SU420166A3 - METHOD OF OBTAINING PENTACYCLIC COMPOUNDS - Google Patents

Description

one

The present invention relates to the preparation of new pentacyclic compounds not described in the literature, for example, 4c, 8c, 8c, 8d-tetrahydrodibenzo- (a, f) -cyclonrop (c, d) -pentol compounds with valuable pharmacological properties.

The literature describes a process for the preparation of 10-substituted dibenzocyclohetadienes, which are pharmacologically active compounds and therefore can be used in medicine as pharmaceutical preparations.

However, in the literature, there are no reports on the preparation of 4, в, 8в, 8с, 8d-tetrahydride; o (a, G) -cyclocrop- (c, e) -pentalene compounds, which have high pharmacological activity.

According to the invention, a method for producing pentacyclic compounds of the general formula is described.

F

l /

i alKAtfi ъ

where Phi and Ph2 are a substituted or unsubstituted 1,2-phenylenated residue;

alk is a lower alkylene residue;

Am is the primary or secondary amino group;

RI is hydrogen, an esterified ester or ester hydroxy group, an aliphatic, araliphatic or aromatic residue;

R2 and Rs are hydrogen, free or esterified into an ether or ester of an oxy group or aliphatic residue, or their derivatives, in that in a compound of the general formula

2 T}

15

Pli,

Ph,

Kj

where Phi, Ph2, Ri, R2 and Rs - have the indicated meanings;

X - (isocyanato or esterified into carboxy amino ester) - lower alkyl group;

translates the indicated residue X into a group of the formula - alk-Am;

where: alk and Am - have the indicated values, in a known manner, by hydrolysis, followed by isolation of the target product in a known manner in free form or by transferring it to the corresponding derivative with nitrogen, for example acyl, oxide, quaternary ammonium compound or salt, as a racemate or optically -active antipode.

The 1,2-phenylene residues of Phj and Ph2 may contain one or more, preferably one or two, identical or different substituents in the remaining four positions, for example methyl, ethyl, n-propyl, isopropyl, n-butyl or isobutyl; free, esterified in simple or slol: hydroxyl ether or mercapto group, metoxy, cryptomers, H-propyloxy, izopropyloxy, n-butyloxy or isobutyloxy, methylmercapto or ethyl mercaptogroup, acetylxy-groups, acetyloxy, or methylmer; a nitro, amino, in particular a di-lower alkylamino group, for example a dimethylaminoyl diethylamino group or an acetyl, propionyl or pivaloyl; or methylsulfonyl or

ethylsulfonyl.

The lower alkylene group alk means methylene, 1,1- or 1,2-ethylene or 1,1-1,2-, 2,2-, or 1,3-propylene, as well as 1,1-, 1,2- 2,2-, 1,3-, 2,3- or 1,4-butylene.

The amine group Am is a primary, predominantly secondary amino group, containing predominantly one substituent of aliphatic character or one substituent of aromatic character. Such amino groups are e.g. methylamino, ethylamino, isobutylamino, cycloalkylamino or cycloalkyl- lower alkylamino 3-7 cyclic units, e.g. tsiklopropilamino-, tsiklopentilamino-, tsiklogeksilamino- tsiklopropilmetilaminogruppa or aryl-lower alkylamino, arylamino, where aryl means a phenylene residue, which may be substituted as well as the indicated groups

Phi and Pha.

The aliphatic residues Ri, R2 or Kz are allyl, and these residues may contain functional groups, for example, free hydroxyl groups, esterified into ethers or esters, primary, secondary or tertiary amino groups and / or keto groups as substituents. Substituted aliphatic residues are, for example, hydroxy, methoxy, ETOXI, chloro, dimethylamino, carboxy or carbomethoxy methyl, formyl, carboxy or carboxy alkoxy, for example carbomethoxy or carboxyl, 1- or 2- (hydroxy, METHOXY-, ETOXI-, chloro-, dimethylamino-, carboxy- or carbomethoxy) -ethyl or -propyl, or acetyl, or pyvalloyl.

The araliphatic or aromatic residue of RI is, for example, aryl-lower alkyl, aryl-lower alkanoyl, or aryloxy-lower alkyl or aryl, where aryl means a phenylene residue that can be substituted in the same way as the Phi and Phs groups, for example benzyl or 1- or 2 phenylethyl; benzoyl or phenylacetyl; a-hydroxybenzyl; phenyl; tolyl, anisyl, halophenyl, nitrophenyl, aminophenyl or acetylphenyl. The residue 7 means predominantly hydrogen, halogen, lower alkyl, hydroxy lower alkyl, Arp lower alkyl, carboxyl, carboxy lower alkoxy, and each of the residues R2 and R means mainly hydrogen, lower alkoxy, halo, lower alkyl hydroxy lower

alkyl, halogeno-lower alkyl, for example, trifluoromethyl, carboxyl or carbo-lower alkoxy.

Esterified in the carboxyamino lower alkyl group ester means

carbo-lower alkoxyamino lower alkyl group.

The starting isocyanates and urethanes can be hydrolyzed, for example, with aqueous mineral acids or alkali hydroxides.

.metalov.

The compounds obtained can be converted into one another by well-known methods. For example, the resulting primary amines can be reacted with reactive ester alcohols to produce amine compounds. The resulting secondary or primary amines can also be acylated by treatment with acid halides or anhydrides. Received

The acyl compounds can be hydrolyzed, for example by exposure to acids or alkali metal hydroxides, or, for example, by exposure to simple or complex light metal hydrides, to be reduced.

Further, the nitro groups can be introduced into aromatic residues, for example, by treatment with nitric acid in the presence of sulfuric acid, or by pyrolysis of nitrate salts

mainly in an acidic environment. Existing nitro groups can be reduced by hydrogen at the time of isolation.

The resulting hydroxy compounds, where Ri is a hydroxy-lower alkyl residue, can be esterified into an ether and / or ester using known methods.

The resulting acids can be esterified into an ester by treatment with alcohols in the presence of a strong acid, for example hydrochloric acid, sulfuric acid, benzenesulfonic acid or / g-toluene sulfonic acid, as well as corresponding condensing agents, for example dicyclocarbodiimide, or diazo compounds. Received esters

It is possible to hydrolyze in the presence of acidic or fixed assets, for example, mineral acids or complex acids of heavy metals, as well as alkali metal carbonates or alkali metal alkoxides.

or transesterify to esters. The acid obtained can be decarboxylated by a well-known method, for example, by pyrolysis in the absence or presence of a catalyst, or it can be converted into a salt. The resulting isomeric mixtures may be generally known.