula I in which each of Ar 1 and Ar 2 is an aryl radical optionally carrying one or more halogen, C 1-6 alkyl, C 1-6 alkoxy, trifluoromethyl, hydroxy, nitro, amino or mono- or di-(C 1-6 alkyl)- amino substituents, R 1 is hydrogen, C 1-6 alkyl, hydroxy-C 1-6 alkyl, amino-C 1-6 alkyl, N-monosubstituted amino-C 1-6 alkyl or N,N-disubstituted amino-C 1-6 alkyl, R 2 is hydrogen, C 1-6 alkyl, cycloalkyl, aryl-C 1-6 alkyl, aryloycloalkyl- C 1-6 alkyl, hydroxy C 1-6 alkyl, halo-C 1-6 alkyl, amino-C 1-6 alkyl, N-monosubstituted amino-C 1-6 alkyl, N,N-disubstituted amino- C 1-6 alkyl or acyl which may be substituted, or R 1 and R 2 , together with the nitrogen atom to which they are attached, represent a heterocyclic ring which may contain other heteroatoms which in turn may be substituted, and their salts with pharmaceutically acceptable acids and their quaternary ammonium salts with C 1-6 alkyl halides, are prepared by (a) reacting an appropriate 1 .halomethyl-2,3-diarylcyclopropane with an amine of formula HNR 1 R 2 , or (b) reducing a compound of Formula II in which Ar 1 , Ar 2 , R 1 and R 2 are as defined above except that R 2 is not acyl, or (c) reacting a compound of Formula III with a compound of formula R 2 Y in which R 2 is as defined above except for hydrogen and Y is halogen, or (d) reacting a compound of Formula I in which R 2 is haloalkyl or haloalkylcarbonyl with a primary or secondary amine in the presence of an acid binding agent and a solvent, in a sealed tube at a tempeiature above 50 C., and reducing the compound obtained of Formula I, in which R 2 is a mono- or di-substituted aminoalkyl or aminoalkylcarbonyl group, with LiAlH 4 in a solvent at from 35 to 110 C. 1 - Chloromethyl - 2,3 - cis,trans - diphenylcyclopropane is prepared by reducing 2,3-cis, trans - diphenylcyclopropane - 1 - carboxylic acid and treating the resulting 2,3-cis,trans-diphenylcyclopropane - 1 - carbinol with thionyl chloride. Pharmaceutical compositions having central nervous system stimulant activity, for oral, parenteral or rectal administration, comprise a compound of Formula I or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof, together with a carrier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3819/67A GB1167712A (en) | 1966-01-26 | 1966-01-26 | Diarylcyclopropane Derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3819/67A GB1167712A (en) | 1966-01-26 | 1966-01-26 | Diarylcyclopropane Derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1167712A true GB1167712A (en) | 1969-10-22 |
Family
ID=9765519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3819/67A Expired GB1167712A (en) | 1966-01-26 | 1966-01-26 | Diarylcyclopropane Derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1167712A (en) |
-
1966
- 1966-01-26 GB GB3819/67A patent/GB1167712A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |