Steroidal anaesthetics of the pregnane and 19-norpregnane series

Claim 2

A steroid compound of the formula ##SPC1## or a pharmaceutically acceptable salt thereof wherein R 1 is --H or --CH 3 ; R 2 is H, C 1 -C 6 alkyl or a halogen atom; R 3 is H, acyloxy or acylthio of 1-9 C atoms, an ether or thioether group of 1-9 C atoms, an alkyl or cycloalkyl group of up to 9 C atoms, phenyl, benzyl, hydroxy, thiocyanato, nitrooxy, a halogen atom, azido, amino, monoalkylamino, dialkylamino or morpholino; R 4 is H or C 1 -C 6 alkyl; R 5 and R 6 are each H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or a halogen atom, only one of R 5 and R 6 being a halogen atom; R 7 is cyano, azido or substituted or unsubstituted morpholino, thiamorpholino, pyrrolino, pyrrolidino, piperidino or thiazolidino; and X is oxo, an epoxy group linked also to the 9-position or a grouping ##EQU1##wherein R 8 is H, hydroxy or alkyl or alkenyl of up to 6 C atoms and R 9 is H or hydroxy, only one of R 8 and R 9 being hydroxy, the lines -- -- -- indicating the presence of a single or double bond at the Δ 1 , Δ 4 and Δ 8 (9) positions.

Claim 3

A steroid as claimed in claim 1 which possesses a 5α-hydrogen atom.

Claim 4

A steroid as claimed in claim 1 which possesses an 11-oxo group.

Claim 5

A steroid as claimed in claim 1 which possesses at least one of a 16α-methyl group, a double bond at the Δ 1 or Δ 4 position and a 2β-alkyl or alkoxy group.

Claim 6

A steroid as claimed in claim 1 wherein R 7 is a morpholino or thiamorpholino group.

Claim 7

A steroid as claimed in claim 1 wherein R 7 is morpholino, thiamorpholino, pyrrolino, pyrrolidino, piperidino or thiazolidino substituted by at least one alkyl substituent.

Claim 8

A steroid as claimed in claim 1 wherein R 7 is a thiazolidino group.

Claim 9

A steroid as claimed in claim 1 which possesses a basic nitrogen atom and is in the form of its hydrochloride, hydrobromide, phosphate, sulphate, p-toluenesulphonate, methanesulphonate, citrate, tartrate, acetate, ascorbate, lactate, maleate or succinate.

Claim 10

A steroid as claimed in claim 1 which possesses a 21-cyano group and is in the form of a salt with a base.

Claim 11

The steroid of claim 1 which is 21-cyano-3α-hydroxy-5α-pregnane-11,20-dione or its sodium salt; 21-cyano-2β-ethoxy-3α-hydroxy-5α-pregnane-11,20-dione or its sodium salt; 21-cyano-2β-methoxy-3α-hydroxy-5α-pregnane-11,20-dione; 21-cyano-2β-isopropoxy-3α-hydroxy-5α-pregnane-11,20-dione; 21-cyano-3α-hydroxy-16α-methyl-5α-pregnane-11,20-dione; 3α-hydroxy-21-morpholino-5α-pregnane-11,20-dione or its citrate, mesylate or hydrochloride; 2β-ethoxy-3α-hydroxy-21-morpholino-5α-pregnane-11,20-dione or its citrate, phosphate, acetate or ascorbate; 3α-hydroxy-16α-methyl-21-morpholino-5α-pregnane-11,20-dione; 3α-hydroxy-21-(2'-methylmorpholino)-5α-pregnane-11,20-dione; 3α-hydroxy-21-(cis-2',6'-dimethylmorpholino)-5α-pregnane-11,20-dione; 3α-hydroxy-21-thiamorpholino-19-nor-5α-pregnane-11,20-dione or its citrate; 21-azido-3α-hydroxy-5α-pregnane-11,20-dione; 21-azido-2β-ethoxy-3α-hydroxy-5α-pregnane-11,20-dione; 21-azido-3α-hydroxy-5β-pregnane-11,20-dione; 21-azido-3α-hydroxy-5α-pregnan -20-one; 21-azido-3α-hydroxy-16α-methyl-5α-pregnane-11,20-dione; 21-azido-3α-hydroxy-2β-methoxy-5α-pregnan -20-one; 21-azido-3α-hydroxy-19-nor-5α-pregnane-11,20-dione; or 21-azido-3α-hydroxy-5α-pregn-1-ene-11,20-dione.

Claim 12

The steroid of claim 1 which is 21-cyano-3α-hydroxy-2β-methyl-5α-pregnane-11,20-dione; 3α-hydroxy-21-thiazolidino-5α-pregnane-11,20-dione; or 21-azido-3α-hydroxy-2β-methyl-5α-pregnane-11,20-dione.

