JP2006188504A - Pharmaceutical composition containing cyclic tertiary amine compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a pharmaceutical composition containing a cyclic tertiary amine compound, capable of inhibiting the production of inflammatory cytokines. <P>SOLUTION: The pharmaceutical composition contains a compound of the general formula(I) or a pharmacologically acceptable salt thereof. In the general formula(I), A is a (substituted) trivalent group such as (substituted) pyrimidine or pyrrole group; R<SP>1</SP>is a (substituted) aryl or heteroaryl; R<SP>2</SP>is a (substituted) heteroaryl; and R<SP>3</SP>is a cyclic tertiary amino group. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a pharmaceutical composition containing a cyclic tertiary amine compound. More specifically, antipyretic / analgesic / anti-inflammatory agents and rheumatoid arthritis having an inhibitory action on the production of inflammatory cytokines such as interleukin (IL) -1, IL-6, IL-8, tumor necrosis factor (TNF) A pharmaceutical composition comprising a cyclic tertiary amine compound useful as a preventive or therapeutic agent for autoimmune diseases such as osteoarthritis, diabetes (particularly type I diabetes), bone diseases such as osteoporosis, and other diseases involving the cytokines Related to things.

  Conventionally, non-steroidal anti-inflammatory drugs (NSAIDs) have antipyretic, analgesic, and anti-inflammatory effects mainly due to inhibition of prostaglandin (PG) biosynthesis by cyclooxygenase inhibition. It has been frequently used for inflammatory and painful diseases. For rheumatoid arthritis and the like, NSAID is used for symptomatic treatment, and an immunomodulator (DMARD) is used for causal treatment.

  Conventional NSAIDs cause gastrointestinal disorders such as gastric ulcers from the mechanism of action, and have problems in long-term continuous use. In addition, DMARD has not yet developed a stable and clear medicinal effect. In recent years, active substances collectively called cytokines produced by immunocompetent cells have been found. Among them, interleukin (IL) -1, IL-6, IL-8, tumor necrosis factor (TNF) and the like are called inflammatory cytokines, activation of the arachidonic acid metabolic system which is a PG production system, leukocytes Various actions as inflammatory mediators have been elucidated, such as migration of cells, induction of acute phase proteins, and activation of osteoclasts, and these inflammatory cytokine production inhibitors have different mechanisms of action It is expected as a therapeutic agent for a new generation of antipyretic / analgesic / anti-inflammatory drugs and autoimmune diseases such as rheumatoid arthritis, bone diseases such as osteoporosis, and other diseases involving the cytokines.

So far, as compounds having an action of suppressing the production of inflammatory cytokines, for example, heteroaryl compounds (see Patent Documents 1 to 9 and Non-Patent Document 1) and the like are known. Therefore, it is desired to develop a compound that is superior in properties.
International Publication No. 96/21452 Pamphlet International Publication No. 97/5877 Pamphlet International Publication No. 97/23479 Pamphlet International Publication No. 98/52937 Pamphlet International Publication No. 00/31063 Pamphlet International Publication No. 02/57255 Pamphlet International Publication No. 02/57264 Pamphlet International Publication No. 02/57265 Pamphlet European Patent Application No. 1070711 J. et al. Med. Chem. , Vol. 39 3929-3937 (1996)

  As a result of intensive studies over many years on the synthesis and pharmacological action of compounds that can suppress the production of the above-mentioned inflammatory cytokines, the present inventors have found that cyclic tertiary amine compounds have an excellent inflammatory cytokine production-inhibiting action. Thus, the present invention was completed.

That is, the present invention
(1) A pharmaceutical composition comprising a compound having the following general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient:

{Where,
A represents a trivalent group selected from benzene, pyridine, pyridazine, pyrimidine, pyrrole, furan, thiophene, pyrazole, imidazole, isoxazole and isothiazole, which may be substituted with a group selected from the substituent group δ. Show
R ¹ is an aryl group optionally substituted with a group selected from substituent group α and substituent group β; or optionally substituted with a group selected from substituent group α and substituent group β Represents a heteroaryl group,
R ² represents a heteroaryl group having at least one nitrogen atom, which may be substituted with a group selected from substituent group α and substituent group β,
R ³ is a group having the following general formulas (IIa) and (IIb):

[Where:
A bond including a dotted line indicates a single bond or a double bond,
Ring B represents a 4- to 7-membered heterocyclyl ring (the ring is saturated or unsaturated; may be condensed with an aryl group, heteroaryl group, cycloalkyl group, or heterocyclyl group);
X represents a linear or branched alkylene group having 1 to 5 carbon atoms,
Y represents a single bond or a group having the formula C (R ⁸ a) (R ⁸ b) (R ⁸ a and R ⁸ b are the same or different and each represents a hydrogen atom, a hydroxy group, a halogen atom, or a lower alkyl group. Or a lower alkoxy group, R ⁸ a and R ⁸ b together represent an oxo group or a methylene group, or a carbon atom to which R ⁸ a and R ⁸ b are bonded. And a 3- to 6-membered cycloalkyl group is formed.)
Z represents an arylene group or a heteroarylene group,
m represents 0 to 2,

R ⁵ is a carboxy group, a lower alkoxycarbonyl group, an aralkyloxycarbonyl group, an aryloxycarbonyl group, a group having the formula CONR ^a R ^b , a group having the formula COR ^c , a group having the formula SO ₂ NR ^a R ^b , a formula A group having SO ₂ R ^c or a group having the formula SOR ^c
R ^a and R ^b are the same or different and each represents a hydrogen atom, a hydroxy group,
A lower alkyl group which may be substituted with a group selected from substituent group α,
A lower alkenyl group optionally substituted with a group selected from substituent group α,
A lower alkynyl group optionally substituted with a group selected from substituent group α,
A lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, an aralkyloxy group,
A cycloalkyl group, a lower alkyl group substituted with a cycloalkyl group,
Aryl group, aralkyl group,
A heteroaryl group, a lower alkyl group substituted with a heteroaryl group,
Represents an amino group or a mono- or di-lower alkylamino group,
R ^c represents a hydrogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy lower alkyl group or a hydroxy lower alkyl group,

R ⁶ consists of a hydrogen atom, hydroxy group, amino group, nitro group, cyano group, halogen atom, lower alkyl group, lower alkoxy group, lower alkylthio group, halogeno lower alkyl group, halogeno lower alkoxy group and halogeno lower alkylthio group. 1 to 2 groups selected from the group,
n represents 1 to 2 (when n is 2, R ⁶ may be the same or different);

R ⁷ is 1 to 3 selected from the group consisting of a hydrogen atom, a hydroxy group, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halogeno lower alkyl group, a halogeno lower alkoxy group, and a halogeno lower alkylthio group The group of is shown. ]

Substituent group α is
Hydroxy group, nitro group, cyano group, halogen atom, lower alkoxy group, halogeno lower alkoxy group, carboxy group, lower alkoxycarbonyl group, carbamoyl group, lower acyloxy group, lower alkylthio group, halogeno lower alkylthio group and formula —NR ^d R a group having ^e (wherein R ^d and R ^e are the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, an aralkyl group, a lower alkylsulfonyl group or a lower alkylcarbonyl group; Or, together with the nitrogen atom to which R ^d and R ^e are bonded, forms a heterocyclyl group).

Substituent group β is
A lower alkyl group which may be substituted with a group selected from substituent group α,
A lower alkenyl group optionally substituted with a group selected from substituent group α,
An alkynyl group optionally substituted with a group selected from substituent group α,
Represents a group consisting of an aralkyl group and a cycloalkyl group;

Substituent group γ is
An oxo group, a hydroxyimino group, a lower alkoxyimino group, a lower alkylene group, a lower alkylenedioxy group, a lower alkylsulfinyl group and a lower alkylsulfonyl group;

Substituent group δ is
One group selected from the substituent group β;
A cycloalkyl group substituted with a group selected from substituent group α, substituent group β and substituent group γ;
An aryl group which may be substituted with a group selected from substituent group α, substituent group β and substituent group γ;
A heteroaryl group optionally substituted with a group selected from substituent group α, substituent group β and substituent group γ; and a group selected from substituent group α, substituent group β and substituent group γ The group which consists of the heterocyclyl group which may be substituted by is shown.

However, the atom on the ring A to which R ¹ and R ³ are bonded is adjacent to the atom on the ring A to which R ² is bonded. }.

Among these, suitable pharmaceutical compositions include
(2) In (1), A may be substituted with a pyrrole group which may be substituted with two groups selected from the substituent group δ and one group selected from the substituent group δ. A pharmaceutical composition which is a trivalent group selected from pyrazole groups;
(3) The pharmaceutical composition, wherein in (1), A is a pyrrole group optionally substituted with two groups selected from substituent group δ,
(4) The pharmaceutical composition in which A is a pyrrole group in (1),
(5) In any one item selected from (1) to (4), R ¹ is an aryl group optionally substituted with a group selected from substituent group α and substituent group β Composition,
(6) In any one item selected from (1) to (4), a phenyl group or a naphthyl group in which R ¹ may be substituted with a group selected from substituent group α and substituent group β A pharmaceutical composition,
(7) In any one item selected from (1) to (4), R ¹ is phenyl optionally substituted with a group selected from substituent group α ¹ and substituent group β ¹ ,
The substituent group α ¹ represents a group consisting of a hydroxy group, a cyano group, a halogen atom, a lower alkoxy group and a halogeno lower alkoxy group,
Substituent group beta ¹ is a pharmaceutical composition showing the group consisting of lower alkyl groups, halogeno-lower alkyl group and a hydroxy lower alkyl group,
(8) In any one item selected from (1) to (4), R ¹ is selected from phenyl, a hydroxy group, a cyano group, a halogen atom, a lower alkoxy group, a halogeno lower alkyl group, and a halogeno lower alkoxy group. A pharmaceutical composition which is a phenyl group substituted with a group selected from the group of substituents consisting of:
(9) In any one item selected from (1) to (4), R ¹ is phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 2 , 4-difluorophenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,4,5-trifluorophenyl, 3-chloro-4-fluorophenyl, 3-methoxyphenyl, 3-difluoromethoxyphenyl, 3, -Trifluoromethoxyphenyl,
A pharmaceutical composition which is a 3-trifluoromethylphenyl or 4-fluoro-3-methoxyphenyl group,
(10) In any one item selected from (1) to (4), R ¹ is phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3,4-difluoro. A phenyl, 3,4,5-trifluorophenyl, 3-chloro-4-fluorophenyl, 3-methoxyphenyl, 3-difluoromethoxyphenyl, 3-trifluoromethylphenyl or 4-fluoro-3-methoxyphenyl group; Pharmaceutical composition,
(11) In any one item selected from (1) to (4), R ¹ is phenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3,4-difluorophenyl, 3-chloro. A pharmaceutical composition which is a -4-fluorophenyl or 3-trifluoromethylphenyl group;
(12) In any one item selected from (1) to (11), R ² may be substituted with a group selected from the substituent group α and the substituent group β, and the nitrogen atom may be 1 Or a pharmaceutical composition which is a 5- to 6-membered heteroaryl group containing two,
(13) In any one item selected from (1) to (11), R ² may be a pyridyl group or a pyrimidinyl group optionally substituted with a group selected from substituent group α and substituent group β. A pharmaceutical composition,
(14) In any one item selected from (1) to (11), R ² may be a 4-pyridyl group which may be substituted with a group selected from substituent group α and substituent group β, or A pharmaceutical composition which is a 4-pyrimidinyl group,
(15) In any one item selected from (1) to (11), R ² may be substituted at the 2-position with one group selected from substituent group α and substituent group β A pharmaceutical composition which is a good 4-pyridyl group or 4-pyrimidinyl group,
(16) In any one item selected from (1) to (11), R ² is selected from the substituent group consisting of a methoxy, amino, methylamino, benzylamino, and α-methylbenzylamino group A pharmaceutical composition which is a 4-pyridyl group or a 4-pyrimidinyl group optionally substituted at the 2-position by two groups,
(17) In any one item selected from (1) to (16), a pharmaceutical composition in which m is 1.
(18) In any one item selected from (1) to (17), R ³ is a group having the formula (IIa), X is an alkylene group having 1 to 4 carbon atoms, and Y is a formula ^{C (R 8 a) (R} 8 b) group ^{(R 8} a and ^{R 8} b have the same or different, each represents a hydrogen atom, a hydroxy group, a halogen atom, having 1 to 4 alkyl groups or carbon A C 1-4 alkoxy group, R ⁸ a and R ⁸ b taken together to represent an oxo group or a methylene group, or a carbon to which R ⁸ a and R ⁸ b are bonded A pharmaceutical composition comprising a 3- to 6-membered cycloalkyl group together with the atoms).
(19) In any one item selected from (1) to (17), R ³ is a group having the formula (IIa), X is a methylene group, and Y is a formula C (R ⁸ a) ( R ⁸ b) group ^{(R 8} a and ^{R 8} b have the same or different, each represents a hydrogen atom, a hydroxy group, a fluorine atom, a methyl group, an ethyl group, or shows a methoxy group or ethoxy group, ^{R 8} a and R ⁸ b together represent an oxo group or a methylene group, or together with the carbon atom to which R ⁸ a and R ⁸ b are bonded, form a cyclopropyl group A pharmaceutical composition which is
(20) In any one item selected from (1) to (17), R ³ is a group having the formula (IIa), X is a methylene group, and Y is a formula C (R ⁸ a) ( A pharmaceutical composition which is a group having R ⁸ b) (R ⁸ a and R ⁸ b are the same or different and each represents a hydrogen atom, a fluorine atom, a methyl group, a hydroxy group or an oxo group);
(21) In any one item selected from (1) to (17), R ³ is a group having the formula (IIa), X is a methylene group, and Y is a group having the formula CH ₂ Pharmaceutical composition,
(22) In any one item selected from (1) to (17), R ³ is a group having the formula (IIb), the ring B contains one nitrogen atom, a nitrogen atom, oxygen 5- or 6-membered heterocyclyl ring optionally containing one atom or group selected from the group consisting of atoms, sulfur atoms, groups having the formula> SO and groups having the formula> SO ₂ Or an unsaturated group; which may be condensed with an aryl group, heteroaryl group, cycloalkyl group or heterocyclyl group).
(23) In any one item selected from (1) to (17), R ³ is a group having the formula (IIb), and Ring B is a 5- or 6-membered heterocyclyl ring containing one nitrogen atom (The ring is saturated or unsaturated; it may be condensed with an aryl group, heteroaryl group, cycloalkyl group or heterocyclyl group),
(24) The pharmaceutical composition according to any one selected from (1) to (17), wherein R ³ is a group having the formula (IIb), and ring B is pyrrolidine or pyrroline,
(25) In any one item selected from (1) to (24), Z is a phenylene group, a thiophenediyl group, a furandiyl group, a pyrrolediyl group, an oxazolediyl group, a thiazolediyl group, a thiadiazolediyl group or pyridine. A pharmaceutical composition which is a diyl group,
(26) The pharmaceutical composition according to any one of (1) to (24), wherein Z is a phenylene group or a thiophenediyl group,
(27) In any one item selected from (1) to (26),
R ⁵ is a group having the formula CONR ^a R ^b , a group having the formula COR ^c , a group having the formula SO ₂ NR ^a R ^b , a group having the formula SO ₂ R ^c or a group having the formula SOR ^c (wherein R ^a and R ^b are the same or different and each represents a hydrogen atom,
A lower alkyl group which may be substituted with a group selected from substituent group α,
A lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group,
Represents an amino group or a mono- or di-lower alkylamino group,
R ^c represents a lower alkyl group. A pharmaceutical composition which is
(28) In any one item selected from (1) to (26),
R ⁵ is a group having the formula CONR ^a R ^b , a group having the formula SO ₂ NR ^a R ^b , a group having the formula SO ₂ R ^c or a group having the formula SOR ^c (wherein R ^a and R ^b are The same or different, a hydrogen atom, a lower alkyl group, a halogeno lower alkyl group, a hydroxy lower alkyl group, a lower alkoxy lower alkyl group, a lower alkoxy group or a cycloalkyl group;
R ^c represents a lower alkyl group. A pharmaceutical composition which is
(29) In any one item selected from (1) to (26),
R ⁵ is carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-cyclopropylcarbamoyl, N-cyclopentylcarbamoyl, N- (2-fluoroethyl) carbamoyl, N- ( 2-methoxyethyl) carbamoyl,
N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-cyclopropylsulfamoyl, N-cyclopentylsulfamoyl, N- (2-fluoroethyl) ) Sulfamoyl, N- (2-methoxyethyl) sulfamoyl, N-methoxysulfamoyl,
Methanesulfonyl, ethanesulfonyl, propanesulfonyl,
A pharmaceutical composition which is a methanesulfinyl, ethanesulfinyl or propanesulfinyl group,
(30) In any one item selected from (1) to (29),
A pharmaceutical composition, wherein R ⁶ is 1 to 2 groups selected from the group consisting of a hydrogen atom, a fluorine atom and a methoxy group;
(31) The pharmaceutical composition according to any one item selected from (1) to (29), wherein R ⁶ is a hydrogen atom,
(32) The pharmaceutical composition according to any one of (1) to (31), wherein R ⁷ is 1 to 2 groups selected from the group consisting of a hydrogen atom, a hydroxy group, and a lower alkyl group. object,
(33) The pharmaceutical composition according to any one item selected from (1) to (31), wherein R ⁷ is a hydrogen atom,
(34) In any one item selected from (1) to (33), the compound having the general formula (I) is represented by any one of the following general formulas:

(Wherein R ⁴ and R ⁴ ′ are the same or different and represent a hydrogen atom or a group selected from substituent group δ) and (35) any one selected from (1) to (33) 1. The pharmaceutical composition wherein the compound having the general formula (I) is represented by any one of the following general formulas:

(Wherein R ⁴ and R ⁴ ′ are the same or different and each represents a hydrogen atom or a group selected from the substituent group δ).

Furthermore, in a pharmaceutical composition comprising as an active ingredient a compound having the general formula (I) described in (1) above or a pharmacologically acceptable salt thereof,
(2) to (4); (5) to (11); (12) to (16); (17); (18) to (21); (25) to (26); (27) to (29) ); (30) to (31); (32) to (33); and (34) to (35) a pharmaceutical composition satisfying a combination of requirements arbitrarily selected from the group consisting of 10 and (35); (2) to (4); (5) to (11); (12) to (16); (17); (22) to (24); (25) to (29); (30) to (31) Also suitable are pharmaceutical compositions that satisfy a combination of optional requirements arbitrarily selected from the 10 groups consisting of (32) to (33); and (34) to (35).

More preferably,
(36) A pharmaceutical composition according to (1), wherein the compound having general formula (I) is selected from:
4- [1- (4-Carbamoylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole ,
3- [1- (4-Carbamoylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -5- (4-fluorophenyl) -4- (pyridin-4-yl) -1H-pyrazole ,
2- (4-Fluorophenyl) -4- [1- [4- (N-methylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole,
4- [1- [4- (N-ethylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) ) -1H-pyrrole,
4- [1- [4- (N-cyclopropylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4- Yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-isopropylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-propylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole,
4- [1- [4- [N- (2-Fluoroethyl) carbamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- ( Pyridin-4-yl) -1H-pyrrole,
4- [1- [4- (N-cyclopentylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) ) -1H-pyrrole,
4- [1- [4- [N- (Ethoxycarbonylmethyl) carbamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine -4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole,
4- [1- [4- (N-ethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4 -Yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-propylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-isopropylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole,
2- (3-Chloro-4-fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (Pyridin-4-yl) -1H-pyrrole,
4- [1- [4- (N-cyclopropylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine- 4-yl) -1H-pyrrole,
4- [1- [4- [N- (2-fluoroethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- ( Pyridin-4-yl) -1H-pyrrole,
4- [1- [4- (N, N-dimethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine -4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- [N- (2-methoxyethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- ( Pyridin-4-yl) -1H-pyrrole,
4- [1- [4- (N-ethoxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4 -Yl) -1H-pyrrole,
4- [1- [4- (N-allyloxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine- 4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- (4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H- Pyrrole,
2- (3-Chloro-4-fluorophenyl) -4- [1- (4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl ) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- (4-methanesulfinylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H- Pyrrole,
2- (3-Chloro-4-fluorophenyl) -4- [1- (4-methanesulfinylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4yl) -1H-pyrrole,
4- [1- (4-Acetylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
2- (3-Chloro-4-fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-methylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydro Indolizine-7-yl] -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- (4-carbamoylphenyl) -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4-fluorophenyl) -3 -(Pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-methylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- [4- (N-ethylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4- Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- [4- (N-benzylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4- Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- [4- (N-cyclopropylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4 -Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- [4- [N- (2-fluoroethyl) carbamoyl] phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl]- 2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-propylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-isopropylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- [N- (2-methoxyethyl) carbamoyl] phenyl] -1,2,3,5,6,8a-hexa Hydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (2-methoxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4- Yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (2-hydroxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4- Yl) -1H-pyrrole,
2- (3-Chloro-4-fluorophenyl) -4- [1- [4- (2-methoxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- ( Pyridin-4-yl) -1H-pyrrole and 2- (3-chloro-4-fluorophenyl) -4- [1- [4- (2-hydroxyethyl) sulfonylphenethyl] -1,2,3,6- Tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole.

The above pharmaceutical composition is:
(37) used to suppress the production of inflammatory cytokines,
Particularly preferably,
(38) An antipyretic / analgesic agent having an inhibitory action on the production of inflammatory cytokines (39) an anti-inflammatory agent,
(40) Rheumatoid arthritis preventive or therapeutic agent,
(41) Preventive or therapeutic agent for osteoarthritis,
(42) preventive or therapeutic agent for allergic diseases,
(43) Osteoporosis preventive or therapeutic agent,
(44) preventive or therapeutic agent for arteriosclerosis,
(45) Tumor preventive or therapeutic agent,
(46) a prophylactic or therapeutic agent for ischemic heart disease,
(47) Used as a preventive or therapeutic agent for sepsis, psoriasis, Crohn's disease, ulcerative colitis, diabetes or hepatitis.

Another object of the present invention is to
(48) Providing the use of the compound described in any one of (1) to (36) or a pharmacologically acceptable salt thereof for producing a pharmaceutical composition,
And an effective amount of the compound described in any one of (1) to (36) or a pharmacologically acceptable salt thereof is administered to a warm-blooded animal (preferably a human), (I) a method for suppressing the production of inflammatory cytokines, (ii) a method for preventing or treating a disease involving inflammatory cytokines [preferably a method for treating or removing heat, pain and / or inflammation; rheumatoid arthritis, deformity Prevention or treatment of osteoarthritis, allergic disease, osteoporosis, arteriosclerosis, tumor, ischemic heart disease, sepsis, psoriasis, Crohn's disease, ulcerative colitis, diabetes (especially type I diabetes) or hepatitis]
Is to provide.

  The pharmaceutical composition containing the cyclic tertiary amine compound of the present invention has excellent inflammatory cytokine production inhibitory action, good oral absorption, and low toxicity, so that inflammatory cytokine is mediated. It is useful as a preventive or therapeutic agent for warm-blooded animals (especially for humans). Such pharmaceutical compositions include, for example, antipyretic / analgesic / anti-inflammatory agents, antiviral agents, and rheumatoid arthritis, osteoarthritis, allergic diseases, asthma, sepsis, psoriasis, osteoporosis, autoimmune diseases (eg, systemic Erythematosus, ulcerative colitis, Crohn's disease, etc.), diabetes (especially type I diabetes), nephritis, hepatitis, tumor, ischemic heart disease, Alzheimer's disease or arteriosclerosis, preferably Antipyretic / analgesic / anti-inflammatory agent and rheumatoid arthritis, osteoarthritis, allergic disease, sepsis, psoriasis, osteoporosis, ulcerative colitis, diabetes (especially type I diabetes), hepatitis, arteriosclerosis or clone Particularly preferred are antipyretic, analgesic and anti-inflammatory agents, and rheumatoid arthritis, osteoarthritis, sepsis, psoriasis, Crohn's disease, ulcerative colitis, diabetes ( In type I diabetes) or hepatitis prophylactic or therapeutic agents.

  The compound having the above general formula (I) represents one of the following general formulas:

  Among the compounds represented by the above general formula, suitable compounds have any of the following general formulas:

  Among the compounds represented by the above general formula, more preferable compounds have the following general formula:

(In the formula, R ¹ , R ² , R ³ , R ⁴ and R ⁴ ′ are as defined above).

In the above general formula (I), R ³ represents a group having the following general formula (IIa) or (IIb):

(In the formula, B, X, Y, Z, R ⁵ , R ⁶ , R ⁷ , m and n are as defined above).

  Among the groups represented by the above general formula, m is preferably a group of 1.

In the general formula (IIa), preferably, X is an alkylene group having 1 to 4 carbon atoms, and Y is a group (R ⁸ a and R having the formula C (R ⁸ a) (R ⁸ b)). ⁸ b is the same or different and each represents a hydrogen atom, a hydroxy group, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, or R ⁸ a and R ⁸ b Together represent an oxo group or a methylene group, or together with the carbon atom to which R ⁸ a and R ⁸ b are bonded, a 3- to 6-membered cycloalkyl group is formed. More preferably, X is a methylene group and Y is a group having the formula C (R ⁸ a) (R ⁸ b) (R ⁸ a and R ⁸ b are the same or Differently, hydrogen atom, hydroxy group, fluorine atom, methyl group, ethyl Group, or shows a methoxy group or ethoxy group, R 8 ^a and R ^{8 b} are taken together or represent oxo group or methylene group, or a carbon atom to which R 8 ^a and R ^{8 b} are attached And more preferably a group having the formula C (R ⁸ a) (R ⁸ b), wherein X is a methylene group. (R ⁸ a and R ⁸ b are the same or different and each represents a hydrogen atom, a fluorine atom, a methyl group, a hydroxy group or an oxo group), and particularly preferably X is a methylene group. And Y is a group having the formula C (R ⁸ a) (R ⁸ b) (R ⁸ a and R ⁸ b are the same or different and each represents a hydrogen atom, a fluorine atom or a hydroxy group). And most preferably X is a methylene group. There is a group a group, i.e. a methylene group having the formula CH _2.

In the above general formula (IIb), preferably, ring B contains one nitrogen atom, and further includes a nitrogen atom, an oxygen atom, a sulfur atom, a group having the formula> SO and a group having the formula> SO _2. A 5- or 6-membered heterocyclyl ring optionally containing one atom or group selected from the group (wherein the ring is saturated or unsaturated; an aryl group, heteroaryl group, cycloalkyl group or More preferably a 5- or 6-membered heterocyclyl ring wherein the ring B contains one nitrogen atom (the ring is saturated or unsaturated). An aryl group, a heteroaryl group, a cycloalkyl group or a heterocyclyl group), and more preferably a group in which Ring B is a pyrrolidine ring or a pyrroline ring. is there.

In the general formula (I),
“Aryl group” in the definition of R ^a , R ^b and ring B; “aryl group” of “aryl group optionally substituted with a group selected from substituent group α and substituent group β” in the definition of R ¹ In the definition of [Substituent group δ], the “aryl group” of “aryl group optionally substituted with a group selected from substituent group α, substituent group β and substituent group γ” is, for example, An aryl group having 6 to 14 carbon atoms such as a phenyl, naphthyl, phenanthryl or anthracenyl group, preferably a phenyl group or a naphthyl group, and most preferably a phenyl group.

  The “aryl group” may be condensed with a cycloalkyl group having 3 to 10 carbon atoms, and such a group is, for example, a 5-indanyl group.

  The “arylene group” in the definition of Z is, for example, an arylene group having 6 to 14 carbon atoms such as phenylene, naphthalenediyl, phenanthrenediyl or anthracenediyl group, preferably a phenylene or naphthalenediyl group, Optimally, it is a phenylene group.

The “aryl group optionally substituted with a group selected from substituent group α and substituent group β” in the definition of R ¹ is preferably 1 selected from substituent group α and substituent group β. An aryl group which may be substituted with 1 to 4 groups, and more preferably an aryl group which may be substituted with 1 to 3 groups selected from substituent group α and substituent group β And more preferably a phenyl group which may be substituted with 1 to 3 groups selected from substituent group α and substituent group β.

  Preferred examples are phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl. 3,4,5-trifluorophenyl, 3-chloro-4-fluorophenyl, 3-methoxyphenyl, 3-difluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 3-trifluoromethylphenyl or 4-fluoro-3 -Methoxyphenyl group, and more preferable specific examples are phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3,4-difluorophenyl, 3,4,5-trifluoro. Phenyl, 3-chloro-4-fluorophenyl, 3-methoxy A phenyl group, a 3-difluoromethoxyphenyl group, a 3-trifluoromethylphenyl group, a 3-cyanophenyl group, or a 4-fluoro-3-methoxyphenyl group; A phenyl, 3-chlorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl or 3-trifluoromethylphenyl group;

  The “aryl group optionally substituted with a group selected from substituent group α, substituent group β and substituent group γ” in the definition of [substituent group δ] is preferably a substituent group α, An aryl group which may be substituted with 1 to 4 groups selected from substituent group β and substituent group γ, and more preferably, substituent group α, substituent group β and substituent group γ. An aryl group which may be substituted with 1 to 3 groups selected from the group consisting of “lower alkylthio group”, “halogeno lower alkylthio group”, “lower alkylsulfinyl group” and “lower An aryl group optionally substituted with one group selected from "alkylsulfonyl group". Suitable examples thereof include phenyl, 4-methylthiophenyl, 4-ethylthiophenyl, 4-propylthiophenyl, 4-methylsulfinylphenyl, 4-ethylsulfinylphenyl, 4-propylsulfinylphenyl, 4-methanesulfonylphenyl, 4-ethanesulfonylphenyl or 4-propanesulfonylphenyl group.

“Heteroaryl group” in the definition of R ^a , R ^b and ring B; “heteroaryl group optionally substituted with a group selected from substituent group α and substituent group β” in the definition of R ¹ "Heteroaryl group"; and "heteroaryl group substituted with a group optionally selected from substituent group α, substituent group β and substituent group γ" in the definition of [substituent group δ] `` Aryl group '' means, for example, a sulfur atom, oxygen atom and / or Or a 5- to 7-membered heteroaryl group containing 1 to 4 nitrogen atoms, preferably furyl, thie 5- to 6-membered hetero, containing 1 or 2 sulfur atoms, oxygen atoms and / or nitrogen atoms, such as nyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl groups An aryl group, more preferably a furyl, thienyl, pyridyl or pyrimidinyl group.

  The “heteroaryl group” may be condensed with another cyclic group (for example, an aryl group or a cyclic group such as a cycloalkyl group having 3 to 10 carbon atoms). The group is, for example, an indolyl, benzofuranyl, benzothienyl, quinolyl, isoquinolyl, quinazolinyl, tetrahydroquinolyl or tetrahydroisoquinolyl group.

  “Heteroarylene group” in the definition of Z includes, for example, thiophene diyl, furandyl, pyrrole diyl, pyrazole diyl, imidazole diyl, oxazole diyl, isoxazole diyl, thiazole diyl, isothiazole diyl, triazole diyl, tetrazole diyl, thiadiazole diyl A 5- to 7-membered heteroarylene group containing 1 to 4 sulfur atoms, oxygen atoms and / or nitrogen atoms, such as pyridinediyl, pyridazinediyl, pyrimidinediyl or pyrazinediyl group, preferably thiophenediyl, flange 5- to 6-membered heteroarylene groups containing 1 or 3 sulfur atoms, oxygen atoms and / or nitrogen atoms, such as yl, pyridinediyl, pyrimidinediyl, thiazoldiyl or thiadiazolediyl groups , More preferably a thiophenediyl or pyridinediyl group, particularly preferably a thiophenediyl group.

The “heteroaryl group optionally substituted with a group selected from substituent group α and substituent group β” in the definition of R ¹ is preferably selected from substituent group α and substituent group β. A heteroaryl group which may be substituted with 1 to 3 groups, and more preferably 1 to 2 groups selected from substituent group α and substituent group β. A heteroaryl group; Suitable examples thereof include furyl, thienyl, pyridyl, pyrimidinyl, 5-fluoro-2-furyl, 4-chloro-2-thienyl, 5-difluoromethoxy-3-furyl, 5-trifluoromethyl-3-thienyl or 5-Fluoro-2-oxazolyl group.

  The “heteroaryl group optionally substituted with a group selected from substituent group α, substituent group β and substituent group γ” in the definition of [Substituent group δ] is preferably substituent group α , A heteroaryl group which may be substituted with 1 to 3 groups selected from substituent group β and substituent group γ, more preferably substituent group α, substituent group β and substituent A heteroaryl group which may be substituted with 1 to 2 groups selected from the group γ. Preferred examples thereof include the above-mentioned “heteroaryl group”, 2-methylthio-5-pyridyl, 3-methylthio-6-pyridazinyl, 2-methylthio-5-pyrimidinyl, 2-methylsulfinyl-5-pyridyl, 3-methyl Sulfinyl-6-pyridazinyl, 2-methylsulfinyl-5-pyrimidinyl, 2-methanesulfonyl-5-pyridyl, 3-methanesulfonyl-6-pyridazinyl or 2-methanesulfonyl-5-pyrimidinyl group.

In the definition of R ² , “hetero having at least one nitrogen atom” in “heteroaryl group having at least one nitrogen atom which may be substituted with a group selected from substituent group α and substituent group β” An “aryl group” includes at least one nitrogen atom, such as a pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, tetrazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl group, and further 1 to 3 A 5- to 7-membered heteroaryl group optionally containing 1 sulfur atom, oxygen atom and / or nitrogen atom, preferably pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyridazinyl, Pyrimidinyl Is a 5- to 6-membered heteroaryl group containing one nitrogen atom and further containing one sulfur atom, oxygen atom or nitrogen atom, such as pyrazinyl group, more preferably imidazolyl, pyridyl , A pyridazinyl, pyrimidinyl or pyrazinyl group, such as a 5- to 6-membered heteroaryl group containing 1 to 2 nitrogen atoms, particularly preferably a pyridyl or pyrimidinyl group, most preferably 4-pyridyl or 4 -A pyrimidinyl group.

The “heteroaryl group having at least one nitrogen atom which may be substituted with a group selected from substituent group α and substituent group β” in the definition of R ² preferably includes substituent group α and A group which may be substituted with 1 to 3 groups selected from substituent group β, and more preferably 1 to 2 groups selected from substituent group α and substituent group β. A group that may be substituted, and even more preferably a group that may be substituted with one group selected from substituent group α and substituent group β. 2-position with one group selected from group α and substituent group β may be substituted, a 4-pyridyl or 4-pyrimidinyl, most preferably, having the formula -NR ^d R ^e group (wherein, R ^d and R ^e are the same or different, each represent a hydrogen atom, a lower alkyl , A lower alkenyl group, lower alkynyl group, or an aralkyl group, or a lower alkylsulfonyl group, or, together with the nitrogen atom to which R ^d and R ^e are bonded to form a heterocyclyl group.) And the formula The 2-position is substituted with one group selected from a lower alkyl group optionally substituted with a group having —NR ^d R ^e (wherein R ^d and R ^e are as defined above). 4-pyridyl or 4-pyrimidinyl, which may be Suitable examples thereof include 4-pyridyl, 4-pyrimidinyl, 2-amino-4-pyridyl, 2-amino-4-pyrimidinyl, 2-methylamino-4-pyridyl, 2-methylamino-4-pyrimidinyl, 2 -Methoxy-4-pyridyl, 2-methoxy-4-pyrimidinyl, 2-benzylamino-4-pyridyl, 2-benzylamino-4-pyrimidinyl or 2- (α-methylbenzylamino) -4-pyridyl or 2- ( α-methylbenzylamino) -4-pyrimidinyl group.

The “lower alkyl group substituted with a heteroaryl group” in the definition of R ^a and R ^{b is} a group in which the above “heteroaryl group” is substituted with a lower alkyl group, preferably the above “heteroaryl group” Is a group substituted with an alkyl group having 1 to 4 carbon atoms, and more preferably, the “heteroaryl group” is a group substituted with an alkyl group having 1 to 2 carbon atoms. Suitable examples thereof include (2 or 3-furyl) methyl, 2- (2 or 3-furyl) ethyl, (2 or 3-thienyl) methyl, 2- (2 or 3-thienyl) ethyl, (2, 3 or 4-pyridyl) methyl, 2- (2,3 or 4-pyridyl) ethyl, (2,4 or 5-pyrimidinyl) methyl or 2- (2,4 or 5-pyrimidinyl) ethyl.

“Cycloalkyl group” in the definition of R ^a , R ^b , ring B and [substituent β]; “cycloalkyl group” in the definition of R ⁸ a and R ⁸ b; and “substituent group δ” in the definition of “substituent group δ” The “cycloalkyl group” of the cycloalkyl group substituted with a group selected from the substituent group α, the substituent group β and the substituent group γ is a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group. A cycloalkyl group having 3 to 7 carbon atoms, preferably a cycloalkyl group having 3 to 6 carbon atoms, and more preferably a cyclopropyl, cyclopentyl, or cyclohexyl group.

The “lower alkyl group substituted with a cycloalkyl group” in the definition of R ^a and R ^{b represents} a group in which the above “cycloalkyl group” is substituted with a lower alkyl group, preferably the above “cycloalkyl group”. Is a group substituted with an alkyl group having 1 to 4 carbon atoms, and more preferably, the “cycloalkyl group” is a group substituted with an alkyl group having 1 to 2 carbon atoms. Preferred examples thereof are cyclopropylmethyl, 2-cyclopropylethyl, cyclopentylmethyl, 2-cyclopentylethyl, cyclohexylmethyl or 2-cyclohexylethyl group.

  1 to 3 “heterocyclyl groups” in “heterocyclyl group optionally substituted with a group selected from substituent group α, substituent group β, and substituent group γ” in the definition of [Substituent Group δ] 4 to 7-membered heterocyclyl group having a sulfur atom, an oxygen atom and / or a nitrogen atom, and preferably a 4 to 7-membered heterocyclyl group containing 1 or 2 sulfur atom, oxygen atom and / or nitrogen atom More preferably, it is a 5- or 6-membered heterocyclyl group containing one nitrogen atom and further containing one oxygen atom, sulfur atom or one nitrogen atom. Pyrrolidinyl, pyrrolinyl, imidazolidinyl, imidazolinyl, pyrazolidinyl, pyrazolinyl, oxazolidinyl, thiazolidinyl, piperidyl, tetrahydropyridyl, dihydropyridyl, Perajiniru, morpholinyl, thiomorpholinyl or homopiperidyl group.

The heterocyclyl group formed by R ^d and R ^{e of the} group having the formula —NR ^d R ^e included in [Substituent group α] together with the nitrogen atom to which they are bonded has one nitrogen atom A 4- to 7-membered heterocyclyl group which may further contain one oxygen atom, sulfur atom or nitrogen atom, for example, 1-azetidinyl, 1-pyrrolidinyl, 1-pyrrolinyl, 1-imidazolidinyl, 1-imidazolinyl 1-pyrazolidinyl, 1-pyrazolinyl, 3-oxazolidinyl, 3-thiazolidinyl, 1-piperidyl, tetrahydropyridin-1-yl, dihydropyridin-1-yl, 1-piperazinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-homopiperidyl 8-azabicyclo [3.2.1] octane-8-yl, 8-azabicyclo [3.2.1] It is an octen-8-yl, 9-azabicyclo [3.3.1] nonane-9-yl or 9-azabicyclo [3.3.1] nonen-9-yl group.

  These groups may be condensed with an aryl group or a heteroaryl group, and such a group is, for example, a tetrahydroquinolin-1-yl or tetrahydroisoquinolin-2-yl group.

In the definition of ring B, "4 to 7 membered heterocyclyl ring", 2 is selected from the group consisting of radicals having carbon atoms, a nitrogen atom, an oxygen atom, a sulfur atom, a group and the formula> SO ₂ having the formula> SO Means a 4- to 7-membered heterocyclyl ring consisting of from 5 to 5 atoms or groups, and is a 4- to 7-membered heterocyclyl ring containing at least one nitrogen atom (ie, a saturated or unsaturated heterocyclyl ring); Preferably, one atom or group containing one nitrogen atom and further selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a group having the formula> SO and a group having the formula> SO ₂ 5 or 6-membered heterocyclyl ring, which may contain pyrrolidine, pyrroline, imidazolidine, imidazoline, pyrazolidine, pyrazoline, oxazolidine, Azolidine, piperidine, and tetrahydropyridine, dihydropyridine, piperazine, morpholine or thiomorpholine ring, more preferably more, pyrrolidine, a pyrroline or imidazoline ring, particularly preferably a pyrrolidine ring or a pyrroline ring.

  The “heterocyclyl ring” may be condensed with the “aryl group”, the “heteroaryl group”, the “cycloalkyl group” or the “heterocyclyl group”. , Tetrahydroquinoline, octahydroquinoline, decahydroquinoline, tetrahydroisoquinoline, octahydroisoquinoline, decahydroisoquinoline, indoline, octahydroindole, isoindoline or octahydroisoindole ring.

The “halogen atom” in the definition of R ⁶ , R ⁷ , R ⁸ a, R ⁸ b and [substituent group α] can be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom Or it is a chlorine atom.

“Lower alkyl group” in the definition of R ⁶ , R ⁷ , R ⁸ a, R ⁸ b, R ^c , R ^d and R ^e ; and “substitution in the definition of R ^a , R ^b and [substituent group β]” The “lower alkyl group” of the “lower alkyl group optionally substituted with a group selected from the group α” is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, tert-butyl, pentyl, isopentyl. 2-methylbutyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, Such as 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl or 2-ethylbutyl groups It may be a linear or branched alkyl group having 1 to 6 prime atoms, preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl, ethyl, propyl, isopropyl or butyl group. Particularly preferred are methyl, ethyl or propyl groups.

“Lower alkyl group optionally substituted with a group selected from substituent group α” in the definition of R ^a , R ^b and [Substituent group β] is one to two of the above-mentioned “lower alkyl groups” The above hydrogen atom represents a group which may be substituted with a group selected from [Substituent group α]. Preferably, it represents a lower alkyl group which may be substituted with 1 to 3 groups selected from [Substituent Group α], more preferably 1 to 1 selected from [Substituent Group α]. A lower alkyl group which may be substituted with two groups, and more preferably a C 1 to C group which may be substituted with 1 to 2 groups selected from [Substituent group α]. 4 alkyl groups, particularly preferably a methyl, ethyl, propyl or isopropyl group, the chain end of which may be substituted with 1 to 2 groups selected from [Substituent group α] .

Preferred examples thereof include the above-mentioned “lower alkyl group”, hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl, 1,3-dihydroxyisopropyl, cyanomethyl, 2-cyanoethyl, fluoromethyl, 2-fluoroethyl, 3- Fluoropropyl, chloromethyl, 2-chloroethyl, 3-chloropropyl, methoxymethyl, 2-methoxyethyl, 3-methoxypropyl, ethoxymethyl, 2-ethoxyethyl, 3-ethoxypropyl, fluoromethoxymethyl, difluoromethoxymethyl, tri Fluoromethoxymethyl, 2-fluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl,
Carboxymethyl, 2-carboxyethyl, 3-carboxypropyl,
Methoxycarbonylmethyl, 2- (methoxycarbonyl) ethyl, ethoxycarbonylmethyl, 2- (ethoxycarbonyl) ethyl,
Carbamoylmethyl, 2-carbamoylethyl, 3-carbamoylpropyl,
Acetoxymethyl,
Methylthiomethyl, 2-methylthioethyl, 3-methylthiopropyl,
Fluoromethylthiomethyl, difluoromethylthiomethyl, trifluoromethylthiomethyl, 2-fluoromethylthioethyl, 2-difluoromethylthioethyl, 2-trifluoromethylthioethyl,
Aminomethyl, methylaminomethyl, dimethylaminomethyl, 2-aminoethyl, 2-methylaminoethyl, 2-dimethylaminoethyl, 3-aminopropyl, 3-methylaminopropyl or 3-dimethylaminopropyl group, more preferred Specific examples are methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl, 2-fluoroethyl, 2-methoxyethyl or 2-dimethylaminoethyl group.

“Lower alkenyl group” in the definition of R ^d and R ^e ; and “lower alkenyl optionally substituted with a group selected from substituent group α” in the definition of R ^a , R ^b and [substituent group β] The “lower alkenyl group” of “group” means vinyl, 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-ethyl-2-propenyl, 2-butenyl, 1-methyl-2- Butenyl, 2-methyl-2-butenyl, 1-ethyl-2-butenyl, 3-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 1-ethyl-3-butenyl, 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 And a straight or branched alkenyl group having 2 to 6 carbon atoms such as 2-methyl-4-pentenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl group, and preferably , An alkenyl group having 2 to 4 carbon atoms, and more preferably an alkenyl group having 3 or 4 carbon atoms.

“Lower alkynyl group” in the definition of R ^d and R ^e ; and “lower alkynyl optionally substituted with a group selected from substituent group α” in the definition of R ^a , R ^b and [substituent group β] The “lower alkynyl group” in the “group” means ethynyl, 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 1-methyl-2-butynyl, 1-ethyl-2-butynyl, 3-butynyl, 1- Methyl-3-butynyl, 2-methyl-3-butynyl, 1-ethyl-3-butynyl, 2-pentynyl, 1-methyl-2-pentynyl, 3-pentynyl, 1-methyl-3-pentynyl, 2-methyl- Such as 3-pentynyl, 4-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl or 5-hexynyl group Be a prime number 2 to 6 straight-chain or branched-chain alkynyl group, preferably a number of 2 to 4 carbon alkynyl group having a carbon, and more preferably a number of 3 or 4 alkynyl group having a carbon.

  The “lower alkylene group” in the definition of [Substituent group γ] is methylene, ethylene, trimethylene, propylene, tetramethylene, 1-methyltrimethylene, 2-methyltrimethylene, 1,1-dimethylethylene, pentamethylene, 1 , 1-dimethyltrimethylene, 2,2-dimethyltrimethylene, 1,2-dimethyltrimethylene or a hexamethylene group, a straight or branched alkylene group having 1 to 6 carbon atoms, preferably A linear or branched alkylene group having 1 to 4 carbon atoms, and more preferably a methylene, ethylene, trimethylene, propylene, or tetramethylene group.

  The “linear or branched alkylene group having 1 to 5 carbon atoms” in the definition of X is preferably a linear or branched alkylene group having 1 to 4 carbon atoms, and more preferably a methylene group. It is.

The “aralkyl group” in the definition of R ^a , R ^b , R ^d , R ^e and [substituent group β] may be a group in which the “aryl group” is bonded to the “lower alkyl group”. Examples of the group include benzyl, α-naphthylmethyl, β-naphthylmethyl, 1-phenethyl, 2-phenethyl, 2- (α-naphthyl) ethyl, 2- (β-naphthyl) ethyl, 3-phenylpropyl, 4-phenyl A phenylbutyl, 5-phenylpentyl or 6-phenylhexyl group, preferably benzyl.

  The aryl part of the “aralkyl group” may be substituted with 1 to 3 groups selected from the “substituent group α” and the “substituent group β”, and such a substituent is substituted. The aralkyl group is preferably 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-methylbenzyl, 3-methylbenzyl, 4- An aralkyl group substituted with a halogen atom, a lower alkyl group or a lower alkoxy group such as methylbenzyl, 2-methoxybenzyl, 3-methoxybenzyl or 4-methoxybenzyl group.

  Among the “aralkyl group” and the substituted aralkyl group, preferably an unsubstituted aralkyl group or an aralkyl group substituted with a halogen atom, a lower alkyl group or a lower alkoxy group, and more preferably an unsubstituted aralkyl group. Or an aralkyl group substituted with a halogen atom or a lower alkyl group, and most preferably an unsubstituted aralkyl group.

The “hydroxy lower alkyl group” in the definition of R ^c is a group obtained by substituting one or more hydrogen atoms of the above “lower alkyl group” with a hydroxy group, preferably having 1 to 4 carbon atoms. For example, a hydroxymethyl group, a 2-hydroxyethyl group, or a 3-hydroxypropyl group.

"Halogeno-lower alkyl group" in the definition of R ^6, R ⁷ and R ^e are one or two or more hydrogen atoms have been substituted with the aforementioned "halogen atom" group of the above "lower alkyl group", preferably Is a halogeno lower alkyl group having 1 to 4 carbon atoms, and more preferably trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, dibromomethyl, fluoromethyl, 2,2,2-trichloroethyl, 2 , 2,2-trifluoroethyl, 2-bromoethyl, 2-chloroethyl, 2-fluoroethyl, 2,2-dibromoethyl, and more preferably trifluoromethyl, trichloromethyl, difluoromethyl, fluoromethyl. And most preferred is trifluoromethyl.

“Lower alkoxy group” in the definition of R ⁶ , R ⁷ , R ⁸ a, R ⁸ b, R ^a , R ^b and [Substituent group α] is a group in which an oxygen atom is bonded to the “lower alkyl group”. And preferably a linear or branched alkoxy group having 1 to 4 carbon atoms, and more preferably a methoxy, ethoxy, propoxy or isopropoxy group.

The “halogeno lower alkoxy group” in the definition of R ⁶ , R ⁷ and [substituent group α] is a group in which one or two or more hydrogen atoms of the “lower alkoxy group” are substituted with the above “halogen atom”. Is preferably a halogeno lower alkoxy group having 1 to 4 carbon atoms, more preferably a difluoromethoxy, trifluoromethoxy or 2,2,2-trifluoroethoxy group, and particularly preferably Difluoromethoxy group.

The “lower alkoxy lower alkyl group” in the definition of R ^c is a group in which one or more hydrogen atoms of the above “lower alkyl group” are substituted with the above “lower alkoxy group”. Examples of the alkoxyalkyl group include several to four, for example, methoxymethyl, 1,1-dimethyl-1-methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, butoxymethyl, and t-butoxymethyl.

The “lower alkylthio group” in the definition of R ⁶ , R ⁷ and [Substituent group α] is a group in which a sulfur atom is bonded to the above-mentioned “lower alkyl group”, preferably a straight chain having 1 to 4 carbon atoms. It is a chain or branched alkylthio group, more preferably a methylthio, ethylthio, propylthio, isopropylthio or butylthio group, and particularly preferably a methylthio, ethylthio or propylthio group.

The “halogeno lower alkylthio group” in the definition of R ⁶ , R ⁷ and [Substituent group α] is a group in which one or more hydrogen atoms of the above “lower alkylthio group” are substituted with the above “halogen atom”. And preferably a halogeno lower alkylthio group having 1 to 4 carbon atoms, more preferably a difluoromethylthio, trifluoromethylthio or 2,2,2-trifluoroethylthio group.

The “lower alkenyloxy group” in the definition of R ^a and R ^b is a group in which the above “lower alkenyl group” is bonded to an oxygen atom, and preferably an alkenyl group having 2 to 4 carbon atoms is bonded to an oxygen atom. And more preferably a group in which an alkenyl group having 3 to 4 carbon atoms is bonded to an oxygen atom, specifically, 2-propenyloxy, 2-butenyloxy or 3-butenyloxy group. .

The “lower alkynyloxy group” in the definition of R ^a and R ^b is a group in which the above “lower alkynyl group” is bonded to an oxygen atom, and preferably an alkynyl group having 2 to 4 carbon atoms is bonded to an oxygen atom. More preferred is a group in which an alkynyl group having 3 to 4 carbon atoms is bonded to an oxygen atom, specifically 2-propynyloxy, 2-butynyloxy or 3-butynyloxy group.

The “aralkyloxy group” in the definition of R ^a and R ^b is a group in which the above “aralkyl group” is bonded to an oxygen atom. For example, benzyloxy, α-naphthylmethoxy, β-naphthylmethoxy, 2-phenethyloxy, 3-phenylpropoxy or 4-phenylbutoxy group.

  In the definition of [Substituent Group γ], the “lower alkylenedioxy group” has an alkylene moiety of methylene, ethylene, trimethylene, propylene, tetramethylene, 1-methyltrimethylene, 2-methyltrimethylene, 1,1-dimethyl. A linear or branched alkylene group having 1 to 6 carbon atoms such as ethylene, pentamethylene, 1,1-dimethyltrimethylene, 2,2-dimethyltrimethylene, 1,2-dimethyltrimethylene or hexamethylene group; Yes, preferably a linear or branched alkylenedioxy group having 1 to 4 carbon atoms, more preferably methylenedioxy, ethylenedioxy, trimethylenedioxy, propylenedioxy or tetramethylenedioxy. It is an oxy group.

  The “lower alkoxyimino group” in the definition of [Substituent group γ] is a group in which a hydrogen atom of a hydroxyimino group is replaced with the above “lower alkyl group”, preferably an alkoxyimino having 1 to 4 carbon atoms. More preferably a methoxyimino, ethoxyimino or propoxyimino group.

The “mono or di-lower alkylamino group” in the definition of R ^a and R ^b is a group in which one or two hydrogen atoms of an amino group are substituted with a lower alkyl group. Preferred is a group in which the alkyl moiety is alkyl having 1 to 4 carbon atoms, more preferred is a group in which the alkyl moiety is alkyl having 1 to 2 carbon atoms, and even more preferred is methyl. An amino, dimethylamino, ethylamino or diethylamino group.

The “lower alkylsulfonyl group” in the definition of R ^d , R ^e and [substituent group γ] is a group in which sulfonyl (—SO ₂ —) is bonded to the above “lower alkyl”, and preferably has 1 carbon atom. To 4 linear or branched alkylsulfonyl groups, more preferably a methanesulfonyl, ethanesulfonyl, propansulfonyl, isopropanesulfonyl or butanesulfonyl group, particularly preferably a methanesulfonyl, ethanesulfonyl. Or it is a propanesulfonyl group.

  The “lower alkylsulfinyl group” in the definition of [Substituent group γ] is a group in which sulfinyl (—SO—) is bonded to the above “lower alkyl”, and preferably a straight chain having 1 to 4 carbon atoms or It is a branched alkylsulfinyl group, more preferably a methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl or butylsulfinyl group, and particularly preferably a methylsulfinyl, ethylsulfinyl or propylsulfinyl group.

“Group having the formula CONR ^a R ^b ” in the definition of R ⁵ is, for example,
Carbamoyl, N-hydroxycarbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N- (s-butyl) carbamoyl, N- (t-butyl) carbamoyl, N-isobutylcarbamoyl, N-pentylcarbamoyl, N-hexylcarbamoyl, N, N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N, N-diethylcarbamoyl,
N- (hydroxymethyl) carbamoyl, N- (2-hydroxyethyl) carbamoyl, N- (3-hydroxypropyl) carbamoyl, N- (1,3-dihydroxyisopropyl) carbamoyl,
N- (2-nitroethyl) carbamoyl,
N- (cyanomethyl) carbamoyl, N- (2-cyanoethyl) carbamoyl,
N- (2-fluoroethyl) carbamoyl, N- (2,2,2-trifluoroethyl) carbamoyl, N- (3-fluoropropyl) carbamoyl, N- (4-fluorobutyl) carbamoyl, N- (5- Fluoropentyl) carbamoyl, N- (6-fluorohexyl) carbamoyl,
N- (2-chloroethyl) carbamoyl, N- (3-chloropropyl) carbamoyl, N- (4-chlorobutyl) carbamoyl,
N- (2-bromoethyl) carbamoyl, N- (3-bromopropyl) carbamoyl, N- (4-bromobutyl) carbamoyl,
N- (methoxymethyl) carbamoyl, N- (2-methoxyethyl) carbamoyl, N- (3-methoxypropyl) carbamoyl, N- (4-methoxybutyl) carbamoyl,
N- (ethoxymethyl) carbamoyl, N- (2-ethoxyethyl) carbamoyl, N- (3-ethoxypropyl) carbamoyl, N- (4-ethoxybutyl) carbamoyl,
N- (carboxymethyl) carbamoyl, N- (2-carboxyethyl) carbamoyl, N- (3-carboxypropyl) carbamoyl,
N- (methoxycarbonylmethyl) carbamoyl, N- (2-methoxycarbonylethyl) carbamoyl, N- (3-methoxycarbonylpropyl) carbamoyl, N- (ethoxycarbonylmethyl) carbamoyl, N- (1-ethoxycarbonylethyl) carbamoyl N- (2-ethoxycarbonylethyl) carbamoyl, N- (3-ethoxycarbonylpropyl) carbamoyl,
N- (carbamoylmethyl) carbamoyl,
N- (2-acetoxyethyl) carbamoyl,
N- (2-methylthioethyl) carbamoyl, N- (2-ethylthioethyl) carbamoyl, N- (2-propylthioethyl) carbamoyl,
N- (2-fluoromethylthioethyl) carbamoyl, N- (2-difluoromethylthioethyl) carbamoyl, N- (2-trifluoromethylthioethyl) carbamoyl, N- [2- (2-fluoroethylthio) ethyl] carbamoyl, N- [2- (2,2,2-trifluoroethylthio) ethyl] carbamoyl,
Substituted with a group selected from the substituent group α, such as an N- (2-aminoethyl) carbamoyl, N- (2-methylaminoethyl) carbamoyl or N- (2-dimethylaminoethyl) carbamoyl group. A carbamoyl group substituted with a lower alkyl group;
N-vinylcarbamoyl, N- (2-propenyl) carbamoyl, N- (2-methyl-2-propenyl) carbamoyl, N- (2-butenyl) carbamoyl, N- (2-methyl-2-butenyl) carbamoyl, N -(3-butenyl) carbamoyl,
N- (2-hydroxy-3-butenyl) carbamoyl, N- (4-hydroxy-2-butenyl) carbamoyl,
N- (2-cyano-2-propenyl) carbamoyl, N- (3-cyano-2-propenyl) carbamoyl,
N- (2-fluoro-2-propenyl) carbamoyl, N- (3-fluoro-2-propenyl) carbamoyl, N- (2-chloro-2-propenyl) carbamoyl, N- (3-chloro-2-propenyl) Carbamoyl, N- (3,3-difluoro-2-propenyl) carbamoyl, N- (3,3-dichloro-2-propenyl) carbamoyl, N- (3,3-dibromo-2-propenyl) carbamoyl,
N- (2-methoxy-3-butenyl) carbamoyl,
N- (3-carboxy-2-propenyl) carbamoyl, N- (4-carboxy-3-butenyl) carbamoyl,
N- (3-methoxycarbonyl-2-propenyl) carbamoyl, N- (4-methoxycarbonyl-3-butenyl) carbamoyl,
N- (3-carbamoyl-2-propenyl) carbamoyl, N- (4-carbamoyl-3-butenyl) carbamoyl,
N- (2-methylthio-3-butenyl) carbamoyl, N- (4-methylthio-2-butenyl) carbamoyl,
It may be substituted with a group selected from the substituent group α, such as an N- (2-trifluoromethylthio-3-butenyl) carbamoyl or N- (4-trifluoromethylthio-2-butenyl) carbamoyl group. A carbamoyl group substituted with a lower alkenyl group;
N-ethynylcarbamoyl, N- (2-propynyl) carbamoyl, N- (1-methyl-2-propynyl) carbamoyl, N- (2-butynyl) carbamoyl, N- (1-methyl-2-butynyl) carbamoyl, N -(3-butynyl) carbamoyl,
N- (2-hydroxy-3-butynyl) carbamoyl, N- (4-hydroxy-2-butynyl) carbamoyl,
N- (1-cyano-2-propynyl) carbamoyl, N- (3-cyano-2-propynyl) carbamoyl,
N- (2-methoxy-3-butynyl) carbamoyl,
N- (3-carboxy-2-propynyl) carbamoyl, N- (4-carboxy-3-butynyl) carbamoyl,
N- (3-methoxycarbonyl-2-propynyl) carbamoyl, N- (4-methoxycarbonyl-3-butynyl) carbamoyl,
N- (3-carbamoyl-2-butynyl) carbamoyl, N- (4-carbamoyl-3-butynyl) carbamoyl,
N- (2-methylthio-3-butynyl) carbamoyl, N- (4-methylthio-2-butynyl) carbamoyl,
It may be substituted with a group selected from the substituent group α, such as an N- (2-trifluoromethylthio-3-butynyl) carbamoyl or N- (4-trifluoromethylthio-2-butynyl) carbamoyl group. A carbamoyl group substituted with a lower alkynyl group;
N-methoxycarbamoyl, N-methoxy-N-methylcarbamoyl, N-ethoxycarbamoyl, N-propoxycarbamoyl, N-isopropoxycarbamoyl, N-butoxycarbamoyl, N- (s-butoxy) carbamoyl, N- (t-butoxy ) A carbamoyl group substituted with a lower alkoxy group, such as a carbamoyl or N-isobutoxycarbamoyl group;
A carbamoyl group substituted with a lower alkenyloxy group, such as an N- (2-propenyloxy) carbamoyl, N- (2-butenyloxy) carbamoyl or N- (3-butenyloxy) carbamoyl group;
A carbamoyl group substituted with a lower alkynyloxy group, such as an N- (2-propynyloxy) carbamoyl, N- (2-butynyloxy) carbamoyl or N- (3-butynyloxy) carbamoyl group;
A carbamoyl group substituted with an aralkyloxy group, such as an N-benzyloxycarbamoyl, N-benzyloxy-N-methylcarbamoyl or N-phenethyloxycarbamoyl group;
Carbamoyl substituted with a cycloalkyl group, such as N-cyclopropylcarbamoyl, N-cyclopropyl-N-methylcarbamoyl, N-cyclobutylcarbamoyl, N-cyclopentylcarbamoyl, N-cyclohexylcarbamoyl or N-cycloheptylcarbamoyl group Group;
N-cyclopropylmethylcarbamoyl, N-cyclopropylmethyl-N-methylcarbamoyl, N-cyclobutylmethylcarbamoyl, N-cyclopentylmethylcarbamoyl, N-cyclohexylmethylcarbamoyl, N-cycloheptylmethylcarbamoyl, N- (2-cyclo Propylethyl) carbamoyl, N- (2-cyclobutylethyl) carbamoyl, N- (2-cyclopentylethyl) carbamoyl, N- (2-cyclohexylethyl) carbamoyl, N- (2-cycloheptylethyl) carbamoyl, N- ( A lower alkyl group substituted with a cycloalkyl group, such as a 3-cyclopropylpropyl) carbamoyl, N- (3-cyclopentylpropyl) carbamoyl or N- (3-cyclohexylpropyl) carbamoyl group; Conversion carbamoyl group;
A carbamoyl group substituted with an aryl group, such as an N-phenylcarbamoyl, N-methyl-N-phenylcarbamoyl, N- (α-naphthyl) carbamoyl or N- (β-naphthyl) carbamoyl group;
N-benzylcarbamoyl, N- (α-naphthylmethyl) carbamoyl, N- (β-naphthylmethyl) carbamoyl,
N- (1-phenethyl) carbamoyl, N- (2-phenethyl) carbamoyl, N- [2- (α-naphthyl) ethyl] carbamoyl, N- [2- (β-naphthyl) ethyl] carbamoyl, N- (3 A carbamoyl group substituted with an aralkyl group, such as a -phenylpropyl) carbamoyl, N- (4-phenylbutyl) carbamoyl, N- (5-phenylpentyl) carbamoyl or N- (6-phenylhexyl) carbamoyl group;
Such as N- (2 or 3-furyl) carbamoyl, N- (2 or 3-thienyl) carbamoyl, N- (2 or 3-pyrrolyl) carbamoyl or N- (2,3 or 4-pyridyl) carbamoyl groups, A carbamoyl group substituted with a heteroaryl group;
N- (2 or 3-furylmethyl) carbamoyl, N- (2 or 3-furylmethyl) -N-methylcarbamoyl, N- [2- (2 or 3-furyl) ethyl] carbamoyl, N- [3- ( 2 or 3-furyl) propyl] carbamoyl, N- [4- (2 or 3-furyl) butyl] carbamoyl,
N- (2 or 3-thienylmethyl) carbamoyl, N- [2- (2 or 3-thienyl) ethyl] carbamoyl, N- [3- (2 or 3-thienyl) propyl] carbamoyl, N- [4- ( 2 or 3-thienyl) butyl] carbamoyl,
N- (2 or 3-pyrrolylmethyl) carbamoyl, N- [2- (2 or 3-pyrrolyl) ethyl] carbamoyl, N- [3- (2 or 3-pyrrolyl) propyl] carbamoyl, N- [4- (2 Or 3-pyrrolyl) butyl] carbamoyl,
N- (2,3 or 4-pyridylmethyl) carbamoyl, N- [2- (2,3 or 4-pyridyl) ethyl] carbamoyl, N- [3- (2,3 or 4-pyridyl) propyl] carbamoyl, N- [4- (2,3 or 4-pyridyl) butyl] carbamoyl,
N- (2,4 or 5-pyrimidinylmethyl) carbamoyl, N- [2- (2,4 or 5-pyrimidinyl) ethyl] carbamoyl, N- [3- (2,4 or 5-pyrimidinyl) propyl] carbamoyl or A carbamoyl group substituted with a lower alkyl group substituted with a heteroaryl group, such as an N- [4- (2,4 or 5-pyrimidinyl) butyl] carbamoyl group; or hydrazinocarbonyl, 2-methylhydrazinocarbonyl 2-ethylhydrazinocarbonyl, 2-propylhydrazinocarbonyl, 2-isopropylhydrazinocarbonyl, 2-butylhydrazinocarbonyl, 2,2-dimethylhydrazinocarbonyl, 2-ethyl-2-methylhydrazinocarbonyl or 2 , 2-diethylhydrazinocarbonyl group, Be a amino group or hydrazinocarbonyl group is carbamoyl substituted by mono- or di-lower alkylamino group,
Preferably, carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N, N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl,
N- (2-hydroxyethyl) carbamoyl, N- (3-hydroxypropyl) carbamoyl, N- (1,3-dihydroxyisopropyl) carbamoyl,
N-cyanomethylcarbamoyl, N- (2-cyanoethyl) carbamoyl,
Substituted, such as N- (2-fluoroethyl) carbamoyl, N- (2,2,2-trifluoroethyl) carbamoyl, N- (3-fluoropropyl) carbamoyl or N- (2-methoxyethyl) carbamoyl groups A carbamoyl group substituted with a lower alkyl group optionally substituted with a group selected from group group α;
A carbamoyl group substituted with a lower alkenyl group optionally substituted with a group selected from substituent group α, such as an N- (2-propenyl) carbamoyl group;
A carbamoyl group substituted with a lower alkynyl group optionally substituted with a group selected from substituent group α, such as an N- (2-propynyl) carbamoyl group;
A carbamoyl group substituted with a lower alkoxy group, such as an N-methoxycarbamoyl, N-ethoxycarbamoyl or N-propoxycarbamoyl group;
A carbamoyl group substituted with a lower alkenyloxy group, such as an N- (2-propenyloxy) carbamoyl group;
A carbamoyl group substituted with a lower alkynyloxy group, such as an N- (2-propynyloxy) carbamoyl group;
A carbamoyl group substituted with a cycloalkyl group, such as an N-cyclopropylcarbamoyl, N-cyclobutylcarbamoyl or N-cyclopentylcarbamoyl group;
A carbamoyl group substituted with a lower alkyl group substituted with a cycloalkyl group, such as an N-cyclopropylmethylcarbamoyl group;
A carbamoyl group substituted with an aralkyl group, such as an N-benzylcarbamoyl or N- (α-naphthyl) carbamoyl group; or a hydrazinocarbonyl, 2-methylhydrazinocarbonyl, 2,2-dimethylhydrazinocarbonyl group A hydrazinocarbonyl group which is a carbamoyl group substituted with an amino group or a mono- or di-lower alkylamino group.

“Group having formula COR ^c ” in the definition of R ⁵ is, for example,
An alkanoyl group such as formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, pivaloyl, isovaleryl, hexanoyl or heptanoyl group;
Fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, 3-fluoropropionyl, 3,3-difluoropropionyl, 3,3,3-trifluoropropionyl, 3-chloropropionyl, 3 Halogeno lower alkylcarbonyl groups such as 1,3-dichloropropionyl, 3,3,3-trichloropropionyl or 3-bromopropionyl group;
Lower alkoxy lower groups such as methoxymethylcarbonyl, ethoxymethylcarbonyl, 2-methoxyethylcarbonyl, 2-ethoxyethylcarbonyl, 2-propoxyethylcarbonyl, 2-butoxyethylcarbonyl, 3-methoxypropylcarbonyl or 4-methoxybutylcarbonyl group An alkylcarbonyl group; or a hydroxy lower alkylcarbonyl group such as hydroxyacetyl, 2-hydroxyethylcarbonyl, 3-hydroxypropylcarbonyl or 4-hydroxybutylcarbonyl group;
Preferably, an alkanoyl group such as a formyl, acetyl or propionyl group;
A halogeno lower alkylcarbonyl group such as a fluoroacetyl group;
A lower alkoxy lower alkylcarbonyl group such as a methoxymethylcarbonyl group;
A hydroxy lower alkylcarbonyl group, such as a hydroxyacetyl group.

The “group having the formula SO ₂ NR ^a R ^b ” in the definition of R ⁵ is, for example,
Sulfamoyl, N-hydroxysulfamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N- (s-butyl ) Sulfamoyl, N- (t-butyl) sulfamoyl, N-isobutylsulfamoyl, N-pentylsulfamoyl, N-hexylsulfamoyl, N, N-dimethylsulfamoyl, N-ethyl-N-methylsulf Famoyl, N, N-diethylsulfamoyl,
N- (hydroxymethyl) sulfamoyl, N- (2-hydroxyethyl) sulfamoyl, N- (3-hydroxypropyl) sulfamoyl, N- (1,3-dihydroxyisopropyl) sulfamoyl,
N- (2-nitroethyl) sulfamoyl,
N- (cyanomethyl) sulfamoyl, N- (2-cyanoethyl) sulfamoyl,
N- (2-fluoroethyl) sulfamoyl, N- (2,2,2-trifluoroethyl) sulfamoyl, N- (3-fluoropropyl) sulfamoyl, N- (4-fluorobutyl) sulfamoyl, N- (5- Fluoropentyl) sulfamoyl, N- (6-fluorohexyl) sulfamoyl,
N- (2-chloroethyl) sulfamoyl, N- (3-chloropropyl) sulfamoyl, N- (4-chlorobutyl) sulfamoyl,
N- (2-bromoethyl) sulfamoyl, N- (3-bromopropyl) sulfamoyl, N- (4-bromobutyl) sulfamoyl,
N- (methoxymethyl) sulfamoyl, N- (2-methoxyethyl) sulfamoyl, N- (3-methoxypropyl) sulfamoyl, N- (4-methoxybutyl) sulfamoyl,
N- (ethoxymethyl) sulfamoyl, N- (2-ethoxyethyl) sulfamoyl, N- (3-ethoxypropyl) sulfamoyl, N- (4-ethoxybutyl) sulfamoyl,
N- (carboxymethyl) sulfamoyl, N- (2-carboxyethyl) sulfamoyl, N- (3-carboxypropyl) sulfamoyl,
N- (methoxycarbonylmethyl) sulfamoyl, N- (2-methoxycarbonylethyl) sulfamoyl, N- (3-methoxycarbonylpropyl) sulfamoyl, N- (ethoxycarbonylmethyl) sulfamoyl, N- (1-ethoxycarbonylethyl) sulfamoyl N- (2-ethoxycarbonylethyl) sulfamoyl, N- (3-ethoxycarbonylpropyl) sulfamoyl,
N- (carbamoylmethyl) sulfamoyl,
N- (2-acetoxyethyl) sulfamoyl,
N- (2-methylthioethyl) sulfamoyl, N- (2-ethylthioethyl) sulfamoyl, N- (2-propylthioethyl) sulfamoyl,
N- (2-fluoromethylthioethyl) sulfamoyl, N- (2-difluoromethylthioethyl) sulfamoyl, N- (2-trifluoromethylthioethyl) sulfamoyl, N- [2- (2-fluoroethylthio) ethyl] sulfamoyl, N- [2- (2,2,2-trifluoroethylthio) ethyl] sulfamoyl,
Substituted with a group selected from the substituent group α, such as N- (2-aminoethyl) sulfamoyl, N- (2-methylaminoethyl) sulfamoyl or N- (2-dimethylaminoethyl) sulfamoyl. A sulfamoyl group substituted with a lower alkyl group;
N-vinylsulfamoyl, N- (2-propenyl) sulfamoyl, N- (2-methyl-2-propenyl) sulfamoyl, N- (2-butenyl) sulfamoyl, N- (2-methyl-2-butenyl) sulfamoyl N- (3-butenyl) sulfamoyl,
N- (2-hydroxy-3-butenyl) sulfamoyl, N- (4-hydroxy-2-butenyl) sulfamoyl,
N- (2-cyano-2-propenyl) sulfamoyl, N- (3-cyano-2-propenyl) sulfamoyl,
N- (2-fluoro-2-propenyl) sulfamoyl, N- (3-fluoro-2-propenyl) sulfamoyl, N- (2-chloro-2-propenyl) sulfamoyl, N- (3-chloro-2-propenyl) Sulfamoyl, N- (3,3-difluoro-2-propenyl) sulfamoyl, N- (3,3-dichloro-2-propenyl) sulfamoyl, N- (3,3-dibromo-2-propenyl) sulfamoyl,
N- (2-methoxy-3-butenyl) sulfamoyl,
N- (3-carboxy-2-propenyl) sulfamoyl, N- (4-carboxy-3-butenyl) sulfamoyl,
N- (3-methoxycarbonyl-2-propenyl) sulfamoyl, N- (4-methoxycarbonyl-3-butenyl) sulfamoyl,
N- (3-carbamoyl-2-propenyl) sulfamoyl, N- (4-carbamoyl-3-butenyl) sulfamoyl,
N- (2-methylthio-3-butenyl) sulfamoyl, N- (4-methylthio-2-butenyl) sulfamoyl,
It may be substituted with a group selected from the substituent group α, such as N- (2-trifluoromethylthio-3-butenyl) sulfamoyl or N- (4-trifluoromethylthio-2-butenyl) sulfamoyl group. A sulfamoyl group substituted with a lower alkenyl group;
N-ethynylsulfamoyl, N- (2-propynyl) sulfamoyl, N- (1-methyl-2-propynyl) sulfamoyl, N- (2-butynyl) sulfamoyl, N- (1-methyl-2-butynyl) sulfamoyl N- (3-butynyl) sulfamoyl,
N- (2-hydroxy-3-butynyl) sulfamoyl, N- (4-hydroxy-2-butynyl) sulfamoyl,
N- (1-cyano-2-propynyl) sulfamoyl, N- (3-cyano-2-propynyl) sulfamoyl,
N- (2-methoxy-3-butynyl) sulfamoyl,
N- (3-carboxy-2-propynyl) sulfamoyl, N- (4-carboxy-3-butynyl) sulfamoyl,
N- (3-methoxycarbonyl-2-propynyl) sulfamoyl, N- (4-methoxycarbonyl-3-butynyl) sulfamoyl,
N- (3-carbamoyl-2-butynyl) sulfamoyl, N- (4-carbamoyl-3-butynyl) sulfamoyl,
N- (2-methylthio-3-butynyl) sulfamoyl, N- (4-methylthio-2-butynyl) sulfamoyl,
It may be substituted with a group selected from the substituent group α, such as N- (2-trifluoromethylthio-3-butynyl) sulfamoyl or N- (4-trifluoromethylthio-2-butynyl) sulfamoyl group. A sulfamoyl group substituted with a lower alkynyl group;
N-methoxysulfamoyl, N-methoxy-N-methylsulfamoyl, N-ethoxysulfamoyl, N-propoxysulfamoyl, N-isopropoxysulfamoyl, N-butoxysulfamoyl, N- ( a sulfamoyl group substituted with a lower alkoxy group, such as a (s-butoxy) sulfamoyl, N- (t-butoxy) sulfamoyl or N-isobutoxysulfamoyl group;
A sulfamoyl group substituted with a lower alkenyloxy group, such as an N- (2-propenyloxy) sulfamoyl, N- (2-butenyloxy) sulfamoyl or N- (3-butenyloxy) sulfamoyl group;
A sulfamoyl group substituted with a lower alkynyloxy group, such as an N- (2-propynyloxy) sulfamoyl, N- (2-butynyloxy) sulfamoyl or N- (3-butynyloxy) sulfamoyl group;
A sulfamoyl group substituted with an aralkyloxy group, such as an N-benzyloxysulfamoyl, N-benzyloxy-N-methylsulfamoyl or N-phenethyloxysulfamoyl group;
N-cyclopropylsulfamoyl, N-cyclopropyl-N-methylsulfamoyl, N-cyclobutylsulfamoyl, N-cyclopentylsulfamoyl, N-cyclohexylsulfamoyl or N-cycloheptylsulfamoyl groups A sulfamoyl group substituted with a cycloalkyl group, such as
N-cyclopropylmethylsulfamoyl, N-cyclopropylmethyl-N-methylsulfamoyl, N-cyclobutylmethylsulfamoyl, N-cyclopentylmethylsulfamoyl, N-cyclohexylmethylsulfamoyl, N-cyclo Heptylmethylsulfamoyl, N- (2-cyclopropylethyl) sulfamoyl, N- (2-cyclobutylethyl) sulfamoyl, N- (2-cyclopentylethyl) sulfamoyl, N- (2-cyclohexylethyl) sulfamoyl, N- Cycloalkyl groups such as (2-cycloheptylethyl) sulfamoyl, N- (3-cyclopropylpropyl) sulfamoyl, N- (3-cyclopentylpropyl) sulfamoyl or N- (3-cyclohexylpropyl) sulfamoyl groups Substituted with substituted lower alkyl group a sulfamoyl group;
A sulfamoyl group substituted with an aryl group, such as an N-phenylsulfamoyl, N-methyl-N-phenylsulfamoyl, N- (α-naphthyl) sulfamoyl or N- (β-naphthyl) sulfamoyl group;
N-benzylsulfamoyl, N- (α-naphthylmethyl) sulfamoyl, N- (β-naphthylmethyl) sulfamoyl,
N- (1-phenethyl) sulfamoyl, N- (2-phenethyl) sulfamoyl, N- [2- (α-naphthyl) ethyl] sulfamoyl, N- [2- (β-naphthyl) ethyl] sulfamoyl, N- (3 A sulfamoyl group substituted with an aralkyl group, such as a -phenylpropyl) sulfamoyl, N- (4-phenylbutyl) sulfamoyl, N- (5-phenylpentyl) sulfamoyl or N- (6-phenylhexyl) sulfamoyl group;
Such as N- (2 or 3-furyl) sulfamoyl, N- (2 or 3-thienyl) sulfamoyl, N- (2 or 3-pyrrolyl) sulfamoyl or N- (2,3 or 4-pyridyl) sulfamoyl groups, A sulfamoyl group substituted with a heteroaryl group;
N- (2 or 3-furylmethyl) sulfamoyl, N- (2 or 3-furylmethyl) -N-methylsulfamoyl, N- [2- (2 or 3-furyl) ethyl] sulfamoyl, N- [3 -(2 or 3-furyl) propyl] sulfamoyl, N- [4- (2 or 3-furyl) butyl] sulfamoyl,
N- (2 or 3-thienylmethyl) sulfamoyl, N- [2- (2 or 3-thienyl) ethyl] sulfamoyl, N- [3- (2 or 3-thienyl) propyl] sulfamoyl, N- [4- ( 2 or 3-thienyl) butyl] sulfamoyl,
N- (2 or 3-pyrrolylmethyl) sulfamoyl, N- [2- (2 or 3-pyrrolyl) ethyl] sulfamoyl, N- [3- (2 or 3-pyrrolyl) propyl] sulfamoyl, N- [4- (2 Or 3-pyrrolyl) butyl] sulfamoyl,
N- (2,3 or 4-pyridylmethyl) sulfamoyl, N- [2- (2,3 or 4-pyridyl) ethyl] sulfamoyl, N- [3- (2,3 or 4-pyridyl) propyl] sulfamoyl, N- [4- (2,3 or 4-pyridyl) butyl] sulfamoyl,
N- (2,4 or 5-pyrimidinylmethyl) sulfamoyl, N- [2- (2,4 or 5-pyrimidinyl) ethyl] sulfamoyl, N- [3- (2,4 or 5-pyrimidinyl) propyl] sulfamoyl or A sulfamoyl group substituted with a lower alkyl group substituted with a heteroaryl group, such as an N- [4- (2,4 or 5-pyrimidinyl) butyl] sulfamoyl group; or hydrazinosulfonyl, 2-methylhydrazinosulfonyl 2-ethylhydrazinosulfonyl, 2-propylhydrazinosulfonyl, 2-isopropylhydrazinosulfonyl, 2-butylhydrazinosulfonyl, 2,2-dimethylhydrazinosulfonyl, 2-ethyl-2-methylhydrazinosulfonyl or 2 , 2-Diethylhydrazinosulfonyl group Such can be a hydrazino sulfonyl group or a sulfamoyl group substituted with an amino group or a mono- or di-lower alkylamino group,
Preferably, sulfamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N, N-dimethylsulfamoyl, N-ethyl-N-methyl Sulfamoyl,
N- (2-hydroxyethyl) sulfamoyl, N- (3-hydroxypropyl) sulfamoyl, N- (1,3-dihydroxyisopropyl) sulfamoyl,
N-cyanomethylsulfamoyl, N- (2-cyanoethyl) sulfamoyl,
Substituted, such as N- (2-fluoroethyl) sulfamoyl, N- (2,2,2-trifluoroethyl) sulfamoyl, N- (3-fluoropropyl) sulfamoyl or N- (2-methoxyethyl) sulfamoyl groups A sulfamoyl group substituted with a lower alkyl group optionally substituted with a group selected from group group α;
A sulfamoyl group substituted with a lower alkenyl group optionally substituted with a group selected from substituent group α, such as an N- (2-propenyl) sulfamoyl group;
A sulfamoyl group substituted with a lower alkynyl group optionally substituted with a group selected from substituent group α, such as an N- (2-propynyl) sulfamoyl group;
A sulfamoyl group substituted with a lower alkoxy group, such as an N-methoxysulfamoyl, N-ethoxysulfamoyl or N-propoxysulfamoyl group;
A sulfamoyl group substituted with a lower alkenyloxy group, such as an N- (2-propenyloxy) sulfamoyl group;
A sulfamoyl group substituted with a lower alkynyloxy group, such as an N- (2-propynyloxy) sulfamoyl group;
A sulfamoyl group substituted with a cycloalkyl group, such as an N-cyclopropylsulfamoyl, N-cyclobutylsulfamoyl or N-cyclopentylsulfamoyl group;
A sulfamoyl group substituted with a lower alkyl group substituted with a cycloalkyl group, such as an N-cyclopropylmethylsulfamoyl group;
A sulfamoyl group substituted with an aralkyl group, such as an N-benzylsulfamoyl or N- (α-naphthyl) sulfamoyl group; or a hydrazinosulfonyl, 2-methylhydrazinosulfonyl, 2,2-dimethylhydrazinosulfonyl group Or a hydrazinosulfonyl group which is a sulfamoyl group substituted with an amino group or a mono- or di-lower alkylamino group.

