JPH06293793A - Production of steroid-17-amide compounds - Google Patents

Abstract

PURPOSE:To profitably obtain the subject compound having a 5alpha-reductase- inhibiting action by a simple operation comprising reacting a specific carboxylic acid compound with a specified amine compound in the presence of a sulfonyl compound. CONSTITUTION:A carboxylic acid compound of formula I [A is group of formula II or III (R<3> is H, lower alkyl; R<4> is H, protected OH, substituted OH, protected carboxy, cyano; the dotted line is single bond or double bond), etc.,] s reacted with an amino compound of formula: NHR R [R,R are H, (substututed) lower alkyl, alkenyl, cycloalkyl] in the presence of a sulfonyl compound such a up mula: R'S0.X (R' is lover alkyl, halogenoalkyl, camphanyl, etc.; X is halogen) to produce the objective compound of formula TV.

Description

Detailed Description of the Invention

[0001]

[Object of the Invention]

[0002]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing steroid-17-amides useful as a medicine itself (for example, a prophylactic / therapeutic agent for benign prostatic hyperplasia) or an intermediate thereof.

[0003]

2. Description of the Related Art Steroid compounds useful as pharmaceuticals, for example, azasteroid compounds having a testosterone 5α-reductase inhibitory action and useful as a therapeutic drug for benign prostatic hyperplasia, have a carbamoyl group which may be substituted at the 17-position thereof. As a conventional method for producing a 17-position-substituted carbamoyl group, for example, a method via an acid halide (JP-A-54-145669) and a method via an active ester (JP-A-2-172999). Japanese Patent Laid-Open No. 4-2
88096).

[0004]

However, these methods are not always sufficiently satisfactory in terms of operability of reaction, yield, necessity of purification by chromatography, and the like. Development of efficient and simple manufacturing methods is desired. The present inventors have conducted extensive studies for many years on a production method of introducing a substituted carbamoyl group into the 17-position of a steroid compound, and as a result, by reacting a carboxylic acid compound and an amine compound in the presence of a sulfonyl compound, The present invention has been completed by finding an amidation reaction that yields an amide compound with good yield and is simple.

[0005]

[Means for Solving the Problems]

[0006]

DETAILED DESCRIPTION OF THE INVENTION General formula (II) of the present invention

[0007]

[Chemical 10]

[Wherein R ¹ and R ² are the same or different and each is a hydrogen atom, a lower alkyl group or a substituted lower alkyl group (the substituent is selected from the substituent group A and the substituent group B. Represents an aryl group which may be substituted with a group, a heteroaryl group which may be substituted with a group selected from Substituent group A, or a cycloalkyl group which may be substituted with a group selected from Substituent group A. .), An alkenyl group or a cycloalkyl group, and A is the following general formula (I-1),
Group having (I-2) or (I-3)

[0009]

[Chemical 11]

(In the above formula, R ³ represents a hydrogen atom or a lower alkyl group, R ⁴ represents a hydrogen atom, a protected hydroxyl group, a substituted hydroxyl group, a protected carboxy group or a cyano group, and R 4 ⁵ represents a hydrogen atom or an amino group,
A bond including a dotted line indicates a single bond or a double bond. ) Is shown. ] The production of steroid-17-amides having
General formula (I)

[0011]

[Chemical 12]

A carboxylic acid compound having the general formula R ⁶ SO ₂ X (IVa) or (R ⁶ SO ₂ ) ₂ O (IVb) (wherein A has the same meaning as described above) Wherein R ⁶ represents a lower alkyl group, a halogenoalkyl group, a camfanyl group, an isocyano group, or an aryl group which may be substituted with a group selected from Substituent group A, and X 6
Represents a halogen atom. In the presence of a sulfonyl compound having the general formula NHR ¹ R ² (III) (wherein R ¹ and R ² have the same meanings as described above). Further, the carboxylic acid compound having the general formula (I) is treated with an amine having the general formula (III) in an inert solvent in the presence of a base and a sulfonyl compound having the general formula (IVa) or (IVb). A compound is reacted, preferably, the carboxylic acid compound having the general formula (I) is prepared by reacting the carboxylic acid compound having the general formula (I) in the presence of a base and a sulfonyl compound having the general formula (IVa). It is characterized in that an amine compound having (III) is reacted, and more preferably in the above-mentioned method for producing steroid-17-amides,

(1) A method for producing a steroid-17-amide, wherein R ⁶ is an aryl group which may be substituted with a halogenoalkyl group or a group selected from Substituent group A,
(2) R ¹ and R ² are the same or different and are a hydrogen atom,
A lower alkyl group or a substituted lower alkyl group (the substituent represents an aryl group which may be substituted with a group selected from the substituent group A and the substituent group B or an unsubstituted heteroaryl group). A method for producing a steroid-17-amide, (3) R ¹ and R ² are the same or different,
A hydrogen atom, a lower alkyl group or a substituted lower alkyl group (the substituent represents an aryl group which may be substituted with a group selected from the substituent group A or an unsubstituted heteroaryl group), (4) R ¹ is a hydrogen atom and R ² is a lower alkyl group or a substituted lower alkyl group (the substituent is a group selected from Substituent group A). (5) R ² which represents an aryl group which may be substituted with or an unsubstituted heteroaryl group, which is (5) R ²
Is an isopropyl group, an isobutyl group, a t-butyl group or a substituted C ₁ -C ₃ alkyl group [the substituent is a phenyl group, a substituted phenyl group (the substituent is methyl, methoxy, ethoxy, fluoro Or chloro), a furyl group or a thienyl group. ], The steroid-
A method for producing a 17-amide, (6) R ² is a t-butyl group,
Group [wherein having the formula _{-C (CH 3) (CH 3} ) -R 2 a, R 2 a is substituted phenyl group (the substituent is methyl, methoxy, ethoxy, fluoro or chloro ), A furyl group or a thienyl group. Or a C ₁ -C ₃ alkyl group substituted with 2 to 3 substituents [wherein the substituent is an optionally substituted phenyl group (wherein the substituent is methyl, methoxy, ethoxy, fluoro or chloro]] .), A furyl group or a thienyl group. ], The steroid-17
-Method for producing amides, (7) R ² is t-butyl group, formula-
_{C (CH 3) (CH 3} ) group [wherein with -R ² _a, R ² _a is substituted phenyl group (the substituent is methyl, methoxy, ethoxy, fluoro or chloro. ) Or a thienyl group. ], The phenyl ring is a diphenylmethyl, 1,2-diphenylethyl or 1,1-diphenylethyl group optionally substituted with methyl, methoxy, ethoxy, chloro or fluoro, steroid-17
A method for producing amides, (8) A is general formula (I-1), a method for producing steroid-17-amides, (9) A is general formula (I-1), and R ³ is A method for producing a steroid-17-amide having a hydrogen atom, a methyl group or an ethyl group, (10) A has the general formula (I-1), and R ³ has a hydrogen atom or a methyl group, the steroid-17 A method for producing an amide, (11) A is the general formula (I-1),
A method for producing a steroid-17-amide, wherein the bond at the 6-position is a single bond, (12) A is a general formula (I-2), a method for producing a steroid-17-amide, (13) A is A steroid represented by the general formula (I-2), wherein R ⁴ is a protected hydroxyl group, a protected carboxy group or a cyano group;
Method for producing 17-amides, (14) A is represented by the general formula (I-
2), wherein the bond containing a dotted line is a double bond, a method for producing a steroid-17-amide, (15) A is a general formula (I-3), a method for producing a steroid-17-amide , (16) A is the general formula (I-3), and R ⁵ is a hydrogen atom. A method for producing a steroid-17-amide (17) A is the general formula (I-3), and the dotted line Method for producing steroid-17-amides in which bond containing is double bond [Substituent group A] Lower alkyl group, lower alkoxy group and halogen atom [Substituent group B] Hydroxyl group, lower alkoxycarbonyl group and di-lower alkyl Amino group.

"Lower alkyl group" in the definition of R ¹ , R ² , R ³ , R ⁶ and [Substituent group A] and "substituted lower alkyl group" in the definition of R ¹ and R ² "Lower alkyl group" means, for example, methyl, ethyl, n
-Propyl, isopropyl, n-butyl, isobutyl,
s-Butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, n-hexyl, isohexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl Carbon such as, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl It represents a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, preferably 1 carbon atom
To 4 linear or branched alkyl groups, more preferably, R ¹ and R ² are linear or branched alkyl groups having 1 to 3 carbon atoms, and other are: It is a methyl or ethyl group.

The "halogenoalkyl group" in the definition of R ⁶ is a group in which the following "halogen atom" is bonded to the above "lower alkyl group", for example, trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl. , Dibromomethyl, fluoromethyl, 2,2,2-
Trichloroethyl, 2,2,2-trifluoroethyl,
1 to 2 carbon atoms such as 2-bromoethyl, 2-chloroethyl, 2-fluoroethyl and 2,2-dibromoethyl
A group in which a "halogen atom" is bonded to a straight chain alkyl group can be mentioned, and preferably 2-bromoethyl, 2-
Chloroethyl and 2-fluoroethyl.

In the definition of R ¹ and R ² , "substituent group A
And an “aryl group” of “an aryl group which may be substituted with a group selected from the substituent group B”, and an aryl group which may be substituted with a group selected from the substituent group A in the definition of R ^6. The “aryl group” of “” is an aromatic hydrocarbon group having 6 to 10 carbon atoms, for example, a phenyl group or a naphthyl group, and preferably a phenyl group.

The "halogen atom" in the definition of X and [Substituent group A] is, for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and preferably X is a chlorine atom or a bromine atom. Alternatively, it is an iodine atom (particularly preferably a chlorine atom), and the others are a fluorine atom, a chlorine atom or a bromine atom (particularly preferably a fluorine atom or a chlorine atom).

In the definition of R ¹ and R ² , "substituent group A
The "heteroaryl group" of the "heteroaryl group optionally substituted with a group selected from the following" represents a 5- to 6-membered cyclic heteroaryl group having 1 to 3 nitrogen atoms, oxygen atoms or sulfur atoms, For example, furyl, thienyl, pyridyl, pyrrolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazinyl, pyrimidyl, pyridazinyl group, preferably furyl, thienyl or pyridyl group, more preferably,
It is a furyl or thienyl group, particularly preferably a thienyl group.

The "cycloalkyl group" in the definition of R ¹ and R ² and the "cycloalkyl group" of the "cycloalkyl group which may be substituted with a group selected from the substituent group A" means cyclopropyl and cyclobutyl. , Cyclopentyl,
Shows an optionally condensed 3- to 10-membered saturated cyclic hydrocarbon group such as cyclohexyl, cycloheptyl, norbornyl, and adamantyl, preferably a 3- to 6-membered saturated cyclic hydrocarbon group, and more preferably A cyclopentyl or cyclohexyl group.

The term "alkenyl group" in the definition of R ¹ and R ² means ethenyl, 1-propenyl, 2-propenyl, 1-methyl-2-propenyl, 1-methyl-1-propenyl, 2-methyl-1-. Propenyl, 2-methyl-
2-propenyl, 2-ethyl-2-propenyl, 1-butenyl, 2-butenyl, 1-methyl-2-butenyl, 1
-Methyl-1-butenyl, 3-methyl-2-butenyl,
1-ethyl-2-butenyl, 3-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 1-ethyl-3-butenyl, 1-pentenyl, 2-pentenyl,
1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-pentenyl, 1-methyl-3-pentenyl,
2-methyl-3-pentenyl, 4-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,
1-hexenyl, 2-hexenyl, 3-hexenyl, 4
-C2 to C6 such as hexenyl and 5-hexenyl
Can be mentioned straight chain or branched alkenyl groups,
It is preferably a linear or branched alkenyl group having 3 to 4 carbon atoms, and particularly preferably a 2-propenyl group.

"Protected hydroxyl group" in the definition of R ⁴
"Protecting group" means hydrogenolysis, hydrolysis, electrolysis,
A "protecting group in the reaction" which can be cleaved by a chemical method such as photolysis is shown, and preferably formyl, acetyl,
Propionyl, butyryl, isobutyryl, pentanoyl, pivaloyl, valeryl, isovaleryl, octanoyl, nonanoyl, decanoyl, 3-methylnonanoyl,
8-methylnonanoyl, 3-ethyloctanoyl, 3,
7-dimethyloctanoyl, undecanoyl, dodecanoyl, tridecanoyl, tetradecanoyl, pentadecanoyl, hexadecanoyl, 1-methylpentadecanoyl, 14-methylpentadecanoyl, 13,13-dimethyltetradecanoyl, heptadecanoyl, 15 An alkylcarbonyl group such as methylhexadecanoyl, octadecanoyl, 1-methylheptadecanoyl, nonadecanoyl, aicosanoyl and henicosanoyl, a carboxylated alkylcarbonyl group such as succinoyl, glutaroyl, adipoyl, chloroacetyl, dichloroacetyl, trichloro. Halogenoalkylcarbonyl groups such as acetyl and trifluoroacetyl, lower alkoxy lower alkylcarbonyl groups such as methoxyacetyl, (E) -2-me “Aliphatic acyl group” such as unsaturated alkylcarbonyl group such as ru-2-butenoyl; arylcarbonyl group such as benzoyl, α-naphthoyl and β-naphthoyl, 2-bromobenzoyl, 4-chlorobenzoyl A halogenoarylcarbonyl group, such as
2,4,6-Trimethylbenzoyl, lower alkylated arylcarbonyl groups such as 4-toluoyl, lower alkoxylated arylcarbonyl groups such as 4-anisoyl, 2-carboxybenzoyl, 3-carboxybenzoyl, 4 -Carboxylated arylcarbonyl groups such as carboxybenzoyl, 4-nitrobenzoyl, nitrated arylcarbonyl groups such as 2-nitrobenzoyl, lower alkoxycarbonylated aryl groups such as 2- (methoxycarbonyl) benzoyl. Lecarbonyl group, 4-
"Aromatic acyl groups" such as arylated arylcarbonyl groups such as phenylbenzoyl; tetrahydropyran-
2-yl, 3-bromotetrahydropyran-2-yl,
"Tetrahydropyranyl or tetrahydrothiopyranyl group" such as 4-methoxytetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, 4-methoxytetrahydrothiopyran-4-yl; tetrahydrofuran-2-yl, tetrahydro "Tetrahydrofuranyl or tetrahydrothiofuranyl group" such as thiofuran-2-yl; trimethylsilyl, triethylsilyl, isopropyldimethylsilyl, t-butyldimethylsilyl,
Tri-lower alkylsilyl groups such as methyldiisopropylsilyl, methyldi-t-butylsilyl, triisopropylsilyl, and one or two aryl groups such as diphenylmethylsilyl, diphenylbutylsilyl, diphenylisopropylsilyl, phenyldiisopropylsilyl. "Silyl group" such as substituted tri-lower alkylsilyl group; lower such as methoxymethyl, 1,1-dimethyl-1-methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, butoxymethyl, t-butoxymethyl Alkoxymethyl group, lower alkoxylated lower alkoxymethyl group such as 2-methoxyethoxymethyl, halogeno lower alkoxymethyl such as 2,2,2-trichloroethoxymethyl, bis (2-chloroethoxy) methyl, etc. Kokishimechiru group "; 1-ethoxyethyl, 1- (isopropoxy) lower alkoxylated ethyl group such as ethyl," substituted ethyl group such as a halogenated ethyl group such as 2,2,2-trichloroethyl; "
Benzyl, α-naphthylmethyl, β-naphthylmethyl,
Lower alkyl group substituted with 1 to 3 aryl groups such as diphenylmethyl, triphenylmethyl, α-naphthyldiphenylmethyl, 9-anthrylmethyl, 4-methylbenzyl, 2,4,6-trimethyl Benzyl, 3,
4,5-trimethylbenzyl, 4-methoxybenzyl,
4-methoxyphenyldiphenylmethyl, 2-nitrobenzyl, 4-nitrobenzyl, 4-chlorobenzyl, 4
-Lower alkyl group such as bromobenzyl, 4-cyanobenzyl, lower alkyl such as methyl, piperonyl, lower alkoxy, halogen, lower alkyl group substituted with 1 to 3 aryl groups substituted with aryl ring by cyano group “Aralkyl group” such as; lower alkoxycarbonyl group such as methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, isobutoxycarbonyl, halogen such as 2,2,2-trichloroethoxycarbonyl, 2-trimethylsilylethoxycarbonyl or tri. “Alkoxycarbonyl group” such as lower alkoxycarbonyl group substituted with lower alkylsilyl group; “alkenyloxycarbonyl group” such as vinyloxycarbonyl, allyloxycarbonyl; benzyloxycarbonyl, 4-methoxybenzyloxycarbo Le, 3,4-dimethoxybenzyl oxycarbonyl, 2-nitrobenzyloxycarbonyl, such as 4-nitrobenzyloxycarbonyl, 1
To “aralkyloxycarbonyl group” optionally substituted on the aryl ring with two lower alkoxy or nitro groups.

"Substituted hydroxyl group" in the definition of R ^4.
"Substituent" is, for example, the above "lower alkyl group";
“Lower alkanesulfonyl group” such as methanesulfonyl, ethanesulfonyl, 1-propanesulfonyl; “fluorinated lower alkanesulfonyl group” such as trifluoromethanesulfonyl, pentafluoroethanesulfonyl or benzenesulfonyl, such as p-toluenesulfonyl An "arylsulfonyl group" can be mentioned, and a "lower alkyl group" and a "fluorinated lower alkanesulfonyl group" are preferable.

The "protecting group" of the "protected carboxy group" in the definition of R ⁴ means "the protecting group in the reaction which can be cleaved by a chemical method such as hydrogenolysis, hydrolysis, electrolysis or photolysis. And is preferably the above “lower alkyl group”; the above “halogenoalkyl group” and the above “aralkyl group”.

The "lower alkoxy group" in the definition of [Substituent group A] and the "lower alkoxy group" of the "lower alkoxycarbonyl" in the definition of [Substituent group B] mean the above "lower alkyl group". A group bonded to an oxygen atom, for example, methoxy, ethoxy, n-propoxy,
Isopropoxy, n-butoxy, isobutoxy, s-butoxy, tert-butoxy, n-pentoxy, isopentoxy, 2-methylbutoxy, neopentoxy, n-
Hexyloxy, 4-methylpentoxy, 3-methylpentoxy, 2-methylpentoxy, 3,3-dimethylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1, A straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms such as 1,3-dimethylbutoxy and 2,3-dimethylbutoxy, preferably a straight-chain or branched alkoxy group having 1 to 4 carbon atoms. A group, and more preferably a methoxy group or an ethoxy group.