Claim 13

A steroid as claimed in claim 1 wherein R 7 is a morpholino group.

Claim 14

The steroid of claim 1 which is 21-cyano-3α-hydroxy-5α-pregnane-11,30-dione or the sodium salt thereof.

Claim 15

The steroid of claim 1 which is 21-cyano-2β-ethoxy-3α-hydroxy-5α-pregnane-11,20-dione or the sodium salt thereof.

Claim 16

The steroid of claim 1 which is 21-cyano-2β-methoxy-3α-hydroxy-5α-pregnane-11,20-dione.

Claim 17

The steroid of claim 1 which is 3α-hydroxy-21-morpholino-5α-pregnane-11,20-dione or the citrate, mesylate or hydrochloride salt thereof.

Claim 18

The steroid of claim 1 which is 2β-ethoxy-3α-hydroxy-21-morpholino-5α-pregnane-11,20-dione or the citrate, phosphate, acetate or ascorbate salt thereof.

Claim 19

The steroid of claim 1 which is 3α-hydroxy-16α-methyl-21-morpholino-5α-pregnane-11,20-dione.

Claim 20

The steroid of claim 1 which is 3α-hydroxy-21-(cis-2',6'-dimethylmorpholino)-5α-pregnane-11,20-dione.

Claim 21

The steroid of claim 1 which is 3α-hydroxy-21-thiamorpholino-19-nor-5α-pregnane-11,20-dione or the citrate salt thereof.

Claim 22

The steroid of claim 1 which is 21-azido-3α-hydroxy-5α-pregnane-11,20-dione.

Claim 23

The steroid of claim 1 which is 21-azido-2β-ethoxy-3α-hydroxy-5α-pregnane-11,20-dione.

Claim 24

The steroid of claim 1 which is 21-azido-3α-hydroxy-5α-pregnan-20-one.

Claim 25

The steroid of claim 1 which is 21-azido-3α-hydroxy-2β-methoxy-5α-pregnan-20-one.

Claim 26

The steroid of claim 1 which is 21-azido-3α-hydroxy-5α-pregn-1-ene-11,20-dione.

Claim 27

The steroid of claim 1 which is 3α-hydroxy-21-thiazolidino-5α-pregnane-11,20-dione.

Claim 28

A steroid compound of the formula ##SPC2## or a pharmaceutically acceptable salt thereof wherein R 1 is --H or --CH 3 ; R 4 is --H or --CH 3 ; R 5 is two hydrogen atoms or a hydrogen atom and methyl in the α- or β-configuration or gem-dimethyl; R 7 is cyano, azido, morpholino, thiamorpholino; pyrrolino, pyrrolidino, peperidino or thiazolidino; and X is two hydrogen atoms or oxo.

Claim 29

A steroid compound of the formula ##SPC2## or a pharmaceutically acceptable salt thereof wherein R 1 is --H or --CH 3 ; R 4 is --H or --CH 3 ; R 5 is two hydrogen atoms or a hydrogen atom and methyl in the α- or β-configuration or gem-dimethyl; R 7 is cyano, azido, morpholino, thiamorpholino; pyrrolino, pyrrolidino, peperidino or thiazolidino; and X is two hydrogen atoms or oxo.

Claim 30

A steroid compound of the formula ##SPC3## or a pharmaceutically acceptable salt thereof wherein R 1 is --H or --CH 3 ; R 2 is --H or --CH 3 ; R 3 is --H, C 1-5 alkyl, C 1-6 alkoxy, C 2-6 alkanoyloxy, a halogen atom or thiocyanato, R 2 being --CH 3 only when R 3 is H; R 4 is --H or --CH 3 ; R 5 is two hydrogen atoms or a hydrogen atom and methyl in the α- or β-configuration or gem-dimethyl; R 7 is cyano, azido, morpholino, thiamorpholino; pyrrolino, pyrrolidino, peperidino or thiazolidino; and X is two hydrogen atoms or oxo.

Claim 31

A steroid compound of the formula ##SPC3## or a pharmaceutically acceptable salt thereof wherein R 1 is --H or --CH 3 ; R 2 is --H or --CH 3 ; R 3 is --H, C 1-5 alkyl, C 1-6 alkoxy, C 2-6 alkanoyloxy, a halogen atom or thiocyanato, R 2 being --CH 3 only when R 3 is H; R 4 is --H or --CH 3 ; R 5 is two hydrogen atoms or a hydrogen atom and methyl in the α- or β-configuration or gem-dimethyl; R 7 is cyano, azido, morpholino, thiamorpholino; pyrrolino, pyrrolidino, peperidino or thiazolidino; and X is two hydrogen atoms or oxo.