The “group having the formula SO ₂ R ^c ” in the definition of R ⁵ is, for example,
Lower alkylsulfonyl groups such as methanesulfonyl, ethanesulfonyl, propanesulfonyl, isopropanesulfonyl, butanesulfonyl, s-butanesulfonyl, t-butanesulfonyl, isobutanesulfonyl, pentanesulfonyl or hexanesulfonyl groups;
Fluoromethanesulfonyl, difluoromethanesulfonyl, trifluoromethanesulfonyl, chloromethanesulfonyl, dichloromethanesulfonyl, trichloromethanesulfonyl, bromomethanesulfonyl, 2-fluoroethanesulfonyl, 3-fluoropropanesulfonyl, 3,3-difluoropropanesulfonyl, 3,3 A halogeno lower alkylsulfonyl group such as 1,3-trifluoropropanesulfonyl, 3-chloropropanesulfonyl, 3,3-dichloropropanesulfonyl, 3,3,3-trichloropropanesulfonyl or 3-bromopropanesulfonyl group;
Lower alkoxy lower groups such as methoxymethanesulfonyl, ethoxymethanesulfonyl, 2-methoxyethanesulfonyl, 2-ethoxyethanesulfonyl, 2-propoxyethanesulfonyl, 2-butoxyethanesulfonyl, 3-methoxypropanesulfonyl or 4-methoxybutanesulfonyl group An alkylsulfonyl group; or a hydroxy lower alkylsulfonyl group such as hydroxymethanesulfonyl, 2-hydroxyethanesulfonyl, 3-hydroxypropanesulfonyl or 4-hydroxybutanesulfonyl group;
Preferably, a lower alkylsulfonyl group such as a methanesulfonyl or ethanesulfonyl group;
A halogeno lower alkylsulfonyl group such as a fluoromethanesulfonyl or 2-fluoroethanesulfonyl group;
A lower alkoxy lower alkylsulfonyl group such as methoxymethanesulfonyl or 2-methoxyethanesulfonyl group; or a hydroxy lower alkylsulfonyl group such as hydroxymethanesulfonyl or 2-hydroxyethanesulfonyl group.

“Group having formula SOR ^c ” in the definition of R ⁵ is, for example,
Lower alkyl sulfinyl groups such as methanesulfinyl, ethanesulfinyl, propanesulfinyl, isopropanesulfinyl, butanesulfinyl, s-butanesulfinyl, t-butanesulfinyl, isobutanesulfinyl, pentansulphinyl or hexanesulfinyl groups;
Fluoromethanesulfinyl, difluoromethanesulfinyl, trifluoromethanesulfinyl, chloromethanesulfinyl, dichloromethanesulfinyl, trichloromethanesulfinyl, bromomethanesulfinyl, 2-fluoroethanesulfinyl, 3-fluoropropanesulfinyl, 3,3-difluoropropanesulfinyl, 3,3 Halogeno lower alkylsulfinyl groups such as 1,3-trifluoropropanesulfinyl, 3-chloropropanesulfinyl, 3,3-dichloropropanesulfinyl, 3,3,3-trichloropropanesulfinyl or 3-bromopropanesulfinyl groups;
Lower alkoxy such as methoxymethanesulfinyl, ethoxymethanesulfinyl, 2-methoxyethanesulfinyl, 2-ethoxyethanesulfinyl, 2-propoxyethanesulfinyl, 2-butoxyethanesulfinyl, 3-methoxypropanesulfinyl or 4-methoxybutanesulfinyl group A lower alkyl sulfinyl group; or a hydroxy lower alkyl sulfinyl group, such as hydroxymethane sulfinyl, 2-hydroxyethane sulfinyl, 3-hydroxypropane sulfinyl or 4-hydroxybutane sulfinyl group;
Preferably, a lower alkylsulfinyl group such as a methanesulfinyl or ethanesulfinyl group;
Halogeno lower alkylsulfinyl groups such as fluoromethanesulfinyl or 2-fluoroethanesulfinyl groups;
A lower alkoxy lower alkyl sulfinyl group such as methoxymethanesulfinyl or 2-methoxyethanesulfinyl group; or a hydroxy lower alkylsulfinyl group such as hydroxymethanesulfinyl or 2-hydroxyethanesulfinyl group.

The “lower alkylcarbonyl group” in the definition of R ^d and R ^e is a group in which a carbonyl group is bonded to the above “lower alkyl group”, and preferably a linear or branched alkylcarbonyl having 1 to 4 carbon atoms. Group, more preferably an alkylcarbonyl group having 1 to 3 carbon atoms, and particularly preferably an acetyl group.

  The “lower acyloxy group” in the definition of [Substituent group α] is a group in which an oxygen atom is bonded to the above-mentioned “lower alkylcarbonyl group”, preferably a linear or branched acyloxy group having 1 to 5 carbon atoms. More preferably an acetyloxy group, a propionyloxy group, a butyryloxy group or a pivaloyloxy group.

The “lower alkoxycarbonyl group” in the definition of R ⁵ and substituent group α is a group in which a carbonyl group is bonded to the above “lower alkoxy group”, and preferably an alkoxy group having 1 to 4 carbon atoms is a carbonyl group. It is a bonded group. Suitable examples thereof may be, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl or isobutoxycarbonyl group, preferably methoxycarbonyl, ethoxycarbonyl or propoxy It is a carbonyl group.

The “aryloxycarbonyl group” in the definition of R ⁵ is a group in which a carbonyl group is bonded to an aryloxy group in which an oxygen atom is bonded to the above “aryl group”. Preferred examples thereof include, for example, phenoxycarbonyl, naphthyloxy It can be a carbonyl, phenanthryloxycarbonyl or anthracenyloxycarbonyl group, preferably a phenoxycarbonyl or naphthyloxycarbonyl group, and more preferably a phenoxycarbonyl group.

The “aralkyloxycarbonyl group” in the definition of R ⁵ is a group in which a carbonyl group is bonded to the above aralkyloxy group, and preferred examples thereof include benzyloxycarbonyl or phenethyloxycarbonyl group.

Of the groups defined as R ⁵
Preferably, a group having the formula CONR ^a R ^b , a group having the formula COR ^c , a group having the formula SO ₂ NR ^a R ^b , a group having the formula SO ₂ R ^c or a group having the formula SOR ^c (wherein R ^a and R ^b are the same or different and each represents a hydrogen atom,
A lower alkyl group which may be substituted with a group selected from substituent group α,
A lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group,
Represents an amino group or a mono- or di-lower alkylamino group,
R ^c represents a lower alkyl group. Yes,
More preferably, a group having the formula CONR ^a R ^b , a group having the formula SO ₂ NR ^a R ^b , a group having the formula SO ₂ R ^c or a group having the formula SOR ^c (wherein R ^a and R ^b are The same or different and represents a hydrogen atom, a lower alkyl group, a halogeno lower alkyl group, a hydroxy lower alkyl group, a lower alkoxy lower alkyl group, a lower alkoxy group or a cycloalkyl group,
R ^c represents a lower alkyl group. ) And
More preferably, carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-cyclopropylcarbamoyl, N-cyclopentylcarbamoyl, N- (2-fluoroethyl) carbamoyl, N -(2-methoxyethyl) carbamoyl,
N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-cyclopropylsulfamoyl, N-cyclopentylsulfamoyl, N- (2-fluoroethyl) ) Sulfamoyl, N- (2-methoxyethyl) sulfamoyl, N-methoxysulfamoyl,
Methanesulfonyl, ethanesulfonyl, propanesulfonyl,
A methanesulfinyl, ethanesulfinyl or propanesulfinyl group;

Of the groups defined as R ⁶ , a preferred group is a hydrogen atom, a fluorine atom or a methoxy group, and more preferably a hydrogen atom.

Of the groups defined as R ⁷ , preferably a hydrogen atom, a hydroxy group or a lower alkyl group, more preferably a hydrogen atom, a hydroxy group or a methyl group, and even more preferably a hydrogen atom. It is.

Among groups defined as “substituent group α”, a preferred group of groups is “substituent group α ¹ ”, which includes a hydroxy group, a cyano group, a halogen atom, a lower alkoxy group, and a halogeno lower alkoxy group. Consists of. Among the groups defined in the “substituent group α ¹ ”, preferred groups are a hydroxy group, a cyano group, a halogen atom, a lower alkoxy group or a halogeno lower alkoxy group, and more preferably a halogen atom.

Among the groups defined as “substituent group β”, a preferred group of groups is “substituent group β ¹ ”, which consists of a lower alkyl group, a halogeno lower alkyl group and a hydroxy lower alkyl group. Among the groups defined in the “substituent group β ¹ ”, a preferred group is a halogeno lower alkyl group.

  “Pharmaceutically acceptable salt thereof” means that the compound having the general formula (I) of the present invention has a basic group such as an amino group by reacting with an acid, or carboxyl, carbamoyl, In the case of having an acidic group such as a sulfamoyl or hydroxyaryl group, the salt is shown because it can be converted into a salt by reacting with a base.

  Salts based on basic groups are preferably inorganic such as hydrohalides such as hydrochlorides, hydrobromides, hydroiodides, nitrates, perchlorates, sulfates, phosphates, etc. Acid salts; lower alkanesulfonates such as methanesulfonate, trifluoromethanesulfonate, ethanesulfonate, arylsulfonates such as benzenesulfonate, p-toluenesulfonate, acetates, Organic acid salts such as malate, fumarate, succinate, citrate, ascorbate, tartrate, succinate, maleate; or glycine, lysine, arginine, ornithine, Amino acid salts such as glutamate and aspartate.

  On the other hand, the salt based on an acidic group is preferably a metal such as an alkali metal salt such as sodium salt, potassium salt or lithium salt, an alkaline earth metal salt such as calcium salt or magnesium salt, an aluminum salt or an iron salt. Salt: inorganic salt such as ammonium salt, t-octylamine salt, dibenzylamine salt, morpholine salt, glucosamine salt, phenylglycine alkyl ester salt, ethylenediamine salt, N-methylglucamine salt, guanidine salt, diethylamine salt, triethylamine Salt, dicyclohexylamine salt, N, N′-dibenzylethylenediamine salt, chloroprocaine salt, procaine salt, diethanolamine salt, N-benzylphenethylamine salt, piperazine salt, tetramethylammonium salt, tris (hydroxymethyl) aminomethane salt Organic Amine salts and the like; or glycine salts, lysine salts, arginine salts, ornithine salts, glutamic acid salts, amino acid salts such as aspartate.

  The compound having the general formula (I) of the present invention or a pharmacologically acceptable salt thereof absorbs moisture by being left in the atmosphere or recrystallized, and adsorbs water, or hydrates. Such hydrates are also included in the present invention.

  The compound having the general formula (I) of the present invention may have geometric isomers (cis-trans isomers or ZE isomers) and optical isomers based on asymmetric centers in the molecule. In the compounds of the present invention, these isomers and mixtures of these isomers are all represented by a single formula, that is, the general formula (I), but the present invention is not limited to these isomers and these isomers. All the mixtures in an arbitrary ratio are included.

The compounds having the general formula (I) are preferably compounds shown in Tables 1 to 14. In addition, the compound of Table 1 thru | or Table 14 has a formula of a compound (I-1) thru | or a compound (I-14), respectively.
Table 1

―――――――――――――――――――――――――――――――――――
Compound R¹          R²            R^Five                    R⁸ _a    R⁸ _b
Number
―――――――――――――――――――――――――――――――――――
1-1 Ph 4-Pyr COOH H H
1-2 Ph 4-Pyr COOMe H H
1-3 Ph 4-Pyr COOEt H H
1-4 Ph 4-Pyr COOPr H H
1-5 Ph 4-Pyr COO-i-Pr H H
1-6 Ph 4-Pyr COOBu H H
1-7 Ph 4-Pyr COOBn H H
1-8 Ph 4-Pyr COOPh H H
1-9 Ph 4-Pyr CONH₂                  H H
1-10 Ph 4-Pyr CONHMe H H
1-11 Ph 4-Pyr CONHEt H H
1-12 Ph 4-Pyr CONHPr H H
1-13 Ph 4-Pyr CONH-i-Pr H H
1-14 Ph 4-Pyr CONHBu H H
1-15 Ph 4-Pyr CONHBn H H
1-16 Ph 4-Pyr CONMe₂                 H H
1-17 Ph 4-Pyr CONH-c-Pr H H
1-18 Ph 4-Pyr CONH-c-Bu H H
1-19 Ph 4-Pyr CONH-c-Pen H H
1-20 Ph 4-Pyr CONH-c-Hex H H
1-21 Ph 4-Pyr CONH-c-Hep H H
1-22 Ph 4-Pyr CONHCH₂-c-Pr H H
1-23 Ph 4-Pyr CONH-Allyl H H
1-24 Ph 4-Pyr CONH-Propargyl H H
1-25 Ph 4-Pyr CONHPh H H
1-26 Ph 4-Pyr CONH-3-Pyr H H
1-27 Ph 4-Pyr CONHCH₂-4-Pyr H H
1-28 Ph 4-Pyr CONH- (CH₂)₂-OH H H
1-29 Ph 4-Pyr CONHCH (CH₂OH)₂           H H
1-30 Ph 4-Pyr CONH- (CH₂)₂-OAc H H
1-31 Ph 4-Pyr CONHCH₂CN H H
1-32 Ph 4-Pyr CONH- (CH₂)₂-F H H
1-33 Ph 4-Pyr CONH- (CH₂)₂-OMe H H
1-34 Ph 4-Pyr CONH- (CH₂)₂-SMe H H
1-35 Ph 4-Pyr CONH- (CH₂)₂-NH₂          H H
1-36 Ph 4-Pyr CONH- (CH₂)₂-NHMe H H
1-37 Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂       H H
1-38 Ph 4-Pyr CONHCH₂COOH H H
1-39 Ph 4-Pyr CONHCH₂COOEt H H
1-40 Ph 4-Pyr CONHCH (Me) COOEt H H
1-41 Ph 4-Pyr CONHCH₂CONH₂            H H
1-42 Ph 4-Pyr CONHOH H H
1-43 Ph 4-Pyr CONHOMe H H
1-44 Ph 4-Pyr CONHOEt H H
1-45 Ph 4-Pyr CONHOPr H H
1-46 Ph 4-Pyr CONHO-Allyl H H
1-47 Ph 4-Pyr CONHOBn H H
1-48 Ph 4-Pyr CONHNH₂                H H
1-49 Ph 4-Pyr CONHNHMe H H
1-50 Ph 4-Pyr CONHN (Me)₂             H H
1-51 Ph 4-Pyr COMe H H
1-52 Ph 4-Pyr COEt H H
1-53 Ph 4-Pyr COPr H H
1-54 Ph 4-Pyr CO-i-Pr H H
1-55 Ph 4-Pyr COBu H H
1-56 Ph 4-Pyr COCF_Three                  H H
1-57 Ph 4-Pyr CO- (CH₂)₂-F H H
1-58 Ph 4-Pyr CO- (CH₂)₂-OH H H
1-59 Ph 4-Pyr CO- (CH₂)₂-OMe H H
1-60 Ph 4-Pyr SOMe H H
1-61 Ph 4-Pyr SOEt H H
1-62 Ph 4-Pyr SOPr H H
1-63 Ph 4-Pyr SO-i-Pr H H
1-64 Ph 4-Pyr SOBu H H
1-65 Ph 4-Pyr SOCF_Three                  H H
1-66 Ph 4-Pyr SO- (CH₂)₂-F H H
1-67 Ph 4-Pyr SO- (CH₂)₂-OH H H
1-68 Ph 4-Pyr SO- (CH₂)₂-OMe H H
1-69 Ph 4-Pyr SO₂Me H H
1-70 Ph 4-Pyr SO₂Et H H
1-71 Ph 4-Pyr SO₂Pr H H
1-72 Ph 4-Pyr SO₂-i-Pr H H
1-73 Ph 4-Pyr SO₂Bu H H
1-74 Ph 4-Pyr SO₂CF_Three                  H H
1-75 Ph 4-Pyr SO₂-(CH₂)₂-F H H
1-76 Ph 4-Pyr SO₂-(CH₂)₂-OH H H
1-77 Ph 4-Pyr SO₂-(CH₂)₂-OMe H H
1-78 Ph 4-Pyr SO₂NH₂                 H H
1-79 Ph 4-Pyr SO₂NHMe H H
1-80 Ph 4-Pyr SO₂NHEt H H
1-81 Ph 4-Pyr SO₂NHPr H H
1-82 Ph 4-Pyr SO₂NH-i-Pr H H
1-83 Ph 4-Pyr SO₂NHBu H H
1-84 Ph 4-Pyr SO₂NHBn H H
1-85 Ph 4-Pyr SO₂NMe₂                H H
1-86 Ph 4-Pyr SO₂NH-c-Pr H H
1-87 Ph 4-Pyr SO₂NH-c-Bu H H
1-88 Ph 4-Pyr SO₂NH-c-Pen H H
1-89 Ph 4-Pyr SO₂NH-c-Hex H H
1-90 Ph 4-Pyr SO₂NH-c-Hep H H
1-91 Ph 4-Pyr SO₂NHCH₂-c-Pr H H
1-92 Ph 4-Pyr SO₂NH-Allyl H H
1-93 Ph 4-Pyr SO₂NH-Propargyl H H
1-94 Ph 4-Pyr SO₂NHPh H H
1-95 Ph 4-Pyr SO₂NH-3-Pyr H H
1-96 Ph 4-Pyr SO₂NHCH₂-4-Pyr H H
1-97 Ph 4-Pyr SO₂NH- (CH₂)₂-OH H H
1-98 Ph 4-Pyr SO₂NHCH (CH₂OH)₂          H H
1-99 Ph 4-Pyr SO₂NH- (CH₂)₂-OAc H H
1-100 Ph 4-Pyr SO₂NHCH₂CN H H
1-101 Ph 4-Pyr SO₂NH- (CH₂)₂-F H H
1-102 Ph 4-Pyr SO₂NH- (CH₂)₂-OMe H H
1-103 Ph 4-Pyr SO₂NH- (CH₂)₂-SMe H H
1-104 Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂        H H
1-105 Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe H H
1-106 Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂      H H
1-107 Ph 4-Pyr SO₂NHCH₂COOH H H
1-108 Ph 4-Pyr SO₂NHCH₂COOEt H H
1-109 Ph 4-Pyr SO₂NHCH (Me) COOEt H H
1-110 Ph 4-Pyr SO₂NHCH₂CONH₂           H H
1-111 Ph 4-Pyr SO₂NHOH H H
1-112 Ph 4-Pyr SO₂NHOMe H H
1-113 Ph 4-Pyr SO₂NHOEt H H
1-114 Ph 4-Pyr SO₂NHOPr H H
1-115 Ph 4-Pyr SO₂NHOAllyl H H
1-116 Ph 4-Pyr SO₂NHOBn H H
1-117 Ph 4-Pyr SO₂NHNH₂               H H
1-118 Ph 4-Pyr SO₂NHNHMe H H
1-119 Ph 4-Pyr SO₂NHN (Me)₂            H H
1-120 3-F-Ph 4-Pyr COOH H H
1-121 3-F-Ph 4-Pyr COOMe H H
1-122 3-F-Ph 4-Pyr COOEt H H
1-123 3-F-Ph 4-Pyr COOPr H H
1-124 3-F-Ph 4-Pyr COO-i-Pr H H
1-125 3-F-Ph 4-Pyr COOBu H H
1-126 3-F-Ph 4-Pyr COOBn H H
1-127 3-F-Ph 4-Pyr COOPh H H
1-128 3-F-Ph 4-Pyr CONH₂                  H H
1-129 3-F-Ph 4-Pyr CONHMe H H
1-130 3-F-Ph 4-Pyr CONHEt H H
1-131 3-F-Ph 4-Pyr CONHPr H H
1-132 3-F-Ph 4-Pyr CONH-i-Pr H H
1-133 3-F-Ph 4-Pyr CONHBu H H
1-134 3-F-Ph 4-Pyr CONHBn H H
1-135 3-F-Ph 4-Pyr CONMe₂                 H H
1-136 3-F-Ph 4-Pyr CONH-c-Pr H H
1-137 3-F-Ph 4-Pyr CONH-c-Bu H H
1-138 3-F-Ph 4-Pyr CONH-c-Pen H H
1-139 3-F-Ph 4-Pyr CONH-c-Hex H H
1-140 3-F-Ph 4-Pyr CONH-c-Hep H H
1-141 3-F-Ph 4-Pyr CONHCH₂-c-Pr H H
1-142 3-F-Ph 4-Pyr CONH-Allyl H H
1-143 3-F-Ph 4-Pyr CONH-Propargyl H H
1-144 3-F-Ph 4-Pyr CONHPh H H
1-145 3-F-Ph 4-Pyr CONH-3-Pyr H H
1-146 3-F-Ph 4-Pyr CONHCH₂-4-Pyr H H
1-147 3-F-Ph 4-Pyr CONH- (CH₂)₂-OH H H
1-148 3-F-Ph 4-Pyr CONHCH (CH₂OH)₂          H H
1-149 3-F-Ph 4-Pyr CONH- (CH₂)₂-OAc H H
1-150 3-F-Ph 4-Pyr CONHCH₂CN H H
1-151 3-F-Ph 4-Pyr CONH- (CH₂)₂-F H H
1-152 3-F-Ph 4-Pyr CONH- (CH₂)₂-OMe H H
1-153 3-F-Ph 4-Pyr CONH- (CH₂)₂-SMe H H
1-154 3-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂          H H
1-155 3-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe H H
1-156 3-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂       H H
1-157 3-F-Ph 4-Pyr CONHCH₂COOH H H
1-158 3-F-Ph 4-Pyr CONHCH₂COOEt H H
1-159 3-F-Ph 4-Pyr CONHCH (Me) COOEt H H
1-160 3-F-Ph 4-Pyr CONHCH₂CONH₂            H H
1-161 3-F-Ph 4-Pyr CONHOH H H
1-162 3-F-Ph 4-Pyr CONHOMe H H
1-163 3-F-Ph 4-Pyr CONHOEt H H
1-164 3-F-Ph 4-Pyr CONHOPr H H
1-165 3-F-Ph 4-Pyr CONHOAllyl H H
1-166 3-F-Ph 4-Pyr CONHOBn H H
1-167 3-F-Ph 4-Pyr CONHNH₂                H H
1-168 3-F-Ph 4-Pyr CONHNHMe H H
1-169 3-F-Ph 4-Pyr CONHN (Me)₂             H H
1-170 3-F-Ph 4-Pyr COMe H H
1-171 3-F-Ph 4-Pyr COEt H H
1-172 3-F-Ph 4-Pyr COPr H H
1-173 3-F-Ph 4-Pyr CO-i-Pr H H
1-174 3-F-Ph 4-Pyr COBu H H
1-175 3-F-Ph 4-Pyr COCF_Three                  H H
1-176 3-F-Ph 4-Pyr CO- (CH₂)₂-F H H
1-177 3-F-Ph 4-Pyr CO- (CH₂)₂-OH H H
1-178 3-F-Ph 4-Pyr CO- (CH₂)₂-OMe H H
1-179 3-F-Ph 4-Pyr SOMe H H
1-180 3-F-Ph 4-Pyr SOEt H H
1-181 3-F-Ph 4-Pyr SOPr H H
1-182 3-F-Ph 4-Pyr SO-i-Pr H H
1-183 3-F-Ph 4-Pyr SOBu H H
1-184 3-F-Ph 4-Pyr SOCF_Three                  H H
1-185 3-F-Ph 4-Pyr SO- (CH₂)₂-F              H H
1-186 3-F-Ph 4-Pyr SO- (CH₂)₂-OH H H
1-187 3-F-Ph 4-Pyr SO- (CH₂)₂-OMe H H
1-188 3-F-Ph 4-Pyr SO₂Me H H
1-189 3-F-Ph 4-Pyr SO₂Et H H
1-190 3-F-Ph 4-Pyr SO₂Pr H H
1-191 3-F-Ph 4-Pyr SO₂-i-Pr H H
1-192 3-F-Ph 4-Pyr SO₂Bu H H
1-193 3-F-Ph 4-Pyr SO₂CF_Three                 H H
1-194 3-F-Ph 4-Pyr SO₂-(CH₂)₂-F H H
1-195 3-F-Ph 4-Pyr SO₂-(CH₂)₂-OH H H
1-196 3-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe H H
1-197 3-F-Ph 4-Pyr SO₂NH₂                  H H
1-198 3-F-Ph 4-Pyr SO₂NHMe H H
1-199 3-F-Ph 4-Pyr SO₂NHEt H H
1-200 3-F-Ph 4-Pyr SO₂NHPr H H
1-201 3-F-Ph 4-Pyr SO₂NH-i-Pr H H
1-202 3-F-Ph 4-Pyr SO₂NHBu H H
1-203 3-F-Ph 4-Pyr SO₂NHBn H H
1-204 3-F-Ph 4-Pyr SO₂NMe₂                H H
1-205 3-F-Ph 4-Pyr SO₂NH-c-Pr H H
1-206 3-F-Ph 4-Pyr SO₂NH-c-Bu H H
1-207 3-F-Ph 4-Pyr SO₂NH-c-Pen H H
1-208 3-F-Ph 4-Pyr SO₂NH-c-Hex H H
1-209 3-F-Ph 4-Pyr SO₂NH-c-Hep H H
1-210 3-F-Ph 4-Pyr SO₂NHCH₂-c-Pr H H
1-211 3-F-Ph 4-Pyr SO₂NH-Allyl H H
1-212 3-F-Ph 4-Pyr SO₂NH-Propargyl H H
1-213 3-F-Ph 4-Pyr SO₂NHPh H H
1-214 3-F-Ph 4-Pyr SO₂NH-3-Pyr H H
1-215 3-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr H H
1-216 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH H H
1-217 3-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂          H H
1-218 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc H H
1-219 3-F-Ph 4-Pyr SO₂NHCH₂CN H H
1-220 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F H H
1-221 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe H H
1-222 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe H H
1-223 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂        H H
1-224 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe H H
1-225 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂      H H
1-226 3-F-Ph 4-Pyr SO₂NHCH₂COOH H H
1-227 3-F-Ph 4-Pyr SO₂NHCH₂COOEt H H
1-228 3-F-Ph 4-Pyr SO₂NHCH (Me) COOEt H H
1-229 3-F-Ph 4-Pyr SO₂NHCH₂CONH₂           H H
1-230 3-F-Ph 4-Pyr SO₂NHOH H H
1-231 3-F-Ph 4-Pyr SO₂NHOMe H H
1-232 3-F-Ph 4-Pyr SO₂NHOEt H H
1-233 3-F-Ph 4-Pyr SO₂NHOPr H H
1-234 3-F-Ph 4-Pyr SO₂NHOAllyl H H
1-235 3-F-Ph 4-Pyr SO₂NHOBn H H
1-236 3-F-Ph 4-Pyr SO₂NHNH₂                H H
1-237 3-F-Ph 4-Pyr SO₂NHNHMe H H
1-238 3-F-Ph 4-Pyr SO₂NHN (Me)₂             H H
1-239 3-Cl-Ph 4-Pyr COOH H H
1-240 3-Cl-Ph 4-Pyr COOMe H H
1-241 3-Cl-Ph 4-Pyr COOEt H H
1-242 3-Cl-Ph 4-Pyr COOPr H H
1-243 3-Cl-Ph 4-Pyr COO-i-Pr H H
1-244 3-Cl-Ph 4-Pyr COOBu H H
1-245 3-Cl-Ph 4-Pyr COOBn H H
1-246 3-Cl-Ph 4-Pyr COOPh H H
1-247 3-Cl-Ph 4-Pyr CONH₂                  H H
1-248 3-Cl-Ph 4-Pyr CONHMe H H
1-249 3-Cl-Ph 4-Pyr CONHEt H H
1-250 3-Cl-Ph 4-Pyr CONHPr H H
1-251 3-Cl-Ph 4-Pyr CONH-i-Pr H H
1-252 3-Cl-Ph 4-Pyr CONHBu H H
1-253 3-Cl-Ph 4-Pyr CONHBn H H
1-254 3-Cl-Ph 4-Pyr CONMe₂                 H H
1-255 3-Cl-Ph 4-Pyr CONH-c-Pr H H
1-256 3-Cl-Ph 4-Pyr CONH-c-Bu H H
1-257 3-Cl-Ph 4-Pyr CONH-c-Pen H H
1-258 3-Cl-Ph 4-Pyr CONH-c-Hex H H
1-259 3-Cl-Ph 4-Pyr CONH-c-Hep H H
1-260 3-Cl-Ph 4-Pyr CONHCH₂-c-Pr H H
1-261 3-Cl-Ph 4-Pyr CONH-Allyl H H
1-262 3-Cl-Ph 4-Pyr CONH-Propargyl H H
1-263 3-Cl-Ph 4-Pyr CONHPh H H
1-264 3-Cl-Ph 4-Pyr CONH-3-Pyr H H
1-265 3-Cl-Ph 4-Pyr CONHCH₂-4-Pyr H H
1-266 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OH H H
1-267 3-Cl-Ph 4-Pyr CONHCH (CH₂OH)₂          H H
1-268 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OAc H H
1-269 3-Cl-Ph 4-Pyr CONHCH₂CN H H
1-270 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-F H H
1-271 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OMe H H
1-272 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-SMe H H
1-273 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-NH₂          H H
1-274 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-NHMe H H
1-275 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂       H H
1-276 3-Cl-Ph 4-Pyr CONHCH₂COOH H H
1-277 3-Cl-Ph 4-Pyr CONHCH₂COOEt H H
1-278 3-Cl-Ph 4-Pyr CONHCH (Me) COOEt H H
1-279 3-Cl-Ph 4-Pyr CONHCH₂CONH₂            H H
1-280 3-Cl-Ph 4-Pyr CONHOH H H
1-281 3-Cl-Ph 4-Pyr CONHOMe H H
1-282 3-Cl-Ph 4-Pyr CONHOEt H H
1-283 3-Cl-Ph 4-Pyr CONHOPr H H
1-284 3-Cl-Ph 4-Pyr CONHOAllyl H H
1-285 3-Cl-Ph 4-Pyr CONHOBn H H
1-286 3-Cl-Ph 4-Pyr CONHNH₂                H H
1-287 3-Cl-Ph 4-Pyr CONHNHMe H H
1-288 3-Cl-Ph 4-Pyr CONHN (Me)₂             H H
1-289 3-Cl-Ph 4-Pyr COMe H H
1-290 3-Cl-Ph 4-Pyr COEt H H
1-291 3-Cl-Ph 4-Pyr COPr H H
1-292 3-Cl-Ph 4-Pyr CO-i-Pr H H
1-293 3-Cl-Ph 4-Pyr COBu H H
1-294 3-Cl-Ph 4-Pyr COCF_Three                   H H
1-295 3-Cl-Ph 4-Pyr CO- (CH₂)₂-F H H
1-296 3-Cl-Ph 4-Pyr CO- (CH₂)₂-OH H H
1-297 3-Cl-Ph 4-Pyr CO- (CH₂)₂-OMe H H
1-298 3-Cl-Ph 4-Pyr SOMe H H
1-299 3-Cl-Ph 4-Pyr SOEt H H
1-300 3-Cl-Ph 4-Pyr SOPr H H
1-301 3-Cl-Ph 4-Pyr SO-i-Pr H H
1-302 3-Cl-Ph 4-Pyr SOBu H H
1-303 3-Cl-Ph 4-Pyr SOCF_Three                   H H
1-304 3-Cl-Ph 4-Pyr SO- (CH₂)₂-F H H
1-305 3-Cl-Ph 4-Pyr SO- (CH₂)₂-OH H H
1-306 3-Cl-Ph 4-Pyr SO- (CH₂)₂-OMe H H
1-307 3-Cl-Ph 4-Pyr SO₂Me H H
1-308 3-Cl-Ph 4-Pyr SO₂Et H H
1-309 3-Cl-Ph 4-Pyr SO₂Pr H H
1-310 3-Cl-Ph 4-Pyr SO₂-i-Pr H H
1-311 3-Cl-Ph 4-Pyr SO₂Bu H H
1-312 3-Cl-Ph 4-Pyr SO₂CF_Three                  H H
1-313 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-F H H
1-314 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-OH H H
1-315 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-OMe H H
1-316 3-Cl-Ph 4-Pyr SO₂NH₂                  H H
1-317 3-Cl-Ph 4-Pyr SO₂NHMe H H
1-318 3-Cl-Ph 4-Pyr SO₂NHEt H H
1-319 3-Cl-Ph 4-Pyr SO₂NHPr H H
1-320 3-Cl-Ph 4-Pyr SO₂NH-i-Pr H H
1-321 3-Cl-Ph 4-Pyr SO₂NHBu H H
1-322 3-Cl-Ph 4-Pyr SO₂NHBn H H
1-323 3-Cl-Ph 4-Pyr SO₂NMe₂                H H
1-324 3-Cl-Ph 4-Pyr SO₂NH-c-Pr H H
1-325 3-Cl-Ph 4-Pyr SO₂NH-c-Bu H H
1-326 3-Cl-Ph 4-Pyr SO₂NH-c-Pen H H
1-327 3-Cl-Ph 4-Pyr SO₂NH-c-Hex H H
1-328 3-Cl-Ph 4-Pyr SO₂NH-c-Hep H H
1-329 3-Cl-Ph 4-Pyr SO₂NHCH₂-c-Pr H H
1-330 3-Cl-Ph 4-Pyr SO₂NH-Allyl H H
1-331 3-Cl-Ph 4-Pyr SO₂NH-Propargyl H H
1-332 3-Cl-Ph 4-Pyr SO₂NHPh H H
1-333 3-Cl-Ph 4-Pyr SO₂NH-3-Pyr H H
1-334 3-Cl-Ph 4-Pyr SO₂NHCH₂-4-Pyr H H
1-335 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OH H H
1-336 3-Cl-Ph 4-Pyr SO₂NHCH (CH₂OH)₂          H H
1-337 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc H H
1-338 3-Cl-Ph 4-Pyr SO₂NHCH₂CN H H
1-339 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-F H H
1-340 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe H H
1-341 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe H H
1-342 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂         H H
1-343 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe H H
1-344 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂     H H
1-345 3-Cl-Ph 4-Pyr SO₂NHCH₂COOH H H
1-346 3-Cl-Ph 4-Pyr SO₂NHCH₂COOEt H H
1-347 3-Cl-Ph 4-Pyr SO₂NHCH (Me) COOEt H H
1-348 3-Cl-Ph 4-Pyr SO₂NHCH₂CONH₂           H H
1-349 3-Cl-Ph 4-Pyr SO₂NHOH H H
1-350 3-Cl-Ph 4-Pyr SO₂NHOMe H H
1-351 3-Cl-Ph 4-Pyr SO₂NHOEt H H
1-352 3-Cl-Ph 4-Pyr SO₂NHOPr H H
1-353 3-Cl-Ph 4-Pyr SO₂NHOAllyl H H
1-354 3-Cl-Ph 4-Pyr SO₂NHOBn H H
1-355 3-Cl-Ph 4-Pyr SO₂NHNH₂                H H
1-356 3-Cl-Ph 4-Pyr SO₂NHNHMe H H
1-357 3-Cl-Ph 4-Pyr SO₂NHN (Me)₂             H H
1-358 4-F-Ph 4-Pyr COOH H H
1-359 4-F-Ph 4-Pyr COOMe H H
1-360 4-F-Ph 4-Pyr COOEt H H
1-361 4-F-Ph 4-Pyr COOPr H H
1-362 4-F-Ph 4-Pyr COO-i-Pr H H
1-363 4-F-Ph 4-Pyr COOBu H H
1-364 4-F-Ph 4-Pyr COOBn H H
1-365 4-F-Ph 4-Pyr COOPh H H
1-366 4-F-Ph 4-Pyr CONH₂                   H H
1-367 4-F-Ph 4-Pyr CONHMe H H
1-368 4-F-Ph 4-Pyr CONHEt H H
1-369 4-F-Ph 4-Pyr CONHPr H H
1-370 4-F-Ph 4-Pyr CONH-i-Pr H H
1-371 4-F-Ph 4-Pyr CONHBu H H
1-372 4-F-Ph 4-Pyr CONHBn H H
1-373 4-F-Ph 4-Pyr CONMe₂                  H H
1-374 4-F-Ph 4-Pyr CONH-c-Pr H H
1-375 4-F-Ph 4-Pyr CONH-c-Bu H H
1-376 4-F-Ph 4-Pyr CONH-c-Pen H H
1-377 4-F-Ph 4-Pyr CONH-c-Hex H H
1-378 4-F-Ph 4-Pyr CONH-c-Hep H H
1-379 4-F-Ph 4-Pyr CONHCH₂-c-Pr H H
1-380 4-F-Ph 4-Pyr CONH-Allyl H H
1-381 4-F-Ph 4-Pyr CONH-Propargyl H H
1-382 4-F-Ph 4-Pyr CONHPh H H
1-383 4-F-Ph 4-Pyr CONH-3-Pyr H H
1-384 4-F-Ph 4-Pyr CONHCH₂-4-Pyr H H
1-385 4-F-Ph 4-Pyr CONH- (CH₂)₂-OH H H
1-386 4-F-Ph 4-Pyr CONHCH (CH₂OH)₂          H H
1-387 4-F-Ph 4-Pyr CONH- (CH₂)₂-OAc H H
1-388 4-F-Ph 4-Pyr CONHCH₂CN H H
1-389 4-F-Ph 4-Pyr CONH- (CH₂)₂-F H H
1-390 4-F-Ph 4-Pyr CONH- (CH₂)₂-OMe H H
1-391 4-F-Ph 4-Pyr CONH- (CH₂)₂-SMe H H
1-392 4-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂          H H
1-393 4-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe         H H
1-394 4-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂       H H
1-395 4-F-Ph 4-Pyr CONHCH₂COOH H H
1-396 4-F-Ph 4-Pyr CONHCH₂COOEt H H
1-397 4-F-Ph 4-Pyr CONHCH (Me) COOEt H H
1-398 4-F-Ph 4-Pyr CONHCH₂CONH₂            H H
1-399 4-F-Ph 4-Pyr CONHOH H H
1-400 4-F-Ph 4-Pyr CONHOMe H H
1-401 4-F-Ph 4-Pyr CONHOEt H H
1-402 4-F-Ph 4-Pyr CONHOPr H H
1-403 4-F-Ph 4-Pyr CONHOAllyl H H
1-404 4-F-Ph 4-Pyr CONHOBn H H
1-405 4-F-Ph 4-Pyr CONHNH₂                 H H
1-406 4-F-Ph 4-Pyr CONHNHMe H H
1-407 4-F-Ph 4-Pyr CONHN (Me)₂              H H
1-408 4-F-Ph 4-Pyr COMe H H
1-409 4-F-Ph 4-Pyr COEt H H
1-410 4-F-Ph 4-Pyr COPr H H
1-411 4-F-Ph 4-Pyr CO-i-Pr H H
1-412 4-F-Ph 4-Pyr COBu H H
1-413 4-F-Ph 4-Pyr COCF_Three                   H H
1-414 4-F-Ph 4-Pyr CO- (CH₂)₂-F              H H
1-415 4-F-Ph 4-Pyr CO- (CH₂)₂-OH H H
1-416 4-F-Ph 4-Pyr CO- (CH₂)₂-OMe H H
1-417 4-F-Ph 4-Pyr SOMe H H
1-418 4-F-Ph 4-Pyr SOEt H H
1-419 4-F-Ph 4-Pyr SOPr H H
1-420 4-F-Ph 4-Pyr SO-i-Pr H H
1-421 4-F-Ph 4-Pyr SOBu H H
1-422 4-F-Ph 4-Pyr SOCF_Three                   H H
1-423 4-F-Ph 4-Pyr SO- (CH₂)₂-F H H
1-424 4-F-Ph 4-Pyr SO- (CH₂)₂-OH H H
1-425 4-F-Ph 4-Pyr SO- (CH₂)₂-OMe H H
1-426 4-F-Ph 4-Pyr SO₂Me H H
1-427 4-F-Ph 4-Pyr SO₂Et H H
1-428 4-F-Ph 4-Pyr SO₂Pr H H
1-429 4-F-Ph 4-Pyr SO₂-i-Pr H H
1-430 4-F-Ph 4-Pyr SO₂Bu H H
1-431 4-F-Ph 4-Pyr SO₂CF_Three                  H H
1-432 4-F-Ph 4-Pyr SO₂-(CH₂)₂-F H H
1-433 4-F-Ph 4-Pyr SO₂-(CH₂)₂-OH H H
1-434 4-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe H H
1-435 4-F-Ph 4-Pyr SO₂NH₂                   H H
1-436 4-F-Ph 4-Pyr SO₂NHMe H H
1-437 4-F-Ph 4-Pyr SO₂NHEt H H
1-438 4-F-Ph 4-Pyr SO₂NHPr H H
1-439 4-F-Ph 4-Pyr SO₂NH-i-Pr H H
1-440 4-F-Ph 4-Pyr SO₂NHBu H H
1-441 4-F-Ph 4-Pyr SO₂NHBn H H
1-442 4-F-Ph 4-Pyr SO₂NMe₂                 H H
1-443 4-F-Ph 4-Pyr SO₂NH-c-Pr H H
1-444 4-F-Ph 4-Pyr SO₂NH-c-Bu H H
1-445 4-F-Ph 4-Pyr SO₂NH-c-Pen H H
1-446 4-F-Ph 4-Pyr SO₂NH-c-Hex H H
1-447 4-F-Ph 4-Pyr SO₂NH-c-Hep H H
1-448 4-F-Ph 4-Pyr SO₂NHCH₂-c-Pr H H
1-449 4-F-Ph 4-Pyr SO₂NH-Allyl H H
1-450 4-F-Ph 4-Pyr SO₂NH-Propargyl H H
1-451 4-F-Ph 4-Pyr SO₂NHPh H H
1-452 4-F-Ph 4-Pyr SO₂NH-3-Pyr H H
1-453 4-F-Ph 4-Pyr SO₂NHCH₂-3-Pyr H H
1-454 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH H H
1-455 4-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂          H H
1-456 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc H H
1-457 4-F-Ph 4-Pyr SO₂NHCH₂CN H H
1-458 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F H H
1-459 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe H H
1-460 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe H H
1-461 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂         H H
1-462 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe H H
1-463 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂      H H
1-464 4-F-Ph 4-Pyr SO₂NHCH₂COOH H H
1-465 4-F-Ph 4-Pyr SO₂NHCH₂COOMe            H H
1-466 4-F-Ph 4-Pyr SO₂NHCH (Me) COOEt H H
1-467 4-F-Ph 4-Pyr SO₂NHCH₂CONH₂           H H
1-468 4-F-Ph 4-Pyr SO₂NHOH H H
1-469 4-F-Ph 4-Pyr SO₂NHOMe H H
1-470 4-F-Ph 4-Pyr SO₂NHOEt H H
1-471 4-F-Ph 4-Pyr SO₂NHOPr H H
1-472 4-F-Ph 4-Pyr SO₂NHOAllyl H H
1-473 4-F-Ph 4-Pyr SO₂NHOBn H H
1-474 4-F-Ph 4-Pyr SO₂NHNH₂                H H
1-475 4-F-Ph 4-Pyr SO₂NHNHMe H H
1-476 4-F-Ph 4-Pyr SO₂NHN (Me)₂             H H
1-477 3-Cl-4-F-Ph 4-Pyr COOH H H
1-478 3-Cl-4-F-Ph 4-Pyr COOMe H H
1-479 3-Cl-4-F-Ph 4-Pyr COOEt H H
1-480 3-Cl-4-F-Ph 4-Pyr COOPr H H
1-481 3-Cl-4-F-Ph 4-Pyr COO-i-Pr H H
1-482 3-Cl-4-F-Ph 4-Pyr COOBu H H
1-483 3-Cl-4-F-Ph 4-Pyr COOBn H H
1-484 3-Cl-4-F-Ph 4-Pyr COOPh H H
1-485 3-Cl-4-F-Ph 4-Pyr CONH₂                  H H
1-486 3-Cl-4-F-Ph 4-Pyr CONHMe H H
1-487 3-Cl-4-F-Ph 4-Pyr CONHEt H H
1-488 3-Cl-4-F-Ph 4-Pyr CONHPr H H
1-489 3-Cl-4-F-Ph 4-Pyr CONH-i-Pr H H
1-490 3-Cl-4-F-Ph 4-Pyr CONHBu H H
1-491 3-Cl-4-F-Ph 4-Pyr CONHBn H H
1-492 3-Cl-4-F-Ph 4-Pyr CONMe₂                 H H
1-493 3-Cl-4-F-Ph 4-Pyr CONH-c-Pr H H
1-494 3-Cl-4-F-Ph 4-Pyr CONH-c-Bu H H
1-495 3-Cl-4-F-Ph 4-Pyr CONH-c-Pen H H
1-496 3-Cl-4-F-Ph 4-Pyr CONH-c-Hex H H
1-497 3-Cl-4-F-Ph 4-Pyr CONH-c-Hep H H
1-498 3-Cl-4-F-Ph 4-Pyr CONHCH₂-c-Pr H H
1-499 3-Cl-4-F-Ph 4-Pyr CONH-Allyl H H
1-500 3-Cl-4-F-Ph 4-Pyr CONH-Propargyl H H
1-501 3-Cl-4-F-Ph 4-Pyr CONHPh H H
1-502 3-Cl-4-F-Ph 4-Pyr CONH-3-Pyr H H
1-503 3-Cl-4-F-Ph 4-Pyr CONHCH₂-4-Pyr H H
1-504 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OH H H
1-505 3-Cl-4-F-Ph 4-Pyr CONHCH (CH₂OH)₂          H H
1-506 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OAc H H
1-507 3-Cl-4-F-Ph 4-Pyr CONHCH₂CN H H
1-508 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-F H H
1-509 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OMe H H
1-510 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-SMe H H
1-511 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂          H H
1-512 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe H H
1-513 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂       H H
1-514 3-Cl-4-F-Ph 4-Pyr CONHCH₂COOH H H
1-515 3-Cl-4-F-Ph 4-Pyr CONHCH₂COOEt H H
1-516 3-Cl-4-F-Ph 4-Pyr CONHCH (Me) COOEt H H
1-517 3-Cl-4-F-Ph 4-Pyr CONHCH₂CONH₂            H H
1-518 3-Cl-4-F-Ph 4-Pyr CONHOH H H
1-519 3-Cl-4-F-Ph 4-Pyr CONHOMe H H
1-520 3-Cl-4-F-Ph 4-Pyr CONHOEt H H
1-521 3-Cl-4-F-Ph 4-Pyr CONHOPr H H
1-522 3-Cl-4-F-Ph 4-Pyr CONHOAllyl H H
1-523 3-Cl-4-F-Ph 4-Pyr CONHOBn H H
1-524 3-Cl-4-F-Ph 4-Pyr CONHNH₂                 H H
1-525 3-Cl-4-F-Ph 4-Pyr CONHNHMe H H
1-526 3-Cl-4-F-Ph 4-Pyr CONHN (Me)₂             H H
1-527 3-Cl-4-F-Ph 4-Pyr COMe H H
1-528 3-Cl-4-F-Ph 4-Pyr COEt H H
1-529 3-Cl-4-F-Ph 4-Pyr COPr H H
1-530 3-Cl-4-F-Ph 4-Pyr CO-i-Pr H H
1-531 3-Cl-4-F-Ph 4-Pyr COBu H H
1-532 3-Cl-4-F-Ph 4-Pyr COCF_Three                   H H
1-533 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-F H H
1-534 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-OH H H
1-535 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-OMe H H
1-536 3-Cl-4-F-Ph 4-Pyr SOMe H H
1-537 3-Cl-4-F-Ph 4-Pyr SOEt H H
1-538 3-Cl-4-F-Ph 4-Pyr SOPr H H
1-539 3-Cl-4-F-Ph 4-Pyr SO-i-Pr H H
1-540 3-Cl-4-F-Ph 4-Pyr SOBu H H
1-541 3-Cl-4-F-Ph 4-Pyr SOCF_Three                  H H
1-542 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-F H H
1-543 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-OH H H
1-544 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-OMe H H
1-545 3-Cl-4-F-Ph 4-Pyr SO₂Me H H
1-546 3-Cl-4-F-Ph 4-Pyr SO₂Et H H
1-547 3-Cl-4-F-Ph 4-Pyr SO₂Pr H H
1-548 3-Cl-4-F-Ph 4-Pyr SO₂-i-Pr H H
1-549 3-Cl-4-F-Ph 4-Pyr SO₂Bu H H
1-550 3-Cl-4-F-Ph 4-Pyr SO₂CF_Three                  H H
1-551 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-F H H
1-552 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-OH H H
1-553 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe H H
1-554 3-Cl-4-F-Ph 4-Pyr SO₂NH₂                  H H
1-555 3-Cl-4-F-Ph 4-Pyr SO₂NHMe H H
1-556 3-Cl-4-F-Ph 4-Pyr SO₂NHEt H H
1-557 3-Cl-4-F-Ph 4-Pyr SO₂NHPr H H
1-558 3-Cl-4-F-Ph 4-Pyr SO₂NH-i-Pr H H
1-559 3-Cl-4-F-Ph 4-Pyr SO₂NHBu H H
1-560 3-Cl-4-F-Ph 4-Pyr SO₂NHBn H H
1-561 3-Cl-4-F-Ph 4-Pyr SO₂NMe₂                H H
1-562 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Pr H H
1-563 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Bu H H
1-564 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Pen H H
1-565 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Hex H H
1-566 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Hep H H
1-567 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂-c-Pr H H
1-568 3-Cl-4-F-Ph 4-Pyr SO₂NH-Allyl H H
1-569 3-Cl-4-F-Ph 4-Pyr SO₂NH-Propargyl H H
1-570 3-Cl-4-F-Ph 4-Pyr SO₂NHPh H H
1-571 3-Cl-4-F-Ph 4-Pyr SO₂NH-3-Pyr H H
1-572 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr H H
1-573 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH H H
1-574 3-Cl-4-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂          H H
1-575 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc H H
1-576 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂CN H H
1-577 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F H H
1-578 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe H H
1-579 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe H H
1-580 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂        H H
1-581 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe H H
1-582 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂      H H
1-583 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂COOH H H
1-584 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂COOEt H H
1-585 3-Cl-4-F-Ph 4-Pyr SO₂NHCH (Me) COOEt H H
1-586 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂CONH₂           H H
1-587 3-Cl-4-F-Ph 4-Pyr SO₂NHOH H H
1-588 3-Cl-4-F-Ph 4-Pyr SO₂NHOMe H H
1-589 3-Cl-4-F-Ph 4-Pyr SO₂NHOEt H H
1-590 3-Cl-4-F-Ph 4-Pyr SO₂NHOPr H H
1-591 3-Cl-4-F-Ph 4-Pyr SO₂NHOAllyl H H
1-592 3-Cl-4-F-Ph 4-Pyr SO₂NHOBn H H
1-593 3-Cl-4-F-Ph 4-Pyr SO₂NHNH₂               H H
1-594 3-Cl-4-F-Ph 4-Pyr SO₂NHNHMe H H
1-595 3-Cl-4-F-Ph 4-Pyr SO₂NHN (Me)₂             H H
1-596 3,4-F₂-Ph       4-Pyr COOH H H
1-597 3,4-F₂-Ph       4-Pyr COOMe H H
1-598 3,4-F₂-Ph       4-Pyr COOEt H H
1-599 3,4-F₂-Ph       4-Pyr COOPr H H
1-600 3,4-F₂-Ph       4-Pyr COO-i-Pr H H
1-601 3,4-F₂-Ph       4-Pyr COOBu H H
1-602 3,4-F₂-Ph       4-Pyr COOBn H H
1-603 3,4-F₂-Ph       4-Pyr COOPh H H
1-604 3,4-F₂-Ph       4-Pyr CONH₂                  H H
1-605 3,4-F₂-Ph       4-Pyr CONHMe H H
1-606 3,4-F₂-Ph       4-Pyr CONHEt H H
1-607 3,4-F₂-Ph       4-Pyr CONHPr H H
1-608 3,4-F₂-Ph       4-Pyr CONH-i-Pr H H
1-609 3,4-F₂-Ph       4-Pyr CONHBu H H
1-610 3,4-F₂-Ph       4-Pyr CONHBn H H
1-611 3,4-F₂-Ph       4-Pyr CONMe₂                  H H
1-612 3,4-F₂-Ph       4-Pyr CONH-c-Pr H H
1-613 3,4-F₂-Ph       4-Pyr CONH-c-Bu H H
1-614 3,4-F₂-Ph       4-Pyr CONH-c-Pen H H
1-615 3,4-F₂-Ph       4-Pyr CONH-c-Hex H H
1-616 3,4-F₂-Ph       4-Pyr CONH-c-Hep H H
1-617 3,4-F₂-Ph       4-Pyr CONHCH₂-c-Pr H H
1-618 3,4-F₂-Ph       4-Pyr CONH-Allyl H H
1-619 3,4-F₂-Ph       4-Pyr CONH-Propargyl H H
1-620 3,4-F₂-Ph       4-Pyr CONHPh H H
1-621 3,4-F₂-Ph       4-Pyr CONH-3-Pyr H H
1-622 3,4-F₂-Ph       4-Pyr CONHCH₂-4-Pyr H H
1-623 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-OH H H
1-624 3,4-F₂-Ph       4-Pyr CONHCH (CH₂OH)₂          H H
1-625 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-OAc H H
1-626 3,4-F₂-Ph       4-Pyr CONHCH₂CN H H
1-627 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-F H H
1-628 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-OMe H H
1-629 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-SMe H H
1-630 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-NH₂          H H
1-631 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-NHMe H H
1-632 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-N (Me)₂       H H
1-633 3,4-F₂-Ph       4-Pyr CONHCH₂COOH H H
1-634 3,4-F₂-Ph       4-Pyr CONHCH₂COOEt H H
1-635 3,4-F₂-Ph       4-Pyr CONHCH (Me) COOEt H H
1-636 3,4-F₂-Ph       4-Pyr CONHCH₂CONH₂            H H
1-637 3,4-F₂-Ph       4-Pyr CONHOH H H
1-638 3,4-F₂-Ph       4-Pyr CONHOMe H H
1-639 3,4-F₂-Ph       4-Pyr CONHOEt H H
1-640 3,4-F₂-Ph       4-Pyr CONHOPr H H
1-641 3,4-F₂-Ph       4-Pyr CONHOAllyl H H
1-642 3,4-F₂-Ph       4-Pyr CONHOBn H H
1-643 3,4-F₂-Ph       4-Pyr CONHNH₂                H H
1-644 3,4-F₂-Ph       4-Pyr CONHNHMe H H
1-645 3,4-F₂-Ph       4-Pyr CONHN (Me)₂             H H
1-646 3,4-F₂-Ph       4-Pyr COMe H H
1-647 3,4-F₂-Ph       4-Pyr COEt H H
1-648 3,4-F₂-Ph       4-Pyr COPr H H
1-649 3,4-F₂-Ph       4-Pyr CO-i-Pr H H
1-650 3,4-F₂-Ph       4-Pyr COBu H H
1-651 3,4-F₂-Ph       4-Pyr COCF_Three                  H H
1-652 3,4-F₂-Ph       4-Pyr CO- (CH₂)₂-F              H H
1-653 3,4-F₂-Ph       4-Pyr CO- (CH₂)₂-OH             H H
1-654 3,4-F₂-Ph       4-Pyr CO- (CH₂)₂-OMe            H H
1-655 3,4-F₂-Ph       4-Pyr SOMe H H
1-656 3,4-F₂-Ph       4-Pyr SOEt H H
1-657 3,4-F₂-Ph       4-Pyr SOPr H H
1-658 3,4-F₂-Ph       4-Pyr SO-i-Pr H H
1-659 3,4-F₂-Ph       4-Pyr SOBu H H
1-660 3,4-F₂-Ph       4-Pyr SOCF_Three                   H H
1-661 3,4-F₂-Ph       4-Pyr SO- (CH₂)₂-F              H H
1-662 3,4-F₂-Ph       4-Pyr SO- (CH₂)₂-OH             H H
1-663 3,4-F₂-Ph       4-Pyr SO- (CH₂)₂-OMe            H H
1-664 3,4-F₂-Ph       4-Pyr SO₂Me H H
1-665 3,4-F₂-Ph       4-Pyr SO₂Et H H
1-666 3,4-F₂-Ph       4-Pyr SO₂Pr H H
1-667 3,4-F₂-Ph       4-Pyr SO₂-i-Pr H H
1-668 3,4-F₂-Ph       4-Pyr SO₂Bu H H
1-669 3,4-F₂-Ph       4-Pyr SO₂CF_Three                  H H
1-670 3,4-F₂-Ph       4-Pyr SO₂-(CH₂)₂-F              H H
1-671 3,4-F₂-Ph       4-Pyr SO₂-(CH₂)₂-OH             H H
1-672 3,4-F₂-Ph       4-Pyr SO₂-(CH₂)₂-OMe            H H
1-673 3,4-F₂-Ph       4-Pyr SO₂NH₂                  H H
1-674 3,4-F₂-Ph       4-Pyr SO₂NHMe H H
1-675 3,4-F₂-Ph       4-Pyr SO₂NHEt H H
1-676 3,4-F₂-Ph       4-Pyr SO₂NHPr H H
1-677 3,4-F₂-Ph       4-Pyr SO₂NH-i-Pr H H
1-678 3,4-F₂-Ph       4-Pyr SO₂NHBu H H
1-679 3,4-F₂-Ph       4-Pyr SO₂NHBn H H
1-680 3,4-F₂-Ph       4-Pyr SO₂NMe₂                H H
1-681 3,4-F₂-Ph       4-Pyr SO₂NH-c-Pr H H
1-682 3,4-F₂-Ph       4-Pyr SO₂NH-c-Bu H H
1-683 3,4-F₂-Ph       4-Pyr SO₂NH-c-Pen H H
1-684 3,4-F₂-Ph       4-Pyr SO₂NH-c-Hex H H
1-685 3,4-F₂-Ph       4-Pyr SO₂NH-c-Hep H H
1-686 3,4-F₂-Ph       4-Pyr SO₂NHCH₂-c-Pr H H
1-687 3,4-F₂-Ph       4-Pyr SO₂NH-Allyl H H
1-688 3,4-F₂-Ph       4-Pyr SO₂NH-Propargyl H H
1-689 3,4-F₂-Ph       4-Pyr SO₂NHPh H H
1-690 3,4-F₂-Ph       4-Pyr SO₂NH-3-Pyr H H
1-691 3,4-F₂-Ph       4-Pyr SO₂NHCH₂-4-Pyr H H
1-692 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-OH H H
1-693 3,4-F₂-Ph       4-Pyr SO₂NHCH (CH₂OH)₂          H H
1-694 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-OAc H H
1-695 3,4-F₂-Ph       4-Pyr SO₂NHCH₂CN H H
1-696 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-F H H
1-697 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-OMe H H
1-698 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-SMe H H
1-699 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-NH₂        H H
1-700 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe H H
1-701 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-N (Me)₂      H H
1-702 3,4-F₂-Ph       4-Pyr SO₂NHCH₂COOH H H
1-703 3,4-F₂-Ph       4-Pyr SO₂NHCH₂COOEt H H
1-704 3,4-F₂-Ph       4-Pyr SO₂NHCH (Me) COOEt H H
1-705 3,4-F₂-Ph       4-Pyr SO₂NHCH₂CONH₂           H H
1-706 3,4-F₂-Ph       4-Pyr SO₂NHOH H H
1-707 3,4-F₂-Ph       4-Pyr SO₂NHOMe H H
1-708 3,4-F₂-Ph       4-Pyr SO₂NHOEt H H
1-709 3,4-F₂-Ph       4-Pyr SO₂NHOPr H H
1-710 3,4-F₂-Ph       4-Pyr SO₂NHOAllyl H H
1-711 3,4-F₂-Ph       4-Pyr SO₂NHOBn H H
1-712 3,4-F₂-Ph       4-Pyr SO₂NHNH₂               H H
1-713 3,4-F₂-Ph       4-Pyr SO₂NHNHMe H H
1-714 3,4-F₂-Ph       4-Pyr SO₂NHN (Me)₂            H H
1-715 3-CF_Three-Ph        4-Pyr COOH H H
1-716 3-CF_Three-Ph        4-Pyr COOMe H H
1-717 3-CF_Three-Ph        4-Pyr COOEt H H
1-718 3-CF_Three-Ph        4-Pyr COOPr H H
1-719 3-CF_Three-Ph        4-Pyr COO-i-Pr H H
1-720 3-CF_Three-Ph        4-Pyr COOBu H H
1-721 3-CF_Three-Ph        4-Pyr COOBn H H
1-722 3-CF_Three-Ph        4-Pyr COOPh H H
1-723 3-CF_Three-Ph        4-Pyr CONH₂                  H H
1-724 3-CF_Three-Ph        4-Pyr CONHMe H H
1-725 3-CF_Three-Ph        4-Pyr CONHEt H H
1-726 3-CF_Three-Ph        4-Pyr CONHPr H H
1-727 3-CF_Three-Ph        4-Pyr CONH-i-Pr H H
1-728 3-CF_Three-Ph        4-Pyr CONHBu H H
1-729 3-CF_Three-Ph        4-Pyr CONHBn H H
1-730 3-CF_Three-Ph        4-Pyr CONMe₂                 H H
1-731 3-CF_Three-Ph        4-Pyr CONH-c-Pr H H
1-732 3-CF_Three-Ph        4-Pyr CONH-c-Bu H H
1-733 3-CF_Three-Ph        4-Pyr CONH-c-Pen H H
1-734 3-CF_Three-Ph        4-Pyr CONH-c-Hex H H
1-735 3-CF_Three-Ph        4-Pyr CONH-c-Hep H H
1-736 3-CF_Three-Ph        4-Pyr CONHCH₂-c-Pr H H
1-737 3-CF_Three-Ph        4-Pyr CONH-Allyl H H
1-738 3-CF_Three-Ph        4-Pyr CONH-Propargyl H H
1-739 3-CF_Three-Ph        4-Pyr CONHPh H H
1-740 3-CF_Three-Ph        4-Pyr CONH-3-Pyr H H
1-741 3-CF_Three-Ph        4-Pyr CONHCH₂-4-Pyr H H
1-742 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-OH H H
1-743 3-CF_Three-Ph        4-Pyr CONHCH (CH₂OH)₂          H H
1-744 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-OAc H H
1-745 3-CF_Three-Ph        4-Pyr CONHCH₂CN H H
1-746 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-F H H
1-747 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-OMe H H
1-748 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-SMe H H
1-749 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-NH₂          H H
1-750 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-NHMe H H
1-751 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-N (Me)₂       H H
1-752 3-CF_Three-Ph        4-Pyr CONHCH₂COOH H H
1-753 3-CF_Three-Ph        4-Pyr CONHCH₂COOEt H H
1-754 3-CF_Three-Ph        4-Pyr CONHCH (Me) COOEt H H
1-755 3-CF_Three-Ph        4-Pyr CONHCH₂CONH₂           H H
1-756 3-CF_Three-Ph        4-Pyr CONHOH H H
1-757 3-CF_Three-Ph        4-Pyr CONHOMe H H
1-758 3-CF_Three-Ph        4-Pyr CONHOEt H H
1-759 3-CF_Three-Ph        4-Pyr CONHOPr H H
1-760 3-CF_Three-Ph        4-Pyr CONHOAllyl H H
1-761 3-CF_Three-Ph        4-Pyr CONHOBn H H
1-762 3-CF_Three-Ph        4-Pyr CONHNH₂                H H
1-763 3-CF_Three-Ph        4-Pyr CONHNHMe H H
1-764 3-CF_Three-Ph        4-Pyr CONHN (Me)₂             H H
1-765 3-CF_Three-Ph        4-Pyr COMe H H
1-766 3-CF_Three-Ph        4-Pyr COEt H H
1-767 3-CF_Three-Ph        4-Pyr COPr H H
1-768 3-CF_Three-Ph        4-Pyr CO-i-Pr H H
1-769 3-CF_Three-Ph        4-Pyr COBu H H
1-770 3-CF_Three-Ph        4-Pyr COCF_Three                  H H
1-771 3-CF_Three-Ph        4-Pyr CO- (CH₂)₂-F              H H
1-772 3-CF_Three-Ph        4-Pyr CO- (CH₂)₂-OH             H H
1-773 3-CF_Three-Ph        4-Pyr CO- (CH₂)₂-OMe            H H
1-774 3-CF_Three-Ph        4-Pyr SOMe H H
1-775 3-CF_Three-Ph        4-Pyr SOEt H H
1-776 3-CF_Three-Ph        4-Pyr SOPr H H
1-777 3-CF_Three-Ph        4-Pyr SO-i-Pr H H
1-778 3-CF_Three-Ph        4-Pyr SOBu H H
1-779 3-CF_Three-Ph        4-Pyr SOCF_Three                   H H
1-780 3-CF_Three-Ph        4-Pyr SO- (CH₂)₂-F              H H
1-781 3-CF_Three-Ph        4-Pyr SO- (CH₂)₂-OH             H H
1-782 3-CF_Three-Ph        4-Pyr SO- (CH₂)₂-OMe            H H
1-783 3-CF_Three-Ph        4-Pyr SO₂Me H H
1-784 3-CF_Three-Ph        4-Pyr SO₂Et H H
1-785 3-CF_Three-Ph        4-Pyr SO₂Pr H H
1-786 3-CF_Three-Ph        4-Pyr SO₂-i-Pr H H
1-787 3-CF_Three-Ph        4-Pyr SO₂Bu H H
1-788 3-CF_Three-Ph        4-Pyr SO₂CF_Three                   H H
1-789 3-CF_Three-Ph        4-Pyr SO₂-(CH₂)₂-F H H
1-790 3-CF_Three-Ph        4-Pyr SO₂-(CH₂)₂-OH H H
1-791 3-CF_Three-Ph        4-Pyr SO₂-(CH₂)₂-OMe H H
1-792 3-CF_Three-Ph        4-Pyr SO₂NH₂                 H H
1-793 3-CF_Three-Ph        4-Pyr SO₂NHMe H H
1-794 3-CF_Three-Ph        4-Pyr SO₂NHEt H H
1-795 3-CF_Three-Ph        4-Pyr SO₂NHPr H H
1-796 3-CF_Three-Ph        4-Pyr SO₂NH-i-Pr H H
1-797 3-CF_Three-Ph        4-Pyr SO₂NHBu H H
1-798 3-CF_Three-Ph        4-Pyr SO₂NHBn H H
1-799 3-CF_Three-Ph        4-Pyr SO₂NMe₂                H H
1-800 3-CF_Three-Ph        4-Pyr SO₂NH-c-Pr H H
1-801 3-CF_Three-Ph        4-Pyr SO₂NH-c-Bu H H
1-802 3-CF_Three-Ph        4-Pyr SO₂NH-c-Pen H H
1-803 3-CF_Three-Ph        4-Pyr SO₂NH-c-Hex H H
1-804 3-CF_Three-Ph        4-Pyr SO₂NH-c-Hep H H
1-805 3-CF_Three-Ph        4-Pyr SO₂NHCH₂-c-Pr H H
1-806 3-CF_Three-Ph        4-Pyr SO₂NH-Allyl H H
1-807 3-CF_Three-Ph        4-Pyr SO₂NH-Propargyl H H
1-808 3-CF_Three-Ph        4-Pyr SO₂NHPh H H
1-809 3-CF_Three-Ph        4-Pyr SO₂NH-3-Pyr H H
1-810 3-CF_Three-Ph        4-Pyr SO₂NHCH₂-4-Pyr H H
1-811 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-OH H H
1-812 3-CF_Three-Ph        4-Pyr SO₂NHCH (CH₂OH)₂          H H
1-813 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-OAc H H
1-814 3-CF_Three-Ph        4-Pyr SO₂NHCH₂CN H H
1-815 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-F H H
1-816 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-OMe H H
1-817 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-SMe H H
1-818 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-NH₂        H H
1-819 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-NHMe H H
1-820 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-N (Me)₂      H H
1-821 3-CF_Three-Ph        4-Pyr SO₂NHCH₂COOH H H
1-822 3-CF_Three-Ph        4-Pyr SO₂NHCH₂COOEt H H
1-823 3-CF_Three-Ph        4-Pyr SO₂NHCH (Me) COOEt H H
1-824 3-CF_Three-Ph        4-Pyr SO₂NHCH₂CONH₂           H H
1-825 3-CF_Three-Ph        4-Pyr SO₂NHOH H H
1-826 3-CF_Three-Ph        4-Pyr SO₂NHOMe H H
1-827 3-CF_Three-Ph        4-Pyr SO₂NHOEt H H
1-828 3-CF_Three-Ph        4-Pyr SO₂NHOPr H H
1-829 3-CF_Three-Ph        4-Pyr SO₂NHOAllyl H H
1-830 3-CF_Three-Ph        4-Pyr SO₂NHOBn H H
1-831 3-CF_Three-Ph        4-Pyr SO₂NHNH₂               H H
1-832 3-CF_Three-Ph        4-Pyr SO₂NHNHMe H H
1-833 3-CF_Three-Ph        4-Pyr SO₂NHN (Me)₂            H H
1-834 4-F-Ph 4-Pym CONH₂                   H H
1-835 4-F-Ph 4-Pym CONHMe H H
1-836 4-F-Ph 4-Pym CONHEt H H
1-837 4-F-Ph 4-Pym CONHPr H H
1-838 4-F-Ph 4-Pym CONH-i-Pr H H
1-839 4-F-Ph 4-Pym CONHBu H H
1-840 4-F-Ph 4-Pym CONHBn H H
1-841 4-F-Ph 4-Pym CONMe₂                  H H
1-842 4-F-Ph 4-Pym CONH-c-Pr H H
1-843 4-F-Ph 4-Pym CONH-c-Bu H H
1-844 4-F-Ph 4-Pym CONH-c-Pen H H
1-845 4-F-Ph 4-Pym CONH-c-Hex H H
1-846 4-F-Ph 4-Pym CONH-c-Hep H H
1-847 4-F-Ph 4-Pym CONHCH₂-c-Pr H H
1-848 4-F-Ph 4-Pym CONH-Allyl H H
1-849 4-F-Ph 4-Pym CONH-Propargyl H H
1-850 4-F-Ph 4-Pym CONHPh H H
1-851 4-F-Ph 4-Pym CONH-3-Pyr H H
1-852 4-F-Ph 4-Pym CONHCH₂-4-Pyr H H
1-853 4-F-Ph 4-Pym CONH- (CH₂)₂-OH H H
1-854 4-F-Ph 4-Pym CONHCH (CH₂OH)₂           H H
1-855 4-F-Ph 4-Pym CONH- (CH₂)₂-OAc H H
1-856 4-F-Ph 4-Pym CONHCH₂CN H H
1-857 4-F-Ph 4-Pym CONH- (CH₂)₂-F H H
1-858 4-F-Ph 4-Pym CONH- (CH₂)₂-OMe H H
1-859 4-F-Ph 4-Pym CONH- (CH₂)₂-SMe H H
1-860 4-F-Ph 4-Pym CONH- (CH₂)₂-NH₂          H H
1-861 4-F-Ph 4-Pym CONH- (CH₂)₂-NHMe H H
1-862 4-F-Ph 4-Pym CONH- (CH₂)₂-N (Me)₂       H H
1-863 4-F-Ph 4-Pym CONHCH₂COOH H H
1-864 4-F-Ph 4-Pym CONHCH₂COOEt H H
1-865 4-F-Ph 4-Pym CONHCH (Me) COOEt H H
1-866 4-F-Ph 4-Pym CONHCH₂CONH₂            H H
1-867 4-F-Ph 4-Pym SO₂NH₂                  H H
1-868 4-F-Ph 4-Pym SO₂NHMe H H
1-869 4-F-Ph 4-Pym SO₂NHEt H H
1-870 4-F-Ph 4-Pym SO₂NHPr H H
1-871 4-F-Ph 4-Pym SO₂NH-i-Pr H H
1-872 4-F-Ph 4-Pym SO₂NHBu H H
1-873 4-F-Ph 4-Pym SO₂NHBn H H
1-874 4-F-Ph 4-Pym SO₂NMe₂                 H H
1-875 4-F-Ph 4-Pym SO₂NH-c-Pr H H
1-876 4-F-Ph 4-Pym SO₂NH-c-Bu H H
1-877 4-F-Ph 4-Pym SO₂NH-c-Pen H H
1-878 4-F-Ph 4-Pym SO₂NH-c-Hex H H
1-879 4-F-Ph 4-Pym SO₂NH-c-Hep H H
1-880 4-F-Ph 4-Pym SO₂NHCH₂-c-Pr H H
1-881 4-F-Ph 4-Pym SO₂NH-Allyl H H
1-882 4-F-Ph 4-Pym SO₂NH-Propargyl H H
1-883 4-F-Ph 4-Pym SO₂NHPh H H
1-884 4-F-Ph 4-Pym SO₂NH-3-Pyr H H
1-885 4-F-Ph 4-Pym SO₂NHCH₂-4-Pyr H H
1-886 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OH H H
1-887 4-F-Ph 4-Pym SO₂NHCH (CH₂OH)₂          H H
1-888 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OAc H H
1-889 4-F-Ph 4-Pym SO₂NHCH₂CN H H
1-890 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-F H H
1-891 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OMe H H
1-892 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-SMe H H
1-893 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-NH₂        H H
1-894 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-NHMe H H
1-895 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-N (Me)₂      H H
1-896 4-F-Ph 4-Pym SO₂NHCH₂COOH H H
1-897 4-F-Ph 4-Pym SO₂NHCH₂COOEt H H
1-898 4-F-Ph 4-Pym SO₂NHCH (Me) COOEt H H
1-899 4-F-Ph 4-Pym SO₂NHCH₂CONH₂           H H
1-900 4-F-Ph 4-Pym SO₂NHOH H H
1-901 4-F-Ph 4-Pym SO₂NHOMe H H
1-902 4-F-Ph 4-Pym SO₂NHOEt H H
1-903 4-F-Ph 4-Pym SO₂NHOPr H H
1-904 4-F-Ph 4-Pym SO₂NHOAllyl H H
1-905 4-F-Ph 4-Pym SO₂NHOBn H H
1-906 4-F-Ph 4-Pym SO₂NHNH₂                H H
1-907 4-F-Ph 4-Pym SO₂NHNHMe H H
1-908 4-F-Ph 4-Pym SO₂NHN (Me)₂             H H
1-909 4-F-Ph 2-MeO-4-Pym CONH₂                  H H
1-910 4-F-Ph 2-MeO-4-Pym CONHMe H H
1-911 4-F-Ph 2-MeO-4-Pym CONHEt H H
1-912 4-F-Ph 2-MeO-4-Pym CONHPr H H
1-913 4-F-Ph 2-MeO-4-Pym CONH-i-Pr H H
1-914 4-F-Ph 2-MeO-4-Pym CONHBu H H
1-915 4-F-Ph 2-MeO-4-Pym CONHBn H H
1-916 4-F-Ph 2-MeO-4-Pym CONMe₂                 H H
1-917 4-F-Ph 2-MeO-4-Pym CONH-c-Pr H H
1-918 4-F-Ph 2-MeO-4-Pym CONH-c-Bu H H
1-919 4-F-Ph 2-MeO-4-Pym CONH-c-Pen H H
1-920 4-F-Ph 2-MeO-4-Pym CONH-c-Hex H H
1-921 4-F-Ph 2-MeO-4-Pym CONH-c-Hep H H
1-922 4-F-Ph 2-MeO-4-Pym CONHCH₂-c-Pr H H
1-923 4-F-Ph 2-MeO-4-Pym CONH-Allyl H H
1-924 4-F-Ph 2-MeO-4-Pym CONH-Propargyl H H
1-925 4-F-Ph 2-MeO-4-Pym CONHPh H H
1-926 4-F-Ph 2-MeO-4-Pym CONH-3-Pyr H H
1-927 4-F-Ph 2-MeO-4-Pym CONHCH₂-4-Pyr H H
1-928 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OH H H
1-929 4-F-Ph 2-MeO-4-Pym CONHCH (CH₂OH)₂           H H
1-930 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OAc H H
1-931 4-F-Ph 2-MeO-4-Pym CONHCH₂CN                H H
1-932 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-F H H
1-933 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OMe H H
1-934 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-SMe H H
1-935 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-NH₂          H H
1-936 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-NHMe H H
1-937 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-N (Me)₂       H H
1-938 4-F-Ph 2-MeO-4-Pym CONHCH₂COOH              H H
1-939 4-F-Ph 2-MeO-4-Pym CONHCH₂COOEt             H H
1-940 4-F-Ph 2-MeO-4-Pym CONHCH (Me) COOEt H H
1-941 4-F-Ph 2-MeO-4-Pym CONHCH₂CONH₂            H H
1-942 4-F-Ph 2-MeO-4-Pym SO₂NH₂                  H H
1-943 4-F-Ph 2-MeO-4-Pym SO₂NHMe                 H H
1-944 4-F-Ph 2-MeO-4-Pym SO₂NHEt                 H H
1-945 4-F-Ph 2-MeO-4-Pym SO₂NHPr                 H H
1-946 4-F-Ph 2-MeO-4-Pym SO₂NH-i-Pr              H H
1-947 4-F-Ph 2-MeO-4-Pym SO₂NHBu                 H H
1-948 4-F-Ph 2-MeO-4-Pym SO₂NHBn                 H H
1-949 4-F-Ph 2-MeO-4-Pym SO₂NMe₂                 H H
1-950 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Pr              H H
1-951 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Bu H H
1-952 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Pen H H
1-953 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Hex H H
1-954 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Hep H H
1-955 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂-c-Pr H H
1-956 4-F-Ph 2-MeO-4-Pym SO₂NH-Allyl             H H
1-957 4-F-Ph 2-MeO-4-Pym SO₂NH-Propargyl         H H
1-958 4-F-Ph 2-MeO-4-Pym SO₂NHPh                 H H
1-959 4-F-Ph 2-MeO-4-Pym SO₂NH-3-Pyr             H H
1-960 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂-4-Pyr H H
1-961 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OH H H
1-962 4-F-Ph 2-MeO-4-Pym SO₂NHCH (CH₂OH)₂         H H
1-963 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OAc H H
1-964 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂CN               H H
1-965 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-F H H
1-966 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OMe H H
1-967 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-SMe H H
1-968 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-NH₂         H H
1-969 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-NHMe H H
1-970 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-N (Me)₂      H H
1-971 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂COOH H H
1-972 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂COOEt H H
1-973 4-F-Ph 2-MeO-4-Pym SO₂NHCH (Me) COOEt        H H
1-974 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂CONH₂           H H
1-975 4-F-Ph 2-MeO-4-Pym SO₂NHOH                 H H
1-976 4-F-Ph 2-MeO-4-Pym SO₂NHOMe H H
1-977 4-F-Ph 2-MeO-4-Pym SO₂NHOEt H H
1-978 4-F-Ph 2-MeO-4-Pym SO₂NHOPr H H
1-979 4-F-Ph 2-MeO-4-Pym SO₂NHOAllyl H H
1-980 4-F-Ph 2-MeO-4-Pym SO₂NHOBn H H
1-981 4-F-Ph 2-MeO-4-Pym SO₂NHNH₂                H H
1-982 4-F-Ph 2-MeO-4-Pym SO₂NHNHMe H H
1-983 4-F-Ph 2-MeO-4-Pym SO₂NHN (Me)₂             H H
1-984 4-F-Ph 2-NH₂-4-Pym CONH₂                  H H
1-985 4-F-Ph 2-NH₂-4-Pym       CONHMe H H
1-986 4-F-Ph 2-NH₂-4-Pym CONHEt H H
1-987 4-F-Ph 2-NH₂-4-Pym CONHPr H H
1-988 4-F-Ph 2-NH₂-4-Pym CONH-i-Pr H H
1-989 4-F-Ph 2-NH₂-4-Pym CONHBu H H
1-990 4-F-Ph 2-NH₂-4-Pym CONHBn H H
1-991 4-F-Ph 2-NH₂-4-Pym CONMe₂                 H H
1-992 4-F-Ph 2-NH₂-4-Pym CONH-c-Pr H H
1-993 4-F-Ph 2-NH₂-4-Pym CONH-c-Bu H H
1-994 4-F-Ph 2-NH₂-4-Pym CONH-c-Pen H H
1-995 4-F-Ph 2-NH₂-4-Pym CONH-c-Hex H H
1-996 4-F-Ph 2-NH₂-4-Pym CONH-c-Hep H H
1-997 4-F-Ph 2-NH₂-4-Pym CONHCH₂-c-Pr H H
1-998 4-F-Ph 2-NH₂-4-Pym CONH-Allyl H H
1-999 4-F-Ph 2-NH₂-4-Pym CONH-Propargyl H H
1-1000 4-F-Ph 2-NH₂-4-Pym CONHPh H H
1-1001 4-F-Ph 2-NH₂-4-Pym CONH-3-Pyr H H
1-1002 4-F-Ph 2-NH₂-4-Pym CONHCH₂-4-Pyr H H
1-1003 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OH H H
1-1004 4-F-Ph 2-NH₂-4-Pym CONHCH (CH₂OH)₂           H H
1-1005 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OAc H H
1-1006 4-F-Ph 2-NH₂-4-Pym CONHCH₂CN H H
1-1007 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-F H H
1-1008 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OMe H H
1-1009 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-SMe H H
1-1010 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-NH₂          H H
1-1011 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-NHMe H H
1-1012 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-N (Me)₂       H H
1-1013 4-F-Ph 2-NH₂-4-Pym CONHCH₂COOH H H
1-1014 4-F-Ph 2-NH₂-4-Pym CONHCH₂COOEt H H
1-1015 4-F-Ph 2-NH₂-4-Pym CONHCH (Me) COOEt         H H
1-1016 4-F-Ph 2-NH₂-4-Pym CONHCH₂CONH₂           H H
1-1017 4-F-Ph 2-NH₂-4-Pym SO₂NH₂                 H H
1-1018 4-F-Ph 2-NH₂-4-Pym SO₂NHMe H H
1-1019 4-F-Ph 2-NH₂-4-Pym SO₂NHEt H H
1-1020 4-F-Ph 2-NH₂-4-Pym SO₂NHPr H H
1-1021 4-F-Ph 2-NH₂-4-Pym SO₂NH-i-Pr H H
1-1022 4-F-Ph 2-NH₂-4-Pym SO₂NHBu H H
1-1023 4-F-Ph 2-NH₂-4-Pym SO₂NHBn H H
1-1024 4-F-Ph 2-NH₂-4-Pym SO₂NMe₂                H H
1-1025 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Pr H H
1-1026 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Bu H H
1-1027 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Pen H H
1-1028 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Hex H H
1-1029 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Hep H H
1-1030 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂-c-Pr H H
1-1031 4-F-Ph 2-NH₂-4-Pym SO₂NH-Allyl H H
1-1032 4-F-Ph 2-NH₂-4-Pym SO₂NH-Propargyl H H
1-1033 4-F-Ph 2-NH₂-4-Pym SO₂NHPh H H
1-1034 4-F-Ph 2-NH₂-4-Pym SO₂NH-3-Pyr H H
1-1035 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂-4-Pyr H H
1-1036 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OH H H
1-1037 4-F-Ph 2-NH₂-4-Pym SO₂NHCH (CH₂OH)₂        H H
1-1038 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OAc H H
1-1039 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂CN H H
1-1040 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-F H H
1-1041 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OMe H H
1-1042 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-SMe H H
1-1043 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-NH₂        H H
1-1044 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-NHMe H H
1-1045 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-N (Me)₂      H H
1-1046 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂COOH H H
1-1047 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂COOEt H H
1-1048 4-F-Ph 2-NH₂-4-Pym SO₂NHCH (Me) COOEt H H
1-1049 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂CONH₂           H H
1-1050 4-F-Ph 2-NH₂-4-Pym SO₂NHOH H H
1-1051 4-F-Ph 2-NH₂-4-Pym SO₂NHOMe H H
1-1052 4-F-Ph 2-NH₂-4-Pym SO₂NHOEt H H
1-1053 4-F-Ph 2-NH₂-4-Pym SO₂NHOPr H H
1-1054 4-F-Ph 2-NH₂-4-Pym SO₂NHOAllyl H H
1-1055 4-F-Ph 2-NH₂-4-Pym SO₂NHOBn H H
1-1056 4-F-Ph 2-NH₂-4-Pym SO₂NHNH₂               H H
1-1057 4-F-Ph 2-NH₂-4-Pym SO₂NHNHMe               H H
1-1058 4-F-Ph 2-NH₂-4-Pym SO₂NHN (Me)₂            H H
1-1059 4-F-Ph 2-MeNH-4-Pym CONH₂                  H H
1-1060 4-F-Ph 2-MeNH-4-Pym CONHMe H H
1-1061 4-F-Ph 2-MeNH-4-Pym CONHEt H H
1-1062 4-F-Ph 2-MeNH-4-Pym CONHPr H H
1-1063 4-F-Ph 2-MeNH-4-Pym CONH-i-Pr H H
1-1064 4-F-Ph 2-MeNH-4-Pym CONHBu H H
1-1065 4-F-Ph 2-MeNH-4-Pym CONHBn H H
1-1066 4-F-Ph 2-MeNH-4-Pym CONMe₂                  H H
1-1067 4-F-Ph 2-MeNH-4-Pym CONH-c-Pr H H
1-1068 4-F-Ph 2-MeNH-4-Pym CONH-c-Bu H H
1-1069 4-F-Ph 2-MeNH-4-Pym CONH-c-Pen H H
1-1070 4-F-Ph 2-MeNH-4-Pym CONH-c-Hex H H
1-1071 4-F-Ph 2-MeNH-4-Pym CONH-c-Hep H H
1-1072 4-F-Ph 2-MeNH-4-Pym CONHCH₂-c-Pr H H
1-1073 4-F-Ph 2-MeNH-4-Pym CONH-Allyl H H
1-1074 4-F-Ph 2-MeNH-4-Pym CONH-Propargyl H H
1-1075 4-F-Ph 2-MeNH-4-Pym CONHPh H H
1-1076 4-F-Ph 2-MeNH-4-Pym CONH-3-Pyr H H
1-1077 4-F-Ph 2-MeNH-4-Pym CONHCH₂-4-Pyr H H
1-1078 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OH H H
1-1079 4-F-Ph 2-MeNH-4-Pym CONHCH (CH₂OH)₂           H H
1-1080 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OAc H H
1-1081 4-F-Ph 2-MeNH-4-Pym CONHCH₂CN H H
1-1082 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-F H H
1-1083 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OMe H H
1-1084 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-SMe H H
1-1085 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-NH₂          H H
1-1086 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-NHMe H H
1-1087 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-N (Me)₂       H H
1-1088 4-F-Ph 2-MeNH-4-Pym CONHCH₂COOH H H
1-1089 4-F-Ph 2-MeNH-4-Pym CONHCH₂COOEt H H
1-1090 4-F-Ph 2-MeNH-4-Pym CONHCH (Me) COOEt H H
1-1091 4-F-Ph 2-MeNH-4-Pym CONHCH₂CONH₂            H H
1-1092 4-F-Ph 2-MeNH-4-Pym SO₂NH₂                  H H
1-1093 4-F-Ph 2-MeNH-4-Pym SO₂NHMe H H
1-1094 4-F-Ph 2-MeNH-4-Pym SO₂NHEt H H
1-1095 4-F-Ph 2-MeNH-4-Pym SO₂NHPr H H
1-1096 4-F-Ph 2-MeNH-4-Pym SO₂NH-i-Pr H H
1-1097 4-F-Ph 2-MeNH-4-Pym SO₂NHBu H H
1-1098 4-F-Ph 2-MeNH-4-Pym SO₂NHBn H H
1-1099 4-F-Ph 2-MeNH-4-Pym SO₂NMe₂                 H H
1-1100 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Pr H H
1-1101 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Bu H H
1-1102 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Pen H H
1-1103 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Hex H H
1-1104 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Hep H H
1-1105 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂-c-Pr            H H
1-1106 4-F-Ph 2-MeNH-4-Pym SO₂NH-Allyl H H
1-1107 4-F-Ph 2-MeNH-4-Pym SO₂NH-Propargyl H H
1-1108 4-F-Ph 2-MeNH-4-Pym SO₂NHPh H H
1-1109 4-F-Ph 2-MeNH-4-Pym SO₂NH-3-Pyr H H
1-1110 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂-4-Pyr H H
1-1111 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OH          H H
1-1112 4-F-Ph 2-MeNH-4-Pym SO₂NHCH (CH₂OH)₂         H H
1-1113 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OAc         H H
1-1114 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂CN               H H
1-1115 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-F           H H
1-1116 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OMe         H H
1-1117 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-SMe         H H
1-1118 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-NH₂         H H
1-1119 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-NHMe        H H
1-1120 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-N (Me)₂      H H
1-1121 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂COOH             H H
1-1122 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂COOEt            H H
1-1123 4-F-Ph 2-MeNH-4-Pym SO₂NHCH (Me) COOEt        H H
1-1124 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂CONH₂           H H
1-1125 4-F-Ph 2-MeNH-4-Pym SO₂NHOH H H
1-1126 4-F-Ph 2-MeNH-4-Pym SO₂NHOMe H H
1-1127 4-F-Ph 2-MeNH-4-Pym SO₂NHOEt H H
1-1128 4-F-Ph 2-MeNH-4-Pym SO₂NHOPr H H
1-1129 4-F-Ph 2-MeNH-4-Pym SO₂NHOAllyl H H
1-1130 4-F-Ph 2-MeNH-4-Pym SO₂NHOBn H H
1-1131 4-F-Ph 2-MeNH-4-Pym SO₂NHNH₂                H H
1-1132 4-F-Ph 2-MeNH-4-Pym SO₂NHNHMe H H
1-1133 4-F-Ph 2-MeNH-4-Pym SO₂NHN (Me)₂             H H
1-1134 4-F-Ph 2-BnNH-4-Pym CONH₂                   H H
1-1135 4-F-Ph 2-BnNH-4-Pym CONHMe H H
1-1136 4-F-Ph 2-BnNH-4-Pym CONHEt H H
1-1137 4-F-Ph 2-BnNH-4-Pym CONHPr H H
1-1138 4-F-Ph 2-BnNH-4-Pym CONH-i-Pr H H
1-1139 4-F-Ph 2-BnNH-4-Pym CONHBu H H
1-1140 4-F-Ph 2-BnNH-4-Pym CONHBn H H
1-1141 4-F-Ph 2-BnNH-4-Pym CONMe₂                 H H
1-1142 4-F-Ph 2-BnNH-4-Pym CONH-c-Pr H H
1-1143 4-F-Ph 2-BnNH-4-Pym CONH-c-Bu H H
1-1144 4-F-Ph 2-BnNH-4-Pym CONH-c-Pen H H
1-1145 4-F-Ph 2-BnNH-4-Pym CONH-c-Hex H H
1-1146 4-F-Ph 2-BnNH-4-Pym CONH-c-Hep H H
1-1147 4-F-Ph 2-BnNH-4-Pym CONHCH₂-c-Pr H H
1-1148 4-F-Ph 2-BnNH-4-Pym CONH-Allyl H H
1-1149 4-F-Ph 2-BnNH-4-Pym CONH-Propargyl H H
1-1150 4-F-Ph 2-BnNH-4-Pym CONHPh H H
1-1151 4-F-Ph 2-BnNH-4-Pym CONH-3-Pyr H H
1-1152 4-F-Ph 2-BnNH-4-Pym CONHCH₂-4-Pyr H H
1-1153 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OH H H
1-1154 4-F-Ph 2-BnNH-4-Pym CONHCH (CH₂OH)₂           H H
1-1155 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OAc H H
1-1156 4-F-Ph 2-BnNH-4-Pym CONHCH₂CN                H H
1-1157 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-F H H
1-1158 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OMe H H
1-1159 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-SMe H H
1-1160 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-NH₂          H H
1-1161 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-NHMe H H
1-1162 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-N (Me)₂      H H
1-1163 4-F-Ph 2-BnNH-4-Pym CONHCH₂COOH              H H
1-1164 4-F-Ph 2-BnNH-4-Pym CONHCH₂COOEt             H H
1-1165 4-F-Ph 2-BnNH-4-Pym CONHCH (Me) COOEt H H
1-1166 4-F-Ph 2-BnNH-4-Pym CONHCH₂CONH₂            H H
1-1167 4-F-Ph 2-BnNH-4-Pym SO₂NH₂                  H H
1-1168 4-F-Ph 2-BnNH-4-Pym SO₂NHMe H H
1-1169 4-F-Ph 2-BnNH-4-Pym SO₂NHEt H H
1-1170 4-F-Ph 2-BnNH-4-Pym SO₂NHPr H H
1-1171 4-F-Ph 2-BnNH-4-Pym SO₂NH-i-Pr H H
1-1172 4-F-Ph 2-BnNH-4-Pym SO₂NHBu H H
1-1173 4-F-Ph 2-BnNH-4-Pym SO₂NHBn H H
1-1174 4-F-Ph 2-BnNH-4-Pym SO₂NMe₂                H H
1-1175 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Pr H H
1-1176 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Bu H H
1-1177 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Pen H H
1-1178 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Hex H H
1-1179 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Hep H H
1-1180 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂-c-Pr H H
1-1181 4-F-Ph 2-BnNH-4-Pym SO₂NH-Allyl H H
1-1182 4-F-Ph 2-BnNH-4-Pym SO₂NH-Propargyl H H
1-1183 4-F-Ph 2-BnNH-4-Pym SO₂NHPh H H
1-1184 4-F-Ph 2-BnNH-4-Pym SO₂NH-3-Pyr H H
1-1185 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂-4-Pyr H H
1-1186 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OH H H
1-1187 4-F-Ph 2-BnNH-4-Pym SO₂NHCH (CH₂OH)₂          H H
1-1188 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OAc H H
1-1189 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂CN H H
1-1190 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-F H H
1-1191 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OMe H H
1-1192 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-SMe H H
1-1193 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-NH₂          H H
1-1194 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-NHMe H H
1-1195 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-N (Me)₂      H H
1-1196 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂COOH             H H
1-1197 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂COOEt H H
1-1198 4-F-Ph 2-BnNH-4-Pym SO₂NHCH (Me) COOEt        H H
1-1199 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂CONH₂           H H
1-1200 4-F-Ph 2-BnNH-4-Pym SO₂NHOH H H
1-1201 4-F-Ph 2-BnNH-4-Pym SO₂NHOMe H H
1-1202 4-F-Ph 2-BnNH-4-Pym SO₂NHOEt H H
1-1203 4-F-Ph 2-BnNH-4-Pym SO₂NHOPr H H
1-1204 4-F-Ph 2-BnNH-4-Pym SO₂NHOAllyl H H
1-1205 4-F-Ph 2-BnNH-4-Pym SO₂NHOBn H H
1-1206 4-F-Ph 2-BnNH-4-Pym SO₂NHNH₂                 H H
1-1207 4-F-Ph 2-BnNH-4-Pym SO₂NHNHMe H H
1-1208 4-F-Ph 2-BnNH-4-Pym SO₂NHN (Me)₂             H H
1-1209 4-F-Ph (α-Me-BnNH) -4-Pym CONH₂                  H H
1-1210 4-F-Ph (α-Me-BnNH) -4-Pym CONHMe H H
1-1211 4-F-Ph (α-Me-BnNH) -4-Pym CONHEt H H
1-1212 4-F-Ph (α-Me-BnNH) -4-Pym CONHPr H H
1-1213 4-F-Ph (α-Me-BnNH) -4-Pym CONH-i-Pr H H
1-1214 4-F-Ph (α-Me-BnNH) -4-Pym CONHBu H H
1-1215 4-F-Ph (α-Me-BnNH) -4-Pym CONHBn H H
1-1216 4-F-Ph (α-Me-BnNH) -4-Pym CONMe₂                 H H
1-1217 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Pr H H
1-1218 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Bu H H
1-1219 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Pen H H
1-1220 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Hex H H
1-1221 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Hep H H
1-1222 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂-c-Pr H H
1-1223 4-F-Ph (α-Me-BnNH) -4-Pym CONH-Allyl H H
1-1224 4-F-Ph (α-Me-BnNH) -4-Pym CONH-Propargyl H H
1-1225 4-F-Ph (α-Me-BnNH) -4-Pym CONHPh H H
1-1226 4-F-Ph (α-Me-BnNH) -4-Pym CONH-3-Pyr H H
1-1227 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂-4-Pyr            H H
1-1228 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OH H H
1-1229 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH (CH₂OH)₂           H H
1-1230 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OAc H H
1-1231 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂CN                H H
1-1232 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-F H H
1-1233 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OMe H H
1-1234 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-SMe H H
1-1235 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-NH₂          H H
1-1236 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-NHMe H H
1-1237 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-N (Me)₂      H H
1-1238 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂COOH H H
1-1239 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂COOEt H H
1-1240 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH (Me) COOEt H H
1-1241 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂CONH₂            H H
1-1242 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH₂                  H H
1-1243 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHMe H H
1-1244 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHEt H H
1-1245 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHPr H H
1-1246 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-i-Pr H H
1-1247 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHBu H H
1-1248 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHBn H H
1-1249 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NMe₂                H H
1-1250 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Pr H H
1-1251 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Bu H H
1-1252 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Pen H H
1-1253 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Hex H H
1-1254 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Hep H H
1-1255 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂-c-Pr H H
1-1256 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-Allyl H H
1-1257 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-Propargyl H H
1-1258 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHPh H H
1-1259 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-3-Pyr H H
1-1260 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂-4-Pyr H H
1-1261 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OH H H
1-1262 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH (CH₂OH)₂          H H
1-1263 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OAc H H
1-1264 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂CN H H
1-1265 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-F H H
1-1266 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OMe H H
1-1267 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-SMe H H
1-1268 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-NH₂        H H
1-1269 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-NHMe H H
1-1270 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-N (Me)₂      H H
1-1271 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂COOH H H
1-1272 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂COOEt H H
1-1273 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH (Me) COOEt H H
1-1274 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂CONH₂           H H
1-1275 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOH H H
1-1276 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOMe H H
1-1277 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOEt H H
1-1278 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOPr H H
1-1279 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOAllyl H H
1-1280 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOBn H H
1-1281 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHNH₂               H H
1-1282 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHNHMe              H H
1-1283 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHN (Me)₂            H H
1-1284 4-F-Ph 4-Pyr SO₂NHMe                 OH H
1-1285 4-F-Ph 4-Pyr SO₂NHMe                 Me H
1-1286 4-F-Ph 4-Pyr SO₂NHMe                 Et H
1-1287 4-F-Ph 4-Pyr SO₂NHMe                 F H
1-1288 4-F-Ph 4-Pyr SO₂NHMe                 OMe H
1-1289 4-F-Ph 4-Pyr SO₂NHMe OEt H
1-1290 4-F-Ph 4-Pyr SO₂NHMe                  = O
1-1291 4-F-Ph 4-Pyr SO₂NHMe                  = CH₂
1-1292 4-F-Ph 4-Pyr SO₂NHMe                 -CH₂CH₂-
1-1293 4-F-Ph 4-Pyr SOMe                    OH H
1-1294 4-F-Ph 4-Pyr SOMe                    Me H
1-1295 4-F-Ph 4-Pyr SOMe                    Et H
1-1296 4-F-Ph 4-Pyr SOMe                    F H
1-1297 4-F-Ph 4-Pyr SOMe                    OMe H
1-1298 4-F-Ph 4-Pyr SOMe                    OEt H
1-1299 4-F-Ph 4-Pyr SOMe                      = O
1-1300 4-F-Ph 4-Pyr SOMe = CH₂
1-1301 4-F-Ph 4-Pyr SOMe                     -CH₂CH₂-
1-1302 4-F-Ph 4-Pyr SO₂Me                   OH H
1-1303 4-F-Ph 4-Pyr SO₂Me                   Me H
1-1304 4-F-Ph 4-Pyr SO₂Me                   Et H
1-1305 4-F-Ph 4-Pyr SO₂Me                   F H
1-1306 4-F-Ph 4-Pyr SO₂Me                   OMe H
1-1307 4-F-Ph 4-Pyr SO₂Me                   OEt H
1-1308 4-F-Ph 4-Pyr SO₂Me                      = O
1-1309 4-F-Ph 4-Pyr SO₂Me                      = CH₂
1-1310 4-F-Ph 4-Pyr SO₂Me                     -CH₂CH₂-
1-1311 3-Cl-4-F-Ph 4-Pyr SO₂NHMe                  OH H
1-1312 3-Cl-4-F-Ph 4-Pyr SO₂NHMe                  Me H
1-1313 3-Cl-4-F-Ph 4-Pyr SO₂NHMe                  Et H
1-1314 3-Cl-4-F-Ph 4-Pyr SO₂NHMe                  F H
1-1315 3-Cl-4-F-Ph 4-Pyr SO₂NHMe OMe H
1-1316 3-Cl-4-F-Ph 4-Pyr SO₂NHMe OEt H
1-1317 3-Cl-4-F-Ph 4-Pyr SO₂NHMe = O
1-1318 3-Cl-4-F-Ph 4-Pyr SO₂NHMe                    = CH₂
1-1319 3-Cl-4-F-Ph 4-Pyr SO₂NHMe                   -CH₂CH₂-
1-1320 3-Cl-4-F-Ph 4-Pyr SOMe                     OH H
1-1321 3-Cl-4-F-Ph 4-Pyr SOMe                     Me H
1-1322 3-Cl-4-F-Ph 4-Pyr SOMe                     Et H
1-1323 3-Cl-4-F-Ph 4-Pyr SOMe                     F H
1-1324 3-Cl-4-F-Ph 4-Pyr SOMe                     OMe H
1-1325 3-Cl-4-F-Ph 4-Pyr SOMe                     OEt H
1-1326 3-Cl-4-F-Ph 4-Pyr SOMe                       = O
1-1327 3-Cl-4-F-Ph 4-Pyr SOMe                       = CH₂
1-1328 3-Cl-4-F-Ph 4-Pyr SOMe                     -CH₂CH₂-
1-1329 3-Cl-4-F-Ph 4-Pyr SO₂Me OH H
1-1330 3-Cl-4-F-Ph 4-Pyr SO₂Me Me H
1-1331 3-Cl-4-F-Ph 4-Pyr SO₂Me Et H
1-1332 3-Cl-4-F-Ph 4-Pyr SO₂Me F H
1-1333 3-Cl-4-F-Ph 4-Pyr SO₂Me OMe H
1-1334 3-Cl-4-F-Ph 4-Pyr SO₂Me OEt H
1-1335 3-Cl-4-F-Ph 4-Pyr SO₂Me = O
1-1336 3-Cl-4-F-Ph 4-Pyr SO₂Me = CH₂
1-1337 3-Cl-4-F-Ph 4-Pyr SO₂Me -CH₂CH₂-
1-1338 4-F-Ph 4-Pyr COO (CH₂)₂N (Me)₂           H H
1-1339 4-F-Ph 4-Pyr SO₂NHOCH₂CH (OH) CH₂OH H H
1-1340 4-F-Ph 4-Pyr CONHOCH₂CH (OH) CH₂OH H H
1-1341 4-F-Ph 4-Pyr SO₂CH₂CH₂OMe H H
1-1342 4-F-Ph 4-Pyr SO₂CH₂CH₂OH H H
1-1343 4-F-Ph 4-Pyr SO₂CH₂CH (OH) CH₂OH H H
1-1344 3-Cl-4-F-Ph 4-Pyr SO₂NHOCH₂CH (OH) CH₂OH H H
1-1345 3-Cl-4-F-Ph 4-Pyr CONHOCH₂CH (OH) CH₂OH H H
1-1346 3-Cl-4-F-Ph 4-Pyr SO₂CH₂CH₂OMe H H
1-1347 3-Cl-4-F-Ph 4-Pyr SO₂CH₂CH₂OH H H
1-1348 3-Cl-4-F-Ph 4-Pyr SO₂CH₂CH (OH) CH₂OH H H
―――――――――――――――――――――――――――――――――――
Table 2

