# US 4,395,413 A · Oxime ethers and pharmaceutical compositions containing the same

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- Number: US 4,395,413 A
- Document ID: US4395413A
- Status: Granted
- Kind: A
- Application number: 06/162,674
- Filed: 1980-06-24
- Granted: 1983-07-26
- Earliest claimed: 1979-07-03
- Assignees: Egyt Gyogyszervegyeszeti Gyar
- Inventors: Zoltan Budai; Aranka Lay nee Konya; Tibor Mezei; Lujza Petocz; Katalin Grasser; Ibolya Kosoczky; Eniko Szirt nee Kiszelly; Peter Gorog
- Web page: https://patentgrep.com/patent/US4395413A

## CPC

- C07D 295/088: to an acyclic saturated chain
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to novel oxime ethers of the general formula /I/ and acid addition salts and quaternary ammonium derivatives thereof, ##STR1## wherein A represents a C.sub.2-6 straight or branched alkylene chain, R and R.sup.1 each represent a C.sub.1-6 alkyl group or they form together with the adjacent nitrogen atom a heterocyclic ring containing 4 to 7 carbon atoms and optionally a further hetero atom, i.e. an oxygen, sulfur or nitrogen atom, and said ring may be optionally substituted by a C.sub.1-3 alkyl, phenyl or benzyl group, R.sup.2 and R.sup.3 each denote a hydrogen atom or together form a valency bond, R.sup.4 denotes a C.sub.1-10 alkyl or C.sub.2-10 alkenyl group, and n denotes an integer from 3 to 7. The compounds of the general formula /I/ are prepared according to the invention by reacting a cycloalkane derivative of the general formula /II/ ##STR2## wherein R.sup.2, R.sup.3, R.sup.4 and n have the same meaning as above, whereas Y denotes an oxygen or sulphur atom or a .dbd.N--OH group with an aminoalkyl derivative of the general formula /III/ ##STR3## wherein R, R.sup.1 and A have the same meaning as stated above and Z means a halogen atom or a H.sub.2 N--O-- group or a salt thereof in the presence of a basic condensing agent. The new compounds of the general formula /I/ possess valuable nicotine-lethality inhibiting, local anaesthetic, analgesic effects, which are, in case of certain compounds, complemented by anti-hypertensive, maximum electroshock and tetracorspasm inhibiting, ulcus inhibiting and motility inhibiting effects, and can be applied to advantage in the therapy.

## Claims

### Claim 1

An oxime ether of the general formula /I/ or a pharmaceutically acceptable acid addition salt thereof, ##STR9## wherein A represents a C.sub.2-6 straight or branched alkylene chain, R
and R.sup.1 each represent a C.sub.1-6 alkyl group or they form together with the adjacent nitrogen atom a piperazinyl group optionally substituted with a C.sub.1-3 alkyl or benzyl group,
R.sup.2 and R.sup.3 each denote a hydrogen atom or together form a valency bond,
R.sup.4 denotes a C.sub.1-10 alkyl or C.sub.2-10 alkenyl group, and n is 4 or 5.

### Claim 2 (depends on 1)

A compound as claimed in claim 1, wherein R.sup.4 denotes ethyl, n-propyl, n-butyl, n-pentyl, n-heptyl or vinyl group.

### Claim 3 (depends on 1, 2)

A compound as claimed in claim 1 or 2, wherein A represents ethylene, propylene or isobutylene group.

### Claim 4 (depends on 1)

A compound as claimed in claim 1, wherein R and R.sup.1 each represent methyl or ethyl group, or they form, together with the adjacent nitrogen atom, an N-benzylpiperazinyl, N-methylpiperazinyl or piperazinyl ring.

### Claim 5 (depends on 1)

A compound as claimed in claim 1, wherein n is 4.

### Claim 6

2-n-Butyl-1-/2'-dimethylaminoethoxyimino/-cyclohexane, 2-n-butyl-1-/3'-dimethylaminopropoxyimino/-cyclohexane, 2-n-butyl-1-/2'-methyl-3'-dimethylaminopropoxyimino/-cyclohexane, 2-n-butyl-1-[3'-/4"-benzylpiperazinyl/-propoxyimino]-cyclohexane, 2-n-butylidene-1-[3'-/4"-methylpiperazinyl/-propoxyimino]-cyclohexane, 2-n-butylidene-[3'-/4"-benzylpiperazinyl/-propoxyimino]-cyclohexane, 2-n-pentylidene-1-[3'-/4"-methylpiperazinyl/-propoxyimino]-cyclohexane, 2-n-pentylidene-1-[3'-/4"-benzylpiperazinyl/-propoxyimino]-cyclohexane, 2-allyl-[3'-/4"-methylpiperazinyl/-propoxyimino]-cyclohexane, 2-n-hexylidene-1-[3'-/4"-methylpiperazinyl/-propoxyimino]-cyclohexane, 2-n-octylidene-1-[3'-/4"-methylpiperazinyl/-propoxyimino]-cyclohexane, or a pharmaceutically acceptable acid addition salt thereof.

### Claim 7 (depends on 1)

A nicotine lethality-inhibiting pharmaceutical composition containing as active ingredient a nicotine lethality-inhibiting effective amount of a compound as claimed in claim 1, together with a pharmaceutical excipient.