The "di-lower alkylamino group" in the definition of [Substituent group B] means a group in which the above-mentioned "lower alkyl group" is bonded to a nitrogen atom, and examples thereof include dimethylamino, methylethylamino, diethylamino and diamino. n-propylamino, methyl n-propylamino, diisopropylamino, din-butylamino, diisobutylamino, di-s-
Butylamino, di-tert-butylamino, di-n-pentylamino, di-isopentylamino, dineopentylamino, di-n-hexylamino, preferably a straight-chain or branched-chain dicarboxylic acid having 1 to 4 carbon atoms. It is a lower alkylamino group.

Formula-NR ² R ³ With preferred groups having
For example, amino, methylamino, ethylami
No, propylamino, isopropylamino, butylami
No, isobutylamino, t-butylamino, benzyl
Mino, 2-methylbenzylamino, 3-methylbenzyl
Amino, 4-methylbenzylamino, 2-methoxyben
Dilamino, 3-methoxybenzylamino, 4-methoxy
Cibenzylamino, 2-fluorobenzylamino, 3-
Fluorobenzylamino, 4-fluorobenzylami
2-chlorobenzylamino, 3-chlorobenzylamino
Mino, 4-chlorobenzylamino, phenethylamino,
2-methylphenethylamino, 3-methylphenethylamine
Mino, 4-methylphenethylamino, 2-methoxyphen
Netylamino, 3-methoxyphenethylamino, 4-me
Toxiphenethylamino, 2-fluorophenethylami
No, 3-fluorophenethylamino, 4-fluorophen
Netylamino, 2-chlorophenethylamino, 3-chloro
Lophenethylamino, 4-chlorophenethylamino,
(3-phenylpropyl) amino, (1-methyl-1-)
Phenylethyl) amino, [1-methyl-1- (2-me
Tylphenyl) ethyl] amino, [1-methyl-1-
(3-Methylphenyl) ethyl] amino, [1-methyl
-1- (4-methylphenyl) ethyl] amino, [1-
Methyl-1- (2-methoxyphenyl) ethyl] ami
No, [1-methyl-1- (3-methoxyphenyl) ethyl
L] amino, [1-methyl-1- (4-methoxyphenyl)
Lu) ethyl] amino, [1-methyl-1- (2-ethoxy)
Cyphenyl) ethyl] amino, [1-methyl-1- (3
-Ethoxyphenyl) ethyl] amino, [1-methyl-
1- (4-ethoxyphenyl) ethyl] amino, [1-
Methyl-1- (2-fluorophenyl) ethyl] ami
No, [1-methyl-1- (3-fluorophenyl) ethyl
L] amino, [1-methyl-1- (4-fluorophenyl)
Lu) ethyl] amino, [1-methyl-1- (2-chloro)
(Phenyl) ethyl] amino, [1-methyl-1- (3-
Chlorophenyl) ethyl] amino, [1-methyl-1-
(4-chlorophenyl) ethyl] amino, [1-methyl
-1- (2-hydroxyphenyl) ethyl] amino,
[1-methyl-1- (3-hydroxyphenyl) ethyl
L] amino, [1-methyl-1- (4-hydroxyphene
Nyl) ethyl] amino, [1-methyl-1- (2-meth)
Xycarbonylphenyl) ethyl] amino, [1-methyl
L-1- (3-methoxycarbonylphenyl) ethyl]
Amino, [1-methyl-1- (4-methoxycarbonyl)
Phenyl) ethyl] amino, [1-methyl-1- (2-
Dimethylaminophenyl) ethyl] amino, [1-methyl
L-1- (3-dimethylaminophenyl) ethyl] ami
No, [1-methyl-1- (4-dimethylaminophenyl)
Ru) ethyl] amino, [1-methyl-1- (2,3-di
Methoxyphenyl) ethyl] amino, [1-methyl-1
-(2,4-dimethoxyphenyl) ethyl] amino,
[1-Methyl-1- (2,5-dimethoxyphenyl) e
Cyl] amino, [1-methyl-1- (2,6-dimethoxy)
Cyphenyl) ethyl] amino, [1-methyl-1-
(3,4-dimethoxyphenyl) ethyl] amino, [1
-Methyl-1- (3,5-dimethoxyphenyl) ethyl
L] amino, [1-methyl-1- (3,6-dimethoxy
Phenyl) ethyl] amino, (1,1-dimethyl-2-
Phenylethyl) amino, [1,1-dimethyl-2-
(2-Methylphenyl) ethyl] amino, [1,1-di
Methyl-2- (3-methylphenyl) ethyl] amino,
[1,1-dimethyl-2- (4-methylphenyl) ethyl
Lu] amino, [1,1-dimethyl-2- (2-methoxy
Phenyl) ethyl] amino, [1,1-dimethyl-2-
(3-Methoxyphenyl) ethyl] amino, [1,1-
Dimethyl-2- (4-methoxyphenyl) ethyl] ami
No, [1,1-dimethyl-2- (2-fluorophenyl
Ru) ethyl] amino, [1,1-dimethyl-2- (3-
Fluorophenyl) ethyl] amino, [1,1-dimethyl]
Ru-2- (4-fluorophenyl) ethyl] amino,
[1,1-dimethyl-2- (2-chlorophenyl) ethyl
L] amino, [1,1-dimethyl-2- (3-chlorofluoro)
Phenyl) ethyl] amino, [1,1-dimethyl-2-
(4-chlorophenyl) ethyl] amino, benzhydrido
Luamino, (2,2'-dimethylbenzhydryl) ami
No, (2,3'-dimethylbenzhydryl) amino,
(2,4'-Dimethylbenzhydryl) amino, (3,4
3'-Dimethylbenzhydryl) amino, (3,4'-
Dimethylbenzhydryl) amino, (4,4'-dimethyl)
Rubenzhydryl) amino, (2,2'-dimethoxybenzoyl)
Nzhydryl) amino, (2,3'-dimethoxybenz)
Hydryl) amino, (2,4'-dimethoxybenzhydride)
(Ryl) amino, (3,3'-dimethoxybenzhydri)
) Amino, (3,4'-dimethoxybenzhydryl)
Amino, (4,4'-dimethoxybenzhydryl) ami
No, (2,2'-difluorobenzhydryl) amino,
(2,3'-difluorobenzhydryl) amino,
(2,4'-difluorobenzhydryl) amino,
(3,3′-difluorobenzhydryl) amino,
(3,4'-difluorobenzhydryl) amino,
(4,4'-difluorobenzhydryl) amino,
(2,2'-dihydroxybenzhydryl) amino,
(2,3'-dihydroxybenzhydryl) amino,
(2,4'-dihydroxybenzhydryl) amino,
(3,3'-dihydroxybenzhydryl) amino,
(3,4'-dihydroxybenzhydryl) amino,
(4,4'-dihydroxybenzhydryl) amino,
(2-methylbenzhydryl) amino, (3-methylbenzhydryl)
Amino, (4-methylbenzhydryl)
Amino, (2-methoxybenzhydryl) amino, (3
-Methoxybenzhydryl) amino, (4-methoxybenzoyl)
Ntuhydryl) amino, (2-fluorobenzhydrido)
A) amino, (3-fluorobenzhydryl) amino,
(4-Fluorobenzhydryl) amino, (2-chloro
Benzhydryl) amino, (3-chlorobenzhydryl)
Amino), (4-chlorobenzhydryl) amino,
(2-hydroxybenzhydryl) amino, (3-hydr
Roxybenzhydryl) amino, (4-hydroxyben
Tsuhydryl) amino, (1,1-diphenylethyl) a
Mino, (1,2-diphenylethyl) amino, [2-
(2-Methylphenyl) -1-phenylethyl] ami
No, [2- (3-methylphenyl) -1-phenylethyl
Lu] amino, [2- (4-methylphenyl) -1-phen]
Nylethyl] amino, [2- (2-methoxyphenyl)]
-1-Phenylethyl] amino, [2- (3-methoxy
Phenyl) -1-phenylethyl] amino, [2- (4
-Methoxyphenyl) -1-phenylethyl] amino,
[2- (2-fluorophenyl) -1-phenylethyl
Lu] amino, [2- (3-fluorophenyl) -1-ph
Phenylethyl] amino, [2- (4-fluorophenyl)
) -1-Phenylethyl] amino, [2- (2-chloro)
Rophenyl) -1-phenylethyl] amino, [2-
(3-Chlorophenyl) -1-phenylethyl] ami
No, [2- (4-chlorophenyl) -1-phenylethyl
Lu] amino, [1- (2-fluorophenyl) -2-
(2-Fluorophenyl) ethyl] amino, [1- (2
-Fluorophenyl) -2- (3-fluorophenyl)
Ethyl] amino, [1- (2-fluorophenyl) -2
-(4-Fluorophenyl) ethyl] amino, [1-
(3-Fluorophenyl) -2- (2-fluorophenyl)
Ru) ethyl] amino, [1- (3-fluorophenyl)]
-2- (3-Fluorophenyl) ethyl] amino, [1
-(3-Fluorophenyl) -2- (4-fluorophene
Nyl) ethyl] amino, [1- (4-fluorophenyl)
) -2- (2-Fluorophenyl) ethyl] amino,
[1- (4-fluorophenyl) -2- (3-fluoro
Phenyl) ethyl] amino, [1- (4-fluorophene
Nyl) -2- (4-fluorophenyl) ethyl] ami
No, [1- (2-chlorophenyl) -2- (2-chloro
Phenyl) ethyl] amino, [1- (2-chlorophenyl)
) -2- (3-chlorophenyl) ethyl] amino,
[1- (2-chlorophenyl) -2- (4-chlorophene
Nyl) ethyl] amino, [1- (3-chlorophenyl)
-2- (2-chlorophenyl) ethyl] amino, [1-
(3-chlorophenyl) -2- (3-chlorophenyl)
Ethyl] amino, [1- (3-chlorophenyl) -2-
(4-chlorophenyl) ethyl] amino, [1- (4-
Chlorophenyl) -2- (2-chlorophenyl) eth
L] amino, [1- (4-chlorophenyl) -2- (3
-Chlorophenyl) ethyl] amino, [1- (4-chloro)
Rophenyl) -2- (4-chlorophenyl) ethyl] a
Mino, [1- (2-chlorophenyl) -2- (2-meth)
Xyphenyl) ethyl] amino, [1- (2-chlorophenyl)
Phenyl) -2- (3-methoxyphenyl) ethyl] ami
No, [1- (2-chlorophenyl) -2- (4-methoxy)
Cyphenyl) ethyl] amino, [1- (3-chlorophene
Nyl) -2- (2-methoxyphenyl) ethyl] ami
No, [1- (3-chlorophenyl) -2- (3-methoxy)
Cyphenyl) ethyl] amino, [1- (3-chlorophene
Nyl) -2- (4-methoxyphenyl) ethyl] ami
No, [1- (4-chlorophenyl) -2- (2-methoxy)
Cyphenyl) ethyl] amino, [1- (4-chlorophene
Nyl) -2- (3-methoxyphenyl) ethyl] ami
No, [1- (4-chlorophenyl) -2- (4-methoxy)
Cyphenyl) ethyl] amino, [1- (2-methylphene)
Nil) -2- (2-methylphenyl) ethyl] amino,
[1- (2-methylphenyl) -2- (3-methylphene
Nyl) ethyl] amino, [1- (2-methylphenyl)]
-2- (4-methylphenyl) ethyl] amino, [1-
(3-Methylphenyl) -2- (2-methylphenyl)
Ethyl] amino, [1- (3-methylphenyl) -2-
(3-Methylphenyl) ethyl] amino, [1- (3-
Methylphenyl) -2- (4-methylphenyl) eth
Lu] amino, [1- (4-methylphenyl) -2- (2
-Methylphenyl) ethyl] amino, [1- (4-methyl)
Ruphenyl) -2- (3-methylphenyl) ethyl] a
Mino, [1- (4-methylphenyl) -2- (4-methyl)
Ruphenyl) ethyl] amino, [1- (2-hydroxy
Phenyl) -2- (2-hydroxyphenyl) ethyl]
Amino, [1- (2-hydroxyphenyl) -2- (3
-Hydroxyphenyl) ethyl] amino, [1- (2-
Hydroxyphenyl) -2- (4-hydroxyphenyl)
Ru) ethyl] amino, [1- (3-hydroxyphenyl)
L) -2- (2-hydroxyphenyl) ethyl] ami
No, [1- (3-hydroxyphenyl) -2- (3-hi)
Droxyphenyl) ethyl] amino, [1- (3-hydr
Roxyphenyl) -2- (4-hydroxyphenyl) e
Cyl] amino, [1- (4-hydroxyphenyl) -2
-(2-hydroxyphenyl) ethyl] amino, [1-
(4-hydroxyphenyl) -2- (3-hydroxyphenyl)
Phenyl) ethyl] amino, [1- (4-hydroxyphene
Nyl) -2- (4-hydroxyphenyl) ethyl] ami
No, [2- (2-fluorophenyl) -1- (2-methyl)
Ruphenyl) ethyl] amino, [2- (2-fluorophenyl)
Phenyl) -1- (3-methylphenyl) ethyl] ami
No, [2- (2-fluorophenyl) -1- (4-methyl)
Ruphenyl) ethyl] amino, [2- (3-fluorophenyl)
Phenyl) -1- (2-methylphenyl) ethyl] ami
No, [2- (3-fluorophenyl) -1- (3-methyl)
Ruphenyl) ethyl] amino, [2- (3-fluorophenyl)
Phenyl) -1- (4-methylphenyl) ethyl] ami
No, [2- (4-fluorophenyl) -1- (2-methyl)
Ruphenyl) ethyl] amino, [2- (4-fluorophenyl)
Phenyl) -1- (3-methylphenyl) ethyl] ami
No, [2- (4-fluorophenyl) -1- (4-methyl)
Luphenyl) ethyl] amino, 2- (2-fluorophene
Nyl) -1- (2-methoxyphenyl) ethyl] ami
No, 2- (2-fluorophenyl) -1- (3-methoxy)
Cyphenyl) ethyl] amino, 2- (2-fluorophene
Nyl) -1- (4-methoxyphenyl) ethyl] ami
No, 2- (3-fluorophenyl) -1- (2-methoxy)
Cyphenyl) ethyl] amino, 2- (3-fluorophe
Nyl) -1- (3-methoxyphenyl) ethyl] ami
No, 2- (3-fluorophenyl) -1- (4-methoxy)
Cyphenyl) ethyl] amino, 2- (4-fluorophe
Nyl) -1- (2-methoxyphenyl) ethyl] ami
No, 2- (4-fluorophenyl) -1- (3-methoxy)
Cyphenyl) ethyl] amino, 2- (4-fluorophe
Nyl) -1- (4-methoxyphenyl) ethyl] ami
No, [2- (2-hydroxyphenyl) -1-phenyl
Ethyl] amino, [2- (3-hydroxyphenyl)-
1-phenylethyl] amino, [2- (4-hydroxy
Phenyl) -1-phenylethyl] amino, [1- (2
-Methoxyphenyl) -2-phenylethyl] amino,
[1- (3-methoxyphenyl) -2-phenylethyl
Lu] amino, [1- (4-methoxyphenyl) -2-ph
Phenylethyl] amino, (1-methyl-1,2-dife
Nylethyl) amino, (2,2-diphenylethyl) a
Mino, [2- (2-methylphenyl) -2- (2-methyl)
Ruphenyl) ethyl] amino, [2- (2-methylphene)
Nil) -2- (3-methylphenyl) ethyl] amino,
[2- (2-methylphenyl) -2- (4-methylphene)
Nyl) ethyl] amino, [2- (3-methylphenyl)]
-2- (3-methylphenyl) ethyl] amino, [2-
(3-Methylphenyl) -2- (4-methylphenyl)
Ethyl] amino, [2- (4-methylphenyl) -2-
(4-Methylphenyl) ethyl] amino, [2- (2-
Methoxyphenyl) -2- (2-methoxyphenyl) d
Cyl] amino, [2- (2-methoxyphenyl) -2-
(3-Methoxyphenyl) ethyl] amino, [2- (2
-Methoxyphenyl) -2- (4-methoxyphenyl)
Ethyl] amino, [2- (3-methoxyphenyl) -2
-(3-Methoxyphenyl) ethyl] amino, [2-
(3-Methoxyphenyl) -2- (4-methoxyphenyl)
Ru) ethyl] amino, [2- (4-methoxyphenyl)]
-2- (4-methoxyphenyl) ethyl] amino, (1
-Benzyl-4-phenylbutyl) amino, (1,1-
Diphenylethyl) amino, [1- (2-fluorophene
Nyl) -1- (2-fluorophenyl) ethyl] ami
No, [1- (2-fluorophenyl) -1- (3-full
Orophenyl) ethyl] amino, [1- (2-fluoro
Phenyl) -1- (4-fluorophenyl) ethyl] a
Mino, [1- (3-fluorophenyl) -1- (3-phenyl)
Luorophenyl) ethyl] amino, [1- (3-fluor
Rophenyl) -1- (4-fluorophenyl) ethyl]
Amino, [1- (4-fluorophenyl) -1- (4-
Fluorophenyl) ethyl] amino, [1- (2-methyl
Ruphenyl) -1- (2-methylphenyl) ethyl] a
Mino, [1- (2-methylphenyl) -1- (3-methyl)
Ruphenyl) ethyl] amino, [1- (2-methylphene)
Nil) -1- (4-methylphenyl) ethyl] amino,
[1- (3-methylphenyl) -1- (3-methylphene
Nyl) ethyl] amino, [1- (3-methylphenyl)]
-1- (4-methylphenyl) ethyl] amino, [1-
(4-methylphenyl) -1- (4-methylphenyl)
Ethyl] amino, [1- (2-methoxyphenyl) -1
-(2-Methoxyphenyl) ethyl] amino, [1-
(2-methoxyphenyl) -1- (3-methoxyphenyl)
Ru) ethyl] amino, [1- (2-methoxyphenyl)]
-1- (4-methoxyphenyl) ethyl] amino, [1
-(3-Methoxyphenyl) -1- (3-methoxyphen)
Nyl) ethyl] amino, [1- (3-methoxyphenyl)
) -1- (4-Methoxyphenyl) ethyl] amino,
[1- (4-methoxyphenyl) -1- (4-methoxy
Phenyl) ethyl] amino, [1- (2-hydroxyphenyl)
Phenyl) -1-phenylethyl] amino, [1- (3-
Hydroxyphenyl) -1-phenylethyl] amino,
[1- (4-hydroxyphenyl) -1-phenylethyl
Lu] amino, tritylamino, 2,2 ', 2 "-trimethyl
Tiltlytylamino, 2,2 ', 3 "-trimethyltri
Cylamino, 2,2 ', 4 "-trimethyltritylami
No, 2,3 ', 3 "-trimethyltritylamino, 2,
3 ', 4 "-trimethyltritylamino, 3,3',
3 "-trimethyltritylamino, 3,3 ', 4" -to
Limethyltritylamino, 3,4 ', 4 "-trimethyl
Tritylamino, 4,4 ', 4 "-trimethyltrityl
Amino, 2,2 ', 2 "-trifluorotritylami
No, 2,2 ', 3 "-trifluorotritylamino,
2,2 ', 4 "-trifluorotritylamino, 2,
3 ', 3 "-trifluorotritylamino, 2,3',
4 "-trifluorotritylamino, 3,3 ', 3"-
Trifluorotritylamino, 3,3 ', 4 "-trif
Luorotritylamino, 3,4 ', 4 "-trifluoro
Tritylamino, 4,4 ', 4 "-trifluorotriti
Luamino, (1-benzyl-2-phenylethyl) ami
No, [1- (2-fluorobenzyl) -2- (2-full
Orophenyl) ethyl] amino, [1- (2-fluoro
Benzyl) -2- (3-fluorophenyl) ethyl] a
Mino, [1- (2-fluorobenzyl) -2- (4-phenyl)
Luorophenyl) ethyl] amino, [1- (3-fluor
Robenzyl) -2- (3-fluorophenyl) ethyl]
Amino, [1- (3-fluorobenzyl) -2- (4-
Fluorophenyl) ethyl] amino, [1- (4-full
Orobenzyl) -2- (4-fluorophenyl) eth
Lu] amino, (1-benzyl-1-methyl-2-phenyl
Ruethyl) amino, [1- (2-chlorobenzyl) -2
-(2-chlorophenyl) ethyl] amino, [1- (2
-Chlorobenzyl) -2- (3-chlorophenyl) eth
Lu] amino, [1- (2-chlorobenzyl) -2- (4
-Chlorophenyl) ethyl] amino, [1- (3-chloro)