―――――――――――――――――――――――――――――――――――
Compound R ¹ R ⁴ R ^{4 '} R ⁵ R ⁶ R ⁷ l
No .――――――――――――――――――――――――――――――――――――
2-1 4-F-Ph HH SO ₂ NHMe 3-FH 2
2-2 4-F-Ph HH SO ₂ NHMe 3-Cl H 2
2-3 4-F-Ph HH SO ₂ NHMe 3-OMe H 2
2-4 4-F-Ph HH SO ₂ NHMe 3-Me H 2
2-5 4-F-Ph Me H SO ₂ NHMe HH 2
2-6 4-F-Ph H Me SO ₂ NHMe HH 2
2-7 4-F-Ph Me Me SO ₂ NHMe HH 2
2-8 4-F-Ph HH SO ₂ NHMe H 3-Me 2
2-9 4-F-Ph HH SO ₂ NHMe H 2-Me 2
2-10 4-F-Ph HH SO ₂ NHMe H 2-Et 2
2-11 4-F-Ph HH SO ₂ Me 3-FH 2
2-12 4-F-Ph HH SO ₂ Me 3-Cl H 2
2-13 4-F-Ph HH SO ₂ Me 3-OMe H 2
2-14 4-F-Ph HH SO ₂ Me 3-Me H 2
2-15 4-F-Ph Me H SO ₂ Me HH 2
2-16 4-F-Ph H Me SO ₂ Me HH 2
2-17 4-F-Ph Me Me SO ₂ Me HH 2
2-18 4-F-Ph HH SO ₂ Me H 3-Me 2
2-19 4-F-Ph HH SO ₂ Me H 2-Me 2
2-20 4-F-Ph HH SO ₂ Me H 2-Et 2
2-21 3-Cl-4-F-Ph HH SO ₂ NHMe 3-FH 2
2-22 3-Cl-4-F-Ph HH SO ₂ NHMe 3-Cl H 2
2-23 3-Cl-4-F-Ph HH SO ₂ NHMe 3-OMe H 2
2-24 3-Cl-4-F-Ph HH SO ₂ NHMe 3-Me H 2
2-25 3-Cl-4-F-Ph Me H SO ₂ NHMe HH 2
2-26 3-Cl-4-F-Ph H Me SO ₂ NHMe HH 2
2-27 3-Cl-4-F-Ph Me Me SO ₂ NHMe HH 2
2-28 3-Cl-4-F-Ph HH SO ₂ NHMe H 3-Me 2
2-29 3-Cl-4-F-Ph HH SO ₂ NHMe H 2-Me 2
2-30 3-Cl-4-F-Ph HH SO ₂ NHMe H 2-Et 2
2-31 3-Cl-4-F-Ph HH SO ₂ Me 3-FH 2
2-32 3-Cl-4-F-Ph HH SO ₂ Me 3-Cl H 2
2-33 3-Cl-4-F-Ph HH SO ₂ Me 3-OMe H 2
2-34 3-Cl-4-F-Ph HH SO ₂ Me 3-Me H 2
2-35 3-Cl-4-F-Ph Me H SO ₂ Me HH 2
2-36 3-Cl-4-F-Ph H Me SO ₂ Me HH 2
2-37 3-Cl-4-F-Ph Me Me SO ₂ Me HH 2
2-38 3-Cl-4-F-Ph HH SO ₂ Me H 3-Me 2
2-39 3-Cl-4-F-Ph HH SO ₂ Me H 2-Me 2
2-40 3-Cl-4-F-Ph HH SO ₂ Me H 2-Et 2
2-41 4-F-Ph HH SO ₂ NHMe HH 1
2-42 4-F-Ph HH SO ₂ NHMe HH 3
2-43 4-F-Ph HH CONHMe HH 4
2-44 4-F-Ph HH SO ₂ Me HH 5
―――――――――――――――――――――――――――――――――――
Table 3

――――――――――――――――――――
Compound R ¹ R ⁵
No .――――――――――――――――――――
3-1 4-F-Ph 2-COOH
3-2 4-F-Ph 3-COOH
3-3 4-F-Ph 2-CONH ₂
3-4 4-F-Ph 3-CONH ₂
3-5 4-F-Ph 3-CONHMe
3-6 4-F-Ph 3-CONHEt
3-7 4-F-Ph 3-CONHPr
3-8 4-F-Ph 3-CONH-i-Pr
3-9 4-F-Ph 2-SO ₂ NH ₂
3-10 4-F-Ph 3-SO ₂ NH ₂
3-11 4-F-Ph 3-SO ₂ NHMe
3-12 4-F-Ph 3-SO ₂ NHEt
3-13 4-F-Ph 3-SO ₂ NHPr
3-14 4-F-Ph 3-SO ₂ NH-i-Pr
3-15 4-F-Ph 2-SOMe
3-16 4-F-Ph 3-SOMe
3-17 4-F-Ph 2-SO ₂ Me
3-18 4-F-Ph 3-SO ₂ Me
3-19 3-Cl-4-F-Ph 2-COOH
3-20 3-Cl-4-F-Ph 3-COOH
3-21 3-Cl-4-F-Ph 2-CONH ₂
3-22 3-Cl-4-F-Ph 3-CONH ₂
3-23 3-Cl-4-F-Ph 3-CONHMe
3-24 3-Cl-4-F-Ph 3-CONHEt
3-25 3-Cl-4-F-Ph 3-CONHPr
3-26 3-Cl-4-F-Ph 3-CONH-i-Pr
3-27 3-Cl-4-F-Ph 2-SO ₂ NH ₂
3-28 3-Cl-4-F-Ph 3-SO ₂ NH ₂
3-29 3-Cl-4-F-Ph 3-SO ₂ NHMe
2-30 3-Cl-4-F-Ph 3-SO ₂ NHEt
3-31 3-Cl-4-F-Ph 3-SO ₂ NHPr
3-32 3-Cl-4-F-Ph 3-SO ₂ NH-i-Pr
3-33 3-Cl-4-F-Ph 2-SOMe
3-34 3-Cl-4-F-Ph 3-SOMe
3-35 3-Cl-4-F-Ph 2-SO ₂ Me
3-36 3-Cl-4-F-Ph 3-SO ₂ Me
3-37 3-Me-Ph 4-CONH ₂
3-38 3-Me-Ph 4-CONHMe
3-39 3-Me-Ph 4-CONHEt
3-40 3-Me-Ph 4-CONHPr
3-41 3-Me-Ph 4-CONH-i-Pr
3-42 3-Me-Ph 4-SO ₂ NH ₂
3-43 3-Me-Ph 4-SO ₂ NHMe
3-44 3-Me-Ph 4-SO ₂ NHEt
3-45 3-Me-Ph 4-SO ₂ NHPr
3-46 3-Me-Ph 4-SO ₂ NH-i-Pr
3-47 3-Me-Ph 4-SOMe
3-48 3-Me-Ph 4-SO ₂ Me
3-49 3-Me-Ph 4-SO ₂ CH ₂ CH ₂ OH
3-50 3-Me-Ph 4-SO ₂ CH ₂ CH ₂ OMe
――――――――――――――――――――
Table 4

―――――――――――――――――――――
Compound R ¹ R ⁵ m
No .――――――――――――――――――――――
4-1 4-F-Ph CONH ₂ 0
4-2 4-F-Ph CONHMe 0
4-3 4-F-Ph CONHEt 0
4-4 4-F-Ph CONHPr 0
4-5 4-F-Ph CONH-i-Pr 0
4-6 4-F-Ph CONHBu 0
4-7 4-F-Ph SO ₂ NH ₂ 0
4-8 4-F-Ph SO ₂ NHMe 0
4-9 4-F-Ph SO ₂ NHEt 0
4-10 4-F-Ph SO ₂ NHPr 0
4-11 4-F-Ph SO ₂ NH-i-Pr 0
4-12 4-F-Ph SO ₂ NHBu 0
4-13 4-F-Ph SOMe 0
4-14 4-F-Ph SOEt 0
4-15 4-F-Ph SOPr 0
4-16 4-F-Ph SO ₂ Me 0
4-17 4-F-Ph SO ₂ Et 0
4-18 4-F-Ph SO ₂ Pr 0
4-19 4-F-Ph COMe 0
4-20 4-F-Ph COEt 0
4-21 4-F-Ph COPr 0
4-22 3-Cl-4-F-Ph CONH ₂ 0
4-23 3-Cl-4-F-Ph CONHMe 0
4-24 3-Cl-4-F-Ph CONHEt 0
4-25 3-Cl-4-F-Ph CONHPr 0
4-26 3-Cl-4-F-Ph CONH-i-Pr 0
4-27 3-Cl-4-F-Ph CONHBu 0
4-28 3-Cl-4-F-Ph SO ₂ NH ₂ 0
4-29 3-Cl-4-F-Ph SO ₂ NHMe 0
4-30 3-Cl-4-F-Ph SO ₂ NHEt 0
4-31 3-Cl-4-F-Ph SO ₂ NHPr 0
4-32 3-Cl-4-F-Ph SO ₂ NH-i-Pr 0
4-33 3-Cl-4-F-Ph SO ₂ NHBu 0
4-34 3-Cl-4-F-Ph SOMe 0
4-35 3-Cl-4-F-Ph SOEt 0
4-36 3-Cl-4-F-Ph SOPr 0
4-37 3-Cl-4-F-Ph SO ₂ Me 0
4-38 3-Cl-4-F-Ph SO ₂ Et 0
4-39 3-Cl-4-F-Ph SO ₂ Pr 0
4-40 3-Cl-4-F-Ph COMe 0
4-41 3-Cl-4-F-Ph COEt 0
4-42 3-Cl-4-F-Ph COPr 0
4-43 4-F-Ph CONH ₂ 2
4-44 4-F-Ph CONHMe 2
4-45 4-F-Ph CONHEt 2
4-46 4-F-Ph CONHPr 2
4-47 4-F-Ph CONH-i-Pr 2
4-48 4-F-Ph CONHBu 2
4-49 4-F-Ph SO ₂ NH ₂ 2
4-50 4-F-Ph SO ₂ NHMe 2
4-51 4-F-Ph SO ₂ NHEt 2
4-52 4-F-Ph SO ₂ NHPr 2
4-53 4-F-Ph SO ₂ NH-i-Pr 2
4-54 4-F-Ph SO ₂ NHBu 2
4-55 4-F-Ph SOMe 2
4-56 4-F-Ph SOEt 2
4-57 4-F-Ph SOPr 2
4-58 4-F-Ph SO ₂ Me 2
4-59 4-F-Ph SO ₂ Et 2
4-60 4-F-Ph SO ₂ Pr 2
4-61 4-F-Ph COMe 2
4-62 4-F-Ph COEt 2
4-63 4-F-Ph COPr 2
4-64 3-Cl-4-F-Ph CONH ₂ 2
4-65 3-Cl-4-F-Ph CONHMe 2
4-66 3-Cl-4-F-Ph CONHEt 2
4-67 3-Cl-4-F-Ph CONHPr 2
4-68 3-Cl-4-F-Ph CONH-i-Pr 2
4-69 3-Cl-4-F-Ph CONHBu 2
4-70 3-Cl-4-F-Ph SO ₂ NH ₂ 2
4-71 3-Cl-4-F-Ph SO ₂ NHMe 2
4-72 3-Cl-4-F-Ph SO ₂ NHEt 2
4-73 3-Cl-4-F-Ph SO ₂ NHPr 2
4-74 3-Cl-4-F-Ph SO ₂ NH-i-Pr 2
4-75 3-Cl-4-F-Ph SO ₂ NHBu 2
4-76 3-Cl-4-F-Ph SOMe 2
4-77 3-Cl-4-F-Ph SOEt 2
4-78 3-Cl-4-F-Ph SOPr 2
4-79 3-Cl-4-F-Ph SO ₂ Me 2
4-80 3-Cl-4-F-Ph SO ₂ Et 2
4-81 3-Cl-4-F-Ph SO ₂ Pr 2
4-82 3-Cl-4-F-Ph COMe 2
4-83 3-Cl-4-F-Ph COEt 2
4-84 3-Cl-4-F-Ph COPr 2
―――――――――――――――――――――
Table 5

―――――――――――――――――――――
Compound R ¹ R ⁵ m
No .――――――――――――――――――――――
5-1 4-F-Ph CONH ₂ 0
5-2 4-F-Ph CONHMe 0
5-3 4-F-Ph CONHEt 0
5-4 4-F-Ph CONHPr 0
5-5 4-F-Ph CONH-i-Pr 0
5-6 4-F-Ph CONHBu 0
5-7 4-F-Ph SO ₂ NH ₂ 0
5-8 4-F-Ph SO ₂ NHMe 0
5-9 4-F-Ph SO ₂ NHEt 0
5-10 4-F-Ph SO ₂ NHPr 0
5-11 4-F-Ph SO ₂ NH-i-Pr 0
5-12 4-F-Ph SO ₂ NHBu 0
5-13 4-F-Ph SOMe 0
5-14 4-F-Ph SOEt 0
5-15 4-F-Ph SOPr 0
5-16 4-F-Ph SO ₂ Me 0
5-17 4-F-Ph SO ₂ Et 0
5-18 4-F-Ph SO ₂ Pr 0
5-19 4-F-Ph COMe 0
5-20 4-F-Ph COEt 0
5-21 4-F-Ph COPr 0
5-22 3-Cl-4-F-Ph CONH ₂ 0
5-23 3-Cl-4-F-Ph CONHMe 0
5-24 3-Cl-4-F-Ph CONHEt 0
5-25 3-Cl-4-F-Ph CONHPr 0
5-26 3-Cl-4-F-Ph CONH-i-Pr 0
5-27 3-Cl-4-F-Ph CONHBu 0
5-28 3-Cl-4-F-Ph SO ₂ NH ₂ 0
5-29 3-Cl-4-F-Ph SO ₂ NHMe 0
5-30 3-Cl-4-F-Ph SO ₂ NHEt 0
5-31 3-Cl-4-F-Ph SO ₂ NHPr 0
5-32 3-Cl-4-F-Ph SO ₂ NH-i-Pr 0
5-33 3-Cl-4-F-Ph SO ₂ NHBu 0
5-34 3-Cl-4-F-Ph SOMe 0
5-35 3-Cl-4-F-Ph SOEt 0
5-36 3-Cl-4-F-Ph SOPr 0
5-37 3-Cl-4-F-Ph SO ₂ Me 0
5-38 3-Cl-4-F-Ph SO ₂ Et 0
5-39 3-Cl-4-F-Ph SO ₂ Pr 0
5-40 3-Cl-4-F-Ph COMe 0
5-41 3-Cl-4-F-Ph COEt 0
5-42 3-Cl-4-F-Ph COPr 0
5-43 4-F-Ph CONH ₂ 1
5-44 4-F-Ph CONHMe 1
5-45 4-F-Ph CONHEt 1
5-46 4-F-Ph CONHPr 1
5-47 4-F-Ph CONH-i-Pr 1
5-48 4-F-Ph CONHBu 1
5-49 4-F-Ph SO ₂ NH ₂ 1
5-50 4-F-Ph SO ₂ NHMe 1
5-51 4-F-Ph SO ₂ NHEt 1
5-52 4-F-Ph SO ₂ NHPr 1
5-53 4-F-Ph SO ₂ NH-i-Pr 1
5-54 4-F-Ph SO ₂ NHBu 1
5-55 4-F-Ph SOMe 1
5-56 4-F-Ph SOEt 1
5-57 4-F-Ph SOPr 1
5-58 4-F-Ph SO ₂ Me 1
5-59 4-F-Ph SO ₂ Et 1
5-60 4-F-Ph SO ₂ Pr 1
5-61 4-F-Ph COMe 1
5-62 4-F-Ph COEt 1
5-63 4-F-Ph COPr 1
5-64 3-Cl-4-F-Ph CONH ₂ 1
5-65 3-Cl-4-F-Ph CONHMe 1
5-66 3-Cl-4-F-Ph CONHEt 1
5-67 3-Cl-4-F-Ph CONHPr 1
5-68 3-Cl-4-F-Ph CONH-i-Pr 1
5-69 3-Cl-4-F-Ph CONHBu 1
5-70 3-Cl-4-F-Ph SO ₂ NH ₂ 1
5-71 3-Cl-4-F-Ph SO ₂ NHMe 1
5-72 3-Cl-4-F-Ph SO ₂ NHEt 1
5-73 3-Cl-4-F-Ph SO ₂ NHPr 1
5-74 3-Cl-4-F-Ph SO ₂ NH-i-Pr 1
5-75 3-Cl-4-F-Ph SO ₂ NHBu 1
5-76 3-Cl-4-F-Ph SOMe 1
5-77 3-Cl-4-F-Ph SOEt 1
5-78 3-Cl-4-F-Ph SOPr 1
5-79 3-Cl-4-F-Ph SO ₂ Me 1
5-80 3-Cl-4-F-Ph SO ₂ Et 1
5-81 3-Cl-4-F-Ph SO ₂ Pr 1
5-82 3-Cl-4-F-Ph COMe 1
5-83 3-Cl-4-F-Ph COEt 1
5-84 3-Cl-4-F-Ph COPr 1
5-85 4-F-Ph CONH ₂ 2
5-86 4-F-Ph CONHMe 2
5-87 4-F-Ph CONHEt 2
5-88 4-F-Ph CONHPr 2
5-89 4-F-Ph CONH-i-Pr 2
5-90 4-F-Ph CONHBu 2
5-91 4-F-Ph SO ₂ NH ₂ 2
5-92 4-F-Ph SO ₂ NHMe 2
5-93 4-F-Ph SO ₂ NHEt 2
5-94 4-F-Ph SO ₂ NHPr 2
5-95 4-F-Ph SO ₂ NH-i-Pr 2
5-96 4-F-Ph SO ₂ NHBu 2
5-97 4-F-Ph SOMe 2
5-98 4-F-Ph SOEt 2
5-99 4-F-Ph SOPr 2
5-100 4-F-Ph SO ₂ Me 2
5-101 4-F-Ph SO ₂ Et 2
5-102 4-F-Ph SO ₂ Pr 2
5-103 4-F-Ph COMe 2
5-104 4-F-Ph COEt 2
5-105 4-F-Ph COPr 2
5-106 3-Cl-4-F-Ph CONH ₂ 2
5-107 3-Cl-4-F-Ph CONHMe 2
5-108 3-Cl-4-F-Ph CONHEt 2
5-109 3-Cl-4-F-Ph CONHPr 2
5-110 3-Cl-4-F-Ph CONH-i-Pr 2
5-111 3-Cl-4-F-Ph CONHBu 2
5-112 3-Cl-4-F-Ph SO ₂ NH ₂ 2
5-113 3-Cl-4-F-Ph SO ₂ NHMe 2
5-114 3-Cl-4-F-Ph SO ₂ NHEt 2
5-115 3-Cl-4-F-Ph SO ₂ NHPr 2
5-116 3-Cl-4-F-Ph SO ₂ NH-i-Pr 2
5-117 3-Cl-4-F-Ph SO ₂ NHBu 2
5-118 3-Cl-4-F-Ph SOMe 2
5-119 3-Cl-4-F-Ph SOEt 2
5-120 3-Cl-4-F-Ph SOPr 2
5-121 3-Cl-4-F-Ph SO ₂ Me 2
5-122 3-Cl-4-F-Ph SO ₂ Et 2
5-123 3-Cl-4-F-Ph SO ₂ Pr 2
5-124 3-Cl-4-F-Ph COMe 2
5-125 3-Cl-4-F-Ph COEt 2
5-126 3-Cl-4-F-Ph COPr 2
―――――――――――――――――――――
Table 6

―――――――――――――――――――――――――
Compound R ¹ ZR ⁵
No .――――――――――――――――――――――――――
6-1 4-F-Ph Ring 1 CONH ₂
6-2 4-F-Ph Ring 1 CONHMe
6-3 4-F-Ph Ring 1 CONHEt
6-4 4-F-Ph Ring 1 CONHPr
6-5 4-F-Ph Ring 1 CONH-i-Pr
6-6 4-F-Ph Ring 1 CONHBu
6-7 4-F-Ph Ring 1 SO ₂ NH ₂
6-8 4-F-Ph Ring 1 SO ₂ NHMe
6-9 4-F-Ph Ring 1 SO ₂ NHEt
6-10 4-F-Ph Ring 1 SO ₂ NHPr
6-11 4-F-Ph Ring 1 SO ₂ NH-i-Pr
6-12 4-F-Ph Ring 1 SO ₂ NHBu
6-13 4-F-Ph Ring 1 SOMe
6-14 4-F-Ph Ring 1 SOEt
6-15 4-F-Ph Ring 1 SOPr
6-16 4-F-Ph Ring 1 SO ₂ Me
6-17 4-F-Ph Ring 1 SO ₂ Et
6-18 4-F-Ph Ring 1 SO ₂ Pr
6-19 4-F-Ph Ring 1 COMe
6-20 4-F-Ph Ring 1 COEt
6-21 4-F-Ph Ring 1 COPr
6-22 3-Cl-4-F-Ph Ring 1 CONH ₂
6-23 3-Cl-4-F-Ph Ring 1 CONHMe
6-24 3-Cl-4-F-Ph Ring 1 CONHEt
6-25 3-Cl-4-F-Ph Ring 1 CONHPr
6-26 3-Cl-4-F-Ph Ring 1 CONH-i-Pr
6-27 3-Cl-4-F-Ph Ring 1 CONHBu
6-28 3-Cl-4-F-Ph Ring 1 SO ₂ NH ₂
6-29 3-Cl-4-F-Ph Ring 1 SO ₂ NHMe
6-30 3-Cl-4-F-Ph Ring 1 SO ₂ NHEt
6-31 3-Cl-4-F-Ph Ring 1 SO ₂ NHPr
6-32 3-Cl-4-F-Ph Ring 1 SO ₂ NH-i-Pr
6-33 3-Cl-4-F-Ph Ring 1 SO ₂ NHBu
6-34 3-Cl-4-F-Ph Ring 1 SOMe
6-35 3-Cl-4-F-Ph Ring 1 SOEt
6-36 3-Cl-4-F-Ph Ring 1 SOPr
6-37 3-Cl-4-F-Ph Ring 1 SO ₂ Me
6-38 3-Cl-4-F-Ph Ring 1 SO ₂ Et
6-39 3-Cl-4-F-Ph Ring 1 SO ₂ Pr
6-40 3-Cl-4-F-Ph Ring 1 COMe
6-41 3-Cl-4-F-Ph Ring 1 COEt
6-42 3-Cl-4-F-Ph Ring 1 COPr
6-43 4-F-Ph Ring 2 CONH ₂
6-44 4-F-Ph Ring 2 CONHMe
6-45 4-F-Ph Ring 2 CONHEt
6-46 4-F-Ph Ring 2 CONHPr
6-47 4-F-Ph Ring 2 CONH-i-Pr
6-48 4-F-Ph Ring 2 CONHBu
6-49 4-F-Ph Ring 2 SO ₂ NH ₂
6-50 4-F-Ph Ring 2 SO ₂ NHMe
6-51 4-F-Ph Ring 2 SO ₂ NHEt
6-52 4-F-Ph Ring 2 SO ₂ NHPr
6-53 4-F-Ph Ring 2 SO ₂ NH-i-Pr
6-54 4-F-Ph Ring 2 SO ₂ NHBu
6-55 4-F-Ph Ring 2 SOMe
6-56 4-F-Ph Ring 2 SOEt
6-57 4-F-Ph Ring 2 SOPr
6-58 4-F-Ph Ring 2 SO ₂ Me
6-59 4-F-Ph Ring 2 SO ₂ Et
6-60 4-F-Ph Ring 2 SO ₂ Pr
6-61 4-F-Ph Ring 2 COMe
6-62 4-F-Ph Ring 2 COEt
6-63 4-F-Ph Ring 2 COPr
6-64 3-Cl-4-F-Ph Ring 2 CONH ₂
6-65 3-Cl-4-F-Ph Ring 2 CONHMe
6-66 3-Cl-4-F-Ph Ring 2 CONHEt
6-67 3-Cl-4-F-Ph Ring 2 CONHPr
6-68 3-Cl-4-F-Ph Ring 2 CONH-i-Pr
6-69 3-Cl-4-F-Ph Ring 2 CONHBu
6-70 3-Cl-4-F-Ph Ring 2 SO ₂ NH ₂
6-71 3-Cl-4-F-Ph Ring 2 SO ₂ NHMe
6-72 3-Cl-4-F-Ph Ring 2 SO ₂ NHEt
6-73 3-Cl-4-F-Ph Ring 2 SO ₂ NHPr
6-74 3-Cl-4-F-Ph Ring 2 SO ₂ NH-i-Pr
6-75 3-Cl-4-F-Ph Ring 2 SO ₂ NHBu
6-76 3-Cl-4-F-Ph Ring 2 SOMe
6-77 3-Cl-4-F-Ph Ring 2 SOEt
6-78 3-Cl-4-F-Ph Ring 2 SOPr
6-79 3-Cl-4-F-Ph Ring 2 SO ₂ Me
6-80 3-Cl-4-F-Ph Ring 2 SO ₂ Et
6-81 3-Cl-4-F-Ph Ring 2 SO ₂ Pr
6-82 3-Cl-4-F-Ph Ring 2 COMe
6-83 3-Cl-4-F-Ph Ring 2 COEt
6-84 3-Cl-4-F-Ph Ring 2 COPr
6-85 4-F-Ph Ring 3 CONH ₂
6-86 4-F-Ph Ring 3 CONHMe
6-87 4-F-Ph Ring 3 CONHEt
6-88 4-F-Ph Ring 3 CONHPr
6-89 4-F-Ph Ring 3 CONH-i-Pr
6-90 4-F-Ph Ring 3 CONHBu
6-91 4-F-Ph Ring 3 SO ₂ NH ₂
6-92 4-F-Ph Ring 3 SO ₂ NHMe
6-93 4-F-Ph Ring 3 SO ₂ NHEt
6-94 4-F-Ph Ring 3 SO ₂ NHPr
6-95 4-F-Ph Ring 3 SO ₂ NH-i-Pr
6-96 4-F-Ph Ring 3 SO ₂ NHBu
6-97 4-F-Ph Ring 3 SOMe
6-98 4-F-Ph Ring 3 SOEt
6-99 4-F-Ph Ring 3 SOPr
6-100 4-F-Ph Ring 3 SO ₂ Me
6-101 4-F-Ph Ring 3 SO ₂ Et
6-102 4-F-Ph Ring 3 SO ₂ Pr
6-103 4-F-Ph Ring 3 COMe
6-104 4-F-Ph Ring 3 COEt
6-105 4-F-Ph Ring 3 COPr
6-106 3-Cl-4-F-Ph Ring 3 CONH ₂
6-107 3-Cl-4-F-Ph Ring 3 CONHMe
6-108 3-Cl-4-F-Ph Ring 3 CONHEt
6-109 3-Cl-4-F-Ph Ring 3 CONHPr
6-110 3-Cl-4-F-Ph Ring 3 CONH-i-Pr
6-111 3-Cl-4-F-Ph Ring 3 CONHBu
6-112 3-Cl-4-F-Ph Ring 3 SO ₂ NH ₂
6-113 3-Cl-4-F-Ph Ring 3 SO ₂ NHMe
6-114 3-Cl-4-F-Ph Ring 3 SO ₂ NHEt
6-115 3-Cl-4-F-Ph Ring 3 SO ₂ NHPr
6-116 3-Cl-4-F-Ph Ring 3 SO ₂ NH-i-Pr
6-117 3-Cl-4-F-Ph Ring 3 SO ₂ NHBu
6-118 3-Cl-4-F-Ph Ring 3 SOMe
6-119 3-Cl-4-F-Ph Ring 3 SOEt
6-120 3-Cl-4-F-Ph Ring 3 SOPr
6-121 3-Cl-4-F-Ph Ring 3 SO ₂ Me
6-122 3-Cl-4-F-Ph Ring 3 SO ₂ Et
6-123 3-Cl-4-F-Ph Ring 3 SO ₂ Pr
6-124 3-Cl-4-F-Ph Ring 3 COMe
6-125 3-Cl-4-F-Ph Ring 3 COEt
6-126 3-Cl-4-F-Ph Ring 3 COPr
6-127 4-F-Ph Ring 4 CONH ₂
6-128 4-F-Ph Ring 4 CONHMe
6-129 4-F-Ph Ring 4 CONHEt
6-130 4-F-Ph Ring 4 CONHPr
6-131 4-F-Ph Ring 4 CONH-i-Pr
6-132 4-F-Ph Ring 4 CONHBu
6-133 4-F-Ph Ring 4 SO ₂ NH ₂
6-134 4-F-Ph Ring 4 SO ₂ NHMe
6-135 4-F-Ph Ring 4 SO ₂ NHEt
6-136 4-F-Ph Ring 4 SO ₂ NHPr
6-137 4-F-Ph Ring 4 SO ₂ NH-i-Pr
6-138 4-F-Ph Ring 4 SO ₂ NHBu
6-139 4-F-Ph Ring 4 SOMe
6-140 4-F-Ph Ring 4 SOEt
6-141 4-F-Ph Ring 4 SOPr
6-142 4-F-Ph Ring 4 SO ₂ Me
6-143 4-F-Ph Ring 4 SO ₂ Et
6-144 4-F-Ph Ring 4 SO ₂ Pr
6-145 4-F-Ph Ring 4 COMe
6-146 4-F-Ph Ring 4 COEt
6-147 4-F-Ph Ring 4 COPr
6-148 3-Cl-4-F-Ph Ring 4 CONH ₂
6-149 3-Cl-4-F-Ph Ring 4 CONHMe
6-150 3-Cl-4-F-Ph Ring 4 CONHEt
6-151 3-Cl-4-F-Ph Ring 4 CONHPr
6-152 3-Cl-4-F-Ph Ring 4 CONH-i-Pr
6-153 3-Cl-4-F-Ph Ring 4 CONHBu
6-154 3-Cl-4-F-Ph Ring 4 SO ₂ NH ₂
6-155 3-Cl-4-F-Ph Ring 4 SO ₂ NHMe
6-156 3-Cl-4-F-Ph Ring 4 SO ₂ NHEt
6-157 3-Cl-4-F-Ph ring 4 SO ₂ NHPr
6-158 3-Cl-4-F-Ph Ring 4 SO ₂ NH-i-Pr
6-159 3-Cl-4-F-Ph Ring 4 SO ₂ NHBu
6-160 3-Cl-4-F-Ph Ring 4 SOMe
6-161 3-Cl-4-F-Ph Ring 4 SOEt
6-162 3-Cl-4-F-Ph Ring 4 SOPr
6-163 3-Cl-4-F-Ph Ring 4 SO ₂ Me
6-164 3-Cl-4-F-Ph Ring 4 SO ₂ Et
6-165 3-Cl-4-F-Ph Ring 4 SO ₂ Pr
6-166 3-Cl-4-F-Ph Ring 4 COMe
6-167 3-Cl-4-F-Ph Ring 4 COEt
6-168 3-Cl-4-F-Ph Ring 4 COPr
6-169 4-F-Ph Ring 5 CONH ₂
6-170 4-F-Ph Ring 5 CONHMe
6-171 4-F-Ph Ring 5 CONHEt
6-172 4-F-Ph Ring 5 CONHPr
6-173 4-F-Ph Ring 5 CONH-i-Pr
6-174 4-F-Ph Ring 5 CONHBu
6-175 4-F-Ph Ring 5 SO ₂ NH ₂
6-176 4-F-Ph Ring 5 SO ₂ NHMe
6-177 4-F-Ph Ring 5 SO ₂ NHEt
6-178 4-F-Ph Ring 5 SO ₂ NHPr
6-179 4-F-Ph Ring 5 SO ₂ NH-i-Pr
6-180 4-F-Ph Ring 5 SO ₂ NHBu
6-181 4-F-Ph Ring 5 SOMe
6-182 4-F-Ph Ring 5 SOEt
6-183 4-F-Ph Ring 5 SOPr
6-184 4-F-Ph Ring 5 SO ₂ Me
6-185 4-F-Ph Ring 5 SO ₂ Et
6-186 4-F-Ph Ring 5 SO ₂ Pr
6-187 4-F-Ph Ring 5 COMe
6-188 4-F-Ph Ring 5 COEt
6-189 4-F-Ph Ring 5 COPr
6-190 3-Cl-4-F-Ph Ring 5 CONH ₂
6-191 3-Cl-4-F-Ph Ring 5 CONHMe
6-192 3-Cl-4-F-Ph Ring 5 CONHEt
6-193 3-Cl-4-F-Ph Ring 5 CONHPr
6-194 3-Cl-4-F-Ph Ring 5 CONH-i-Pr
6-195 3-Cl-4-F-Ph Ring 5 CONHBu
6-196 3-Cl-4-F-Ph Ring 5 SO ₂ NH ₂
6-197 3-Cl-4-F-Ph Ring 5 SO ₂ NHMe
6-198 3-Cl-4-F-Ph Ring 5 SO ₂ NHEt
6-199 3-Cl-4-F-Ph Ring 5 SO ₂ NHPr
6-200 3-Cl-4-F-Ph Ring 5 SO ₂ NH-i-Pr
6-201 3-Cl-4-F-Ph Ring 5 SO ₂ NHBu
6-202 3-Cl-4-F-Ph Ring 5 SOMe
6-203 3-Cl-4-F-Ph Ring 5 SOEt
6-204 3-Cl-4-F-Ph Ring 5 SOPr
6-205 3-Cl-4-F-Ph Ring 5 SO ₂ Me
6-206 3-Cl-4-F-Ph Ring 5 SO ₂ Et
6-207 3-Cl-4-F-Ph Ring 5 SO ₂ Pr
6-208 3-Cl-4-F-Ph Ring 5 COMe
6-209 3-Cl-4-F-Ph Ring 5 COEt
6-210 3-Cl-4-F-Ph Ring 5 COPr
6-211 4-F-Ph Ring 6 CONH ₂
6-212 4-F-Ph Ring 6 CONHMe
6-213 4-F-Ph Ring 6 CONHEt
6-214 4-F-Ph Ring 6 CONHPr
6-215 4-F-Ph Ring 6 CONH-i-Pr
6-216 4-F-Ph Ring 6 CONHBu
6-217 4-F-Ph Ring 6 SO ₂ NH ₂
6-218 4-F-Ph Ring 6 SO ₂ NHMe
6-219 4-F-Ph Ring 6 SO ₂ NHEt
6-220 4-F-Ph Ring 6 SO ₂ NHPr
6-221 4-F-Ph Ring 6 SO ₂ NH-i-Pr
6-222 4-F-Ph Ring 6 SO ₂ NHBu
6-223 4-F-Ph Ring 6 SOMe
6-224 4-F-Ph Ring 6 SOEt
6-225 4-F-Ph Ring 6 SOPr
6-226 4-F-Ph Ring 6 SO ₂ Me
6-227 4-F-Ph Ring 6 SO ₂ Et
6-228 4-F-Ph Ring 6 SO ₂ Pr
6-229 4-F-Ph Ring 6 COMe
6-230 4-F-Ph Ring 6 COEt
6-231 4-F-Ph Ring 6 COPr
6-232 3-Cl-4-F-Ph Ring 6 CONH ₂
6-233 3-Cl-4-F-Ph Ring 6 CONHMe
6-234 3-Cl-4-F-Ph Ring 6 CONHEt
6-235 3-Cl-4-F-Ph Ring 6 CONHPr
6-236 3-Cl-4-F-Ph Ring 6 CONH-i-Pr
6-237 3-Cl-4-F-Ph Ring 6 CONHBu
6-238 3-Cl-4-F-Ph Ring 6 SO ₂ NH ₂
6-239 3-Cl-4-F-Ph Ring 6 SO ₂ NHMe
6-240 3-Cl-4-F-Ph Ring 6 SO ₂ NHEt
6-241 3-Cl-4-F-Ph ring 6 SO ₂ NHPr
6-242 3-Cl-4-F-Ph ring 6 SO ₂ NH-i-Pr
6-243 3-Cl-4-F-Ph Ring 6 SO ₂ NHBu
6-244 3-Cl-4-F-Ph Ring 6 SOMe
6-245 3-Cl-4-F-Ph Ring 6 SOEt
6-246 3-Cl-4-F-Ph Ring 6 SOPr
6-247 3-Cl-4-F-Ph Ring 6 SO ₂ Me
6-248 3-Cl-4-F-Ph Ring 6 SO ₂ Et
6-249 3-Cl-4-F-Ph Ring 6 SO ₂ Pr
6-250 3-Cl-4-F-Ph Ring 6 COMe
6-251 3-Cl-4-F-Ph Ring 6 COEt
6-252 3-Cl-4-F-Ph Ring 6 COPr
6-253 4-F-Ph Ring 7 CONH ₂
6-254 4-F-Ph Ring 7 CONHMe
6-255 4-F-Ph Ring 7 CONHEt
6-256 4-F-Ph Ring 7 CONHPr
6-257 4-F-Ph Ring 7 CONH-i-Pr
6-258 4-F-Ph Ring 7 CONHBu
6-259 4-F-Ph Ring 7 SO ₂ NH ₂
6-260 4-F-Ph Ring 7 SO ₂ NHMe
6-261 4-F-Ph Ring 7 SO ₂ NHEt
6-262 4-F-Ph Ring 7 SO ₂ NHPr
6-263 4-F-Ph Ring 7 SO ₂ NH-i-Pr
6-264 4-F-Ph Ring 7 SO ₂ NHBu
6-265 4-F-Ph Ring 7 SOMe
6-266 4-F-Ph Ring 7 SOEt
6-267 4-F-Ph Ring 7 SOPr
6-268 4-F-Ph Ring 7 SO ₂ Me
6-269 4-F-Ph Ring 7 SO ₂ Et
6-270 4-F-Ph Ring 7 SO ₂ Pr
6-271 4-F-Ph Ring 7 COMe
6-272 4-F-Ph Ring 7 COEt
6-273 4-F-Ph Ring 7 COPr
6-274 3-Cl-4-F-Ph Ring 7 CONH ₂
6-275 3-Cl-4-F-Ph Ring 7 CONHMe
6-276 3-Cl-4-F-Ph Ring 7 CONHEt
6-277 3-Cl-4-F-Ph Ring 7 CONHPr
6-278 3-Cl-4-F-Ph Ring 7 CONH-i-Pr
6-279 3-Cl-4-F-Ph Ring 7 CONHBu
6-280 3-Cl-4-F-Ph Ring 7 SO ₂ NH ₂
6-281 3-Cl-4-F-Ph Ring 7 SO ₂ NHMe
6-282 3-Cl-4-F-Ph Ring 7 SO ₂ NHEt
6-283 3-Cl-4-F-Ph ring 7 SO ₂ NHPr
6-284 3-Cl-4-F-Ph Ring 7 SO ₂ NH-i-Pr
6-285 3-Cl-4-F-Ph Ring 7 SO ₂ NHBu
6-286 3-Cl-4-F-Ph Ring 7 SOMe
6-287 3-Cl-4-F-Ph Ring 7 SOEt
6-288 3-Cl-4-F-Ph Ring 7 SOPr
6-289 3-Cl-4-F-Ph Ring 7 SO ₂ Me
6-290 3-Cl-4-F-Ph Ring 7 SO ₂ Et
6-291 3-Cl-4-F-Ph Ring 7 SO ₂ Pr
6-292 3-Cl-4-F-Ph Ring 7 COMe
6-293 3-Cl-4-F-Ph Ring 7 COEt
6-294 3-Cl-4-F-Ph Ring 7 COPr
6-295 4-F-Ph Ring 8 CONH ₂
6-296 4-F-Ph Ring 8 CONHMe
6-297 4-F-Ph Ring 8 CONHEt
6-298 4-F-Ph Ring 8 CONHPr
6-299 4-F-Ph Ring 8 CONH-i-Pr
6-300 4-F-Ph Ring 8 CONHBu
6-301 4-F-Ph Ring 8 SO ₂ NH ₂
6-302 4-F-Ph Ring 8 SO ₂ NHMe
6-303 4-F-Ph Ring 8 SO ₂ NHEt
6-304 4-F-Ph Ring 8 SO ₂ NHPr
6-305 4-F-Ph Ring 8 SO ₂ NH-i-Pr
6-306 4-F-Ph Ring 8 SO ₂ NHBu
6-307 4-F-Ph Ring 8 SOMe
6-308 4-F-Ph Ring 8 SOEt
6-309 4-F-Ph Ring 8 SOPr
6-310 4-F-Ph Ring 8 SO ₂ Me
6-311 4-F-Ph Ring 8 SO ₂ Et
6-312 4-F-Ph Ring 8 SO ₂ Pr
6-313 4-F-Ph Ring 8 COMe
6-314 4-F-Ph Ring 8 COEt
6-315 4-F-Ph Ring 8 COPr
6-316 3-Cl-4-F-Ph Ring 8 CONH ₂
6-317 3-Cl-4-F-Ph Ring 8 CONHMe
6-318 3-Cl-4-F-Ph Ring 8 CONHEt
6-319 3-Cl-4-F-Ph Ring 8 CONHPr
6-320 3-Cl-4-F-Ph Ring 8 CONH-i-Pr
6-321 3-Cl-4-F-Ph Ring 8 CONHBu
6-322 3-Cl-4-F-Ph Ring 8 SO ₂ NH ₂
6-323 3-Cl-4-F-Ph Ring 8 SO ₂ NHMe
6-324 3-Cl-4-F-Ph Ring 8 SO ₂ NHEt
6-325 3-Cl-4-F-Ph ring 8 SO ₂ NHPr
6-326 3-Cl-4-F-Ph Ring 8 SO ₂ NH-i-Pr
6-327 3-Cl-4-F-Ph ring 8 SO ₂ NHBu
6-328 3-Cl-4-F-Ph Ring 8 SOMe
6-329 3-Cl-4-F-Ph Ring 8 SOEt
6-330 3-Cl-4-F-Ph Ring 8 SOPr
6-331 3-Cl-4-F-Ph Ring 8 SO ₂ Me
6-332 3-Cl-4-F-Ph Ring 8 SO ₂ Et
6-333 3-Cl-4-F-Ph Ring 8 SO ₂ Pr
6-334 3-Cl-4-F-Ph Ring 8 COMe
6-335 3-Cl-4-F-Ph Ring 8 COEt
6-336 3-Cl-4-F-Ph Ring 8 COPr
6-337 4-F-Ph Ring 9 CONH ₂
6-338 4-F-Ph Ring 9 CONHMe
6-339 4-F-Ph Ring 9 CONHEt
6-340 4-F-Ph Ring 9 CONHPr
6-341 4-F-Ph Ring 9 CONH-i-Pr
6-342 4-F-Ph Ring 9 CONHBu
6-343 4-F-Ph Ring 9 SO ₂ NH ₂
6-344 4-F-Ph Ring 9 SO ₂ NHMe
6-345 4-F-Ph Ring 9 SO ₂ NHEt
6-346 4-F-Ph ring 9 SO ₂ NHPr
6-347 4-F-Ph Ring 9 SO ₂ NH-i-Pr
6-348 4-F-Ph Ring 9 SO ₂ NHBu
6-349 4-F-Ph Ring 9 SOMe
6-350 4-F-Ph Ring 9 SOEt
6-351 4-F-Ph Ring 9 SOPr
6-352 4-F-Ph Ring 9 SO ₂ Me
6-353 4-F-Ph Ring 9 SO ₂ Et
6-354 4-F-Ph Ring 9 SO ₂ Pr
6-355 4-F-Ph Ring 9 COMe
6-356 4-F-Ph Ring 9 COEt
6-357 4-F-Ph Ring 9 COPr
6-358 3-Cl-4-F-Ph Ring 9 CONH ₂
6-359 3-Cl-4-F-Ph Ring 9 CONHMe
6-360 3-Cl-4-F-Ph Ring 9 CONHEt
6-361 3-Cl-4-F-Ph Ring 9 CONHPr
6-362 3-Cl-4-F-Ph Ring 9 CONH-i-Pr
6-363 3-Cl-4-F-Ph Ring 9 CONHBu
6-364 3-Cl-4-F-Ph Ring 9 SO ₂ NH ₂
6-365 3-Cl-4-F-Ph Ring 9 SO ₂ NHMe
6-366 3-Cl-4-F-Ph ring 9 SO ₂ NHEt
6-367 3-Cl-4-F-Ph ring 9 SO ₂ NHPr
6-368 3-Cl-4-F-Ph Ring 9 SO ₂ NH-i-Pr
6-369 3-Cl-4-F-Ph ring 9 SO ₂ NHBu
6-370 3-Cl-4-F-Ph Ring 9 SOMe
6-371 3-Cl-4-F-Ph Ring 9 SOEt
6-372 3-Cl-4-F-Ph Ring 9 SOPr
6-373 3-Cl-4-F-Ph Ring 9 SO ₂ Me
6-374 3-Cl-4-F-Ph ring 9 SO ₂ Et
6-375 3-Cl-4-F-Ph Ring 9 SO ₂ Pr
6-376 3-Cl-4-F-Ph Ring 9 COMe
6-377 3-Cl-4-F-Ph Ring 9 COEt
6-378 3-Cl-4-F-Ph Ring 9 COPr
6-379 4-F-Ph Ring 10 CONH ₂
6-380 4-F-Ph Ring 10 CONHMe
6-381 4-F-Ph Ring 10 CONHEt
6-382 4-F-Ph Ring 10 CONHPr
6-383 4-F-Ph Ring 10 CONH-i-Pr
6-384 4-F-Ph Ring 10 CONHBu
6-385 4-F-Ph Ring 10 SO ₂ NH ₂
6-386 4-F-Ph ring 10 SO ₂ NHMe
6-387 4-F-Ph Ring 10 SO ₂ NHEt
6-388 4-F-Ph Ring 10 SO ₂ NHPr
6-389 4-F-Ph Ring 10 SO ₂ NH-i-Pr
6-390 4-F-Ph Ring 10 SO ₂ NHBu
6-391 4-F-Ph Ring 10 SOMe
6-392 4-F-Ph Ring 10 SOEt
6-393 4-F-Ph Ring 10 SOPr
6-394 4-F-Ph Ring 10 SO ₂ Me
6-395 4-F-Ph Ring 10 SO ₂ Et
6-396 4-F-Ph Ring 10 SO ₂ Pr
6-397 4-F-Ph Ring 10 COMe
6-398 4-F-Ph Ring 10 COEt
6-399 4-F-Ph Ring 10 COPr
6-400 3-Cl-4-F-Ph Ring 10 CONH ₂
6-401 3-Cl-4-F-Ph Ring 10 CONHMe
6-402 3-Cl-4-F-Ph Ring 10 CONHEt
6-403 3-Cl-4-F-Ph Ring 10 CONHPr
6-404 3-Cl-4-F-Ph Ring 10 CONH-i-Pr
6-405 3-Cl-4-F-Ph Ring 10 CONHBu
6-406 3-Cl-4-F-Ph Ring 10 SO ₂ NH ₂
6-407 3-Cl-4-F-Ph Ring 10 SO ₂ NHMe
6-408 3-Cl-4-F-Ph Ring 10 SO ₂ NHEt
6-409 3-Cl-4-F-Ph Ring 10 SO ₂ NHPr
6-410 3-Cl-4-F-Ph Ring 10 SO ₂ NH-i-Pr
6-411 3-Cl-4-F-Ph Ring 10 SO ₂ NHBu
6-412 3-Cl-4-F-Ph Ring 10 SOMe
6-413 3-Cl-4-F-Ph Ring 10 SOEt
6-414 3-Cl-4-F-Ph Ring 10 SOPr
6-415 3-Cl-4-F-Ph Ring 10 SO ₂ Me
6-416 3-Cl-4-F-Ph Ring 10 SO ₂ Et
6-417 3-Cl-4-F-Ph Ring 10 SO ₂ Pr
6-418 3-Cl-4-F-Ph Ring 10 COMe
6-419 3-Cl-4-F-Ph Ring 10 COEt
6-420 3-Cl-4-F-Ph Ring 10 COPr
6-421 4-F-Ph Ring 11 CONH ₂
6-422 4-F-Ph Ring 11 CONHMe
6-423 4-F-Ph Ring 11 CONHEt
6-424 4-F-Ph Ring 11 CONHPr
6-425 4-F-Ph Ring 11 CONH-i-Pr
6-426 4-F-Ph Ring 11 CONHBu
6-427 4-F-Ph Ring 11 SO ₂ NH ₂
6-428 4-F-Ph Ring 11 SO ₂ NHMe
6-429 4-F-Ph Ring 11 SO ₂ NHEt
6-430 4-F-Ph Ring 11 SO ₂ NHPr
6-431 4-F-Ph Ring 11 SO ₂ NH-i-Pr
6-432 4-F-Ph Ring 11 SO ₂ NHBu
6-433 4-F-Ph Ring 11 SOMe
6-434 4-F-Ph Ring 11 SOEt
6-435 4-F-Ph Ring 11 SOPr
6-436 4-F-Ph Ring 11 SO ₂ Me
6-437 4-F-Ph Ring 11 SO ₂ Et
6-438 4-F-Ph Ring 11 SO ₂ Pr
6-439 4-F-Ph Ring 11 COMe
6-440 4-F-Ph Ring 11 COEt
6-441 4-F-Ph Ring 11 COPr
6-442 3-Cl-4-F-Ph Ring 11 CONH ₂
6-443 3-Cl-4-F-Ph Ring 11 CONHMe
6-444 3-Cl-4-F-Ph Ring 11 CONHEt
6-445 3-Cl-4-F-Ph Ring 11 CONHPr
6-446 3-Cl-4-F-Ph Ring 11 CONH-i-Pr
6-447 3-Cl-4-F-Ph Ring 11 CONHBu
6-448 3-Cl-4-F-Ph Ring 11 SO ₂ NH ₂
6-449 3-Cl-4-F-Ph Ring 11 SO ₂ NHMe
6-450 3-Cl-4-F-Ph Ring 11 SO ₂ NHEt
6-451 3-Cl-4-F-Ph Ring 11 SO ₂ NHPr
6-452 3-Cl-4-F-Ph Ring 11 SO ₂ NH-i-Pr
6-453 3-Cl-4-F-Ph Ring 11 SO ₂ NHBu
6-454 3-Cl-4-F-Ph Ring 11 SOMe
6-455 3-Cl-4-F-Ph Ring 11 SOEt
6-456 3-Cl-4-F-Ph Ring 11 SOPr
6-457 3-Cl-4-F-Ph Ring 11 SO ₂ Me
6-458 3-Cl-4-F-Ph Ring 11 SO ₂ Et
6-459 3-Cl-4-F-Ph Ring 11 SO ₂ Pr
6-460 3-Cl-4-F-Ph Ring 11 COMe
6-461 3-Cl-4-F-Ph Ring 11 COEt
6-462 3-Cl-4-F-Ph Ring 11 COPr
6-463 4-F-Ph Ring 12 CONH ₂
6-464 4-F-Ph Ring 12 CONHMe
6-465 4-F-Ph Ring 12 CONHEt
6-466 4-F-Ph Ring 12 CONHPr
6-467 4-F-Ph Ring 12 CONH-i-Pr
6-468 4-F-Ph Ring 12 CONHBu
6-469 4-F-Ph Ring 12 SO ₂ NH ₂
6-470 4-F-Ph Ring 12 SO ₂ NHMe
6-471 4-F-Ph Ring 12 SO ₂ NHEt
6-472 4-F-Ph Ring 12 SO ₂ NHPr
6-473 4-F-Ph Ring 12 SO ₂ NH-i-Pr
6-474 4-F-Ph Ring 12 SO ₂ NHBu
6-475 4-F-Ph Ring 12 SOMe
6-476 4-F-Ph Ring 12 SOEt
6-477 4-F-Ph Ring 12 SOPr
6-478 4-F-Ph Ring 12 SO ₂ Me
6-479 4-F-Ph Ring 12 SO ₂ Et
6-480 4-F-Ph Ring 12 SO ₂ Pr
6-481 4-F-Ph Ring 12 COMe
6-482 4-F-Ph Ring 12 COEt
6-483 4-F-Ph Ring 12 COPr
6-484 3-Cl-4-F-Ph Ring 12 CONH ₂
6-485 3-Cl-4-F-Ph Ring 12 CONHMe
6-486 3-Cl-4-F-Ph Ring 12 CONHEt
6-487 3-Cl-4-F-Ph Ring 12 CONHPr
6-488 3-Cl-4-F-Ph Ring 12 CONH-i-Pr
6-489 3-Cl-4-F-Ph Ring 12 CONHBu
6-490 3-Cl-4-F-Ph Ring 12 SO ₂ NH ₂
6-491 3-Cl-4-F-Ph Ring 12 SO ₂ NHMe
6-492 3-Cl-4-F-Ph Ring 12 SO ₂ NHEt
6-493 3-Cl-4-F-Ph Ring 12 SO ₂ NHPr
6-494 3-Cl-4-F-Ph Ring 12 SO ₂ NH-i-Pr
6-495 3-Cl-4-F-Ph Ring 12 SO ₂ NHBu
6-496 3-Cl-4-F-Ph Ring 12 SOMe
6-497 3-Cl-4-F-Ph Ring 12 SOEt
6-498 3-Cl-4-F-Ph Ring 12 SOPr
6-499 3-Cl-4-F-Ph Ring 12 SO ₂ Me
6-500 3-Cl-4-F-Ph Ring 12 SO ₂ Et
6-501 3-Cl-4-F-Ph Ring 12 SO ₂ Pr
6-502 3-Cl-4-F-Ph Ring 12 COMe
6-503 3-Cl-4-F-Ph Ring 12 COEt
6-504 3-Cl-4-F-Ph Ring 12 COPr
6-505 4-F-Ph Ring 13 CONH ₂
6-506 4-F-Ph Ring 13 CONHMe
6-507 4-F-Ph Ring 13 CONHEt
6-508 4-F-Ph Ring 13 CONHPr
6-509 4-F-Ph Ring 13 CONH-i-Pr
6-510 4-F-Ph Ring 13 CONHBu
6-511 4-F-Ph Ring 13 SO ₂ NH ₂
6-512 4-F-Ph Ring 13 SO ₂ NHMe
6-513 4-F-Ph Ring 13 SO ₂ NHEt
6-514 4-F-Ph Ring 13 SO ₂ NHPr
6-515 4-F-Ph Ring 13 SO ₂ NH-i-Pr
6-516 4-F-Ph Ring 13 SO ₂ NHBu
6-517 4-F-Ph Ring 13 SOMe
6-518 4-F-Ph Ring 13 SOEt
6-519 4-F-Ph Ring 13 SOPr
6-520 4-F-Ph Ring 13 SO ₂ Me
6-521 4-F-Ph Ring 13 SO ₂ Et
6-522 4-F-Ph Ring 13 SO ₂ Pr
6-523 4-F-Ph Ring 13 COMe
6-524 4-F-Ph Ring 13 COEt
6-525 4-F-Ph Ring 13 COPr
6-526 3-Cl-4-F-Ph Ring 13 CONH ₂
6-527 3-Cl-4-F-Ph Ring 13 CONHMe
6-528 3-Cl-4-F-Ph Ring 13 CONHEt
6-529 3-Cl-4-F-Ph Ring 13 CONHPr
6-530 3-Cl-4-F-Ph Ring 13 CONH-i-Pr
6-531 3-Cl-4-F-Ph Ring 13 CONHBu
6-532 3-Cl-4-F-Ph Ring 13 SO ₂ NH ₂
6-533 3-Cl-4-F-Ph Ring 13 SO ₂ NHMe
6-534 3-Cl-4-F-Ph Ring 13 SO ₂ NHEt
6-535 3-Cl-4-F-Ph Ring 13 SO ₂ NHPr
6-536 3-Cl-4-F-Ph Ring 13 SO ₂ NH-i-Pr
6-537 3-Cl-4-F-Ph Ring 13 SO ₂ NHBu
6-538 3-Cl-4-F-Ph Ring 13 SOMe
6-539 3-Cl-4-F-Ph Ring 13 SOEt
6-540 3-Cl-4-F-Ph Ring 13 SOPr
6-541 3-Cl-4-F-Ph Ring 13 SO ₂ Me
6-542 3-Cl-4-F-Ph Ring 13 SO ₂ Et
6-543 3-Cl-4-F-Ph Ring 13 SO ₂ Pr
6-544 3-Cl-4-F-Ph Ring 13 COMe
6-545 3-Cl-4-F-Ph Ring 13 COEt
6-546 3-Cl-4-F-Ph Ring 13 COPr
6-547 4-F-Ph Ring 14 CONH ₂
6-548 4-F-Ph Ring 14 CONHMe
6-549 4-F-Ph Ring 14 CONHEt
6-550 4-F-Ph Ring 14 CONHPr
6-551 4-F-Ph Ring 14 CONH-i-Pr
6-552 4-F-Ph Ring 14 CONHBu
6-553 4-F-Ph Ring 14 SO ₂ NH ₂
6-554 4-F-Ph Ring 14 SO ₂ NHMe
6-555 4-F-Ph Ring 14 SO ₂ NHEt
6-556 4-F-Ph Ring 14 SO ₂ NHPr
6-557 4-F-Ph Ring 14 SO ₂ NH-i-Pr
6-558 4-F-Ph Ring 14 SO ₂ NHBu
6-559 4-F-Ph Ring 14 SOMe
6-560 4-F-Ph Ring 14 SOEt
6-561 4-F-Ph Ring 14 SOPr
6-562 4-F-Ph Ring 14 SO ₂ Me
6-563 4-F-Ph Ring 14 SO ₂ Et
6-564 4-F-Ph Ring 14 SO ₂ Pr
6-565 4-F-Ph Ring 14 COMe
6-566 4-F-Ph Ring 14 COEt
6-567 4-F-Ph Ring 14 COPr
6-568 3-Cl-4-F-Ph Ring 14 CONH ₂
6-569 3-Cl-4-F-Ph Ring 14 CONHMe
6-570 3-Cl-4-F-Ph Ring 14 CONHEt
6-571 3-Cl-4-F-Ph Ring 14 CONHPr
6-572 3-Cl-4-F-Ph Ring 14 CONH-i-Pr
6-573 3-Cl-4-F-Ph Ring 14 CONHBu
6-574 3-Cl-4-F-Ph Ring 14 SO ₂ NH ₂
6-575 3-Cl-4-F-Ph ring 14 SO ₂ NHMe
6-576 3-Cl-4-F-Ph Ring 14 SO ₂ NHEt
6-577 3-Cl-4-F-Ph ring 14 SO ₂ NHPr
6-578 3-Cl-4-F-Ph Ring 14 SO ₂ NH-i-Pr
6-579 3-Cl-4-F-Ph ring 14 SO ₂ NHBu
6-580 3-Cl-4-F-Ph Ring 14 SOMe
6-581 3-Cl-4-F-Ph Ring 14 SOEt
6-582 3-Cl-4-F-Ph Ring 14 SOPr
6-583 3-Cl-4-F-Ph ring 14 SO ₂ Me
6-584 3-Cl-4-F-Ph ring 14 SO ₂ Et
6-585 3-Cl-4-F-Ph Ring 14 SO ₂ Pr
6-586 3-Cl-4-F-Ph Ring 14 COMe
6-587 3-Cl-4-F-Ph ring 14 COEt
6-588 3-Cl-4-F-Ph Ring 14 COPr
―――――――――――――――――――――――――
Table 7

