# US 8,785,425 B2 · 11β-hydroxyandrosta-4-ene-3-ones

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- Number: US 8,785,425 B2
- Document ID: US8785425B2
- Status: Granted
- Kind: B2
- Application number: 12/180,257
- Filed: 2008-07-25
- Published: 2009-02-26
- Granted: 2014-07-22
- Earliest claimed: 2006-01-27
- Assignees: Sun Pharma Advanced Research Company Ltd.
- Applicants: Jiten Ranchhodbhai Patel; Gopalkumar Chimanlal Patel; Gaurav Sanjivkumar Sheth; Samir Rameshchandra Shah; Sanjay Nandlal Mandhane; Trinadha Rao Chitturi; Rajamannar Thennati
- Inventors: Jiten Ranchhodbhai Patel; Gopalkumar Chimanlal Patel; Gaurav Sanjivkumar Sheth; Samir Rameshchandra Shah; Sanjay Nandlal Mandhane; Trinadha Rao Chitturi; Rajamannar Thennati
- Web page: https://patentgrep.com/patent/US8785425B2

## CPC

- C07J 31/006: {not covered by C07J31/003}
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/30: Oestrogens
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/04: Antipruritics
- A61P 17/06: Antipsoriatics
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 27/02: Ophthalmic agents
- A61P 27/16: Otologicals
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- C07J 3/005: {the carbon atom being part of a carboxylic function}
- C07J 17/00: Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton (cardanolide, bufanolide C07J19/00)
- C07J 41/0038: {with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group}
- C07J 71/0015: {at position 9(11)}
- C07J: STEROIDS (seco-steroids C07C)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention provides 11β-hydroxyandrosta-4-ene-3-one compounds of Formula I, or physiologically acceptable salts or solvates thereof: wherein R4 represents a moiety selected from a group consisting of (A), (B) and (C), with a proviso that when R4 represents moiety (C), Z is S:

## Claims

### Claim 1

An 11β-hydroxyandrosta-4-ene-3-one compound of formula I, or a physiologically acceptable salt thereof:
wherein
represents double bond and represents α or β-configuration;
Z represents O or S;
R1 represents hydrogen or methyl which may be either in α or β-configuration;
R2 and R3 are the same or different and each independently represents hydrogen, halogen, or methyl;
R5 is independently selected from the group consisting of (C1-C4)-alkyl, (C3-C6)-cycloalkyl, —O—(C1-C4)-alkyl, and a phenyl ring or heterocyclic ring selected from the group consisting of thienyl and furyl, wherein the ring or ring system is unsubstituted or substituted by one or more of halogen, —OH, and (C1-C3)-alkyl, wherein the alkyl or cycloalkyl groups are optionally substituted by one or more of halogen, (C1-C3)-alkyl, —O—(C1-C3)-alkyl, and (C3-C6)-cycloalkyl;
R4 represents moiety:
wherein
m1 is 1;
m2 is 0 or 1;
m3 is 0 or 1;
n1 is 0, 1 or 2;
P and Q are hydrogen;
X represents either a double bond or a triple bond;
J and K are independently selected from the group consisting of hydrogen and (C1-C3)-alkyl; and
L is selected from the group consisting of halogen, —OH, —O—(C1-C4)-alkyl, —OCO—(C1-C6)-alkyl, —OCO—(C3-C13)-cycloalkyl, —OCO—CO—O—(C1-C4)-alkyl, —OCO—O—(C1-C10)-alkyl, —OCO—O—(C3-C6)-cycloalkyl, —OCO—NH—(C1-C4)-alkyl, —OCO—N—[(C1-C4)-alkyl]2, and —N—[(C1-C8)-alkyl]2; wherein
the alkyl or cycloalkyl groups of J, K or L are optionally substituted by one or more of halogen, —OH, (C1-C3)-alkyl, —O—(C1-C3)-alkyl, —OCO—(C1-C3)-alkyl, —COOH, —COO—(C1-C5)-alkyl, —COO—(C1-C5)-haloalkyl, —NHCO—(C1-C8)-alkyl, —ONO2, and (C3-C6)-cycloalkyl;
J and K are optionally joined together with the carbon atom to which they are attached to represent a (C3-C6)-cycloalkyl or —CO— group and L is selected from hydroxyl and O(C1-C3)alkyl; and
J, K and L are absent when n1 is 0.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R1 is methyl; R2 is hydrogen, fluoro, or chloro; and R3 is hydrogen or fluoro.