Robenzyl) -2- (3-chlorophenyl) ethyl] a
Mino, [1- (3-chlorobenzyl) -2- (4-chloro)
Rophenyl) ethyl] amino, [1- (4-chloroben
Dil) -2- (4-chlorophenyl) ethyl] amino,
[1- (2-fluorobenzyl) -2- (2-fluoro
Phenyl) -1-methylethyl] amino, [1- (2-
Fluorobenzyl) -2- (3-fluorophenyl)-
1-methylethyl] amino, [1- (2-fluoroben
Dil) -2- (4-fluorophenyl) -1-methyle
Cyl] amino, [1- (3-fluorobenzyl) -2-
(3-Fluorophenyl) -1-methylethyl] ami
No, [1- (3-fluorobenzyl) -2- (4-full
Orophenyl) -1-methylethyl] amino, [1-
(4-Fluorobenzyl) -2- (4-fluorophenyl)
1-methylethyl] amino, [1-methyl-2-]
(2-Methylphenyl) -3- (2-methylphenyl)
Propyl] amino, [1-methyl-2- (2-methylphenyl)
Phenyl) -3- (3-methylphenyl) propyl] ami
No, [1-methyl-2- (2-methylphenyl) -3-
(4-Methylphenyl) propyl] amino, [1-methyl
2- (3-methylphenyl) -3- (2-methylphenyl)
Phenyl) propyl] amino, [1-methyl-2- (3-
Methylphenyl) -3- (3-methylphenyl) propyi
Lu] amino, [1-methyl-2- (3-methylphenyl)
) -3- (4-Methylphenyl) propyl] amino,
[1-methyl-2- (4-methylphenyl) -3- (2
-Methylphenyl) propyl] amino, [1-methyl-
2- (4-methylphenyl) -3- (3-methylpheny
) Propyl] amino, [1-methyl-2- (4-methyl)
Ruphenyl) -3- (4-methylphenyl) propyl]
Amino, [2- (2-fluorophenyl) -3- (2-
Fluorophenyl) -1-methylpropyl] amino,
[2- (2-fluorophenyl) -3- (3-fluoro
Phenyl) -1-methylpropyl] amino, [2- (2
-Fluorophenyl) -3- (4-fluorophenyl)
-1-methylpropyl] amino, [2- (3-fluoro
Phenyl) -3- (2-fluorophenyl) -1-methyl
Lupropyl] amino, [2- (3-fluorophenyl)
-3- (3-fluorophenyl) -1-methylpropyi
Lu] amino, [2- (3-fluorophenyl) -3-
(4-Fluorophenyl) -1-methylpropyl] ami
No, [2- (4-fluorophenyl) -3- (2-full
Orophenyl) -1-methylpropyl] amino, [2-
(4-fluorophenyl) -3- (3-fluorophenyl)
) -1-methylpropyl] amino, [2- (4-full
Orophenyl) -3- (4-fluorophenyl) -1-
Methylpropyl] amino, (1,3-diphenylpropy
) Amino, [1- (2-methylphenyl) -3- (2
-Methylphenyl) propyl] amino, [1- (2-me
Ctylphenyl) -3- (3-methylphenyl) propyi
L] amino, [1- (2-methylphenyl) -3- (4
-Methylphenyl) propyl] amino, [1- (3-me
Tylphenyl) -3- (2-methylphenyl) propyi
L] amino, [1- (3-methylphenyl) -3- (3
-Methylphenyl) propyl] amino, [1- (3-me
Tylphenyl) -3- (4-methylphenyl) propyi
L] amino, [1- (4-methylphenyl) -3- (2
-Methylphenyl) propyl] amino, [1- (4-me
Ctylphenyl) -3- (3-methylphenyl) propyi
L] amino, [1- (4-methylphenyl) -3- (4
-Methylphenyl) propyl] amino, [1- (2-me
Toxyphenyl) -3- (2-methoxyphenyl) pro
Pill] amino, [1- (2-methoxyphenyl) -3-
(3-Methoxyphenyl) propyl] amino, [1-
(2-Methoxyphenyl) -3- (4-methoxyphenyl)
) Propyl] amino, [1- (3-methoxyphenyl)
) -3- (2-Methoxyphenyl) propyl] ami
No, [1- (3-methoxyphenyl) -3- (3-meth)
Xyphenyl) propyl] amino, [1- (3-methoxy)
Cyphenyl) -3- (4-methoxyphenyl) propyi
L] amino, [1- (4-methoxyphenyl) -3-
(2-Methoxyphenyl) propyl] amino, [1-
(4-Methoxyphenyl) -3- (3-methoxyphenyl)
) Propyl] amino, [1- (4-methoxyphenyl)
) -3- (4-Methoxyphenyl) propyl] ami
No, (1,4-diphenylbutyl) amino, [1- (2
-Chlorophenyl) -4- (2-chlorophenyl) buty
Ru] amino, [1- (2-chlorophenyl) -4- (3
-Chlorophenyl) butyl] amino, [1- (2-chloro)
Rophenyl) -4- (4-chlorophenyl) butyl] a
Mino, [1- (3-chlorophenyl) -4- (2-chloro)
Rophenyl) butyl] amino, [1- (3-chlorophene
Nyl) -4- (3-chlorophenyl) butyl] amino,
[1- (3-chlorophenyl) -4- (4-chlorophene
Nyl) butyl] amino, [1- (4-chlorophenyl)
-4- (2-chlorophenyl) butyl] amino, [1-
(4-chlorophenyl) -4- (3-chlorophenyl)
Butyl] amino, [1- (4-chlorophenyl) -4-
(4-chlorophenyl) butyl] amino, [1- (2-
Methoxyphenyl) -4- (2-methoxyphenyl) bu
Cyl] amino, [1- (2-methoxyphenyl) -4-
(3-Methoxyphenyl) butyl] amino, [1- (2
-Methoxyphenyl) -4- (4-methoxyphenyl)
Butyl] amino, [1- (3-methoxyphenyl) -4
-(2-Methoxyphenyl) butyl] amino, [1-
(3-methoxyphenyl) -4- (3-methoxyphenyl)
Ru) butyl] amino, [1- (3-methoxyphenyl)]
-4- (4-methoxyphenyl) butyl] amino, [1
-(4-Methoxyphenyl) -4- (2-methoxyphen)
Nyl) butyl] amino, [1- (4-methoxyphenyl)
) -4- (3-Methoxyphenyl) butyl] amino,
[1- (4-methoxyphenyl) -4- (4-methoxy)
Phenyl) butyl] amino, (1-methyl-3,3-di
Phenylpropyl) amino, [3- (2-fluorophene
Nyl) -3- (2-fluorophenyl) -1-methylpropyl
Ropyr] amino, [3- (2-fluorophenyl) -3
-(3-Fluorophenyl) -1-methylpropyl] a
Mino, [3- (2-fluorophenyl) -3- (4-phenyl)
Luorophenyl) -1-methylpropyl] amino, [3
-(3-Fluorophenyl) -3- (3-fluorophene
Nyl) -1-methylpropyl] amino, [3- (3-phenyl)
Luorophenyl) -3- (4-fluorophenyl) -1
-Methylpropyl] amino, [3- (4-fluorophene
Nyl) -3- (4-fluorophenyl) -1-methylpropyl
Ropil] amino, [1-methyl-3- (2-methylphene)
Nyl) -3- (2-methylphenyl) propyl] ami
No, [1-methyl-3- (2-methylphenyl) -3-
(3-Methylphenyl) propyl] amino, [1-methyl
Le-3- (2-methylphenyl) -3- (4-methylphenyl)
Phenyl) propyl] amino, [1-methyl-3- (3-
Methylphenyl) -3- (3-methylphenyl) propyi
L] amino, [1-methyl-3- (3-methylphenyl)
) -3- (4-Methylphenyl) propyl] amino,
[1-methyl-3- (4-methylphenyl) -3- (4
-Methylphenyl) propyl] amino, (2-furylme
(Cyl) amino, (3-furylmethyl) amino, (2-thi
(Enylmethyl) amino, (3-thienylmethyl) ami
No, (2-pyridylmethyl) amino, (3-pyridylme
(Cyl) amino, (4-pyridylmethyl) amino, (2-
Methyl-3-furylmethyl) amino, (5-methyl-2)
-Furylmethyl) amino, (5-methyl-3-furylme)
Cyl) amino, (2-methyl-3-thienylmethyl) a
Mino, (5-methyl-2-thienylmethyl) amino,
(5-methyl-3-thienylmethyl) amino, [2-
(2-Furyl) ethyl] amino, [2- (3-furyl)]
Ethyl] amino, [2- (2-thienyl) ethyl] ami
No, [2- (3-thienyl) ethyl] amino, [3-
(2-furyl) propyl] amino, [3- (3-free
Ru) propyl] amino, [3- (2-thienyl) propyi
L] amino, [3- (3-thienyl) propyl] ami
No, [bis (2-furyl) methyl] amino, [bis (3
-Furyl) methyl] amino, [bis (2-thienyl) meth
Cyl] amino, [bis (3-thienyl) methyl] ami
No, [1,1-bis (2-furyl) ethyl] amino,
[1,1-bis (3-furyl) ethyl] amino, [1,
1-bis (2-thienyl) ethyl] amino, [1,1-
Bis (3-thienyl) ethyl] amino, [(2-methyl
-3-furylmethyl), (2-methyl-3-furylmethyl)
)] Amino, [(2-methyl-3-furylmethyl),
(5-Methyl-2-furylmethyl)] amino, [(2-
Methyl-3-furylmethyl), (5-methyl-3-free)
Lumethyl)] amino, [(5-methyl-2-furylmethyi)
,) (5-methyl-2-furylmethyl)] amino,
[(5-Methyl-2-furylmethyl), (5-methyl-
3-furylmethyl)] amino, [(5-methyl-3-furyl)
Rylmethyl), (5-methyl-3-furylmethyl)] a
Mino, [(2-methyl-3-thienylmethyl), (2-
Methyl-3-thienylmethyl)] amino, [(2-methyl
L-3-thienylmethyl), (5-methyl-2-thienyl)
Lumethyl)] amino, [(2-methyl-3-thienylme
Til), (5-methyl-3-thienylmethyl)] ami
No, [(5-methyl-2-thienylmethyl), (5-me
Tyl-2-thienylmethyl)] amino, [(5-methyl
-2-thienylmethyl), (5-methyl-3-thienyl)
Methyl)] amino, [(5-methyl-3-thienylmethyi)
), (5-methyl-3-thienylmethyl)] amino,
[1- (2-furyl) -1-methylethyl] amino,
[1- (3-furyl) -1-methylethyl] amino,
[1- (2-thienyl) -1-methylethyl] amino,
[1- (3-thienyl) -1-methylethyl] amino,
[1- (2-methyl-3-thienyl) -1-methylethyl
Ru] amino, [1- (5-methyl-2-thienyl) -1]
-Methylethyl] amino, [1- (5-methyl-3-thio)
(Enyl) -1-methylethyl] amino, [1- (2-phenyl)
Ryl) -2- (2-furyl) ethyl] amino, [1-
(2-furyl) -2- (3-furyl) ethyl] amino,
[1- (3-furyl) -2- (2-furyl) ethyl] a
Mino, [1- (3-furyl) -2- (3-furyl) eth
Ru] amino, [1- (2-methyl-3-furyl) -1-
Methylethyl] amino, [1- (5-methyl-2-free)
) -1-Methylethyl] amino, [1- (5-methyl
-3-furyl) -1-methylethyl] amino, [1-
(2-thienyl) -2- (2-thienyl) ethyl] ami
No, [1- (2-thienyl) -2- (3-thienyl) e
Cyl] amino, [1- (3-thienyl) -2- (2-thi
(Enyl) ethyl] amino, [1- (3-thienyl) -2]
-(3-thienyl) ethyl] amino, [1- (2-free
) -2-Phenylethyl] amino, [1- (3-free
) -2-Phenylethyl] amino, [1- (2-free
) -2- (2-Methylphenyl) ethyl] amino,
[1- (2-furyl) -2- (3-methylphenyl) e
Cyl] amino, [1- (2-furyl) -2- (4-methyl)
Ruphenyl) ethyl] amino, [1- (3-furyl)-
2- (2-methylphenyl) ethyl] amino, [1-
(3-furyl) -2- (3-methylphenyl) ethyl]
Amino, [1- (3-furyl) -2- (4-methylphene)
Nyl) ethyl] amino, [2-phenyl-1- (2-3
-Thienyl) ethyl] amino, [2-phenyl-1-
(3-thienyl) ethyl] amino, [1-phenyl-2
-(2-thienyl) ethyl] amino, [1-phenyl-
2- (3-thienyl) ethyl] amino, [2- (2-me
Cylphenyl) -1- (2-thienyl) ethyl] ami
No, [2- (3-methylphenyl) -1- (2-thienyl)
Ru) ethyl] amino, [2- (4-methylphenyl)-
1- (2-thienyl) ethyl] amino, [2- (2-me
Cylphenyl) -1- (3-thienyl) ethyl] ami
No, [2- (3-methylphenyl) -1- (3-thieni)
Ru) ethyl] amino, [2- (4-methylphenyl)-
1- (3-thienyl) ethyl] amino, [2- (2-q
Lolophenyl) -1- (2-thienyl) ethyl] ami
No, [2- (3-chlorophenyl) -1- (2-thienyl)
Ru) ethyl] amino, [2- (4-chlorophenyl)-
1- (2-thienyl) ethyl] amino, [2- (2-q
Lolophenyl) -1- (3-thienyl) ethyl] ami
No, [2- (3-chlorophenyl) -1- (3-thieni)
Ru) ethyl] amino, [2- (4-chlorophenyl)-
1- (3-thienyl) ethyl] amino, [2- (2-phenyl)
Luorophenyl) -1- (2-thienyl) ethyl] ami
No, [2- (3-fluorophenyl) -1- (2-thie
Nyl) ethyl] amino, [2- (4-fluorophenyl)
L) -1- (2-thienyl) ethyl] amino, [2-
(2-Fluorophenyl) -1- (3-thienyl) eth
Ru] amino, [2- (3-fluorophenyl) -1-
(3-thienyl) ethyl] amino, [2- (4-fluor
Lophenyl) -1- (3-thienyl) ethyl] amino,
[2- (2-methoxyphenyl) -1- (2-thienyl)
Ru) ethyl] amino, [2- (3-methoxyphenyl)
-1- (2-thienyl) ethyl] amino, [2- (4-
Methoxyphenyl) -1- (2-thienyl) ethyl] a
Mino, [2- (2-methoxyphenyl) -1- (3-thio)
(Enyl) ethyl] amino, [2- (3-methoxyphenyl)
L) -1- (3-thienyl) ethyl] amino, [2-
(4-Methoxyphenyl) -1- (3-thienyl) eth
Lu] amino, [1- (2-fluorophenyl) -2-
(2-thienyl) ethyl] amino, [1- (3-fluor
Lophenyl) -2- (2-thienyl) ethyl] amino,
[1- (4-fluorophenyl) -2- (2-thieny
Ru) ethyl] amino, [1- (2-fluorophenyl)]
-2- (3-thienyl) ethyl] amino, [1- (3-
Fluorophenyl) -2- (3-thienyl) ethyl] a
Mino, [1- (4-fluorophenyl) -2- (3-thio)
(Enyl) ethyl] amino, cyclopropylmethylami
No, cyclobutylmethylamino, cyclopentylmethyl
Amino, cyclohexylmethylamino, 4-methylcyclo
Rohexylmethylamino, 4-methoxycyclohexyl
Methylamino, 4-fluorochlorohexylmethylami
No, 4-chlorocyclohexylmethylamino, allyla
Mino, methallylamino, 2-butenylamino, 2-pe
Intenylamino, 2-hexenylamino, cyclopropyi
Luamino, cyclobutylamino, cyclopentylami
No, cyclohexylamino, 4-methylcyclohexyl
Amino, 4-methoxycyclohexylamino, 4-full
Oroclohexylamino, 4-chlorocyclohexyl
Mino, N, N-dimethylamino, N, N-diethylami
No, N-benzyl-N-methylamino, N-benzyl-
N-ethylamino, N-benzyl-N-isopropyla
Mino, N-benzyl-N-isobutylamino, N-ben
Zyl-Nt-butylamino, N- (2-fluoroben
Dil) -N-isopropylamino, N- (3-fluoro
Benzyl) -N-isopropylamino, N- (4-full
Orobenzyl) -N-isopropylamino, N- (2-
Chlorobenzyl) -N-isopropylamino, N- (3
-Chlorobenzyl) -N-isopropylamino, N-
(4-chlorobenzyl) -N-isopropylamino, N
-(2-methylbenzyl) -N-isopropylamino,
N- (3-methylbenzyl) -N-isopropylamido
No, N- (4-methylbenzyl) -N-isopropyla
Mino, N- (2-methoxybenzyl) -N-isopropylate
Luamino, N- (3-methoxybenzyl) -N-isop
Ropyramino, N- (4-methoxybenzyl) -N-i
Sopropylamino, N- (2-hydroxybenzyl)-
N-isopropylamino, N- (3-hydroxybenzyl
) -N-isopropylamino, N- (4-hydroxy)
Benzyl) -N-isopropylamino, N, N-diben
Dilamino, N-benzyl-N- (2-methoxybenzi
L) amino, N-benzyl-N- (3-methoxybenzyl
) Amino, N-benzyl-N- (4-methoxybenzyl
Ru) amino, N- (2-fluorobenzyl) -N- (2
-Fluorobenzyl) amino, N- (2-fluoroben
Dil) -N- (3-fluorobenzyl) amino, N-
(2-Fluorobenzyl) -N- (4-fluorobenzyl
Ru) amino, N- (3-fluorobenzyl) -N- (3
-Fluorobenzyl) amino, N- (3-fluoroben
Dil) -N- (4-fluorobenzyl) amino, N-
(4-Fluorobenzyl) -N- (4-fluorobenzyl
Ru) amino, N- (2-methylbenzyl) -N- (2-
Methylbenzyl) amino, N- (2-methylbenzyl)
-N- (3-methylbenzyl) amino, N- (2-methyl
Rubenzyl) -N- (4-methylbenzyl) amino, N
-(3-Methylbenzyl) -N- (3-methylbenzyl
L) amino, N- (3-methylbenzyl) -N- (4-
Methylbenzyl) amino, N- (4-methylbenzyl)
-N- (4-methylbenzyl) amino, N- (2-meth
Xybenzyl) -N- (2-methoxybenzyl) ami
No, N- (2-methoxybenzyl) -N- (3-methoxy)
Cibenzyl) amino, N- (2-methoxybenzyl)-
N- (4-methoxybenzyl) amino, N- (3-meth
Xybenzyl) -N- (3-methoxybenzyl) ami
No, N- (3-methoxybenzyl) -N- (4-methoxy)
Cibenzyl) amino, N- (4-methoxybenzyl)-
N- (4-methoxybenzyl) amino, N- (2-hydr
Roxybenzyl) -N- (2-hydroxybenzyl) a
Mino, N- (2-hydroxybenzyl) -N- (3-hi
Droxybenzyl) amino, N- (2-hydroxyben
Dil) -N- (4-hydroxybenzyl) amino, N-
(3-hydroxybenzyl) -N- (3-hydroxy ester
), N- (3-hydroxybenzyl) -N
-(4-hydroxybenzyl) amino, N- (4-hydr
Roxybenzyl) -N- (4-hydroxybenzyl) a
Mino, N-benzyl-N-phenylethylamino, N-
Benzyl-N- (1-phenylethyl) amino, N-be
N-N- (1-methyl-1-phenylethyl) ami
No, N, N-diphenylethylamino, N, N-bis
(1-phenylethyl) amino, N-benzyl-N-
(3-phenylpropyl) amino, N-benzyl-N-
(2-furylmethyl) amino, N-benzyl-N- (3
-Furylmethyl) amino, N-benzyl-N- (2-thi
Enenylmethyl) amino, N-benzyl-N- (3-thie
Nylmethyl) amino, N- (2-furylmethyl) -N-
(2-furylmethyl) amino, N- (2-furylmethyl)
Ru) -N- (3-furylmethyl) amino, N- (3-furyl)
Rylmethyl) -N- (3-furylmethyl) amino, N-
(2-thienylmethyl) -N- (2-thienylmethyl)
Amino, N- (2-thienylmethyl) -N- (3-thiet
Nylmethyl) amino or N- (3-thienylmethyl)-
It may be an N- (3-thienylmethyl) amino group.