―――――――――――――――――――――――――――――――
Compound R¹           R²            R^Five                    
Number
―――――――――――――――――――――――――――――――
7-1 Ph 4-Pyr COOH
7-2 Ph 4-Pyr COOMe
7-3 Ph 4-Pyr COOEt
7-4 Ph 4-Pyr COOPr
7-5 Ph 4-Pyr COO-i-Pr
7-6 Ph 4-Pyr COOBu
7-7 Ph 4-Pyr COOBn
7-8 Ph 4-Pyr COOPh
7-9 Ph 4-Pyr CONH₂              
7-10 Ph 4-Pyr CONHMe
7-11 Ph 4-Pyr CONHEt
7-12 Ph 4-Pyr CONHPr
7-13 Ph 4-Pyr CONH-i-Pr
7-14 Ph 4-Pyr CONHBu
7-15 Ph 4-Pyr CONHBn
7-16 Ph 4-Pyr CONMe₂             
7-17 Ph 4-Pyr CONH-c-Pr
7-18 Ph 4-Pyr CONH-c-Bu
7-19 Ph 4-Pyr CONH-c-Pen
7-20 Ph 4-Pyr CONH-c-Hex
7-21 Ph 4-Pyr CONH-c-Hep
7-22 Ph 4-Pyr CONHCH₂-c-Pr
7-23 Ph 4-Pyr CONH-Allyl
7-24 Ph 4-Pyr CONH-Propargyl
7-25 Ph 4-Pyr CONHPh
7-26 Ph 4-Pyr CONH-3-Pyr
7-27 Ph 4-Pyr CONHCH₂-4-Pyr
7-28 Ph 4-Pyr CONH- (CH₂)₂-OH
7-29 Ph 4-Pyr CONHCH (CH₂OH)₂       
7-30 Ph 4-Pyr CONH- (CH₂)₂-OAc
7-31 Ph 4-Pyr CONHCH₂CN
7-32 Ph 4-Pyr CONH- (CH₂)₂-F
7-33 Ph 4-Pyr CONH- (CH₂)₂-OMe
7-34 Ph 4-Pyr CONH- (CH₂)₂-SMe
7-35 Ph 4-Pyr CONH- (CH₂)₂-NH₂      
7-36 Ph 4-Pyr CONH- (CH₂)₂-NHMe
7-37 Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
7-38 Ph 4-Pyr CONHCH₂COOH
7-39 Ph 4-Pyr CONHCH₂COOEt
7-40 Ph 4-Pyr CONHCH (Me) COOEt
7-41 Ph 4-Pyr CONHCH₂CONH₂         
7-42 Ph 4-Pyr CONHOH
7-43 Ph 4-Pyr CONHOMe
7-44 Ph 4-Pyr CONHOEt
7-45 Ph 4-Pyr CONHOPr
7-46 Ph 4-Pyr CONHO-Allyl
7-47 Ph 4-Pyr CONHOBn
7-48 Ph 4-Pyr CONHNH₂            
7-49 Ph 4-Pyr CONHNHMe
7-50 Ph 4-Pyr CONHN (Me)₂          
7-51 Ph 4-Pyr COMe
7-52 Ph 4-Pyr COEt
7-53 Ph 4-Pyr COPr
7-54 Ph 4-Pyr CO-i-Pr
7-55 Ph 4-Pyr COBu
7-56 Ph 4-Pyr COCF_Three              
7-57 Ph 4-Pyr CO- (CH₂)₂-F
7-58 Ph 4-Pyr CO- (CH₂)₂-OH
7-59 Ph 4-Pyr CO- (CH₂)₂-OMe
7-60 Ph 4-Pyr SOMe
7-61 Ph 4-Pyr SOEt
7-62 Ph 4-Pyr SOPr
7-63 Ph 4-Pyr SO-i-Pr
7-64 Ph 4-Pyr SOBu
7-65 Ph 4-Pyr SOCF_Three              
7-66 Ph 4-Pyr SO- (CH₂)₂-F
7-67 Ph 4-Pyr SO- (CH₂)₂-OH
7-68 Ph 4-Pyr SO- (CH₂)₂-OMe
7-69 Ph 4-Pyr SO₂Me
7-70 Ph 4-Pyr SO₂Et
7-71 Ph 4-Pyr SO₂Pr
7-72 Ph 4-Pyr SO₂-i-Pr
7-73 Ph 4-Pyr SO₂Bu
7-74 Ph 4-Pyr SO₂CF_Three              
7-75 Ph 4-Pyr SO₂-(CH₂)₂-F
7-76 Ph 4-Pyr SO₂-(CH₂)₂-OH
7-77 Ph 4-Pyr SO₂-(CH₂)₂-OMe
7-78 Ph 4-Pyr SO₂NH₂              
7-79 Ph 4-Pyr SO₂NHMe
7-80 Ph 4-Pyr SO₂NHEt
7-81 Ph 4-Pyr SO₂NHPr
7-82 Ph 4-Pyr SO₂NH-i-Pr
7-83 Ph 4-Pyr SO₂NHBu
7-84 Ph 4-Pyr SO₂NHBn
7-85 Ph 4-Pyr SO₂NMe₂             
7-86 Ph 4-Pyr SO₂NH-c-Pr
7-87 Ph 4-Pyr SO₂NH-c-Bu
7-88 Ph 4-Pyr SO₂NH-c-Pen
7-89 Ph 4-Pyr SO₂NH-c-Hex
7-90 Ph 4-Pyr SO₂NH-c-Hep
7-91 Ph 4-Pyr SO₂NHCH₂-c-Pr
7-92 Ph 4-Pyr SO₂NH-Allyl
7-93 Ph 4-Pyr SO₂NH-Propargyl
7-94 Ph 4-Pyr SO₂NHPh
7-95 Ph 4-Pyr SO₂NH-3-Pyr
7-96 Ph 4-Pyr SO₂NHCH₂-4-Pyr
7-97 Ph 4-Pyr SO₂NH- (CH₂)₂-OH
7-98 Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
7-99 Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
7-100 Ph 4-Pyr SO₂NHCH₂CN
7-101 Ph 4-Pyr SO₂NH- (CH₂)₂-F
7-102 Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
7-103 Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
7-104 Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
7-105 Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
7-106 Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
7-107 Ph 4-Pyr SO₂NHCH₂COOH
7-108 Ph 4-Pyr SO₂NHCH₂COOEt
7-109 Ph 4-Pyr SO₂NHCH (Me) COOEt
7-110 Ph 4-Pyr SO₂NHCH₂CONH₂        
7-111 Ph 4-Pyr SO₂NHOH
7-112 Ph 4-Pyr SO₂NHOMe
7-113 Ph 4-Pyr SO₂NHOEt
7-114 Ph 4-Pyr SO₂NHOPr
7-115 Ph 4-Pyr SO₂NHOAllyl
7-116 Ph 4-Pyr SO₂NHOBn
7-117 Ph 4-Pyr SO₂NHNH₂            
7-118 Ph 4-Pyr SO₂NHNHMe
7-119 Ph 4-Pyr SO₂NHN (Me)₂          
7-120 3-F-Ph 4-Pyr COOH
7-121 3-F-Ph 4-Pyr COOMe
7-122 3-F-Ph 4-Pyr COOEt
7-123 3-F-Ph 4-Pyr COOPr
7-124 3-F-Ph 4-Pyr COO-i-Pr
7-125 3-F-Ph 4-Pyr COOBu
7-126 3-F-Ph 4-Pyr COOBn
7-127 3-F-Ph 4-Pyr COOPh
7-128 3-F-Ph 4-Pyr CONH₂              
7-129 3-F-Ph 4-Pyr CONHMe
7-130 3-F-Ph 4-Pyr CONHEt
7-131 3-F-Ph 4-Pyr CONHPr
7-132 3-F-Ph 4-Pyr CONH-i-Pr
7-133 3-F-Ph 4-Pyr CONHBu
7-134 3-F-Ph 4-Pyr CONHBn
7-135 3-F-Ph 4-Pyr CONMe₂             
7-136 3-F-Ph 4-Pyr CONH-c-Pr
7-137 3-F-Ph 4-Pyr CONH-c-Bu
7-138 3-F-Ph 4-Pyr CONH-c-Pen
7-139 3-F-Ph 4-Pyr CONH-c-Hex
7-140 3-F-Ph 4-Pyr CONH-c-Hep
7-141 3-F-Ph 4-Pyr CONHCH₂-c-Pr
7-142 3-F-Ph 4-Pyr CONH-Allyl
7-143 3-F-Ph 4-Pyr CONH-Propargyl
7-144 3-F-Ph 4-Pyr CONHPh
7-145 3-F-Ph 4-Pyr CONH-3-Pyr
7-146 3-F-Ph 4-Pyr CONHCH₂-4-Pyr
7-147 3-F-Ph 4-Pyr CONH- (CH₂)₂-OH
7-148 3-F-Ph 4-Pyr CONHCH (CH₂OH)₂       
7-149 3-F-Ph 4-Pyr CONH- (CH₂)₂-OAc
7-150 3-F-Ph 4-Pyr CONHCH₂CN
7-151 3-F-Ph 4-Pyr CONH- (CH₂)₂-F
7-152 3-F-Ph 4-Pyr CONH- (CH₂)₂-OMe
7-153 3-F-Ph 4-Pyr CONH- (CH₂)₂-SMe
7-154 3-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
7-155 3-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe
7-156 3-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
7-157 3-F-Ph 4-Pyr CONHCH₂COOH
7-158 3-F-Ph 4-Pyr CONHCH₂COOEt
7-159 3-F-Ph 4-Pyr CONHCH (Me) COOEt
7-160 3-F-Ph 4-Pyr CONHCH₂CONH₂        
7-161 3-F-Ph 4-Pyr CONHOH
7-162 3-F-Ph 4-Pyr CONHOMe
7-163 3-F-Ph 4-Pyr CONHOEt
7-164 3-F-Ph 4-Pyr CONHOPr
7-165 3-F-Ph 4-Pyr CONHOAllyl
7-166 3-F-Ph 4-Pyr CONHOBn
7-167 3-F-Ph 4-Pyr CONHNH₂             
7-168 3-F-Ph 4-Pyr CONHNHMe
7-169 3-F-Ph 4-Pyr CONHN (Me)₂          
7-170 3-F-Ph 4-Pyr COMe
7-171 3-F-Ph 4-Pyr COEt
7-172 3-F-Ph 4-Pyr COPr
7-173 3-F-Ph 4-Pyr CO-i-Pr
7-174 3-F-Ph 4-Pyr COBu
7-175 3-F-Ph 4-Pyr COCF_Three              
7-176 3-F-Ph 4-Pyr CO- (CH₂)₂-F
7-177 3-F-Ph 4-Pyr CO- (CH₂)₂-OH
7-178 3-F-Ph 4-Pyr CO- (CH₂)₂-OMe
7-179 3-F-Ph 4-Pyr SOMe
7-180 3-F-Ph 4-Pyr SOEt
7-181 3-F-Ph 4-Pyr SOPr
7-182 3-F-Ph 4-Pyr SO-i-Pr
7-183 3-F-Ph 4-Pyr SOBu
7-184 3-F-Ph 4-Pyr SOCF_Three              
7-185 3-F-Ph 4-Pyr SO- (CH₂)₂-F
7-186 3-F-Ph 4-Pyr SO- (CH₂)₂-OH
7-187 3-F-Ph 4-Pyr SO- (CH₂)₂-OMe
7-188 3-F-Ph 4-Pyr SO₂Me
7-189 3-F-Ph 4-Pyr SO₂Et
7-190 3-F-Ph 4-Pyr SO₂Pr
7-191 3-F-Ph 4-Pyr SO₂-i-Pr
7-192 3-F-Ph 4-Pyr SO₂Bu
7-193 3-F-Ph 4-Pyr SO₂CF_Three              
7-194 3-F-Ph 4-Pyr SO₂-(CH₂)₂-F
7-195 3-F-Ph 4-Pyr SO₂-(CH₂)₂-OH
7-196 3-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe
7-197 3-F-Ph 4-Pyr SO₂NH₂              
7-198 3-F-Ph 4-Pyr SO₂NHMe
7-199 3-F-Ph 4-Pyr SO₂NHEt
7-200 3-F-Ph 4-Pyr SO₂NHPr
7-201 3-F-Ph 4-Pyr SO₂NH-i-Pr
7-202 3-F-Ph 4-Pyr SO₂NHBu
7-203 3-F-Ph 4-Pyr SO₂NHBn
7-204 3-F-Ph 4-Pyr SO₂NMe₂            
7-205 3-F-Ph 4-Pyr SO₂NH-c-Pr
7-206 3-F-Ph 4-Pyr SO₂NH-c-Bu
7-207 3-F-Ph 4-Pyr SO₂NH-c-Pen
7-208 3-F-Ph 4-Pyr SO₂NH-c-Hex
7-209 3-F-Ph 4-Pyr SO₂NH-c-Hep
7-210 3-F-Ph 4-Pyr SO₂NHCH₂-c-Pr
7-211 3-F-Ph 4-Pyr SO₂NH-Allyl
7-212 3-F-Ph 4-Pyr SO₂NH-Propargyl
7-213 3-F-Ph 4-Pyr SO₂NHPh
7-214 3-F-Ph 4-Pyr SO₂NH-3-Pyr
7-215 3-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr
7-216 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
7-217 3-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
7-218 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
7-219 3-F-Ph 4-Pyr SO₂NHCH₂CN
7-220 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F
7-221 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
7-222 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
7-223 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
7-224 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
7-225 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
7-226 3-F-Ph 4-Pyr SO₂NHCH₂COOH
7-227 3-F-Ph 4-Pyr SO₂NHCH₂COOEt
7-228 3-F-Ph 4-Pyr SO₂NHCH (Me) COOEt
7-229 3-F-Ph 4-Pyr SO₂NHCH₂CONH₂        
7-230 3-F-Ph 4-Pyr SO₂NHOH
7-231 3-F-Ph 4-Pyr SO₂NHOMe
7-232 3-F-Ph 4-Pyr SO₂NHOEt
7-233 3-F-Ph 4-Pyr SO₂NHOPr
7-234 3-F-Ph 4-Pyr SO₂NHOAllyl
7-235 3-F-Ph 4-Pyr SO₂NHOBn
7-236 3-F-Ph 4-Pyr SO₂NHNH₂            
7-237 3-F-Ph 4-Pyr SO₂NHNHMe
7-238 3-F-Ph 4-Pyr SO₂NHN (Me)₂         
7-239 3-Cl-Ph 4-Pyr COOH
7-240 3-Cl-Ph 4-Pyr COOMe
7-241 3-Cl-Ph 4-Pyr COOEt
7-242 3-Cl-Ph 4-Pyr COOPr
7-243 3-Cl-Ph 4-Pyr COO-i-Pr
7-244 3-Cl-Ph 4-Pyr COOBu
7-245 3-Cl-Ph 4-Pyr COOBn
7-246 3-Cl-Ph 4-Pyr COOPh
7-247 3-Cl-Ph 4-Pyr CONH₂              
7-248 3-Cl-Ph 4-Pyr CONHMe
7-249 3-Cl-Ph 4-Pyr CONHEt
7-250 3-Cl-Ph 4-Pyr CONHPr
7-251 3-Cl-Ph 4-Pyr CONH-i-Pr
7-252 3-Cl-Ph 4-Pyr CONHBu
7-253 3-Cl-Ph 4-Pyr CONHBn
7-254 3-Cl-Ph 4-Pyr CONMe₂             
7-255 3-Cl-Ph 4-Pyr CONH-c-Pr
7-256 3-Cl-Ph 4-Pyr CONH-c-Bu
7-257 3-Cl-Ph 4-Pyr CONH-c-Pen
7-258 3-Cl-Ph 4-Pyr CONH-c-Hex
7-259 3-Cl-Ph 4-Pyr CONH-c-Hep
7-260 3-Cl-Ph 4-Pyr CONHCH₂-c-Pr
7-261 3-Cl-Ph 4-Pyr CONH-Allyl
7-262 3-Cl-Ph 4-Pyr CONH-Propargyl
7-263 3-Cl-Ph 4-Pyr CONHPh
7-264 3-Cl-Ph 4-Pyr CONH-3-Pyr
7-265 3-Cl-Ph 4-Pyr CONHCH₂-4-Pyr
7-266 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OH
7-267 3-Cl-Ph 4-Pyr CONHCH (CH₂OH)₂       
7-268 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OAc
7-269 3-Cl-Ph 4-Pyr CONHCH₂CN
7-270 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-F
7-271 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OMe
7-272 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-SMe
7-273 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
7-274 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-NHMe
7-275 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
7-276 3-Cl-Ph 4-Pyr CONHCH₂COOH
7-277 3-Cl-Ph 4-Pyr CONHCH₂COOEt
7-278 3-Cl-Ph 4-Pyr CONHCH (Me) COOEt
7-279 3-Cl-Ph 4-Pyr CONHCH₂CONH₂        
7-280 3-Cl-Ph 4-Pyr CONHOH
7-281 3-Cl-Ph 4-Pyr CONHOMe
7-282 3-Cl-Ph 4-Pyr CONHOEt
7-283 3-Cl-Ph 4-Pyr CONHOPr
7-284 3-Cl-Ph 4-Pyr CONHOAllyl
7-285 3-Cl-Ph 4-Pyr CONHOBn
7-286 3-Cl-Ph 4-Pyr CONHNH₂            
7-287 3-Cl-Ph 4-Pyr CONHNHMe
7-288 3-Cl-Ph 4-Pyr CONHN (Me)₂          
7-289 3-Cl-Ph 4-Pyr COMe
7-290 3-Cl-Ph 4-Pyr COEt
7-291 3-Cl-Ph 4-Pyr COPr
7-292 3-Cl-Ph 4-Pyr CO-i-Pr
7-293 3-Cl-Ph 4-Pyr COBu
7-294 3-Cl-Ph 4-Pyr COCF_Three               
7-295 3-Cl-Ph 4-Pyr CO- (CH₂)₂-F
7-296 3-Cl-Ph 4-Pyr CO- (CH₂)₂-OH
7-297 3-Cl-Ph 4-Pyr CO- (CH₂)₂-OMe
7-298 3-Cl-Ph 4-Pyr SOMe
7-299 3-Cl-Ph 4-Pyr SOEt
7-300 3-Cl-Ph 4-Pyr SOPr
7-301 3-Cl-Ph 4-Pyr SO-i-Pr
7-302 3-Cl-Ph 4-Pyr SOBu
7-303 3-Cl-Ph 4-Pyr SOCF_Three               
7-304 3-Cl-Ph 4-Pyr SO- (CH₂)₂-F
7-305 3-Cl-Ph 4-Pyr SO- (CH₂)₂-OH
7-306 3-Cl-Ph 4-Pyr SO- (CH₂)₂-OMe
7-307 3-Cl-Ph 4-Pyr SO₂Me
7-308 3-Cl-Ph 4-Pyr SO₂Et
7-309 3-Cl-Ph 4-Pyr SO₂Pr
7-310 3-Cl-Ph 4-Pyr SO₂-i-Pr
7-311 3-Cl-Ph 4-Pyr SO₂Bu
7-312 3-Cl-Ph 4-Pyr SO₂CF_Three              
7-313 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-F
7-314 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-OH
7-315 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-OMe
7-316 3-Cl-Ph 4-Pyr SO₂NH₂              
7-317 3-Cl-Ph 4-Pyr SO₂NHMe
7-318 3-Cl-Ph 4-Pyr SO₂NHEt
7-319 3-Cl-Ph 4-Pyr SO₂NHPr
7-320 3-Cl-Ph 4-Pyr SO₂NH-i-Pr
7-321 3-Cl-Ph 4-Pyr SO₂NHBu
7-322 3-Cl-Ph 4-Pyr SO₂NHBn
7-323 3-Cl-Ph 4-Pyr SO₂NMe₂             
7-324 3-Cl-Ph 4-Pyr SO₂NH-c-Pr
7-325 3-Cl-Ph 4-Pyr SO₂NH-c-Bu
7-326 3-Cl-Ph 4-Pyr SO₂NH-c-Pen
7-327 3-Cl-Ph 4-Pyr SO₂NH-c-Hex
7-328 3-Cl-Ph 4-Pyr SO₂NH-c-Hep
7-329 3-Cl-Ph 4-Pyr SO₂NHCH₂-c-Pr
7-330 3-Cl-Ph 4-Pyr SO₂NH-Allyl
7-331 3-Cl-Ph 4-Pyr SO₂NH-Propargyl
7-332 3-Cl-Ph 4-Pyr SO₂NHPh
7-333 3-Cl-Ph 4-Pyr SO₂NH-3-Pyr
7-334 3-Cl-Ph 4-Pyr SO₂NHCH₂-4-Pyr
7-335 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
7-336 3-Cl-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
7-337 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
7-338 3-Cl-Ph 4-Pyr SO₂NHCH₂CN
7-339 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-F
7-340 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
7-341 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
7-342 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
7-343 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
7-344 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂ 
7-345 3-Cl-Ph 4-Pyr SO₂NHCH₂COOH
7-346 3-Cl-Ph 4-Pyr SO₂NHCH₂COOEt
7-347 3-Cl-Ph 4-Pyr SO₂NHCH (Me) COOEt
7-348 3-Cl-Ph 4-Pyr SO₂NHCH₂CONH₂        
7-349 3-Cl-Ph 4-Pyr SO₂NHOH
7-350 3-Cl-Ph 4-Pyr SO₂NHOMe
7-351 3-Cl-Ph 4-Pyr SO₂NHOEt
7-352 3-Cl-Ph 4-Pyr SO₂NHOPr
7-353 3-Cl-Ph 4-Pyr SO₂NHOAllyl
7-354 3-Cl-Ph 4-Pyr SO₂NHOBn
7-355 3-Cl-Ph 4-Pyr SO₂NHNH₂            
7-356 3-Cl-Ph 4-Pyr SO₂NHNHMe
7-357 3-Cl-Ph 4-Pyr SO₂NHN (Me)₂         
7-358 4-F-Ph 4-Pyr COOH
7-359 4-F-Ph 4-Pyr COOMe
7-360 4-F-Ph 4-Pyr COOEt
7-361 4-F-Ph 4-Pyr COOPr
7-362 4-F-Ph 4-Pyr COO-i-Pr
7-363 4-F-Ph 4-Pyr COOBu
7-364 4-F-Ph 4-Pyr COOBn
7-365 4-F-Ph 4-Pyr COOPh
7-366 4-F-Ph 4-Pyr CONH₂               
7-367 4-F-Ph 4-Pyr CONHMe
7-368 4-F-Ph 4-Pyr CONHEt
7-369 4-F-Ph 4-Pyr CONHPr
7-370 4-F-Ph 4-Pyr CONH-i-Pr
7-371 4-F-Ph 4-Pyr CONHBu
7-372 4-F-Ph 4-Pyr CONHBn
7-373 4-F-Ph 4-Pyr CONMe₂              
7-374 4-F-Ph 4-Pyr CONH-c-Pr
7-375 4-F-Ph 4-Pyr CONH-c-Bu
7-376 4-F-Ph 4-Pyr CONH-c-Pen
7-377 4-F-Ph 4-Pyr CONH-c-Hex
7-378 4-F-Ph 4-Pyr CONH-c-Hep
7-379 4-F-Ph 4-Pyr CONHCH₂-c-Pr
7-380 4-F-Ph 4-Pyr CONH-Allyl
7-381 4-F-Ph 4-Pyr CONH-Propargyl
7-382 4-F-Ph 4-Pyr CONHPh
7-383 4-F-Ph 4-Pyr CONH-3-Pyr
7-384 4-F-Ph 4-Pyr CONHCH₂-4-Pyr
7-385 4-F-Ph 4-Pyr CONH- (CH₂)₂-OH
7-386 4-F-Ph 4-Pyr CONHCH (CH₂OH)₂      
7-387 4-F-Ph 4-Pyr CONH- (CH₂)₂-OAc
7-388 4-F-Ph 4-Pyr CONHCH₂CN
7-389 4-F-Ph 4-Pyr CONH- (CH₂)₂-F
7-390 4-F-Ph 4-Pyr CONH- (CH₂)₂-OMe
7-391 4-F-Ph 4-Pyr CONH- (CH₂)₂-SMe
7-392 4-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
7-393 4-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe
7-394 4-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
7-395 4-F-Ph 4-Pyr CONHCH₂COOH
7-396 4-F-Ph 4-Pyr CONHCH₂COOEt
7-397 4-F-Ph 4-Pyr CONHCH (Me) COOEt
7-398 4-F-Ph 4-Pyr CONHCH₂CONH₂        
7-399 4-F-Ph 4-Pyr CONHOH
7-400 4-F-Ph 4-Pyr CONHOMe
7-401 4-F-Ph 4-Pyr CONHOEt
7-402 4-F-Ph 4-Pyr CONHOPr
7-403 4-F-Ph 4-Pyr CONHOAllyl
7-404 4-F-Ph 4-Pyr CONHOBn
7-405 4-F-Ph 4-Pyr CONHNH₂             
7-406 4-F-Ph 4-Pyr CONHNHMe
7-407 4-F-Ph 4-Pyr CONHN (Me)₂          
7-408 4-F-Ph 4-Pyr COMe
7-409 4-F-Ph 4-Pyr COEt
7-410 4-F-Ph 4-Pyr COPr
7-411 4-F-Ph 4-Pyr CO-i-Pr
7-412 4-F-Ph 4-Pyr COBu
7-413 4-F-Ph 4-Pyr COCF_Three               
7-414 4-F-Ph 4-Pyr CO- (CH₂)₂-F         
7-415 4-F-Ph 4-Pyr CO- (CH₂)₂-OH
7-416 4-F-Ph 4-Pyr CO- (CH₂)₂-OMe
7-417 4-F-Ph 4-Pyr SOMe
7-418 4-F-Ph 4-Pyr SOEt
7-419 4-F-Ph 4-Pyr SOPr
7-420 4-F-Ph 4-Pyr SO-i-Pr
7-421 4-F-Ph 4-Pyr SOBu
7-422 4-F-Ph 4-Pyr SOCF_Three               
7-423 4-F-Ph 4-Pyr SO- (CH₂)₂-F
7-424 4-F-Ph 4-Pyr SO- (CH₂)₂-OH
7-425 4-F-Ph 4-Pyr SO- (CH₂)₂-OMe
7-426 4-F-Ph 4-Pyr SO₂Me
7-427 4-F-Ph 4-Pyr SO₂Et
7-428 4-F-Ph 4-Pyr SO₂Pr
7-429 4-F-Ph 4-Pyr SO₂-i-Pr
7-430 4-F-Ph 4-Pyr SO₂Bu
7-431 4-F-Ph 4-Pyr SO₂CF_Three              
7-432 4-F-Ph 4-Pyr SO₂-(CH₂)₂-F
7-433 4-F-Ph 4-Pyr SO₂-(CH₂)₂-OH
7-434 4-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe
7-435 4-F-Ph 4-Pyr SO₂NH₂              
7-436 4-F-Ph 4-Pyr SO₂NHMe
7-437 4-F-Ph 4-Pyr SO₂NHEt
7-438 4-F-Ph 4-Pyr SO₂NHPr
7-439 4-F-Ph 4-Pyr SO₂NH-i-Pr
7-440 4-F-Ph 4-Pyr SO₂NHBu
7-441 4-F-Ph 4-Pyr SO₂NHBn
7-442 4-F-Ph 4-Pyr SO₂NMe₂             
7-443 4-F-Ph 4-Pyr SO₂NH-c-Pr
7-444 4-F-Ph 4-Pyr SO₂NH-c-Bu
7-445 4-F-Ph 4-Pyr SO₂NH-c-Pen
7-446 4-F-Ph 4-Pyr SO₂NH-c-Hex
7-447 4-F-Ph 4-Pyr SO₂NH-c-Hep
7-448 4-F-Ph 4-Pyr SO₂NHCH₂-c-Pr
7-449 4-F-Ph 4-Pyr SO₂NH-Allyl
7-450 4-F-Ph 4-Pyr SO₂NH-Propargyl
7-451 4-F-Ph 4-Pyr SO₂NHPh
7-452 4-F-Ph 4-Pyr SO₂NH-3-Pyr
7-453 4-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr
7-454 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
7-455 4-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂     
7-456 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
7-457 4-F-Ph 4-Pyr SO₂NHCH₂CN
7-458 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F
7-459 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
7-460 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
7-461 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
7-462 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
7-463 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
7-464 4-F-Ph 4-Pyr SO₂NHCH₂COOH
7-465 4-F-Ph 4-Pyr SO₂NHCH₂COOEt
7-466 4-F-Ph 4-Pyr SO₂NHCH (Me) COOEt
7-467 4-F-Ph 4-Pyr SO₂NHCH₂CONH₂        
7-468 4-F-Ph 4-Pyr SO₂NHOH
7-469 4-F-Ph 4-Pyr SO₂NHOMe
7-470 4-F-Ph 4-Pyr SO₂NHOEt
7-471 4-F-Ph 4-Pyr SO₂NHOPr
7-472 4-F-Ph 4-Pyr SO₂NHOAllyl
7-473 4-F-Ph 4-Pyr SO₂NHOBn
7-474 4-F-Ph 4-Pyr SO₂NHNH₂            
7-475 4-F-Ph 4-Pyr SO₂NHNHMe
7-476 4-F-Ph 4-Pyr SO₂NHN (Me)₂         
7-477 3-Cl-4-F-Ph 4-Pyr COOH
7-478 3-Cl-4-F-Ph 4-Pyr COOMe
7-479 3-Cl-4-F-Ph 4-Pyr COOEt
7-480 3-Cl-4-F-Ph 4-Pyr COOPr
7-481 3-Cl-4-F-Ph 4-Pyr COO-i-Pr
7-482 3-Cl-4-F-Ph 4-Pyr COOBu
7-483 3-Cl-4-F-Ph 4-Pyr COOBn
7-484 3-Cl-4-F-Ph 4-Pyr COOPh
7-485 3-Cl-4-F-Ph 4-Pyr CONH₂              
7-486 3-Cl-4-F-Ph 4-Pyr CONHMe
7-487 3-Cl-4-F-Ph 4-Pyr CONHEt
7-488 3-Cl-4-F-Ph 4-Pyr CONHPr
7-489 3-Cl-4-F-Ph 4-Pyr CONH-i-Pr
7-490 3-Cl-4-F-Ph 4-Pyr CONHBu
7-491 3-Cl-4-F-Ph 4-Pyr CONHBn
7-492 3-Cl-4-F-Ph 4-Pyr CONMe₂             
7-493 3-Cl-4-F-Ph 4-Pyr CONH-c-Pr
7-494 3-Cl-4-F-Ph 4-Pyr CONH-c-Bu
7-495 3-Cl-4-F-Ph 4-Pyr CONH-c-Pen
7-496 3-Cl-4-F-Ph 4-Pyr CONH-c-Hex
7-497 3-Cl-4-F-Ph 4-Pyr CONH-c-Hep
7-498 3-Cl-4-F-Ph 4-Pyr CONHCH₂-c-Pr
7-499 3-Cl-4-F-Ph 4-Pyr CONH-Allyl
7-500 3-Cl-4-F-Ph 4-Pyr CONH-Propargyl
7-501 3-Cl-4-F-Ph 4-Pyr CONHPh
7-502 3-Cl-4-F-Ph 4-Pyr CONH-3-Pyr
7-503 3-Cl-4-F-Ph 4-Pyr CONHCH₂-4-Pyr
7-504 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OH
7-505 3-Cl-4-F-Ph 4-Pyr CONHCH (CH₂OH)₂      
7-506 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OAc
7-507 3-Cl-4-F-Ph 4-Pyr CONHCH₂CN
7-508 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-F
7-509 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OMe
7-510 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-SMe
7-511 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
7-512 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe
7-513 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
7-514 3-Cl-4-F-Ph 4-Pyr CONHCH₂COOH
7-515 3-Cl-4-F-Ph 4-Pyr CONHCH₂COOEt
7-516 3-Cl-4-F-Ph 4-Pyr CONHCH (Me) COOEt
7-517 3-Cl-4-F-Ph 4-Pyr CONHCH₂CONH₂        
7-518 3-Cl-4-F-Ph 4-Pyr CONHOH
7-519 3-Cl-4-F-Ph 4-Pyr CONHOMe
7-520 3-Cl-4-F-Ph 4-Pyr CONHOEt
7-521 3-Cl-4-F-Ph 4-Pyr CONHOPr
7-522 3-Cl-4-F-Ph 4-Pyr CONHOAllyl
7-523 3-Cl-4-F-Ph 4-Pyr CONHOBn
7-524 3-Cl-4-F-Ph 4-Pyr CONHNH₂             
7-525 3-Cl-4-F-Ph 4-Pyr CONHNHMe
7-526 3-Cl-4-F-Ph 4-Pyr CONHN (Me)₂          
7-527 3-Cl-4-F-Ph 4-Pyr COMe
7-528 3-Cl-4-F-Ph 4-Pyr COEt
7-529 3-Cl-4-F-Ph 4-Pyr COPr
7-530 3-Cl-4-F-Ph 4-Pyr CO-i-Pr
7-531 3-Cl-4-F-Ph 4-Pyr COBu
7-532 3-Cl-4-F-Ph 4-Pyr COCF_Three              
7-533 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-F
7-534 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-OH
7-535 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-OMe
7-536 3-Cl-4-F-Ph 4-Pyr SOMe
7-537 3-Cl-4-F-Ph 4-Pyr SOEt
7-538 3-Cl-4-F-Ph 4-Pyr SOPr
7-539 3-Cl-4-F-Ph 4-Pyr SO-i-Pr
7-540 3-Cl-4-F-Ph 4-Pyr SOBu
7-541 3-Cl-4-F-Ph 4-Pyr SOCF_Three              
7-542 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-F
7-543 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-OH
7-544 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-OMe
7-545 3-Cl-4-F-Ph 4-Pyr SO₂Me
7-546 3-Cl-4-F-Ph 4-Pyr SO₂Et
7-547 3-Cl-4-F-Ph 4-Pyr SO₂Pr
7-548 3-Cl-4-F-Ph 4-Pyr SO₂-i-Pr
7-549 3-Cl-4-F-Ph 4-Pyr SO₂Bu
7-550 3-Cl-4-F-Ph 4-Pyr SO₂CF_Three              
7-551 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-F
7-552 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-OH
7-553 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe
7-554 3-Cl-4-F-Ph 4-Pyr SO₂NH₂              
7-555 3-Cl-4-F-Ph 4-Pyr SO₂NHMe
7-556 3-Cl-4-F-Ph 4-Pyr SO₂NHEt
7-557 3-Cl-4-F-Ph 4-Pyr SO₂NHPr
7-558 3-Cl-4-F-Ph 4-Pyr SO₂NH-i-Pr
7-559 3-Cl-4-F-Ph 4-Pyr SO₂NHBu
7-560 3-Cl-4-F-Ph 4-Pyr SO₂NHBn
7-561 3-Cl-4-F-Ph 4-Pyr SO₂NMe₂             
7-562 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Pr
7-563 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Bu
7-564 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Pen
7-565 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Hex
7-566 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Hep
7-567 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂-c-Pr
7-568 3-Cl-4-F-Ph 4-Pyr SO₂NH-Allyl
7-569 3-Cl-4-F-Ph 4-Pyr SO₂NH-Propargyl
7-570 3-Cl-4-F-Ph 4-Pyr SO₂NHPh
7-571 3-Cl-4-F-Ph 4-Pyr SO₂NH-3-Pyr
7-572 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr
7-573 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
7-574 3-Cl-4-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
7-575 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
7-576 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂CN
7-577 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F
7-578 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
7-579 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
7-580 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
7-581 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
7-582 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
7-583 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂COOH
7-584 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂COOEt
7-585 3-Cl-4-F-Ph 4-Pyr SO₂NHCH (Me) COOEt
7-586 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂CONH₂        
7-587 3-Cl-4-F-Ph 4-Pyr SO₂NHOH
7-588 3-Cl-4-F-Ph 4-Pyr SO₂NHOMe
7-589 3-Cl-4-F-Ph 4-Pyr SO₂NHOEt
7-590 3-Cl-4-F-Ph 4-Pyr SO₂NHOPr
7-591 3-Cl-4-F-Ph 4-Pyr SO₂NHOAllyl
7-592 3-Cl-4-F-Ph 4-Pyr SO₂NHOBn
7-593 3-Cl-4-F-Ph 4-Pyr SO₂NHNH₂            
7-594 3-Cl-4-F-Ph 4-Pyr SO₂NHNHMe
7-595 3-Cl-4-F-Ph 4-Pyr SO₂NHN (Me)₂         
7-596 3,4-F₂-Ph       4-Pyr COOH
7-597 3,4-F₂-Ph       4-Pyr COOMe
7-598 3,4-F₂-Ph       4-Pyr COOEt
7-599 3,4-F₂-Ph       4-Pyr COOPr
7-600 3,4-F₂-Ph       4-Pyr COO-i-Pr
7-601 3,4-F₂-Ph       4-Pyr COOBu
7-602 3,4-F₂-Ph       4-Pyr COOBn
7-603 3,4-F₂-Ph       4-Pyr COOPh
7-604 3,4-F₂-Ph       4-Pyr CONH₂              
7-605 3,4-F₂-Ph       4-Pyr CONHMe
7-606 3,4-F₂-Ph       4-Pyr CONHEt
7-607 3,4-F₂-Ph       4-Pyr CONHPr
7-608 3,4-F₂-Ph       4-Pyr CONH-i-Pr
7-609 3,4-F₂-Ph       4-Pyr CONHBu
7-610 3,4-F₂-Ph       4-Pyr CONHBn
7-611 3,4-F₂-Ph       4-Pyr CONMe₂             
7-612 3,4-F₂-Ph       4-Pyr CONH-c-Pr
7-613 3,4-F₂-Ph       4-Pyr CONH-c-Bu
7-614 3,4-F₂-Ph       4-Pyr CONH-c-Pen
7-615 3,4-F₂-Ph       4-Pyr CONH-c-Hex
7-616 3,4-F₂-Ph       4-Pyr CONH-c-Hep
7-617 3,4-F₂-Ph       4-Pyr CONHCH₂-c-Pr
7-618 3,4-F₂-Ph       4-Pyr CONH-Allyl
7-619 3,4-F₂-Ph       4-Pyr CONH-Propargyl
7-620 3,4-F₂-Ph       4-Pyr CONHPh
7-621 3,4-F₂-Ph       4-Pyr CONH-3-Pyr
7-622 3,4-F₂-Ph       4-Pyr CONHCH₂-4-Pyr
7-623 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-OH
7-624 3,4-F₂-Ph       4-Pyr CONHCH (CH₂OH)₂      
7-625 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-OAc
7-626 3,4-F₂-Ph       4-Pyr CONHCH₂CN
7-627 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-F
7-628 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-OMe
7-629 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-SMe
7-630 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-NH₂      
7-631 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-NHMe
7-632 3,4-F₂-Ph       4-Pyr CONH- (CH₂)₂-N (Me)₂   
7-633 3,4-F₂-Ph       4-Pyr CONHCH₂COOH
7-634 3,4-F₂-Ph       4-Pyr CONHCH₂COOEt
7-635 3,4-F₂-Ph       4-Pyr CONHCH (Me) COOEt
7-636 3,4-F₂-Ph       4-Pyr CONHCH₂CONH₂        
7-637 3,4-F₂-Ph       4-Pyr CONHOH
7-638 3,4-F₂-Ph       4-Pyr CONHOMe
7-639 3,4-F₂-Ph       4-Pyr CONHOEt
7-640 3,4-F₂-Ph       4-Pyr CONHOPr
7-641 3,4-F₂-Ph       4-Pyr CONHOAllyl
7-642 3,4-F₂-Ph       4-Pyr CONHOBn
7-643 3,4-F₂-Ph       4-Pyr CONHNH₂            
7-644 3,4-F₂-Ph       4-Pyr CONHNHMe
7-645 3,4-F₂-Ph       4-Pyr CONHN (Me)₂          
7-646 3,4-F₂-Ph       4-Pyr COMe
7-647 3,4-F₂-Ph       4-Pyr COEt
7-648 3,4-F₂-Ph       4-Pyr COPr
7-649 3,4-F₂-Ph       4-Pyr CO-i-Pr
7-650 3,4-F₂-Ph       4-Pyr COBu
7-651 3,4-F₂-Ph       4-Pyr COCF_Three              
7-652 3,4-F₂-Ph       4-Pyr CO- (CH₂)₂-F
7-653 3,4-F₂-Ph       4-Pyr CO- (CH₂)₂-OH
7-654 3,4-F₂-Ph       4-Pyr CO- (CH₂)₂-OMe
7-655 3,4-F₂-Ph       4-Pyr SOMe
7-656 3,4-F₂-Ph       4-Pyr SOEt
7-657 3,4-F₂-Ph       4-Pyr SOPr
7-658 3,4-F₂-Ph       4-Pyr SO-i-Pr
7-659 3,4-F₂-Ph 4-Pyr SOBu
7-660 3,4-F₂-Ph       4-Pyr SOCF_Three              
7-661 3,4-F₂-Ph       4-Pyr SO- (CH₂)₂-F         
7-662 3,4-F₂-Ph       4-Pyr SO- (CH₂)₂-OH        
7-663 3,4-F₂-Ph       4-Pyr SO- (CH₂)₂-OMe       
7-664 3,4-F₂-Ph       4-Pyr SO₂Me
7-665 3,4-F₂-Ph       4-Pyr SO₂Et
7-666 3,4-F₂-Ph       4-Pyr SO₂Pr
7-667 3,4-F₂-Ph       4-Pyr SO₂-i-Pr
7-668 3,4-F₂-Ph       4-Pyr SO₂Bu
7-669 3,4-F₂-Ph       4-Pyr SO₂CF_Three             
7-670 3,4-F₂-Ph       4-Pyr SO₂-(CH₂)₂-F
7-671 3,4-F₂-Ph       4-Pyr SO₂-(CH₂)₂-OH
7-672 3,4-F₂-Ph       4-Pyr SO₂-(CH₂)₂-OMe
7-673 3,4-F₂-Ph       4-Pyr SO₂NH₂             
7-674 3,4-F₂-Ph       4-Pyr SO₂NHMe
7-675 3,4-F₂-Ph       4-Pyr SO₂NHEt
7-676 3,4-F₂-Ph       4-Pyr SO₂NHPr
7-677 3,4-F₂-Ph       4-Pyr SO₂NH-i-Pr
7-678 3,4-F₂-Ph       4-Pyr SO₂NHBu
7-679 3,4-F₂-Ph       4-Pyr SO₂NHBn
7-680 3,4-F₂-Ph       4-Pyr SO₂NMe₂            
7-681 3,4-F₂-Ph       4-Pyr SO₂NH-c-Pr
7-682 3,4-F₂-Ph       4-Pyr SO₂NH-c-Bu
7-683 3,4-F₂-Ph       4-Pyr SO₂NH-c-Pen
7-684 3,4-F₂-Ph       4-Pyr SO₂NH-c-Hex
7-685 3,4-F₂-Ph       4-Pyr SO₂NH-c-Hep
7-686 3,4-F₂-Ph       4-Pyr SO₂NHCH₂-c-Pr
7-687 3,4-F₂-Ph       4-Pyr SO₂NH-Allyl
7-688 3,4-F₂-Ph       4-Pyr SO₂NH-Propargyl
7-689 3,4-F₂-Ph       4-Pyr SO₂NHPh
7-690 3,4-F₂-Ph       4-Pyr SO₂NH-3-Pyr
7-691 3,4-F₂-Ph       4-Pyr SO₂NHCH₂-4-Pyr
7-692 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-OH
7-693 3,4-F₂-Ph       4-Pyr SO₂NHCH (CH₂OH)₂      
7-694 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-OAc
7-695 3,4-F₂-Ph       4-Pyr SO₂NHCH₂CN
7-696 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-F
7-697 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-OMe
7-698 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-SMe
7-699 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-NH₂     
7-700 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-NHMe
7-701 3,4-F₂-Ph       4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
7-702 3,4-F₂-Ph       4-Pyr SO₂NHCH₂COOH
7-703 3,4-F₂-Ph       4-Pyr SO₂NHCH₂COOEt
7-704 3,4-F₂-Ph       4-Pyr SO₂NHCH (Me) COOEt
7-705 3,4-F₂-Ph       4-Pyr SO₂NHCH₂CONH₂        
7-706 3,4-F₂-Ph       4-Pyr SO₂NHOH
7-707 3,4-F₂-Ph       4-Pyr SO₂NHOMe
7-708 3,4-F₂-Ph       4-Pyr SO₂NHOEt
7-709 3,4-F₂-Ph       4-Pyr SO₂NHOPr
7-710 3,4-F₂-Ph       4-Pyr SO₂NHOAllyl
7-711 3,4-F₂-Ph       4-Pyr SO₂NHOBn
7-712 3,4-F₂-Ph       4-Pyr SO₂NHNH₂            
7-713 3,4-F₂-Ph       4-Pyr SO₂NHNHMe
7-714 3,4-F₂-Ph       4-Pyr SO₂NHN (Me)₂        
7-715 3-CF_Three-Ph        4-Pyr COOH
7-716 3-CF_Three-Ph        4-Pyr COOMe
7-717 3-CF_Three-Ph        4-Pyr COOEt
7-718 3-CF_Three-Ph        4-Pyr COOPr
7-719 3-CF_Three-Ph        4-Pyr COO-i-Pr
7-720 3-CF_Three-Ph        4-Pyr COOBu
7-721 3-CF_Three-Ph        4-Pyr COOBn
7-722 3-CF_Three-Ph        4-Pyr COOPh
7-723 3-CF_Three-Ph        4-Pyr CONH₂              
7-724 3-CF_Three-Ph        4-Pyr CONHMe
7-725 3-CF_Three-Ph        4-Pyr CONHEt
7-726 3-CF_Three-Ph        4-Pyr CONHPr
7-727 3-CF_Three-Ph        4-Pyr CONH-i-Pr
7-728 3-CF_Three-Ph        4-Pyr CONHBu
7-729 3-CF_Three-Ph        4-Pyr CONHBn
7-730 3-CF_Three-Ph        4-Pyr CONMe₂             
7-731 3-CF_Three-Ph        4-Pyr CONH-c-Pr
7-732 3-CF_Three-Ph        4-Pyr CONH-c-Bu
7-733 3-CF_Three-Ph        4-Pyr CONH-c-Pen
7-734 3-CF_Three-Ph        4-Pyr CONH-c-Hex
7-735 3-CF_Three-Ph        4-Pyr CONH-c-Hep
7-736 3-CF_Three-Ph        4-Pyr CONHCH₂-c-Pr
7-737 3-CF_Three-Ph        4-Pyr CONH-Allyl
7-738 3-CF_Three-Ph        4-Pyr CONH-Propargyl
7-739 3-CF_Three-Ph        4-Pyr CONHPh
7-740 3-CF_Three-Ph        4-Pyr CONH-3-Pyr
7-741 3-CF_Three-Ph        4-Pyr CONHCH₂-4-Pyr
7-742 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-OH
7-743 3-CF_Three-Ph        4-Pyr CONHCH (CH₂OH)₂      
7-744 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-OAc
7-745 3-CF_Three-Ph        4-Pyr CONHCH₂CN
7-746 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-F
7-747 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-OMe
7-748 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-SMe
7-749 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-NH₂      
7-750 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-NHMe
7-751 3-CF_Three-Ph        4-Pyr CONH- (CH₂)₂-N (Me)₂   
7-752 3-CF_Three-Ph        4-Pyr CONHCH₂COOH
7-753 3-CF_Three-Ph        4-Pyr CONHCH₂COOEt
7-754 3-CF_Three-Ph        4-Pyr CONHCH (Me) COOEt
7-755 3-CF_Three-Ph        4-Pyr CONHCH₂CONH₂        
7-756 3-CF_Three-Ph        4-Pyr CONHOH
7-757 3-CF_Three-Ph        4-Pyr CONHOMe
7-758 3-CF_Three-Ph        4-Pyr CONHOEt
7-759 3-CF_Three-Ph        4-Pyr CONHOPr
7-760 3-CF_Three-Ph        4-Pyr CONHOAllyl
7-761 3-CF_Three-Ph        4-Pyr CONHOBn
7-762 3-CF_Three-Ph        4-Pyr CONHNH₂            
7-763 3-CF_Three-Ph        4-Pyr CONHNHMe
7-764 3-CF_Three-Ph        4-Pyr CONHN (Me)₂          
7-765 3-CF_Three-Ph        4-Pyr COMe
7-766 3-CF_Three-Ph        4-Pyr COEt
7-767 3-CF_Three-Ph        4-Pyr COPr
7-768 3-CF_Three-Ph        4-Pyr CO-i-Pr
7-769 3-CF_Three-Ph        4-Pyr COBu
7-770 3-CF_Three-Ph        4-Pyr COCF_Three              
7-771 3-CF_Three-Ph        4-Pyr CO- (CH₂)₂-F
7-772 3-CF_Three-Ph 4-Pyr CO- (CH₂)₂-OH
7-773 3-CF_Three-Ph        4-Pyr CO- (CH₂)₂-OMe
7-774 3-CF_Three-Ph        4-Pyr SOMe
7-775 3-CF_Three-Ph        4-Pyr SOEt
7-776 3-CF_Three-Ph        4-Pyr SOPr
7-777 3-CF_Three-Ph        4-Pyr SO-i-Pr
7-778 3-CF_Three-Ph        4-Pyr SOBu
7-779 3-CF_Three-Ph        4-Pyr SOCF_Three              
7-780 3-CF_Three-Ph        4-Pyr SO- (CH₂)₂-F         
7-781 3-CF_Three-Ph        4-Pyr SO- (CH₂)₂-OH        
7-782 3-CF_Three-Ph        4-Pyr SO- (CH₂)₂-OMe       
7-783 3-CF_Three-Ph        4-Pyr SO₂Me
7-784 3-CF_Three-Ph        4-Pyr SO₂Et
7-785 3-CF_Three-Ph        4-Pyr SO₂Pr
7-786 3-CF_Three-Ph        4-Pyr SO₂-i-Pr
7-787 3-CF_Three-Ph        4-Pyr SO₂Bu
7-788 3-CF_Three-Ph        4-Pyr SO₂CF_Three              
7-789 3-CF_Three-Ph        4-Pyr SO₂-(CH₂)₂-F
7-790 3-CF_Three-Ph        4-Pyr SO₂-(CH₂)₂-OH
7-791 3-CF_Three-Ph        4-Pyr SO₂-(CH₂)₂-OMe
7-792 3-CF_Three-Ph        4-Pyr SO₂NH₂              
7-793 3-CF_Three-Ph        4-Pyr SO₂NHMe
7-794 3-CF_Three-Ph        4-Pyr SO₂NHEt
7-795 3-CF_Three-Ph        4-Pyr SO₂NHPr
7-796 3-CF_Three-Ph        4-Pyr SO₂NH-i-Pr
7-797 3-CF_Three-Ph        4-Pyr SO₂NHBu
7-798 3-CF_Three-Ph        4-Pyr SO₂NHBn
7-799 3-CF_Three-Ph        4-Pyr SO₂NMe₂            
7-800 3-CF_Three-Ph        4-Pyr SO₂NH-c-Pr
7-801 3-CF_Three-Ph        4-Pyr SO₂NH-c-Bu
7-802 3-CF_Three-Ph        4-Pyr SO₂NH-c-Pen
7-803 3-CF_Three-Ph        4-Pyr SO₂NH-c-Hex
7-804 3-CF_Three-Ph        4-Pyr SO₂NH-c-Hep
7-805 3-CF_Three-Ph        4-Pyr SO₂NHCH₂-c-Pr
7-806 3-CF_Three-Ph        4-Pyr SO₂NH-Allyl
7-807 3-CF_Three-Ph        4-Pyr SO₂NH-Propargyl
7-808 3-CF_Three-Ph        4-Pyr SO₂NHPh
7-809 3-CF_Three-Ph        4-Pyr SO₂NH-3-Pyr
7-810 3-CF_Three-Ph        4-Pyr SO₂NHCH₂-4-Pyr
7-811 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-OH
7-812 3-CF_Three-Ph        4-Pyr SO₂NHCH (CH₂OH)₂      
7-813 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-OAc
7-814 3-CF_Three-Ph        4-Pyr SO₂NHCH₂CN
7-815 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-F
7-816 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-OMe
7-817 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-SMe
7-818 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-NH₂     
7-819 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-NHMe
7-820 3-CF_Three-Ph        4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
7-821 3-CF_Three-Ph        4-Pyr SO₂NHCH₂COOH
7-822 3-CF_Three-Ph        4-Pyr SO₂NHCH₂COOEt
7-823 3-CF_Three-Ph        4-Pyr SO₂NHCH (Me) COOEt
7-824 3-CF_Three-Ph        4-Pyr SO₂NHCH₂CONH₂        
7-825 3-CF_Three-Ph        4-Pyr SO₂NHOH
7-826 3-CF_Three-Ph        4-Pyr SO₂NHOMe
7-827 3-CF_Three-Ph        4-Pyr SO₂NHOEt
7-828 3-CF_Three-Ph        4-Pyr SO₂NHOPr
7-829 3-CF_Three-Ph        4-Pyr SO₂NHOAllyl
7-830 3-CF_Three-Ph        4-Pyr SO₂NHOBn
7-831 3-CF_Three-Ph        4-Pyr SO₂NHNH₂            
7-832 3-CF_Three-Ph        4-Pyr SO₂NHNHMe
7-833 3-CF_Three-Ph        4-Pyr SO₂NHN (Me)₂        
7-834 4-F-Ph 4-Pym CONH₂               
7-835 4-F-Ph 4-Pym CONHMe
7-836 4-F-Ph 4-Pym CONHEt
7-837 4-F-Ph 4-Pym CONHPr
7-838 4-F-Ph 4-Pym CONH-i-Pr
7-839 4-F-Ph 4-Pym CONHBu
7-840 4-F-Ph 4-Pym CONHBn
7-841 4-F-Ph 4-Pym CONMe₂              
7-842 4-F-Ph 4-Pym CONH-c-Pr
7-843 4-F-Ph 4-Pym CONH-c-Bu
7-844 4-F-Ph 4-Pym CONH-c-Pen
7-845 4-F-Ph 4-Pym CONH-c-Hex
7-846 4-F-Ph 4-Pym CONH-c-Hep
7-847 4-F-Ph 4-Pym CONHCH₂-c-Pr         
7-848 4-F-Ph 4-Pym CONH-Allyl
7-849 4-F-Ph 4-Pym CONH-Propargyl
7-850 4-F-Ph 4-Pym CONHPh
7-851 4-F-Ph 4-Pym CONH-3-Pyr
7-852 4-F-Ph 4-Pym CONHCH₂-4-Pyr        
7-853 4-F-Ph 4-Pym CONH- (CH₂)₂-OH
7-854 4-F-Ph 4-Pym CONHCH (CH₂OH)₂       
7-855 4-F-Ph 4-Pym CONH- (CH₂)₂-OAc
7-856 4-F-Ph 4-Pym CONHCH₂CN
7-857 4-F-Ph 4-Pym CONH- (CH₂)₂-F
7-858 4-F-Ph 4-Pym CONH- (CH₂)₂-OMe
7-859 4-F-Ph 4-Pym CONH- (CH₂)₂-SMe
7-860 4-F-Ph 4-Pym CONH- (CH₂)₂-NH₂     
7-861 4-F-Ph 4-Pym CONH- (CH₂)₂-NHMe
7-862 4-F-Ph 4-Pym CONH- (CH₂)₂-N (Me)₂  
7-863 4-F-Ph 4-Pym CONHCH₂COOH          
7-864 4-F-Ph 4-Pym CONHCH₂COOEt         
7-865 4-F-Ph 4-Pym CONHCH (Me) COOEt
7-866 4-F-Ph 4-Pym CONHCH₂CONH₂        
7-867 4-F-Ph 4-Pym SO₂NH₂              
7-868 4-F-Ph 4-Pym SO₂NHMe
7-869 4-F-Ph 4-Pym SO₂NHEt
7-870 4-F-Ph 4-Pym SO₂NHPr
7-871 4-F-Ph 4-Pym SO₂NH-i-Pr
7-872 4-F-Ph 4-Pym SO₂NHBu
7-873 4-F-Ph 4-Pym SO₂NHBn
7-874 4-F-Ph 4-Pym SO₂NMe₂             
7-875 4-F-Ph 4-Pym SO₂NH-c-Pr
7-876 4-F-Ph 4-Pym SO₂NH-c-Bu
7-877 4-F-Ph 4-Pym SO₂NH-c-Pen
7-878 4-F-Ph 4-Pym SO₂NH-c-Hex
7-879 4-F-Ph 4-Pym SO₂NH-c-Hep
7-880 4-F-Ph 4-Pym SO₂NHCH₂-c-Pr
7-881 4-F-Ph 4-Pym SO₂NH-Allyl
7-882 4-F-Ph 4-Pym SO₂NH-Propargyl
7-883 4-F-Ph 4-Pym SO₂NHPh
7-884 4-F-Ph 4-Pym SO₂NH-3-Pyr
7-885 4-F-Ph 4-Pym SO₂NHCH₂-4-Pyr
7-886 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OH
7-887 4-F-Ph 4-Pym SO₂NHCH (CH₂OH)₂      
7-888 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OAc
7-889 4-F-Ph 4-Pym SO₂NHCH₂CN
7-890 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-F
7-891 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OMe
7-892 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-SMe
7-893 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-NH₂     
7-894 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-NHMe
7-895 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
7-896 4-F-Ph 4-Pym SO₂NHCH₂COOH
7-897 4-F-Ph 4-Pym SO₂NHCH₂COOEt
7-898 4-F-Ph 4-Pym SO₂NHCH (Me) COOEt
7-899 4-F-Ph 4-Pym SO₂NHCH₂CONH₂        
7-900 4-F-Ph 4-Pym SO₂NHOH
7-901 4-F-Ph 4-Pym SO₂NHOMe
7-902 4-F-Ph 4-Pym SO₂NHOEt
7-903 4-F-Ph 4-Pym SO₂NHOPr
7-904 4-F-Ph 4-Pym SO₂NHOAllyl
7-905 4-F-Ph 4-Pym SO₂NHOBn
7-906 4-F-Ph 4-Pym SO₂NHNH₂            
7-907 4-F-Ph 4-Pym SO₂NHNHMe
7-908 4-F-Ph 4-Pym SO₂NHN (Me)₂         
7-909 4-F-Ph 2-MeO-4-Pym CONH₂              
7-910 4-F-Ph 2-MeO-4-Pym CONHMe
7-911 4-F-Ph 2-MeO-4-Pym CONHEt
7-912 4-F-Ph 2-MeO-4-Pym CONHPr
7-913 4-F-Ph 2-MeO-4-Pym CONH-i-Pr
7-914 4-F-Ph 2-MeO-4-Pym CONHBu
7-915 4-F-Ph 2-MeO-4-Pym CONHBn
7-916 4-F-Ph 2-MeO-4-Pym CONMe₂             
7-917 4-F-Ph 2-MeO-4-Pym CONH-c-Pr
7-918 4-F-Ph 2-MeO-4-Pym CONH-c-Bu
7-919 4-F-Ph 2-MeO-4-Pym CONH-c-Pen
7-920 4-F-Ph 2-MeO-4-Pym CONH-c-Hex
7-921 4-F-Ph 2-MeO-4-Pym CONH-c-Hep
7-922 4-F-Ph 2-MeO-4-Pym CONHCH₂-c-Pr
7-923 4-F-Ph 2-MeO-4-Pym CONH-Allyl
7-924 4-F-Ph 2-MeO-4-Pym CONH-Propargyl
7-925 4-F-Ph 2-MeO-4-Pym CONHPh
7-926 4-F-Ph 2-MeO-4-Pym CONH-3-Pyr
7-927 4-F-Ph 2-MeO-4-Pym CONHCH₂-4-Pyr
7-928 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OH
7-929 4-F-Ph 2-MeO-4-Pym CONHCH (CH₂OH)₂       
7-930 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OAc
7-931 4-F-Ph 2-MeO-4-Pym CONHCH₂CN            
7-932 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-F
7-933 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OMe
7-934 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-SMe
7-935 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-NH₂      
7-936 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-NHMe
7-937 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-N (Me)₂   
7-938 4-F-Ph 2-MeO-4-Pym CONHCH₂COOH          
7-939 4-F-Ph 2-MeO-4-Pym CONHCH₂COOEt         
7-940 4-F-Ph 2-MeO-4-Pym CONHCH (Me) COOEt
7-941 4-F-Ph 2-MeO-4-Pym CONHCH₂CONH₂        
7-942 4-F-Ph 2-MeO-4-Pym SO₂NH₂              
7-943 4-F-Ph 2-MeO-4-Pym SO₂NHMe             
7-944 4-F-Ph 2-MeO-4-Pym SO₂NHEt             
7-945 4-F-Ph 2-MeO-4-Pym SO₂NHPr             
7-946 4-F-Ph 2-MeO-4-Pym SO₂NH-i-Pr          
7-947 4-F-Ph 2-MeO-4-Pym SO₂NHBu             
7-948 4-F-Ph 2-MeO-4-Pym SO₂NHBn             
7-949 4-F-Ph 2-MeO-4-Pym SO₂NMe₂             
7-950 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Pr          
7-951 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Bu
7-952 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Pen
7-953 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Hex
7-954 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Hep
7-955 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂-c-Pr
7-956 4-F-Ph 2-MeO-4-Pym SO₂NH-Allyl          
7-957 4-F-Ph 2-MeO-4-Pym SO₂NH-Propargyl
7-958 4-F-Ph 2-MeO-4-Pym SO₂NHPh              
7-959 4-F-Ph 2-MeO-4-Pym SO₂NH-3-Pyr          
7-960 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂-4-Pyr
7-961 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OH
7-962 4-F-Ph 2-MeO-4-Pym SO₂NHCH (CH₂OH)₂     
7-963 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OAc
7-964 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂CN
7-965 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-F
7-966 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OMe
7-967 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-SMe
7-968 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-NH₂     
7-969 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-NHMe
7-970 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
7-971 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂COOH
7-972 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂COOEt
7-973 4-F-Ph 2-MeO-4-Pym SO₂NHCH (Me) COOEt     
7-974 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂CONH₂       
7-975 4-F-Ph 2-MeO-4-Pym SO₂NHOH             
7-976 4-F-Ph 2-MeO-4-Pym SO₂NHOMe
7-977 4-F-Ph 2-MeO-4-Pym SO₂NHOEt
7-978 4-F-Ph 2-MeO-4-Pym SO₂NHOPr
7-979 4-F-Ph 2-MeO-4-Pym SO₂NHOAllyl
7-980 4-F-Ph 2-MeO-4-Pym SO₂NHOBn
7-981 4-F-Ph 2-MeO-4-Pym SO₂NHNH₂            
7-982 4-F-Ph 2-MeO-4-Pym SO₂NHNHMe
7-983 4-F-Ph 2-MeO-4-Pym SO₂NHN (Me)₂         
7-984 4-F-Ph 2-NH₂-4-Pym CONH₂              
7-985 4-F-Ph 2-NH₂-4-Pym CONHMe
7-986 4-F-Ph 2-NH₂-4-Pym CONHEt
7-987 4-F-Ph 2-NH₂-4-Pym CONHPr
7-988 4-F-Ph 2-NH₂-4-Pym CONH-i-Pr
7-989 4-F-Ph 2-NH₂-4-Pym CONHBu
7-990 4-F-Ph 2-NH₂-4-Pym CONHBn
7-991 4-F-Ph 2-NH₂-4-Pym CONMe₂             
7-992 4-F-Ph 2-NH₂-4-Pym CONH-c-Pr
7-993 4-F-Ph 2-NH₂-4-Pym CONH-c-Bu
7-994 4-F-Ph 2-NH₂-4-Pym CONH-c-Pen
7-995 4-F-Ph 2-NH₂-4-Pym CONH-c-Hex
7-996 4-F-Ph 2-NH₂-4-Pym CONH-c-Hep
7-997 4-F-Ph 2-NH₂-4-Pym CONHCH₂-c-Pr
7-998 4-F-Ph 2-NH₂-4-Pym CONH-Allyl
7-999 4-F-Ph 2-NH₂-4-Pym CONH-Propargyl
7-1000 4-F-Ph 2-NH₂-4-Pym CONHPh
7-1001 4-F-Ph 2-NH₂-4-Pym CONH-3-Pyr
7-1002 4-F-Ph 2-NH₂-4-Pym CONHCH₂-4-Pyr
7-1003 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OH
7-1004 4-F-Ph 2-NH₂-4-Pym CONHCH (CH₂OH)₂      
7-1005 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OAc
7-1006 4-F-Ph 2-NH₂-4-Pym CONHCH₂CN
7-1007 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-F
7-1008 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OMe
7-1009 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-SMe
7-1010 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-NH₂      
7-1011 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-NHMe
7-1012 4-F-Ph 2-NH₂-4-Pym        CONH- (CH₂)₂-N (Me)₂   
7-1013 4-F-Ph 2-NH₂-4-Pym CONHCH₂COOH
7-1014 4-F-Ph 2-NH₂-4-Pym CONHCH₂COOEt
7-1015 4-F-Ph 2-NH₂-4-Pym CONHCH (Me) COOEt     
7-1016 4-F-Ph 2-NH₂-4-Pym        CONHCH₂CONH₂        
7-1017 4-F-Ph 2-NH₂-4-Pym SO₂NH₂             
7-1018 4-F-Ph 2-NH₂-4-Pym SO₂NHMe
7-1019 4-F-Ph 2-NH₂-4-Pym SO₂NHEt
7-1020 4-F-Ph 2-NH₂-4-Pym SO₂NHPr
7-1021 4-F-Ph 2-NH₂-4-Pym SO₂NH-i-Pr
7-1022 4-F-Ph 2-NH₂-4-Pym SO₂NHBu
7-1023 4-F-Ph 2-NH₂-4-Pym SO₂NHBn
7-1024 4-F-Ph 2-NH₂-4-Pym SO₂NMe₂            
7-1025 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Pr
7-1026 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Bu
7-1027 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Pen
7-1028 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Hex
7-1029 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Hep
7-1030 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂-c-Pr
7-1031 4-F-Ph 2-NH₂-4-Pym SO₂NH-Allyl
7-1032 4-F-Ph 2-NH₂-4-Pym SO₂NH-Propargyl
7-1033 4-F-Ph 2-NH₂-4-Pym SO₂NHPh
7-1034 4-F-Ph 2-NH₂-4-Pym SO₂NH-3-Pyr
7-1035 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂-4-Pyr
7-1036 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OH
7-1037 4-F-Ph 2-NH₂-4-Pym SO₂NHCH (CH₂OH)₂      
7-1038 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OAc
7-1039 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂CN
7-1040 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-F
7-1041 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OMe
7-1042 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-SMe
7-1043 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-NH₂     
7-1044 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-NHMe
7-1045 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
7-1046 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂COOH
7-1047 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂COOEt
7-1048 4-F-Ph 2-NH₂-4-Pym SO₂NHCH (Me) COOEt
7-1049 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂CONH₂        
7-1050 4-F-Ph 2-NH₂-4-Pym SO₂NHOH
7-1051 4-F-Ph 2-NH₂-4-Pym SO₂NHOMe
7-1052 4-F-Ph 2-NH₂-4-Pym SO₂NHOEt
7-1053 4-F-Ph 2-NH₂-4-Pym SO₂NHOPr
7-1054 4-F-Ph 2-NH₂-4-Pym SO₂NHOAllyl
7-1055 4-F-Ph 2-NH₂-4-Pym SO₂NHOBn
7-1056 4-F-Ph 2-NH₂-4-Pym SO₂NHNH₂            
7-1057 4-F-Ph 2-NH₂-4-Pym SO₂NHNHMe           
7-1058 4-F-Ph 2-NH₂-4-Pym SO₂NHN (Me)₂        
7-1059 4-F-Ph 2-MeNH-4-Pym CONH₂              
7-1060 4-F-Ph 2-MeNH-4-Pym CONHMe
7-1061 4-F-Ph 2-MeNH-4-Pym CONHEt
7-1062 4-F-Ph 2-MeNH-4-Pym CONHPr
7-1063 4-F-Ph 2-MeNH-4-Pym CONH-i-Pr
7-1064 4-F-Ph 2-MeNH-4-Pym CONHBu
7-1065 4-F-Ph 2-MeNH-4-Pym CONHBn
7-1066 4-F-Ph 2-MeNH-4-Pym CONMe₂              
7-1067 4-F-Ph 2-MeNH-4-Pym CONH-c-Pr
7-1068 4-F-Ph 2-MeNH-4-Pym CONH-c-Bu
7-1069 4-F-Ph 2-MeNH-4-Pym CONH-c-Pen
7-1070 4-F-Ph 2-MeNH-4-Pym CONH-c-Hex
7-1071 4-F-Ph 2-MeNH-4-Pym CONH-c-Hep
7-1072 4-F-Ph 2-MeNH-4-Pym CONHCH₂-c-Pr
7-1073 4-F-Ph 2-MeNH-4-Pym CONH-Allyl
7-1074 4-F-Ph 2-MeNH-4-Pym CONH-Propargyl
7-1075 4-F-Ph 2-MeNH-4-Pym CONHPh
7-1076 4-F-Ph 2-MeNH-4-Pym CONH-3-Pyr
7-1077 4-F-Ph 2-MeNH-4-Pym CONHCH₂-4-Pyr
7-1078 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OH
7-1079 4-F-Ph 2-MeNH-4-Pym CONHCH (CH₂OH)₂       
7-1080 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OAc
7-1081 4-F-Ph 2-MeNH-4-Pym CONHCH₂CN
7-1082 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-F
7-1083 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OMe
7-1084 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-SMe
7-1085 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-NH₂      
7-1086 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-NHMe
7-1087 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-N (Me)₂   
7-1088 4-F-Ph 2-MeNH-4-Pym CONHCH₂COOH
7-1089 4-F-Ph 2-MeNH-4-Pym CONHCH₂COOEt
7-1090 4-F-Ph 2-MeNH-4-Pym CONHCH (Me) COOEt
7-1091 4-F-Ph 2-MeNH-4-Pym CONHCH₂CONH₂        
7-1092 4-F-Ph 2-MeNH-4-Pym SO₂NH₂              
7-1093 4-F-Ph 2-MeNH-4-Pym SO₂NHMe
7-1094 4-F-Ph 2-MeNH-4-Pym SO₂NHEt
7-1095 4-F-Ph 2-MeNH-4-Pym SO₂NHPr
7-1096 4-F-Ph 2-MeNH-4-Pym SO₂NH-i-Pr
7-1097 4-F-Ph 2-MeNH-4-Pym SO₂NHBu
7-1098 4-F-Ph 2-MeNH-4-Pym SO₂NHBn
7-1099 4-F-Ph 2-MeNH-4-Pym SO₂NMe₂             
7-1100 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Pr
7-1101 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Bu
7-1102 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Pen
7-1103 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Hex
7-1104 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Hep
7-1105 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂-c-Pr        
7-1106 4-F-Ph 2-MeNH-4-Pym SO₂NH-Allyl
7-1107 4-F-Ph 2-MeNH-4-Pym SO₂NH-Propargyl
7-1108 4-F-Ph 2-MeNH-4-Pym SO₂NHPh
7-1109 4-F-Ph 2-MeNH-4-Pym SO₂NH-3-Pyr
7-1110 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂-4-Pyr
7-1111 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OH      
7-1112 4-F-Ph 2-MeNH-4-Pym SO₂NHCH (CH₂OH)₂     
7-1113 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OAc     
7-1114 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂CN           
7-1115 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-F       
7-1116 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OMe     
7-1117 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-SMe     
7-1118 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-NH₂     
7-1119 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-NHMe    
7-1120 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
7-1121 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂COOH        
7-1122 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂COOEt       
7-1123 4-F-Ph 2-MeNH-4-Pym SO₂NHCH (Me) COOEt    
7-1124 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂CONH₂       
7-1125 4-F-Ph 2-MeNH-4-Pym SO₂NHOH
7-1126 4-F-Ph 2-MeNH-4-Pym SO₂NHOMe
7-1127 4-F-Ph 2-MeNH-4-Pym SO₂NHOEt
7-1128 4-F-Ph 2-MeNH-4-Pym SO₂NHOPr
7-1129 4-F-Ph 2-MeNH-4-Pym SO₂NHOAllyl
7-1130 4-F-Ph 2-MeNH-4-Pym SO₂NHOBn
7-1131 4-F-Ph 2-MeNH-4-Pym SO₂NHNH₂            
7-1132 4-F-Ph 2-MeNH-4-Pym SO₂NHNHMe
7-1133 4-F-Ph 2-MeNH-4-Pym SO₂NHN (Me)₂         
7-1134 4-F-Ph 2-BnNH-4-Pym CONH₂               
7-1135 4-F-Ph 2-BnNH-4-Pym CONHMe
7-1136 4-F-Ph 2-BnNH-4-Pym CONHEt
7-1137 4-F-Ph 2-BnNH-4-Pym CONHPr
7-1138 4-F-Ph 2-BnNH-4-Pym CONH-i-Pr
7-1139 4-F-Ph 2-BnNH-4-Pym CONHBu
7-1140 4-F-Ph 2-BnNH-4-Pym CONHBn
7-1141 4-F-Ph 2-BnNH-4-Pym CONMe₂             
7-1142 4-F-Ph 2-BnNH-4-Pym CONH-c-Pr
7-1143 4-F-Ph 2-BnNH-4-Pym CONH-c-Bu
7-1144 4-F-Ph 2-BnNH-4-Pym CONH-c-Pen
7-1145 4-F-Ph 2-BnNH-4-Pym CONH-c-Hex
7-1146 4-F-Ph 2-BnNH-4-Pym CONH-c-Hep
7-1147 4-F-Ph 2-BnNH-4-Pym CONHCH₂-c-Pr
7-1148 4-F-Ph 2-BnNH-4-Pym CONH-Allyl
7-1149 4-F-Ph 2-BnNH-4-Pym CONH-Propargyl
7-1150 4-F-Ph 2-BnNH-4-Pym CONHPh
7-1151 4-F-Ph 2-BnNH-4-Pym CONH-3-Pyr
7-1152 4-F-Ph 2-BnNH-4-Pym CONHCH₂-4-Pyr
7-1153 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OH
7-1154 4-F-Ph 2-BnNH-4-Pym CONHCH (CH₂OH)₂       
7-1155 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OAc
7-1156 4-F-Ph 2-BnNH-4-Pym CONHCH₂CN            
7-1157 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-F
7-1158 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OMe
7-1159 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-SMe
7-1160 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-NH₂      
7-1161 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-NHMe
7-1162 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-N (Me)₂  
7-1163 4-F-Ph 2-BnNH-4-Pym CONHCH₂COOH          
7-1164 4-F-Ph 2-BnNH-4-Pym CONHCH₂COOEt         
7-1165 4-F-Ph 2-BnNH-4-Pym CONHCH (Me) COOEt
7-1166 4-F-Ph 2-BnNH-4-Pym CONHCH₂CONH₂        
7-1167 4-F-Ph 2-BnNH-4-Pym SO₂NH₂              
7-1168 4-F-Ph 2-BnNH-4-Pym SO₂NHMe
7-1169 4-F-Ph 2-BnNH-4-Pym SO₂NHEt
7-1170 4-F-Ph 2-BnNH-4-Pym SO₂NHPr
7-1171 4-F-Ph 2-BnNH-4-Pym SO₂NH-i-Pr
7-1172 4-F-Ph 2-BnNH-4-Pym SO₂NHBu
7-1173 4-F-Ph 2-BnNH-4-Pym SO₂NHBn
7-1174 4-F-Ph 2-BnNH-4-Pym SO₂NMe₂             
7-1175 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Pr
7-1176 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Bu
7-1177 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Pen
7-1178 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Hex
7-1179 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Hep
7-1180 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂-c-Pr
7-1181 4-F-Ph 2-BnNH-4-Pym SO₂NH-Allyl
7-1182 4-F-Ph 2-BnNH-4-Pym SO₂NH-Propargyl
7-1183 4-F-Ph 2-BnNH-4-Pym SO₂NHPh
7-1184 4-F-Ph 2-BnNH-4-Pym SO₂NH-3-Pyr
7-1185 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂-4-Pyr
7-1186 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OH
7-1187 4-F-Ph 2-BnNH-4-Pym SO₂NHCH (CH₂OH)₂      
7-1188 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OAc
7-1189 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂CN
7-1190 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-F
7-1191 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OMe
7-1192 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-SMe
7-1193 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-NH₂     
7-1194 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-NHMe
7-1195 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
7-1196 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂COOH
7-1197 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂COOEt
7-1198 4-F-Ph 2-BnNH-4-Pym SO₂NHCH (Me) COOEt     
7-1199 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂CONH₂       
7-1200 4-F-Ph 2-BnNH-4-Pym SO₂NHOH
7-1201 4-F-Ph 2-BnNH-4-Pym SO₂NHOMe
7-1202 4-F-Ph 2-BnNH-4-Pym SO₂NHOEt
7-1203 4-F-Ph 2-BnNH-4-Pym SO₂NHOPr
7-1204 4-F-Ph 2-BnNH-4-Pym SO₂NHOAllyl
7-1205 4-F-Ph 2-BnNH-4-Pym SO₂NHOBn
7-1206 4-F-Ph 2-BnNH-4-Pym SO₂NHNH₂            
7-1207 4-F-Ph 2-BnNH-4-Pym SO₂NHNHMe
7-1208 4-F-Ph 2-BnNH-4-Pym SO₂NHN (Me)₂          
7-1209 4-F-Ph (α-Me-BnNH) -4-Pym CONH₂              
7-1210 4-F-Ph (α-Me-BnNH) -4-Pym CONHMe
7-1211 4-F-Ph (α-Me-BnNH) -4-Pym CONHEt
7-1212 4-F-Ph (α-Me-BnNH) -4-Pym CONHPr
7-1213 4-F-Ph (α-Me-BnNH) -4-Pym CONH-i-Pr
7-1214 4-F-Ph (α-Me-BnNH) -4-Pym CONHBu
7-1215 4-F-Ph (α-Me-BnNH) -4-Pym CONHBn
7-1216 4-F-Ph (α-Me-BnNH) -4-Pym CONMe₂             
7-1217 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Pr
7-1218 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Bu
7-1219 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Pen
7-1220 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Hex
7-1221 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Hep
7-1222 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂-c-Pr
7-1223 4-F-Ph (α-Me-BnNH) -4-Pym CONH-Allyl
7-1224 4-F-Ph (α-Me-BnNH) -4-Pym CONH-Propargyl
7-1225 4-F-Ph (α-Me-BnNH) -4-Pym CONHPh
7-1226 4-F-Ph (α-Me-BnNH) -4-Pym CONH-3-Pyr
7-1227 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂-4-Pyr        
7-1228 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OH
7-1229 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH (CH₂OH)₂       
7-1230 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OAc
7-1231 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂CN            
7-1232 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-F
7-1233 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OMe
7-1234 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-SMe
7-1235 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-NH₂      
7-1236 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-NHMe
7-1237 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-N (Me)₂  
7-1238 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂COOH
7-1239 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂COOEt
7-1240 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH (Me) COOEt
7-1241 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂CONH₂        
7-1242 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH₂              
7-1243 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHMe
7-1244 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHEt
7-1245 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHPr
7-1246 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-i-Pr
7-1247 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHBu
7-1248 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHBn
7-1249 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NMe₂             
7-1250 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Pr
7-1251 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Bu
7-1252 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Pen
7-1253 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Hex
7-1254 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Hep
7-1255 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂-c-Pr
7-1256 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-Allyl
7-1257 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-Propargyl
7-1258 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHPh
7-1259 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-3-Pyr
7-1260 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂-4-Pyr
7-1261 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OH
7-1262 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH (CH₂OH)₂      
7-1263 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OAc
7-1264 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂CN
7-1265 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-F
7-1266 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OMe
7-1267 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-SMe
7-1268 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-NH₂     
7-1269 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-NHMe
7-1270 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
7-1271 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂COOH
7-1272 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂COOEt
7-1273 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH (Me) COOEt
7-1274 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂CONH₂        
7-1275 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOH
7-1276 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOMe
7-1277 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOEt
7-1278 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOPr
7-1279 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOAllyl
7-1280 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOBn
7-1281 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHNH₂            
7-1282 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHNHMe           
7-1283 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHN (Me)₂          
7-1284 4-F-Ph 4-Pyr SO₂NHMe               
7-1285 4-F-Ph 4-Pyr SOMe                  
7-1286 4-F-Ph 4-Pyr SO₂Me                 
7-1287 3-Cl-4-F-Ph 4-Pyr SO₂NHMe               
7-1288 3-Cl-4-F-Ph 4-Pyr SOMe                  
7-1289 3-Cl-4-F-Ph 4-Pyr SO₂Me                 
―――――――――――――――――――――――――――――――
Table 8