### Claim 3 (depends on 1)

The compound of claim 1 wherein R5 is (C1-C4)-alkyl, (C3-C6)-cycloalkyl, —O—(C1-C4)-alkyl, a phenyl ring, a furyl ring, or a thienyl ring, wherein the ring is unsubstituted or substituted by one or more of halogen, (C1-C3)-alkyl, and —O—(C1-C3)-alkyl; wherein the alkyl or cycloalkyl groups are optionally substituted by halogen, —OH, (C1-C3)-alkyl, —O—(C1-C3)-alkyl, (C3-C6)-cycloalkyl, or a combination thereof.

### Claim 4 (depends on 1)

The compound of claim 1 wherein R5 is methyl, ethyl, propyl, isopropyl, n-butyl, dichloromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, 2-furyl, 3-furyl, 3-methyl-2-furyl, 2-thienyl, or 5-chloro-2-thienyl.

### Claim 5

An 11β-hydroxyandrosta-4-ene-3-one compound of formula I-B, or a physiologically acceptable salt thereof:
wherein
represents double bond and represents α or β-configuration;
Z represents O or S;
R1 represents hydrogen or methyl which may be either in α or β-configuration;
R2 and R3 are the same or different and each independently represents hydrogen, halogen, or a methyl group;
R5 is independently selected from the group consisting of (C1-C4)-alkyl, (C3-C6)-cycloalkyl, —O—(C1-C4)-alkyl, and a phenyl ring or heterocyclic ring selected from the group consisting of thienyl and furl, wherein the ring or ring system is unsubstituted or substituted by one or more of halogen, —OH, and (C1-C3)-alkyl, wherein the alkyl or cycloalkyl groups are optionally substituted by one or more of halogen, (C1-C3)-alkyl, —O—(C1-C3)-alkyl, and (C3-C6)-cycloalkyl;
m1 is 1;
m2 is 0 or 1;
m3 is 0 or 1;
n1 is 0, 1 or 2;
P and Q are hydrogen;
X represents either a double bond or a triple bond;
J and K are independently selected from the group consisting of hydrogen and methyl; and
L is selected from the group consisting of halogen, —OH, —O—(C1-C4)-alkyl, —OCO—(C1-C6)-alkyl, —OCO—(C3-C13)-cycloalkyl, —OCO—CO—O—(C1-C4)-alkyl, —OCO—O—(C1-C10)-alkyl, —OCO—O—(C3-C6)-cycloalkyl, —OCO—NH—(C1-C4)-alkyl, —OCO—N—[(C1-C4)-alkyl]2, and —N—[(C1-C8)-alkyl]2; wherein
the alkyl or cycloalkyl groups of J, K or L are optionally substituted by one or more of halogen, —OH, (C1-C3)-alkyl, —O—(C1-C3)-alkyl, —OCO—(C1-C3)-alkyl, —COOH, —COO—(C1-C5)-alkyl, —COO—(C1-C5)-haloalkyl, —NHCO—(C1-C8)-alkyl, —ONO2, and (C3-C6)-cycloalkyl;
J and K are optionally joined together with the carbon atom to which they are attached to represent a (C3-C6)-cycloalkyl or —CO— group and L is selected from hydroxyl and methoxy; and
J, K and L are absent when n1 is 0.