More preferably, isopropylamino, isobutylamino, t-butylamino, (1-methyl-1-)
Phenylethyl) amino, [1-methyl-1- (2-methylphenyl) ethyl] amino, [1-methyl-1-
(3-Methylphenyl) ethyl] amino, [1-methyl-1- (4-methylphenyl) ethyl] amino, [1-
Methyl-1- (2-methoxyphenyl) ethyl] amino, [1-methyl-1- (3-methoxyphenyl) ethyl] amino, [1-methyl-1- (4-methoxyphenyl) ethyl] amino, [1 -Methyl-1- (2-ethoxyphenyl) ethyl] amino, [1-methyl-1- (3
-Ethoxyphenyl) ethyl] amino, [1-methyl-
1- (4-ethoxyphenyl) ethyl] amino, [1-
Methyl-1- (2-fluorophenyl) ethyl] amino, [1-methyl-1- (3-fluorophenyl) ethyl] amino, [1-methyl-1- (4-fluorophenyl) ethyl] amino, [1 -Methyl-1- (2-chlorophenyl) ethyl] amino, [1-methyl-1- (3-
Chlorophenyl) ethyl] amino, [1-methyl-1-
(4-chlorophenyl) ethyl] amino, [1-methyl-1- (2-hydroxyphenyl) ethyl] amino,
[1-Methyl-1- (3-hydroxyphenyl) ethyl] amino, [1-methyl-1- (4-hydroxyphenyl) ethyl] amino, [1-methyl-1- (2-methoxycarbonylphenyl) ethyl] Amino, [1-methyl-1- (3-methoxycarbonylphenyl) ethyl]
Amino, [1-methyl-1- (4-methoxycarbonylphenyl) ethyl] amino, [1-methyl-1- (2-
Dimethylaminophenyl) ethyl] amino, [1-methyl-1- (3-dimethylaminophenyl) ethyl] amino, [1-methyl-1- (4-dimethylaminophenyl) ethyl] amino, [1-methyl-1 -(2,3-Dimethoxyphenyl) ethyl] amino, [1-methyl-1
-(2,4-dimethoxyphenyl) ethyl] amino,
[1-Methyl-1- (2,5-dimethoxyphenyl) ethyl] amino, [1-methyl-1- (2,6-dimethoxyphenyl) ethyl] amino, [1-methyl-1-
(3,4-dimethoxyphenyl) ethyl] amino, [1
-Methyl-1- (3,5-dimethoxyphenyl) ethyl] amino, [1-methyl-1- (3,6-dimethoxyphenyl) ethyl] amino, (1,1-dimethyl-2-
Phenylethyl) amino, benzhydrylamino,
(2,2'-Dimethylbenzhydryl) amino, (2,2 '
3'-Dimethylbenzhydryl) amino, (2,4'-
Dimethylbenzhydryl) amino, (3,3′-dimethylbenzhydryl) amino, (3,4′-dimethylbenzhydryl) amino, (4,4′-dimethylbenzhydryl) amino, (2,2 ′ -Dimethoxybenzhydryl) amino, (2,3′-dimethoxybenzhydryl)
Amino, (2,4'-dimethoxybenzhydryl) amino, (3,3'-dimethoxybenzhydryl) amino,
(3,4'-dimethoxybenzhydryl) amino,
(4,4'-dimethoxybenzhydryl) amino,
(2,2'-difluorobenzhydryl) amino,
(2,3'-difluorobenzhydryl) amino,
(2,4'-difluorobenzhydryl) amino,
(3,3′-difluorobenzhydryl) amino,
(3,4'-difluorobenzhydryl) amino,
(4,4'-difluorobenzhydryl) amino,
(2,2'-dihydroxybenzhydryl) amino,
(2,3'-dihydroxybenzhydryl) amino,
(2,4'-dihydroxybenzhydryl) amino,
(3,3'-dihydroxybenzhydryl) amino,
(3,4'-dihydroxybenzhydryl) amino,
(4,4'-dihydroxybenzhydryl) amino,
(2-Methylbenzhydryl) amino, (3-methylbenzhydryl) amino, (4-methylbenzhydryl)
Amino, (2-methoxybenzhydryl) amino, (3
-Methoxybenzhydryl) amino, (4-methoxybenzhydryl) amino, (2-fluorobenzhydryl) amino, (3-fluorobenzhydryl) amino,
(4-Fluorobenzhydryl) amino, (2-chlorobenzhydryl) amino, (3-chlorobenzhydryl) amino, (4-chlorobenzhydryl) amino,
(2-hydroxybenzhydryl) amino, (3-hydroxybenzhydryl) amino, (4-hydroxybenzhydryl) amino, (1,1-diphenylethyl) amino, (1,2-diphenylethyl) amino, [2-
(2-Fluorophenyl) -1-phenylethyl] amino, [2- (3-fluorophenyl) -1-phenylethyl] amino, [2- (4-fluorophenyl) -1-
Phenylethyl] amino, [2- (2-chlorophenyl) -1-phenylethyl] amino, [2- (3-chlorophenyl) -1-phenylethyl] amino, [2-
(4-Chlorophenyl) -1-phenylethyl] amino, [2- (2-methylphenyl) -1-phenylethyl] amino, [2- (3-methylphenyl) -1-phenylethyl] amino, [2- (4-methylphenyl)-
1-phenylethyl] amino, [2- (2-methoxyphenyl) -1-phenylethyl] amino, [2- (3-
Methoxyphenyl) -1-phenylethyl] amino,
[2- (4-Methoxyphenyl) -1-phenylethyl] amino, [1- (2-fluorophenyl) -2-
(2-Fluorophenyl) ethyl] amino, [1- (2
-Fluorophenyl) -2- (3-fluorophenyl)
Ethyl] amino, [1- (2-fluorophenyl) -2
-(4-Fluorophenyl) ethyl] amino, [1-
(3-Fluorophenyl) -2- (2-fluorophenyl) ethyl] amino, [1- (3-fluorophenyl)
-2- (3-Fluorophenyl) ethyl] amino, [1
-(3-fluorophenyl) -2- (4-fluorophenyl) ethyl] amino, [1- (4-fluorophenyl) -2- (2-fluorophenyl) ethyl] amino,
[1- (4-Fluorophenyl) -2- (3-fluorophenyl) ethyl] amino, [1- (4-fluorophenyl) -2- (4-fluorophenyl) ethyl] amino, [1- (2- Chlorophenyl) -2- (2-chlorophenyl) ethyl] amino, [1- (2-chlorophenyl) -2- (3-chlorophenyl) ethyl] amino,
[1- (2-chlorophenyl) -2- (4-chlorophenyl) ethyl] amino, [1- (3-chlorophenyl)]
-2- (2-chlorophenyl) ethyl] amino, [1-
(3-chlorophenyl) -2- (3-chlorophenyl)
Ethyl] amino, [1- (3-chlorophenyl) -2-
(4-chlorophenyl) ethyl] amino, [1- (4-
Chlorophenyl) -2- (2-chlorophenyl) ethyl] amino, [1- (4-chlorophenyl) -2- (3
-Chlorophenyl) ethyl] amino, [1- (4-chlorophenyl) -2- (4-chlorophenyl) ethyl] amino, [1- (2-chlorophenyl) -2- (2-methoxyphenyl) ethyl] amino, [1 -(2-chlorophenyl) -2- (3-methoxyphenyl) ethyl] amino, [1- (2-chlorophenyl) -2- (4-methoxyphenyl) ethyl] amino, [1- (3-chlorophenyl) -2 -(2-Methoxyphenyl) ethyl] amino, [1- (3-chlorophenyl) -2- (3-methoxyphenyl) ethyl] amino, [1- (3-chlorophenyl) -2- (4-methoxyphenyl) ethyl ] Amino, [1- (4-chlorophenyl) -2- (2-methoxyphenyl) ethyl] amino, [1- (4-chlorophenyl) -2- (3-me Kishifeniru) ethyl] amino, [1- (4-chlorophenyl) -2- (4-methoxyphenyl) ethyl] amino, [1- (2-methylphenyl) -2- (2-methylphenyl) ethyl] amino,
[1- (2-Methylphenyl) -2- (3-methylphenyl) ethyl] amino, [1- (2-methylphenyl)]
-2- (4-methylphenyl) ethyl] amino, [1-
(3-Methylphenyl) -2- (2-methylphenyl)
Ethyl] amino, [1- (3-methylphenyl) -2-
(3-Methylphenyl) ethyl] amino, [1- (3-
Methylphenyl) -2- (4-methylphenyl) ethyl] amino, [1- (4-methylphenyl) -2- (2
-Methylphenyl) ethyl] amino, [1- (4-methylphenyl) -2- (3-methylphenyl) ethyl] amino, [1- (4-methylphenyl) -2- (4-methylphenyl) ethyl] Amino, [1- (2-hydroxyphenyl) -2- (2-hydroxyphenyl) ethyl]
Amino, [1- (2-hydroxyphenyl) -2- (3
-Hydroxyphenyl) ethyl] amino, [1- (2-
Hydroxyphenyl) -2- (4-hydroxyphenyl) ethyl] amino, [1- (3-hydroxyphenyl) -2- (2-hydroxyphenyl) ethyl] amino, [1- (3-hydroxyphenyl) -2- (3-Hydroxyphenyl) ethyl] amino, [1- (3-hydroxyphenyl) -2- (4-hydroxyphenyl) ethyl] amino, [1- (4-hydroxyphenyl) -2
-(2-hydroxyphenyl) ethyl] amino, [1-
(4-Hydroxyphenyl) -2- (3-hydroxyphenyl) ethyl] amino, [1- (4-hydroxyphenyl) -2- (4-hydroxyphenyl) ethyl] amino, [2- (2-fluorophenyl) -1- (2-Methylphenyl) ethyl] amino, [2- (2-fluorophenyl) -1- (3-methylphenyl) ethyl] amino, [2- (2-fluorophenyl) -1- (4- Methylphenyl) ethyl] amino, [2- (3-fluorophenyl) -1- (2-methylphenyl) ethyl] amino, [2- (3-fluorophenyl) -1- (3-methylphenyl) ethyl] amino , [2- (3-Fluorophenyl) -1- (4-methylphenyl) ethyl] amino, [2- (4-fluorophenyl) -1- (2-methylphenyl) ethyl] a No, [2- (4-fluorophenyl) -1- (3-methylphenyl) ethyl] amino, [2- (4-fluorophenyl) -1- (4-methylphenyl) ethyl] amino, 2- (2 -Fluorophenyl) -1- (2-methoxyphenyl) ethyl] amino, 2- (2-fluorophenyl) -1- (3-methoxyphenyl) ethyl] amino, 2- (2-fluorophenyl) -1- ( 4-methoxyphenyl) ethyl] amino, 2- (3-fluorophenyl) -1- (2-methoxyphenyl) ethyl] amino, 2- (3-fluorophenyl) -1- (3-methoxyphenyl) ethyl] amino , 2- (3-fluorophenyl) -1- (4-methoxyphenyl) ethyl] amino, 2- (4-fluorophenyl) -1- (2-methoxyphenyl) ethyl] a No, 2- (4-fluorophenyl) -1- (3-methoxyphenyl) ethyl] amino, 2- (4-fluorophenyl) -1- (4-methoxyphenyl) ethyl] amino, [2- (2- Hydroxyphenyl) -1-phenylethyl] amino, [2- (3-hydroxyphenyl)-
1-phenylethyl] amino, [2- (4-hydroxyphenyl) -1-phenylethyl] amino, [1- (2
-Methoxyphenyl) -2-phenylethyl] amino,
[1- (3-Methoxyphenyl) -2-phenylethyl] amino, [1- (4-methoxyphenyl) -2-phenylethyl] amino, (1-methyl-1,2-diphenylethyl) amino, (2 , 2-diphenylethyl) amino, (1,1-diphenylethyl) amino, [1-
(2-Fluorophenyl) -1- (2-fluorophenyl) ethyl] amino, [1- (2-fluorophenyl)]
-1- (3-fluorophenyl) ethyl] amino, [1
-(2-fluorophenyl) -1- (4-fluorophenyl) ethyl] amino, [1- (3-fluorophenyl) -1- (3-fluorophenyl) ethyl] amino,
[1- (3-Fluorophenyl) -1- (4-fluorophenyl) ethyl] amino, [1- (4-fluorophenyl) -1- (4-fluorophenyl) ethyl] amino, [1- (2- Methylphenyl) -1- (2-methylphenyl) ethyl] amino, [1- (2-methylphenyl) -1- (3-methylphenyl) ethyl] amino,
[1- (2-Methylphenyl) -1- (4-methylphenyl) ethyl] amino, [1- (3-methylphenyl)]
-1- (3-methylphenyl) ethyl] amino, [1-
(3-Methylphenyl) -1- (4-methylphenyl)
Ethyl] amino, [1- (4-methylphenyl) -1-
(4-Methylphenyl) ethyl] amino, [1- (2-
Methoxyphenyl) -1- (2-methoxyphenyl) ethyl] amino, [1- (2-methoxyphenyl) -1-
(3-Methoxyphenyl) ethyl] amino, [1- (2
-Methoxyphenyl) -1- (4-methoxyphenyl)
Ethyl] amino, [1- (3-methoxyphenyl) -1
-(3-Methoxyphenyl) ethyl] amino, [1-
(3-Methoxyphenyl) -1- (4-methoxyphenyl) ethyl] amino, [1- (4-methoxyphenyl)]
-1- (4-methoxyphenyl) ethyl] amino, [1
-(2-Hydroxyphenyl) -1-phenylethyl]
Amino, [1- (3-hydroxyphenyl) -1-phenylethyl] amino, [1- (4-hydroxyphenyl) -1-phenylethyl] amino, tritylamino,
(1-benzyl-2-phenylethyl) amino, (1-
Benzyl-1-methyl-2-phenylethyl) amino,
[Bis (2-furyl) methyl] amino, [bis (3-furyl) methyl] amino, [bis (2-thienyl) methyl] amino, [bis (3-thienyl) methyl] amino,
[1,1-bis (2-thienyl) ethyl] amino,
[1,1-bis (3-thienyl) ethyl] amino,
[(2-Methyl-3-thienylmethyl), (2-methyl-3-thienylmethyl)] amino, [(2-methyl-3
-Thienylmethyl), (5-methyl-2-thienylmethyl)] amino, [(2-methyl-3-thienylmethyl), (5-methyl-3-thienylmethyl)] amino,
[(5-Methyl-2-thienylmethyl), (5-methyl-2-thienylmethyl)] amino, [(5-methyl-2
-Thienylmethyl), (5-methyl-3-thienylmethyl)] amino, [(5-methyl-3-thienylmethyl)], (5-methyl-3-thienylmethyl)] amino,
[1- (2-thienyl) -1-methylethyl] amino,
[1- (3-thienyl) -1-methylethyl] amino,
[1- (2-Methyl-3-thienyl) -1-methylethyl] amino, [1- (5-methyl-2-thienyl) -1
-Methylethyl] amino, [1- (5-methyl-3-thienyl) -1-methylethyl] amino, [1- (2-furyl) -1-methylethyl] amino, [1- (3-furyl)] -1-Methylethyl] amino, [1- (2-methyl-3-furyl) -1-methylethyl] amino, [1-
(5-Methyl-2-furyl) -1-methylethyl] amino, [1- (5-methyl-3-furyl) -1-methylethyl] amino, [1- (2-furyl) -2- (2 -Furyl) ethyl] amino, [1- (2-furyl) -2- (3
-Furyl) ethyl] amino, [1- (3-furyl) -2
-(2-furyl) ethyl] amino, [1- (3-furyl) -2- (3-furyl) ethyl] amino, [1- (2
-Thienyl) -2- (2-thienyl) ethyl] amino,
[1- (2-thienyl) -2- (3-thienyl) ethyl] amino, [1- (3-thienyl) -2- (2-thienyl) ethyl] amino, [1- (3-thienyl) -2. −
(3-thienyl) ethyl] amino, [1- (2-furyl) -2-phenylethyl] amino, [1- (3-furyl) -2-phenylethyl] amino, [2-phenyl-
1- (2-thienyl) ethyl] amino, [2-phenyl-1- (3-thienyl) ethyl] amino, [1-phenyl-2- (2-thienyl) ethyl] amino, [1-phenyl-2- (3-thienyl) ethyl] amino, [2-
(2-Methylphenyl) -1- (2-thienyl) ethyl] amino, [2- (3-methylphenyl) -1- (2
-Thienyl) ethyl] amino, [2- (4-methylphenyl) -1- (2-thienyl) ethyl] amino, [2-
(2-Methylphenyl) -1- (3-thienyl) ethyl] amino, [2- (3-methylphenyl) -1- (3
-Thienyl) ethyl] amino, [2- (4-methylphenyl) -1- (3-thienyl) ethyl] amino, [2-
(2-Chlorophenyl) -1- (2-thienyl) ethyl] amino, [2- (3-chlorophenyl) -1- (2
-Thienyl) ethyl] amino, [2- (4-chlorophenyl) -1- (2-thienyl) ethyl] amino, [2-
(2-Chlorophenyl) -1- (3-thienyl) ethyl] amino, [2- (3-chlorophenyl) -1- (3
-Thienyl) ethyl] amino, [2- (4-chlorophenyl) -1- (3-thienyl) ethyl] amino, [2-
(2-Fluorophenyl) -1- (2-thienyl) ethyl] amino, [2- (3-fluorophenyl) -1-
(2-thienyl) ethyl] amino, [2- (4-fluorophenyl) -1- (2-thienyl) ethyl] amino,
[2- (2-fluorophenyl) -1- (3-thienyl) ethyl] amino, [2- (3-fluorophenyl)
-1- (3-thienyl) ethyl] amino, [2- (4-
Fluorophenyl) -1- (3-thienyl) ethyl] amino, [2- (2-methoxyphenyl) -1- (2-thienyl) ethyl] amino, [2- (3-methoxyphenyl) -1- (2 -Thienyl) ethyl] amino, [2-
(4-Methoxyphenyl) -1- (2-thienyl) ethyl] amino, [2- (2-methoxyphenyl) -1-
(3-thienyl) ethyl] amino, [2- (3-methoxyphenyl) -1- (3-thienyl) ethyl] amino,
[2- (4-Methoxyphenyl) -1- (3-thienyl) ethyl] amino, [1- (2-fluorophenyl)
-2- (2-thienyl) ethyl] amino, [1- (3-
Fluorophenyl) -2- (2-thienyl) ethyl] amino, [1- (4-fluorophenyl) -2- (2-thienyl) ethyl] amino, [1- (2-fluorophenyl) -2- (3 -Thienyl) ethyl] amino, [1-
(3-Fluorophenyl) -2- (3-thienyl) ethyl] amino, [1- (4-fluorophenyl) -2-
(3-thienyl) ethyl] amino, cyclopentylmethylamino, cyclohexylmethylamino, allylamino, cyclopentylamino, cyclohexylamino,
N, N-dimethylamino, N, N-diethylamino, N
-Benzyl-N-methylamino, N-benzyl-N-ethylamino, N-benzyl-N-isopropylamino,
N-benzyl-N-isobutylamino, N-benzyl-
Nt-butylamino, N- (2-fluorobenzyl)
-N-isopropylamino, N- (3-fluorobenzyl) -N-isopropylamino, N- (4-fluorobenzyl) -N-isopropylamino, N- (2-chlorobenzyl) -N-isopropylamino, N- (3-chlorobenzyl) -N-isopropylamino, N- (4-chlorobenzyl) -N-isopropylamino, N- (2-
Methylbenzyl) -N-isopropylamino, N- (3
-Methylbenzyl) -N-isopropylamino, N-
(4-methylbenzyl) -N-isopropylamino, N
-(2-Methoxybenzyl) -N-isopropylamino, N- (3-methoxybenzyl) -N-isopropylamino, N- (4-methoxybenzyl) -N-isopropylamino, N- (2-hydroxybenzyl)- N-isopropylamino, N- (3-hydroxybenzyl)-
N-isopropylamino, N- (4-hydroxybenzyl) -N-isopropylamino, N, N-dibenzylamino, N-benzyl-N- (2-methoxybenzyl) amino, N-benzyl-N- (3- Methoxybenzyl) amino, N-benzyl-N- (4-methoxybenzyl) amino, N- (2-fluorobenzyl) -N- (2-fluorobenzyl) amino, N- (2-fluorobenzyl)
-N- (3-fluorobenzyl) amino, N- (2-fluorobenzyl) -N- (4-fluorobenzyl) amino, N- (3-fluorobenzyl) -N- (3-fluorobenzyl) amino, N -(3-Fluorobenzyl)-
N- (4-fluorobenzyl) amino, N- (4-fluorobenzyl) -N- (4-fluorobenzyl) amino, N- (2-methylbenzyl) -N- (2-methylbenzyl) amino, N- (2-methylbenzyl) -N-
(3-Methylbenzyl) amino, N- (2-methylbenzyl) -N- (4-methylbenzyl) amino, N- (3
-Methylbenzyl) -N- (3-methylbenzyl) amino, N- (3-methylbenzyl) -N- (4-methylbenzyl) amino, N- (4-methylbenzyl) -N-
(4-Methylbenzyl) amino, N- (2-methoxybenzyl) -N- (2-methoxybenzyl) amino, N-
(2-Methoxybenzyl) -N- (3-methoxybenzyl) amino, N- (2-methoxybenzyl) -N- (4
-Methoxybenzyl) amino, N- (3-methoxybenzyl) -N- (3-methoxybenzyl) amino, N-
(3-Methoxybenzyl) -N- (4-methoxybenzyl) amino, N- (4-methoxybenzyl) -N- (4
-Methoxybenzyl) amino, N- (2-hydroxybenzyl) -N- (2-hydroxybenzyl) amino, N
-(2-hydroxybenzyl) -N- (3-hydroxybenzyl) amino, N- (2-hydroxybenzyl)-
N- (4-hydroxybenzyl) amino, N- (3-hydroxybenzyl) -N- (3-hydroxybenzyl)
Amino, N- (3-hydroxybenzyl) -N- (4-
Hydroxybenzyl) amino, N- (4-hydroxybenzyl) -N- (4-hydroxybenzyl) amino, N
-(2-thienylmethyl) -N- (2-thienylmethyl) amino, N- (2-thienylmethyl) -N- (3-
And a N- (3-thienylmethyl) -N- (3-thienylmethyl) amino group.