―――――――――――――――――――――――――――
Compound R ¹ R ⁴ R ⁴ 'R ⁵
No .――――――――――――――――――――――――――――
8-1 4-F-Ph Me H CONH ₂
8-2 4-F-Ph Me H CONHMe
8-3 4-F-Ph Me H CONHEt
8-4 4-F-Ph Me H CONHPr
8-5 4-F-Ph Me H CONH-i-Pr
8-6 4-F-Ph Me H CONHBu
8-7 4-F-Ph Me H SO ₂ NH ₂
8-8 4-F-Ph Me H SO ₂ NHMe
8-9 4-F-Ph Me H SO ₂ NHEt
8-10 4-F-Ph Me H SO ₂ NHPr
8-11 4-F-Ph Me H SO ₂ NH-i-Pr
8-12 4-F-Ph Me H SO ₂ NHBu
8-13 4-F-Ph Me H SOMe
8-14 4-F-Ph Me H SOEt
8-15 4-F-Ph Me H SOPr
8-16 4-F-Ph Me H SO ₂ Me
8-17 4-F-Ph Me H SO ₂ Et
8-18 4-F-Ph Me H SO ₂ Pr
8-19 4-F-Ph Me H COMe
8-20 4-F-Ph Me H COEt
8-21 4-F-Ph Me H COPr
8-22 4-F-Ph H Me CONH ₂
8-23 4-F-Ph H Me CONHMe
8-24 4-F-Ph H Me CONHEt
8-25 4-F-Ph H Me CONHPr
8-26 4-F-Ph H Me CONH-i-Pr
8-27 4-F-Ph H Me CONHBu
8-28 4-F-Ph H Me SO ₂ NH ₂
8-29 4-F-Ph H Me SO ₂ NHMe
8-30 4-F-Ph H Me SO ₂ NHEt
8-31 4-F-Ph H Me SO ₂ NHPr
8-32 4-F-Ph H Me SO ₂ NH-i-Pr
8-33 4-F-Ph H Me SO ₂ NHBu
8-34 4-F-Ph H Me SOMe
8-35 4-F-Ph H Me SOEt
8-36 4-F-Ph H Me SOPr
8-37 4-F-Ph H Me SO ₂ Me
8-38 4-F-Ph H Me SO ₂ Et
8-39 4-F-Ph H Me SO ₂ Pr
8-40 4-F-Ph H Me COMe
8-41 4-F-Ph H Me COEt
8-42 4-F-Ph H Me COPr
8-43 4-F-Ph Me Me CONH ₂
8-44 4-F-Ph Me Me CONHMe
8-45 4-F-Ph Me Me CONHEt
8-46 4-F-Ph Me Me CONHPr
8-47 4-F-Ph Me Me CONH-i-Pr
8-48 4-F-Ph Me Me CONHBu
8-49 4-F-Ph Me Me SO ₂ NH ₂
8-50 4-F-Ph Me Me SO ₂ NHMe
8-51 4-F-Ph Me Me SO ₂ NHEt
8-52 4-F-Ph Me Me SO ₂ NHPr
8-53 4-F-Ph Me Me SO ₂ NH-i-Pr
8-54 4-F-Ph Me Me SO ₂ NHBu
8-55 4-F-Ph Me Me SOMe
8-56 4-F-Ph Me Me SOEt
8-57 4-F-Ph Me Me SOPr
8-58 4-F-Ph Me Me SO ₂ Me
8-59 4-F-Ph Me Me SO ₂ Et
8-60 4-F-Ph Me Me SO ₂ Pr
8-61 4-F-Ph Me Me COMe
8-62 4-F-Ph Me Me COEt
8-63 4-F-Ph Me Me COPr
―――――――――――――――――――――――――――
Table 9

―――――――――――――――――――――――――
Compound R ¹ ZR ⁵
No .――――――――――――――――――――――――――
9-1 4-F-Ph Ring 1 CONH ₂
9-2 4-F-Ph Ring 1 CONHMe
9-3 4-F-Ph Ring 1 CONHEt
9-4 4-F-Ph Ring 1 CONHPr
9-5 4-F-Ph Ring 1 CONH-i-Pr
9-6 4-F-Ph Ring 1 CONHBu
9-7 4-F-Ph Ring 1 SO ₂ NH ₂
9-8 4-F-Ph Ring 1 SO ₂ NHMe
9-9 4-F-Ph Ring 1 SO ₂ NHEt
9-10 4-F-Ph Ring 1 SO ₂ NHPr
9-11 4-F-Ph Ring 1 SO ₂ NH-i-Pr
9-12 4-F-Ph Ring 1 SO ₂ NHBu
9-13 4-F-Ph Ring 1 SOMe
9-14 4-F-Ph Ring 1 SOEt
9-15 4-F-Ph Ring 1 SOPr
9-16 4-F-Ph Ring 1 SO ₂ Me
9-17 4-F-Ph Ring 1 SO ₂ Et
9-18 4-F-Ph Ring 1 SO ₂ Pr
9-19 4-F-Ph Ring 1 COMe
9-20 4-F-Ph Ring 1 COEt
9-21 4-F-Ph Ring 1 COPr
9-22 3-Cl-4-F-Ph Ring 1 CONH ₂
9-23 3-Cl-4-F-Ph Ring 1 CONHMe
9-24 3-Cl-4-F-Ph Ring 1 CONHEt
9-25 3-Cl-4-F-Ph Ring 1 CONHPr
9-26 3-Cl-4-F-Ph Ring 1 CONH-i-Pr
9-27 3-Cl-4-F-Ph Ring 1 CONHBu
9-28 3-Cl-4-F-Ph Ring 1 SO ₂ NH ₂
9-29 3-Cl-4-F-Ph Ring 1 SO ₂ NHMe
9-30 3-Cl-4-F-Ph Ring 1 SO ₂ NHEt
9-31 3-Cl-4-F-Ph Ring 1 SO ₂ NHPr
9-32 3-Cl-4-F-Ph Ring 1 SO ₂ NH-i-Pr
9-33 3-Cl-4-F-Ph Ring 1 SO ₂ NHBu
9-34 3-Cl-4-F-Ph Ring 1 SOMe
9-35 3-Cl-4-F-Ph Ring 1 SOEt
9-36 3-Cl-4-F-Ph Ring 1 SOPr
9-37 3-Cl-4-F-Ph Ring 1 SO ₂ Me
9-38 3-Cl-4-F-Ph Ring 1 SO ₂ Et
9-39 3-Cl-4-F-Ph Ring 1 SO ₂ Pr
9-40 3-Cl-4-F-Ph Ring 1 COMe
9-41 3-Cl-4-F-Ph Ring 1 COEt
9-42 3-Cl-4-F-Ph Ring 1 COPr
9-43 4-F-Ph Ring 2 CONH ₂
9-44 4-F-Ph Ring 2 CONHMe
9-45 4-F-Ph Ring 2 CONHEt
9-46 4-F-Ph Ring 2 CONHPr
9-47 4-F-Ph Ring 2 CONH-i-Pr
9-48 4-F-Ph Ring 2 CONHBu
9-49 4-F-Ph Ring 2 SO ₂ NH ₂
9-50 4-F-Ph Ring 2 SO ₂ NHMe
9-51 4-F-Ph Ring 2 SO ₂ NHEt
9-52 4-F-Ph Ring 2 SO ₂ NHPr
9-53 4-F-Ph Ring 2 SO ₂ NH-i-Pr
9-54 4-F-Ph Ring 2 SO ₂ NHBu
9-55 4-F-Ph Ring 2 SOMe
9-56 4-F-Ph Ring 2 SOEt
9-57 4-F-Ph Ring 2 SOPr
9-58 4-F-Ph Ring 2 SO ₂ Me
9-59 4-F-Ph Ring 2 SO ₂ Et
9-60 4-F-Ph Ring 2 SO ₂ Pr
9-61 4-F-Ph Ring 2 COMe
9-62 4-F-Ph Ring 2 COEt
9-63 4-F-Ph Ring 2 COPr
9-64 3-Cl-4-F-Ph Ring 2 CONH ₂
9-65 3-Cl-4-F-Ph Ring 2 CONHMe
9-66 3-Cl-4-F-Ph Ring 2 CONHEt
9-67 3-Cl-4-F-Ph Ring 2 CONHPr
9-68 3-Cl-4-F-Ph Ring 2 CONH-i-Pr
9-69 3-Cl-4-F-Ph Ring 2 CONHBu
9-70 3-Cl-4-F-Ph Ring 2 SO ₂ NH ₂
9-71 3-Cl-4-F-Ph Ring 2 SO ₂ NHMe
9-72 3-Cl-4-F-Ph Ring 2 SO ₂ NHEt
9-73 3-Cl-4-F-Ph Ring 2 SO ₂ NHPr
9-74 3-Cl-4-F-Ph Ring 2 SO ₂ NH-i-Pr
9-75 3-Cl-4-F-Ph Ring 2 SO ₂ NHBu
9-76 3-Cl-4-F-Ph Ring 2 SOMe
9-77 3-Cl-4-F-Ph Ring 2 SOEt
9-78 3-Cl-4-F-Ph Ring 2 SOPr
9-79 3-Cl-4-F-Ph Ring 2 SO ₂ Me
9-80 3-Cl-4-F-Ph Ring 2 SO ₂ Et
9-81 3-Cl-4-F-Ph Ring 2 SO ₂ Pr
9-82 3-Cl-4-F-Ph Ring 2 COMe
9-83 3-Cl-4-F-Ph Ring 2 COEt
9-84 3-Cl-4-F-Ph Ring 2 COPr
9-85 4-F-Ph Ring 3 CONH ₂
9-86 4-F-Ph Ring 3 CONHMe
9-87 4-F-Ph Ring 3 CONHEt
9-88 4-F-Ph Ring 3 CONHPr
9-89 4-F-Ph Ring 3 CONH-i-Pr
9-90 4-F-Ph Ring 3 CONHBu
9-91 4-F-Ph Ring 3 SO ₂ NH ₂
9-92 4-F-Ph Ring 3 SO ₂ NHMe
9-93 4-F-Ph Ring 3 SO ₂ NHEt
9-94 4-F-Ph Ring 3 SO ₂ NHPr
9-95 4-F-Ph Ring 3 SO ₂ NH-i-Pr
9-96 4-F-Ph Ring 3 SO ₂ NHBu
9-97 4-F-Ph Ring 3 SOMe
9-98 4-F-Ph Ring 3 SOEt
9-99 4-F-Ph Ring 3 SOPr
9-100 4-F-Ph Ring 3 SO ₂ Me
9-101 4-F-Ph Ring 3 SO ₂ Et
9-102 4-F-Ph Ring 3 SO ₂ Pr
9-103 4-F-Ph Ring 3 COMe
9-104 4-F-Ph Ring 3 COEt
9-105 4-F-Ph Ring 3 COPr
9-106 3-Cl-4-F-Ph Ring 3 CONH ₂
9-107 3-Cl-4-F-Ph Ring 3 CONHMe
9-108 3-Cl-4-F-Ph Ring 3 CONHEt
9-109 3-Cl-4-F-Ph Ring 3 CONHPr
9-110 3-Cl-4-F-Ph Ring 3 CONH-i-Pr
9-111 3-Cl-4-F-Ph Ring 3 CONHBu
9-112 3-Cl-4-F-Ph Ring 3 SO ₂ NH ₂
9-113 3-Cl-4-F-Ph Ring 3 SO ₂ NHMe
9-114 3-Cl-4-F-Ph Ring 3 SO ₂ NHEt
9-115 3-Cl-4-F-Ph Ring 3 SO ₂ NHPr
9-116 3-Cl-4-F-Ph Ring 3 SO ₂ NH-i-Pr
9-117 3-Cl-4-F-Ph Ring 3 SO ₂ NHBu
9-118 3-Cl-4-F-Ph Ring 3 SOMe
9-119 3-Cl-4-F-Ph Ring 3 SOEt
9-120 3-Cl-4-F-Ph Ring 3 SOPr
9-121 3-Cl-4-F-Ph Ring 3 SO ₂ Me
9-122 3-Cl-4-F-Ph Ring 3 SO ₂ Et
9-123 3-Cl-4-F-Ph Ring 3 SO ₂ Pr
9-124 3-Cl-4-F-Ph Ring 3 COMe
9-125 3-Cl-4-F-Ph Ring 3 COEt
9-126 3-Cl-4-F-Ph Ring 3 COPr
9-127 4-F-Ph Ring 4 CONH ₂
9-128 4-F-Ph Ring 4 CONHMe
9-129 4-F-Ph Ring 4 CONHEt
9-130 4-F-Ph Ring 4 CONHPr
9-131 4-F-Ph Ring 4 CONH-i-Pr
9-132 4-F-Ph Ring 4 CONHBu
9-133 4-F-Ph Ring 4 SO ₂ NH ₂
9-134 4-F-Ph Ring 4 SO ₂ NHMe
9-135 4-F-Ph Ring 4 SO ₂ NHEt
9-136 4-F-Ph Ring 4 SO ₂ NHPr
9-137 4-F-Ph Ring 4 SO ₂ NH-i-Pr
9-138 4-F-Ph Ring 4 SO ₂ NHBu
9-139 4-F-Ph Ring 4 SOMe
9-140 4-F-Ph Ring 4 SOEt
9-141 4-F-Ph Ring 4 SOPr
9-142 4-F-Ph Ring 4 SO ₂ Me
9-143 4-F-Ph Ring 4 SO ₂ Et
9-144 4-F-Ph Ring 4 SO ₂ Pr
9-145 4-F-Ph Ring 4 COMe
9-146 4-F-Ph Ring 4 COEt
9-147 4-F-Ph Ring 4 COPr
9-148 3-Cl-4-F-Ph Ring 4 CONH ₂
9-149 3-Cl-4-F-Ph Ring 4 CONHMe
9-150 3-Cl-4-F-Ph Ring 4 CONHEt
9-151 3-Cl-4-F-Ph Ring 4 CONHPr
9-152 3-Cl-4-F-Ph Ring 4 CONH-i-Pr
9-153 3-Cl-4-F-Ph Ring 4 CONHBu
9-154 3-Cl-4-F-Ph Ring 4 SO ₂ NH ₂
9-155 3-Cl-4-F-Ph Ring 4 SO ₂ NHMe
9-156 3-Cl-4-F-Ph Ring 4 SO ₂ NHEt
9-157 3-Cl-4-F-Ph Ring 4 SO ₂ NHPr
9-158 3-Cl-4-F-Ph Ring 4 SO ₂ NH-i-Pr
9-159 3-Cl-4-F-Ph Ring 4 SO ₂ NHBu
9-160 3-Cl-4-F-Ph Ring 4 SOMe
9-161 3-Cl-4-F-Ph Ring 4 SOEt
9-162 3-Cl-4-F-Ph Ring 4 SOPr
9-163 3-Cl-4-F-Ph Ring 4 SO ₂ Me
9-164 3-Cl-4-F-Ph Ring 4 SO ₂ Et
9-165 3-Cl-4-F-Ph Ring 4 SO ₂ Pr
9-166 3-Cl-4-F-Ph Ring 4 COMe
9-167 3-Cl-4-F-Ph Ring 4 COEt
9-168 3-Cl-4-F-Ph Ring 4 COPr
9-169 4-F-Ph Ring 5 CONH ₂
9-170 4-F-Ph Ring 5 CONHMe
9-171 4-F-Ph Ring 5 CONHEt
9-172 4-F-Ph Ring 5 CONHPr
9-173 4-F-Ph Ring 5 CONH-i-Pr
9-174 4-F-Ph Ring 5 CONHBu
9-175 4-F-Ph Ring 5 SO ₂ NH ₂
9-176 4-F-Ph Ring 5 SO ₂ NHMe
9-177 4-F-Ph Ring 5 SO ₂ NHEt
9-178 4-F-Ph Ring 5 SO ₂ NHPr
9-179 4-F-Ph Ring 5 SO ₂ NH-i-Pr
9-180 4-F-Ph Ring 5 SO ₂ NHBu
9-181 4-F-Ph Ring 5 SOMe
9-182 4-F-Ph Ring 5 SOEt
9-183 4-F-Ph Ring 5 SOPr
9-184 4-F-Ph Ring 5 SO ₂ Me
9-185 4-F-Ph Ring 5 SO ₂ Et
9-186 4-F-Ph Ring 5 SO ₂ Pr
9-187 4-F-Ph Ring 5 COMe
9-188 4-F-Ph Ring 5 COEt
9-189 4-F-Ph Ring 5 COPr
9-190 3-Cl-4-F-Ph Ring 5 CONH ₂
9-191 3-Cl-4-F-Ph Ring 5 CONHMe
9-192 3-Cl-4-F-Ph Ring 5 CONHEt
9-193 3-Cl-4-F-Ph Ring 5 CONHPr
9-194 3-Cl-4-F-Ph Ring 5 CONH-i-Pr
9-195 3-Cl-4-F-Ph Ring 5 CONHBu
9-196 3-Cl-4-F-Ph Ring 5 SO ₂ NH ₂
9-197 3-Cl-4-F-Ph Ring 5 SO ₂ NHMe
9-198 3-Cl-4-F-Ph Ring 5 SO ₂ NHEt
9-199 3-Cl-4-F-Ph Ring 5 SO ₂ NHPr
9-200 3-Cl-4-F-Ph Ring 5 SO ₂ NH-i-Pr
9-201 3-Cl-4-F-Ph Ring 5 SO ₂ NHBu
9-202 3-Cl-4-F-Ph Ring 5 SOMe
9-203 3-Cl-4-F-Ph Ring 5 SOEt
9-204 3-Cl-4-F-Ph Ring 5 SOPr
9-205 3-Cl-4-F-Ph Ring 5 SO ₂ Me
9-206 3-Cl-4-F-Ph Ring 5 SO ₂ Et
9-207 3-Cl-4-F-Ph Ring 5 SO ₂ Pr
9-208 3-Cl-4-F-Ph Ring 5 COMe
9-209 3-Cl-4-F-Ph Ring 5 COEt
9-210 3-Cl-4-F-Ph Ring 5 COPr
9-211 4-F-Ph Ring 6 CONH ₂
9-212 4-F-Ph Ring 6 CONHMe
9-213 4-F-Ph Ring 6 CONHEt
9-214 4-F-Ph Ring 6 CONHPr
9-215 4-F-Ph Ring 6 CONH-i-Pr
9-216 4-F-Ph Ring 6 CONHBu
9-217 4-F-Ph Ring 6 SO ₂ NH ₂
9-218 4-F-Ph Ring 6 SO ₂ NHMe
9-219 4-F-Ph Ring 6 SO ₂ NHEt
9-220 4-F-Ph Ring 6 SO ₂ NHPr
9-221 4-F-Ph Ring 6 SO ₂ NH-i-Pr
9-222 4-F-Ph Ring 6 SO ₂ NHBu
9-223 4-F-Ph Ring 6 SOMe
9-224 4-F-Ph Ring 6 SOEt
9-225 4-F-Ph Ring 6 SOPr
9-226 4-F-Ph Ring 6 SO ₂ Me
9-227 4-F-Ph Ring 6 SO ₂ Et
9-228 4-F-Ph Ring 6 SO ₂ Pr
9-229 4-F-Ph Ring 6 COMe
9-230 4-F-Ph Ring 6 COEt
9-231 4-F-Ph Ring 6 COPr
9-232 3-Cl-4-F-Ph Ring 6 CONH ₂
9-233 3-Cl-4-F-Ph Ring 6 CONHMe
9-234 3-Cl-4-F-Ph Ring 6 CONHEt
9-235 3-Cl-4-F-Ph Ring 6 CONHPr
9-236 3-Cl-4-F-Ph Ring 6 CONH-i-Pr
9-237 3-Cl-4-F-Ph Ring 6 CONHBu
9-238 3-Cl-4-F-Ph Ring 6 SO ₂ NH ₂
9-239 3-Cl-4-F-Ph Ring 6 SO ₂ NHMe
9-240 3-Cl-4-F-Ph Ring 6 SO ₂ NHEt
9-241 3-Cl-4-F-Ph Ring 6 SO ₂ NHPr
9-242 3-Cl-4-F-Ph Ring 6 SO ₂ NH-i-Pr
9-243 3-Cl-4-F-Ph Ring 6 SO ₂ NHBu
9-244 3-Cl-4-F-Ph Ring 6 SOMe
9-245 3-Cl-4-F-Ph Ring 6 SOEt
9-246 3-Cl-4-F-Ph Ring 6 SOPr
9-247 3-Cl-4-F-Ph Ring 6 SO ₂ Me
9-248 3-Cl-4-F-Ph Ring 6 SO ₂ Et
9-249 3-Cl-4-F-Ph Ring 6 SO ₂ Pr
9-250 3-Cl-4-F-Ph Ring 6 COMe
9-251 3-Cl-4-F-Ph Ring 6 COEt
9-252 3-Cl-4-F-Ph Ring 6 COPr
9-253 4-F-Ph Ring 7 CONH ₂
9-254 4-F-Ph Ring 7 CONHMe
9-255 4-F-Ph Ring 7 CONHEt
9-256 4-F-Ph Ring 7 CONHPr
9-257 4-F-Ph Ring 7 CONH-i-Pr
9-258 4-F-Ph Ring 7 CONHBu
9-259 4-F-Ph Ring 7 SO ₂ NH ₂
9-260 4-F-Ph Ring 7 SO ₂ NHMe
9-261 4-F-Ph Ring 7 SO ₂ NHEt
9-262 4-F-Ph Ring 7 SO ₂ NHPr
9-263 4-F-Ph Ring 7 SO ₂ NH-i-Pr
9-264 4-F-Ph Ring 7 SO ₂ NHBu
9-265 4-F-Ph Ring 7 SOMe
9-266 4-F-Ph Ring 7 SOEt
9-267 4-F-Ph Ring 7 SOPr
9-268 4-F-Ph Ring 7 SO ₂ Me
9-269 4-F-Ph Ring 7 SO ₂ Et
9-270 4-F-Ph Ring 7 SO ₂ Pr
9-271 4-F-Ph Ring 7 COMe
9-272 4-F-Ph Ring 7 COEt
9-273 4-F-Ph Ring 7 COPr
9-274 3-Cl-4-F-Ph Ring 7 CONH ₂
9-275 3-Cl-4-F-Ph Ring 7 CONHMe
9-276 3-Cl-4-F-Ph Ring 7 CONHEt
9-277 3-Cl-4-F-Ph Ring 7 CONHPr
9-278 3-Cl-4-F-Ph Ring 7 CONH-i-Pr
9-279 3-Cl-4-F-Ph Ring 7 CONHBu
9-280 3-Cl-4-F-Ph Ring 7 SO ₂ NH ₂
9-281 3-Cl-4-F-Ph Ring 7 SO ₂ NHMe
9-282 3-Cl-4-F-Ph Ring 7 SO ₂ NHEt
9-283 3-Cl-4-F-Ph Ring 7 SO ₂ NHPr
9-284 3-Cl-4-F-Ph Ring 7 SO ₂ NH-i-Pr
9-285 3-Cl-4-F-Ph Ring 7 SO ₂ NHBu
9-286 3-Cl-4-F-Ph Ring 7 SOMe
9-287 3-Cl-4-F-Ph Ring 7 SOEt
9-288 3-Cl-4-F-Ph Ring 7 SOPr
9-289 3-Cl-4-F-Ph Ring 7 SO ₂ Me
9-290 3-Cl-4-F-Ph Ring 7 SO ₂ Et
9-291 3-Cl-4-F-Ph Ring 7 SO ₂ Pr
9-292 3-Cl-4-F-Ph Ring 7 COMe
9-293 3-Cl-4-F-Ph Ring 7 COEt
9-294 3-Cl-4-F-Ph Ring 7 COPr
9-295 4-F-Ph Ring 8 CONH ₂
9-296 4-F-Ph Ring 8 CONHMe
9-297 4-F-Ph Ring 8 CONHEt
9-298 4-F-Ph Ring 8 CONHPr
9-299 4-F-Ph Ring 8 CONH-i-Pr
9-300 4-F-Ph Ring 8 CONHBu
9-301 4-F-Ph Ring 8 SO ₂ NH ₂
9-302 4-F-Ph Ring 8 SO ₂ NHMe
9-303 4-F-Ph Ring 8 SO ₂ NHEt
9-304 4-F-Ph Ring 8 SO ₂ NHPr
9-305 4-F-Ph Ring 8 SO ₂ NH-i-Pr
9-306 4-F-Ph Ring 8 SO ₂ NHBu
9-307 4-F-Ph Ring 8 SOMe
9-308 4-F-Ph Ring 8 SOEt
9-309 4-F-Ph Ring 8 SOPr
9-310 4-F-Ph Ring 8 SO ₂ Me
9-311 4-F-Ph Ring 8 SO ₂ Et
9-312 4-F-Ph Ring 8 SO ₂ Pr
9-313 4-F-Ph Ring 8 COMe
9-314 4-F-Ph Ring 8 COEt
9-315 4-F-Ph Ring 8 COPr
9-316 3-Cl-4-F-Ph Ring 8 CONH ₂
9-317 3-Cl-4-F-Ph Ring 8 CONHMe
9-318 3-Cl-4-F-Ph Ring 8 CONHEt
9-319 3-Cl-4-F-Ph Ring 8 CONHPr
9-320 3-Cl-4-F-Ph Ring 8 CONH-i-Pr
9-321 3-Cl-4-F-Ph Ring 8 CONHBu
9-322 3-Cl-4-F-Ph Ring 8 SO ₂ NH ₂
9-323 3-Cl-4-F-Ph Ring 8 SO ₂ NHMe
9-324 3-Cl-4-F-Ph Ring 8 SO ₂ NHEt
9-325 3-Cl-4-F-Ph Ring 8 SO ₂ NHPr
9-326 3-Cl-4-F-Ph Ring 8 SO ₂ NH-i-Pr
9-327 3-Cl-4-F-Ph Ring 8 SO ₂ NHBu
9-328 3-Cl-4-F-Ph Ring 8 SOMe
9-329 3-Cl-4-F-Ph Ring 8 SOEt
9-330 3-Cl-4-F-Ph Ring 8 SOPr
9-331 3-Cl-4-F-Ph Ring 8 SO ₂ Me
9-332 3-Cl-4-F-Ph Ring 8 SO ₂ Et
9-333 3-Cl-4-F-Ph Ring 8 SO ₂ Pr
9-334 3-Cl-4-F-Ph Ring 8 COMe
9-335 3-Cl-4-F-Ph Ring 8 COEt
9-336 3-Cl-4-F-Ph Ring 8 COPr
9-337 4-F-Ph Ring 9 CONH ₂
9-338 4-F-Ph Ring 9 CONHMe
9-339 4-F-Ph Ring 9 CONHEt
9-340 4-F-Ph Ring 9 CONHPr
9-341 4-F-Ph Ring 9 CONH-i-Pr
9-342 4-F-Ph Ring 9 CONHBu
9-343 4-F-Ph Ring 9 SO ₂ NH ₂
9-344 4-F-Ph Ring 9 SO ₂ NHMe
9-345 4-F-Ph Ring 9 SO ₂ NHEt
9-346 4-F-Ph Ring 9 SO ₂ NHPr
9-347 4-F-Ph Ring 9 SO ₂ NH-i-Pr
9-348 4-F-Ph Ring 9 SO ₂ NHBu
9-349 4-F-Ph Ring 9 SOMe
9-350 4-F-Ph Ring 9 SOEt
9-351 4-F-Ph Ring 9 SOPr
9-352 4-F-Ph Ring 9 SO ₂ Me
9-353 4-F-Ph Ring 9 SO ₂ Et
9-354 4-F-Ph Ring 9 SO ₂ Pr
9-355 4-F-Ph Ring 9 COMe
9-356 4-F-Ph Ring 9 COEt
9-357 4-F-Ph Ring 9 COPr
9-358 3-Cl-4-F-Ph Ring 9 CONH ₂
9-359 3-Cl-4-F-Ph Ring 9 CONHMe
9-360 3-Cl-4-F-Ph Ring 9 CONHEt
9-361 3-Cl-4-F-Ph Ring 9 CONHPr
9-362 3-Cl-4-F-Ph Ring 9 CONH-i-Pr
9-363 3-Cl-4-F-Ph Ring 9 CONHBu
9-364 3-Cl-4-F-Ph Ring 9 SO ₂ NH ₂
9-365 3-Cl-4-F-Ph Ring 9 SO ₂ NHMe
9-366 3-Cl-4-F-Ph ring 9 SO ₂ NHEt
9-367 3-Cl-4-F-Ph ring 9 SO ₂ NHPr
9-368 3-Cl-4-F-Ph Ring 9 SO ₂ NH-i-Pr
9-369 3-Cl-4-F-Ph Ring 9 SO ₂ NHBu
9-370 3-Cl-4-F-Ph Ring 9 SOMe
9-371 3-Cl-4-F-Ph Ring 9 SOEt
9-372 3-Cl-4-F-Ph Ring 9 SOPr
9-373 3-Cl-4-F-Ph Ring 9 SO ₂ Me
9-374 3-Cl-4-F-Ph ring 9 SO ₂ Et
9-375 3-Cl-4-F-Ph Ring 9 SO ₂ Pr
9-376 3-Cl-4-F-Ph Ring 9 COMe
9-377 3-Cl-4-F-Ph Ring 9 COEt
9-378 3-Cl-4-F-Ph Ring 9 COPr
9-379 4-F-Ph Ring 10 CONH ₂
9-380 4-F-Ph Ring 10 CONHMe
9-381 4-F-Ph Ring 10 CONHEt
9-382 4-F-Ph Ring 10 CONHPr
9-383 4-F-Ph Ring 10 CONH-i-Pr
9-384 4-F-Ph Ring 10 CONHBu
9-385 4-F-Ph Ring 10 SO ₂ NH ₂
9-386 4-F-Ph Ring 10 SO ₂ NHMe
9-387 4-F-Ph Ring 10 SO ₂ NHEt
9-388 4-F-Ph Ring 10 SO ₂ NHPr
9-389 4-F-Ph Ring 10 SO ₂ NH-i-Pr
9-390 4-F-Ph Ring 10 SO ₂ NHBu
9-391 4-F-Ph Ring 10 SOMe
9-392 4-F-Ph Ring 10 SOEt
9-393 4-F-Ph Ring 10 SOPr
9-394 4-F-Ph Ring 10 SO ₂ Me
9-395 4-F-Ph Ring 10 SO ₂ Et
9-396 4-F-Ph Ring 10 SO ₂ Pr
9-397 4-F-Ph Ring 10 COMe
9-398 4-F-Ph Ring 10 COEt
9-399 4-F-Ph Ring 10 COPr
9-400 3-Cl-4-F-Ph Ring 10 CONH ₂
9-401 3-Cl-4-F-Ph Ring 10 CONHMe
9-402 3-Cl-4-F-Ph Ring 10 CONHEt
9-403 3-Cl-4-F-Ph Ring 10 CONHPr
9-404 3-Cl-4-F-Ph Ring 10 CONH-i-Pr
9-405 3-Cl-4-F-Ph Ring 10 CONHBu
9-406 3-Cl-4-F-Ph Ring 10 SO ₂ NH ₂
9-407 3-Cl-4-F-Ph Ring 10 SO ₂ NHMe
9-408 3-Cl-4-F-Ph Ring 10 SO ₂ NHEt
9-409 3-Cl-4-F-Ph Ring 10 SO ₂ NHPr
9-410 3-Cl-4-F-Ph Ring 10 SO ₂ NH-i-Pr
9-411 3-Cl-4-F-Ph Ring 10 SO ₂ NHBu
9-412 3-Cl-4-F-Ph Ring 10 SOMe
9-413 3-Cl-4-F-Ph Ring 10 SOEt
9-414 3-Cl-4-F-Ph Ring 10 SOPr
9-415 3-Cl-4-F-Ph Ring 10 SO ₂ Me
9-416 3-Cl-4-F-Ph Ring 10 SO ₂ Et
9-417 3-Cl-4-F-Ph Ring 10 SO ₂ Pr
9-418 3-Cl-4-F-Ph Ring 10 COMe
9-419 3-Cl-4-F-Ph Ring 10 COEt
9-420 3-Cl-4-F-Ph Ring 10 COPr
9-421 4-F-Ph Ring 11 CONH ₂
9-422 4-F-Ph Ring 11 CONHMe
9-423 4-F-Ph Ring 11 CONHEt
9-424 4-F-Ph Ring 11 CONHPr
9-425 4-F-Ph Ring 11 CONH-i-Pr
9-426 4-F-Ph Ring 11 CONHBu
9-427 4-F-Ph Ring 11 SO ₂ NH ₂
9-428 4-F-Ph Ring 11 SO ₂ NHMe
9-429 4-F-Ph Ring 11 SO ₂ NHEt
9-430 4-F-Ph Ring 11 SO ₂ NHPr
9-431 4-F-Ph Ring 11 SO ₂ NH-i-Pr
9-432 4-F-Ph Ring 11 SO ₂ NHBu
9-433 4-F-Ph Ring 11 SOMe
9-434 4-F-Ph Ring 11 SOEt
9-435 4-F-Ph Ring 11 SOPr
9-436 4-F-Ph Ring 11 SO ₂ Me
9-437 4-F-Ph Ring 11 SO ₂ Et
9-438 4-F-Ph Ring 11 SO ₂ Pr
9-439 4-F-Ph Ring 11 COMe
9-440 4-F-Ph Ring 11 COEt
9-441 4-F-Ph Ring 11 COPr
9-442 3-Cl-4-F-Ph Ring 11 CONH ₂
9-443 3-Cl-4-F-Ph Ring 11 CONHMe
9-444 3-Cl-4-F-Ph Ring 11 CONHEt
9-445 3-Cl-4-F-Ph Ring 11 CONHPr
9-446 3-Cl-4-F-Ph Ring 11 CONH-i-Pr
9-447 3-Cl-4-F-Ph Ring 11 CONHBu
9-448 3-Cl-4-F-Ph Ring 11 SO ₂ NH ₂
9-449 3-Cl-4-F-Ph Ring 11 SO ₂ NHMe
9-450 3-Cl-4-F-Ph Ring 11 SO ₂ NHEt
9-451 3-Cl-4-F-Ph Ring 11 SO ₂ NHPr
9-452 3-Cl-4-F-Ph Ring 11 SO ₂ NH-i-Pr
9-453 3-Cl-4-F-Ph Ring 11 SO ₂ NHBu
9-454 3-Cl-4-F-Ph Ring 11 SOMe
9-455 3-Cl-4-F-Ph Ring 11 SOEt
9-456 3-Cl-4-F-Ph Ring 11 SOPr
9-457 3-Cl-4-F-Ph Ring 11 SO ₂ Me
9-458 3-Cl-4-F-Ph Ring 11 SO ₂ Et
9-459 3-Cl-4-F-Ph Ring 11 SO ₂ Pr
9-460 3-Cl-4-F-Ph Ring 11 COMe
9-461 3-Cl-4-F-Ph Ring 11 COEt
9-462 3-Cl-4-F-Ph Ring 11 COPr
9-463 4-F-Ph Ring 12 CONH ₂
9-464 4-F-Ph Ring 12 CONHMe
9-465 4-F-Ph Ring 12 CONHEt
9-466 4-F-Ph Ring 12 CONHPr
9-467 4-F-Ph Ring 12 CONH-i-Pr
9-468 4-F-Ph Ring 12 CONHBu
9-469 4-F-Ph Ring 12 SO ₂ NH ₂
9-470 4-F-Ph Ring 12 SO ₂ NHMe
9-471 4-F-Ph Ring 12 SO ₂ NHEt
9-472 4-F-Ph Ring 12 SO ₂ NHPr
9-473 4-F-Ph Ring 12 SO ₂ NH-i-Pr
9-474 4-F-Ph Ring 12 SO ₂ NHBu
9-475 4-F-Ph Ring 12 SOMe
9-476 4-F-Ph Ring 12 SOEt
9-477 4-F-Ph Ring 12 SOPr
9-478 4-F-Ph Ring 12 SO ₂ Me
9-479 4-F-Ph Ring 12 SO ₂ Et
9-480 4-F-Ph Ring 12 SO ₂ Pr
9-481 4-F-Ph Ring 12 COMe
9-482 4-F-Ph Ring 12 COEt
9-483 4-F-Ph Ring 12 COPr
9-484 3-Cl-4-F-Ph Ring 12 CONH ₂
9-485 3-Cl-4-F-Ph Ring 12 CONHMe
9-486 3-Cl-4-F-Ph Ring 12 CONHEt
9-487 3-Cl-4-F-Ph Ring 12 CONHPr
9-488 3-Cl-4-F-Ph Ring 12 CONH-i-Pr
9-489 3-Cl-4-F-Ph Ring 12 CONHBu
9-490 3-Cl-4-F-Ph Ring 12 SO ₂ NH ₂
9-491 3-Cl-4-F-Ph Ring 12 SO ₂ NHMe
9-492 3-Cl-4-F-Ph Ring 12 SO ₂ NHEt
9-493 3-Cl-4-F-Ph Ring 12 SO ₂ NHPr
9-494 3-Cl-4-F-Ph Ring 12 SO ₂ NH-i-Pr
9-495 3-Cl-4-F-Ph Ring 12 SO ₂ NHBu
9-496 3-Cl-4-F-Ph Ring 12 SOMe
9-497 3-Cl-4-F-Ph Ring 12 SOEt
9-498 3-Cl-4-F-Ph Ring 12 SOPr
9-499 3-Cl-4-F-Ph Ring 12 SO ₂ Me
9-500 3-Cl-4-F-Ph Ring 12 SO ₂ Et
9-501 3-Cl-4-F-Ph Ring 12 SO ₂ Pr
9-502 3-Cl-4-F-Ph Ring 12 COMe
9-503 3-Cl-4-F-Ph Ring 12 COEt
9-504 3-Cl-4-F-Ph Ring 12 COPr
9-505 4-F-Ph Ring 13 CONH ₂
9-506 4-F-Ph Ring 13 CONHMe
9-507 4-F-Ph Ring 13 CONHEt
9-508 4-F-Ph Ring 13 CONHPr
9-509 4-F-Ph Ring 13 CONH-i-Pr
9-510 4-F-Ph Ring 13 CONHBu
9-511 4-F-Ph Ring 13 SO ₂ NH ₂
9-512 4-F-Ph Ring 13 SO ₂ NHMe
9-513 4-F-Ph Ring 13 SO ₂ NHEt
9-514 4-F-Ph Ring 13 SO ₂ NHPr
9-515 4-F-Ph Ring 13 SO ₂ NH-i-Pr
9-516 4-F-Ph Ring 13 SO ₂ NHBu
9-517 4-F-Ph Ring 13 SOMe
9-518 4-F-Ph Ring 13 SOEt
9-519 4-F-Ph Ring 13 SOPr
9-520 4-F-Ph Ring 13 SO ₂ Me
9-521 4-F-Ph Ring 13 SO ₂ Et
9-522 4-F-Ph Ring 13 SO ₂ Pr
9-523 4-F-Ph Ring 13 COMe
9-524 4-F-Ph Ring 13 COEt
9-525 4-F-Ph Ring 13 COPr
9-526 3-Cl-4-F-Ph Ring 13 CONH ₂
9-527 3-Cl-4-F-Ph Ring 13 CONHMe
9-528 3-Cl-4-F-Ph Ring 13 CONHEt
9-529 3-Cl-4-F-Ph Ring 13 CONHPr
9-530 3-Cl-4-F-Ph Ring 13 CONH-i-Pr
9-531 3-Cl-4-F-Ph Ring 13 CONHBu
9-532 3-Cl-4-F-Ph Ring 13 SO ₂ NH ₂
9-533 3-Cl-4-F-Ph Ring 13 SO ₂ NHMe
9-534 3-Cl-4-F-Ph Ring 13 SO ₂ NHEt
9-535 3-Cl-4-F-Ph Ring 13 SO ₂ NHPr
9-536 3-Cl-4-F-Ph Ring 13 SO ₂ NH-i-Pr
9-537 3-Cl-4-F-Ph Ring 13 SO ₂ NHBu
9-538 3-Cl-4-F-Ph Ring 13 SOMe
9-539 3-Cl-4-F-Ph Ring 13 SOEt
9-540 3-Cl-4-F-Ph Ring 13 SOPr
9-541 3-Cl-4-F-Ph Ring 13 SO ₂ Me
9-542 3-Cl-4-F-Ph Ring 13 SO ₂ Et
9-543 3-Cl-4-F-Ph Ring 13 SO ₂ Pr
9-544 3-Cl-4-F-Ph Ring 13 COMe
9-545 3-Cl-4-F-Ph Ring 13 COEt
9-546 3-Cl-4-F-Ph Ring 13 COPr
9-547 4-F-Ph Ring 14 CONH ₂
9-548 4-F-Ph Ring 14 CONHMe
9-549 4-F-Ph Ring 14 CONHEt
9-550 4-F-Ph Ring 14 CONHPr
9-551 4-F-Ph Ring 14 CONH-i-Pr
9-552 4-F-Ph Ring 14 CONHBu
9-553 4-F-Ph Ring 14 SO ₂ NH ₂
9-554 4-F-Ph Ring 14 SO ₂ NHMe
9-555 4-F-Ph Ring 14 SO ₂ NHEt
9-556 4-F-Ph Ring 14 SO ₂ NHPr
9-557 4-F-Ph Ring 14 SO ₂ NH-i-Pr
9-558 4-F-Ph Ring 14 SO ₂ NHBu
9-559 4-F-Ph Ring 14 SOMe
9-560 4-F-Ph Ring 14 SOEt
9-561 4-F-Ph Ring 14 SOPr
9-562 4-F-Ph Ring 14 SO ₂ Me
9-563 4-F-Ph Ring 14 SO ₂ Et
9-564 4-F-Ph Ring 14 SO ₂ Pr
9-565 4-F-Ph Ring 14 COMe
9-566 4-F-Ph Ring 14 COEt
9-567 4-F-Ph Ring 14 COPr
9-568 3-Cl-4-F-Ph Ring 14 CONH ₂
9-569 3-Cl-4-F-Ph Ring 14 CONHMe
9-570 3-Cl-4-F-Ph Ring 14 CONHEt
9-571 3-Cl-4-F-Ph Ring 14 CONHPr
9-572 3-Cl-4-F-Ph Ring 14 CONH-i-Pr
9-573 3-Cl-4-F-Ph Ring 14 CONHBu
9-574 3-Cl-4-F-Ph Ring 14 SO ₂ NH ₂
9-575 3-Cl-4-F-Ph ring 14 SO ₂ NHMe
9-576 3-Cl-4-F-Ph Ring 14 SO ₂ NHEt
9-577 3-Cl-4-F-Ph ring 14 SO ₂ NHPr
9-578 3-Cl-4-F-Ph Ring 14 SO ₂ NH-i-Pr
9-579 3-Cl-4-F-Ph Ring 14 SO ₂ NHBu
9-580 3-Cl-4-F-Ph Ring 14 SOMe
9-581 3-Cl-4-F-Ph Ring 14 SOEt
9-582 3-Cl-4-F-Ph Ring 14 SOPr
9-583 3-Cl-4-F-Ph ring 14 SO ₂ Me
9-584 3-Cl-4-F-Ph ring 14 SO ₂ Et
9-585 3-Cl-4-F-Ph Ring 14 SO ₂ Pr
9-586 3-Cl-4-F-Ph Ring 14 COMe
9-587 3-Cl-4-F-Ph Ring 14 COEt
9-588 3-Cl-4-F-Ph Ring 14 COPr
―――――――――――――――――――――――――
Table 10