### Claim 6 (depends on 5)

The compound of claim 5, wherein Z represents S.

### Claim 7 (depends on 1)

The 11β-Hydroxyandrosta-4-ene-3-one as claimed in claim 1 selected from the group consisting of
S-(4-Hydroxy-but-2-ynyl) 6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-(4-n-Propylcarbonyloxy-but-2-ynyl) 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Ethoxy-1,2-dioxoethyl-(E)-but-2-enyl]6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Ethoxy-1,2-dioxoethyl)oxy-(E)-but-2-enyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-n-Propylcarbonyloxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Methylpropionyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2,2-Dimethylpropionyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2,2-Dimethylpropionyloxy)-but-2-ynyl]6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate,
S-[4-n-Propylcarbonyloxy-(Z)-but-2-enyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Ethoxy-1,2-dioxoethyl)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-n-Propylcarbonyloxy-but-2-ynyl]6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-[(2-thienylcarbonyl)oxy]androsta-1,4-diene-17β-carbothioate,
S-[(4-Cyclopropylcarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[(4-Cyclobutylcarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[(4-Cyclopentylcarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-n-Propylcarbonyloxy-(E)-but-2-enyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[(4-Methoxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[(4-Ethoxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2,2-Dimethylethyloxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Methylpropyloxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(3-Chloropropylcarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)-oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-Dichloroacetoxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Methylpropylcarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)-oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(3,3-Dimethylpropylcarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-(4-Propionyloxy-but-2-ynyl) 6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(3,3,3-Trifluoropropionyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)-oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(Methoxyacetyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(Ethoxyacetyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-(4-Acetoxy-but-2-ynyl) 6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2,2-Dimethylbutylcarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)-oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-((1S)-Camphanylcarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)-oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Ethoxybutyl-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)-oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Ethyloxy-(Z)-but-2-en-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Methoxybutyl-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)-oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Isopropyloxybutyl-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-[(2-furanylcarbonyl)oxy]-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Isobutyloxybutyl-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-n-Butyloxybutyl-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(3-Chloro-2,2-dimethylpropionyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Methoxy-(E)-but-2-en-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(3-Methyl-1-oxobutyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Ethyl-1-oxobutyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(N,N-Dimethylaminocarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Chloro-2-methylpropionyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Methyl-1-oxopentyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Hydroxy-2-methylpropionyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2-Fluoro-2-methylpropionyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Methoxy-(Z)-but-2-en-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Ethoxy-(E)-but-2-en-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(4-Isobutyloxy-(E)-but-2-en-1,4-dione)oxy-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-(4-Acryloyloxy-but-2-ynyl) 6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(Cyclopentylmethyloxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(3-Methylbut-2-enoxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(n-Pentyloxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(2,2-Dimethyl-3-fluoropropionyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanyl-carbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-((S)-2,2-Dimethyl-1,3-dioxolan-4-yl-methoxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(R)-2,2-Dimethyl-1,3-dioxolan-4-yl-methoxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-[4-(Isoamyloxycarbonyloxy)-but-2-ynyl]6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate,
S-(4-Ethoxy-but-2-ynyl)6α,9α-difluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate.

### Claim 8 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable diluent or carrier.

### Claim 9 (depends on 1)

A method of inhibiting a glucocorticoid receptor comprising contacting the receptor with an effective inhibitory amount of a compound of claim 1.

### Claim 10 (depends on 9)

The method of claim 9 wherein the contacting is in vitro.

### Claim 11 (depends on 9)

The method of claim 9 wherein the contacting is in vivo.

### Claim 12 (depends on 8)

A method of treating inflammation comprising administering to a mammal in need of such treatment an effective anti-inflammatory amount of a composition of claim 8.

### Claim 13 (depends on 12)

The method of claim 12 wherein the treatment comprises topical or parenteral administration of the composition.

### Claim 14 (depends on 12)

The method of claim 12 wherein the administering causes insignificant or no adverse systemic effects.