Particularly preferably, t-butylamino, (1-
Methyl-1-phenylethyl) amino, [1-methyl-
1- (2-methylphenyl) ethyl] amino, [1-methyl-1- (3-methylphenyl) ethyl] amino,
[1-Methyl-1- (4-methylphenyl) ethyl] amino, [1-methyl-1- (2-methoxyphenyl) ethyl] amino, [1-methyl-1- (3-methoxyphenyl) ethyl] amino , [1-methyl-1- (4-methoxyphenyl) ethyl] amino, [1-methyl-1-
(2-ethoxyphenyl) ethyl] amino, [1-methyl-1- (3-ethoxyphenyl) ethyl] amino,
[1-Methyl-1- (4-ethoxyphenyl) ethyl]
Amino, [1-methyl-1- (2-fluorophenyl)
Ethyl] amino, [1-methyl-1- (3-fluorophenyl) ethyl] amino, [1-methyl-1- (4-fluorophenyl) ethyl] amino, [1-methyl-1-
(2-Chlorophenyl) ethyl] amino, [1-methyl-1- (3-chlorophenyl) ethyl] amino, [1-
Methyl-1- (4-chlorophenyl) ethyl] amino,
(1,1-Dimethyl-2-phenylethyl) amino, benzhydrylamino, (2,2′-dimethoxybenzhydryl) amino, (2,3′-dimethoxybenzhydryl) amino, (2,4 ′) -Dimethoxybenzhydryl)
Amino, (3,3′-dimethoxybenzhydryl) amino, (3,4′-dimethoxybenzhydryl) amino,
(4,4'-dimethoxybenzhydryl) amino,
(2,2'-difluorobenzhydryl) amino,
(2,3'-difluorobenzhydryl) amino,
(2,4'-difluorobenzhydryl) amino,
(3,3′-difluorobenzhydryl) amino,
(3,4'-difluorobenzhydryl) amino,
(4,4'-difluorobenzhydryl) amino, (2
-Methoxybenzhydryl) amino, (3-methoxybenzhydryl) amino, (4-methoxybenzhydryl) amino, (2-fluorobenzhydryl) amino,
(3-Fluorobenzhydryl) amino, (4-fluorobenzhydryl) amino, (2-chlorobenzhydryl) amino, (3-chlorobenzhydryl) amino,
(4-chlorobenzhydryl) amino, (2-hydroxybenzhydryl) amino, (3-hydroxybenzhydryl) amino, (4-hydroxybenzhydryl) amino, (1,1-diphenylethyl) amino, (1, 2,
-Diphenylethyl) amino, [2- (2-chlorophenyl) -1-phenylethyl] amino, [2- (3-chlorophenyl) -1-phenylethyl] amino, [2-
(4-Chlorophenyl) -1-phenylethyl] amino, [2- (2-fluorophenyl) -1-phenylethyl] amino, [2- (3-fluorophenyl) -1-
Phenylethyl] amino, [2- (4-fluorophenyl) -1-phenylethyl] amino, [2- (2-methylphenyl) -1-phenylethyl] amino, [2-
(3-Methylphenyl) -1-phenylethyl] amino, [2- (4-methylphenyl) -1-phenylethyl] amino, [2- (2-methoxyphenyl) -1-phenylethyl] amino, [2 -(3-Methoxyphenyl) -1-phenylethyl] amino, [2- (4-methoxyphenyl) -1-phenylethyl] amino, [1-
(2-thienyl) -1- (2-thienyl) methyl] amino, [1- (2-thienyl) -1- (3-thienyl) methyl] amino, [1- (3-thienyl) -1- (3 -Thienyl) methyl] amino, [2-phenyl-1- (2-
Thienyl) ethyl] amino, [2-phenyl-1- (3
-Thienyl) ethyl] amino, [1-methyl-1- (2
-Thienyl) ethyl] amino, [1-methyl-1- (3
-Thienyl) ethyl] amino, [1-methyl-1- (2
-Methyl-3-thienyl) ethyl] amino, [1-methyl-1- (5-methyl-2-thienyl) ethyl] amino, [1-methyl-1- (5-methyl-3-thienyl)]
Ethyl] amino, [1-methyl-1- (2-furylethyl] amino, [1-methyl-1- (3-furylethyl]]
Amino, N, N-dimethylamino, N, N-diethylamino, N, N-dibenzylamino, N- (2-fluorobenzyl) -N- (2-fluorobenzyl) amino, N
-(2-Fluorobenzyl) -N- (3-fluorobenzyl) amino, N- (2-fluorobenzyl) -N-
(4-Fluorobenzyl) amino, N- (3-fluorobenzyl) -N- (3-fluorobenzyl) amino, N
-(3-Fluorobenzyl) -N- (4-fluorobenzyl) amino, N- (4-fluorobenzyl) -N-
(4-Fluorobenzyl) amino, N- (2-methylbenzyl) -N- (2-methylbenzyl) amino, N-
(2-Methylbenzyl) -N- (3-methylbenzyl)
Amino, N- (2-methylbenzyl) -N- (4-methylbenzyl) amino, N- (3-methylbenzyl) -N
-(3-Methylbenzyl) amino N- (3-methylbenzyl) -N- (4-methylbenzyl) amino, N- (4
-Methylbenzyl) -N- (4-methylbenzyl) amino, N- (2-methoxybenzyl) -N- (2-methoxybenzyl) amino, N- (2-methoxybenzyl)-
N- (3-methoxybenzyl) amino, N- (2-methoxybenzyl) -N- (4-methoxybenzyl) amino, N- (3-methoxybenzyl) -N- (3-methoxybenzyl) amino, N- (3-methoxybenzyl)-
It is an N- (4-methoxybenzyl) amino or N- (4-methoxybenzyl) -N- (4-methoxybenzyl) amino group.

In compounds (I) and (II), optical isomers based on asymmetric carbon atoms exist, but such stereoisomers and mixtures thereof are also included in the present application.

The compound (IVa) is preferably methanesulfonic acid chloride, methanesulfonic acid bromide, ethanesulfonic acid chloride, propanesulfonic acid chloride, benzenesulfonic acid chloride, toluenesulfonic acid chloride, 2,4,6-trimethyl. Benzenesulfonic acid chloride, chlorobenzenesulfonic acid chloride, bromobenzenesulfonic acid chloride, methoxybenzenesulfonic acid chloride, trifluoromethanesulfonyl chloride,
2,4,6-triisopropylbenzenesulfonyl chloride, camphorsulfonic acid chloride or chlorosulfonylisocyanate, more preferably methanesulfonic acid chloride, benzenesulfonic acid chloride, toluenesulfonic acid chloride, 2,4,6-tricarboxylic acid. Isopropylbenzenesulfonyl chloride, camphorsulfonic acid chloride or chlorosulfonyl isocyanate.

The compound (IVb) is preferably methanesulfonic anhydride, trifluoromethanesulfonic anhydride, ethanesulfonic anhydride, benzenesulfonic anhydride, toluenesulfonic anhydride, chlorobenzenesulfonic anhydride or Camphor sulfonic acid anhydride, more preferably methane sulfonic acid anhydride, trifluoromethane sulfonic acid anhydride, benzene sulfonic acid anhydride or toluene sulfonic acid anhydride.

The base used is, for example, triethylamine, tripropylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline,
N, N-diethylaniline, pyridine, 4- (N, N-
Dimethylamino) pyridine, quinoline, 1,5-diazabicyclo [4.3.0] non-5-ene (DBN),
1,8-diazabicyclo [5.4.0] undec-7-
An organic amine such as ene (DBU), preferably
Triethylamine, N, N-diethylaniline, 4-
(N, N-dimethylamino) pyridine and pyridine. Also, two or more amines can be used simultaneously.

The reaction is preferably carried out in an inert solvent,
Examples of the solvent used include hydrocarbons such as hexane, benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane, ethers such as ether, tetrahydrofuran, dioxane and dimethoxyethane. , Amides such as dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide, and sulfoxides such as dimethylsulfoxide, and preferably halogenated hydrocarbons. Further, a liquid amine such as triethylamine or pyridine can also be used in a large excess as a solvent.

The reaction temperature will differ depending on the starting compounds used, the type of base used, etc., but is usually -70 ° C to 100 ° C, preferably -50 ° C to 50 ° C, and the time required for the reaction is Although it varies depending on the reaction temperature and the like, it is usually 15 minutes to 20 hours, and preferably 30 minutes to 10 hours.

Further, in this reaction, more preferably, the compound (I) and 1 to 10 equivalents of a base are added to an inert solvent,
Then, 1 to 5 equivalents of compound (IVa) or (IV
b) and then 1 to 5 equivalents of compound (III) for reaction, or the reaction of compound (I) in an inert solvent.
And 1 to 10 equivalents of a base, then 1 to 5 equivalents of compound (III), and 1 to 5 equivalents of compound (IVa) or (IVb) are added and reacted.

After completion of the reaction, the desired compound (II) is collected from the reaction mixture according to a conventional method. For example, water is added to the reaction mixture and the mixture is extracted with a water-immiscible organic solvent, or the reaction mixture is diluted with a water-immiscible organic solvent, and the obtained extract or diluent is water, diluted hydrochloric acid solution and diluted sodium bicarbonate Wash with water,
After drying, the target product can be obtained by distilling off the solvent. Further, if desired, it can be purified by a conventional method, for example, recrystallization, reprecipitation, column chromatography and the like.

Even if a Vilsmeier reagent such as dimethylformamide-phosphorus oxychloride or chloromethylenedimethyliminium chloride is used in place of the compound (IVa) or (IVb), the corresponding amide is obtained by the same reaction as described above. The body is obtained. At this time, preferably, the compound (I) and 1 to 5 equivalents of Vilsmeier reagent are added to an inert solvent, and then 1 to 10 equivalents of the base and 1
It is carried out by adding 5 to 5 equivalents of compound (III) and reacting.