―――――――――――――――――――――――――――――――――――
Compound R¹           R²                 R⁵ 
Number
―――――――――――――――――――――――――――――――――――
10-1 Ph 4-Pyr COOH
10-2 Ph 4-Pyr COOMe
10-3 Ph 4-Pyr COOEt
10-4 Ph 4-Pyr COOPr
10-5 Ph 4-Pyr COO-i-Pr
10-6 Ph 4-Pyr COOBu
10-7 Ph 4-Pyr COOBn
10-8 Ph 4-Pyr COOPh
10-9 Ph 4-Pyr CONH₂              
10-10 Ph 4-Pyr CONHMe
10-11 Ph 4-Pyr CONHEt
10-12 Ph 4-Pyr CONHPr
10-13 Ph 4-Pyr CONH-i-Pr
10-14 Ph 4-Pyr CONHBu
10-15 Ph 4-Pyr CONHBn
10-16 Ph 4-Pyr CONMe₂             
10-17 Ph 4-Pyr CONH-c-Pr
10-18 Ph 4-Pyr CONH-c-Bu
10-19 Ph 4-Pyr CONH-c-Pen
10-20 Ph 4-Pyr CONH-c-Hex
10-21 Ph 4-Pyr CONH-c-Hep
10-22 Ph 4-Pyr CONHCH₂-c-Pr
10-23 Ph 4-Pyr CONH-Allyl
10-24 Ph 4-Pyr CONH-Propargyl
10-25 Ph 4-Pyr CONHPh
10-26 Ph 4-Pyr CONH-3-Pyr
10-27 Ph 4-Pyr CONHCH₂-4-Pyr
10-28 Ph 4-Pyr CONH- (CH₂)₂-OH
10-29 Ph 4-Pyr CONHCH (CH₂OH)₂       
10-30 Ph 4-Pyr CONH- (CH₂)₂-OAc
10-31 Ph 4-Pyr CONHCH₂CN
10-32 Ph 4-Pyr CONH- (CH₂)₂-F
10-33 Ph 4-Pyr CONH- (CH₂)₂-OMe
10-34 Ph 4-Pyr CONH- (CH₂)₂-SMe
10-35 Ph 4-Pyr CONH- (CH₂)₂-NH₂      
10-36 Ph 4-Pyr CONH- (CH₂)₂-NHMe
10-37 Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
10-38 Ph 4-Pyr CONHCH₂COOH
10-39 Ph 4-Pyr CONHCH₂COOEt
10-40 Ph 4-Pyr CONHCH (Me) COOEt
10-41 Ph 4-Pyr CONHCH₂CONH₂         
10-42 Ph 4-Pyr CONHOH
10-43 Ph 4-Pyr CONHOMe
10-44 Ph 4-Pyr CONHOEt
10-45 Ph 4-Pyr CONHOPr
10-46 Ph 4-Pyr CONHO-Allyl
10-47 Ph 4-Pyr CONHOBn
10-48 Ph 4-Pyr CONHNH₂            
10-49 Ph 4-Pyr CONHNHMe
10-50 Ph 4-Pyr CONHN (Me)₂          
10-51 Ph 4-Pyr COMe
10-52 Ph 4-Pyr COEt
10-53 Ph 4-Pyr COPr
10-54 Ph 4-Pyr CO-i-Pr
10-55 Ph 4-Pyr COBu
10-56 Ph 4-Pyr COCF_Three              
10-57 Ph 4-Pyr CO- (CH₂)₂-F
10-58 Ph 4-Pyr CO- (CH₂)₂-OH
10-59 Ph 4-Pyr CO- (CH₂)₂-OMe
10-60 Ph 4-Pyr SOMe
10-61 Ph 4-Pyr SOEt
10-62 Ph 4-Pyr SOPr
10-63 Ph 4-Pyr SO-i-Pr
10-64 Ph 4-Pyr SOBu
10-65 Ph 4-Pyr SOCF_Three              
10-66 Ph 4-Pyr SO- (CH₂)₂-F
10-67 Ph 4-Pyr SO- (CH₂)₂-OH
10-68 Ph 4-Pyr SO- (CH₂)₂-OMe
10-69 Ph 4-Pyr SO₂Me
10-70 Ph 4-Pyr SO₂Et
10-71 Ph 4-Pyr SO₂Pr
10-72 Ph 4-Pyr SO₂-i-Pr
10-73 Ph 4-Pyr SO₂Bu
10-74 Ph 4-Pyr SO₂CF_Three              
10-75 Ph 4-Pyr SO₂-(CH₂)₂-F
10-76 Ph 4-Pyr SO₂-(CH₂)₂-OH
10-77 Ph 4-Pyr SO₂-(CH₂)₂-OMe
10-78 Ph 4-Pyr SO₂NH₂              
10-79 Ph 4-Pyr SO₂NHMe
10-80 Ph 4-Pyr SO₂NHEt
10-81 Ph 4-Pyr SO₂NHPr
10-82 Ph 4-Pyr SO₂NH-i-Pr
10-83 Ph 4-Pyr SO₂NHBu
10-84 Ph 4-Pyr SO₂NHBn
10-85 Ph 4-Pyr SO₂NMe₂             
10-86 Ph 4-Pyr SO₂NH-c-Pr
10-87 Ph 4-Pyr SO₂NH-c-Bu
10-88 Ph 4-Pyr SO₂NH-c-Pen
10-89 Ph 4-Pyr SO₂NH-c-Hex
10-90 Ph 4-Pyr SO₂NH-c-Hep
10-91 Ph 4-Pyr SO₂NHCH₂-c-Pr
10-92 Ph 4-Pyr SO₂NH-Allyl
10-93 Ph 4-Pyr SO₂NH-Propargyl
10-94 Ph 4-Pyr SO₂NHPh
10-95 Ph 4-Pyr SO₂NH-3-Pyr
10-96 Ph 4-Pyr SO₂NHCH₂-4-Pyr
10-97 Ph 4-Pyr SO₂NH- (CH₂)₂-OH
10-98 Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
10-99 Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
10-100 Ph 4-Pyr SO₂NHCH₂CN
10-101 Ph 4-Pyr SO₂NH- (CH₂)₂-F
10-102 Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
10-103 Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
10-104 Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
10-105 Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
10-106 Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
10-107 Ph 4-Pyr SO₂NHCH₂COOH
10-108 Ph 4-Pyr SO₂NHCH₂COOEt
10-109 Ph 4-Pyr SO₂NHCH (Me) COOEt
10-110 Ph 4-Pyr SO₂NHCH₂CONH₂        
10-111 Ph 4-Pyr SO₂NHOH
10-112 Ph 4-Pyr SO₂NHOMe
10-113 Ph 4-Pyr SO₂NHOEt
10-114 Ph 4-Pyr SO₂NHOPr
10-115 Ph 4-Pyr SO₂NHOAllyl
10-116 Ph 4-Pyr SO₂NHOBn
10-117 Ph 4-Pyr SO₂NHNH₂            
10-118 Ph 4-Pyr SO₂NHNHMe
10-119 Ph 4-Pyr SO₂NHN (Me)₂          
10-120 3-F-Ph 4-Pyr COOH
10-121 3-F-Ph 4-Pyr COOMe
10-122 3-F-Ph 4-Pyr COOEt
10-123 3-F-Ph 4-Pyr COOPr
10-124 3-F-Ph 4-Pyr COO-i-Pr
10-125 3-F-Ph 4-Pyr COOBu
10-126 3-F-Ph 4-Pyr COOBn
10-127 3-F-Ph 4-Pyr COOPh
10-128 3-F-Ph 4-Pyr CONH₂              
10-129 3-F-Ph 4-Pyr CONHMe
10-130 3-F-Ph 4-Pyr CONHEt
10-131 3-F-Ph 4-Pyr CONHPr
10-132 3-F-Ph 4-Pyr CONH-i-Pr
10-133 3-F-Ph 4-Pyr CONHBu
10-134 3-F-Ph 4-Pyr CONHBn
10-135 3-F-Ph 4-Pyr CONMe₂             
10-136 3-F-Ph 4-Pyr CONH-c-Pr
10-137 3-F-Ph 4-Pyr CONH-c-Bu
10-138 3-F-Ph 4-Pyr CONH-c-Pen
10-139 3-F-Ph 4-Pyr CONH-c-Hex
10-140 3-F-Ph 4-Pyr CONH-c-Hep
10-141 3-F-Ph 4-Pyr CONHCH₂-c-Pr
10-142 3-F-Ph 4-Pyr CONH-Allyl
10-143 3-F-Ph 4-Pyr CONH-Propargyl
10-144 3-F-Ph 4-Pyr CONHPh
10-145 3-F-Ph 4-Pyr CONH-3-Pyr
10-146 3-F-Ph 4-Pyr CONHCH₂-4-Pyr
10-147 3-F-Ph 4-Pyr CONH- (CH₂)₂-OH
10-148 3-F-Ph 4-Pyr CONHCH (CH₂OH)₂       
10-149 3-F-Ph 4-Pyr CONH- (CH₂)₂-OAc
10-150 3-F-Ph 4-Pyr CONHCH₂CN
10-151 3-F-Ph 4-Pyr CONH- (CH₂)₂-F
10-152 3-F-Ph 4-Pyr CONH- (CH₂)₂-OMe
10-153 3-F-Ph 4-Pyr CONH- (CH₂)₂-SMe
10-154 3-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
10-155 3-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe
10-156 3-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
10-157 3-F-Ph 4-Pyr CONHCH₂COOH
10-158 3-F-Ph 4-Pyr CONHCH₂COOEt
10-159 3-F-Ph 4-Pyr CONHCH (Me) COOEt
10-160 3-F-Ph 4-Pyr CONHCH₂CONH₂         
10-161 3-F-Ph 4-Pyr CONHOH
10-162 3-F-Ph 4-Pyr CONHOMe
10-163 3-F-Ph 4-Pyr CONHOEt
10-164 3-F-Ph 4-Pyr CONHOPr
10-165 3-F-Ph 4-Pyr CONHOAllyl
10-166 3-F-Ph 4-Pyr CONHOBn
10-167 3-F-Ph 4-Pyr CONHNH₂            
10-168 3-F-Ph 4-Pyr CONHNHMe
10-169 3-F-Ph 4-Pyr CONHN (Me)₂          
10-170 3-F-Ph 4-Pyr COMe
10-171 3-F-Ph 4-Pyr COEt
10-172 3-F-Ph 4-Pyr COPr
10-173 3-F-Ph 4-Pyr CO-i-Pr
10-174 3-F-Ph 4-Pyr COBu
10-175 3-F-Ph 4-Pyr COCF_Three              
10-176 3-F-Ph 4-Pyr CO- (CH₂)₂-F          
10-177 3-F-Ph 4-Pyr CO- (CH₂)₂-OH         
10-178 3-F-Ph 4-Pyr CO- (CH₂)₂-OMe        
10-179 3-F-Ph 4-Pyr SOMe
10-180 3-F-Ph 4-Pyr SOEt
10-181 3-F-Ph 4-Pyr SOPr
10-182 3-F-Ph 4-Pyr SO-i-Pr
10-183 3-F-Ph 4-Pyr SOBu
10-184 3-F-Ph 4-Pyr SOCF_Three              
10-185 3-F-Ph 4-Pyr SO- (CH₂)₂-F          
10-186 3-F-Ph 4-Pyr SO- (CH₂)₂-OH         
10-187 3-F-Ph 4-Pyr SO- (CH₂)₂-OMe        
10-188 3-F-Ph 4-Pyr SO₂Me
10-189 3-F-Ph 4-Pyr SO₂Et
10-190 3-F-Ph 4-Pyr SO₂Pr
10-191 3-F-Ph 4-Pyr SO₂-i-Pr
10-192 3-F-Ph 4-Pyr SO₂Bu
10-193 3-F-Ph 4-Pyr SO₂CF_Three              
10-194 3-F-Ph 4-Pyr SO₂-(CH₂)₂-F
10-195 3-F-Ph 4-Pyr SO₂-(CH₂)₂-OH
10-196 3-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe
10-197 3-F-Ph 4-Pyr SO₂NH₂               
10-198 3-F-Ph 4-Pyr SO₂NHMe
10-199 3-F-Ph 4-Pyr SO₂NHEt
10-200 3-F-Ph 4-Pyr SO₂NHPr
10-201 3-F-Ph 4-Pyr SO₂NH-i-Pr
10-202 3-F-Ph 4-Pyr SO₂NHBu
10-203 3-F-Ph 4-Pyr SO₂NHBn
10-204 3-F-Ph 4-Pyr SO₂NMe₂            
10-205 3-F-Ph 4-Pyr SO₂NH-c-Pr
10-206 3-F-Ph 4-Pyr SO₂NH-c-Bu
10-207 3-F-Ph 4-Pyr SO₂NH-c-Pen
10-208 3-F-Ph 4-Pyr SO₂NH-c-Hex
10-209 3-F-Ph 4-Pyr SO₂NH-c-Hep
10-210 3-F-Ph 4-Pyr SO₂NHCH₂-c-Pr
10-211 3-F-Ph 4-Pyr SO₂NH-Allyl
10-212 3-F-Ph 4-Pyr SO₂NH-Propargyl
10-213 3-F-Ph 4-Pyr SO₂NHPh
10-214 3-F-Ph 4-Pyr SO₂NH-3-Pyr
10-215 3-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr       
10-216 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
10-217 3-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
10-218 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
10-219 3-F-Ph 4-Pyr SO₂NHCH₂CN           
10-220 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F
10-221 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
10-222 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
10-223 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
10-224 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe    
10-225 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
10-226 3-F-Ph 4-Pyr SO₂NHCH₂COOH
10-227 3-F-Ph 4-Pyr SO₂NHCH₂COOEt
10-228 3-F-Ph 4-Pyr SO₂NHCH (Me) COOEt
10-229 3-F-Ph 4-Pyr SO₂NHCH₂CONH₂        
10-230 3-F-Ph 4-Pyr SO₂NHOH
10-231 3-F-Ph 4-Pyr SO₂NHOMe
10-232 3-F-Ph 4-Pyr SO₂NHOEt
10-233 3-F-Ph 4-Pyr SO₂NHOPr
10-234 3-F-Ph 4-Pyr SO₂NHOAllyl
10-235 3-F-Ph 4-Pyr SO₂NHOBn
10-236 3-F-Ph 4-Pyr SO₂NHNH₂            
10-237 3-F-Ph 4-Pyr SO₂NHNHMe
10-238 3-F-Ph 4-Pyr SO₂NHN (Me)₂         
10-239 3-Cl-Ph 4-Pyr COOH
10-240 3-Cl-Ph 4-Pyr COOMe
10-241 3-Cl-Ph 4-Pyr COOEt
10-242 3-Cl-Ph 4-Pyr COOPr
10-243 3-Cl-Ph 4-Pyr COO-i-Pr
10-244 3-Cl-Ph 4-Pyr COOBu
10-245 3-Cl-Ph 4-Pyr COOBn
10-246 3-Cl-Ph 4-Pyr COOPh
10-247 3-Cl-Ph 4-Pyr CONH₂              
10-248 3-Cl-Ph 4-Pyr CONHMe
10-249 3-Cl-Ph 4-Pyr CONHEt
10-250 3-Cl-Ph 4-Pyr CONHPr
10-251 3-Cl-Ph 4-Pyr CONH-i-Pr
10-252 3-Cl-Ph 4-Pyr CONHBu
10-253 3-Cl-Ph 4-Pyr CONHBn
10-254 3-Cl-Ph 4-Pyr CONMe₂             
10-255 3-Cl-Ph 4-Pyr CONH-c-Pr
10-256 3-Cl-Ph 4-Pyr CONH-c-Bu
10-257 3-Cl-Ph 4-Pyr CONH-c-Pen
10-258 3-Cl-Ph 4-Pyr CONH-c-Hex
10-259 3-Cl-Ph 4-Pyr CONH-c-Hep
10-260 3-Cl-Ph 4-Pyr CONHCH₂-c-Pr
10-261 3-Cl-Ph 4-Pyr CONH-Allyl
10-262 3-Cl-Ph 4-Pyr CONH-Propargyl
10-263 3-Cl-Ph 4-Pyr CONHPh
10-264 3-Cl-Ph 4-Pyr CONH-3-Pyr
10-265 3-Cl-Ph 4-Pyr CONHCH₂-4-Pyr
10-266 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OH
10-267 3-Cl-Ph 4-Pyr CONHCH (CH₂OH)₂       
10-268 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OAc
10-269 3-Cl-Ph 4-Pyr CONHCH₂CN
10-270 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-F
10-271 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OMe
10-272 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-SMe
10-273 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
10-274 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-NHMe     
10-275 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
10-276 3-Cl-Ph 4-Pyr CONHCH₂COOH
10-277 3-Cl-Ph 4-Pyr CONHCH₂COOEt
10-278 3-Cl-Ph 4-Pyr CONHCH (Me) COOEt
10-279 3-Cl-Ph 4-Pyr CONHCH₂CONH₂        
10-280 3-Cl-Ph 4-Pyr CONHOH
10-281 3-Cl-Ph 4-Pyr CONHOMe
10-282 3-Cl-Ph 4-Pyr CONHOEt
10-283 3-Cl-Ph 4-Pyr CONHOPr
10-284 3-Cl-Ph 4-Pyr CONHOAllyl
10-285 3-Cl-Ph 4-Pyr CONHOBn
10-286 3-Cl-Ph 4-Pyr CONHNH₂            
10-287 3-Cl-Ph 4-Pyr CONHNHMe
10-288 3-Cl-Ph 4-Pyr CONHN (Me)₂          
10-289 3-Cl-Ph 4-Pyr COMe
10-290 3-Cl-Ph 4-Pyr COEt
10-291 3-Cl-Ph 4-Pyr COPr
10-292 3-Cl-Ph 4-Pyr CO-i-Pr
10-293 3-Cl-Ph 4-Pyr COBu
10-294 3-Cl-Ph 4-Pyr COCF_Three               
10-295 3-Cl-Ph 4-Pyr CO- (CH₂)₂-F
10-296 3-Cl-Ph 4-Pyr CO- (CH₂)₂-OH
10-297 3-Cl-Ph 4-Pyr CO- (CH₂)₂-OMe
10-298 3-Cl-Ph 4-Pyr SOMe
10-299 3-Cl-Ph 4-Pyr SOEt
10-300 3-Cl-Ph 4-Pyr SOPr
10-301 3-Cl-Ph 4-Pyr SO-i-Pr
10-302 3-Cl-Ph 4-Pyr SOBu
10-303 3-Cl-Ph 4-Pyr SOCF_Three               
10-304 3-Cl-Ph 4-Pyr SO- (CH₂)₂-F          
10-305 3-Cl-Ph 4-Pyr SO- (CH₂)₂-OH         
10-306 3-Cl-Ph 4-Pyr SO- (CH₂)₂-OMe        
10-307 3-Cl-Ph 4-Pyr SO₂Me
10-308 3-Cl-Ph 4-Pyr SO₂Et
10-309 3-Cl-Ph 4-Pyr SO₂Pr
10-310 3-Cl-Ph 4-Pyr SO₂-i-Pr
10-311 3-Cl-Ph 4-Pyr SO₂Bu                
10-312 3-Cl-Ph 4-Pyr SO₂CF_Three              
10-313 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-F
10-314 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-OH
10-315 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-OMe
10-316 3-Cl-Ph 4-Pyr SO₂NH₂              
10-317 3-Cl-Ph 4-Pyr SO₂NHMe
10-318 3-Cl-Ph 4-Pyr SO₂NHEt
10-319 3-Cl-Ph 4-Pyr SO₂NHPr
10-320 3-Cl-Ph 4-Pyr SO₂NH-i-Pr
10-321 3-Cl-Ph 4-Pyr SO₂NHBu
10-322 3-Cl-Ph 4-Pyr SO₂NHBn
10-323 3-Cl-Ph 4-Pyr SO₂NMe₂             
10-324 3-Cl-Ph 4-Pyr SO₂NH-c-Pr
10-325 3-Cl-Ph 4-Pyr SO₂NH-c-Bu
10-326 3-Cl-Ph 4-Pyr SO₂NH-c-Pen
10-327 3-Cl-Ph 4-Pyr SO₂NH-c-Hex
10-328 3-Cl-Ph 4-Pyr SO₂NH-c-Hep
10-329 3-Cl-Ph 4-Pyr SO₂NHCH₂-c-Pr
10-330 3-Cl-Ph 4-Pyr SO₂NH-Allyl
10-331 3-Cl-Ph 4-Pyr SO₂NH-Propargyl
10-332 3-Cl-Ph 4-Pyr SO₂NHPh
10-333 3-Cl-Ph 4-Pyr SO₂NH-3-Pyr
10-334 3-Cl-Ph 4-Pyr SO₂NHCH₂-4-Pyr
10-335 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
10-336 3-Cl-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
10-337 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
10-338 3-Cl-Ph 4-Pyr SO₂NHCH₂CN           
10-339 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-F
10-340 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
10-341 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
10-342 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
10-343 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
10-344 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂ 
10-345 3-Cl-Ph 4-Pyr SO₂NHCH₂COOH
10-346 3-Cl-Ph 4-Pyr SO₂NHCH₂COOEt
10-347 3-Cl-Ph 4-Pyr SO₂NHCH (Me) COOEt
10-348 3-Cl-Ph 4-Pyr SO₂NHCH₂CONH₂        
10-349 3-Cl-Ph 4-Pyr SO₂NHOH
10-350 3-Cl-Ph 4-Pyr SO₂NHOMe
10-351 3-Cl-Ph 4-Pyr SO₂NHOEt
10-352 3-Cl-Ph 4-Pyr SO₂NHOPr
10-353 3-Cl-Ph 4-Pyr SO₂NHOAllyl
10-354 3-Cl-Ph 4-Pyr SO₂NHOBn
10-355 3-Cl-Ph 4-Pyr SO₂NHNH₂            
10-356 3-Cl-Ph 4-Pyr SO₂NHNHMe
10-357 3-Cl-Ph 4-Pyr SO₂NHN (Me)₂         
10-358 4-F-Ph 4-Pyr COOH
10-359 4-F-Ph 4-Pyr COOMe
10-360 4-F-Ph 4-Pyr COOEt
10-361 4-F-Ph 4-Pyr COOPr
10-362 4-F-Ph 4-Pyr COO-i-Pr
10-363 4-F-Ph 4-Pyr COOBu
10-364 4-F-Ph 4-Pyr COOBn
10-365 4-F-Ph 4-Pyr COOPh
10-366 4-F-Ph 4-Pyr CONH₂               
10-367 4-F-Ph 4-Pyr CONHMe
10-368 4-F-Ph 4-Pyr CONHEt
10-369 4-F-Ph 4-Pyr CONHPr
10-370 4-F-Ph 4-Pyr CONH-i-Pr
10-371 4-F-Ph 4-Pyr CONHBu
10-372 4-F-Ph 4-Pyr CONHBn
10-373 4-F-Ph 4-Pyr CONMe₂              
10-374 4-F-Ph 4-Pyr CONH-c-Pr
10-375 4-F-Ph 4-Pyr CONH-c-Bu
10-376 4-F-Ph 4-Pyr CONH-c-Pen
10-377 4-F-Ph 4-Pyr CONH-c-Hex
10-378 4-F-Ph 4-Pyr CONH-c-Hep
10-379 4-F-Ph 4-Pyr CONHCH₂-c-Pr         
10-380 4-F-Ph 4-Pyr CONH-Allyl
10-381 4-F-Ph 4-Pyr CONH-Propargyl
10-382 4-F-Ph 4-Pyr CONHPh
10-383 4-F-Ph 4-Pyr CONH-3-Pyr
10-384 4-F-Ph 4-Pyr CONHCH₂-4-Pyr        
10-385 4-F-Ph 4-Pyr CONH- (CH₂)₂-OH       
10-386 4-F-Ph 4-Pyr CONHCH (CH₂OH)₂      
10-387 4-F-Ph 4-Pyr CONH- (CH₂)₂-OAc      
10-388 4-F-Ph 4-Pyr CONHCH₂CN
10-389 4-F-Ph 4-Pyr CONH- (CH₂)₂-F        
10-390 4-F-Ph 4-Pyr CONH- (CH₂)₂-OMe      
10-391 4-F-Ph 4-Pyr CONH- (CH₂)₂-SMe      
10-392 4-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
10-393 4-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe     
10-394 4-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
10-395 4-F-Ph 4-Pyr CONHCH₂COOH
10-396 4-F-Ph 4-Pyr CONHCH₂COOEt
10-397 4-F-Ph 4-Pyr CONHCH (Me) COOEt
10-398 4-F-Ph 4-Pyr CONHCH₂CONH₂        
10-399 4-F-Ph 4-Pyr CONHOH
10-400 4-F-Ph 4-Pyr CONHOMe
10-401 4-F-Ph 4-Pyr CONHOEt
10-402 4-F-Ph 4-Pyr CONHOPr
10-403 4-F-Ph 4-Pyr CONHOAllyl
10-404 4-F-Ph 4-Pyr CONHOBn
10-405 4-F-Ph 4-Pyr CONHNH₂             
10-406 4-F-Ph 4-Pyr CONHNHMe
10-407 4-F-Ph 4-Pyr CONHN (Me)₂          
10-408 4-F-Ph 4-Pyr COMe
10-409 4-F-Ph 4-Pyr COEt
10-410 4-F-Ph 4-Pyr COPr
10-411 4-F-Ph 4-Pyr CO-i-Pr
10-412 4-F-Ph 4-Pyr COBu
10-413 4-F-Ph 4-Pyr COCF_Three               
10-414 4-F-Ph 4-Pyr CO- (CH₂)₂-F         
10-415 4-F-Ph 4-Pyr CO- (CH₂)₂-OH
10-416 4-F-Ph 4-Pyr CO- (CH₂)₂-OMe
10-417 4-F-Ph 4-Pyr SOMe
10-418 4-F-Ph 4-Pyr SOEt
10-419 4-F-Ph 4-Pyr SOPr
10-420 4-F-Ph 4-Pyr SO-i-Pr
10-421 4-F-Ph 4-Pyr SOBu
10-422 4-F-Ph 4-Pyr SOCF_Three               
10-423 4-F-Ph 4-Pyr SO- (CH₂)₂-F
10-424 4-F-Ph 4-Pyr SO- (CH₂)₂-OH
10-425 4-F-Ph 4-Pyr SO- (CH₂)₂-OMe
10-426 4-F-Ph 4-Pyr SO₂Me
10-427 4-F-Ph 4-Pyr SO₂Et
10-428 4-F-Ph 4-Pyr SO₂Pr
10-429 4-F-Ph 4-Pyr SO₂-i-Pr
10-430 4-F-Ph 4-Pyr SO₂Bu
10-431 4-F-Ph 4-Pyr SO₂CF_Three              
10-432 4-F-Ph 4-Pyr SO₂-(CH₂)₂-F
10-433 4-F-Ph 4-Pyr SO₂-(CH₂)₂-OH
10-434 4-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe
10-435 4-F-Ph 4-Pyr SO₂NH₂              
10-436 4-F-Ph 4-Pyr SO₂NHMe
10-437 4-F-Ph 4-Pyr SO₂NHEt
10-438 4-F-Ph 4-Pyr SO₂NHPr
10-439 4-F-Ph 4-Pyr SO₂NH-i-Pr
10-440 4-F-Ph 4-Pyr SO₂NHBu
10-441 4-F-Ph 4-Pyr SO₂NHBn
10-442 4-F-Ph 4-Pyr SO₂NMe₂             
10-443 4-F-Ph 4-Pyr SO₂NH-c-Pr
10-444 4-F-Ph 4-Pyr SO₂NH-c-Bu
10-445 4-F-Ph 4-Pyr SO₂NH-c-Pen
10-446 4-F-Ph 4-Pyr SO₂NH-c-Hex
10-447 4-F-Ph 4-Pyr SO₂NH-c-Hep
10-448 4-F-Ph 4-Pyr SO₂NHCH₂-c-Pr        
10-449 4-F-Ph 4-Pyr SO₂NH-Allyl
10-450 4-F-Ph 4-Pyr SO₂NH-Propargyl
10-451 4-F-Ph 4-Pyr SO₂NHPh
10-452 4-F-Ph 4-Pyr SO₂NH-3-Pyr
10-453 4-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr
10-454 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH      
10-455 4-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂     
10-456 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc     
10-457 4-F-Ph 4-Pyr SO₂NHCH₂CN
10-458 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F
10-459 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
10-460 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
10-461 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
10-462 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
10-463 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
10-464 4-F-Ph 4-Pyr SO₂NHCH₂COOH
10-465 4-F-Ph 4-Pyr SO₂NHCH₂COOEt        
10-466 4-F-Ph 4-Pyr SO₂NHCH (Me) COOEt
10-467 4-F-Ph 4-Pyr SO₂NHCH₂CONH₂        
10-468 4-F-Ph 4-Pyr SO₂NHOH
10-469 4-F-Ph 4-Pyr SO₂NHOMe
10-470 4-F-Ph 4-Pyr SO₂NHOEt
10-471 4-F-Ph 4-Pyr SO₂NHOPr
10-472 4-F-Ph 4-Pyr SO₂NHOAllyl
10-473 4-F-Ph 4-Pyr SO₂NHOBn
10-474 4-F-Ph 4-Pyr SO₂NHNH₂            
10-475 4-F-Ph 4-Pyr SO₂NHNHMe
10-476 4-F-Ph 4-Pyr SO₂NHN (Me)₂         
10-477 3-Cl-4-F-Ph 4-Pyr COOH
10-478 3-Cl-4-F-Ph 4-Pyr COOMe
10-479 3-Cl-4-F-Ph 4-Pyr COOEt
10-480 3-Cl-4-F-Ph 4-Pyr COOPr
10-481 3-Cl-4-F-Ph 4-Pyr COO-i-Pr
10-482 3-Cl-4-F-Ph 4-Pyr COOBu
10-483 3-Cl-4-F-Ph 4-Pyr COOBn
10-484 3-Cl-4-F-Ph 4-Pyr COOPh
10-485 3-Cl-4-F-Ph 4-Pyr CONH₂              
10-486 3-Cl-4-F-Ph 4-Pyr CONHMe
10-487 3-Cl-4-F-Ph 4-Pyr CONHEt
10-488 3-Cl-4-F-Ph 4-Pyr CONHPr
10-489 3-Cl-4-F-Ph 4-Pyr CONH-i-Pr
10-490 3-Cl-4-F-Ph 4-Pyr CONHBu
10-491 3-Cl-4-F-Ph 4-Pyr CONHBn
10-492 3-Cl-4-F-Ph 4-Pyr CONMe₂             
10-493 3-Cl-4-F-Ph 4-Pyr CONH-c-Pr
10-494 3-Cl-4-F-Ph 4-Pyr CONH-c-Bu
10-495 3-Cl-4-F-Ph 4-Pyr CONH-c-Pen
10-496 3-Cl-4-F-Ph 4-Pyr CONH-c-Hex
10-497 3-Cl-4-F-Ph 4-Pyr CONH-c-Hep
10-498 3-Cl-4-F-Ph 4-Pyr CONHCH₂-c-Pr
10-499 3-Cl-4-F-Ph 4-Pyr CONH-Allyl
10-500 3-Cl-4-F-Ph 4-Pyr CONH-Propargyl
10-501 3-Cl-4-F-Ph 4-Pyr CONHPh
10-502 3-Cl-4-F-Ph 4-Pyr CONH-3-Pyr
10-503 3-Cl-4-F-Ph 4-Pyr CONHCH₂-4-Pyr
10-504 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OH       
10-505 3-Cl-4-F-Ph 4-Pyr CONHCH (CH₂OH)₂      
10-506 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OAc      
10-507 3-Cl-4-F-Ph 4-Pyr CONHCH₂CN
10-508 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-F        
10-509 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OMe      
10-510 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-SMe      
10-511 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
10-512 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe     
10-513 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
10-514 3-Cl-4-F-Ph 4-Pyr CONHCH₂COOH
10-515 3-Cl-4-F-Ph 4-Pyr CONHCH₂COOEt
10-516 3-Cl-4-F-Ph 4-Pyr CONHCH (Me) COOEt
10-517 3-Cl-4-F-Ph 4-Pyr CONHCH₂CONH₂        
10-518 3-Cl-4-F-Ph 4-Pyr CONHOH
10-519 3-Cl-4-F-Ph 4-Pyr CONHOMe
10-520 3-Cl-4-F-Ph 4-Pyr CONHOEt
10-521 3-Cl-4-F-Ph 4-Pyr CONHOPr
10-522 3-Cl-4-F-Ph 4-Pyr CONHOAllyl
10-523 3-Cl-4-F-Ph 4-Pyr CONHOBn
10-524 3-Cl-4-F-Ph 4-Pyr CONHNH₂             
10-525 3-Cl-4-F-Ph 4-Pyr CONHNHMe
10-526 3-Cl-4-F-Ph 4-Pyr CONHN (Me)₂          
10-527 3-Cl-4-F-Ph 4-Pyr COMe
10-528 3-Cl-4-F-Ph 4-Pyr COEt
10-529 3-Cl-4-F-Ph 4-Pyr COPr
10-530 3-Cl-4-F-Ph 4-Pyr CO-i-Pr
10-531 3-Cl-4-F-Ph 4-Pyr COBu
10-532 3-Cl-4-F-Ph 4-Pyr COCF_Three              
10-533 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-F
10-534 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-OH         
10-535 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-OMe        
10-536 3-Cl-4-F-Ph 4-Pyr SOMe
10-537 3-Cl-4-F-Ph 4-Pyr SOEt
10-538 3-Cl-4-F-Ph 4-Pyr SOPr
10-539 3-Cl-4-F-Ph 4-Pyr SO-i-Pr
10-540 3-Cl-4-F-Ph 4-Pyr SOBu
10-541 3-Cl-4-F-Ph 4-Pyr SOCF_Three              
10-542 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-F
10-543 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-OH
10-544 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-OMe
10-545 3-Cl-4-F-Ph 4-Pyr SO₂Me
10-546 3-Cl-4-F-Ph 4-Pyr SO₂Et
10-547 3-Cl-4-F-Ph 4-Pyr SO₂Pr
10-548 3-Cl-4-F-Ph 4-Pyr SO₂-i-Pr
10-549 3-Cl-4-F-Ph 4-Pyr SO₂Bu
10-550 3-Cl-4-F-Ph 4-Pyr SO₂CF_Three              
10-551 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-F         
10-552 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-OH        
10-553 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe       
10-554 3-Cl-4-F-Ph 4-Pyr SO₂NH₂              
10-555 3-Cl-4-F-Ph 4-Pyr SO₂NHMe
10-556 3-Cl-4-F-Ph 4-Pyr SO₂NHEt
10-557 3-Cl-4-F-Ph 4-Pyr SO₂NHPr
10-558 3-Cl-4-F-Ph 4-Pyr SO₂NH-i-Pr
10-559 3-Cl-4-F-Ph 4-Pyr SO₂NHBu
10-560 3-Cl-4-F-Ph 4-Pyr SO₂NHBn
10-561 3-Cl-4-F-Ph 4-Pyr SO₂NMe₂             
10-562 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Pr
10-563 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Bu
10-564 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Pen
10-565 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Hex
10-566 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Hep
10-567 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂-c-Pr
10-568 3-Cl-4-F-Ph 4-Pyr SO₂NH-Allyl
10-569 3-Cl-4-F-Ph 4-Pyr SO₂NH-Propargyl
10-570 3-Cl-4-F-Ph 4-Pyr SO₂NHPh
10-571 3-Cl-4-F-Ph 4-Pyr SO₂NH-3-Pyr
10-572 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr
10-573 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
10-574 3-Cl-4-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
10-575 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
10-576 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂CN           
10-577 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F
10-578 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
10-579 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
10-580 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
10-581 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
10-582 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
10-583 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂COOH
10-584 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂COOEt
10-585 3-Cl-4-F-Ph 4-Pyr SO₂NHCH (Me) COOEt
10-586 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂CONH₂        
10-587 3-Cl-4-F-Ph 4-Pyr SO₂NHOH
10-588 3-Cl-4-F-Ph 4-Pyr SO₂NHOMe
10-589 3-Cl-4-F-Ph 4-Pyr SO₂NHOEt
10-590 3-Cl-4-F-Ph 4-Pyr SO₂NHOPr
10-591 3-Cl-4-F-Ph 4-Pyr SO₂NHOAllyl
10-592 3-Cl-4-F-Ph 4-Pyr SO₂NHOBn
10-593 3-Cl-4-F-Ph 4-Pyr SO₂NHNH₂            
10-594 3-Cl-4-F-Ph 4-Pyr SO₂NHNHMe
10-595 3-Cl-4-F-Ph 4-Pyr SO₂NHN (Me)₂         
10-596 3,4-F₂-Ph 4-Pyr COOH
10-597 3,4-F₂-Ph 4-Pyr COOMe
10-598 3,4-F₂-Ph 4-Pyr COOEt
10-599 3,4-F₂-Ph 4-Pyr COOPr
10-600 3,4-F₂-Ph 4-Pyr COO-i-Pr
10-601 3,4-F₂-Ph 4-Pyr COOBu
10-602 3,4-F₂-Ph 4-Pyr COOBn
10-603 3,4-F₂-Ph 4-Pyr COOPh
10-604 3,4-F₂-Ph 4-Pyr CONH₂              
10-605 3,4-F₂-Ph 4-Pyr CONHMe
10-606 3,4-F₂-Ph 4-Pyr CONHEt
10-607 3,4-F₂-Ph 4-Pyr CONHPr
10-608 3,4-F₂-Ph 4-Pyr CONH-i-Pr
10-609 3,4-F₂-Ph 4-Pyr CONHBu
10-610 3,4-F₂-Ph 4-Pyr CONHBn
10-611 3,4-F₂-Ph 4-Pyr CONMe₂             
10-612 3,4-F₂-Ph 4-Pyr CONH-c-Pr
10-613 3,4-F₂-Ph 4-Pyr CONH-c-Bu
10-614 3,4-F₂-Ph 4-Pyr CONH-c-Pen
10-615 3,4-F₂-Ph 4-Pyr CONH-c-Hex
10-616 3,4-F₂-Ph 4-Pyr CONH-c-Hep
10-617 3,4-F₂-Ph 4-Pyr CONHCH₂-c-Pr
10-618 3,4-F₂-Ph 4-Pyr CONH-Allyl
10-619 3,4-F₂-Ph 4-Pyr CONH-Propargyl
10-620 3,4-F₂-Ph 4-Pyr CONHPh
10-621 3,4-F₂-Ph 4-Pyr CONH-3-Pyr
10-622 3,4-F₂-Ph 4-Pyr CONHCH₂-4-Pyr
10-623 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-OH
10-624 3,4-F₂-Ph 4-Pyr CONHCH (CH₂OH)₂      
10-625 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-OAc
10-626 3,4-F₂-Ph 4-Pyr CONHCH₂CN
10-627 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-F
10-628 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-OMe
10-629 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-SMe
10-630 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
10-631 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-NHMe
10-632 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
10-633 3,4-F₂-Ph 4-Pyr CONHCH₂COOH
10-634 3,4-F₂-Ph 4-Pyr CONHCH₂COOEt
10-635 3,4-F₂-Ph 4-Pyr CONHCH (Me) COOEt
10-636 3,4-F₂-Ph 4-Pyr CONHCH₂CONH₂        
10-637 3,4-F₂-Ph 4-Pyr CONHOH
10-638 3,4-F₂-Ph 4-Pyr CONHOMe
10-639 3,4-F₂-Ph 4-Pyr CONHOEt
10-640 3,4-F₂-Ph 4-Pyr CONHOPr
10-641 3,4-F₂-Ph 4-Pyr CONHOAllyl
10-642 3,4-F₂-Ph 4-Pyr CONHOBn
10-643 3,4-F₂-Ph 4-Pyr CONHNH₂            
10-644 3,4-F₂-Ph 4-Pyr CONHNHMe
10-645 3,4-F₂-Ph 4-Pyr CONHN (Me)₂          
10-646 3,4-F₂-Ph 4-Pyr COMe
10-647 3,4-F₂-Ph        4-Pyr COEt
10-648 3,4-F₂-Ph 4-Pyr COPr
10-649 3,4-F₂-Ph 4-Pyr CO-i-Pr
10-650 3,4-F₂-Ph 4-Pyr COBu
10-651 3,4-F₂-Ph 4-Pyr COCF_Three              
10-652 3,4-F₂-Ph 4-Pyr CO- (CH₂)₂-F          
10-653 3,4-F₂-Ph 4-Pyr CO- (CH₂)₂-OH         
10-654 3,4-F₂-Ph 4-Pyr CO- (CH₂)₂-OMe        
10-655 3,4-F₂-Ph 4-Pyr SOMe
10-656 3,4-F₂-Ph 4-Pyr SOEt
10-657 3,4-F₂-Ph 4-Pyr SOPr
10-658 3,4-F₂-Ph 4-Pyr SO-i-Pr
10-659 3,4-F₂-Ph 4-Pyr SOBu
10-660 3,4-F₂-Ph 4-Pyr SOCF_Three              
10-661 3,4-F₂-Ph 4-Pyr SO- (CH₂)₂-F         
10-662 3,4-F₂-Ph 4-Pyr SO- (CH₂)₂-OH        
10-663 3,4-F₂-Ph 4-Pyr SO- (CH₂)₂-OMe       
10-664 3,4-F₂-Ph 4-Pyr SO₂Me
10-665 3,4-F₂-Ph 4-Pyr SO₂Et
10-666 3,4-F₂-Ph 4-Pyr SO₂Pr
10-667 3,4-F₂-Ph 4-Pyr SO₂-i-Pr
10-668 3,4-F₂-Ph 4-Pyr SO₂Bu
10-669 3,4-F₂-Ph 4-Pyr SO₂CF_Three             
10-670 3,4-F₂-Ph 4-Pyr SO₂-(CH₂)₂-F         
10-671 3,4-F₂-Ph 4-Pyr SO₂-(CH₂)₂-OH        
10-672 3,4-F₂-Ph 4-Pyr SO₂-(CH₂)₂-OMe       
10-673 3,4-F₂-Ph 4-Pyr SO₂NH₂             
10-674 3,4-F₂-Ph 4-Pyr SO₂NHMe
10-675 3,4-F₂-Ph 4-Pyr SO₂NHEt
10-676 3,4-F₂-Ph 4-Pyr SO₂NHPr
10-677 3,4-F₂-Ph 4-Pyr SO₂NH-i-Pr
10-678 3,4-F₂-Ph 4-Pyr SO₂NHBu
10-679 3,4-F₂-Ph 4-Pyr SO₂NHBn
10-680 3,4-F₂-Ph 4-Pyr SO₂NMe₂            
10-681 3,4-F₂-Ph 4-Pyr SO₂NH-c-Pr
10-682 3,4-F₂-Ph 4-Pyr SO₂NH-c-Bu
10-683 3,4-F₂-Ph 4-Pyr SO₂NH-c-Pen
10-684 3,4-F₂-Ph        4-Pyr SO₂NH-c-Hex
10-685 3,4-F₂-Ph 4-Pyr SO₂NH-c-Hep
10-686 3,4-F₂-Ph 4-Pyr SO₂NHCH₂-c-Pr
10-687 3,4-F₂-Ph 4-Pyr SO₂NH-Allyl
10-688 3,4-F₂-Ph 4-Pyr SO₂NH-Propargyl
10-689 3,4-F₂-Ph 4-Pyr SO₂NHPh
10-690 3,4-F₂-Ph 4-Pyr SO₂NH-3-Pyr
10-691 3,4-F₂-Ph 4-Pyr SO₂NHCH₂-4-Pyr
10-692 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
10-693 3,4-F₂-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
10-694 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
10-695 3,4-F₂-Ph 4-Pyr SO₂NHCH₂CN
10-696 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-F
10-697 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
10-698 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
10-699 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
10-700 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
10-701 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
10-702 3,4-F₂-Ph 4-Pyr SO₂NHCH₂COOH
10-703 3,4-F₂-Ph 4-Pyr SO₂NHCH₂COOEt
10-704 3,4-F₂-Ph 4-Pyr SO₂NHCH (Me) COOEt
10-705 3,4-F₂-Ph 4-Pyr SO₂NHCH₂CONH₂        
10-706 3,4-F₂-Ph 4-Pyr SO₂NHOH
10-707 3,4-F₂-Ph 4-Pyr SO₂NHOMe
10-708 3,4-F₂-Ph 4-Pyr SO₂NHOEt
10-709 3,4-F₂-Ph 4-Pyr SO₂NHOPr
10-710 3,4-F₂-Ph 4-Pyr SO₂NHOAllyl
10-711 3,4-F₂-Ph 4-Pyr SO₂NHOBn
10-712 3,4-F₂-Ph 4-Pyr SO₂NHNH₂            
10-713 3,4-F₂-Ph 4-Pyr SO₂NHNHMe
10-714 3,4-F₂-Ph 4-Pyr SO₂NHN (Me)₂         
10-715 3-CF_Three-Ph 4-Pyr COOH
10-716 3-CF_Three-Ph 4-Pyr COOMe
10-717 3-CF_Three-Ph 4-Pyr COOEt
10-718 3-CF_Three-Ph 4-Pyr COOPr
10-719 3-CF_Three-Ph 4-Pyr COO-i-Pr
10-720 3-CF_Three-Ph 4-Pyr COOBu
10-721 3-CF_Three-Ph 4-Pyr COOBn
10-722 3-CF_Three-Ph 4-Pyr COOPh
10-723 3-CF_Three-Ph 4-Pyr CONH₂              
10-724 3-CF_Three-Ph 4-Pyr CONHMe
10-725 3-CF_Three-Ph 4-Pyr CONHEt
10-726 3-CF_Three-Ph 4-Pyr CONHPr
10-727 3-CF_Three-Ph 4-Pyr CONH-i-Pr
10-728 3-CF_Three-Ph 4-Pyr CONHBu
10-729 3-CF_Three-Ph 4-Pyr CONHBn
10-730 3-CF_Three-Ph 4-Pyr CONMe₂             
10-731 3-CF_Three-Ph 4-Pyr CONH-c-Pr
10-732 3-CF_Three-Ph 4-Pyr CONH-c-Bu
10-733 3-CF_Three-Ph 4-Pyr CONH-c-Pen
10-734 3-CF_Three-Ph 4-Pyr CONH-c-Hex
10-735 3-CF_Three-Ph 4-Pyr CONH-c-Hep
10-736 3-CF_Three-Ph 4-Pyr CONHCH₂-c-Pr
10-737 3-CF_Three-Ph 4-Pyr CONH-Allyl
10-738 3-CF_Three-Ph 4-Pyr CONH-Propargyl
10-739 3-CF_Three-Ph 4-Pyr CONHPh
10-740 3-CF_Three-Ph 4-Pyr CONH-3-Pyr
10-741 3-CF_Three-Ph 4-Pyr CONHCH₂-4-Pyr
10-742 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-OH
10-743 3-CF_Three-Ph 4-Pyr CONHCH (CH₂OH)₂      
10-744 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-OAc
10-745 3-CF_Three-Ph 4-Pyr CONHCH₂CN
10-746 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-F
10-747 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-OMe
10-748 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-SMe
10-749 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
10-750 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-NHMe
10-751 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
10-752 3-CF_Three-Ph 4-Pyr CONHCH₂COOH
10-753 3-CF_Three-Ph 4-Pyr CONHCH₂COOEt
10-754 3-CF_Three-Ph 4-Pyr CONHCH (Me) COOEt
10-755 3-CF_Three-Ph 4-Pyr CONHCH₂CONH₂        
10-756 3-CF_Three-Ph 4-Pyr CONHOH
10-757 3-CF_Three-Ph         4-Pyr CONHOMe
10-758 3-CF_Three-Ph 4-Pyr CONHOEt
10-759 3-CF_Three-Ph 4-Pyr CONHOPr
10-760 3-CF_Three-Ph 4-Pyr CONHOAllyl
10-761 3-CF_Three-Ph 4-Pyr CONHOBn
10-762 3-CF_Three-Ph 4-Pyr CONHNH₂            
10-763 3-CF_Three-Ph 4-Pyr CONHNHMe
10-764 3-CF_Three-Ph 4-Pyr CONHN (Me)₂          
10-765 3-CF_Three-Ph 4-Pyr COMe
10-766 3-CF_Three-Ph 4-Pyr COEt
10-767 3-CF_Three-Ph 4-Pyr COPr
10-768 3-CF_Three-Ph 4-Pyr CO-i-Pr
10-769 3-CF_Three-Ph 4-Pyr COBu
10-770 3-CF_Three-Ph 4-Pyr COCF_Three              
10-771 3-CF_Three-Ph 4-Pyr CO- (CH₂)₂-F          
10-772 3-CF_Three-Ph 4-Pyr CO- (CH₂)₂-OH         
10-773 3-CF_Three-Ph 4-Pyr CO- (CH₂)₂-OMe        
10-774 3-CF_Three-Ph 4-Pyr SOMe
10-775 3-CF_Three-Ph 4-Pyr SOEt
10-776 3-CF_Three-Ph 4-Pyr SOPr
10-777 3-CF_Three-Ph 4-Pyr SO-i-Pr
10-778 3-CF_Three-Ph 4-Pyr SOBu
10-779 3-CF_Three-Ph 4-Pyr SOCF_Three              
10-780 3-CF_Three-Ph 4-Pyr SO- (CH₂)₂-F         
10-781 3-CF_Three-Ph 4-Pyr SO- (CH₂)₂-OH        
10-782 3-CF_Three-Ph 4-Pyr SO- (CH₂)₂-OMe       
10-783 3-CF_Three-Ph 4-Pyr SO₂Me
10-784 3-CF_Three-Ph 4-Pyr SO₂Et
10-785 3-CF_Three-Ph 4-Pyr SO₂Pr
10-786 3-CF_Three-Ph 4-Pyr SO₂-i-Pr
10-787 3-CF_Three-Ph 4-Pyr SO₂Bu
10-788 3-CF_Three-Ph 4-Pyr SO₂CF_Three             
10-789 3-CF_Three-Ph 4-Pyr SO₂-(CH₂)₂-F
10-790 3-CF_Three-Ph 4-Pyr SO₂-(CH₂)₂-OH
10-791 3-CF_Three-Ph 4-Pyr SO₂-(CH₂)₂-OMe
10-792 3-CF_Three-Ph 4-Pyr SO₂NH₂             
10-793 3-CF_Three-Ph 4-Pyr SO₂NHMe
10-794 3-CF_Three-Ph 4-Pyr SO₂NHEt
10-795 3-CF_Three-Ph 4-Pyr SO₂NHPr
10-796 3-CF_Three-Ph 4-Pyr SO₂NH-i-Pr
10-797 3-CF_Three-Ph 4-Pyr SO₂NHBu
10-798 3-CF_Three-Ph 4-Pyr SO₂NHBn
10-799 3-CF_Three-Ph 4-Pyr SO₂NMe₂            
10-800 3-CF_Three-Ph 4-Pyr SO₂NH-c-Pr
10-801 3-CF_Three-Ph 4-Pyr SO₂NH-c-Bu
10-802 3-CF_Three-Ph 4-Pyr SO₂NH-c-Pen
10-803 3-CF_Three-Ph 4-Pyr SO₂NH-c-Hex
10-804 3-CF_Three-Ph 4-Pyr SO₂NH-c-Hep
10-805 3-CF_Three-Ph 4-Pyr SO₂NHCH₂-c-Pr
10-806 3-CF_Three-Ph 4-Pyr SO₂NH-Allyl
10-807 3-CF_Three-Ph 4-Pyr SO₂NH-Propargyl
10-808 3-CF_Three-Ph 4-Pyr SO₂NHPh
10-809 3-CF_Three-Ph 4-Pyr SO₂NH-3-Pyr
10-810 3-CF_Three-Ph 4-Pyr SO₂NHCH₂-4-Pyr
10-811 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
10-812 3-CF_Three-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
10-813 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
10-814 3-CF_Three-Ph 4-Pyr SO₂NHCH₂CN
10-815 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-F
10-816 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
10-817 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
10-818 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
10-819 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
10-820 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
10-821 3-CF_Three-Ph 4-Pyr SO₂NHCH₂COOH
10-822 3-CF_Three-Ph 4-Pyr SO₂NHCH₂COOEt
10-823 3-CF_Three-Ph 4-Pyr SO₂NHCH (Me) COOEt
10-824 3-CF_Three-Ph 4-Pyr SO₂NHCH₂CONH₂        
10-825 3-CF_Three-Ph 4-Pyr SO₂NHOH
10-826 3-CF_Three-Ph 4-Pyr SO₂NHOMe
10-827 3-CF_Three-Ph 4-Pyr SO₂NHOEt
10-828 3-CF_Three-Ph 4-Pyr SO₂NHOPr
10-829 3-CF_Three-Ph 4-Pyr SO₂NHOAllyl
10-830 3-CF_Three-Ph 4-Pyr SO₂NHOBn
10-831 3-CF_Three-Ph 4-Pyr SO₂NHNH₂            
10-832 3-CF_Three-Ph 4-Pyr SO₂NHNHMe
10-833 3-CF_Three-Ph 4-Pyr SO₂NHN (Me)₂        
10-834 4-F-Ph 4-Pym CONH₂              
10-835 4-F-Ph 4-Pym CONHMe
10-836 4-F-Ph 4-Pym CONHEt
10-837 4-F-Ph 4-Pym CONHPr
10-838 4-F-Ph 4-Pym CONH-i-Pr
10-839 4-F-Ph 4-Pym CONHBu
10-840 4-F-Ph 4-Pym CONHBn
10-841 4-F-Ph 4-Pym CONMe₂              
10-842 4-F-Ph 4-Pym CONH-c-Pr
10-843 4-F-Ph 4-Pym CONH-c-Bu
10-844 4-F-Ph 4-Pym CONH-c-Pen
10-845 4-F-Ph 4-Pym CONH-c-Hex
10-846 4-F-Ph 4-Pym CONH-c-Hep
10-847 4-F-Ph 4-Pym CONHCH₂-c-Pr         
10-848 4-F-Ph 4-Pym CONH-Allyl
10-849 4-F-Ph 4-Pym CONH-Propargyl
10-850 4-F-Ph 4-Pym CONHPh
10-851 4-F-Ph 4-Pym CONH-3-Pyr
10-852 4-F-Ph 4-Pym CONHCH₂-4-Pyr
10-853 4-F-Ph 4-Pym CONH- (CH₂)₂-OH
10-854 4-F-Ph 4-Pym CONHCH (CH₂OH)₂       
10-855 4-F-Ph 4-Pym CONH- (CH₂)₂-OAc
10-856 4-F-Ph 4-Pym CONHCH₂CN
10-857 4-F-Ph 4-Pym CONH- (CH₂)₂-F
10-858 4-F-Ph 4-Pym CONH- (CH₂)₂-OMe
10-859 4-F-Ph 4-Pym CONH- (CH₂)₂-SMe
10-860 4-F-Ph 4-Pym CONH- (CH₂)₂-NH₂     
10-861 4-F-Ph 4-Pym CONH- (CH₂)₂-NHMe
10-862 4-F-Ph 4-Pym CONH- (CH₂)₂-N (Me)₂  
10-863 4-F-Ph 4-Pym CONHCH₂COOH
10-864 4-F-Ph 4-Pym CONHCH₂COOEt         
10-865 4-F-Ph 4-Pym CONHCH (Me) COOEt
10-866 4-F-Ph 4-Pym CONHCH₂CONH₂        
10-867 4-F-Ph 4-Pym SO₂NH₂              
10-868 4-F-Ph 4-Pym SO₂NHMe
10-869 4-F-Ph 4-Pym SO₂NHEt
10-870 4-F-Ph 4-Pym SO₂NHPr
10-871 4-F-Ph 4-Pym SO₂NH-i-Pr
10-872 4-F-Ph 4-Pym SO₂NHBu
10-873 4-F-Ph 4-Pym SO₂NHBn
10-874 4-F-Ph 4-Pym SO₂NMe₂             
10-875 4-F-Ph 4-Pym SO₂NH-c-Pr
10-876 4-F-Ph 4-Pym SO₂NH-c-Bu
10-877 4-F-Ph 4-Pym SO₂NH-c-Pen
10-878 4-F-Ph 4-Pym SO₂NH-c-Hex
10-879 4-F-Ph 4-Pym SO₂NH-c-Hep
10-880 4-F-Ph 4-Pym SO₂NHCH₂-c-Pr
10-881 4-F-Ph 4-Pym SO₂NH-Allyl
10-882 4-F-Ph 4-Pym SO₂NH-Propargyl
10-883 4-F-Ph 4-Pym SO₂NHPh
10-884 4-F-Ph 4-Pym SO₂NH-3-Pyr
10-885 4-F-Ph 4-Pym SO₂NHCH₂-4-Pyr
10-886 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OH
10-887 4-F-Ph 4-Pym SO₂NHCH (CH₂OH)₂      
10-888 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OAc
10-889 4-F-Ph 4-Pym SO₂NHCH₂CN
10-890 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-F
10-891 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OMe
10-892 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-SMe
10-893 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-NH₂     
10-894 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-NHMe
10-895 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
10-896 4-F-Ph 4-Pym SO₂NHCH₂COOH
10-897 4-F-Ph 4-Pym SO₂NHCH₂COOEt
10-898 4-F-Ph 4-Pym SO₂NHCH (Me) COOEt
10-899 4-F-Ph 4-Pym SO₂NHCH₂CONH₂        
10-900 4-F-Ph 4-Pym SO₂NHOH
10-901 4-F-Ph 4-Pym SO₂NHOMe
10-902 4-F-Ph 4-Pym SO₂NHOEt
10-903 4-F-Ph 4-Pym SO₂NHOPr
10-904 4-F-Ph 4-Pym SO₂NHOAllyl
10-905 4-F-Ph 4-Pym SO₂NHOBn
10-906 4-F-Ph 4-Pym SO₂NHNH₂            
10-907 4-F-Ph 4-Pym SO₂NHNHMe
10-908 4-F-Ph 4-Pym SO₂NHN (Me)₂         
10-909 4-F-Ph 2-MeO-4-Pym CONH₂              
10-910 4-F-Ph 2-MeO-4-Pym CONHMe
10-911 4-F-Ph 2-MeO-4-Pym CONHEt
10-912 4-F-Ph 2-MeO-4-Pym CONHPr
10-913 4-F-Ph 2-MeO-4-Pym CONH-i-Pr
10-914 4-F-Ph 2-MeO-4-Pym CONHBu
10-915 4-F-Ph 2-MeO-4-Pym CONHBn
10-916 4-F-Ph 2-MeO-4-Pym CONMe₂             
10-917 4-F-Ph 2-MeO-4-Pym CONH-c-Pr
10-918 4-F-Ph 2-MeO-4-Pym CONH-c-Bu
10-919 4-F-Ph 2-MeO-4-Pym CONH-c-Pen
10-920 4-F-Ph 2-MeO-4-Pym CONH-c-Hex
10-921 4-F-Ph 2-MeO-4-Pym CONH-c-Hep
10-922 4-F-Ph 2-MeO-4-Pym CONHCH₂-c-Pr
10-923 4-F-Ph 2-MeO-4-Pym CONH-Allyl
10-924 4-F-Ph 2-MeO-4-Pym CONH-Propargyl
10-925 4-F-Ph 2-MeO-4-Pym CONHPh
10-926 4-F-Ph 2-MeO-4-Pym CONH-3-Pyr
10-927 4-F-Ph 2-MeO-4-Pym CONHCH₂-4-Pyr
10-928 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OH
10-929 4-F-Ph 2-MeO-4-Pym CONHCH (CH₂OH)₂       
10-930 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OAc
10-931 4-F-Ph 2-MeO-4-Pym CONHCH₂CN            
10-932 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-F
10-933 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OMe
10-934 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-SMe
10-935 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-NH₂      
10-936 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-NHMe
10-937 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-N (Me)₂   
10-938 4-F-Ph 2-MeO-4-Pym CONHCH₂COOH          
10-939 4-F-Ph 2-MeO-4-Pym CONHCH₂COOEt         
10-940 4-F-Ph 2-MeO-4-Pym CONHCH (Me) COOEt
10-941 4-F-Ph 2-MeO-4-Pym CONHCH₂CONH₂        
10-942 4-F-Ph 2-MeO-4-Pym SO₂NH₂              
10-943 4-F-Ph 2-MeO-4-Pym SO₂NHMe             
10-944 4-F-Ph 2-MeO-4-Pym SO₂NHEt             
10-945 4-F-Ph 2-MeO-4-Pym SO₂NHPr             
10-946 4-F-Ph 2-MeO-4-Pym SO₂NH-i-Pr          
10-947 4-F-Ph 2-MeO-4-Pym SO₂NHBu             
10-948 4-F-Ph 2-MeO-4-Pym SO₂NHBn             
10-949 4-F-Ph 2-MeO-4-Pym SO₂NMe₂             
10-950 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Pr          
10-951 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Bu
10-952 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Pen
10-953 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Hex
10-954 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Hep
10-955 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂-c-Pr
10-956 4-F-Ph 2-MeO-4-Pym SO₂NH-Allyl          
10-957 4-F-Ph 2-MeO-4-Pym SO₂NH-Propargyl      
10-958 4-F-Ph 2-MeO-4-Pym SO₂NHPh              
10-959 4-F-Ph 2-MeO-4-Pym SO₂NH-3-Pyr          
10-960 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂-4-Pyr
10-961 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OH      
10-962 4-F-Ph 2-MeO-4-Pym SO₂NHCH (CH₂OH)₂     
10-963 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OAc     
10-964 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂CN           
10-965 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-F
10-966 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OMe
10-967 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-SMe
10-968 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-NH₂     
10-969 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-NHMe
10-970 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
10-971 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂COOH
10-972 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂COOEt
10-973 4-F-Ph 2-MeO-4-Pym SO₂NHCH (Me) COOEt     
10-974 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂CONH₂       
10-975 4-F-Ph 2-MeO-4-Pym SO₂NHOH             
10-976 4-F-Ph 2-MeO-4-Pym SO₂NHOMe
10-977 4-F-Ph 2-MeO-4-Pym SO₂NHOEt
10-978 4-F-Ph 2-MeO-4-Pym SO₂NHOPr
10-979 4-F-Ph 2-MeO-4-Pym SO₂NHOAllyl
10-980 4-F-Ph 2-MeO-4-Pym SO₂NHOBn
10-981 4-F-Ph 2-MeO-4-Pym SO₂NHNH₂            
10-982 4-F-Ph 2-MeO-4-Pym SO₂NHNHMe
10-983 4-F-Ph 2-MeO-4-Pym SO₂NHN (Me)₂         
10-984 4-F-Ph 2-NH₂-4-Pym             CONH₂              
10-985 4-F-Ph 2-NH₂-4-Pym             CONHMe
10-986 4-F-Ph 2-NH₂-4-Pym             CONHEt
10-987 4-F-Ph 2-NH₂-4-Pym             CONHPr
10-988 4-F-Ph 2-NH₂-4-Pym CONH-i-Pr
10-989 4-F-Ph 2-NH₂-4-Pym             CONHBu
10-990 4-F-Ph 2-NH₂-4-Pym             CONHBn
10-991 4-F-Ph 2-NH₂-4-Pym             CONMe₂              
10-992 4-F-Ph 2-NH₂-4-Pym             CONH-c-Pr
10-993 4-F-Ph 2-NH₂-4-Pym             CONH-c-Bu
10-994 4-F-Ph 2-NH₂-4-Pym             CONH-c-Pen
10-995 4-F-Ph 2-NH₂-4-Pym             CONH-c-Hex
10-996 4-F-Ph 2-NH₂-4-Pym             CONH-c-Hep
10-997 4-F-Ph 2-NH₂-4-Pym             CONHCH₂-c-Pr
10-998 4-F-Ph 2-NH₂-4-Pym             CONH-Allyl
10-999 4-F-Ph 2-NH₂-4-Pym CONH-Propargyl
10-1000 4-F-Ph 2-NH₂-4-Pym CONHPh
10-1001 4-F-Ph 2-NH₂-4-Pym CONH-3-Pyr
10-1002 4-F-Ph 2-NH₂-4-Pym CONHCH₂-4-Pyr
10-1003 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OH
10-1004 4-F-Ph 2-NH₂-4-Pym CONHCH (CH₂OH)₂      
10-1005 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OAc
10-1006 4-F-Ph 2-NH₂-4-Pym CONHCH₂CN
10-1007 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-F
10-1008 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OMe
10-1009 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-SMe
10-1010 4-F-Ph 2-NH₂-4-Pym             CONH- (CH₂)₂-NH₂      
10-1011 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-NHMe
10-1012 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-N (Me)₂   
10-1013 4-F-Ph 2-NH₂-4-Pym CONHCH₂COOH
10-1014 4-F-Ph 2-NH₂-4-Pym CONHCH₂COOEt
10-1015 4-F-Ph 2-NH₂-4-Pym CONHCH (Me) COOEt
10-1016 4-F-Ph 2-NH₂-4-Pym CONHCH₂CONH₂        
10-1017 4-F-Ph 2-NH₂-4-Pym SO₂NH₂             
10-1018 4-F-Ph 2-NH₂-4-Pym SO₂NHMe
10-1019 4-F-Ph 2-NH₂-4-Pym SO₂NHEt
10-1020 4-F-Ph 2-NH₂-4-Pym SO₂NHPr
10-1021 4-F-Ph 2-NH₂-4-Pym SO₂NH-i-Pr
10-1022 4-F-Ph 2-NH₂-4-Pym SO₂NHBu
10-1023 4-F-Ph 2-NH₂-4-Pym SO₂NHBn
10-1024 4-F-Ph 2-NH₂-4-Pym SO₂NMe₂            
10-1025 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Pr
10-1026 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Bu
10-1027 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Pen
10-1028 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Hex
10-1029 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Hep
10-1030 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂-c-Pr
10-1031 4-F-Ph 2-NH₂-4-Pym SO₂NH-Allyl
10-1032 4-F-Ph 2-NH₂-4-Pym SO₂NH-Propargyl
10-1033 4-F-Ph 2-NH₂-4-Pym SO₂NHPh
10-1034 4-F-Ph 2-NH₂-4-Pym SO₂NH-3-Pyr
10-1035 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂-4-Pyr
10-1036 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OH
10-1037 4-F-Ph 2-NH₂-4-Pym SO₂NHCH (CH₂OH)₂      
10-1038 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OAc
10-1039 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂CN
10-1040 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-F
10-1041 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OMe
10-1042 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-SMe
10-1043 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-NH₂     
10-1044 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-NHMe
10-1045 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
10-1046 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂COOH
10-1047 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂COOEt
10-1048 4-F-Ph 2-NH₂-4-Pym SO₂NHCH (Me) COOEt
10-1049 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂CONH₂        
10-1050 4-F-Ph 2-NH₂-4-Pym SO₂NHOH
10-1051 4-F-Ph 2-NH₂-4-Pym SO₂NHOMe
10-1052 4-F-Ph 2-NH₂-4-Pym SO₂NHOEt
10-1053 4-F-Ph 2-NH₂-4-Pym SO₂NHOPr
10-1054 4-F-Ph 2-NH₂-4-Pym SO₂NHOAllyl
10-1055 4-F-Ph 2-NH₂-4-Pym SO₂NHOBn
10-1056 4-F-Ph 2-NH₂-4-Pym SO₂NHNH₂            
10-1057 4-F-Ph 2-NH₂-4-Pym SO₂NHNHMe
10-1058 4-F-Ph 2-NH₂-4-Pym SO₂NHN (Me)₂        
10-1059 4-F-Ph 2-MeNH-4-Pym CONH₂              
10-1060 4-F-Ph 2-MeNH-4-Pym CONHMe
10-1061 4-F-Ph 2-MeNH-4-Pym CONHEt
10-1062 4-F-Ph 2-MeNH-4-Pym CONHPr
10-1063 4-F-Ph 2-MeNH-4-Pym CONH-i-Pr
10-1064 4-F-Ph 2-MeNH-4-Pym CONHBu
10-1065 4-F-Ph 2-MeNH-4-Pym CONHBn
10-1066 4-F-Ph 2-MeNH-4-Pym CONMe₂              
10-1067 4-F-Ph 2-MeNH-4-Pym CONH-c-Pr
10-1068 4-F-Ph 2-MeNH-4-Pym CONH-c-Bu
10-1069 4-F-Ph 2-MeNH-4-Pym CONH-c-Pen
10-1070 4-F-Ph 2-MeNH-4-Pym CONH-c-Hex
10-1071 4-F-Ph 2-MeNH-4-Pym CONH-c-Hep
10-1072 4-F-Ph 2-MeNH-4-Pym CONHCH₂-c-Pr
10-1073 4-F-Ph 2-MeNH-4-Pym CONH-Allyl
10-1074 4-F-Ph 2-MeNH-4-Pym CONH-Propargyl
10-1075 4-F-Ph 2-MeNH-4-Pym CONHPh
10-1076 4-F-Ph 2-MeNH-4-Pym CONH-3-Pyr
10-1077 4-F-Ph 2-MeNH-4-Pym CONHCH₂-4-Pyr
10-1078 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OH
10-1079 4-F-Ph 2-MeNH-4-Pym CONHCH (CH₂OH)₂       
10-1080 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OAc
10-1081 4-F-Ph 2-MeNH-4-Pym CONHCH₂CN
10-1082 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-F
10-1083 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OMe
10-1084 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-SMe
10-1085 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-NH₂      
10-1086 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-NHMe
10-1087 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-N (Me)₂   
10-1088 4-F-Ph 2-MeNH-4-Pym CONHCH₂COOH
10-1089 4-F-Ph 2-MeNH-4-Pym CONHCH₂COOEt
10-1090 4-F-Ph 2-MeNH-4-Pym CONHCH (Me) COOEt
10-1091 4-F-Ph 2-MeNH-4-Pym CONHCH₂CONH₂        
10-1092 4-F-Ph 2-MeNH-4-Pym SO₂NH₂              
10-1093 4-F-Ph 2-MeNH-4-Pym SO₂NHMe
10-1094 4-F-Ph 2-MeNH-4-Pym SO₂NHEt
10-1095 4-F-Ph 2-MeNH-4-Pym SO₂NHPr
10-1096 4-F-Ph 2-MeNH-4-Pym SO₂NH-i-Pr
10-1097 4-F-Ph 2-MeNH-4-Pym SO₂NHBu
10-1098 4-F-Ph 2-MeNH-4-Pym SO₂NHBn
10-1099 4-F-Ph 2-MeNH-4-Pym SO₂NMe₂             
10-1100 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Pr
10-1101 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Bu
10-1102 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Pen
10-1103 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Hex
10-1104 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Hep
10-1105 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂-c-Pr
10-1106 4-F-Ph 2-MeNH-4-Pym SO₂NH-Allyl
10-1107 4-F-Ph 2-MeNH-4-Pym SO₂NH-Propargyl
10-1108 4-F-Ph 2-MeNH-4-Pym SO₂NHPh
10-1109 4-F-Ph 2-MeNH-4-Pym SO₂NH-3-Pyr
10-1110 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂-4-Pyr
10-1111 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OH
10-1112 4-F-Ph 2-MeNH-4-Pym SO₂NHCH (CH₂OH)₂     
10-1113 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OAc
10-1114 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂CN
10-1115 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-F       
10-1116 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OMe     
10-1117 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-SMe     
10-1118 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-NH₂     
10-1119 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-NHMe    
10-1120 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
10-1121 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂COOH        
10-1122 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂COOEt       
10-1123 4-F-Ph 2-MeNH-4-Pym SO₂NHCH (Me) COOEt    
10-1124 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂CONH₂       
10-1125 4-F-Ph 2-MeNH-4-Pym SO₂NHOH
10-1126 4-F-Ph 2-MeNH-4-Pym SO₂NHOMe
10-1127 4-F-Ph 2-MeNH-4-Pym SO₂NHOEt
10-1128 4-F-Ph 2-MeNH-4-Pym SO₂NHOPr
10-1129 4-F-Ph 2-MeNH-4-Pym SO₂NHOAllyl
10-1130 4-F-Ph 2-MeNH-4-Pym SO₂NHOBn
10-1131 4-F-Ph 2-MeNH-4-Pym SO₂NHNH₂            
10-1132 4-F-Ph 2-MeNH-4-Pym SO₂NHNHMe
10-1133 4-F-Ph 2-MeNH-4-Pym SO₂NHN (Me)₂         
10-1134 4-F-Ph 2-BnNH-4-Pym CONH₂               
10-1135 4-F-Ph 2-BnNH-4-Pym CONHMe
10-1136 4-F-Ph 2-BnNH-4-Pym CONHEt
10-1137 4-F-Ph 2-BnNH-4-Pym CONHPr
10-1138 4-F-Ph 2-BnNH-4-Pym CONH-i-Pr
10-1139 4-F-Ph 2-BnNH-4-Pym CONHBu
10-1140 4-F-Ph 2-BnNH-4-Pym CONHBn
10-1141 4-F-Ph 2-BnNH-4-Pym CONMe₂             
10-1142 4-F-Ph 2-BnNH-4-Pym CONH-c-Pr
10-1143 4-F-Ph 2-BnNH-4-Pym CONH-c-Bu
10-1144 4-F-Ph 2-BnNH-4-Pym CONH-c-Pen
10-1145 4-F-Ph 2-BnNH-4-Pym CONH-c-Hex
10-1146 4-F-Ph 2-BnNH-4-Pym CONH-c-Hep
10-1147 4-F-Ph 2-BnNH-4-Pym CONHCH₂-c-Pr
10-1148 4-F-Ph 2-BnNH-4-Pym CONH-Allyl
10-1149 4-F-Ph 2-BnNH-4-Pym CONH-Propargyl
10-1150 4-F-Ph 2-BnNH-4-Pym CONHPh
10-1151 4-F-Ph 2-BnNH-4-Pym CONH-3-Pyr
10-1152 4-F-Ph 2-BnNH-4-Pym CONHCH₂-4-Pyr
10-1153 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OH
10-1154 4-F-Ph 2-BnNH-4-Pym CONHCH (CH₂OH)₂       
10-1155 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OAc
10-1156 4-F-Ph 2-BnNH-4-Pym CONHCH₂CN            
10-1157 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-F
10-1158 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OMe
10-1159 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-SMe
10-1160 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-NH₂      
10-1161 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-NHMe
10-1162 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-N (Me)₂  
10-1163 4-F-Ph 2-BnNH-4-Pym CONHCH₂COOH          
10-1164 4-F-Ph 2-BnNH-4-Pym CONHCH₂COOEt         
10-1165 4-F-Ph 2-BnNH-4-Pym CONHCH (Me) COOEt
10-1166 4-F-Ph 2-BnNH-4-Pym CONHCH₂CONH₂         
10-1167 4-F-Ph 2-BnNH-4-Pym SO₂NH₂              
10-1168 4-F-Ph 2-BnNH-4-Pym SO₂NHMe
10-1169 4-F-Ph 2-BnNH-4-Pym SO₂NHEt
10-1170 4-F-Ph 2-BnNH-4-Pym SO₂NHPr
10-1171 4-F-Ph 2-BnNH-4-Pym SO₂NH-i-Pr
10-1172 4-F-Ph 2-BnNH-4-Pym SO₂NHBu
10-1173 4-F-Ph 2-BnNH-4-Pym SO₂NHBn
10-1174 4-F-Ph 2-BnNH-4-Pym SO₂NMe₂             
10-1175 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Pr
10-1176 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Bu
10-1177 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Pen
10-1178 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Hex
10-1179 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Hep
10-1180 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂-c-Pr
10-1181 4-F-Ph 2-BnNH-4-Pym SO₂NH-Allyl
10-1182 4-F-Ph 2-BnNH-4-Pym SO₂NH-Propargyl
10-1183 4-F-Ph 2-BnNH-4-Pym SO₂NHPh
10-1184 4-F-Ph 2-BnNH-4-Pym SO₂NH-3-Pyr
10-1185 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂-4-Pyr
10-1186 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OH
10-1187 4-F-Ph 2-BnNH-4-Pym SO₂NHCH (CH₂OH)₂      
10-1188 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OAc
10-1189 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂CN
10-1190 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-F
10-1191 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OMe
10-1192 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-SMe
10-1193 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-NH₂     
10-1194 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-NHMe
10-1195 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
10-1196 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂COOH         
10-1197 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂COOEt
10-1198 4-F-Ph 2-BnNH-4-Pym SO₂NHCH (Me) COOEt     
10-1199 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂CONH₂       
10-1200 4-F-Ph 2-BnNH-4-Pym SO₂NHOH
10-1201 4-F-Ph 2-BnNH-4-Pym SO₂NHOMe
10-1202 4-F-Ph 2-BnNH-4-Pym SO₂NHOEt
10-1203 4-F-Ph 2-BnNH-4-Pym SO₂NHOPr
10-1204 4-F-Ph 2-BnNH-4-Pym SO₂NHOAllyl
10-1205 4-F-Ph 2-BnNH-4-Pym SO₂NHOBn
10-1206 4-F-Ph 2-BnNH-4-Pym SO₂NHNH₂            
10-1207 4-F-Ph 2-BnNH-4-Pym SO₂NHNHMe
10-1208 4-F-Ph 2-BnNH-4-Pym SO₂NHN (Me)₂          
10-1209 4-F-Ph (α-Me-BnNH) -4-Pym CONH₂              
10-1210 4-F-Ph (α-Me-BnNH) -4-Pym CONHMe
10-1211 4-F-Ph (α-Me-BnNH) -4-Pym CONHEt
10-1212 4-F-Ph (α-Me-BnNH) -4-Pym CONHPr
10-1213 4-F-Ph (α-Me-BnNH) -4-Pym CONH-i-Pr
10-1214 4-F-Ph (α-Me-BnNH) -4-Pym CONHBu
10-1215 4-F-Ph (α-Me-BnNH) -4-Pym CONHBn
10-1216 4-F-Ph (α-Me-BnNH) -4-Pym CONMe₂             
10-1217 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Pr
10-1218 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Bu
10-1219 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Pen
10-1220 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Hex
10-1221 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Hep
10-1222 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂-c-Pr
10-1223 4-F-Ph (α-Me-BnNH) -4-Pym CONH-Allyl
10-1224 4-F-Ph (α-Me-BnNH) -4-Pym CONH-Propargyl
10-1225 4-F-Ph (α-Me-BnNH) -4-Pym CONHPh
10-1226 4-F-Ph (α-Me-BnNH) -4-Pym CONH-3-Pyr
10-1227 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂-4-Pyr        
10-1228 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OH
10-1229 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH (CH₂OH)₂       
10-1230 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OAc
10-1231 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂CN            
10-1232 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-F
10-1233 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OMe
10-1234 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-SMe
10-1235 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-NH₂      
10-1236 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-NHMe
10-1237 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-N (Me)₂  
10-1238 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂COOH
10-1239 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂COOEt
10-1240 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH (Me) COOEt
10-1241 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂CONH₂        
10-1242 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH₂              
10-1243 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHMe
10-1244 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHEt
10-1245 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHPr
10-1246 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-i-Pr
10-1247 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHBu
10-1248 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHBn
10-1249 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NMe₂             
10-1250 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Pr
10-1251 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Bu
10-1252 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Pen
10-1253 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Hex
10-1254 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Hep
10-1255 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂-c-Pr
10-1256 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-Allyl
10-1257 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-Propargyl
10-1258 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHPh
10-1259 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-3-Pyr
10-1260 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂-4-Pyr
10-1261 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OH
10-1262 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH (CH₂OH)₂      
10-1263 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OAc
10-1264 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂CN
10-1265 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-F
10-1266 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OMe
10-1267 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-SMe
10-1268 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-NH₂     
10-1269 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-NHMe
10-1270 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
10-1271 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂COOH
10-1272 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂COOEt
10-1273 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH (Me) COOEt
10-1274 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂CONH₂        
10-1275 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOH
10-1276 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOMe
10-1277 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOEt
10-1278 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOPr
10-1279 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOAllyl
10-1280 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOBn
10-1281 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHNH₂            
10-1282 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHNHMe           
10-1283 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHN (Me)₂          
10-1284 4-F-Ph 4-Pyr SO₂NHMe               
10-1285 4-F-Ph 4-Pyr SOMe                  
10-1286 4-F-Ph 4-Pyr SO₂Me                 
10-1287 3-Cl-4-F-Ph 4-Pyr SO₂NHMe               
10-1288 3-Cl-4-F-Ph 4-Pyr SOMe                  
10-1289 3-Cl-4-F-Ph 4-Pyr SO₂Me                 
―――――――――――――――――――――――――――――――――――
Table 11

