# US 4,396,777 A · 1-Cycloalkyl phosphonium salts

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- Number: US 4,396,777 A
- Document ID: US4396777A
- Status: Granted
- Kind: A
- Application number: 06/362,733
- Filed: 1982-03-29
- Granted: 1983-08-02
- Earliest claimed: 1980-08-06
- Assignees: G. D. Searle & Co.
- Inventors: Richard A. Mueller
- Web page: https://patentgrep.com/patent/US4396777A

## CPC

- A01N 57/34: having phosphorus-to-halogen bonds; Phosphonium salts
- C07F 9/5435: {Cycloaliphatic phosphonium compounds}
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

1-Cycloalkyl phosphonium salts represented by the formula ##STR1## wherein: R is selected from the group consisting of lower alkyl, hydroxy lower alkyl, halo lower alkyl, amino lower alkyl, cyano lower alkyl, lower alkenyl with the limitation that the double bond is not on the carbon atom attached to the oxygen atom, benzyl, substituted benzyl and ##STR2## wherein q is O or 1 and R.sub.4 is selected from the group consisting of hydroxy, loweralkoxy, phenyl, substituted phenyl, and ##STR3## wherein R.sub.5 and R.sub.6 are the same or different members of the group consisting of hydrogen and loweralkyl or taken together form a 5 or 6 membered ring; m is 1, 2 or 3; n is 0 or 1; o is 0 or 1; p is 0 or 1; R.sub.1, R.sub.2 and R.sub.3 are the same or different members of the group consisting of hydrogen, lower alkyl, lower alkoxy and halo; and X is a pharmaceutically acceptable anion. The compounds are useful as analgesic agents.

## Claims

### Claim 1

A process for preparing a 2-ketocyclohexylidenetriphenyl phosphonium salt which comprises heating a [(tetrahydro-2H-pyran-2-ylidene)methyl]triphenyl phosphonium salt in a suitable solvent at a temperature of between 110.degree.-180.degree. C. for from 24-84 hours.

### Claim 2 (depends on 1)

The process of claim 1 wherein said solvent is xylene.

### Claim 3 (depends on 1)

The process of claim 1 wherein said temperature is from about 135.degree. to about 150.degree. C.