In the starting compound (I) of the present invention,
Compounds in which A is the general formula (I-1) are known or
For example, J. Med. Chem., 27, 1690 (1984)
Compound), which is produced according to the method described in Vol. 29, p. 2298 (1986), and A is the general formula (I-2) is known, for example, European Patent Publication No. 465123 or European Patent Publication No. 46514
1 is produced according to the method described in No. 1 and A is represented by the general formula (I-
The compounds 3) are known or are prepared according to the methods described, for example, in EP 517047 or EP 509259.

[0039]

INDUSTRIAL APPLICABILITY According to the method for producing steroid-17-amides of the present invention, by reacting a carboxylic acid compound with an amine compound in the presence of a sulfonyl compound, a good yield can be obtained, a simple operation can be carried out, and the drug itself or This is a method for producing a steroid-17-amide compound (II) as an intermediate thereof, which is an industrially useful method.

In the compound (II), the compound in which the bond at the 1- and 2-position is a single bond can be prepared by a known method (for example, European Patent Publication No. 484094, JP-A-4-4094).
No. 261,194, JP-A-4-261195, etc.) and can be dehydrogenated to give the corresponding compound.

Next, the present invention will be described more specifically with reference to Examples and Reference Examples.

[0042]

Example 1 N- [1- (4-methoxyphenyl) -1-methylethyl
Lu-4-aza-3-oxoandrostane-17β-ca
Ruboxamide 4-aza-3- oxoandrostane -17β-carboxylic acid 100 mg, catalytic amount of 4-dimethylaminopyridine and 0.131 ml of triethylamine were added to methylene chloride 4
This was dissolved in ml, 103 mg of 1- (4-methoxyphenyl) -1-methylethylamine was added, and 89.6 mg of p-toluenesulfonyl chloride was added every 30 minutes while stirring at room temperature. After adding p-toluenesulfonyl chloride, the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with methylene chloride, 1N-hydrochloric acid, water,
The extract was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluting solvent: acetone / methylene chloride = 2 / 98-30 / 70), and 1
39 mg of the crystalline target compound was obtained (94% yield). NMR spectrum (CDCl ₃ ) δppm: 0.68 (3H, s), 0.90 (3
H, s), 0.70-2.80 (20H, m), 1.69 (3H, s), 1.71 (3H, s), 3.0
8 (1H, dd, J = 13,4Hz), 3.80 (3H, s), 5.49 (1H, br.s), 6.25
(1H, br.s), 6.88 (2H, d, J = 9Hz), 7.30 (2H, d, J = 9Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2939, 1701,
1674, 1615, 1514, 1497, 1455, 1360, 1251, 1180, 10
34, 827

[0043]

Example 2 N- [1- (4-ethoxyphenyl) -1-methylethyl
]]-3-oxo-4-aza-5α-androstane
17β-Carboxamide 3-oxo-4-aza-5α-androstane-17β
Using -carboxylic acid and 1- (4-ethoxyphenyl) -1-methylethylamine, the target compound was obtained in a yield of 40% by the same method as in Example 1. NMR spectrum (CDCl ₃ ) δppm: 0.67 (3H, s), 0.75-
2.50 (20H, m), 0.91 (3H, s), 1.40 (3H, t, J = 7Hz), 1.69 (3
H, s), 1.71 (3H, s), 3.06 (1H, dd, J = 4.4,11Hz), 4.02 (2H,
q, J = 7Hz), 5.47 (1H, s), 5.72 (1H, s), 6.84 (2H, d, J = 8.8H
z), 7.32 (2H, d, J = 8.8Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3195, 2971,
2939, 1700, 1674, 1612, 1512

[0044]

Example 3 N- [1- (2-methoxyphenyl) -1-methylethyl
]]-3-oxo-4-aza-5α-androstane
17β-Carboxamide 3-oxo-4-aza-5α-androstane-17β
Using -carboxylic acid and 1- (2-methoxyphenyl) -1-methylethylamine, the target compound was obtained with a yield of 62% by the same method as in Example 1. NMR spectrum (CDCl ₃ ) δppm: 0.63 (3H, s), 0.74-
2.46 (20H, m), 0.90 (3H, s), 1.76 (3H, s), 1.80 (3H, s), 3.
06 (1H, dd, J = 4.6,11Hz), 3.82 (3H, s), 5.70 (1H, s), 5.91
(1H, s), 6.86-6.97 (2H, m), 7.19-7.26 (1H, m), 7.37-7.4
2 (1H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3199, 2939,
1680, 1666, 1505, 1490

[0045]

Example 4 N- [1- (4-methylphenyl) -1-methylethyl
]]-3-oxo-4-aza-5α-androstane
17β-Carboxamide 3-oxo-4-aza-5α-androstane-17β
Using carboxylic acid and 1- (4-methylphenyl) -1-methylethylamine, in the same manner as in Example 1,
The target compound was obtained with a yield of 31%. NMR spectrum (CDCl ₃ ) δppm: 0.68 (3H, s), 0.78-
2.45 (20H, m), 0.91 (3H, s), 1.69 (3H, s), 1.71 (3H, s),
2.32 (3H, s), 3.06 (1H, dd, J = 4.6,11Hz), 5.50 (1H, br.s),
7.13 (2H, d, J = 8Hz), 7.30 (2H, d, J = 8Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3198, 2970,
2940, 1701, 1674, 1498

[0046]

Example 5 N- [1- (2-thienyl) -1-methylethyl] -3
-Oxo-4-aza-5α-androstane-17β-
Carboxamide 3-oxo-4-aza-5α-androstane-17β
-Carboxylic acid and 1- (2-thienyl) -1-methylethylamine were used to give a yield of 3 by the same method as in Example 1.
The target compound was obtained at 3%. NMR spectrum (CDCl ₃ ) δppm: 0.67 (3H, s), 0.90 (3
H, s), 0.70-2.35 (18H, m), 1.81 (3H, s), 1.82 (3H, s), 2.3
9-2.45 (2H, m), 3.06 (1H, dd, J = 11,4Hz), 5.51 (1H, br.s),
5.78 (1H, br.s), 6.91-6.99 (2H, m), 7.17 (1H, dd, J = 5,2H
z) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3296, 2937,
1663, 1449, 1360, 695

[0047]

Example 6 N- [4,4′-dimethoxydiphenylmethyl) -3-
Oxo-4-aza-5α-androstane-17β-ca
Ruboxamide 3-oxo-4-aza-5α-androstane-17β
-Carboxylic acid and 4,4'-dimethoxybenzhydrylamine were used, and the yield was 88% by the same method as in Example 1.
The desired compound was obtained in. NMR spectrum (CDCl ₃ ) δppm: 0.67 (3H, s), 0.89 (3
H, s), 0.70-2.35 (18H, m), 2.37-2.43 (2H, m), 3.04 (1H, d
d, J = 11,4Hz), 3.78 (3H, s), 3.79 (3H, s), 5.54 (1H, br.
s), 5.79 (1H, d, J = 8Hz), 6.17 (1H, d, J = 8Hz), 6.82-6.88
(4H, m), 7.10-7.16 (4H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3305, 2936,
1659, 1511, 1247, 1175, 1034, 830

[0048]

Example 7 N- [α- (4-chlorophenyl) benzyl] -3-o
Xo-4-aza-5α-androstane-17β-cal
Voxamide 3-oxo-4-aza-5α-androstane-17β
-Carboxylic acid and α- (4-chlorophenyl) benzylamine were used and the yield was 93% by the same method as in Example 1.
The desired compound was obtained in. NMR spectrum (CDCl ₃ ) δppm: 0.66 and 0.67 (total 3
H, each s), 0.89 and 0.90 (total 3H, each s), 0.73-2.45 (20H,
m), 3.05 (1H, dd, J = 11,4Hz), 5.84 (1H, d, J = 8Hz), 5.88 (1
H, br.s), 6.22 and 6.25 (total 1H, each d, J = 8Hz), 7.13-7.3
7 (9H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3360, 2978,
1736, 1652, 1514, 1371, 1199

[0049]

Example 8 Nt-butyl-3-oxo-4-aza-5α-and
Lost-1-ene-17β-carboxamide 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid and t-butylamine were reacted in the same manner as in Example 1, and acetone was added. Crystallization was carried out to obtain the target compound with a yield of 90%. NMR spectrum (CDCl ₃ ) δppm: 0.70 (3H, s), 0.98 (3
H, s), 0.10-2.15 (16H, m), 1.35 (9H, s), 3.33 (1H, t, J = 8H
z), 5.07 (1H, br.s), 5.49 (1H, br.s), 5.82 (1H, d, J = 10H
z), 6.79 (1H, d, J = 10Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3213, 2940,
1679, 1600, 1501, 1451, 1346, 819

[0050]

Example 9 Nt-Butyl-3-oxo-4-aza-5α-and
Rostan-17β-carboxamide 3-oxo-4-aza-5α-androstan-17β
-A carboxylic acid and t-butylamine were reacted in the same manner as in Example 1, and the residue was crystallized with acetone to obtain the target compound with a yield of 74%. NMR spectrum (CDCl ₃ ) δppm: 0.69 (3H, s), 0.91 (3
H, s), 0.75-2.50 (20H, m), 1.35 (9H, s), 3.10 (1H, dd, J = 1
3,4Hz), 5.07 (1H, br.s), 6.26 (1H, br.s) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2939, 1698,
1670, 1502, 1452, 1367, 1360, 1308, 1227

[0051]

Example 10 N-diphenylmethyl-3-oxo-4-aza-5α-
Androstan-17β-carboxamide 3-oxo-4-aza-5α-androstan-17β
Using carboxylic acid and diphenylmethylamine, the target compound was obtained in a yield of 91% by the same method as in Example 1. NMR spectrum (CDCl ₃ ) δppm: 0.67 (3H, s), 0.90 (3
H, s), 0.70-2.00 (15H, m), 2.15-2.30 (3H, m), 2.37-2.47
(2H, m), 3.03 (1H, dd, J = 10,5Hz), 5.46 (1H, br.s), 5.88 (1
H, d, J = 9Hz), 6.28 (1H, d, J = 9Hz), 7.20-7.38 (10H, m) infrared absorption spectrum ν _max cm ^-1 (KBr): 3288,
2935, 2868, 1664, 1521, 1
493, 1448, 1226, 733, 698

[0052]

Example 11 N- [α- (4-methoxyphenyl) benzyl] -3-
Oxo-4-aza-5α-androstane-17β-ca
Ruboxamide 3-oxo-4-aza-5α-androstane-17β
-Carboxylic acid and α- (4-methoxyphenyl) benzylamine were used, and the yield was 90% by the same method as in Example 1.
The desired compound was obtained in. NMR spectrum (CDCl ₃ ) δppm: 0.67 (3H,
s), 0.89 (3H, s), 0.70-2.70 (20H, m), 3.05 (1H, dd, J = 11,
4Hz), 5.68 (1H, br.s), 5.83 (1H, d, J = 7Hz), 6.22 (1H, d, J
= 7Hz), 6.82-6.88 (2H, m), 7.10-7.36 (7H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3304, 2935,
1664, 1511, 1248, 1033, 700

[0053]

Example 12 N- [bis (4-fluorophenyl) methyl] -3-o
Xo-4-aza-5α-androstane-17β-cal
Voxamide 3-oxo-4-aza-5α-androstane-17β
-A carboxylic acid and (4,4'-difluorodiphenyl) methylamine were reacted in the same manner as in Example 1, and the residue was crystallized with acetone to obtain the target compound with a yield of 91%. NMR spectrum (CDCl ₃ ) δppm: 0.66 (3H, s), 0.73-
2.42 (20H, m), 0.90 (3H, s), 3.03 (1H, dd, J = 12,5Hz), 5.5
4 (1H, s), 5.80 (1H, d, J = 8Hz), 6.24 (1H, d, J = 8Hz), 6.99-
7.32 (8H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2939, 2871,
1660, 1605, 1509, 1308, 1226, 1158, 834

[0054]

Example 13 N- [1- (3,4-dimethoxyphenyl) -1-methyi
Ruethyl] -3-oxo-4-aza-5α-andross
Tan-17β-carboxamide 3-oxo-4-aza-5α-androstane-17β
-Carboxylic acid and 1- (3,4-dimethoxyphenyl)-
The target compound was obtained with a yield of 44% by the same method as in Example 1 using 1-methylethylamine. NMR spectrum (CDCl ₃ ) δppm: 0.69 (3H, s), 0.91 (3
H, s), 0.75-2.20 (18H, m), 1.70 (3H, s), 1.72 (3H, s), 2.
40-2.52 (2H, m), 3.08 (1H, dd, J = 12,5Hz), 3.86 (3H, s),
3.87 (3H, s), 5.49 (1H, br.s), 6.34 (1H, br.s), 6.82 (1H,
d, J = 8Hz), 6.94 (1H, s), 6.95 (1H, d, J = 8Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2937, 1670,
1518, 1454, 1262, 1144, 1028

[0055]

Example 14 N- (1-methyl-1-phenylethyl) -3-oxo
-4-aza-5α-androstane-17β-carboxy
Samide 3-oxo-4-aza-5α-androstane-17β
Using -carboxylic acid and 1-methyl-1-phenylethylamine and in the same manner as in Example 1, the target compound was obtained in a yield of 55%. NMR spectrum (CDCl ₃ ) δppm: 0.68 (3H, s), 0.90 (3
H, s), 0.70-2.20 (18H, m), 1.70 (3H, s), 1.72 (3H, s), 2.
35-2.50 (2H, m), 3.06 (1H, dd, J = 12,5Hz), 5.52 (1H, br.
s), 5.60 (1H, br.s), 7.20-7.45 (5H, m) infrared absorption spectrum ν _max cm ^-1 (KBr): 2938, 2919,
1699, 1672, 1495, 1447, 1361, 1308, 1257, 1233, 69
7

[0056]

Example 15 N- [1- (4-methoxyphenyl) -1-methylethyl
] -3-Oxo-4-aza-5α-androst-1
-Ene - 17β-carboxamide 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid and 1- (4-methoxyphenyl)
A reaction was performed in the same manner as in Example 1 using -1-methylethylamine, and the residue was crystallized with acetone to give a yield of 64.
The target compound was obtained in%. NMR spectrum (CDCl ₃ ) δppm: 0.68 (3H, s), 0.98 (3
H, s), 0.90-2.20 (16H, m), 1.70 (3H, s), 1.72 (3H, s), 3.
33 (1H, t, J = 8Hz), 3.80 (3H, s), 5.48 (1H, br.s), 5.76 (1
H, br.s), 5.83 (1H, d, J = 10Hz), 6.82 (1H, d, J = 10Hz), 6.8
8 (1H, d, J = 9Hz), 7.32 (1H, d, J = 9Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2969, 2938,
1672, 1599, 1514, 1455, 1248, 1181, 1035, 825

[0057]

Example 16 N- [1- (3,5-dimethoxyphenyl) -1-methyi
Ruethyl] -3-oxo-4-aza-5α-andross
Tan-17β-carboxamide 3-oxo-4-aza-5α-androstane-17β
-Carboxylic acid and 1- (3,5-dimethoxyphenyl)-
Using 1-methylethylamine and in the same manner as in Example 1, the target compound was obtained with a yield of 69%. NMR spectrum (CDCl ₃ ) δppm: 0.70 (3H, s), 0.91 (3
H, s), 0.76-2.46 (20H, m), 1.67 (3H, s), 1.69 (3H, s), 3.0
6 (1H, dd, J = 11,4Hz), 3.78 (6H, s), 5.50 (1H, s), 5.83 (1
H, s), 6.34 (1H, t, J = 2Hz), 6.55 (1H, d, J = 2Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2939, 1670,
1588, 1494, 1456, 1311, 1156, 844, 696

[0058]

Example 17 N- [1- (3-methoxyphenyl) -1-methylethyl
]]-3-oxo-4-aza-5α-androstane
17β-Carboxamide 3-oxo-4-aza-5α-androstane-17β
Using -carboxylic acid and 1- (3-methoxyphenyl) -1-methylethylamine, the target compound was obtained in a yield of 72% by the same method as in Example 1. NMR spectrum (CDCl ₃ ) δppm: 0.69 (3H, s), 0.91 (3
H, s), 0.75-2.16 (18H, m), 2.38-2.43 (2H, m), 3.05 (1H, d
d, J = 11,5Hz), 3.80 (3H, s), 5.49 (1H, br.s), 5.51 (1H, b
rs), 6.75-6.79 (1H, m), 6.94-7.00 (2H, m), 7.22-7.28
(1H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3197,
2940, 1699, 1676, 1587, 1
496, 1233, 1046, 980, 699

[0059]

Example 18 N-diphenylmethyl-4-methyl-3-oxo-4-
Azaandrost-5-ene-17β-carboxamide 4-aza-4-methyl-3-oxoandrost-5
Using ene-17β-carboxylic acid and benzhydrylamine, the target compound was obtained in a yield of 59% by the same method as in Example 1. NMR spectrum (CDCl ₃ ) δppm: 0.70 (3H,
s), 1.05 (3H, s), 0.80-2.35 (16H, m), 2.45-2.57 (2H, m),
3.12 (3H, s), 5.04 (1H, m), 5.89 (1H, d, J = 9Hz), 6.29 (1
H, d, J = 9Hz), 7.10-7.40 (10H, m) infrared absorption spectrum ν _max cm ^-1 (KBr): 3314, 2944,
1669, 1642, 1627, 1524, 1494, 1385, 1124, 1054, 69
9

[0060]

Example 19 N-Diphenylmethyl-4-aza-4-methyl-3-o
Xoandrost-1-ene-17β-carboxamide 4-aza-4-methyl-3-oxoandrost-1-
Using ene-17β-carboxylic acid and benzhydrylamine, a reaction was carried out in the same manner as in Example 1, and the residue was crystallized with acetone to obtain the target compound with a yield of 82%. NMR spectrum (CDCl ₃ ) δppm: 0.69 (3H, s), 0.92 (3
H, s), 0.80-2.30 (16H, m), 2.95 (3H, s), 3.35 (1H, dd, J = 1
3,4Hz), 5.86 (1H, d, J = 10Hz), 5.88 (1H, d, J = 8Hz), 6.28 (1
H, d, J = 8Hz), 6.67 (1H, d, J = 10Hz), 7.20-7.40 (10H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2966, 2940,
1663, 1602, 1519, 1494, 1448, 1394, 1221, 698

[0061]

Example 20 N-Diphenylmethyl-3-oxo-4-aza-5α-
Androstan-17β-carboxamide 3-oxo-4-aza-5α-androstan-17β
-101 mg of carboxylic acid, 4-dimethylaminopyridine catalyst amount and 0.132 ml of triethylamine were dissolved in 4 ml of methylene chloride to give benzhydrylamine 0.108.
ml was added, and the mixture was stirred at room temperature. 0.050 ml of trifluoromethanesulfonyl chloride was added in 3 portions and added every 30 minutes. One hour after the addition of trifluoromethanesulfonyl chloride was completed, the reaction solution was diluted with methylene chloride, washed with 1N-hydrochloric acid, water, aqueous sodium hydrogen carbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was subjected to column chromatography using 25 g of silica gel and eluted with acetone-methylene chloride (2/98 to 30/70) to give 143 m.
g of the desired compound was obtained. The NMR spectrum and IR spectrum of this compound corresponded to those of the compound of Example 10.