―――――――――――――――――――――――――――――――――――
Compound R¹           R²                 R⁵ 
Number
―――――――――――――――――――――――――――――――――――
11-1 Ph 4-Pyr COOH
11-2 Ph 4-Pyr COOMe
11-3 Ph 4-Pyr COOEt
11-4 Ph 4-Pyr COOPr
11-5 Ph 4-Pyr COO-i-Pr
11-6 Ph 4-Pyr COOBu
11-7 Ph 4-Pyr COOBn
11-8 Ph 4-Pyr COOPh
11-9 Ph 4-Pyr CONH₂              
11-10 Ph 4-Pyr CONHMe
11-11 Ph 4-Pyr CONHEt
11-12 Ph 4-Pyr CONHPr
11-13 Ph 4-Pyr CONH-i-Pr
11-14 Ph 4-Pyr CONHBu
11-15 Ph 4-Pyr CONHBn
11-16 Ph 4-Pyr CONMe₂             
11-17 Ph 4-Pyr CONH-c-Pr
11-18 Ph 4-Pyr CONH-c-Bu
11-19 Ph 4-Pyr CONH-c-Pen
11-20 Ph 4-Pyr CONH-c-Hex
11-21 Ph 4-Pyr CONH-c-Hep
11-22 Ph 4-Pyr CONHCH₂-c-Pr
11-23 Ph 4-Pyr CONH-Allyl
11-24 Ph 4-Pyr CONH-Propargyl
11-25 Ph 4-Pyr CONHPh
11-26 Ph 4-Pyr CONH-3-Pyr
11-27 Ph 4-Pyr CONHCH₂-4-Pyr
11-28 Ph 4-Pyr CONH- (CH₂)₂-OH
11-29 Ph 4-Pyr CONHCH (CH₂OH)₂       
11-30 Ph 4-Pyr CONH- (CH₂)₂-OAc
11-31 Ph 4-Pyr CONHCH₂CN
11-32 Ph 4-Pyr CONH- (CH₂)₂-F
11-33 Ph 4-Pyr CONH- (CH₂)₂-OMe
11-34 Ph 4-Pyr CONH- (CH₂)₂-SMe
11-35 Ph 4-Pyr CONH- (CH₂)₂-NH₂      
11-36 Ph 4-Pyr CONH- (CH₂)₂-NHMe
11-37 Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
11-38 Ph 4-Pyr CONHCH₂COOH
11-39 Ph 4-Pyr CONHCH₂COOEt
11-40 Ph 4-Pyr CONHCH (Me) COOEt
11-41 Ph 4-Pyr CONHCH₂CONH₂         
11-42 Ph 4-Pyr CONHOH
11-43 Ph 4-Pyr CONHOMe
11-44 Ph 4-Pyr CONHOEt
11-45 Ph 4-Pyr CONHOPr
11-46 Ph 4-Pyr CONHO-Allyl
11-47 Ph 4-Pyr CONHOBn
11-48 Ph 4-Pyr CONHNH₂            
11-49 Ph 4-Pyr CONHNHMe
11-50 Ph 4-Pyr CONHN (Me)₂          
11-51 Ph 4-Pyr COMe
11-52 Ph 4-Pyr COEt
11-53 Ph 4-Pyr COPr
11-54 Ph 4-Pyr CO-i-Pr
11-55 Ph 4-Pyr COBu
11-56 Ph 4-Pyr COCF_Three               
11-57 Ph 4-Pyr CO- (CH₂)₂-F
11-58 Ph 4-Pyr CO- (CH₂)₂-OH
11-59 Ph 4-Pyr CO- (CH₂)₂-OMe
11-60 Ph 4-Pyr SOMe
11-61 Ph 4-Pyr SOEt
11-62 Ph 4-Pyr SOPr
11-63 Ph 4-Pyr SO-i-Pr
11-64 Ph 4-Pyr SOBu
11-65 Ph 4-Pyr SOCF_Three              
11-66 Ph 4-Pyr SO- (CH₂)₂-F
11-67 Ph 4-Pyr SO- (CH₂)₂-OH
11-68 Ph 4-Pyr SO- (CH₂)₂-OMe
11-69 Ph 4-Pyr SO₂Me
11-70 Ph 4-Pyr SO₂Et
11-71 Ph 4-Pyr SO₂Pr
11-72 Ph 4-Pyr SO₂-i-Pr
11-73 Ph 4-Pyr SO₂Bu
11-74 Ph 4-Pyr SO₂CF_Three              
11-75 Ph 4-Pyr SO₂-(CH₂)₂-F
11-76 Ph 4-Pyr SO₂-(CH₂)₂-OH
11-77 Ph 4-Pyr SO₂-(CH₂)₂-OMe
11-78 Ph 4-Pyr SO₂NH₂              
11-79 Ph 4-Pyr SO₂NHMe
11-80 Ph 4-Pyr SO₂NHEt
11-81 Ph 4-Pyr SO₂NHPr
11-82 Ph 4-Pyr SO₂NH-i-Pr
11-83 Ph 4-Pyr SO₂NHBu
11-84 Ph 4-Pyr SO₂NHBn
11-85 Ph 4-Pyr SO₂NMe₂             
11-86 Ph 4-Pyr SO₂NH-c-Pr
11-87 Ph 4-Pyr SO₂NH-c-Bu
11-88 Ph 4-Pyr SO₂NH-c-Pen
11-89 Ph 4-Pyr SO₂NH-c-Hex
11-90 Ph 4-Pyr SO₂NH-c-Hep
11-91 Ph 4-Pyr SO₂NHCH₂-c-Pr
11-92 Ph 4-Pyr SO₂NH-Allyl
11-93 Ph 4-Pyr SO₂NH-Propargyl
11-94 Ph 4-Pyr SO₂NHPh
11-95 Ph 4-Pyr SO₂NH-3-Pyr
11-96 Ph 4-Pyr SO₂NHCH₂-4-Pyr
11-97 Ph 4-Pyr SO₂NH- (CH₂)₂-OH
11-98 Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
11-99 Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
11-100 Ph 4-Pyr SO₂NHCH₂CN
11-101 Ph 4-Pyr SO₂NH- (CH₂)₂-F
11-102 Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
11-103 Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
11-104 Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
11-105 Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
11-106 Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
11-107 Ph 4-Pyr SO₂NHCH₂COOH
11-108 Ph 4-Pyr SO₂NHCH₂COOEt
11-109 Ph 4-Pyr SO₂NHCH (Me) COOEt
11-110 Ph 4-Pyr SO₂NHCH₂CONH₂        
11-111 Ph 4-Pyr SO₂NHOH
11-112 Ph 4-Pyr SO₂NHOMe
11-113 Ph 4-Pyr SO₂NHOEt
11-114 Ph 4-Pyr SO₂NHOPr
11-115 Ph 4-Pyr SO₂NHOAllyl
11-116 Ph 4-Pyr SO₂NHOBn
11-117 Ph 4-Pyr SO₂NHNH₂            
11-118 Ph 4-Pyr SO₂NHNHMe
11-119 Ph 4-Pyr SO₂NHN (Me)₂          
11-120 3-F-Ph 4-Pyr COOH
11-121 3-F-Ph 4-Pyr COOMe
11-122 3-F-Ph 4-Pyr COOEt
11-123 3-F-Ph 4-Pyr COOPr
11-124 3-F-Ph 4-Pyr COO-i-Pr
11-125 3-F-Ph 4-Pyr COOBu
11-126 3-F-Ph 4-Pyr COOBn
11-127 3-F-Ph 4-Pyr COOPh
11-128 3-F-Ph 4-Pyr CONH₂              
11-129 3-F-Ph 4-Pyr CONHMe
11-130 3-F-Ph 4-Pyr CONHEt
11-131 3-F-Ph 4-Pyr CONHPr
11-132 3-F-Ph 4-Pyr CONH-i-Pr
11-133 3-F-Ph 4-Pyr CONHBu
11-134 3-F-Ph 4-Pyr CONHBn
11-135 3-F-Ph 4-Pyr CONMe₂             
11-136 3-F-Ph 4-Pyr CONH-c-Pr
11-137 3-F-Ph 4-Pyr CONH-c-Bu
11-138 3-F-Ph 4-Pyr CONH-c-Pen
11-139 3-F-Ph 4-Pyr CONH-c-Hex
11-140 3-F-Ph 4-Pyr CONH-c-Hep
11-141 3-F-Ph 4-Pyr CONHCH₂-c-Pr
11-142 3-F-Ph 4-Pyr CONH-Allyl
11-143 3-F-Ph 4-Pyr CONH-Propargyl
11-144 3-F-Ph 4-Pyr CONHPh
11-145 3-F-Ph 4-Pyr CONH-3-Pyr
11-146 3-F-Ph 4-Pyr CONHCH₂-4-Pyr
11-147 3-F-Ph 4-Pyr CONH- (CH₂)₂-OH
11-148 3-F-Ph 4-Pyr CONHCH (CH₂OH)₂       
11-149 3-F-Ph 4-Pyr CONH- (CH₂)₂-OAc
11-150 3-F-Ph 4-Pyr CONHCH₂CN
11-151 3-F-Ph 4-Pyr CONH- (CH₂)₂-F
11-152 3-F-Ph 4-Pyr CONH- (CH₂)₂-OMe
11-153 3-F-Ph 4-Pyr CONH- (CH₂)₂-SMe
11-154 3-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
11-155 3-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe
11-156 3-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
11-157 3-F-Ph 4-Pyr CONHCH₂COOH
11-158 3-F-Ph 4-Pyr CONHCH₂COOEt
11-159 3-F-Ph 4-Pyr CONHCH (Me) COOEt
11-160 3-F-Ph 4-Pyr CONHCH₂CONH₂         
11-161 3-F-Ph 4-Pyr CONHOH
11-162 3-F-Ph 4-Pyr CONHOMe
11-163 3-F-Ph 4-Pyr CONHOEt
11-164 3-F-Ph 4-Pyr CONHOPr
11-165 3-F-Ph 4-Pyr CONHOAllyl
11-166 3-F-Ph 4-Pyr CONHOBn
11-167 3-F-Ph 4-Pyr CONHNH₂            
11-168 3-F-Ph 4-Pyr CONHNHMe
11-169 3-F-Ph 4-Pyr CONHN (Me)₂          
11-170 3-F-Ph 4-Pyr COMe
11-171 3-F-Ph 4-Pyr COEt
11-172 3-F-Ph 4-Pyr COPr
11-173 3-F-Ph 4-Pyr CO-i-Pr
11-174 3-F-Ph 4-Pyr COBu
11-175 3-F-Ph 4-Pyr COCF_Three              
11-176 3-F-Ph 4-Pyr CO- (CH₂)₂-F          
11-177 3-F-Ph 4-Pyr CO- (CH₂)₂-OH         
11-178 3-F-Ph 4-Pyr CO- (CH₂)₂-OMe        
11-179 3-F-Ph 4-Pyr SOMe
11-180 3-F-Ph 4-Pyr SOEt
11-181 3-F-Ph 4-Pyr SOPr
11-182 3-F-Ph 4-Pyr SO-i-Pr
11-183 3-F-Ph 4-Pyr SOBu
11-184 3-F-Ph 4-Pyr SOCF_Three              
11-185 3-F-Ph 4-Pyr SO- (CH₂)₂-F          
11-186 3-F-Ph 4-Pyr SO- (CH₂)₂-OH         
11-187 3-F-Ph 4-Pyr SO- (CH₂)₂-OMe        
11-188 3-F-Ph 4-Pyr SO₂Me
11-189 3-F-Ph 4-Pyr SO₂Et
11-190 3-F-Ph 4-Pyr SO₂Pr
11-191 3-F-Ph 4-Pyr SO₂-i-Pr
11-192 3-F-Ph 4-Pyr SO₂Bu
11-193 3-F-Ph 4-Pyr SO₂CF_Three              
11-194 3-F-Ph 4-Pyr SO₂-(CH₂)₂-F
11-195 3-F-Ph 4-Pyr SO₂-(CH₂)₂-OH
11-196 3-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe
11-197 3-F-Ph 4-Pyr SO₂NH₂              
11-198 3-F-Ph 4-Pyr SO₂NHMe
11-199 3-F-Ph 4-Pyr SO₂NHEt
11-200 3-F-Ph 4-Pyr SO₂NHPr
11-201 3-F-Ph 4-Pyr SO₂NH-i-Pr
11-202 3-F-Ph 4-Pyr SO₂NHBu
11-203 3-F-Ph 4-Pyr SO₂NHBn
11-204 3-F-Ph 4-Pyr SO₂NMe₂            
11-205 3-F-Ph 4-Pyr SO₂NH-c-Pr
11-206 3-F-Ph 4-Pyr SO₂NH-c-Bu
11-207 3-F-Ph 4-Pyr SO₂NH-c-Pen
11-208 3-F-Ph 4-Pyr SO₂NH-c-Hex
11-209 3-F-Ph 4-Pyr SO₂NH-c-Hep
11-210 3-F-Ph 4-Pyr SO₂NHCH₂-c-Pr
11-211 3-F-Ph 4-Pyr SO₂NH-Allyl
11-212 3-F-Ph 4-Pyr SO₂NH-Propargyl
11-213 3-F-Ph 4-Pyr SO₂NHPh
11-214 3-F-Ph 4-Pyr SO₂NH-3-Pyr
11-215 3-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr
11-216 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
11-217 3-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
11-218 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
11-219 3-F-Ph 4-Pyr SO₂NHCH₂CN           
11-220 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F
11-221 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
11-222 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
11-223 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
11-224 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe    
11-225 3-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
11-226 3-F-Ph 4-Pyr SO₂NHCH₂COOH
11-227 3-F-Ph 4-Pyr SO₂NHCH₂COOEt
11-228 3-F-Ph 4-Pyr SO₂NHCH (Me) COOEt
11-229 3-F-Ph 4-Pyr SO₂NHCH₂CONH₂        
11-230 3-F-Ph 4-Pyr SO₂NHOH
11-231 3-F-Ph 4-Pyr SO₂NHOMe
11-232 3-F-Ph 4-Pyr SO₂NHOEt
11-233 3-F-Ph 4-Pyr SO₂NHOPr
11-234 3-F-Ph 4-Pyr SO₂NHOAllyl
11-235 3-F-Ph 4-Pyr SO₂NHOBn
11-236 3-F-Ph 4-Pyr SO₂NHNH₂            
11-237 3-F-Ph 4-Pyr SO₂NHNHMe
11-238 3-F-Ph 4-Pyr SO₂NHN (Me)₂         
11-239 3-Cl-Ph 4-Pyr COOH
11-240 3-Cl-Ph 4-Pyr COOMe
11-241 3-Cl-Ph 4-Pyr COOEt
11-242 3-Cl-Ph 4-Pyr COOPr
11-243 3-Cl-Ph 4-Pyr COO-i-Pr
11-244 3-Cl-Ph 4-Pyr COOBu
11-245 3-Cl-Ph 4-Pyr COOBn
11-246 3-Cl-Ph 4-Pyr COOPh
11-247 3-Cl-Ph 4-Pyr CONH₂              
11-248 3-Cl-Ph 4-Pyr CONHMe
11-249 3-Cl-Ph 4-Pyr CONHEt
11-250 3-Cl-Ph 4-Pyr CONHPr
11-251 3-Cl-Ph 4-Pyr CONH-i-Pr
11-252 3-Cl-Ph 4-Pyr CONHBu
11-253 3-Cl-Ph 4-Pyr CONHBn
11-254 3-Cl-Ph 4-Pyr CONMe₂             
11-255 3-Cl-Ph 4-Pyr CONH-c-Pr
11-256 3-Cl-Ph 4-Pyr CONH-c-Bu
11-257 3-Cl-Ph 4-Pyr CONH-c-Pen
11-258 3-Cl-Ph 4-Pyr CONH-c-Hex
11-259 3-Cl-Ph 4-Pyr CONH-c-Hep
11-260 3-Cl-Ph 4-Pyr CONHCH₂-c-Pr
11-261 3-Cl-Ph 4-Pyr CONH-Allyl
11-262 3-Cl-Ph 4-Pyr CONH-Propargyl
11-263 3-Cl-Ph 4-Pyr CONHPh
11-264 3-Cl-Ph 4-Pyr CONH-3-Pyr
11-265 3-Cl-Ph 4-Pyr CONHCH₂-4-Pyr
11-266 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OH
11-267 3-Cl-Ph 4-Pyr CONHCH (CH₂OH)₂       
11-268 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OAc
11-269 3-Cl-Ph 4-Pyr CONHCH₂CN
11-270 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-F
11-271 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-OMe
11-272 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-SMe
11-273 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
11-274 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-NHMe
11-275 3-Cl-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
11-276 3-Cl-Ph 4-Pyr CONHCH₂COOH
11-277 3-Cl-Ph 4-Pyr CONHCH₂COOEt
11-278 3-Cl-Ph 4-Pyr CONHCH (Me) COOEt
11-279 3-Cl-Ph 4-Pyr CONHCH₂CONH₂        
11-280 3-Cl-Ph 4-Pyr CONHOH
11-281 3-Cl-Ph 4-Pyr CONHOMe
11-282 3-Cl-Ph 4-Pyr CONHOEt
11-283 3-Cl-Ph 4-Pyr CONHOPr
11-284 3-Cl-Ph 4-Pyr CONHOAllyl
11-285 3-Cl-Ph 4-Pyr CONHOBn
11-286 3-Cl-Ph 4-Pyr CONHNH₂            
11-287 3-Cl-Ph 4-Pyr CONHNHMe
11-288 3-Cl-Ph 4-Pyr CONHN (Me)₂          
11-289 3-Cl-Ph 4-Pyr COMe
11-290 3-Cl-Ph 4-Pyr COEt
11-291 3-Cl-Ph 4-Pyr COPr
11-292 3-Cl-Ph 4-Pyr CO-i-Pr
11-293 3-Cl-Ph 4-Pyr COBu
11-294 3-Cl-Ph 4-Pyr COCF_Three               
11-295 3-Cl-Ph 4-Pyr CO- (CH₂)₂-F
11-296 3-Cl-Ph 4-Pyr CO- (CH₂)₂-OH
11-297 3-Cl-Ph 4-Pyr CO- (CH₂)₂-OMe
11-298 3-Cl-Ph 4-Pyr SOMe
11-299 3-Cl-Ph 4-Pyr SOEt
11-300 3-Cl-Ph 4-Pyr SOPr
11-301 3-Cl-Ph 4-Pyr SO-i-Pr
11-302 3-Cl-Ph 4-Pyr SOBu
11-303 3-Cl-Ph 4-Pyr SOCF_Three               
11-304 3-Cl-Ph 4-Pyr SO- (CH₂)₂-F          
11-305 3-Cl-Ph 4-Pyr SO- (CH₂)₂-OH         
11-306 3-Cl-Ph 4-Pyr SO- (CH₂)₂-OMe        
11-307 3-Cl-Ph 4-Pyr SO₂Me
11-308 3-Cl-Ph 4-Pyr SO₂Et
11-309 3-Cl-Ph 4-Pyr SO₂Pr
11-310 3-Cl-Ph 4-Pyr SO₂-i-Pr
11-311 3-Cl-Ph 4-Pyr SO₂Bu
11-312 3-Cl-Ph 4-Pyr SO₂CF_Three              
11-313 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-F
11-314 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-OH
11-315 3-Cl-Ph 4-Pyr SO₂-(CH₂)₂-OMe
11-316 3-Cl-Ph 4-Pyr SO₂NH₂              
11-317 3-Cl-Ph 4-Pyr SO₂NHMe
11-318 3-Cl-Ph 4-Pyr SO₂NHEt
11-319 3-Cl-Ph 4-Pyr SO₂NHPr
11-320 3-Cl-Ph 4-Pyr SO₂NH-i-Pr
11-321 3-Cl-Ph 4-Pyr SO₂NHBu
11-322 3-Cl-Ph 4-Pyr SO₂NHBn
11-323 3-Cl-Ph 4-Pyr SO₂NMe₂             
11-324 3-Cl-Ph 4-Pyr SO₂NH-c-Pr
11-325 3-Cl-Ph 4-Pyr SO₂NH-c-Bu
11-326 3-Cl-Ph 4-Pyr SO₂NH-c-Pen
11-327 3-Cl-Ph 4-Pyr SO₂NH-c-Hex
11-328 3-Cl-Ph 4-Pyr SO₂NH-c-Hep
11-329 3-Cl-Ph 4-Pyr SO₂NHCH₂-c-Pr
11-330 3-Cl-Ph 4-Pyr SO₂NH-Allyl
11-331 3-Cl-Ph 4-Pyr SO₂NH-Propargyl
11-332 3-Cl-Ph 4-Pyr SO₂NHPh
11-333 3-Cl-Ph 4-Pyr SO₂NH-3-Pyr
11-334 3-Cl-Ph 4-Pyr SO₂NHCH₂-4-Pyr
11-335 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
11-336 3-Cl-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
11-337 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
11-338 3-Cl-Ph 4-Pyr SO₂NHCH₂CN           
11-339 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-F
11-340 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
11-341 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
11-342 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
11-343 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
11-344 3-Cl-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂ 
11-345 3-Cl-Ph 4-Pyr SO₂NHCH₂COOH
11-346 3-Cl-Ph 4-Pyr SO₂NHCH₂COOEt
11-347 3-Cl-Ph 4-Pyr SO₂NHCH (Me) COOEt
11-348 3-Cl-Ph 4-Pyr SO₂NHCH₂CONH₂        
11-349 3-Cl-Ph 4-Pyr SO₂NHOH
11-350 3-Cl-Ph 4-Pyr SO₂NHOMe
11-351 3-Cl-Ph 4-Pyr SO₂NHOEt
11-352 3-Cl-Ph 4-Pyr SO₂NHOPr
11-353 3-Cl-Ph 4-Pyr SO₂NHOAllyl
11-354 3-Cl-Ph 4-Pyr SO₂NHOBn
11-355 3-Cl-Ph 4-Pyr SO₂NHNH₂            
11-356 3-Cl-Ph 4-Pyr SO₂NHNHMe
11-357 3-Cl-Ph 4-Pyr SO₂NHN (Me)₂         
11-358 4-F-Ph 4-Pyr COOH
11-359 4-F-Ph 4-Pyr COOMe
11-360 4-F-Ph 4-Pyr COOEt
11-361 4-F-Ph 4-Pyr COOPr
11-362 4-F-Ph 4-Pyr COO-i-Pr
11-363 4-F-Ph 4-Pyr COOBu
11-364 4-F-Ph 4-Pyr COOBn
11-365 4-F-Ph 4-Pyr COOPh
11-366 4-F-Ph 4-Pyr CONH₂               
11-367 4-F-Ph 4-Pyr CONHMe
11-368 4-F-Ph 4-Pyr CONHEt
11-369 4-F-Ph 4-Pyr CONHPr
11-370 4-F-Ph 4-Pyr CONH-i-Pr
11-371 4-F-Ph 4-Pyr CONHBu
11-372 4-F-Ph 4-Pyr CONHBn
11-373 4-F-Ph 4-Pyr CONMe₂              
11-374 4-F-Ph 4-Pyr CONH-c-Pr
11-375 4-F-Ph 4-Pyr CONH-c-Bu
11-376 4-F-Ph 4-Pyr CONH-c-Pen
11-377 4-F-Ph 4-Pyr CONH-c-Hex
11-378 4-F-Ph 4-Pyr CONH-c-Hep
11-379 4-F-Ph 4-Pyr CONHCH₂-c-Pr         
11-380 4-F-Ph 4-Pyr CONH-Allyl
11-381 4-F-Ph 4-Pyr CONH-Propargyl
11-382 4-F-Ph 4-Pyr CONHPh
11-383 4-F-Ph 4-Pyr CONH-3-Pyr
11-384 4-F-Ph 4-Pyr CONHCH₂-4-Pyr        
11-385 4-F-Ph 4-Pyr CONH- (CH₂)₂-OH       
11-386 4-F-Ph 4-Pyr CONHCH (CH₂OH)₂      
11-387 4-F-Ph 4-Pyr CONH- (CH₂)₂-OAc      
11-388 4-F-Ph 4-Pyr CONHCH₂CN
11-389 4-F-Ph 4-Pyr CONH- (CH₂)₂-F        
11-390 4-F-Ph 4-Pyr CONH- (CH₂)₂-OMe      
11-391 4-F-Ph 4-Pyr CONH- (CH₂)₂-SMe      
11-392 4-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
11-393 4-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe     
11-394 4-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
11-395 4-F-Ph 4-Pyr CONHCH₂COOH
11-396 4-F-Ph 4-Pyr CONHCH₂COOEt
11-397 4-F-Ph 4-Pyr CONHCH (Me) COOEt
11-398 4-F-Ph 4-Pyr CONHCH₂CONH₂        
11-399 4-F-Ph 4-Pyr CONHOH
11-400 4-F-Ph 4-Pyr CONHOMe
11-401 4-F-Ph 4-Pyr CONHOEt
11-402 4-F-Ph 4-Pyr CONHOPr
11-403 4-F-Ph 4-Pyr CONHOAllyl
11-404 4-F-Ph 4-Pyr CONHOBn
11-405 4-F-Ph 4-Pyr CONHNH₂             
11-406 4-F-Ph 4-Pyr CONHNHMe
11-407 4-F-Ph 4-Pyr CONHN (Me)₂          
11-408 4-F-Ph 4-Pyr COMe
11-409 4-F-Ph 4-Pyr COEt
11-410 4-F-Ph 4-Pyr COPr
11-411 4-F-Ph 4-Pyr CO-i-Pr
11-412 4-F-Ph 4-Pyr COBu
11-413 4-F-Ph 4-Pyr COCF_Three               
11-414 4-F-Ph 4-Pyr CO- (CH₂)₂-F         
11-415 4-F-Ph 4-Pyr CO- (CH₂)₂-OH
11-416 4-F-Ph 4-Pyr CO- (CH₂)₂-OMe
11-417 4-F-Ph 4-Pyr SOMe
11-418 4-F-Ph 4-Pyr SOEt
11-419 4-F-Ph 4-Pyr SOPr
11-420 4-F-Ph 4-Pyr SO-i-Pr
11-421 4-F-Ph 4-Pyr SOBu
11-422 4-F-Ph 4-Pyr SOCF_Three               
11-423 4-F-Ph 4-Pyr SO- (CH₂)₂-F
11-424 4-F-Ph 4-Pyr SO- (CH₂)₂-OH
11-425 4-F-Ph 4-Pyr SO- (CH₂)₂-OMe
11-426 4-F-Ph 4-Pyr SO₂Me
11-427 4-F-Ph 4-Pyr SO₂Et
11-428 4-F-Ph 4-Pyr SO₂Pr
11-429 4-F-Ph 4-Pyr SO₂-i-Pr
11-430 4-F-Ph 4-Pyr SO₂Bu
11-431 4-F-Ph 4-Pyr SO₂CF_Three              
11-432 4-F-Ph 4-Pyr SO₂-(CH₂)₂-F
11-433 4-F-Ph 4-Pyr SO₂-(CH₂)₂-OH
11-434 4-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe
11-435 4-F-Ph 4-Pyr SO₂NH₂              
11-436 4-F-Ph 4-Pyr SO₂NHMe
11-437 4-F-Ph 4-Pyr SO₂NHEt
11-438 4-F-Ph 4-Pyr SO₂NHPr
11-439 4-F-Ph 4-Pyr SO₂NH-i-Pr
11-440 4-F-Ph 4-Pyr SO₂NHBu
11-441 4-F-Ph 4-Pyr SO₂NHBn
11-442 4-F-Ph 4-Pyr SO₂NMe₂             
11-443 4-F-Ph 4-Pyr SO₂NH-c-Pr
11-444 4-F-Ph 4-Pyr SO₂NH-c-Bu
11-445 4-F-Ph 4-Pyr SO₂NH-c-Pen
11-446 4-F-Ph 4-Pyr SO₂NH-c-Hex
11-447 4-F-Ph 4-Pyr SO₂NH-c-Hep
11-448 4-F-Ph 4-Pyr SO₂NHCH₂-c-Pr        
11-449 4-F-Ph 4-Pyr SO₂NH-Allyl
11-450 4-F-Ph 4-Pyr SO₂NH-Propargyl
11-451 4-F-Ph 4-Pyr SO₂NHPh
11-452 4-F-Ph 4-Pyr SO₂NH-3-Pyr
11-453 4-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr
11-454 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH      
11-455 4-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂     
11-456 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc     
11-457 4-F-Ph 4-Pyr SO₂NHCH₂CN
11-458 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F
11-459 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
11-460 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
11-461 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
11-462 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
11-463 4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
11-464 4-F-Ph 4-Pyr SO₂NHCH₂COOH
11-465 4-F-Ph 4-Pyr SO₂NHCH₂COOEt        
11-466 4-F-Ph 4-Pyr SO₂NHCH (Me) COOEt
11-467 4-F-Ph 4-Pyr SO₂NHCH₂CONH₂        
11-468 4-F-Ph 4-Pyr SO₂NHOH
11-469 4-F-Ph 4-Pyr SO₂NHOMe
11-470 4-F-Ph 4-Pyr SO₂NHOEt
11-471 4-F-Ph 4-Pyr SO₂NHOPr
11-472 4-F-Ph 4-Pyr SO₂NHOAllyl
11-473 4-F-Ph 4-Pyr SO₂NHOBn
11-474 4-F-Ph 4-Pyr SO₂NHNH₂            
11-475 4-F-Ph 4-Pyr SO₂NHNHMe
11-476 4-F-Ph 4-Pyr SO₂NHN (Me)₂         
11-477 3-Cl-4-F-Ph 4-Pyr COOH
11-478 3-Cl-4-F-Ph 4-Pyr COOMe
11-479 3-Cl-4-F-Ph 4-Pyr COOEt
11-480 3-Cl-4-F-Ph 4-Pyr COOPr
11-481 3-Cl-4-F-Ph 4-Pyr COO-i-Pr
11-482 3-Cl-4-F-Ph 4-Pyr COOBu
11-483 3-Cl-4-F-Ph 4-Pyr COOBn
11-484 3-Cl-4-F-Ph 4-Pyr COOPh
11-485 3-Cl-4-F-Ph 4-Pyr CONH₂              
11-486 3-Cl-4-F-Ph 4-Pyr CONHMe
11-487 3-Cl-4-F-Ph 4-Pyr CONHEt
11-488 3-Cl-4-F-Ph 4-Pyr CONHPr
11-489 3-Cl-4-F-Ph 4-Pyr CONH-i-Pr
11-490 3-Cl-4-F-Ph 4-Pyr CONHBu
11-491 3-Cl-4-F-Ph 4-Pyr CONHBn
11-492 3-Cl-4-F-Ph 4-Pyr CONMe₂             
11-493 3-Cl-4-F-Ph 4-Pyr CONH-c-Pr
11-494 3-Cl-4-F-Ph 4-Pyr CONH-c-Bu
11-495 3-Cl-4-F-Ph 4-Pyr CONH-c-Pen
11-496 3-Cl-4-F-Ph 4-Pyr CONH-c-Hex
11-497 3-Cl-4-F-Ph 4-Pyr CONH-c-Hep
11-498 3-Cl-4-F-Ph 4-Pyr CONHCH₂-c-Pr
11-499 3-Cl-4-F-Ph 4-Pyr CONH-Allyl
11-500 3-Cl-4-F-Ph 4-Pyr CONH-Propargyl
11-501 3-Cl-4-F-Ph 4-Pyr CONHPh
11-502 3-Cl-4-F-Ph 4-Pyr CONH-3-Pyr
11-503 3-Cl-4-F-Ph 4-Pyr CONHCH₂-4-Pyr
11-504 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OH       
11-505 3-Cl-4-F-Ph 4-Pyr CONHCH (CH₂OH)₂      
11-506 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OAc      
11-507 3-Cl-4-F-Ph 4-Pyr CONHCH₂CN
11-508 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-F        
11-509 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-OMe      
11-510 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-SMe
11-511 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
11-512 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-NHMe     
11-513 3-Cl-4-F-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
11-514 3-Cl-4-F-Ph 4-Pyr CONHCH₂COOH
11-515 3-Cl-4-F-Ph 4-Pyr CONHCH₂COOEt
11-516 3-Cl-4-F-Ph 4-Pyr CONHCH (Me) COOEt
11-517 3-Cl-4-F-Ph 4-Pyr CONHCH₂CONH₂        
11-518 3-Cl-4-F-Ph 4-Pyr CONHOH
11-519 3-Cl-4-F-Ph 4-Pyr CONHOMe
11-520 3-Cl-4-F-Ph 4-Pyr CONHOEt
11-521 3-Cl-4-F-Ph 4-Pyr CONHOPr
11-522 3-Cl-4-F-Ph 4-Pyr CONHOAllyl
11-523 3-Cl-4-F-Ph 4-Pyr CONHOBn
11-524 3-Cl-4-F-Ph 4-Pyr CONHNH₂             
11-525 3-Cl-4-F-Ph 4-Pyr CONHNHMe
11-526 3-Cl-4-F-Ph 4-Pyr CONHN (Me)₂          
11-527 3-Cl-4-F-Ph 4-Pyr COMe
11-528 3-Cl-4-F-Ph 4-Pyr COEt
11-529 3-Cl-4-F-Ph 4-Pyr COPr
11-530 3-Cl-4-F-Ph 4-Pyr CO-i-Pr
11-531 3-Cl-4-F-Ph 4-Pyr COBu
11-532 3-Cl-4-F-Ph 4-Pyr COCF_Three              
11-533 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-F          
11-534 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-OH         
11-535 3-Cl-4-F-Ph 4-Pyr CO- (CH₂)₂-OMe        
11-536 3-Cl-4-F-Ph 4-Pyr SOMe
11-537 3-Cl-4-F-Ph 4-Pyr SOEt
11-538 3-Cl-4-F-Ph 4-Pyr SOPr
11-539 3-Cl-4-F-Ph 4-Pyr SO-i-Pr
11-540 3-Cl-4-F-Ph 4-Pyr SOBu
11-541 3-Cl-4-F-Ph 4-Pyr SOCF_Three              
11-542 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-F
11-543 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-OH
11-544 3-Cl-4-F-Ph 4-Pyr SO- (CH₂)₂-OMe
11-545 3-Cl-4-F-Ph 4-Pyr SO₂Me
11-546 3-Cl-4-F-Ph 4-Pyr SO₂Et
11-547 3-Cl-4-F-Ph 4-Pyr SO₂Pr
11-548 3-Cl-4-F-Ph 4-Pyr SO₂-i-Pr
11-549 3-Cl-4-F-Ph 4-Pyr SO₂Bu
11-550 3-Cl-4-F-Ph 4-Pyr SO₂CF_Three              
11-551 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-F         
11-552 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-OH        
11-553 3-Cl-4-F-Ph 4-Pyr SO₂-(CH₂)₂-OMe       
11-554 3-Cl-4-F-Ph 4-Pyr SO₂NH₂              
11-555 3-Cl-4-F-Ph 4-Pyr SO₂NHMe              
11-556 3-Cl-4-F-Ph 4-Pyr SO₂NHEt
11-557 3-Cl-4-F-Ph 4-Pyr SO₂NHPr
11-558 3-Cl-4-F-Ph 4-Pyr SO₂NH-i-Pr
11-559 3-Cl-4-F-Ph 4-Pyr SO₂NHBu
11-560 3-Cl-4-F-Ph 4-Pyr SO₂NHBn
11-561 3-Cl-4-F-Ph 4-Pyr SO₂NMe₂             
11-562 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Pr
11-563 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Bu
11-564 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Pen
11-565 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Hex
11-566 3-Cl-4-F-Ph 4-Pyr SO₂NH-c-Hep
11-567 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂-c-Pr
11-568 3-Cl-4-F-Ph 4-Pyr SO₂NH-Allyl
11-569 3-Cl-4-F-Ph 4-Pyr SO₂NH-Propargyl
11-570 3-Cl-4-F-Ph 4-Pyr SO₂NHPh
11-571 3-Cl-4-F-Ph 4-Pyr SO₂NH-3-Pyr
11-572 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂-4-Pyr
11-573 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
11-574 3-Cl-4-F-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
11-575 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
11-576 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂CN           
11-577 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-F
11-578 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
11-579 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
11-580 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
11-581 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
11-582 3-Cl-4-F-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
11-583 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂COOH
11-584 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂COOEt
11-585 3-Cl-4-F-Ph 4-Pyr SO₂NHCH (Me) COOEt
11-586 3-Cl-4-F-Ph 4-Pyr SO₂NHCH₂CONH₂        
11-587 3-Cl-4-F-Ph 4-Pyr SO₂NHOH
11-588 3-Cl-4-F-Ph 4-Pyr SO₂NHOMe
11-589 3-Cl-4-F-Ph 4-Pyr SO₂NHOEt
11-590 3-Cl-4-F-Ph 4-Pyr SO₂NHOPr
11-591 3-Cl-4-F-Ph 4-Pyr SO₂NHOAllyl
11-592 3-Cl-4-F-Ph 4-Pyr SO₂NHOBn
11-593 3-Cl-4-F-Ph 4-Pyr SO₂NHNH₂            
11-594 3-Cl-4-F-Ph 4-Pyr SO₂NHNHMe
11-595 3-Cl-4-F-Ph 4-Pyr SO₂NHN (Me)₂         
11-596 3,4-F₂-Ph 4-Pyr COOH
11-597 3,4-F₂-Ph 4-Pyr COOMe
11-598 3,4-F₂-Ph 4-Pyr COOEt
11-599 3,4-F₂-Ph 4-Pyr COOPr
11-600 3,4-F₂-Ph 4-Pyr COO-i-Pr
11-601 3,4-F₂-Ph 4-Pyr COOBu
11-602 3,4-F₂-Ph 4-Pyr COOBn
11-603 3,4-F₂-Ph 4-Pyr COOPh
11-604 3,4-F₂-Ph 4-Pyr CONH₂              
11-605 3,4-F₂-Ph 4-Pyr CONHMe
11-606 3,4-F₂-Ph 4-Pyr CONHEt
11-607 3,4-F₂-Ph 4-Pyr CONHPr
11-608 3,4-F₂-Ph 4-Pyr CONH-i-Pr
11-609 3,4-F₂-Ph 4-Pyr CONHBu
11-610 3,4-F₂-Ph 4-Pyr CONHBn
11-611 3,4-F₂-Ph 4-Pyr CONMe₂             
11-612 3,4-F₂-Ph 4-Pyr CONH-c-Pr
11-613 3,4-F₂-Ph 4-Pyr CONH-c-Bu
11-614 3,4-F₂-Ph 4-Pyr CONH-c-Pen
11-615 3,4-F₂-Ph 4-Pyr CONH-c-Hex
11-616 3,4-F₂-Ph 4-Pyr CONH-c-Hep
11-617 3,4-F₂-Ph 4-Pyr CONHCH₂-c-Pr
11-618 3,4-F₂-Ph 4-Pyr CONH-Allyl
11-619 3,4-F₂-Ph 4-Pyr CONH-Propargyl
11-620 3,4-F₂-Ph 4-Pyr CONHPh
11-621 3,4-F₂-Ph 4-Pyr CONH-3-Pyr
11-622 3,4-F₂-Ph 4-Pyr CONHCH₂-4-Pyr
11-623 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-OH
11-624 3,4-F₂-Ph 4-Pyr CONHCH (CH₂OH)₂      
11-625 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-OAc
11-626 3,4-F₂-Ph 4-Pyr CONHCH₂CN
11-627 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-F
11-628 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-OMe
11-629 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-SMe
11-630 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
11-631 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-NHMe
11-632 3,4-F₂-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
11-633 3,4-F₂-Ph 4-Pyr CONHCH₂COOH
11-634 3,4-F₂-Ph 4-Pyr CONHCH₂COOEt
11-635 3,4-F₂-Ph 4-Pyr CONHCH (Me) COOEt
11-636 3,4-F₂-Ph 4-Pyr CONHCH₂CONH₂        
11-637 3,4-F₂-Ph 4-Pyr CONHOH
11-638 3,4-F₂-Ph 4-Pyr CONHOMe
11-639 3,4-F₂-Ph        4-Pyr CONHOEt
11-640 3,4-F₂-Ph 4-Pyr CONHOPr
11-641 3,4-F₂-Ph 4-Pyr CONHOAllyl
11-642 3,4-F₂-Ph 4-Pyr CONHOBn
11-643 3,4-F₂-Ph 4-Pyr CONHNH₂            
11-644 3,4-F₂-Ph 4-Pyr CONHNHMe
11-645 3,4-F₂-Ph 4-Pyr CONHN (Me)₂          
11-646 3,4-F₂-Ph 4-Pyr COMe
11-647 3,4-F₂-Ph 4-Pyr COEt
11-648 3,4-F₂-Ph 4-Pyr COPr
11-649 3,4-F₂-Ph 4-Pyr CO-i-Pr
11-650 3,4-F₂-Ph 4-Pyr COBu
11-651 3,4-F₂-Ph 4-Pyr COCF_Three              
11-652 3,4-F₂-Ph 4-Pyr CO- (CH₂)₂-F          
11-653 3,4-F₂-Ph 4-Pyr CO- (CH₂)₂-OH         
11-654 3,4-F₂-Ph 4-Pyr CO- (CH₂)₂-OMe        
11-655 3,4-F₂-Ph 4-Pyr SOMe
11-656 3,4-F₂-Ph 4-Pyr SOEt
11-657 3,4-F₂-Ph 4-Pyr SOPr
11-658 3,4-F₂-Ph 4-Pyr SO-i-Pr
11-659 3,4-F₂-Ph 4-Pyr SOBu
11-660 3,4-F₂-Ph 4-Pyr SOCF_Three              
11-661 3,4-F₂-Ph 4-Pyr SO- (CH₂)₂-F         
11-662 3,4-F₂-Ph 4-Pyr SO- (CH₂)₂-OH        
11-663 3,4-F₂-Ph 4-Pyr SO- (CH₂)₂-OMe       
11-664 3,4-F₂-Ph 4-Pyr SO₂Me
11-665 3,4-F₂-Ph 4-Pyr SO₂Et
11-666 3,4-F₂-Ph 4-Pyr SO₂Pr
11-667 3,4-F₂-Ph 4-Pyr SO₂-i-Pr
11-668 3,4-F₂-Ph 4-Pyr SO₂Bu
11-669 3,4-F₂-Ph 4-Pyr SO₂CF_Three             
11-670 3,4-F₂-Ph 4-Pyr SO₂-(CH₂)₂-F         
11-671 3,4-F₂-Ph 4-Pyr SO₂-(CH₂)₂-OH        
11-672 3,4-F₂-Ph 4-Pyr SO₂-(CH₂)₂-OMe       
11-673 3,4-F₂-Ph 4-Pyr SO₂NH₂             
11-674 3,4-F₂-Ph 4-Pyr SO₂NHMe
11-675 3,4-F₂-Ph 4-Pyr SO₂NHEt
11-676 3,4-F₂-Ph 4-Pyr SO₂NHPr
11-677 3,4-F₂-Ph 4-Pyr SO₂NH-i-Pr
11-678 3,4-F₂-Ph 4-Pyr SO₂NHBu
11-679 3,4-F₂-Ph 4-Pyr SO₂NHBn
11-680 3,4-F₂-Ph 4-Pyr SO₂NMe₂            
11-681 3,4-F₂-Ph 4-Pyr SO₂NH-c-Pr
11-682 3,4-F₂-Ph 4-Pyr SO₂NH-c-Bu
11-683 3,4-F₂-Ph 4-Pyr SO₂NH-c-Pen
11-684 3,4-F₂-Ph        4-Pyr SO₂NH-c-Hex
11-685 3,4-F₂-Ph 4-Pyr SO₂NH-c-Hep
11-686 3,4-F₂-Ph 4-Pyr SO₂NHCH₂-c-Pr
11-687 3,4-F₂-Ph 4-Pyr SO₂NH-Allyl
11-688 3,4-F₂-Ph 4-Pyr SO₂NH-Propargyl
11-689 3,4-F₂-Ph 4-Pyr SO₂NHPh
11-690 3,4-F₂-Ph 4-Pyr SO₂NH-3-Pyr
11-691 3,4-F₂-Ph 4-Pyr SO₂NHCH₂-4-Pyr
11-692 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
11-693 3,4-F₂-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
11-694 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
11-695 3,4-F₂-Ph 4-Pyr SO₂NHCH₂CN
11-696 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-F
11-697 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
11-698 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
11-699 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
11-700 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
11-701 3,4-F₂-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
11-702 3,4-F₂-Ph 4-Pyr SO₂NHCH₂COOH
11-703 3,4-F₂-Ph 4-Pyr SO₂NHCH₂COOEt
11-704 3,4-F₂-Ph 4-Pyr SO₂NHCH (Me) COOEt
11-705 3,4-F₂-Ph 4-Pyr SO₂NHCH₂CONH₂        
11-706 3,4-F₂-Ph 4-Pyr SO₂NHOH
11-707 3,4-F₂-Ph 4-Pyr SO₂NHOMe
11-708 3,4-F₂-Ph 4-Pyr SO₂NHOEt
11-709 3,4-F₂-Ph 4-Pyr SO₂NHOPr
11-710 3,4-F₂-Ph 4-Pyr SO₂NHOAllyl
11-711 3,4-F₂-Ph 4-Pyr SO₂NHOBn
11-712 3,4-F₂-Ph 4-Pyr SO₂NHNH₂            
11-713 3,4-F₂-Ph 4-Pyr SO₂NHNHMe
11-714 3,4-F₂-Ph 4-Pyr SO₂NHN (Me)₂         
11-715 3-CF_Three-Ph 4-Pyr COOH
11-716 3-CF_Three-Ph 4-Pyr COOMe
11-717 3-CF_Three-Ph 4-Pyr COOEt
11-718 3-CF_Three-Ph 4-Pyr COOPr
11-719 3-CF_Three-Ph 4-Pyr COO-i-Pr
11-720 3-CF_Three-Ph 4-Pyr COOBu
11-721 3-CF_Three-Ph 4-Pyr COOBn
11-722 3-CF_Three-Ph 4-Pyr COOPh
11-723 3-CF_Three-Ph 4-Pyr CONH₂              
11-724 3-CF_Three-Ph 4-Pyr CONHMe
11-725 3-CF_Three-Ph 4-Pyr CONHEt
11-726 3-CF_Three-Ph 4-Pyr CONHPr
11-727 3-CF_Three-Ph 4-Pyr CONH-i-Pr
11-728 3-CF_Three-Ph 4-Pyr CONHBu
11-729 3-CF_Three-Ph 4-Pyr CONHBn
11-730 3-CF_Three-Ph 4-Pyr CONMe₂             
11-731 3-CF_Three-Ph 4-Pyr CONH-c-Pr
11-732 3-CF_Three-Ph 4-Pyr CONH-c-Bu
11-733 3-CF_Three-Ph 4-Pyr CONH-c-Pen
11-734 3-CF_Three-Ph 4-Pyr CONH-c-Hex
11-735 3-CF_Three-Ph 4-Pyr CONH-c-Hep
11-736 3-CF_Three-Ph 4-Pyr CONHCH₂-c-Pr
11-737 3-CF_Three-Ph 4-Pyr CONH-Allyl
11-738 3-CF_Three-Ph 4-Pyr CONH-Propargyl
11-739 3-CF_Three-Ph 4-Pyr CONHPh
11-740 3-CF_Three-Ph 4-Pyr CONH-3-Pyr
11-741 3-CF_Three-Ph 4-Pyr CONHCH₂-4-Pyr
11-742 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-OH
11-743 3-CF_Three-Ph 4-Pyr CONHCH (CH₂OH)₂      
11-744 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-OAc
11-745 3-CF_Three-Ph 4-Pyr CONHCH₂CN
11-746 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-F
11-747 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-OMe
11-748 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-SMe
11-749 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-NH₂      
11-750 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-NHMe
11-751 3-CF_Three-Ph 4-Pyr CONH- (CH₂)₂-N (Me)₂   
11-752 3-CF_Three-Ph 4-Pyr CONHCH₂COOH
11-753 3-CF_Three-Ph 4-Pyr CONHCH₂COOEt
11-754 3-CF_Three-Ph 4-Pyr CONHCH (Me) COOEt
11-755 3-CF_Three-Ph 4-Pyr CONHCH₂CONH₂        
11-756 3-CF_Three-Ph 4-Pyr CONHOH
11-757 3-CF_Three-Ph         4-Pyr CONHOMe
11-758 3-CF_Three-Ph 4-Pyr CONHOEt
11-759 3-CF_Three-Ph 4-Pyr CONHOPr
11-760 3-CF_Three-Ph 4-Pyr CONHOAllyl
11-761 3-CF_Three-Ph 4-Pyr CONHOBn
11-762 3-CF_Three-Ph 4-Pyr CONHNH₂            
11-763 3-CF_Three-Ph 4-Pyr CONHNHMe
11-764 3-CF_Three-Ph 4-Pyr CONHN (Me)₂          
11-765 3-CF_Three-Ph 4-Pyr COMe
11-766 3-CF_Three-Ph 4-Pyr COEt
11-767 3-CF_Three-Ph 4-Pyr COPr
11-768 3-CF_Three-Ph 4-Pyr CO-i-Pr
11-769 3-CF_Three-Ph 4-Pyr COBu
11-770 3-CF_Three-Ph 4-Pyr COCF_Three              
11-771 3-CF_Three-Ph 4-Pyr CO- (CH₂)₂-F          
11-772 3-CF_Three-Ph 4-Pyr CO- (CH₂)₂-OH         
11-773 3-CF_Three-Ph 4-Pyr CO- (CH₂)₂-OMe        
11-774 3-CF_Three-Ph 4-Pyr SOMe
11-775 3-CF_Three-Ph 4-Pyr SOEt
11-776 3-CF_Three-Ph 4-Pyr SOPr
11-777 3-CF_Three-Ph 4-Pyr SO-i-Pr
11-778 3-CF_Three-Ph 4-Pyr SOBu
11-779 3-CF_Three-Ph 4-Pyr SOCF_Three              
11-780 3-CF_Three-Ph 4-Pyr SO- (CH₂)₂-F         
11-781 3-CF_Three-Ph 4-Pyr SO- (CH₂)₂-OH        
11-782 3-CF_Three-Ph 4-Pyr SO- (CH₂)₂-OMe       
11-783 3-CF_Three-Ph 4-Pyr SO₂Me
11-784 3-CF_Three-Ph 4-Pyr SO₂Et
11-785 3-CF_Three-Ph 4-Pyr SO₂Pr
11-786 3-CF_Three-Ph 4-Pyr SO₂-i-Pr
11-787 3-CF_Three-Ph 4-Pyr SO₂Bu
11-788 3-CF_Three-Ph 4-Pyr SO₂CF_Three             
11-789 3-CF_Three-Ph 4-Pyr SO₂-(CH₂)₂-F
11-790 3-CF_Three-Ph 4-Pyr SO₂-(CH₂)₂-OH
11-791 3-CF_Three-Ph 4-Pyr SO₂-(CH₂)₂-OMe
11-792 3-CF_Three-Ph 4-Pyr SO₂NH₂             
11-793 3-CF_Three-Ph 4-Pyr SO₂NHMe
11-794 3-CF_Three-Ph 4-Pyr SO₂NHEt
11-795 3-CF_Three-Ph 4-Pyr SO₂NHPr
11-796 3-CF_Three-Ph 4-Pyr SO₂NH-i-Pr
11-797 3-CF_Three-Ph 4-Pyr SO₂NHBu
11-798 3-CF_Three-Ph 4-Pyr SO₂NHBn
11-799 3-CF_Three-Ph 4-Pyr SO₂NMe₂            
11-800 3-CF_Three-Ph 4-Pyr SO₂NH-c-Pr
11-801 3-CF_Three-Ph 4-Pyr SO₂NH-c-Bu
11-802 3-CF_Three-Ph 4-Pyr SO₂NH-c-Pen
11-803 3-CF_Three-Ph 4-Pyr SO₂NH-c-Hex
11-804 3-CF_Three-Ph 4-Pyr SO₂NH-c-Hep
11-805 3-CF_Three-Ph 4-Pyr SO₂NHCH₂-c-Pr
11-806 3-CF_Three-Ph 4-Pyr SO₂NH-Allyl
11-807 3-CF_Three-Ph 4-Pyr SO₂NH-Propargyl
11-808 3-CF_Three-Ph 4-Pyr SO₂NHPh
11-809 3-CF_Three-Ph 4-Pyr SO₂NH-3-Pyr
11-810 3-CF_Three-Ph 4-Pyr SO₂NHCH₂-4-Pyr
11-811 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-OH
11-812 3-CF_Three-Ph 4-Pyr SO₂NHCH (CH₂OH)₂      
11-813 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-OAc
11-814 3-CF_Three-Ph 4-Pyr SO₂NHCH₂CN
11-815 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-F
11-816 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-OMe
11-817 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-SMe
11-818 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-NH₂     
11-819 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-NHMe
11-820 3-CF_Three-Ph 4-Pyr SO₂NH- (CH₂)₂-N (Me)₂  
11-821 3-CF_Three-Ph 4-Pyr SO₂NHCH₂COOH
11-822 3-CF_Three-Ph 4-Pyr SO₂NHCH₂COOEt
11-823 3-CF_Three-Ph 4-Pyr SO₂NHCH (Me) COOEt
11-824 3-CF_Three-Ph 4-Pyr SO₂NHCH₂CONH₂        
11-825 3-CF_Three-Ph 4-Pyr SO₂NHOH
11-826 3-CF_Three-Ph 4-Pyr SO₂NHOMe
11-827 3-CF_Three-Ph 4-Pyr SO₂NHOEt
11-828 3-CF_Three-Ph 4-Pyr SO₂NHOPr
11-829 3-CF_Three-Ph 4-Pyr SO₂NHOAllyl
11-830 3-CF_Three-Ph 4-Pyr SO₂NHOBn
11-831 3-CF_Three-Ph 4-Pyr SO₂NHNH₂            
11-832 3-CF_Three-Ph 4-Pyr SO₂NHNHMe
11-833 3-CF_Three-Ph 4-Pyr SO₂NHN (Me)₂        
11-834 4-F-Ph 4-Pym CONH₂              
11-835 4-F-Ph 4-Pym CONHMe
11-836 4-F-Ph 4-Pym CONHEt
11-837 4-F-Ph 4-Pym CONHPr
11-838 4-F-Ph 4-Pym CONH-i-Pr
11-839 4-F-Ph 4-Pym CONHBu
11-840 4-F-Ph 4-Pym CONHBn
11-841 4-F-Ph 4-Pym CONMe₂              
11-842 4-F-Ph 4-Pym CONH-c-Pr
11-843 4-F-Ph 4-Pym CONH-c-Bu
11-844 4-F-Ph 4-Pym CONH-c-Pen
11-845 4-F-Ph 4-Pym CONH-c-Hex
11-846 4-F-Ph 4-Pym CONH-c-Hep
11-847 4-F-Ph 4-Pym CONHCH₂-c-Pr         
11-848 4-F-Ph 4-Pym CONH-Allyl
11-849 4-F-Ph 4-Pym CONH-Propargyl
11-850 4-F-Ph 4-Pym CONHPh
11-851 4-F-Ph 4-Pym CONH-3-Pyr
11-852 4-F-Ph 4-Pym CONHCH₂-4-Pyr
11-853 4-F-Ph 4-Pym CONH- (CH₂)₂-OH
11-854 4-F-Ph 4-Pym CONHCH (CH₂OH)₂       
11-855 4-F-Ph 4-Pym CONH- (CH₂)₂-OAc
11-856 4-F-Ph 4-Pym CONHCH₂CN
11-857 4-F-Ph 4-Pym CONH- (CH₂)₂-F
11-858 4-F-Ph 4-Pym CONH- (CH₂)₂-OMe
11-859 4-F-Ph 4-Pym CONH- (CH₂)₂-SMe
11-860 4-F-Ph 4-Pym CONH- (CH₂)₂-NH₂     
11-861 4-F-Ph 4-Pym CONH- (CH₂)₂-NHMe
11-862 4-F-Ph 4-Pym CONH- (CH₂)₂-N (Me)₂  
11-863 4-F-Ph 4-Pym CONHCH₂COOH
11-864 4-F-Ph 4-Pym CONHCH₂COOEt         
11-865 4-F-Ph 4-Pym CONHCH (Me) COOEt
11-866 4-F-Ph 4-Pym CONHCH₂CONH₂        
11-867 4-F-Ph 4-Pym SO₂NH₂              
11-868 4-F-Ph 4-Pym SO₂NHMe
11-869 4-F-Ph 4-Pym SO₂NHEt
11-870 4-F-Ph 4-Pym SO₂NHPr
11-871 4-F-Ph 4-Pym SO₂NH-i-Pr
11-872 4-F-Ph 4-Pym SO₂NHBu
11-873 4-F-Ph 4-Pym SO₂NHBn
11-874 4-F-Ph 4-Pym SO₂NMe₂             
11-875 4-F-Ph 4-Pym SO₂NH-c-Pr
11-876 4-F-Ph 4-Pym SO₂NH-c-Bu
11-877 4-F-Ph 4-Pym SO₂NH-c-Pen
11-878 4-F-Ph 4-Pym SO₂NH-c-Hex
11-879 4-F-Ph 4-Pym SO₂NH-c-Hep
11-880 4-F-Ph 4-Pym SO₂NHCH₂-c-Pr
11-881 4-F-Ph 4-Pym SO₂NH-Allyl
11-882 4-F-Ph 4-Pym SO₂NH-Propargyl
11-883 4-F-Ph 4-Pym SO₂NHPh
11-884 4-F-Ph 4-Pym SO₂NH-3-Pyr
11-885 4-F-Ph 4-Pym SO₂NHCH₂-4-Pyr
11-886 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OH
11-887 4-F-Ph 4-Pym SO₂NHCH (CH₂OH)₂      
11-888 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OAc
11-889 4-F-Ph 4-Pym SO₂NHCH₂CN
11-890 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-F
11-891 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-OMe
11-892 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-SMe
11-893 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-NH₂     
11-894 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-NHMe
11-895 4-F-Ph 4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
11-896 4-F-Ph 4-Pym SO₂NHCH₂COOH
11-897 4-F-Ph 4-Pym SO₂NHCH₂COOEt
11-898 4-F-Ph 4-Pym SO₂NHCH (Me) COOEt
11-899 4-F-Ph 4-Pym SO₂NHCH₂CONH₂        
11-900 4-F-Ph 4-Pym SO₂NHOH
11-901 4-F-Ph 4-Pym SO₂NHOMe
11-902 4-F-Ph 4-Pym SO₂NHOEt
11-903 4-F-Ph 4-Pym SO₂NHOPr
11-904 4-F-Ph 4-Pym SO₂NHOAllyl
11-905 4-F-Ph 4-Pym SO₂NHOBn
11-906 4-F-Ph 4-Pym SO₂NHNH₂            
11-907 4-F-Ph 4-Pym SO₂NHNHMe
11-908 4-F-Ph 4-Pym SO₂NHN (Me)₂         
11-909 4-F-Ph 2-MeO-4-Pym CONH₂              
11-910 4-F-Ph 2-MeO-4-Pym CONHMe
11-911 4-F-Ph 2-MeO-4-Pym CONHEt
11-912 4-F-Ph 2-MeO-4-Pym CONHPr
11-913 4-F-Ph 2-MeO-4-Pym CONH-i-Pr
11-914 4-F-Ph 2-MeO-4-Pym CONHBu
11-915 4-F-Ph 2-MeO-4-Pym CONHBn
11-916 4-F-Ph 2-MeO-4-Pym CONMe₂             
11-917 4-F-Ph 2-MeO-4-Pym CONH-c-Pr
11-918 4-F-Ph 2-MeO-4-Pym CONH-c-Bu
11-919 4-F-Ph 2-MeO-4-Pym CONH-c-Pen
11-920 4-F-Ph 2-MeO-4-Pym CONH-c-Hex
11-921 4-F-Ph 2-MeO-4-Pym CONH-c-Hep
11-922 4-F-Ph 2-MeO-4-Pym CONHCH₂-c-Pr
11-923 4-F-Ph 2-MeO-4-Pym CONH-Allyl
11-924 4-F-Ph 2-MeO-4-Pym CONH-Propargyl
11-925 4-F-Ph 2-MeO-4-Pym CONHPh
11-926 4-F-Ph 2-MeO-4-Pym CONH-3-Pyr
11-927 4-F-Ph 2-MeO-4-Pym CONHCH₂-4-Pyr
11-928 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OH
11-929 4-F-Ph 2-MeO-4-Pym CONHCH (CH₂OH)₂       
11-930 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OAc
11-931 4-F-Ph 2-MeO-4-Pym CONHCH₂CN            
11-932 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-F
11-933 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-OMe
11-934 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-SMe
11-935 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-NH₂      
11-936 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-NHMe
11-937 4-F-Ph 2-MeO-4-Pym CONH- (CH₂)₂-N (Me)₂   
11-938 4-F-Ph 2-MeO-4-Pym CONHCH₂COOH          
11-939 4-F-Ph 2-MeO-4-Pym CONHCH₂COOEt         
11-940 4-F-Ph 2-MeO-4-Pym CONHCH (Me) COOEt
11-941 4-F-Ph 2-MeO-4-Pym CONHCH₂CONH₂        
11-942 4-F-Ph 2-MeO-4-Pym SO₂NH₂              
11-943 4-F-Ph 2-MeO-4-Pym SO₂NHMe             
11-944 4-F-Ph 2-MeO-4-Pym SO₂NHEt             
11-945 4-F-Ph 2-MeO-4-Pym SO₂NHPr             
11-946 4-F-Ph 2-MeO-4-Pym SO₂NH-i-Pr          
11-947 4-F-Ph 2-MeO-4-Pym SO₂NHBu             
11-948 4-F-Ph 2-MeO-4-Pym SO₂NHBn             
11-949 4-F-Ph 2-MeO-4-Pym SO₂NMe₂             
11-950 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Pr          
11-951 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Bu
11-952 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Pen
11-953 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Hex
11-954 4-F-Ph 2-MeO-4-Pym SO₂NH-c-Hep
11-955 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂-c-Pr
11-956 4-F-Ph 2-MeO-4-Pym SO₂NH-Allyl          
11-957 4-F-Ph 2-MeO-4-Pym SO₂NH-Propargyl      
11-958 4-F-Ph 2-MeO-4-Pym SO₂NHPh              
11-959 4-F-Ph 2-MeO-4-Pym SO₂NH-3-Pyr          
11-960 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂-4-Pyr
11-961 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OH      
11-962 4-F-Ph 2-MeO-4-Pym SO₂NHCH (CH₂OH)₂     
11-963 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OAc     
11-964 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂CN           
11-965 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-F
11-966 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-OMe
11-967 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-SMe
11-968 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-NH₂     
11-969 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-NHMe
11-970 4-F-Ph 2-MeO-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
11-971 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂COOH
11-972 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂COOEt
11-973 4-F-Ph 2-MeO-4-Pym SO₂NHCH (Me) COOEt     
11-974 4-F-Ph 2-MeO-4-Pym SO₂NHCH₂CONH₂       
11-975 4-F-Ph 2-MeO-4-Pym SO₂NHOH             
11-976 4-F-Ph 2-MeO-4-Pym SO₂NHOMe
11-977 4-F-Ph 2-MeO-4-Pym SO₂NHOEt
11-978 4-F-Ph 2-MeO-4-Pym SO₂NHOPr
11-979 4-F-Ph 2-MeO-4-Pym SO₂NHOAllyl
11-980 4-F-Ph 2-MeO-4-Pym SO₂NHOBn
11-981 4-F-Ph 2-MeO-4-Pym SO₂NHNH₂            
11-982 4-F-Ph 2-MeO-4-Pym SO₂NHNHMe
11-983 4-F-Ph 2-MeO-4-Pym SO₂NHN (Me)₂         
11-984 4-F-Ph 2-NH₂-4-Pym             CONH₂              
11-985 4-F-Ph 2-NH₂-4-Pym             CONHMe
11-986 4-F-Ph 2-NH₂-4-Pym             CONHEt
11-987 4-F-Ph 2-NH₂-4-Pym             CONHPr
11-988 4-F-Ph 2-NH₂-4-Pym CONH-i-Pr
11-989 4-F-Ph 2-NH₂-4-Pym             CONHBu
11-990 4-F-Ph 2-NH₂-4-Pym             CONHBn
11-991 4-F-Ph 2-NH₂-4-Pym             CONMe₂              
11-992 4-F-Ph 2-NH₂-4-Pym             CONH-c-Pr
11-993 4-F-Ph 2-NH₂-4-Pym             CONH-c-Bu
11-994 4-F-Ph 2-NH₂-4-Pym             CONH-c-Pen
11-995 4-F-Ph 2-NH₂-4-Pym             CONH-c-Hex
11-996 4-F-Ph 2-NH₂-4-Pym             CONH-c-Hep
11-997 4-F-Ph 2-NH₂-4-Pym             CONHCH₂-c-Pr
11-998 4-F-Ph 2-NH₂-4-Pym             CONH-Allyl
11-999 4-F-Ph 2-NH₂-4-Pym CONH-Propargyl
11-1000 4-F-Ph 2-NH₂-4-Pym CONHPh
11-1001 4-F-Ph 2-NH₂-4-Pym CONH-3-Pyr
11-1002 4-F-Ph 2-NH₂-4-Pym CONHCH₂-4-Pyr
11-1003 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OH
11-1004 4-F-Ph 2-NH₂-4-Pym CONHCH (CH₂OH)₂      
11-1005 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OAc
11-1006 4-F-Ph 2-NH₂-4-Pym CONHCH₂CN
11-1007 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-F
11-1008 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-OMe
11-1009 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-SMe
11-1010 4-F-Ph 2-NH₂-4-Pym             CONH- (CH₂)₂-NH₂      
11-1011 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-NHMe
11-1012 4-F-Ph 2-NH₂-4-Pym CONH- (CH₂)₂-N (Me)₂   
11-1013 4-F-Ph 2-NH₂-4-Pym CONHCH₂COOH
11-1014 4-F-Ph 2-NH₂-4-Pym CONHCH₂COOEt
11-1015 4-F-Ph 2-NH₂-4-Pym CONHCH (Me) COOEt
11-1016 4-F-Ph 2-NH₂-4-Pym CONHCH₂CONH₂        
11-1017 4-F-Ph 2-NH₂-4-Pym SO₂NH₂             
11-1018 4-F-Ph 2-NH₂-4-Pym SO₂NHMe
11-1019 4-F-Ph 2-NH₂-4-Pym SO₂NHEt
11-1020 4-F-Ph 2-NH₂-4-Pym SO₂NHPr
11-1021 4-F-Ph 2-NH₂-4-Pym SO₂NH-i-Pr
11-1022 4-F-Ph 2-NH₂-4-Pym SO₂NHBu
11-1023 4-F-Ph 2-NH₂-4-Pym SO₂NHBn
11-1024 4-F-Ph 2-NH₂-4-Pym SO₂NMe₂            
11-1025 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Pr
11-1026 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Bu
11-1027 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Pen
11-1028 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Hex
11-1029 4-F-Ph 2-NH₂-4-Pym SO₂NH-c-Hep
11-1030 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂-c-Pr
11-1031 4-F-Ph 2-NH₂-4-Pym SO₂NH-Allyl
11-1032 4-F-Ph 2-NH₂-4-Pym SO₂NH-Propargyl
11-1033 4-F-Ph 2-NH₂-4-Pym SO₂NHPh
11-1034 4-F-Ph 2-NH₂-4-Pym SO₂NH-3-Pyr
11-1035 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂-4-Pyr
11-1036 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OH
11-1037 4-F-Ph 2-NH₂-4-Pym SO₂NHCH (CH₂OH)₂      
11-1038 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OAc
11-1039 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂CN
11-1040 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-F
11-1041 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-OMe
11-1042 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-SMe
11-1043 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-NH₂     
11-1044 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-NHMe
11-1045 4-F-Ph 2-NH₂-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
11-1046 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂COOH
11-1047 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂COOEt
11-1048 4-F-Ph 2-NH₂-4-Pym SO₂NHCH (Me) COOEt
11-1049 4-F-Ph 2-NH₂-4-Pym SO₂NHCH₂CONH₂        
11-1050 4-F-Ph 2-NH₂-4-Pym SO₂NHOH
11-1051 4-F-Ph 2-NH₂-4-Pym SO₂NHOMe
11-1052 4-F-Ph 2-NH₂-4-Pym SO₂NHOEt
11-1053 4-F-Ph 2-NH₂-4-Pym SO₂NHOPr
11-1054 4-F-Ph 2-NH₂-4-Pym SO₂NHOAllyl
11-1055 4-F-Ph 2-NH₂-4-Pym SO₂NHOBn
11-1056 4-F-Ph 2-NH₂-4-Pym SO₂NHNH₂            
11-1057 4-F-Ph 2-NH₂-4-Pym SO₂NHNHMe
11-1058 4-F-Ph 2-NH₂-4-Pym SO₂NHN (Me)₂        
11-1059 4-F-Ph 2-MeNH-4-Pym CONH₂              
11-1060 4-F-Ph 2-MeNH-4-Pym CONHMe
11-1061 4-F-Ph 2-MeNH-4-Pym CONHEt
11-1062 4-F-Ph 2-MeNH-4-Pym CONHPr
11-1063 4-F-Ph 2-MeNH-4-Pym CONH-i-Pr
11-1064 4-F-Ph 2-MeNH-4-Pym CONHBu
11-1065 4-F-Ph 2-MeNH-4-Pym CONHBn
11-1066 4-F-Ph 2-MeNH-4-Pym CONMe₂              
11-1067 4-F-Ph 2-MeNH-4-Pym CONH-c-Pr
11-1068 4-F-Ph 2-MeNH-4-Pym CONH-c-Bu
11-1069 4-F-Ph 2-MeNH-4-Pym CONH-c-Pen
11-1070 4-F-Ph 2-MeNH-4-Pym CONH-c-Hex
11-1071 4-F-Ph 2-MeNH-4-Pym CONH-c-Hep
11-1072 4-F-Ph 2-MeNH-4-Pym CONHCH₂-c-Pr
11-1073 4-F-Ph 2-MeNH-4-Pym CONH-Allyl
11-1074 4-F-Ph 2-MeNH-4-Pym CONH-Propargyl
11-1075 4-F-Ph 2-MeNH-4-Pym CONHPh
11-1076 4-F-Ph 2-MeNH-4-Pym CONH-3-Pyr
11-1077 4-F-Ph 2-MeNH-4-Pym CONHCH₂-4-Pyr
11-1078 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OH
11-1079 4-F-Ph 2-MeNH-4-Pym CONHCH (CH₂OH)₂       
11-1080 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OAc
11-1081 4-F-Ph 2-MeNH-4-Pym CONHCH₂CN
11-1082 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-F
11-1083 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-OMe
11-1084 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-SMe
11-1085 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-NH₂      
11-1086 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-NHMe
11-1087 4-F-Ph 2-MeNH-4-Pym CONH- (CH₂)₂-N (Me)₂   
11-1088 4-F-Ph 2-MeNH-4-Pym CONHCH₂COOH
11-1089 4-F-Ph 2-MeNH-4-Pym CONHCH₂COOEt
11-1090 4-F-Ph 2-MeNH-4-Pym CONHCH (Me) COOEt
11-1091 4-F-Ph 2-MeNH-4-Pym CONHCH₂CONH₂        
11-1092 4-F-Ph 2-MeNH-4-Pym SO₂NH₂              
11-1093 4-F-Ph 2-MeNH-4-Pym SO₂NHMe
11-1094 4-F-Ph 2-MeNH-4-Pym SO₂NHEt
11-1095 4-F-Ph 2-MeNH-4-Pym SO₂NHPr
11-1096 4-F-Ph 2-MeNH-4-Pym SO₂NH-i-Pr
11-1097 4-F-Ph 2-MeNH-4-Pym SO₂NHBu
11-1098 4-F-Ph 2-MeNH-4-Pym SO₂NHBn
11-1099 4-F-Ph 2-MeNH-4-Pym SO₂NMe₂             
11-1100 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Pr
11-1101 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Bu
11-1102 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Pen
11-1103 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Hex
11-1104 4-F-Ph 2-MeNH-4-Pym SO₂NH-c-Hep
11-1105 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂-c-Pr
11-1106 4-F-Ph 2-MeNH-4-Pym SO₂NH-Allyl
11-1107 4-F-Ph 2-MeNH-4-Pym SO₂NH-Propargyl
11-1108 4-F-Ph 2-MeNH-4-Pym SO₂NHPh
11-1109 4-F-Ph 2-MeNH-4-Pym SO₂NH-3-Pyr
11-1110 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂-4-Pyr
11-1111 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OH
11-1112 4-F-Ph 2-MeNH-4-Pym SO₂NHCH (CH₂OH)₂     
11-1113 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OAc
11-1114 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂CN
11-1115 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-F       
11-1116 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-OMe     
11-1117 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-SMe     
11-1118 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-NH₂     
11-1119 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-NHMe    
11-1120 4-F-Ph 2-MeNH-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
11-1121 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂COOH        
11-1122 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂COOEt       
11-1123 4-F-Ph 2-MeNH-4-Pym SO₂NHCH (Me) COOEt    
11-1124 4-F-Ph 2-MeNH-4-Pym SO₂NHCH₂CONH₂       
11-1125 4-F-Ph 2-MeNH-4-Pym SO₂NHOH
11-1126 4-F-Ph 2-MeNH-4-Pym SO₂NHOMe
11-1127 4-F-Ph 2-MeNH-4-Pym SO₂NHOEt
11-1128 4-F-Ph 2-MeNH-4-Pym SO₂NHOPr
11-1129 4-F-Ph 2-MeNH-4-Pym SO₂NHOAllyl
11-1130 4-F-Ph 2-MeNH-4-Pym SO₂NHOBn
11-1131 4-F-Ph 2-MeNH-4-Pym SO₂NHNH₂            
11-1132 4-F-Ph 2-MeNH-4-Pym SO₂NHNHMe
11-1133 4-F-Ph 2-MeNH-4-Pym SO₂NHN (Me)₂         
11-1134 4-F-Ph 2-BnNH-4-Pym CONH₂               
11-1135 4-F-Ph 2-BnNH-4-Pym CONHMe
11-1136 4-F-Ph 2-BnNH-4-Pym CONHEt
11-1137 4-F-Ph 2-BnNH-4-Pym CONHPr
11-1138 4-F-Ph 2-BnNH-4-Pym CONH-i-Pr
11-1139 4-F-Ph 2-BnNH-4-Pym CONHBu
11-1140 4-F-Ph 2-BnNH-4-Pym CONHBn
11-1141 4-F-Ph 2-BnNH-4-Pym CONMe₂             
11-1142 4-F-Ph 2-BnNH-4-Pym CONH-c-Pr
11-1143 4-F-Ph 2-BnNH-4-Pym CONH-c-Bu
11-1144 4-F-Ph 2-BnNH-4-Pym CONH-c-Pen
11-1145 4-F-Ph 2-BnNH-4-Pym CONH-c-Hex
11-1146 4-F-Ph 2-BnNH-4-Pym CONH-c-Hep
11-1147 4-F-Ph 2-BnNH-4-Pym CONHCH₂-c-Pr
11-1148 4-F-Ph 2-BnNH-4-Pym CONH-Allyl
11-1149 4-F-Ph 2-BnNH-4-Pym CONH-Propargyl
11-1150 4-F-Ph 2-BnNH-4-Pym CONHPh
11-1151 4-F-Ph 2-BnNH-4-Pym CONH-3-Pyr
11-1152 4-F-Ph 2-BnNH-4-Pym CONHCH₂-4-Pyr
11-1153 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OH
11-1154 4-F-Ph 2-BnNH-4-Pym CONHCH (CH₂OH)₂       
11-1155 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OAc
11-1156 4-F-Ph 2-BnNH-4-Pym CONHCH₂CN            
11-1157 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-F
11-1158 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-OMe
11-1159 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-SMe
11-1160 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-NH₂      
11-1161 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-NHMe
11-1162 4-F-Ph 2-BnNH-4-Pym CONH- (CH₂)₂-N (Me)₂  
11-1163 4-F-Ph 2-BnNH-4-Pym CONHCH₂COOH          
11-1164 4-F-Ph 2-BnNH-4-Pym CONHCH₂COOEt         
11-1165 4-F-Ph 2-BnNH-4-Pym CONHCH (Me) COOEt
11-1166 4-F-Ph 2-BnNH-4-Pym CONHCH₂CONH₂         
11-1167 4-F-Ph 2-BnNH-4-Pym SO₂NH₂              
11-1168 4-F-Ph 2-BnNH-4-Pym SO₂NHMe
11-1169 4-F-Ph 2-BnNH-4-Pym SO₂NHEt
11-1170 4-F-Ph 2-BnNH-4-Pym SO₂NHPr
11-1171 4-F-Ph 2-BnNH-4-Pym SO₂NH-i-Pr
11-1172 4-F-Ph 2-BnNH-4-Pym SO₂NHBu
11-1173 4-F-Ph 2-BnNH-4-Pym SO₂NHBn
11-1174 4-F-Ph 2-BnNH-4-Pym SO₂NMe₂             
11-1175 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Pr
11-1176 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Bu
11-1177 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Pen
11-1178 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Hex
11-1179 4-F-Ph 2-BnNH-4-Pym SO₂NH-c-Hep
11-1180 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂-c-Pr
11-1181 4-F-Ph 2-BnNH-4-Pym SO₂NH-Allyl
11-1182 4-F-Ph 2-BnNH-4-Pym SO₂NH-Propargyl
11-1183 4-F-Ph 2-BnNH-4-Pym SO₂NHPh
11-1184 4-F-Ph 2-BnNH-4-Pym SO₂NH-3-Pyr
11-1185 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂-4-Pyr
11-1186 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OH
11-1187 4-F-Ph 2-BnNH-4-Pym SO₂NHCH (CH₂OH)₂      
11-1188 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OAc
11-1189 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂CN
11-1190 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-F
11-1191 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-OMe
11-1192 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-SMe
11-1193 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-NH₂     
11-1194 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-NHMe
11-1195 4-F-Ph 2-BnNH-4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
11-1196 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂COOH         
11-1197 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂COOEt
11-1198 4-F-Ph 2-BnNH-4-Pym SO₂NHCH (Me) COOEt     
11-1199 4-F-Ph 2-BnNH-4-Pym SO₂NHCH₂CONH₂       
11-1200 4-F-Ph 2-BnNH-4-Pym SO₂NHOH
11-1201 4-F-Ph 2-BnNH-4-Pym SO₂NHOMe
11-1202 4-F-Ph 2-BnNH-4-Pym SO₂NHOEt
11-1203 4-F-Ph 2-BnNH-4-Pym SO₂NHOPr
11-1204 4-F-Ph 2-BnNH-4-Pym SO₂NHOAllyl
11-1205 4-F-Ph 2-BnNH-4-Pym SO₂NHOBn
11-1206 4-F-Ph 2-BnNH-4-Pym SO₂NHNH₂            
11-1207 4-F-Ph 2-BnNH-4-Pym SO₂NHNHMe
11-1208 4-F-Ph 2-BnNH-4-Pym SO₂NHN (Me)₂          
11-1209 4-F-Ph (α-Me-BnNH) -4-Pym CONH₂              
11-1210 4-F-Ph (α-Me-BnNH) -4-Pym CONHMe
11-1211 4-F-Ph (α-Me-BnNH) -4-Pym CONHEt
11-1212 4-F-Ph (α-Me-BnNH) -4-Pym CONHPr
11-1213 4-F-Ph (α-Me-BnNH) -4-Pym CONH-i-Pr
11-1214 4-F-Ph (α-Me-BnNH) -4-Pym CONHBu
11-1215 4-F-Ph (α-Me-BnNH) -4-Pym CONHBn
11-1216 4-F-Ph (α-Me-BnNH) -4-Pym CONMe₂             
11-1217 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Pr
11-1218 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Bu
11-1219 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Pen
11-1220 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Hex
11-1221 4-F-Ph (α-Me-BnNH) -4-Pym CONH-c-Hep
11-1222 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂-c-Pr
11-1223 4-F-Ph (α-Me-BnNH) -4-Pym CONH-Allyl
11-1224 4-F-Ph (α-Me-BnNH) -4-Pym CONH-Propargyl
11-1225 4-F-Ph (α-Me-BnNH) -4-Pym CONHPh
11-1226 4-F-Ph (α-Me-BnNH) -4-Pym CONH-3-Pyr
11-1227 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂-4-Pyr        
11-1228 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OH
11-1229 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH (CH₂OH)₂       
11-1230 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OAc
11-1231 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂CN            
11-1232 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-F
11-1233 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-OMe
11-1234 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-SMe
11-1235 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-NH₂      
11-1236 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-NHMe
11-1237 4-F-Ph (α-Me-BnNH) -4-Pym CONH- (CH₂)₂-N (Me)₂  
11-1238 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂COOH
11-1239 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂COOEt
11-1240 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH (Me) COOEt
11-1241 4-F-Ph (α-Me-BnNH) -4-Pym CONHCH₂CONH₂        
11-1242 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH₂              
11-1243 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHMe
11-1244 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHEt
11-1245 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHPr
11-1246 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-i-Pr
11-1247 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHBu
11-1248 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHBn
11-1249 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NMe₂             
11-1250 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Pr
11-1251 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Bu
11-1252 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Pen
11-1253 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Hex
11-1254 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-c-Hep
11-1255 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂-c-Pr
11-1256 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-Allyl
11-1257 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-Propargyl
11-1258 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHPh
11-1259 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH-3-Pyr
11-1260 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂-4-Pyr
11-1261 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OH
11-1262 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH (CH₂OH)₂      
11-1263 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OAc
11-1264 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂CN
11-1265 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-F
11-1266 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-OMe
11-1267 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-SMe
11-1268 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-NH₂     
11-1269 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-NHMe
11-1270 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NH- (CH₂)₂-N (Me)₂  
11-1271 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂COOH
11-1272 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂COOEt
11-1273 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH (Me) COOEt
11-1274 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHCH₂CONH₂        
11-1275 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOH
11-1276 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOMe
11-1277 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOEt
11-1278 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOPr
11-1279 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOAllyl
11-1280 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHOBn
11-1281 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHNH₂            
11-1282 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHNHMe           
11-1283 4-F-Ph (α-Me-BnNH) -4-Pym SO₂NHN (Me)₂          
11-1284 4-F-Ph 4-Pyr SO₂NHMe               
11-1285 4-F-Ph 4-Pyr SOMe                  
11-1286 4-F-Ph 4-Pyr SO₂Me                 
11-1287 3-Cl-4-F-Ph 4-Pyr SO₂NHMe               
11-1288 3-Cl-4-F-Ph 4-Pyr SOMe                  
11-1289 3-Cl-4-F-Ph 4-Pyr SO₂Me                 
―――――――――――――――――――――――――――――――――――
Table 12

―――――――――――――――――――――
Compound AR ⁵
No .――――――――――――――――――――――
12-1 Ring 15 CONH ₂
12-2 Ring 15 SO ₂ NHMe
12-3 Ring 15 SO ₂ Me
12-4 Ring 16 CONH ₂
12-5 Ring 16 SO ₂ NHMe
12-6 Ring 16 SO ₂ Me
12-7 Ring 17 CONH ₂
12-8 Ring 17 SO ₂ NHMe
12-9 Ring 17 SO ₂ Me
12-10 Ring 18 CONH ₂
12-11 Ring 18 SO ₂ NHMe
12-12 Ring 18 SO ₂ Me
12-13 Ring 19 CONH ₂
12-14 Ring 19 SO ₂ NHMe
12-15 Ring 19 SO ₂ Me
12-16 Ring 20 CONH ₂
12-17 Ring 20 SO ₂ NHMe
12-18 Ring 20 SO ₂ Me
12-19 Ring 21 CONH ₂
12-20 Ring 21 SO ₂ NHMe
12-21 Ring 21 SO ₂ Me
12-22 Ring 22 CONH ₂
12-23 Ring 22 SO ₂ NHMe
12-24 Ring 22 SO ₂ Me
12-25 Ring 23 CONH ₂
12-26 Ring 23 SO ₂ NHMe
12-27 Ring 23 SO ₂ Me
12-28 Ring 24 CONH ₂
12-29 Ring 24 SO ₂ NHMe
12-30 Ring 24 SO ₂ Me
12-31 Ring 25 CONH ₂
12-32 Ring 25 SO ₂ NHMe
12-33 Ring 25 SO ₂ Me
12-34 Ring 26 CONH ₂
12-35 Ring 26 SO ₂ NHMe
12-36 Ring 26 SO ₂ Me
12-37 Ring 27 CONH ₂
12-38 Ring 27 SO ₂ NHMe
12-39 Ring 27 SO ₂ Me
12-40 Ring 28 CONH ₂
12-41 Ring 28 SO ₂ NHMe
12-42 Ring 28 SO ₂ Me
12-43 Ring 29 CONH ₂
12-44 Ring 29 SO ₂ NHMe
12-45 Ring 29 SO ₂ Me
12-46 Ring 30 CONH ₂
12-47 Ring 30 SO ₂ NHMe
12-48 Ring 30 SO ₂ Me
12-49 Ring 31 CONH ₂
12-50 Ring 31 SO ₂ NHMe
12-51 Ring 31 SO ₂ Me
12-52 Ring 32 CONH ₂
12-53 Ring 32 SO ₂ NHMe
12-54 Ring 32 SO ₂ Me
12-55 Ring 33 CONH ₂
12-56 Ring 33 SO ₂ NHMe
12-57 Ring 33 SO ₂ Me
12-58 Ring 34 CONH ₂
12-59 Ring 34 SO ₂ NHMe
12-60 Ring 34 SO ₂ Me
12-61 Ring 35 CONH ₂
12-62 Ring 35 SO ₂ NHMe
12-63 Ring 35 SO ₂ Me
12-64 Ring 36 CONH ₂
12-65 Ring 36 SO ₂ NHMe
12-66 Ring 36 SO ₂ Me
12-67 Ring 37 CONH ₂
12-68 Ring 37 SO ₂ NHMe
12-69 Ring 37 SO ₂ Me
12-70 Ring 38 CONH ₂
12-71 Ring 38 SO ₂ NHMe
12-72 Ring 38 SO ₂ Me
12-73 Ring 39 CONH ₂
12-74 Ring 39 SO ₂ NHMe
12-75 Ring 39 SO ₂ Me
12-76 Ring 40 CONH ₂
12-77 Ring 40 SO ₂ NHMe
12-78 Ring 40 SO ₂ Me
12-79 Ring 41 CONH ₂
12-80 Ring 41 SO ₂ NHMe
12-81 Ring 41 SO ₂ Me
12-82 Ring 42 CONH ₂
12-83 Ring 42 SO ₂ NHMe
12-84 Ring 42 SO ₂ Me
12-85 Ring 43 CONH ₂
12-86 Ring 43 SO ₂ NHMe
12-87 Ring 43 SO ₂ Me
12-88 Ring 44 CONH ₂
12-89 Ring 44 SO ₂ NHMe
12-90 Ring 44 SO ₂ Me
12-91 Ring 45 CONH ₂
12-92 Ring 45 SO ₂ NHMe
12-93 Ring 45 SO ₂ Me
12-94 Ring 46 CONH ₂
12-95 Ring 46 SO ₂ NHMe
12-96 Ring 46 SO ₂ Me
12-97 Ring 47 CONH ₂
12-98 Ring 47 SO ₂ NHMe
12-99 Ring 47 SO ₂ Me
12-100 Ring 48 CONH ₂
12-101 Ring 48 SO ₂ NHMe
12-102 Ring 48 SO ₂ Me
12-103 Ring 49 CONH ₂
12-104 Ring 49 SO ₂ NHMe
12-105 Ring 49 SO ₂ Me
12-106 Ring 50 CONH ₂
12-107 Ring 50 SO ₂ NHMe
12-108 Ring 50 SO ₂ Me
12-109 Ring 51 CONH ₂
12-109 Ring 51 SO ₂ NHMe
12-110 Ring 51 SO ₂ Me
―――――――――――――――――――――
Table 13

―――――――――――――――――――――
Compound AR ⁵
No .――――――――――――――――――――――
13-1 Ring 15 CONH ₂
13-2 Ring 15 SO ₂ NHMe
13-3 Ring 15 SO ₂ Me
13-4 Ring 16 CONH ₂
13-5 Ring 16 SO ₂ NHMe
13-6 Ring 16 SO ₂ Me
13-7 Ring 17 CONH ₂
13-8 Ring 17 SO ₂ NHMe
13-9 Ring 17 SO ₂ Me
13-10 Ring 18 CONH ₂
13-11 Ring 18 SO ₂ NHMe
13-12 Ring 18 SO ₂ Me
13-13 Ring 19 CONH ₂
13-14 Ring 19 SO ₂ NHMe
13-15 Ring 19 SO ₂ Me
13-16 Ring 20 CONH ₂
13-17 Ring 20 SO ₂ NHMe
13-18 Ring 20 SO ₂ Me
13-19 Ring 21 CONH ₂
13-20 Ring 21 SO ₂ NHMe
13-21 Ring 21 SO ₂ Me
13-22 Ring 22 CONH ₂
13-23 Ring 22 SO ₂ NHMe
13-24 Ring 22 SO ₂ Me
13-25 Ring 23 CONH ₂
13-26 Ring 23 SO ₂ NHMe
13-27 Ring 23 SO ₂ Me
13-28 Ring 24 CONH ₂
13-29 Ring 24 SO ₂ NHMe
13-30 Ring 24 SO ₂ Me
13-31 Ring 25 CONH ₂
13-32 Ring 25 SO ₂ NHMe
13-33 Ring 25 SO ₂ Me
13-34 Ring 26 CONH ₂
13-35 Ring 26 SO ₂ NHMe
13-36 Ring 26 SO ₂ Me
13-37 Ring 27 CONH ₂
13-38 Ring 27 SO ₂ NHMe
13-39 Ring 27 SO ₂ Me
13-40 Ring 28 CONH ₂
13-41 Ring 28 SO ₂ NHMe
13-42 Ring 28 SO ₂ Me
13-43 Ring 29 CONH ₂
13-44 Ring 29 SO ₂ NHMe
13-45 Ring 29 SO ₂ Me
13-46 Ring 30 CONH ₂
13-47 Ring 30 SO ₂ NHMe
13-48 Ring 30 SO ₂ Me
13-49 Ring 31 CONH ₂
13-50 Ring 31 SO ₂ NHMe
13-51 Ring 31 SO ₂ Me
13-52 Ring 32 CONH ₂
13-53 Ring 32 SO ₂ NHMe
13-54 Ring 32 SO ₂ Me
13-55 Ring 33 CONH ₂
13-56 Ring 33 SO ₂ NHMe
13-57 Ring 33 SO ₂ Me
13-58 Ring 34 CONH ₂
13-59 Ring 34 SO ₂ NHMe
13-60 Ring 34 SO ₂ Me
13-61 Ring 35 CONH ₂
13-62 Ring 35 SO ₂ NHMe
13-63 Ring 35 SO ₂ Me
13-64 Ring 36 CONH ₂
13-65 Ring 36 SO ₂ NHMe
13-66 Ring 36 SO ₂ Me
13-67 Ring 37 CONH ₂
13-68 Ring 37 SO ₂ NHMe
13-69 Ring 37 SO ₂ Me
13-70 Ring 38 CONH ₂
13-71 Ring 38 SO ₂ NHMe
13-72 Ring 38 SO ₂ Me
13-73 Ring 39 CONH ₂
13-74 Ring 39 SO ₂ NHMe
13-75 Ring 39 SO ₂ Me
13-76 Ring 40 CONH ₂
13-77 Ring 40 SO ₂ NHMe
13-78 Ring 40 SO ₂ Me
13-79 Ring 41 CONH ₂
13-80 Ring 41 SO ₂ NHMe
13-81 Ring 41 SO ₂ Me
13-82 Ring 42 CONH ₂
13-83 Ring 42 SO ₂ NHMe
13-84 Ring 42 SO ₂ Me
13-85 Ring 43 CONH ₂
13-86 Ring 43 SO ₂ NHMe
13-87 Ring 43 SO ₂ Me
13-88 Ring 44 CONH ₂
13-89 Ring 44 SO ₂ NHMe
13-90 Ring 44 SO ₂ Me
13-91 Ring 45 CONH ₂
13-92 Ring 45 SO ₂ NHMe
13-93 Ring 45 SO ₂ Me
13-94 Ring 46 CONH ₂
13-95 Ring 46 SO ₂ NHMe
13-96 Ring 46 SO ₂ Me
13-97 Ring 47 CONH ₂
13-98 Ring 47 SO ₂ NHMe
13-99 Ring 47 SO ₂ Me
13-100 Ring 48 CONH ₂
13-101 Ring 48 SO ₂ NHMe
13-102 Ring 48 SO ₂ Me
13-103 Ring 49 CONH ₂
13-104 Ring 49 SO ₂ NHMe
13-105 Ring 49 SO ₂ Me
13-106 Ring 50 CONH ₂
13-107 Ring 50 SO ₂ NHMe
13-108 Ring 50 SO ₂ Me
13-109 Ring 51 CONH ₂
13-110 Ring 51 SO ₂ NHMe
13-111 Ring 51 SO ₂ Me
―――――――――――――――――――――
Table 14

――――――――――――――――――――
Compound R ¹ R ⁵
No .――――――――――――――――――――
14-1 4-F-Ph 2-COOH
14-2 4-F-Ph 3-COOH
14-3 4-F-Ph 2-CONH ₂
14-4 4-F-Ph 3-CONH ₂
14-5 4-F-Ph 3-CONHMe
14-6 4-F-Ph 3-CONHEt
14-7 4-F-Ph 3-CONHPr
14-8 4-F-Ph 3-CONH-i-Pr
14-9 4-F-Ph 2-SO ₂ NH ₂
14-10 4-F-Ph 3-SO ₂ NH ₂
14-11 4-F-Ph 3-SO ₂ NHMe
14-12 4-F-Ph 3-SO ₂ NHEt
14-13 4-F-Ph 3-SO ₂ NHPr
14-14 4-F-Ph 3-SO ₂ NH-i-Pr
14-15 4-F-Ph 2-SOMe
14-16 4-F-Ph 3-SOMe
14-17 4-F-Ph 2-SO ₂ Me
14-18 4-F-Ph 3-SO ₂ Me
14-19 3-Cl-4-F-Ph 2-COOH
14-20 3-Cl-4-F-Ph 3-COOH
14-21 3-Cl-4-F-Ph 2-CONH ₂
14-22 3-Cl-4-F-Ph 3-CONH ₂
14-23 3-Cl-4-F-Ph 3-CONHMe
14-24 3-Cl-4-F-Ph 3-CONHEt
14-25 3-Cl-4-F-Ph 3-CONHPr
14-26 3-Cl-4-F-Ph 3-CONH-i-Pr
14-27 3-Cl-4-F-Ph 2-SO ₂ NH ₂
14-28 3-Cl-4-F-Ph 3-SO ₂ NH ₂
14-29 3-Cl-4-F-Ph 3-SO ₂ NHMe
14-30 3-Cl-4-F-Ph 3-SO ₂ NHEt
14-31 3-Cl-4-F-Ph 3-SO ₂ NHPr
14-32 3-Cl-4-F-Ph 3-SO ₂ NH-i-Pr
14-33 3-Cl-4-F-Ph 2-SOMe
14-34 3-Cl-4-F-Ph 3-SOMe
14-35 3-Cl-4-F-Ph 2-SO ₂ Me
14-36 3-Cl-4-F-Ph 3-SO ₂ Me
――――――――――――――――――――
In the above table, “Ac” represents acetyl, “Allyl” represents allyl, “Bn” represents benzyl, “Bu” represents butyl, “c-Bu” represents cyclobutyl, and “Et” represents “C-Hep” indicates cycloheptyl, “c-Hex” indicates cyclohexyl, “Me” indicates methyl, “c-Pen” indicates cyclopentyl, “Ph” indicates phenyl , “Propargyl” indicates propargyl, “Pr” indicates propyl, “i-Pr” indicates isopropyl, “c-Pr” indicates cyclopropyl, “Pym” indicates pyrimidinyl, and “Pyr” Represents pyridyl, “═CH ₂ ” represents methylidenyl and “═O” represents carbonyl.

  The indications of “Ring 1” to “Ring 14” in the column A of Table 6 indicate the rings in Table 15 below, respectively.

In each ring in Table 15, R ⁵ is bonded to the bond described on the rightmost side.

  The indications of “Ring 15” to “Ring 51” in the column A of Table 12 and Table 13 indicate the rings of Table 16 below, respectively.

In each ring in Table 16, R ¹ (4-F-Ph) is bonded to the leftmost bond.

  In Tables 10 and 11, mention is made of compounds in which a hydrogen atom is substituted for a nitrogen atom in the pyrazole ring corresponding to A in the general formula (1). Has variability.

The illustrations in Tables 10 and 11 above are intended for any compound.