[0062]

Example 21 N- [1- (4-methoxyphenyl) -1-methylethyl
]]-3-oxo-4-aza-5α-androstane
17β-Carboxamide 3-oxo-4-aza-5α-androstane-17β
-Suspension of 100 mg of carboxylic acid in dry chloroform, heating under reflux, 0.13 ml of triethylamine,
5 mg of dimethylaminopyridine and 104 mg of 1- (4-methoxyphenyl) -1-methylethylamine were added. 48 mg of 2,4,6-triisopropylbenzenesulfonyl chloride was added 3 times every 30 minutes, and the mixture was heated with stirring for 4 hours. The reaction mixture was brought to room temperature, poured into 1N hydrochloric acid, extracted with methylene chloride, washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using 10 g of silica gel (elution solvent:
It was purified by methylene chloride / acetone = 5/1 to 7/3) and crystallized from acetone-ether to obtain 147 mg of the target compound. NMR spectrum (CDCl ₃ ) δppm: 0.68 (3H,
s), 0.90 (3H, s), 0.70-2.80
(20H, m), 1.69 (3H, s), 1.71
(3H, s), 3.08 (1H, dd, J = 13,4
Hz), 3.80 (3H, s), 5.49 (1H,
br. s), 6.25 (1H, br.s), 6.8.
8 (2H, d, J = 9 Hz), 7.30 (2H, d,
J = 9Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2939, 170
1, 1674, 1615, 1514, 1497, 1455, 1360, 1251, 1180,
1034, 827

[0063]

Example 22 N-Diphenylmethyl-3-oxo-4-aza-5α-
Androstan-17β-carboxamide 3-oxo-4-aza-5α-androstan-17β
Using carboxylic acid and diphenylmethylamine in the same manner as in Example 21, the target compound was obtained in a yield of 99%. NMR spectrum (CDCl ₃ ) δppm: 0.67 (3H, s), 0.70-
2.00 (15H, m), 0.90 (3H, s), 2.15-2.30 (3H, m), 2.37-2.4
7 (2H, m), 3.03 (1H, dd, J = 5,10Hz), 5.46 (1H, br.s), 5.88
(1H, d, J = 9Hz), 6.28 (1H, d, J = 9Hz), 7.20-7.38 (10H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3288, 2935,
2868, 1664, 1521

[0064]

Example 23 N- (1-methyl-1-phenylethyl) -3-oxo
-4-aza-5α-androstane-17β-carboxy
Samide 3-oxo-4-aza-5α-androstane-17β
Using -carboxylic acid and 1-methyl-1-phenylethylamine, the target compound was prepared in the same manner as in Example 21.
Obtained in% yield. NMR spectrum (CDCl ₃ ) δppm: 0.68 (3H, s), 0.90-
2.25 (16H, m), 0.98 (3H, s), 1.70 (3H, s), 1.72 (3H, s),
2.35-2.50 (2H, m), 3.06 (1H, dd, J = 5,12Hz), 5.52 (1H, br.
s), 5.60 (1H, br.s), 7.20-7.45 (5H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2938, 2919,
1699, 1672, 1495

[0065]

Example 24 N- [1- (4-methoxyphenyl) -1-methylethyl
] -3-Oxo-4-aza-5α-androst-1
100 mg of -ene- 17β-carboxamide 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid was suspended in dry chloroform, and 0.14 ml of triethylamine, 5 mg of dimethylaminopyridine, 1- 106 mg of (4-methoxyphenyl) -1-methylethylamine was added.
49 mg of 2,4,6-triisopropylbenzenesulfonyl chloride was added 3 times every 30 minutes, and the mixture was stirred overnight. The reaction mixture was poured into 1N hydrochloric acid, extracted with methylene chloride, washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography using 10 g of silica gel (elution solvent: methylene chloride / acetone = 17/3 to 4/1) and crystallized from acetone-ether to obtain 135 mg of the target compound. NMR spectrum (CDCl ₃ ) δppm: 0.68 (3H, s), 0.98 (3
H, s), 0.90-2.20 (16H, m), 1.70 (3H, s), 1.72 (3H, s), 3.
35 (1H, t, J = 9Hz), 3.80 (3H, s), 5.48 (1H, br.s), 5.76 (1
H, br.s), 5.83 (1H, d, J = 10Hz), 6.82 (1H, d, J = 10Hz), 6.8
8 (2H, d, J = 9z), 7.32 (2H, d, J = 9Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2969, 2938,
1672, 1599, 1514, 1455, 1248, 1181, 1035, 825

[0066]

Example 25 N-diphenylmethyl-3-oxo-4-aza-5α-
Using androst-1-ene-17β-carboxamide 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid and diphenylmethylamine in the same manner as in Example 24, the target compound was obtained. Obtained in a yield of 95%. NMR spectrum (CDCl ₃ ) δppm: 0.69 (3H, s), 0.80-
2.30 (16H, m), 0.97 (3H, s), 3.31 (1H, t, J = 10Hz), 5.30 (1
H, br.s), 5.80 (1H, d, J = 9Hz), 5.89 (1H, d, J = 8Hz), 6.28 (1
H, d, J = 8Hz), 6.77 (1H, d, J = 9Hz), 7.10-7.40 (10H, m) infrared absorption spectrum ν _max cm ^-1 (KBr): 2935,
1676, 1600

[0067]

Example 26 N- (1-methyl-1-phenylethyl) -3-oxo
-4-aza-5α-androst-1-ene-17β-
Carboxamide 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid and 1-methyl-1-phenylethylamine were used in the same manner as in Example 24 to obtain 91% of the target compound. Got at a rate. NMR spectrum (CDCl ₃ ) δppm: 0.69 (3H,
s), 0.90-2.25 (16H, m), 0.98 (3H, s), 1.71 (3H, s), 1.73
(3H, s), 3.33 (1H, t, J = 8Hz), 5.53 (1H, br.s), 5.69 (1H, b
rs), 5.84 (1H, d, J = 10Hz), 6.81 (1H, d, J = 10Hz), 7.20-
7.45 (5H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2969, 2937,
1672, 1598

[0068]

Example 27 N-diphenylmethyl-3- (trifluoromethanesulfur)
Honyloxy) androst-3,5-diene-17β
-Carboxamide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid 150 mg
Was dissolved in 5 ml of dry methylene chloride, 0.14 ml of triethylamine, 5 mg of dimethylaminopyridine,
123 mg of diphenylmethylamine was added. 2, 4,
6-triisopropylbenzenesulfonyl chloride 50
mg was added 3 times every 30 minutes and then stirred overnight. The reaction mixture was poured into 1N hydrochloric acid, extracted with methylene chloride, washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using 12 g of silica gel (elution solvent: hexane / ethyl acetate = 1.
7 / 3-4 / 1) and 205 mg of the target compound
Got NMR spectrum (CDCl ₃ ) δppm: 0.71 (3H, s), 0.90〜
2.05 (13H, m), 0.96 (3H, s),
2.18-2.32 (3H, m), 2.36 (1H,
dd, J = 5, 18 Hz), 2.55 (1H, m),
5.57 (1H, m), 5.90 (1H, d, J =
8 Hz), 5.99 (1 H, s), 6.29 (1
H, d, J = 8 Hz), 7.21-7.36 (10
H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3305, 293
9, 2874, 1725, 1643, 1601, 1523, 1496

[0069]

Example 28 N- [1- (3,5-dimethoxyphenyl) -1-methyi
Ruethyl] -3- (trifluoromethanesulfonyloxy)
Shi) Androst-3,5-diene-17β-carboxy
Samide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and 1-
The target compound was obtained in a yield of 98% as in Example 27, using (3,5-dimethoxyphenyl) -1-methylethylamine. NMR spectrum (CDCl ₃ ) δppm: 0.73 (3H, s), 0.90-
2.30 (16H, m), 0.97 (3H, s), 1.68 (3H, s), 1.70 (3H, s),
2.36 (1H, dd, J = 5,18Hz), 2.56 (1H, m), 3.79 (6H, s), 5.53
(1H, m), 5.57 (1H, br.s), 5.99 (1H, s), 6.34 (1H, t, J = 2H
z), 6.56 (2H, d, J = 2Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3351, 2968,
2943, 1665, 1598, 1504

[0070]

Example 29 N- [1- (4-methoxyphenyl) -1-methylethyl
]]-3- (Trifluoromethanesulfonyloxy) a
Androst-3,5-diene-17β-carboxamide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and 1- (4
The target compound was obtained in a yield of 98% as in Example 27, using -methoxyphenyl) -1-methylethylamine. NMR spectrum (CDCl ₃ ) δppm: 0.70 (3H, s), 0.95-
2.60 (18H, m), 0.99 (3H, s), 1.70 (3H, s), 1.71 (3H, s),
3.80 (3H, s), 5.54 (1H, s), 5.57 (1H, m), 5.99 (1H, s), 6.
86 (2H, d, J = 9Hz), 7.34 (2H, d, J = 9Hz) infrared absorption spectrum ν _max cm ^-1 (KBr): 3345,
2969, 2944, 1665, 1614, 1
514

[0071]

Example 30 N- (1-Methyl-1-phenylethyl) -3- (tri
Fluoromethanesulfonyloxy) androst-3,
5-diene-17β-carboxamide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and 1-methyl-1-phenylethylamine were used in the same manner as in Example 27 to obtain the object. The compound was obtained in 90% yield. NMR spectrum (CDCl ₃ ) δppm: 0.70 (3H,
s), 0.95-2.30 (16H, m), 0.97 (3H, s), 1.71 (3H, s), 1.73
(3H, s), 2.37 (1H, dd, J = 5,18Hz), 2.57 (1H, m), 5.58 (1H,
m), 5.62 (1H, br.s), 6.00 (1H, s), 7.24 (1H, d, J = 8Hz), 7.
33 (2H, t, J = 8Hz), 7.41 (2H, d, J = 8Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3343, 2970,
2944, 1658, 1496

[0072]

Example 31 N- [1- (4-methylphenyl) -1-methylethyl
]]-3- (Trifluoromethanesulfonyloxy) a
Androst-3,5-diene-17β-carboxamide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and 1- (4
The target compound was obtained in a yield of 72% as in Example 27, using -methylphenyl) -1-methylethylamine. NMR spectrum (CDCl ₃ ) δppm: 0.71 (3H, s), 0.95-
2.42 (17H, m), 0.97 (3H, s), 1.70 (3H, s), 1.72 (3H, s),
2.32 (3H, s), 2.56 (1H, m), 5.52 (1H, s), 5.57 (1H, m), 5.
99 (1H, s), 7.14 (2H, d, J = 8Hz), 7.30 (2H, d, J = 8Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3344, 2970,
2944, 1660, 1515

[0073]

Example 32 N- (4,4′-dimethoxydiphenylmethyl) -3-
(Trifluoromethanesulfonyloxy) Androst
-3,5-Diene-17β-carboxamide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and 4,4 ′
Using dimethoxydiphenylmethylamine in the same manner as in Example 27, the target compound was obtained in a yield of 99%. NMR spectrum (CDCl ₃ ) δppm: 0.71 (3H, s), 0.95-
2.00 (13H, m), 0.96 (3H, s), 2.15-2.30 (3H, m), 2.36 (1H,
dd, J = 5,18Hz), 2.56 (1H, m), 3.79 (3H, s), 3.80 (3H, s),
5.57 (1H, m), 5.80 (1H, d, J = 8Hz), 5.99 (1H, s), 6.18 (1H,
d, J = 8Hz), 6.86 (4H, m), 7.14 (4H, m)

[0074]

Example 33 N-phenyl-3- (trifluoromethanesulfonyl o
X) Androst-3,5-diene-17β-carbo
Using xamide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and aniline in the same manner as in Example 27, the target compound was obtained as 96
Obtained in% yield. NMR spectrum (CDCl ₃ ) δppm: 0.81 (3H, m), 0.95-
1.97 (12H, m), 0.97 (3H, s), 2.08-2.42 (5H, m), 2.56 (1H,
m), 5.59 (1H, m), 6.00 (1H, s), 6.95 (1H, br.s), 7.10 (1
H, t, J = 8Hz), 7.32 (2H, t, J = 8Hz), 7.51 (2H, d, J = 8Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3319, 2967,
2947, 1664, 1599, 1523, 1500

[0075]

Example 34 N- (1,1-dimethylethyl) -3- (trifluoro
Methanesulfonyloxy) and lost-3,5-die
-17β-carboxamide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and 1,1-
Using dimethylethylamine, the target compound was obtained in a yield of 99% as in Example 27. NMR spectrum (CDCl ₃ ) δppm: 0.72 (3H, s), 0.95-
1.80 (11H, m), 0.97 (3H, s), 1.36 (9H, s), 1.88-2.30 (5H,
m), 2.36 (1H, dd, J = 5,18Hz), 2.56 (1H, m), 5.16 (1H, br.
s), 5.58 (1H, m), 5.99 (1H, s) infrared absorption spectrum ν _max cm ^-1 (KBr): 3425,
2972, 2951, 1666, 1504

[0076]

Example 35 N-ethyl-3- (trifluoromethanesulfonyloxy )
Shi) Androst-3,5-diene-17β-carboxy
Using samide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and ethylamine hydrochloride in the same manner as in Example 27, the target compound was obtained in a yield of 85%. NMR spectrum (CDCl ₃ ) δppm: 0.73 (3H,
s), 0.95-2.42 (17H, m), 0.97 (3H, s), 1.14 (3H, t, J = 7H
z), 2.56 (1H, m), 3.21-3.41 (2H, m), 5.35 (1H, br.s), 5.
58 (1H, m), 5.99 (1H, s) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3328, 2969,
2942, 1648, 1537

[0077]

Example 36 N, N-Dibenzyl-3- (trifluoromethanesulfon
Nyloxy) androst-3,5-diene-17β-
Carboxamide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and N, N-
Using dibenzylamine as in Example 21,
The target compound was obtained in a yield of 90%. NMR spectrum (CDCl ₃ ) δppm: 0.90-1.95 (13H, m),
0.92 (3H, s), 0.98 (3H, s), 2.20-2.62 (4H, m), 2.77 (1H,
t, J = 9Hz), 3.74 (1H, d, J = 15Hz), 4.17 (1H, d, J = 17Hz), 4.
94 (1H, d, J = 17Hz), 5.48 (1H, dJ = 15Hz), 5.56 (1H, m), 5.
98 (1H, s), 7.11-7.13 (2H, d, J = 7Hz), 7.21-7.24 (2H, d, J =
7Hz), 7.27-7.40 (6H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 2945, 1642,
1496

[0078]

Example 37 N, N-diethyl-3- (trifluoromethanesulfoni
Luoxy) androst-3,5-diene-17β-ca
Ruboxamide 3- (trifluoromethanesulfonyloxy) androst-3,5-diene-17β-carboxylic acid and N, N-
The target compound was obtained in a yield of 94% as in Example 27, using diethylamine. NMR spectrum (CDCl ₃ ) δppm: 0.80 (3H, s), 0.95-
1.95 (13H, m), 0.97 (3H, s), 1.14 (6H, t, J = 7Hz), 2.23-2.
40 (3H, m), 2.56 (1H, m), 2.65 (1H, t, J = 9Hz), 3.05-3.15
(2H, br.s), 3.65-3.80 (2H, br.s), 5.59 (1H, m), 6.00 (1
H, s) infrared absorption spectrum ν _max cm ^-1 (KBr): 2936, 1629

[0079]

Example 38 N-diphenylmethyl-3-oxoandrost-4-
Example 17 Using ene-17β-carboxamide 3- oxoandrost -4-ene-17β-carboxylic acid and N-diphenylmethylamine
Similarly to the above, the target compound was obtained in a yield of 94%. NMR spectrum (CDCl ₃ ) δppm: 0.72 (3H, s), 0.93-
2.05 (14H, m), 1.18 (3H, s), 2.20-2.48 (6H, m), 5.73 (1H,
s), 5.89 (1H, d, J = 8Hz), 6.29 (1H, d, J = 8Hz), 7.21-7.36
(10H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3374, 2942,
2922, 1676, 1665, 1515, 1495

[0080]

Example 39 N- (1-methyl-1-phenylethyl) -3-oxo
Using androst-4-ene-17β-carboxamide 3-oxoandrost-4-ene-17β-carboxylic acid and 1-methyl-1-phenylethylamine,
The target compound was obtained in a yield of 91% as in Example 27. NMR spectrum (CDCl ₃ ) δppm: 0.72 (3H, s), 0.93-
1.13 (3H, m), 1.19 (3H, s), 1.23-1.32 (2H, m), 1.43-1.90
(7H, m), 1.71 (3H, s), 1.73 (3H, s), 2.02-2.22 (4H, m),
2.24-2.50 (4H, m), 5.53 (1H, s), 5.73 (1H, s), 7.23 (1H,
m), 7.31-7.36 (2H, m), 7.40-7.42 (2H, m) infrared absorption spectrum ν _max cm ^-1 (KBr): 3422,
2971, 2942, 1672, 1617, 1
499

[0081]

Example 40 N- [1- (3,5-dimethoxyphenyl) -1-methyi
Ruethyl] -3-oxoandrost-4-ene-17
Using β-carboxamide 3-oxoandrost-4-ene-17β-carboxylic acid and 1- (3,5-dimethoxyphenyl) -1-methylethylamine, in the same manner as in Example 27, the target compound was converted to 96%. It was obtained in a yield of. NMR spectrum (CDCl ₃ ) δppm: 0.74 (3H,
s), 0.92-1.15 (3H, m), 1.19 (3H, s), 1.25-1.35 (2H, m),
1.42-1.90 (7H, m), 1.67 (3H, s), 1.70 (3H, s), 2.00-2.23
(4H, m), 2.25-2.50 (4H, m), 3.79 (6H, s), 5.52 (1H, s),
5.73 (1H, s), 6.34 (1H, t, J = 2Hz), 6.56 (2H, d, J = 2Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3376, 2955,
2945, 1669, 1658, 1612, 1589, 1525

[0082]

Example 41 N-Diphenylmethyl-3-cyanoandrost-3,
5-Diene-17β-carboxamide Using 3-cyanoandrost-3,5-diene-17β-carboxylic acid and N-diphenylmethylamine in the same manner as in Example 27, the target compound was obtained in 90% yield. Obtained. NMR spectrum (CDCl ₃ ) δppm: 0.71 (3H, s), 0.90-
2.02 (13H, m), 0.92 (3H, s), 2.20-2.45 (5H, m), 5.77 (1H,
t, J = 4Hz), 5.88 (1H, d, J = 8Hz), 6.29 (1H, d, J = 8Hz), 6.65
(1H, s), 7.22-7.36 (10H, m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3420, 2967,
2950, 2206, 1664, 1636, 1603, 1485

[0083]

Example 42 N- (1-methyl-1-phenylethyl) -3-cyano
Androst-3,5-diene-17β-carboxami
Using do- 3-cyanoandrost-3,5-diene-17β-carboxylic acid and 1-methyl-1-phenylethylamine and in the same manner as in Example 27, the target compound was obtained in a yield of 88%. NMR spectrum (CDCl ₃ ) δppm: 0.71 (3H, s), 0.90-
1.92 (12H, m), 0.94 (3H, s), 1.71 (3H, s), 1.73 (3H, s),
2.03-2.23 (3H, m), 2.27-2.45 (3H, m), 5.55 (1H, br.s),
5.78 (1H, m), 6.66 (1H, s), 7.23 (1H, t, J = 8Hz), 7.34 (2H,
t, J = 8Hz), 7.41 (2H, d, J = 8Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3351, 2966,
2942, 2203, 1665, 1635, 1603, 1514, 1495

[0084]

Example 43 N- [1- (3,5-dimethoxyphenyl) -1-methyi
Ruethyl] -3-cyanoandrost-3,5-diene
-17β-carboxamide 3-cyanoandrost-3,5-diene-17β-carboxylic acid and 1- (3,5-dimethoxyphenyl) -1-
The target compound was obtained in a yield of 95% as in Example 27, using methylethylamine. NMR spectrum (CDCl ₃ ) δppm: 0.73 (3H, s), 0.90-
1.92 (12H, m), 0.94 (3H, s), 1.68 (3H, s), 1.70 (3H, s),
2.05-2.22 (3H, m), 2.27-2.43 (3H, m), 3.79 (6H, s), 5.53
(1H, s), 5.78 (1H, t, J = 4Hz), 6.34 (1H, t, J = 2Hz), 6.56 (2
H, d, J = 2Hz), 6.66 (1H, s) infrared absorption spectrum ν _max cm ^-1 (KBr): 3352, 2966,
2941, 2203, 1675, 1634, 1598, 1510

[0085]

Example 44 N-diphenylmethyl-3- (methoxycarbonyl) a
Androstane-3,5-gen-17β-carboxamid
De 3-carbomethoxyandrostane-3,5-diene-
The target compound was obtained in a yield of 97% as in Example 27, using 17β-carboxylic acid and diphenylmethylamine. NMR spectrum (CDCl ₃ ) δppm: 0.71 (3H, s), 0.90 (3
H, s), 1.00-2.03 (13H, m), 2.18-2.35 (4H, m), 2.51 (1H, d
d, J = 5,18Hz), 3.75 (3H, s), 5.80 (1H, m), 5.88 (1H, d, J = 8
Hz), 6.30 (1H, d, J = 8Hz), 7.03 (1H, s), 7.22-7.53 (10H,
m) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3379, 2970,
2896, 1707, 1682, 1630, 1504, 1495

[0086]

Example 45 N- (1-methyl-1-phenylethylamine) -3-
(Methoxycarbonyl) androstane-3,5-die
-17β-carboxamide 3-carbomethoxyandrostane-3,5-diene-
Using 17β-carboxylic acid and 1-methyl-1-phenylethylamine, the target compound was obtained in a yield of 92% as in Example 27. NMR spectrum (CDCl ₃ ) δppm: 0.71 (3H, s), 0.88-
1.82 (11H, m), 0.92 (3H, s), 1.71 (3H, s), 1.73 (3H, s),
1.90 (1H, dd, J = 4,13Hz), 2.03〜2.35 (5H, m), 2.52 (1H, d
d, J = 5,18Hz), 3.75 (3H, s), 5.56 (1H, br.s), 5.81 (1H,
m), 7.04 (1H, s), 7.23 (1H, t, J = 8Hz), 7.34 (2H, t, J = 8H
z), 7.42 (2H, d, J = 8Hz) Infrared absorption spectrum ν _max cm ^-1 (KBr): 3351, 2967,
2944, 1709, 1679, 1664, 1636, 1515, 1496

[0087]

Example 46 N- [1- (3,5-dimethoxyphenyl) -1-methyi
Ruethyl] -3- (methoxycarbonyl) androsta
3,5-diene-17β-carboxamide 3-carbomethoxyandrostane-3,5-diene-
Using 17β-carboxylic acid and 1- (3,5-dimethoxyphenyl) -1-methylethylamine in the same manner as in Example 27, the target compound was obtained in a yield of 97%. NMR spectrum (CDCl ₃ ) δppm: 0.74 (3H,
s), 0.91 (3H, s), 1.02-1.18
(3H, m), 1.20-1.37 (2H, m),
1.42-1.82 (6H, m), 1.68 (3H,
s), 1.70 (3H, s), 1.90 (1H, d
d, J = 4, 13 Hz), 2.04-2.33 (5
H, m), 2.52 (1H, dd, J = 5,18H
z), 3.75 (3H, s), 3.79 (6H,
s), 5.53 (1H, s), 5.80 (1H,
m), 6.34 (1H, t, J = 2Hz), 6.5
7 (2H, d, J = 2Hz), 7.04 (1H, s) infrared absorption spectrum ν _max cm ^-1 (KBr): 3351, 296
6, 2943, 1708, 1679, 1636, 1598, 1509

[0088]

Reference Example 1 N- [1- (4-methoxyphenyl) -1-methylethyl
]]-3-oxo-4-aza-5α-androstane
17β-Carboxamide 3-oxo-4-aza-5α-androstane-17β
-Supply 215 mg of carboxylic acid in 2 ml of dichloromethane, add 0.4 ml of Vilsmeier reagent (prepared from 1.7 ml of dimethylformamide, 1.8 ml of phosphorus oxychloride and 5 ml of methylene chloride) at room temperature, and add 3 ml at room temperature.
Stir for 0 minutes. Then 1- (4-methoxyphenyl)
137 mg of -1-methylethylamine and 140 ml of triethylamine in 1 ml of dichloromethane were added dropwise,
It was stirred at room temperature for 1 hour. Dilute with ethyl acetate, dilute hydrochloric acid,
The extract was washed with saturated brine, 5% aqueous sodium hydrogen carbonate solution and saturated brine, dried and the solvent was evaporated. The crystalline residue is purified by silica gel chromatography, 20-30%
180 mg from the effluent of methylene chloride containing acetone
The target compound (yield 57%) was obtained. NMR of this compound
The spectrum and infrared absorption spectrum were in agreement with those of the compound of Example 1.

[0089]

Reference Example 2 N-diphenylmethyl-3-oxo-4-aza-5α-
Androstan-17β-carboxamide 3-oxo-4-aza-5α-androstan-17β
-Using carboxylic acid, Vilsmeier reagent and diphenylmethylamine, reaction and treatment were carried out in the same manner as in Reference Example 1 to obtain the target compound with a yield of 50%. The NMR spectrum and infrared absorption spectrum of this compound corresponded to those of the compound of Example 10.

[0090]

[Reference Example 3] N- [1- (4-methoxyphenyl) -1-methylethyl
] -3-Oxo-4-aza-5α-androst-1
-En - 17β-carboxamide N- [1- (4-methoxyphenyl) -1-methylethyl] -3-oxo-4-aza-5α-androstane-
200 mg of 17β-carboxamide was dissolved in 20 ml of 1,4-dioxane, 117 mg of 2,3-dichloro-5,6-dicyano-p-benzoquinone and 0.456 m of N, O-trimethylsilyl-trifluoroacetamide.
1 was added, and the mixture was stirred at room temperature for 1 hour and then heated under reflux overnight. The reaction solution was diluted with methylene chloride, washed twice with 1N-sodium hydroxide and washed with saturated saline, dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography using 25 g of silica gel and eluted with acetone-methylene chloride (2/98 to 30/70) to give 14
0 mg of the desired compound was obtained. The NMR spectrum and infrared absorption spectrum of this compound corresponded to those of the compound of Example 15.

[0091]

Reference Example 4 N-diphenylmethyl-3-oxo-4-aza-5α-
Androst-1-ene-17β-carboxamide N-diphenylmethyl-3-oxo-4-aza-5α-
Androstane-17β-carboxamide and 2,3-
Using dichloro-5,6-dicyano-p-benzoquinone, the reaction and treatment were carried out in the same manner as in Reference Example 3 to obtain the target compound with a yield of 60%. NMR spectrum (CDCl ₃ ) δppm: 0.69 (3H, s), 0.97 (3
H, s), 0.80-2.30 (16H, m), 3.31 (1H, t, J = 10Hz), 5.30 (1
H, br.s), 5.80 (1H, d, J = 9Hz), 5.89 (1H, d, J = 8Hz), 6.28 (1
H, d, J = 8Hz), 6.77 (1H, d, J = 9Hz), 7.10-7.40 (10H, m) infrared absorption spectrum ν _max cm ^-1 (KBr): 2935,
1676, 1600, 1518, 1493, 1
448, 698

Claims (20)

[Claims] 1. A compound represented by the general formula (I): [In formula, A is the following general formula (I-1), (I-2), or (I-
A group having 3) (In the above formula, R ³ represents a hydrogen atom or a lower alkyl group, R ⁴ represents a hydrogen atom, a protected hydroxyl group, a substituted hydroxyl group, a protected carboxy group or a cyano group, and R ⁵ represents A hydrogen atom or an amino group is shown, and a bond including a dotted line is a single bond or a double bond. A carboxylic acid compound having the general formula R ⁶ SO ₂ X (IVa) or (R ⁶ SO ₂ ) ₂ O (IVb) (wherein R ⁶ is a lower alkyl group, a halogenoalkyl group, a camphanyl group, isocyano A group or an aryl group which may be substituted with a group selected from Substituent Group A, X represents a halogen atom) in the presence of a sulfonyl compound having the general formula NHR ¹ R ² (III) Wherein R ¹ and R ² are the same or different and each is a hydrogen atom, a lower alkyl group, or a substituted lower alkyl group (the substituent is substituted with a group selected from Substituent group A and Substituent group B). Represents an optionally substituted aryl group, a heteroaryl group optionally substituted with a group selected from Substituent group A, or a cycloalkyl group optionally substituted with a group selected from Substituent group A), an alkenyl group. Or shiku A lower alkyl group is shown. ]
Characterized by reacting an amine compound having
General formula (II): (In the formula, R ¹ , R ² and A have the same meanings as described above.) A method for producing a steroid-17-amide. [Substituent Group A] Lower alkyl group, lower alkoxy group and halogen atom [Substituent Group B] Hydroxyl group, lower alkoxycarbonyl group and di-lower alkylamino group. 2. A compound represented by the general formula (I): [In formula, A is the following general formula (I-1), (I-2), or (I-
A group having 3) (In the above formula, R ³ represents a hydrogen atom or a lower alkyl group, R ⁴ represents a hydrogen atom, a protected hydroxyl group, a substituted hydroxyl group, a protected carboxy group or a cyano group, and R ⁵ represents A hydrogen atom or an amino group is shown, and a bond including a dotted line is a single bond or a double bond. In an inert solvent with a base and a general formula R ⁶ SO ₂ X (IVa) or (R ⁶ SO ₂ ) ₂ O (IVb) (wherein R ⁶ is a lower alkyl group, halogeno An alkyl group, a camphanyl group, an isocyano group, or an aryl group which may be substituted with a group selected from the substituent group A, and X represents a halogen atom) in the presence of a sulfonyl compound,
General formula NHR ¹ R ² (III) [In the formula, R ¹ and R ² are the same or different and each is a hydrogen atom, a lower alkyl group, or a substituted lower alkyl group (the substituent is a substituent group A or a substituted group). An aryl group which may be substituted with a group selected from the group B, a heteroaryl group which may be substituted with a group selected from the group A, or a group which is selected from a group A A good cycloalkyl group), an alkenyl group or a cycloalkyl group. ]
Characterized by reacting an amine compound having
General formula (II): (In the formula, R ¹ , R ² and A have the same meanings as described above.) A method for producing a steroid-17-amide. [Substituent Group A] Lower alkyl group, lower alkoxy group and halogen atom [Substituent Group B] Hydroxyl group, lower alkoxycarbonyl group and di-lower alkylamino group. 3. A compound represented by the general formula (I): [In formula, A is the following general formula (I-1), (I-2), or (I-
A group having 3) (In the above formula, R ³ represents a hydrogen atom or a lower alkyl group, R ⁴ represents a hydrogen atom, a protected hydroxyl group, a substituted hydroxyl group, a protected carboxy group or a cyano group, and R ⁵ represents A hydrogen atom or an amino group is shown, and a bond including a dotted line is a single bond or a double bond. A carboxylic acid compound having a general formula R ⁶ SO ₂ X (IVa) (wherein R ⁶ is a lower alkyl group, a halogenoalkyl group, a camphanyl group, an isocyano group or a substituent group) in an inert solvent. In the presence of a sulfonyl compound having an aryl group which may be substituted with a group selected from A, X represents a halogen atom), a compound represented by the general formula: NHR ¹ R ² (III) [wherein R ¹ and R ² is the same or different and is a hydrogen atom, a lower alkyl group, or a substituted lower alkyl group (the substituent is an aryl group which may be substituted with a group selected from Substituent group A and Substituent group B). , A heteroaryl group which may be substituted with a group selected from the substituent group A or a cycloalkyl group which may be substituted with a group selected from the substituent group A), an alkenyl group or a cycloalkyl group. It is shown. ]
Characterized by reacting an amine compound having
General formula (II): (In the formula, R ¹ , R ² and A have the same meanings as described above.) A method for producing a steroid-17-amide. [Substituent Group A] Lower alkyl group, lower alkoxy group and halogen atom [Substituent Group B] Hydroxyl group, lower alkoxycarbonyl group and di-lower alkylamino group. 4. In one claim selected from claims 1 to 3, R ⁶ is a halogenoalkyl group or a substituent group A.
A process for producing steroid-17-amides, which is an aryl group which may be substituted with a group selected from the following. 5. In one claim selected from claims 1 to 4, R ¹ and R ² are the same or different and each is a hydrogen atom, a lower alkyl group or a substituted lower alkyl group (wherein the substituent is Is an aryl group which may be substituted with a group selected from Substituent group A and Substituent group B or an unsubstituted heteroaryl group.). 6. In one claim selected from claims 1 to 4, R ¹ and R ² are the same or different and each is a hydrogen atom, a lower alkyl group or a substituted lower alkyl group (wherein the substituent is , An aryl group which may be substituted with a group selected from Substituent group A or an unsubstituted heteroaryl group.). 7. The method according to claim 1, wherein R ¹ is a hydrogen atom and R ² is a lower alkyl group or a substituted lower alkyl group (wherein the substituent is a substituent). An aryl group which may be substituted with a group selected from Group A or an unsubstituted heteroaryl group).
Process for producing steroid-17-amides. 8. The method according to claim 7, wherein R ² is isopropyl group, isobutyl group, t-butyl group or substituted C _1-.
C ₃ alkyl group [the substituent is a phenyl group, a substituted phenyl group (the substituent is methyl, methoxy, ethoxy, fluoro or chloro), a furyl group or a thienyl group. ] The manufacturing method of the steroid 17-amides which are these. 9. The method according to claim 7, wherein R ² is a t-butyl group,
Group [wherein having the formula _{-C (CH 3) (CH 3} ) -R 2 a, R 2 a is substituted phenyl group (the substituent is methyl, methoxy, ethoxy, fluoro or chloro ), A furyl group or a thienyl group. Or a C ₁ -C ₃ alkyl group substituted with 2 to 3 substituents [wherein the substituent is an optionally substituted phenyl group (wherein the substituent is methyl, methoxy, ethoxy, fluoro or chloro]] .), A furyl group or a thienyl group. ], The steroid-17
-Method for producing amides. 10. The group according to claim 7, wherein R ² is a t-butyl group and has the formula —C (CH ₃ ) (CH ₃ ) —R ² _a [wherein R ^2
2 _a represents an optionally substituted phenyl group (the substituent is methyl, methoxy, ethoxy, fluoro or chloro) or a thienyl group. ], A phenyl ring is a diphenylmethyl, 1,2-diphenylethyl or 1,1-diphenylethyl group optionally substituted with methyl, methoxy, ethoxy, chloro or fluoro,
Process for producing steroid-17-amides. 11. A method for producing a steroid-17-amide according to claim 1, wherein A is the general formula (I-1). 12. The method according to claim 11, wherein R ³ is a hydrogen atom,
A process for producing steroid-17-amides, which is a methyl group or an ethyl group. 13. The method for producing a steroid-17-amide according to claim 11, wherein R ³ is a hydrogen atom or a methyl group. 14. The method for producing a steroid-17-amide according to claim 1, wherein the bond at the 5- and 6-positions is a single bond. 15. A method for producing a steroid-17-amide according to claim 1, wherein A is the general formula (I-2). 16. The method for producing a steroid-17-amide according to claim 15, wherein R ⁴ is a protected hydroxyl group, a protected carboxy group or a cyano group. 17. The method for producing a steroid-17-amide according to claim 15 or 16, wherein the bond containing a dotted line is a double bond. 18. A method for producing a steroid-17-amide according to claim 1, wherein A is the general formula (I-3). 19. The method for producing a steroid-17-amide according to claim 18, wherein R ⁵ is a hydrogen atom. 20. The method for producing a steroid-17-amide according to claim 18 or 19, wherein the bond containing a dotted line is a double bond.