In Table 1 to Table 14, suitable compounds are exemplified compound numbers 1-1 to 1-4, 1-9 to 1-14, 1-17 to 1-20, 1-23 to 1-24, 1- 28 to 1-30, 1-32 to 1-34, 1-39 to 1-40, 1-43 to 1-46, 1-51 to 1-53, 1-57 to 1-63, 1-66 to 1-72, 1-75 to 1-93, 1-96 to 1-103, 1-108 to 1-110, 1-112 to 1-115, 1-120 to 1-123, 1-128 to 1- 133, 1-136 to 1-139, 1-142 to 1-143, 1-147 to 1-149, 1-151 to 1-153, 1-158 to 1-159, 1-162 to 1-165, 1-170 to 1-172, 1-176 to 1-182, 1-185 to -191, 1-194 to 1-212, 1-215 to 1-222, 1-227 to 1-229, 1-231 to 1-234, 1-239 to 1-224, 1-247 to 1-252 1-255 to 1-258, 1-261 to 1-262, 1-266 to 1-268, 1-270 to 1-272, 1-277 to 1-278, 1-281 to 1-284, 1 -289 to 1-291, 1-295 to 1-301, 1-304 to 1-310, 1-313 to 1-331, 1-334 to 1-341, 1-346 to 1-348, 1-350 1 to 353, 1-358 to 1-361, 1-366 to 1-371, 1-374 to 1-377, 1-380 to 1-381, 1-385 to 1-387, 1-389 to 1 -391, 1- 96 to 1-397, 1-400 to 1-403, 1-408 to 1-410, 1-414 to 1-420, 1-423 to 1-429, 1-432 to 1-450, 1-453 to 1-460, 1-465 to 1-467, 1-469 to 1-472, 1-477 to 1-480, 1-485 to 1-490, 1-493 to 1-496, 1-499 to 1- 500, 1-504 to 1-506, 1-508 to 1-510, 1-515 to 1-516, 1-519 to 1-522, 1-527 to 1-529, 1-533 to 1-539, 1-542 to 1-548, 1-551 to 1-569, 1-572 to 1-579, 1-584 to 1-586, 1-588 to 1-591, 1-596 to 1-599, 1- 604 to 1-60 9, 1-612 to 1-615, 1-618 to 1-619, 1-623 to 1-625, 1-627 to 1-629, 1-634 to 1-635, 1-638 to 1-641, 1-646 to 1-648, 1-652 to 1-658, 1-661 to 1-667, 1-670 to 1-688, 1-691 to 1-698, 1-703 to 1-705, 1- 707 to 1-710, 1-715 to 1-718, 1-723 to 1-728, 1-731 to 1-734, 1-737 to 1-738, 1-742 to 1-744, 1-746 to 1-748, 1-753 to 1-754, 1-757 to 1-760, 1-765 to 1-767, 1-771 to 1-777, 1-780 to 1-786, 1-789 to 1- 807, 1-810 1-817, 1-822 to 1-824, 1-826 to 1-829, 1-834 to 1-839, 1-842 to 1-845, 1-848 to 1-849, 1-853 to 1- 855, 1-857 to 1-859, 1-864 to 1-865, 1-867 to 1-882, 1-885 to 1-892, 1-897 to 1-899, 1-901 to 1-904, 1-909 to 1-914, 1-917 to 1-920, 1-923 to 1-924, 1-928 to 1-930, 1-932 to 1-934, 1-939 to 1-940, 1- 942 to 1-957, 1-960 to 1-967, 1-972 to 1-974, 1-976 to 1-979, 1-984 to 1-989, 1-992 to 1-995, 1-998 to 1-999, 1 1003 to 1-1005, 1-1007 to 1-1009, 1-1014 to 1-1015, 1-1017 to 1-1032, 1-1035 to 1-1042, 1-1047 to 1-1049, 1-1051 to 1-1054, 1-1059 to 1-1064, 1-1067 to 1-1070, 1-1073 to 1-1074, 1-1078 to 1-1080, 1-1082 to 1-1084, 1-1089 to 1- 1090, 1-1092 to 1-1107, 1-1110 to 1-1117, 1-1122 to 1-1124, 1-1126 to 1-1129, 1-1134 to 1-1139, 1-1142 to 1-1145, 1-1148 to 1-1149, 1-1153 to 1-1155, 1-1157 to 1-1159, 1-116 4 to 1-1165, 1-1167 to 1-1182, 1-1185 to 1-1192, 1-1197 to 1-1199, 1-1201 to 1-1204, 1-1209 to 1-1214, 1-1217 to 1-1220, 1-1223 to 1-1224, 1-1228 to 1-1230, 1-1232 to 1-1234, 1-1239 to 1-1240, 1-1242 to 1-1257, 1-1260 to 1- 1267, 1-1272 to 1-1274, 1-1276 to 1-1279, 1-1284 to 1-1285, 1-1287, 1-1290, 1-1293 to 1-1294, 1-1296, 1-1299, 1-1302 to 1-1303, 1-1305, 1-1308, 1-131 to 1-1312, 1-1314, 1-13 7, 1-1320 to 1-1321, 1-1323, 1-1326, 1-1329 to 1-1330, 1-132, 1-1335, 1-1338, 1-1134 to 1-1343, 1-1346 to 1-1348,
2-1 to 2-6, 2-11 to 2-16, 2-21 to 2-26, 2-31 to 2-36,
3-5, 3-11, 3-16, 3-18, 3-23, 3-29, 3-34, 3-36, 3-38, 3-43, 3-47 to 3-50,
6-2, 6-8, 6-13, 6-16, 6-19, 6-23, 6-29, 6-34, 6-37, 6-40, 6-44, 6-50, 6- 55, 6-58, 6-61, 6-65, 6-71, 6-76, 6-79, 6-82, 6-86, 6-92, 6-97, 6-100, 6-103, 6-107, 6-113, 6-118, 6-121, 6-124, 6-128, 6-134, 6-139, 6-142, 6-145, 6-149, 6-155, 6- 160, 6-163, 6-166, 6-170, 6-176, 6-181, 6-184, 6-187, 6-191, 6-197, 6-202, 6-205, 6-208, 6-212, 6-218, 6-223, 6-226, 6-229, 6-233, 6-239, 6-244, 6-247, 6-25 6-254, 6-260, 6-265, 6-268, 6-271, 6-275, 6-281, 6-286, 6-289, 6-292, 6-296, 6-302, 6 -307, 6-310, 6-313, 6-317, 6-323, 6-328, 6-331, 6-334, 6-338, 6-344, 6-349, 6-352, 6-355 6-359, 6-365, 6-370, 6-373, 6-376, 6-380, 6-386, 6-391, 6-394, 6-397, 6-401, 6-407, 6 -412, 6-415, 6-418, 6-422, 6-428, 6-433, 6-436, 6-439, 6-443, 6-449, 6-454, 6-457, 6-460 6-464, 6-470, 6-475, 6-478, 6-481, 6 485, 6-491, 6-496, 6-499, 6-502, 6-506, 6-512, 6-517, 6-520, 6-523, 6-527, 6-533, 6-538, 6-541, 6-544, 6-548, 6-554, 6-559, 6-562, 6-565, 6-569, 6-575, 6-580, 6-583, 6-586,
7-1 to 7-4, 7-9 to 7-14, 7-17 to 7-20, 7-23 to 7-24, 7-28 to 7-30, 7-32 to 7-34, 7- 39 to 7-40, 7-43 to 7-46, 7-51 to 7-53, 7-57 to 7-63, 7-66 to 7-72, 7-75 to 7-93, 7-96 to 7-103, 7-108 to 7-110, 7-112 to 7-115, 7-120 to 7-123, 7-128 to 7-133, 7-136 to 7-139, 7-142 to 7- 143, 7-147 to 7-149, 7-151 to 7-153, 7-158 to 7-159, 7-162 to 7-165, 7-170 to 7-172, 7-176 to 7-182, 7-185 to 7-191, 7-194 to 7-212, 7-215 to 7-2 2, 7-227 to 7-229, 7-231 to 7-234, 7-239 to 7-242, 7-247 to 7-252, 7-255 to 7-258, 7-261 to 7-262, 7-266 to 7-268, 7-270 to 7-272, 7-277 to 7-278, 7-281 to 7-284, 7-289 to 7-291, 7-295 to 7-301, 7- 304 to 7-310, 7-313 to 7-331, 7-334 to 7-341, 7-346 to 7-348, 7-350 to 7-353, 7-358 to 7-361, 7-366 to 7-371, 7-374 to 7-377, 7-380 to 7-381, 7-385 to 7-387, 7-389 to 7-391, 7-396 to 7-397, 7-400 to 7- 403, 7-408 7-410, 7-414 to 7-420, 7-423 to 7-429, 7-432 to 7-450, 7-453 to 7-460, 7-465 to 7-467, 7-469 to 7 -472, 7-477 to 7-480, 7-485 to 7-490, 7-493 to 7-496, 7-499 to 7-500, 7-504 to 7-506, 7-508 to 7-510 7-515 to 7-516, 7-519 to 7-522, 7-527 to 7-529, 7-533 to 7-539, 7-542 to 7-548, 7-551 to 7-569, 7 -572 to 7-579, 7-584 to 7-586, 7-588 to 7-591, 7-596 to 7-599, 7-604 to 7-609, 7-612 to 7-615, 7-618 To 7-619, 7 -623 to 7-625, 7-627 to 7-629, 7-634 to 7-635, 7-638 to 7-641, 7-646 to 7-648, 7-652 to 7-658, 7-661 To 7-667, 7-670 to 7-688, 7-691 to 7-698, 7-703 to 7-705, 7-707 to 7-710, 7-715 to 7-718, 7-723 to 7 -728, 7-731 to 7-734, 7-737 to 7-738, 7-742 to 7-744, 7-746 to 7-748, 7-753 to 7-754, 7-757 to 7-760 7-765 to 7-767, 7-771 to 7-777, 7-780 to 7-786, 7-789 to 7-807, 7-810 to 7-817, 7-822 to 7-824, 7 -826 to 7- 29, 7-834 to 7-839, 7-842 to 7-845, 7-848 to 7-849, 7-853 to 7-855, 7-857 to 7-859, 7-864 to 7-865, 7-867 to 7-882, 7-885 to 7-892, 7-897 to 7-899, 7-901 to 7-904, 7-909 to 7-914, 7-917 to 7-920, 7- 923 to 7-924, 7-928 to 7-930, 7-932 to 7-934, 7-939 to 7-940, 7-942 to 7-957, 7-960 to 7-967, 7-972 to 7-974, 7-976 to 7-979, 7-984 to 7-989, 7-992 to 7-995, 7-998 to 7-999, 7-1003 to 7-1005, 7-1007 to 7- 1009, -1014 to 7-1015, 7-1017 to 7-1032, 7-1035 to 7-1042, 7-1047 to 7-1049, 7-1051 to 7-1054, 7-1059 to 7-1064, 7-1067 To 7-1070, 7-1073 to 7-1074, 7-1078 to 7-1080, 7-1082 to 7-1084, 7-1089 to 7-1090, 7-1092 to 7-1107, 7-1110 to 7 -1117, 7-1122 to 7-1124, 7-1126 to 7-1129, 7-1134 to 7-1139, 7-1142 to 7-1145, 7-1148 to 7-1149, 7-1153 to 7-1155 7-1157 to 7-1159, 7-1164 to 7-1165, 7-1167 to 7-1182, 7-11 85 to 7-1192, 7-1197 to 7-1199, 7-1201 to 7-1204, 7-1209 to 7-1214, 7-1217 to 7-1220, 7-1223 to 7-1224, 7-1228 to 7-1230, 7-1232 to 7-1234, 7-1239 to 7-1240, 7-1242 to 7-1257, 7-1260 to 7-1267, 7-1272 to 7-1274, 7-1276 to 7- 1279, 7-1284 to 7-1289,
8-2, 8-8, 8-13, 8-16, 8-19, 8-23, 8-29, 8-34, 8-37, 8-40,
9-2, 9-8, 9-13, 9-16, 9-19, 9-23, 9-29, 9-34, 9-37, 9-40, 9-44, 9-50, 9- 55, 9-58, 9-61, 9-65, 9-71, 9-76, 9-79, 9-82, 9-86, 9-92, 9-97, 9-100, 9-103, 9-107, 9-113, 9-118, 9-121, 9-124, 9-128, 9-134, 9-139, 9-142, 9-145, 9-149, 9-155, 9- 160, 9-163, 9-166, 9-170, 9-176, 9-181, 9-184, 9-187, 9-191, 9-197, 9-202, 9-205, 9-208, 9-212, 9-218, 9-223, 9-226, 9-229, 9-233, 9-239, 9-244, 9-247, 9-25 9-254, 9-260, 9-265, 9-268, 9-271, 9-275, 9-281, 9-286, 9-289, 9-292, 9-296, 9-302, 9 -307, 9-310, 9-313, 9-317, 9-323, 9-328, 9-331, 9-334, 9-338, 9-344, 9-349, 9-352, 9-355 9-359, 9-365, 9-370, 9-373, 9-376, 9-380, 9-386, 9-391, 9-394, 9-397, 9-401, 9-407, 9 -412, 9-415, 9-418, 9-422, 9-428, 9-433, 9-436, 9-439, 9-443, 9-449, 9-454, 9-457, 9-460 9-464, 9-470, 9-475, 9-478, 9-481, 9 485, 9-491, 9-496, 9-499, 9-502, 9-506, 9-512, 9-517, 9-520, 9-523, 9-527, 9-533, 9-538, 9-541, 9-544, 9-548, 9-554, 9-559, 9-562, 9-565, 9-569, 9-575, 9-580, 9-583, 9-586,
10-1 to 10-4, 10-9 to 10-14, 10-17 to 10-20, 10-23 to 10-24, 10-28 to 10-30, 10-32 to 10-34, 10- 39 to 10-40, 10-43 to 10-46, 10-51 to 10-53, 10-57 to 10-63, 10-66 to 10-72, 10-75 to 10-93, 10-96 to 10-103, 10-108 to 10-110, 10-112 to 10-115, 10-120 to 10-123, 10-128 to 10-133, 10-136 to 10-139, 10-142 to 10- 143, 10-147 to 10-149, 10-151 to 10-153, 10-158 to 10-159, 10-162 to 10-165, 10-170 to 10-172, 1 -176 to 10-182, 10-185 to 10-191, 10-194 to 10-212, 10-215 to 10-222, 10-227 to 10-229, 10-231 to 10-234, 10-239 10-242, 10-247 to 10-252, 10-255 to 10-258, 10-261 to 10-262, 10-266 to 10-268, 10-270 to 10-272, 10-277 to 10 -278, 10-281 to 10-284, 10-289 to 10-291, 10-295 to 10-301, 10-304 to 10-310, 10-313 to 10-331, 10-334 to 10-341 10-346 to 10-348, 10-350 to 10-353, 10-358 to 10-361, 10-3 6 to 10-371, 10-374 to 10-377, 10-380 to 10-381, 10-385 to 10-387, 10-389 to 10-391, 10-396 to 10-397, 10-400 to 10-403, 10-408 to 10-410, 10-414 to 10-420, 10-423 to 10-429, 10-432 to 10-450, 10-453 to 10-460, 10-465 to 10- 467, 10-469 to 10-472, 10-477 to 10-480, 10-485 to 10-490, 10-493 to 10-496, 10-499 to 10-500, 10-504 to 10-506, 10-508 to 10-510, 10-515 to 10-516, 10-519 to 10-522, 10-527 to 10-529, 10-533 to 10-539, 10-542 to 10-548, 10-551 to 10-569, 10-572 to 10-579, 10-584 to 10-586, 10-588 to 10- 591, 10-596 to 10-599, 10-604 to 10-609, 10-612 to 10-615, 10-618 to 10-619, 10-623 to 10-625, 10-627 to 10-629, 10-634 to 10-635, 10-638 to 10-641, 10-646 to 10-648, 10-652 to 10-658, 10-661 to 10-667, 10-670 to 10-688, 10- 691 to 10-698, 10-703 to 10-705, 10-707 to 10-710, 10-715 to 10- 18, 10-723 to 10-728, 10-731 to 10-734, 10-737 to 10-738, 10-742 to 10-744, 10-746 to 10-748, 10-753 to 10-754, 10-757 to 10-760, 10-765 to 10-767, 10-771 to 10-777, 10-780 to 10-786, 10-789 to 10-807, 10-810 to 10-817, 10- 822 to 10-824, 10-826 to 10-829, 10-834 to 10-839, 10-842 to 10-845, 10-848 to 10-849, 10-853 to 10-855, 10-857 to 10-859, 10-864 to 10-865, 10-867 to 10-882, 10-885 to 10-892 10-897 to 10-899, 10-901 to 10-904, 10-909 to 10-914, 10-917 to 10-920, 10-923 to 10-924, 10-928 to 10-930, 10- 932 to 10-934, 10-939 to 10-940, 10-942 to 10-957, 10-960 to 10-967, 10-972 to 10-974, 10-976 to 10-979, 10-984 to 10-989, 10-992 to 10-995, 10-998 to 10-999, 10-1003 to 10-1005, 10-1007 to 10-1009, 10-1014 to 10-1015, 10-1017 to 10- 1032, 10-1035 to 10-1042, 10-1047 to 10-1049, 10-105 1 to 10-1054, 10-1059 to 10-1064, 10-1067 to 10-1070, 10-1073 to 10-1074, 10-1078 to 10-1080, 10-1082 to 10-1084, 10-1089 to 10-1090, 10-1092 to 10-1107, 10-1110 to 10-1117, 10-1122 to 10-1124, 10-1126 to 10-1129, 10-1134 to 10-1139, 10-1142 to 10- 1145, 10-1148 to 10-1149, 10-1153 to 10-1155, 10-1157 to 10-1159, 10-1164 to 10-1165, 10-1167 to 10-1182, 10-1185 to 10-1192, 10-1197 to 10-1199 10-1201 to 10-1204, 10-1209 to 10-1214, 10-1217 to 10-1220, 10-1223 to 10-1224, 10-1228 to 10-1230, 10-1232 to 10-1234, 10- 1239 to 10-1240, 10-1242 to 10-1257, 10-1260 to 10-1267, 10-1272 to 10-1274, 10-1276 to 10-1279, 10-1284 to 10-1289,
11-1 to 11-4, 11-9 to 11-14, 11-17 to 11-20, 11-23 to 11-24, 11-28 to 11-30, 11-32 to 11-34, 11- 39 to 11-40, 11-43 to 11-46, 11-51 to 11-53, 11-57 to 11-63, 11-66 to 11-72, 11-75 to 11-93, 11-96 to 11-103, 11-108 to 11-110, 11-112 to 11-115, 11-120 to 11-123, 11-128 to 11-133, 11-136 to 11-139, 11-142 to 11- 143, 11-147 to 11-149, 11-151 to 11-153, 11-158 to 11-159, 11-162 to 11-165, 11-170 to 11-172, 1 -176 to 11-182, 11-185 to 11-191, 11-194 to 11-212, 11-215 to 11-222, 11-227 to 11-229, 11-231 to 11-234, 11-239 11-242, 11-247 to 11-252, 11-255 to 11-258, 11-261 to 11-262, 11-266 to 11-268, 11-270 to 11-272, 11-277 to 11 -278, 11-281 to 11-284, 11-289 to 11-291, 11-295 to 11-301, 11-304 to 11-310, 11-313 to 11-331, 11-334 to 11-341 11-346 to 11-348, 11-350 to 11-353, 11-358 to 11-361, 11-3 6 to 11-371, 11-374 to 11-377, 11-380 to 11-381, 11-385 to 11-387, 11-389 to 11-391, 11-396 to 11-397, 11-400 to 11-403, 11-408 to 11-410, 11-414 to 11-420, 11-423 to 11-429, 11-432 to 11-450, 11-453 to 11-460, 11-465 to 11- 467, 11-469 to 11-472, 11-477 to 11-480, 11-485 to 11-490, 11-493 to 11-496, 11-499 to 11-500, 11-504 to 11-506, 11-508 to 11-510, 11-515 to 11-516, 11-519 to 11-522, 11-527 to 11-529, 11-533 to 11-539, 11-542 to 11-548, 11-551 to 11-569, 11-572 to 11-579, 11-584 to 11-586, 11-588 to 11- 591, 11-596 to 11-599, 11-604 to 11-609, 11-612 to 11-615, 11-618 to 11-619, 11-623 to 11-625, 11-627 to 11-629, 11-634 to 11-635, 11-638 to 11-641, 11-646 to 11-648, 11-652 to 11-658, 11-661 to 11-667, 11-670 to 11-688, 11- 691 to 11-698, 11-703 to 11-705, 11-707 to 11-710, 11-715 to 11- 18, 11-723 to 11-728, 11-731 to 11-734, 11-737 to 11-738, 11-742 to 11-744, 11-746 to 11-748, 11-753 to 11-754, 11-757 to 11-760, 11-765 to 11-767, 11-771 to 11-777, 11-780 to 11-786, 11-789 to 11-807, 11-810 to 11-817, 11- 822 to 11-824, 11-826 to 11-829, 11-834 to 11-839, 11-842 to 11-845, 11-848 to 11-849, 11-853 to 11-855, 11-857 to 11-859, 11-864 to 11-865, 11-867 to 11-882, 11-885 to 11-892 11-897 to 11-899, 11-901 to 11-904, 11-909 to 11-914, 11-917 to 11-920, 11-923 to 11-924, 11-928 to 11-930, 11- 932 to 11-934, 11-939 to 11-940, 11-942 to 11-957, 11-960 to 11-967, 11-972 to 11-974, 11-976 to 11-979, 11-984 to 11-989, 11-992 to 11-995, 11-998 to 11-999, 11-1003 to 11-1005, 11-1007 to 11-1009, 11-1014 to 11-1015, 11-1017 to 11- 1032, 11-1035 to 11-1042, 11-1047 to 11-1049, 11-105 1 to 11-1054, 11-1059 to 11-1064, 11-1067 to 11-1070, 11-1073 to 11-1074, 11-1078 to 11-1080, 11-1082 to 11-1084, 11-1089 to 11-1090, 11-1092 to 11-1107, 11-1110 to 11-1117, 11-1122 to 11-1124, 11-1126 to 11-1129, 11-1134 to 11-1139, 11-1142 to 11- 1145, 11-1148 to 11-1149, 11-1153 to 11-1155, 11-1157 to 11-1159, 11-1164 to 11-1165, 11-1167 to 11-1182, 11-1185 to 11-1192, 11-1197 to 11-1199 11-1201 to 11-1204, 11-1209 to 11-1214, 11-1217 to 11-1220, 11-1223 to 11-1224, 11-1228 to 11-1230, 11-1232 to 11-1234, 11- 1239 to 11-1240, 11-1242 to 11-1257, 11-1260 to 11-1267, 11-1272 to 11-1274, 11-1276 to 11-1279, 11-1284 to 11-1289,
14-5, 14-11, 14-16, 14-18, 14-23, 14-29, 14-34 and 14-36,

Further suitable compounds are exemplified compound numbers 1-9 to 1-13, 1-17 to 1-19, 1-23 to 1-24, 1-32 to 1-33, 1-39, 1-51, 1 -60 to 1-62, 1-69 to 1-72, 1-79 to 1-82, 1-85 to 1-86, 1-101 to 1-102, 1-112 to 1-115, 1-128 To 1-132, 1-136 to 1-138, 1-142 to 1-143, 1-151 to 1-152, 1-158, 1-170, 1-179 to 1-181, 1-188 to 1 -191, 1-198 to 1-201, 1-204 to 1-205, 1-220 to 1-221, 1-231 to 1-234, 1-247 to 1-251, 1-255 to 1-257 , 1-261 to 1-262, 1-270 to 1-271 1-277, 1-289, 1-298 to 1-300, 1-307 to 1-310, 1-317 to 1-320, 1-323 to 1-324, 1-339 to 1-340, 1- 350 to 1-353, 1-366 to 1-370, 1-374 to 1-376, 1-380 to 1-381, 1-389 to 1-390, 1-396, 1-408, 1-417 to 1-419, 1-426 to 1-429, 1-436 to 1-439, 1-442 to 1-443, 1-458 to 1-459, 1-469 to 1-472, 1-485 to 1- 489, 1-493 to 1-495, 1-499 to 1-500, 1-508 to 1-509, 1-515, 1-527, 1-536 to 1-538, 1-545 to 1-548, 1-555 to 1-5 8, 1-561 to 1-562, 1-577 to 1-578, 1-588 to 1-591, 1-604 to 1-608, 1-612 to 1-614, 1-618 to 1-619, 1-627 to 1-628, 1-634, 1-646, 1-655 to 1-657, 1-664 to 1-667, 1-674 to 1-677, 1-680 to 1-681, 1- 696 to 1-697, 1-707 to 1-710, 1-723 to 1-727, 1-731 to 1-733, 1-737 to 1-738, 1-746 to 1-747, 1-753, 1-765, 1-774 to 1-776, 1-783 to 1-786, 1-793 to 1-796, 1-799 to 1-800, 1-815 to 1-816, 1-826 to 1- 829, 1-834 to 1 -838, 1-842 to 1-844, 1-848 to 1-849, 1-857 to 1-858, 1-864, 1-868 to 1-871, 1-874 to 1-875, 1-890 1-891, 1-901 to 1-904, 1-909 to 1-913, 1-917 to 1-919, 1-923 to 1-924, 1-932 to 1-933, 1-939, 1 -943 to 1-946, 1-949 to 1-950, 1-965 to 1-966, 1-976 to 1-979, 1-984 to 1-988, 1-992 to 1-994, 1-998 1-999, 1-1007 to 1-1008, 1-1014, 1-1018 to 1-1021, 1-1024 to 1-1025, 1-1040 to 1-1041, 1-1051 to 1-1054, -1059 to 1-1063, 1-1067 to 1-1069, 1-1073 to 1-1074, 1-1082 to 1-1083, 1-1089, 1-1093 to 1-1096, 1-1099 to 1-1100 1-1115 to 1-1116, 1-1126 to 1-1129, 1-1134 to 1-1138, 1-1142 to 1-1144, 1-1148 to 1-1149, 1-1157 to 1-1158, -1164, 1-1168 to 1-1171, 1-1174 to 1-1175, 1-1190 to 1-1191, 1-1201 to 1-1204, 1-1209 to 1-1213, 1-1217 to 1-1219 1-1223 to 1-1224, 1-1232 to 1-1233, 1-1239, 1-1243 to 1-12 6,1-1249 or 1-1250,1-1265 or 1-1266,1-1276 or 1-1279,1-1341,1-1342,1-1346,1-1347,
2-1 to 2-4, 2-11 to 2-14, 2-21 to 2-24, 2-31 to 2-34,
3-48 to 3-50,
7-9 to 7-13, 7-17 to 7-19, 7-23 to 7-24, 7-32 to 7-33, 7-39, 7-51, 7-60 to 7-62, 7- 69 to 7-72, 7-79 to 7-82, 7-85 to 7-86, 7-101 to 7-102, 7-112 to 7-115, 7-128 to 7-132, 7-136 to 7-138, 7-142 to 7-143, 7-151 to 7-152, 7-158, 7-170, 7-179 to 7-181, 7-188 to 7-191, 7-198 to 7- 201, 7-204 to 7-205, 7-220 to 7-221, 7-231 to 7-234, 7-247 to 7-251, 7-255 to 7-257, 7-261 to 7-262, 7-270 to 7-271, 7-277, 7-289, 7-29 To 7-300, 7-307 to 7-310, 7-317 to 7-320, 7-323 to 7-324, 7-339 to 7-340, 7-350 to 7-353, 7-366 to 7 -370, 7-374 to 7-376, 7-380 to 7-381, 7-389 to 7-390, 7-396, 7-408, 7-417 to 7-419, 7-426 to 7-429 7-436 to 7-439, 7-442 to 7-443, 7-458 to 7-459, 7-469 to 7-472, 7-485 to 7-489, 7-493 to 7-495, 7 -499 to 7-500, 7-508 to 7-509, 7-515, 7-527, 7-536 to 7-538, 7-545 to 7-548, 7-555 to 7-558, 7-561 To 7-562, 7 577 to 7-578, 7-588 to 7-591, 7-604 to 7-608, 7-612 to 7-614, 7-618 to 7-619, 7-627 to 7-628, 7-634, 7-646, 7-655 to 7-657, 7-664 to 7-667, 7-674 to 7-677, 7-680 to 7-681, 7-696 to 7-697, 7-707 to 7- 710, 7-723 to 7-727, 7-731 to 7-733, 7-737 to 7-738, 7-746 to 7-747, 7-753, 7-765, 7-774 to 7-776, 7-783 to 7-786, 7-793 to 7-796, 7-799 to 7-800, 7-815 to 7-816, 7-826 to 7-829, 7-834 to 7-838, 7- 842 to 7-844 7-848 to 7-849, 7-857 to 7-858, 7-864, 7-868 to 7-871, 7-874 to 7-875, 7-890 to 7-891, 7-901 to 7 -904, 7-909 to 7-913, 7-917 to 7-919, 7-923 to 7-924, 7-932 to 7-933, 7-939, 7-943 to 7-946, 7-949 To 7-950, 7-965 to 7-966, 7-976 to 7-979, 7-984 to 7-988, 7-992 to 7-994, 7-998 to 7-999, 7-1007 to 7 -1008, 7-1014, 7-1018 to 7-1021, 7-1024 to 7-1025, 7-1040 to 7-1041, 7-1051 to 7-1054, 7-1059 to 7-1063, 7- 067 to 7-1069, 7-1073 to 7-1074, 7-1082 to 7-1083, 7-1089, 7-1093 to 7-1096, 7-1099 to 7-1100, 7-1115 to 7-1116, 7-1126 to 7-1129, 7-1134 to 7-1138, 7-1142 to 7-1144, 7-1148 to 7-1149, 7-1157 to 7-1158, 7-1164, 7-1168 to 7- 1171, 7-1174 to 7-1175, 7-1190 to 7-1191, 7-1201 to 7-1204, 7-1209 to 7-1213, 7-1217 to 7-1219, 7-1223 to 7-1224, 7-1232 to 7-1233, 7-1239, 7-1243 to 7-1246, 7-1249 to 7-1250 7-1265 or 7-1266,7-1276 or 7-1279,
10-9 to 10-13, 10-17 to 10-19, 10-23 to 10-24, 10-32 to 10-33, 10-39, 10-51, 10-60 to 10-62, 10- 69 to 10-72, 10-79 to 10-82, 10-85 to 10-86, 10-101 to 10-102, 10-112 to 10-115, 10-128 to 10-132, 10-136 to 10-138, 10-142 to 10-143, 10-151 to 10-152, 10-158, 10-170, 10-179 to 10-181, 10-188 to 10-191, 10-198 to 10- 201, 10-204 to 10-205, 10-220 to 10-221, 10-231 to 10-234, 10-247 to 10-251, 10-255 to 1 -257, 10-261 to 10-262, 10-270 to 10-271, 10-277, 10-289, 10-298 to 10-300, 10-307 to 10-310, 10-317 to 10-320 10-323 to 10-324, 10-339 to 10-340, 10-350 to 10-353, 10-366 to 10-370, 10-374 to 10-376, 10-380 to 10-381, 10 -389 to 10-390, 10-396, 10-408, 10-417 to 10-419, 10-426 to 10-429, 10-436 to 10-439, 10-442 to 10-443, 10-458 To 10-459, 10-469 to 10-472, 10-485 to 10-489, 10-493 to 10-495 10-499 to 10-500, 10-508 to 10-509, 10-515, 10-527, 10-536 to 10-538, 10-545 to 10-548, 10-555 to 10-558, 10- 561 to 10-562, 10-577 to 10-578, 10-588 to 10-591, 10-604 to 10-608, 10-612 to 10-614, 10-618 to 10-619, 10-627 to 10-628, 10-634, 10-646, 10-655 to 10-657, 10-664 to 10-667, 10-674 to 10-677, 10-680 to 10-681, 10-696 to 10- 697, 10-707 to 10-710, 10-723 to 10-727, 10-731 to 10-733, 10-73 7 to 10-738, 10-746 to 10-747, 10-753, 10-765, 10-774 to 10-776, 10-783 to 10-786, 10-793 to 10-796, 10-799 to 10-800, 10-815 to 10-816, 10-826 to 10-829, 10-834 to 10-838, 10-842 to 10-844, 10-848 to 10-849, 10-857 to 10- 858, 10-864, 10-868 to 10-871, 10-874 to 10-875, 10-890 to 10-891, 10-901 to 10-904, 10-909 to 10-913, 10-917 to 10-919, 10-923 to 10-924, 10-932 to 10-933, 10-939, 10-943 to 10 946, 10-949 to 10-950, 10-965 to 10-966, 10-976 to 10-979, 10-984 to 10-998, 10-992 to 10-994, 10-998 to 10-999, 10-1007 to 10-1008, 10-1014, 10-1018 to 10-1021, 10-1024 to 10-1025, 10-1040 to 10-1041, 10-1051 to 10-1054, 10-1059 to 10- 1063, 10-1067 to 10-1069, 10-1073 to 10-1074, 10-1082 to 10-1083, 10-1089, 10-1093 to 10-1096, 10-1099 to 10-1100, 10-1115 to 10-1116, 10-1126 to 10-1129, 1 -1134 to 10-1138, 10-1142 to 10-1144, 10-1148 to 10-1149, 10-1157 to 10-1158, 10-1164, 10-1168 to 10-1171, 10-1174 to 10-1175 10-1190 to 10-1191, 10-1201 to 10-1204, 10-1209 to 10-1213, 10-1217 to 10-1219, 10-1223 to 10-1224, 10-1232 to 10-1233, 10 -1239, 10-1243 to 10-1246, 10-1249 to 10-1250, 10-1265 to 10-1266, 10-1276 to 10-1279,
11-9 to 11-13, 11-17 to 11-19, 11-23 to 11-24, 11-32 to 11-33, 11-39, 11-51, 11-60 to 11-62, 11- 69 to 11-72, 11-79 to 11-82, 11-85 to 11-86, 11-101 to 11-102, 11-112 to 11-115, 11-128 to 11-132, 11-136 to 11-138, 11-142 to 11-143, 11-151 to 11-152, 11-158, 11-170, 11-179 to 11-181, 11-188 to 11-191, 11-198 to 11- 201, 11-204 to 11-205, 11-220 to 11-221, 11-231 to 11-234, 11-247 to 11-251, 11-255 to 1 -257, 11-261 to 11-262, 11-270 to 11-271, 11-277, 11-289, 11-298 to 11-300, 11-307 to 11-310, 11-317 to 11-320 11-323 through 11-324, 11-339 through 11-340, 11-350 through 11-353, 11-366 through 11-370, 11-374 through 11-376, 11-380 through 11-381, 11 -389 to 11-390, 11-396, 11-408, 11-417 to 11-419, 11-426 to 11-429, 11-436 to 11-439, 11-442 to 11-443, 11-458 Thru 11-459, 11-469 thru 11-472, 11-485 thru 11-489, 11-493 thru 11-495 11-499 to 11-500, 11-508 to 11-509, 11-515, 11-527, 11-536 to 11-538, 11-545 to 11-548, 11-555 to 11-558, 11- 561 to 11-562, 11-577 to 11-578, 11-588 to 11-591, 11-604 to 11-608, 11-612 to 11-614, 11-618 to 11-619, 11-627 to 11-628, 11-634, 11-646, 11-655 to 11-657, 11-664 to 11-667, 11-674 to 11-677, 11-680 to 11-681, 11-696 to 11- 697, 11-707 to 11-710, 11-723 to 11-727, 11-731 to 11-733, 11-73 7 to 11-738, 11-746 to 11-747, 11-753, 11-765, 11-774 to 11-776, 11-783 to 11-786, 11-793 to 11-796, 11-799 to 11-800, 11-815 to 11-816, 11-826 to 11-829, 11-834 to 11-838, 11-842 to 11-844, 11-848 to 11-849, 11-857 to 11- 858, 11-864, 11-868 to 11-871, 11-874 to 11-875, 11-890 to 11-891, 11-901 to 11-904, 11-909 to 11-913, 11-917 to 11-919, 11-923 to 11-924, 11-932 to 11-933, 11-939, 11-943 to 11 946, 11-949 to 11-950, 11-965 to 11-966, 11-976 to 11-979, 11-984 to 11-988, 11-992 to 11-994, 11-998 to 11-999, 11-1007 to 11-1008, 11-1014, 11-1018 to 11-1021, 11-1024 to 11-1025, 11-1040 to 11-1041, 11-1051 to 11-1054, 11-1059 to 11- 1063, 11-1067 to 11-1069, 11-1073 to 11-1074, 11-1082 to 11-1083, 11-1089, 11-1093 to 11-1096, 11-1099 to 11-1100, 11-1115 to 11-1116, 11-1126 to 11-1129, 1 -1134 to 11-1138, 11-1142 to 11-1144, 11-1148 to 11-1149, 11-1157 to 11-1158, 11-1164, 11-1168 to 11-1171, 11-1174 to 11-1175 , 11-1190 to 11-1191, 11-1201 to 11-1204, 11-1209 to 11-1213, 11-1217 to 11-1219, 11-1223 to 11-1224, 11-1232 to 11-1233, 11 -11239, 11-1243 to 11-1246, 11-1249 to 11-1250, 11-1265 to 11-1266, and 11-1276 to 11-1279,
Further preferred compounds are Exemplified Compound Nos. 1-11 to 1-13, 1-19, 1-32, 1-60, 1-69, 1-79, 1-130 to 1-132, 1-138, 1-151, 1-179, 1-188, 1-198, 1-249 to 1-251, 1-257, 1-270, 1-298, 1-307, 1-317, 1-368 to 1- 370, 1-376, 1-389, 1-417, 1-426, 1-436, 1-487 to 1-489, 1-495, 1-508, 1-536, 1-545, 1-555, 1-606 to 1-608, 1-614, 1-627, 1-655, 1-664, 1-674, 1-725 to 1-727, 1-733, 1-746, 1-774, 1- 783, 1-793, 1-836 to 1-838, 1-844, 1 857, 1-868, 1-911 to 1-913, 1-919, 1-932, 1-943, 1-986 to 1-988, 1-994, 1-1007, 1-1018, 1-1061 to 1-1063, 1-1069, 1-1082, 1-1093, 1-1136 to 1-1138, 1-1144, 1-1157, 1-1168, 1121-211 to 1-1213, 1-1219, 1- 1232, 1-1243, 1-11341, 1-1342, 1-1346, 1-1347,
7-11 to 7-13, 7-19, 7-32, 7-60, 7-69, 7-79, 7-130 to 7-132, 7-138, 7-151, 7-179, 7- 188, 7-198, 7-249 to 7-251, 7-257, 7-270, 7-298, 7-307, 7-317, 7-368 to 7-370, 7-376, 7-389, 7-417, 7-426, 7-436, 7-487 to 7-487, 7-495, 7-508, 7-536, 7-545, 7-555, 7-606 to 7-608, 7- 614, 7-627, 7-655, 7-664, 7-674, 7-725 to 7-727, 7-733, 7-746, 7-774, 7-783, 7-793, 7-836 to 7-838, 7-844, 7-857, 7-868, 7-911 to 7 913, 7-919, 7-932, 7-943, 7-986 to 7-988, 7-994, 7-1007, 7-1018, 7-1061 to 7-1063, 7-1069, 7-1082, 7-1093, 7-1136 to 7-1138, 7-1144, 7-1157, 7-1168, 7-1211 to 7-1213, 7-1219, 7-1232, 7-1243,
10-11 to 10-13, 10-19, 10-32, 10-60, 10-69, 10-79, 10-130 to 10-132, 10-138, 10-151, 10-179, 10- 188, 10-198, 10-249 to 10-251, 10-257, 10-270, 10-298, 10-307, 10-317, 10-368 to 10-370, 10-376, 10-389, 10-417, 10-426, 10-436, 10-487 to 10-489, 10-495, 10-508, 10-536, 10-545, 10-555, 10-606 to 10-608, 10- 614, 10-627, 10-655, 10-664, 10-674, 10-725 to 10-727, 10-733, 10-746, 10-774, 10-7 3, 10-793, 10-836 to 10-838, 10-844, 10-857, 10-868, 10-911 to 10-913, 10-919, 10-932, 10-943, 10-986 to 10-988, 10-994, 10-1007, 10-1018, 10-1061 to 10-1063, 10-1069, 10-1082, 10-1093, 10-1136 to 10-1138, 10-1144, 10- 1157, 10-1168, 10-1211 to 10-1213, 10-1219, 10-1232, 10-1243,
11-11 to 11-13, 11-19, 11-32, 11-60, 11-69, 11-79, 11-130 to 11-132, 11-138, 11-151, 11-179, 11- 188, 11-198, 11-249 to 11-251, 11-257, 11-270, 11-298, 11-307, 11-317, 11-368 to 11-370, 11-376, 11-389, 11-417, 11-426, 11-436, 11-487 to 11-487, 11-495, 11-508, 11-536, 11-545, 11-555, 11-606 to 11-608, 11- 614, 11-627, 11-655, 11-664, 11-674, 11-725 to 11-727, 11-733, 11-746, 11-774, 11-7 3, 11-793, 11-836 to 11-838, 11-844, 11-857, 11-868, 11-911 to 11-913, 11-919, 11-932, 11-943, 11-986 to 11-988, 11-994, 11-1007, 11-1018, 11-1061 to 11-1063, 11-1069, 11-1082, 11-1093, 11-1136 to 11-1138, 11-1144, 11- 1157, 11-1168, 11-1211 to 11-1213, 11-1219, 11-1232, and 11-1243.

Particularly suitable compounds are, for example,
Exemplified compound number 1-366: 4- [1- (4-carbamoylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4 -Yl) -1H-pyrrole,
Exemplified Compound No. 1-367: 2- (4-Fluorophenyl) -4- [1- [4- (N-methylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3 -(Pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-368: 4- [1- [4- (N-ethylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3 -(Pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-369: 2- (4-Fluorophenyl) -4- [1- [4- (N-propylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3 -(Pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-370: 2- (4-Fluorophenyl) -4- [1- [4- (N-isopropylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3 -(Pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-374: 4- [1- [4- (N-cyclopropylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl)- 3- (pyridin-4-yl) -1H-pyrrole,
Exemplified compound number 1-376: 4- [1- [4- (N-cyclopentylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3 -(Pyridin-4-yl) -1H-pyrrole,
Exemplary compound number 1-389: 4- [1- [4- [N- (2-fluoroethyl) carbamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4- Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified compound number 1-396: 4- [1- [4- [N- (ethoxycarbonylmethyl) carbamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluoro Phenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Illustrative compound number 1-417: 2- (4-fluorophenyl) -4- [1- (4-methanesulfinylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine- 4-yl) -1H-pyrrole,
Exemplified Compound No. 1-426: 2- (4-Fluorophenyl) -4- [1- (4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine- 4-yl) -1H-pyrrole,
Exemplified Compound No. 1-436: 2- (4-Fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-437: 4- [1- [4- (N-ethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-438: 2- (4-Fluorophenyl) -4- [1- [4- (N-propylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplary compound number 1-439: 2- (4-fluorophenyl) -4- [1- [4- (N-isopropylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-442: 4- [1- [4- (N, N-dimethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluoro Phenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-443: 4- [1- [4- (N-cyclopropylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) ) -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified compound number 1-458: 4- [1- [4- [N- (2-fluoroethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4- Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified compound number 1-459: 2- (4-fluorophenyl) -4- [1- [4- [N- (2-methoxyethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridine-4 -Yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified compound number 1-470: 4- [1- [4- (N-ethoxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Illustrative compound number 1-472: 4- [1- [4- (N-allyloxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) ) -3- (pyridin-4-yl) -1H-pyrrole,
Illustrative compound number 1-527: 4- [1- (4-acetylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (3-chloro-4-fluorophenyl) -3- (Pyridin-4-yl) -1H-pyrrole,
Illustrative compound number 1-536: 2- (3-chloro-4-fluorophenyl) -4- [1- (4-methanesulfinylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3 -(Pyridin-4-yl) -1H-pyrrole,
Illustrative compound number 1-545: 2- (3-chloro-4-fluorophenyl) -4- [1- (4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3 -(Pyridin-4-yl) -1H-pyrrole,
Illustrative compound number 1-555: 2- (3-chloro-4-fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridine- 4-yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified compound number 1-11341: 2- (4-fluorophenyl) -4- [1- [4- (2-methoxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl]- 3- (pyridin-4-yl) -1H-pyrrole,
Exemplified compound number 1-1342: 2- (4-fluorophenyl) -4- [1- [4- (2-hydroxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl]- 3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-1346: 2- (3-Chloro-4-fluorophenyl) -4- [1- [4- (2-methoxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridine-4 -Yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 1-1347: 2- (3-Chloro-4-fluorophenyl) -4- [1- [4- (2-hydroxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridine-4 -Yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 7-366: 4-[(2S, 8aS) -2- (4-carbamoylphenyl) -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- ( 4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 7-367: 2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-methylcarbamoyl) phenyl] -1,2,3,5,6,8a -Hexahydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 7-368: 4-[(2S, 8aS) -2- [4- (N-ethylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl ] -2- (4-Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Illustrative compound number 7-369: 2- (4-fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-propylcarbamoyl) phenyl] -1,2,3,5,6,8a -Hexahydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplary Compound No. 7-370: 2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-isopropylcarbamoyl) phenyl] -1,2,3,5,6,8a -Hexahydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 7-372: 4-[(2S, 8aS) -2- [4- (N-benzylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl ] -2- (4-Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 7-374: 4-[(2S, 8aS) -2- [4- (N-cyclopropylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7- Yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified Compound No. 7-389: 4-[(2S, 8aS) -2- [4- [N- (2-fluoroethyl) carbamoyl] phenyl] -1,2,3,5,6,8a-hexahydroindo Lysine-7-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified compound number 7-390: 2- (4-fluorophenyl) -4-[(2S, 8aS) -2- [4- [N- (2-methoxyethyl) carbamoyl] phenyl] -1,2,3 5,6,8a-Hexahydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole,
Exemplified compound number 7-486: 2- (3-chloro-4-fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-methylcarbamoyl) phenyl] -1,2,3,5 , 6,8a-Hexahydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole and Exemplified Compound No. 10-366: 3- [1- (4-carbamoylphenethyl) -1, 2,3,6-tetrahydropyridin-4-yl] -5- (4-fluorophenyl) -4- (pyridin-4-yl) -1H-pyrazole.

  The compound having the general formula (I) can be easily produced according to the following methods A to H.

Method A is a method for producing a compound having R ³ bonded to a carbon atom on ring A among the compounds having general formula (I).

In the above formula, A, R ¹ and R ² are as defined above,
The cyclic group Hy represents a group in which the bond including a dotted line in the general formula (IIa) or (IIb) is a single bond,
The cyclic group Hy ′ represents a group in which the bond including a dotted line in the general formula (IIa) or (IIb) is a double bond.

  The first step is a step of brominating the cyclic compound (1) using a brominating agent (for example, N-bromosuccinimide etc.) to produce the bromo cyclic compound (2), and the second step is In this step, the bromocyclic compound (2) is lithiated and then reacted with the heterocyclyl ketone (3) to produce the compound (Ia) of the present invention. The first step and the second step can be performed according to the method described in detail in Brian L. Bray et al., J. Org. Chem., Vol. 55, 6317-6318 (1990).

  Compound (Ia) is the same as described in L. Revesz et al., Bioorg. Med. Chem. Lett., Vol. 10, 1261-1264 (2000). It can also be produced by direct lithiation by a method and reacting the resulting compound with a heterocyclyl ketone (3).

  The third step is a step for producing the compound (Ib) of the present invention by subjecting the compound (Ia) of the present invention to a dehydration reaction. This dehydration reaction is usually performed in the presence of an acid catalyst such as sulfuric acid, a solid catalyst such as alumina, or a halogenating agent such as thionyl chloride. [These reactions are described in, for example, GHColeman & HFJohnstone, Org. Synth. , I, 183 (1941), RLSawyer & DW Andrus, Org. Synth., III, 276 (1955), and JSLomas et al., Tetrahedron Lett., 599 (1971). ]. In addition, the dehydration reaction in this step is performed using a trialkylsilane such as triethylsilane, tripropylsilane, or tributylsilane, and trifluoroacetic acid [for example, Francis A. Carey & Henry S. Tremper, J. Am. Chem. .Soc., Vol.91, 2967-2972 (1969)].

  The fourth step is a step of producing the compound (Ic) of the present invention by reducing the double bond of the compound (Ib) of the present invention. For example, SMKerwin et al., J. Org. Chem., Vol. 52, 1686 (1987), T. Hudlicky et al., J. Org. Chem., Vol. 52, 4641 (1987), and the like.

  In the method A, when synthesizing a compound in which A is pyrrole which may be substituted with a group selected from two substituent groups δ, the nitrogen atom at the 1-position of pyrrole was protected in advance. It is desirable to synthesize such compounds by subjecting the compounds to a first step, deprotection after the second or third step and, if desired, introducing a substituent group δ to the nitrogen atom.

  Protection of the nitrogen atom at the 1-position of pyrrole is, for example, by dissolving a pyrrole compound corresponding to compound (1) in 300 ml of tetrahydrofuran, and cooling (eg, 0 ° C. or lower) with butyl lithium or sodium hydride and triisopropylsilyl triflate Alternatively, it can be carried out by adding (t-butyl) diphenylsilyl chloride and stirring at room temperature. The deprotection reaction is usually carried out in a solvent in the presence of a base, for example, by adding an aqueous sodium hydroxide solution, saturated aqueous sodium hydrogen carbonate solution or tetrabutylammonium fluoride to the protected compound. it can.

  Introduction of the substituent group δ at the 1-position of pyrrole can be achieved, for example, by carrying out a reaction similar to the following <Method B>.

<Method B>
The method B is a method for producing a compound in which the cyclic group A is pyrrole, pyrazole or imidazole, and R ³ is bonded to the nitrogen atom.

In the above formula, R ¹ , R ² and R ³ are as defined above,
The cyclic group A ′ may be substituted with a group selected from two substituent groups δ in the definition of A and selected from pyrrole and one substituent group δ. Represents imidazole optionally substituted with pyrazole or a group selected from one substituent group δ,
L represents a leaving group.

  The “leaving group” in the definition of L usually indicates a group leaving as a nucleophilic residue, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; methanesulfonyloxy, ethane Lower alkanesulfonyloxy group such as sulfonyloxy; Halogeno lower alkanesulfonyloxy group such as trifluoromethanesulfonyloxy, pentafluoroethanesulfonyloxy; Ali such as benzenesulfonyloxy, p-toluenesulfonyloxy, p-nitrobenzenesulfonyloxy -Lulsulfonyloxy group can be mentioned. Preferable is a halogen atom, and particularly preferable is a bromine atom.

  The fifth step is a step for producing the compound (Id) of the present invention by reacting the compound (4) with the heterocyclyl compound (5). This reaction is usually performed in a solvent in the presence or absence of a base.

  Examples of the solvent used include alcohols such as methanol, ethanol, propanol, and isopropanol; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane; aprotic groups such as dimethylformamide, dimethylacetamide, and dimethylsulfoxide. Polar solvents; nitriles such as acetonitrile; esters such as methyl acetate and ethyl acetate; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane and heptane Preferably, ethers, alcohols or aprotic polar solvents are used, and tetrahydrofuran, methanol, ethanol or dimethylformamide is more preferably used.

  Examples of the base used include alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide; alkali metal hydrides such as sodium hydride and lithium hydride; sodium hydroxide, water Alkali metal hydroxides such as potassium oxide; alkali metal carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate; triethylamine, tributylamine, pyridine, picoline, 1,8-diazabicyclo [5.4 .0] -7-undecene, preferably alkali metal carbonates or amines, more preferably triethylamine, pyridine, 1,8-diazabicyclo [5.4.0]- 7-Undecene, sodium carbonate, potassium carbonate, hydrogen carbonate Potassium thorium or bicarbonate is used.

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

When ring A is pyrazole or imidazole and the nitrogen atom is substituted with a substituent (a group other than a hydrogen atom in the definition of R ¹ , R ² , R ^4, or R ⁴ ′), the above <Method B> By carrying out the reaction in the same manner, a desired substituent can be introduced.

<Method C>
The method C is another method for producing a compound in which the cyclic group A ′ is imidazole in the general formula (Id).

In the above formula, R ¹ , R ² and R ³ are as defined above.

The sixth step is a step of producing an imine compound (8) by dehydrating and condensing the amino compound (6) and the aldehyde compound (7),
The seventh step is a step for producing the compound (Ie) of the present invention by reacting the imine compound (8) with the isocyanide compound (9).

  The sixth step and the seventh step are, for example, WO 97/23479, WO 97/25046, WO 97/25047, WO 97/25048, WO 95/02591, JLAdams et al., Bioorg. Med. Chem. Lett. , vol.8, 3111-3116 (1998) and the like.

Among the compounds (I) of the present invention, the compound (If) in which R ² is a heteroaryl group having at least one nitrogen atom substituted with NR ^d R ^e is produced by the following <Method D>. You can also

In the above formula, A, R ¹ , R ³ , R ^d and R ^e are as defined above,
L ′ represents a leaving group,
The group —R ^{2 ′} -L ′ has a leaving group (group L ′), “heteroaryl group having at least one nitrogen atom” (for example, 2-methanesulfonylpyrimidin-4-yl, 2-methanesulfonyl The “heteroaryl group having at least one nitrogen atom” is the same group as the “heteroaryl group having at least one nitrogen atom” in the definition of R ² .

  The leaving group in the definition of L ′ is the same group as the leaving group in the definition of L; a lower alkylsulfonyl group such as methanesulfonyl, ethanesulfonyl, propanesulfonyl, butanesulfonyl; or benzenesulfonyl, p-toluenesulfonyl , An arylsulfonyl group such as p-nitrobenzenesulfonyl, preferably a lower alkylsulfonyl group, and more preferably a methanesulfonyl group.

The eighth step is a step for producing the compound (If) of the present invention by reacting the compound (10) with the amine compound (11) to convert the leaving group into NR ^d R ^e . This reaction is carried out in the same manner as in the fifth step.

Among the compounds (I) of the present invention, the compound (Ig) in which R ³ is a group having the general formula (IIa) can also be produced by the following <Method E>.

In the above formula, A, L, m, R ¹ , R ² , R ⁷ , X and Y are as defined above, and G is a group having the formula Z (R ⁵ ) (R ⁶ ) _n (formula Wherein R ⁵ , R ⁶ , n and Z are as defined above.

  The ninth step is a step for producing the compound (Ig) of the present invention by reacting the compound (12) with the compound (13), and is performed in the same manner as in the <Method B> fifth step.

  Compound (Ig) of the present invention can also be produced by <Method F>.

In the above formula, A, G, m, R ¹ , R ² , R ⁷ , X and Y are as defined above, R ⁹ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, X ′ represents a single bond or a linear or branched alkylene group having 1 to 4 carbon atoms.

  The tenth step is a step for producing the compound (Ig) of the present invention by reacting the compound (12) with the oxo compound (14). This reaction is well known as reductive amination and is carried out according to the method detailed in C.F. Lane, Synthesis, 1975, 135 (1975).

Among the compounds (I) of the present invention, compounds (Ih) to (In) wherein R ⁵ is a carboxy group, a lower alkoxycarbonyl group, an aralkyloxycarbonyl group, an aryloxycarbonyl group or a group having the formula CONR ^a R ^b Can also be produced by the following <Method G>.

In the above formula, A, Hy, Hy ′, R ¹ , R ² , R ^a , R ^b and Z are as defined above, and R ¹⁰ represents a lower alkyl group, an aralkyl group or an aryl group.

  The eleventh step is a step of producing the compound (Ih) of the present invention by lithiation of the bromocyclic compound (2) and then reacting with the heterocyclyl ketone (15). <Method A> Second step It is carried out in the same way.

  The twelfth step is a step for producing the compound (Ii) of the present invention by subjecting the compound (Ih) of the present invention to a dehydration reaction, and is performed in the same manner as in the <Method A> third step.

  The thirteenth step is a step for producing the compound (Ij) of the present invention by reducing the double bond of the compound (Ii) of the present invention, and is carried out in the same manner as in the <Method A> fourth step.

  The 14th step is a step for producing the compound (Ik) of the present invention by hydrolyzing the ester moiety of the compound (Ii) of the present invention. This hydrolysis reaction is performed using an acid or a base and applying reaction conditions commonly used in ordinary organic synthetic chemistry.

  The fifteenth step is a step for producing the compound (Il) of the present invention by reducing the double bond of the compound (Ik) of the present invention, and is carried out in the same manner as in the <Method A> fourth step.

  The sixteenth and seventeenth steps are steps for producing the compound of the present invention (Im or In: carboxylic acid amide) by reacting the compound of the present invention (Ik or Il: carboxylic acid) with the amine compound (16). is there.

  Solvents used include aliphatic hydrocarbons such as pentane, hexane and heptane; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and dichloroethane. Ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, s-butanol, isobutanol, t-butanol; N, N-dimethylformamide, List aprotic polar solvents such as N, N-dimethylacetamide and dimethyl sulfoxide; nitriles such as acetonitrile; esters such as methyl acetate and ethyl acetate; water; It can be. Of these, halogenated hydrocarbons, ethers or esters are preferably used, and dichloromethane, tetrahydrofuran or ethyl acetate is more preferably used.

  Examples of the condensing agent include dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, or N, N′-carbonyldiimidazole.

  Examples of the base to be used include alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and lithium hydride; sodium hydroxide, water Alkali metal hydroxides such as potassium oxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; triethylamine, tributylamine, pyridine, picoline, 1,8-diazabicyclo [5.4.0] -7-undecene Such amines can be mentioned. Of these, amines are preferably used, and triethylamine, pyridine, or 1,8-diazabicyclo [5.4.0] -7-undecene is more preferably used.

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

  The reaction can also be carried out after converting compound (Ik) or (Il) into a reactive derivative.

  When a reactive derivative is used, the “reactive derivative” means an acid halide, mixed acid anhydride, active ester, active amide, etc., and the reaction is carried out in a solvent in the presence of a condensing agent, in the presence of a base or Performed in the absence.

  “Acid halide” can be obtained by reacting compound (Ik) or (Il) with a halogenating agent (eg, thionyl chloride, oxalyl chloride, etc.); Ik) or (Il) and an acid halide (for example, methyl chlorocarbonate, ethyl chlorocarbonate, etc.); the “active ester” is compound (Ik) or (Il) and a hydroxy compound (Eg, N-hydroxysuccinimide, N-hydroxyphthalimide, etc.) in the presence of the “condensation agent” described above; “active amide” (eg, Weinreb amide) is Compound (Ik) or (Il) and N-lower alkoxy-N-lower alkylhydroxylamine (for example, N-methoxy-N- Methylhydroxylamine and the like) in the presence of the aforementioned “condensing agent”. Both are carried out by applying reaction conditions widely used in ordinary organic synthetic chemistry.

  As the solvent, the condensing agent and the base, the above-mentioned solvents, condensing agents and bases can be used.

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

  The hydrolysis from compound (Ij) to compound (Il) can be carried out in the same manner as in the 14th step, and the reduction from compound (Im) to compound (In) is the same as in the 13th or 15th step. Can be implemented.

Among the compounds (I) of the present invention, the compound (Io) and the compound (Ip) in which R ⁵ is a group having the formula S (O) _q R ^c (q represents 1 to 2) are as follows: It can also be manufactured by <Method H>.

In the above formula, A, Hy, Hy ′, R ¹ , R ² , R ^c and Z are as defined above, and q is 1 to 2.

  The 18th step is a step of producing the compound (18) by lithiation of the bromocyclic compound (2) and then reacting with the heterocyclyl ketone (17). <Method A> In the same manner as the 2nd step. To be implemented.

  The 19th step is a step of subjecting the compound (18) to a dehydration reaction to produce the compound (19), and is carried out in the same manner as in the <Method A> 3rd step.

  The 20th step is a step of producing the compound (20) by reducing the double bond of the compound (19), and is carried out in the same manner as in the <Method A> 4th step.

  The 21st step and the 22nd step are steps for producing the compound (Io) or the compound (Ip) of the present invention by oxidizing the sulfide moiety of the compound (19) and the compound (20).

  This oxidation reaction is carried out by using an inert solvent (for example, aliphatic hydrocarbons such as hexane, heptane and petroleum ether; aromatic hydrocarbons such as benzene, toluene and xylene; dichloromethane, chloroform , Halogenated hydrocarbons such as carbon tetrachloride and dichloroethane; alcohols such as methanol, ethanol, propanol and butanol; esters such as ethyl acetate, propyl acetate, butyl acetate and ethyl propionate; acetic acid and propionic acid Water; or a mixed solvent thereof, preferably halogenated hydrocarbons or carboxylic acids, particularly preferably dichloromethane, chloroform, dichloroethane or acetic acid.) Medium, oxidizing agent (for example, peracetic acid, perbenzoate Acid, peracids such as m-chloroperbenzoic acid; hydrogen peroxide; alkali metal perhalogenates such as sodium metaperchlorate, sodium metaperiodate, potassium metaperiodate, Preferred are peracids or hydrogen peroxide, and particularly preferred is m-chloroperbenzoic acid.) And a sulfide compound are -20 ° C to 150 ° C (preferably 0 ° C to 100 ° C). And 10 minutes to 10 hours (preferably 30 minutes to 5 hours).

  In the case of producing a compound in which q is 1 by adding one oxygen atom by the oxidation reaction, 0.6 to 1.4 equivalents (preferably 0.8 to 1 equivalent of the substrate). To 1.2 equivalents) of oxidizing agent is used. In addition, by using the sulfide compound as a substrate and performing the above oxidation reaction using 1.5 to 3 equivalents (preferably 1.8 to 2.5 equivalents) of an oxidizing agent with respect to 1 equivalent of the substrate, A compound in which q is 2 can be produced.

  Compounds used as starting materials in the above methods A to H, that is, compounds (1), (3), (4), (5), (6), (7), (9), (11), (12 ), (13), (14), (15), (16) and (17) are known compounds per se or can be easily treated from known compounds according to known methods. Compound (10) is a compound obtained and can be easily synthesized from a known compound by carrying out reactions similar to those of Method A to Method H.

For example, for compound (1):
A compound in which A is “benzene optionally substituted with a substituent group δ” is described in DJPPinto et al., Bioorg. Med. Chem. Lett., Vol.6, 2907-2912 (1996), DJPPinto et al. , Bioorg. Med. Chem. Lett., Vol. 9, 919-924 (1999), MBNorton et al., J. Med. Chem., Vol. 39, 1846-1856 (1996), WO 96/10012, WO Can be synthesized according to 96/26921 and WO 96/16934,
A compound in which A is “pyridine optionally substituted with substituent group δ” is synthesized according to RWFriesen et al., Bioorg. Med. Chem. Lett., Vol.8, 2777-2782 (1998), etc. Can
A compound in which A is “pyridazine optionally substituted with substituent group δ” or “pyrimidine optionally substituted with substituent group δ” can be synthesized according to WO 00/31065 and the like,
A compound in which A is “pyrrole optionally substituted with substituent group δ” can be synthesized according to EP1070711 and the like,
A compound in which A is “furan optionally substituted with substituent group δ” can be synthesized according to USP 6,048,880, etc.
The compound in which A is “thiophene optionally substituted with substituent group δ” is described in WO 94/26731, Y. Leblanc et al., Bioorg. Med. Chem. Lett., Vol. 5, 2123-2128 ( 1995), SRBertenshaw et al., Bioorg. Med. Chem. Lett., Vol. 5, 2919-2922 (1995), DJPPinto et al., Bioorg. Med. Chem. Lett., Vol. 6, 2907-2912 ( 1996) and WO 95/00501, etc.
A compound in which A is “pyrazole optionally substituted with substituent group δ” can be synthesized according to WO 00/31063, WO 99/58523, WO 00/39116, WO 95/31451, etc.
A compound in which A is “imidazole optionally substituted with substituent group δ” is IKKhanna et al., J. Med. Chem., Vol. 40, 1634-1647 (1997), WO 93/14081, WO 97/23479, USP 5,716,955, WO 97/25046, WO 97/25047, WO 97/25048, WO 95/02591 and JLAdams et al., Bioorg. Med. Chem. Lett., Vol. 8, 3111-3116 ( 1998) etc.
A compound in which A is “isoxazole” can be synthesized according to JP-A-2000-86657,
A compound in which A is “isothiazole” can be synthesized according to WO 95/00501 and the like.

Also for compound (3):
When the cyclic group Hy represents a group in which the bond including the dotted line in the general formula (IIa) is a single bond, it can be produced by the <Method I> shown below.

In the above formula, G, L, m, R ⁷ , X and Y are as defined above.

  The 23rd step is a step of producing the compound (22) by reacting the compound (21) with the compound (13), and is carried out in the same manner as in the <Method B> 5th step.

  The compound (21) used as a starting material is known or can be easily synthesized from a known compound according to a conventional method.

  When the cyclic group Hy represents a group in which the bond including the dotted line in the general formula (IIb) is a single bond, it can be synthesized according to the following <Method J> to <Method P>.

In the above formula, B, L, m and R ⁷ are as defined above,
R ¹¹ and R ¹² are the same or different and represent the “lower alkyl group” or the “aralkyl group”. However, in the compounds (28) and (29), at least three of the six R ⁷ represent hydrogen atoms.

  The 24th step is a step of producing a cyclic amine diester compound (25) by reacting the cyclic amino acid ester compound (24) with the carboxylic acid ester compound (23) having a leaving group (L).

  This reaction is usually performed in a solvent in the presence or absence of a base.

  Examples of the solvent used include alcohols such as methanol, ethanol, propanol, and isopropanol; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane; aprotic groups such as dimethylformamide, dimethylacetamide, and dimethylsulfoxide. Polar solvents; nitriles such as acetonitrile; esters such as methyl acetate and ethyl acetate; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane and heptane Can be mentioned.

  Examples of the base to be used include alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and lithium hydride; sodium hydroxide, water Alkali metal hydroxides such as potassium oxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; triethylamine, tributylamine, pyridine, picoline, 1,8-diazabicyclo [5.4.0] -7-undecene Such amines can be mentioned.

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

  Next, the cyclic amine diester compound (25) is subjected to a Dieckmann reaction (step 25) to form a ketoester compound [compound (26) and / or compound (27)], and then each compound is hydrolyzed and decarboxylated. The reaction is carried out to produce the desired cyclic aminoketone compounds [compound (28) and compound (29)] (steps 26 and 27).

  The reaction employed in the 25th to 27th steps is carried out according to the method described in JRHarrison et al., J. Chem. Soc ,, Perkin Trans. 1, 1999, 3623-3631 (1999). The twenty-sixth step and the twenty-seventh step are performed as follows, for example.

  The reactions in the 26th and 27th steps are usually carried out in the presence or absence of a solvent and in the presence or absence of an acid or a base.

  Examples of the solvent include water or water and an organic solvent (for example, aliphatic hydrocarbons such as pentane, hexane, and heptane; aromatic hydrocarbons such as benzene, toluene, and xylene; dichloromethane, chloroform, carbon tetrachloride, Halogenated hydrocarbons such as dichloroethane; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, s-butanol, isobutanol and t-butanol; Aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and dimethyl sulfoxide; nitriles such as acetonitrile; esters such as methyl acetate and ethyl acetate) It is possible. Preferably, water or a mixed solvent of water and alcohols or ethers is used.

The acid to be used is not particularly limited as long as it is used as an acid in a normal hydrolysis reaction. For example, mineral acids such as hydrochloric acid, sulfuric acid, phosphoric acid; formic acid, acetic acid, propionic acid, trifluoroacetic acid Examples thereof include carboxylic acids such as methanesulfonic acid and ethanesulfonic acid. Of these, mineral acids or carboxylic acids are preferably used, and hydrochloric acid, sulfuric acid, formic acid or acetic acid is more preferably used.
The progress of this reaction is promoted by adding an acid.

  The base to be used is not particularly limited as long as it is used as a base in a normal hydrolysis reaction. For example, alkali metal hydrides such as sodium hydride and lithium hydride; sodium hydroxide and potassium hydroxide Alkali metal hydroxides such as sodium carbonate and potassium carbonate; triethylamine, tributylamine, pyridine, picoline, 1,8-diazabicyclo [5.4.0] -7-undecene and the like Mention may be made of amines. Of these, alkali metal hydroxides are preferably used, and sodium hydroxide or potassium hydroxide is more preferably used.

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

In the above formula, B, G and R ⁷ are as defined above,
R ¹³ represents an amino-protecting group,
Hal represents a halogen atom (preferably a chlorine atom, a bromine atom or an iodine atom),
Y represents a halogenocarbonyl group (for example, —CO—Cl, —CO—Br or —CO—I), an N-lower alkoxy-N-lower alkylcarbamoyl group (for example, N-methoxy-N-methylcarbamoyl, N— Ethoxy-N-methylcarbamoyl, N-ethyl-N-methoxycarbamoyl, etc.) or a cyano group.

However, at least 3 out of 6 R ^{7 in} the compound (34) represent a hydrogen atom.

The “amino-protecting group” in the definition of R ¹³ means an amino-protecting group usually used in organic synthesis. Examples of such a group include 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, hexa Decanoyl, 1-methylpentadecanoyl, 14-methylpentadecanoyl, 13,13-dimethyltetradecanoyl, heptadecanoyl, 15-methylhexadecanoyl, octadecanoyl, 1-methylheptadecanoyl, no Alkanoyl groups such as decanoyl, icosanoyl and henaicosanoyl, halogenated alkylcarbonyl groups such as chloroacetyl, dichloroacetyl, trichloroacetyl and trifluoroacetyl, lower alkoxyalkylcarbonyl groups such as methoxyacetyl, acryloyl, propioroyl, methacryloyl and crotonoyl , An “aliphatic acyl group” such as an unsaturated alkylcarbonyl group such as isocrotonoyl and (E) -2-methyl-2-butenoyl (preferably a lower aliphatic acyl group having 1 to 6 carbon atoms). ); Arylcarbonyl groups such as benzoyl, α-naphthoyl, β-naphthoyl, halogenated arylcarbonyl groups such as 2-bromobenzoyl, 4-chlorobenzoyl, 2,4,6-trifluorobenzoyl, 2, 4 6-trimethylbenzoyl, lower alkylated aryl carbonyl groups such as 4-toluoyl, lower alkoxylated aryl carbonyl groups such as 4-anisoyl, nitrated ants such as 4-nitrobenzoyl, 2-nitrobenzoyl An “aromatic acyl group” such as an arylcarbonyl group, a lower alkoxycarbonylated arylcarbonyl group such as 2- (methoxycarbonyl) benzoyl, an arylated arylcarbonyl group such as 4-phenylbenzoyl; Tri-lower alkylsilyl groups such as trimethylsilyl, triethylsilyl, isopropyldimethylsilyl, t-butyldimethylsilyl, methyldiisopropylsilyl, methyldi-t-butylsilyl, triisopropylsilyl, diphenylmethylsilyl, diphenylbutylsilyl, diphenyliso “Silyl group” such as tri-lower alkylsilyl group substituted with 1 to 2 aryl groups such as propylsilyl, phenyldiisopropylsilyl; the “aralkyl group”, the “alkoxycarbonyl group”, the “alkenyloxy” Examples thereof include a “carbonyl group” and the “aralkyloxycarbonyl group”.

  The 28th step is a step of producing an α, β-unsaturated ketone body (32) by reacting the cyclic amino acid derivative (30) with the olefin Grignard reagent (31). In this step, a reaction well known as a reaction for synthesizing a ketone from a carboxylic acid derivative and a Grignard reagent can be employed. For example, HRSnyder et al., Org. Synth., III, 798 (1955 ); J.Cason et al., J. Org. Chem., Vol. 26, 1768 (1961); GHPosner et al., J. Am. Chem. Soc., Vol. 94, 5106 (1972); and It is carried out according to the method detailed in GHPosner, Org. React., Vol.19, 1 (1972).

Next, the protecting group (R ¹³ ) of the nitrogen atom of the α, β-unsaturated ketone body (32) is removed to form a free body (33) (step 29), and the resulting compound is cyclized (step 30). ), The desired cyclic aminoketone compound (34) can be produced. In the 29th step, a deprotection reaction generally used in organic synthesis (for example, a reaction described in TWGreene et al., Protective Groups in Organic Synthesis, John Willey & Sons, Inc.) can be employed. The deprotection reaction under neutral or acidic conditions is employed. After this deprotection reaction, the resulting compound (33) is immediately cyclized to produce the desired aminoketone compound (34). In the 29th step, when deprotection is performed under acidic conditions, the aminoketone compound (34) is immediately formed by neutralizing the reaction solution.

In the above formula, B, G, R ⁷ , R ¹³ and m are as defined above,
L ″ is a leaving group in the definition of L, the “lower alkylsulfonyl group”; an “arylsulfonyl group” such as benzenesulfonyl, p-toluenesulfonyl group; or a halogeno lower alkylsulfonyl group (for example, trifluoromethanesulfonyl, Pentafluoroethanesulfonyl, etc.). However, at least 4 out of ⁷ R ^{7 in} the compound (37) represent a hydrogen atom.

In steps 31 and 32, first, the protecting group (R ¹³ ) of the ketone compound (35) having a leaving group is removed to obtain a free form (36), and then the free form is closed. This is a step for producing the desired aminoketone compound (37), and is carried out in the same manner as in the <K method> 29th step and 30th step. In addition, the compound (35) which is a starting material in this method is known, or known methods (for example, SWGoldstein et al., J. Org. Chem., Vol. 57, 1179-1190 (1992) B. Achille et al., J. Comb. Chem., Vol. 2, 337-340 (2000), etc.).

In the above formula, G, R ⁷ , R ¹³ and B are as defined above,
R ¹⁴ represents a protecting group for a hydrogen atom or a carboxy group,
R ¹⁵ and R ¹⁶ are the same or different and each represents a hydrogen atom, the “lower alkyl group” or the “aralkyl group”, or R ¹⁵ and R ¹⁶ are a nitrogen atom to which they are bonded. Together with piperidyl, piperazinyl, morpholinyl, thiomorpholinyl, forming a 5- or 6-membered heterocyclyl group containing one nitrogen atom and optionally containing one oxygen atom, sulfur atom or nitrogen atom To do.

However, at least one of the four R ^{7 in} the compound (44) represents a hydrogen atom.

The “carboxy-protecting group” in the definition of R ^{14 represents} a carboxy-protecting group usually used in the field of organic synthesis. Examples of such protecting groups include the “lower alkyl group” and the “ The lower alkenyl group ”and the“ aralkyl group ”can be mentioned, and the“ lower alkyl group ”or the“ aralkyl group ”is preferable.

In the thirty-third and thirty-fourth steps, first, the protecting group (R ¹³ ) of the α-keto acid compound (38) having a leaving group is removed to obtain a free form (39). This is a step of producing a ketolactam compound (40) by ring-closing, and is carried out in the same manner as described in <Method K> step 29 and step 30.

The 35th step is a step of producing a cyclic enaminolactam compound (42) by reacting the ketolactam compound (40) with the secondary amine compound (41). In this step, an enamine synthesis method widely used in the field of organic synthesis reaction can be employed, for example, G. Stork et al., J. Am. Chem. Soc., Vol.
85, 207 (1963), for example, as follows.

  The reaction is usually carried out in a solvent in the presence or absence of an acid.

  Solvents used include aliphatic hydrocarbons such as pentane, hexane and heptane; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and dichloroethane. Ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, s-butanol, isobutanol, t-butanol; N, N-dimethylformamide, Examples include aprotic polar solvents such as N, N-dimethylacetamide and dimethyl sulfoxide; nitriles such as acetonitrile; esters such as methyl acetate and ethyl acetate. Of these, ethers are preferably used.

  Acids used include inorganic acids such as hydrogen chloride, hydrobromic acid, sulfuric acid, perchloric acid, phosphoric acid; and acetic acid, formic acid, succinic acid, methanesulfonic acid, paratoluenesulfonic acid, trifluoroacetic acid, trifluoromethane Organic acids such as sulfonic acid can be mentioned, and sulfuric acid, hydrogen chloride or paratoluenesulfonic acid is preferably used.

  In this step, the reaction can be carried out efficiently by adding molecular sieves or removing water produced using a water separator (for example, Dean Stark Water Separator).

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

  The thirty-sixth step is a step of producing the cyclic enamine compound (43) by reducing the cyclic enaminolactam compound (42). In this step, a reduction reaction for producing an amine from an amide widely used in the field of organic synthesis can be employed, and S. Cortes et al., J. Org. Chem., Vol. 48, 2246 (1983) Y. Tsuda et al., Synthesis, 1977, 652 (1977); HCBrown et al., J. Am. Chem. Soc., Vol.86, 3566 (1964) and RJSundberg et al., J. Org Chem., Vol. 46, 3730 (1981), for example, as follows.

  This reaction is usually performed in a solvent in the presence of a reducing agent.

  Examples of the reducing agent used include sodium borohydride, alkali metal borohydrides such as lithium borohydride, lithium aluminum hydride, and aluminum hydride compounds such as lithium triethoxide aluminum hydride. Examples include hydride reagents; combinations of Lewis acids such as aluminum chloride, tin tetrachloride and titanium tetrachloride with the aforementioned “hydride reagents”; and boron compounds such as diborane. Of these, lithium aluminum hydride is preferably used.

  As the solvent, a nonpolar solvent can be used. Preferably, aliphatic hydrocarbons such as pentane, hexane and heptane; aromatic hydrocarbons such as benzene, toluene and xylene; dichloromethane, chloroform, Halogenated hydrocarbons such as carbon chloride and dichloroethane; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane are used. Of these, ethers are more preferably used.

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

  The 37th step is a step of producing a cyclic aminoketone compound (44) by hydrolyzing the cyclic enamine compound (43). The cyclic enamine compound (43) is acid or base in the presence or absence of a solvent. The reaction is carried out by contact with water in the presence or absence of.

  Examples of the solvent include water or water and an organic solvent (for example, aliphatic hydrocarbons such as pentane, hexane, and heptane; aromatic hydrocarbons such as benzene, toluene, and xylene; dichloromethane, chloroform, carbon tetrachloride, Halogenated hydrocarbons such as dichloroethane; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, s-butanol, isobutanol and t-butanol; Aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and dimethyl sulfoxide; nitriles such as acetonitrile; esters such as methyl acetate and ethyl acetate) It is possible. Of these, water or a mixed solvent of water and alcohols or ethers is preferably used.

  The acid to be used is not particularly limited as long as it is used as an acid in a normal hydrolysis reaction. For example, mineral acids such as hydrochloric acid, sulfuric acid, phosphoric acid; formic acid, acetic acid, propionic acid, trifluoroacetic acid Carboxylic acids such as sulfonic acids such as methanesulfonic acid and ethanesulfonic acid can be raised. Of these, hydrochloric acid, sulfuric acid or acetic acid is preferably used. In addition, progress of this reaction is accelerated | stimulated by adding an acid.

  The base to be used is not particularly limited as long as it is used as a base in a normal hydrolysis reaction. For example, alkali metal hydrides such as sodium hydride and lithium hydride; sodium hydroxide and potassium hydroxide Alkali metal hydroxides such as sodium carbonate and potassium carbonate; triethylamine, tributylamine, pyridine, picoline, 1,8-diazabicyclo [5.4.0] -7-undecene and the like Mention may be made of amines. Of these, sodium hydroxide or potassium hydroxide is preferably used.

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

  Compound (42), which is an intermediate in the production of cyclic aminoketone compound (44), can also be produced by the following <Method N>.

In the above formula, B, G, R ⁷ , R ¹¹ , R ¹² , R ¹⁵ and R ¹⁶ are as defined above,
R ¹⁷ represents a hydrogen atom or a protecting group for a carboxy group.

However, at least one of the four R ^{7 in} the compound (42) represents a hydrogen atom.

The “protecting group for carboxy group” in the definition of R ¹⁷ means a protecting group for a carboxy group usually used in organic synthesis, and as such a group, preferably the “lower alkyl group”, the “ Aralkyl group ”and the like.

  The 38th step is a step of producing an amide diester compound (47) by reacting the cyclic amino acid ester compound (45) with the malonic acid derivative (46) or a reactive derivative thereof. In this step, an amidation reaction widely used in the field of organic synthesis can be adopted, and for example, it is carried out as in the following (a), (b) and (c).

(A) When R ¹⁷ is a hydrogen atom, the reaction is carried out in a solvent in the presence of a condensing agent, in the presence or absence of a base.

  Solvents used include aliphatic hydrocarbons such as pentane, hexane and heptane; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and dichloroethane. Ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, s-butanol, isobutanol, t-butanol; N, N-dimethylformamide, List aprotic polar solvents such as N, N-dimethylacetamide and dimethyl sulfoxide; nitriles such as acetonitrile; esters such as methyl acetate and ethyl acetate; water; It can be. Of these, halogenated hydrocarbons, ethers or esters are preferably used, and dichloromethane, tetrahydrofuran or ethyl acetate is more preferably used.

  Examples of the condensing agent include dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, or N, N′-carbonyldiimidazole.

  Examples of the base to be used include alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and lithium hydride; sodium hydroxide, water Alkali metal hydroxides such as potassium oxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; triethylamine, tributylamine, pyridine, picoline, 1,8-diazabicyclo [5.4.0] -7-undecene Such amines can be mentioned. Of these, amines are preferably used, and triethylamine, pyridine, or 1,8-diazabicyclo [5.4.0] -7-undecene is more preferably used.

  The reaction temperature is usually -20 ° C to 150 ° C, preferably 0 ° C to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

In the case where R ¹⁷ is a hydrogen atom, the compound (46) can be converted into a reactive derivative and then the reaction can be carried out according to the method described in (c) below.

(B) When R ¹⁷ is a protecting group for a carboxy group (preferably, the “lower alkyl group” or the “aralkyl group”), the reaction is achieved by heating in the presence or absence of a solvent. Is done.

  When the reaction is performed in a solvent, a solvent similar to the solvent described in (a) can be used, and the reaction temperature is 30 ° C. to 100 ° C., preferably the boiling point of the solvent used. Of ± 5 ° C. Particularly preferably, the reaction is carried out by heating the reaction under reflux.

  When a solvent is not used, the reaction can be carried out by mixing compound (45) and compound (46) and heating the mixture. The reaction temperature is 30 ° C to 150 ° C, preferably 50 ° C to 120 ° C.

  The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

  (C) When a reactive derivative of compound (46) is used, the “reactive derivative” means an acid halide, mixed acid anhydride, active ester, active amide, etc., and the reaction is carried out in a solvent in a condensing agent. It is carried out in the presence, in the presence or absence of a base.

An “acid halide” can be obtained by reacting a compound (46) in which R ¹⁷ is hydrogen with a halogenating agent (eg, thionyl chloride, oxalyl chloride, etc.); It can be obtained by reacting a compound (46) in which R ¹⁷ is hydrogen with an acid halide (eg, methyl chlorocarbonate, ethyl chlorocarbonate, etc.); an “active ester” is a compound in which R ¹⁷ is hydrogen (46) can be obtained by reacting a hydroxy compound (for example, N-hydroxysuccinimide, N-hydroxyphthalimide, etc.) in the presence of the “condensing agent” described in (a); active amide "(for example, Weinreb amide) ^are compounds ^{R 17} is hydrogen and (46) N-lower alkoxy -N- lower alkyl hydroxylamine ( In example it can be obtained by reacting in the presence of stated N- methoxy -N- methyl-hydroxylamine, etc.) and with (a) "condensing agent". Both are carried out by applying reaction conditions widely used in ordinary organic synthetic chemistry.

  

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

  In the 39th and 40th steps, the amide diester compound (47) is subjected to a Dieckmann reaction to produce a ketolactam ester compound (48), followed by hydrolysis and decarboxylation to produce a ketolactam compound (49). <Method J> The same as the 25th and 26th steps.

  The 41st step is a step of producing a cyclic enaminolactam compound (42) by reacting the ketolactam compound (49) with the secondary amine compound (41), and is carried out in the same manner as in the <Method M> 35th step. Is done.

  Furthermore, the compound (48) which is an intermediate in the above <Method N> can also be produced by the following <Method O>.

In the above formula, B, G, R ⁷ , R ¹² and R ¹⁷ are as defined above.

However, at least one of the four R ^{7 in} the compound (48) represents a hydrogen atom.

  The forty-second step is a step of producing an amide monoester compound (51) by reacting the cyclic amino acid (50) with the malonic acid derivative (46) or a reactive derivative thereof. <Method N> ), (B) and (c).

The 43rd step is a step of producing the ketolactam ester compound (48) by condensing the carboxy group of the amide monoester compound (51) and the active methylene group in the molecule to cyclize. In this step, compound (51) can be used as it is, or compound (51) can be converted into a reactive derivative and used.
(A) When compound (51) is used as it is, the reaction is carried out in a solvent in the presence of a condensing agent and in the presence or absence of a base.

  Solvents used include halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane; methanol, ethanol, propanol, isopropanol, butanol, s Alcohols such as butanol, isobutanol and t-butanol; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and dimethyl sulfoxide; nitriles such as acetonitrile; methyl acetate; Mention may be made of esters such as ethyl acetate; water; or a mixed solvent thereof. Of these, halogenated hydrocarbons, ethers or esters are preferably used, and dichloromethane, tetrahydrofuran or ethyl acetate is more preferably used.

  Examples of the condensing agent include dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, or N, N′-carbonyldiimidazole.

  Examples of the base to be used include alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and lithium hydride; sodium hydroxide, water Alkali metal hydroxides such as potassium oxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; triethylamine, tributylamine, pyridine, picoline, 1,8-diazabicyclo [5.4.0] -7-undecene Such amines can be mentioned. Of these, amines are preferably used, and triethylamine, pyridine, or 1,8-diazabicyclo [5.4.0] -7-undecene is more preferably used.

The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.
(B) When the compound (51) is used as a reactive derivative and used, examples of the reactive derivative include acid halides, mixed acid anhydrides, active esters, and active amides.

  The acid halide can be obtained by reacting the compound (51) with a halogenating agent (eg, thionyl chloride, oxalyl chloride, etc.); the mixed acid anhydride can be obtained by reacting the compound (51) with an acid halide (eg, Active ester can be obtained by reacting compound (51) with a hydroxy compound (for example, N-hydroxysuccinimide, N-hydroxyphthalimide, etc.) Can be obtained by reacting in the presence of a “condensing agent” as described in (a); “active amide” (for example, Weinreb amide) can be obtained by reacting compound (51) with N-lower alkoxy-N-lower. An alkylhydroxylamine (eg N-methoxy-N-methylhydroxylamine etc.) as described in (a) It can be obtained by reacting in the presence of an “agent”. Both are carried out by applying reaction conditions widely used in ordinary organic synthetic chemistry.

  The ring closure reaction of the reactive derivative is usually performed in a solvent in the presence or absence of a base.

  

  The reaction temperature is usually −20 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 12 hours.

In the above formula, G, Hal and R ⁷ are as defined above,
R ¹⁸ represents a lower alkyl group (preferably a methyl group or an ethyl group),
p represents 1 to 3. However, at least 6 out of 9 R ^{7 in} the compound (58) represent a hydrogen atom.

  The 44th step is a step of reacting the cyano compound (52) and the halogen compound (53) to produce the compound (54), and the 45th step is to reduce the cyano group of the compound (54) to produce amino In this step, the compound (55) is produced.

  The 46th step is a step of reacting the amino compound (55) with the α, β-unsaturated ketone compound (56) to produce the compound (58) via the compound (57).

  The reaction of the series of the 44th, 45th and 46th steps (namely, <Method P>) is detailed in Frank D. King, J. Chem. Soc., Perkin Trans. 1, 1986, 447-453 (1986). It is carried out according to the method described.

In the <Method I> to <Method P> described above as the production method of the compound (3), G represents a group having the formula Z (R ⁵ _a ) (R ⁶ ) _n [R ⁶ , n and Z are the same as defined above. R ⁵ _a represents a substituent in the definition of R ^5, a halogen atom or a group having the formula SR ^c (R ^c is as defined above). The group having the formula SR ^c may be a group having the formula SOR ^c or the formula SO ₂ R ^{c in the same} manner as in the <Method H> step 21 or step 22 in any subsequent step. Can be converted to a group having

  Moreover, a halogen atom can also be converted into a carboxy group or a lower alkoxycarbonyl group by <Method Q> shown below in any subsequent step.

In the above formula, Hal, n, R ⁶ and Z are as defined above,
R ¹⁹ _a represents a lower alkyl group (preferably a methyl group or an ethyl group), and R ¹⁹ _b represents a hydrogen atom or a lower alkyl group.

  The reaction in the former stage of the 47th step, that is, (i) halogen metal exchange reaction is carried out according to the method detailed in, for example, M. Schlosser et al., Organometallics in Synthesis, John Wiley & Sons, Ltd. The

  Inert solvents used in the halogen metal exchange reaction are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, and preferably Are ethers.

  Examples of the metalating agent used in the halogen metal exchange reaction include alkali metals such as lithium, sodium, potassium, methyllithium, butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) amide; or magnesium, isopropylmagnesium bromide , Alkaline earth metals such as diisopropylmagnesium, and preferably butyllithium.

  The reaction temperature varies depending on the raw material compound, the solvent, the type of the metallizing agent and the like, but is usually −100 ° C. to 100 ° C., and preferably −70 ° C. to 0 ° C.

  The reaction time varies depending on the raw material compound, the solvent, the type of metallizing agent, the reaction temperature, etc., but is usually 5 minutes to 10 hours, preferably 10 minutes to 5 hours.

  The metalated compound thus obtained is usually used for subsequent reaction with carbon dioxide or chlorocarbonates without post-treatment and isolation of the reaction.

  Inert solvents used for the reaction with carbon dioxide or chlorocarbonates are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and dichloroethane; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane. And preferred are ethers.

  The reaction temperature varies depending on the raw material compound, the solvent, the type of the metallizing agent and the like, but is usually −100 ° C. to 100 ° C., preferably −70 ° C. to 0 ° C.

  The reaction time varies depending on the raw material compound, the solvent, the type of metallizing agent, the reaction temperature, etc., but is usually 5 minutes to 10 hours, preferably 10 minutes to 5 hours.

  In <Method J> to <Method O>, all of compounds (24), (30), (35), (38), (45) and (50) used as starting materials or auxiliary materials are used. It is a derivative of homopurine and is disclosed in JP-A No. 2001-247564 (EP1070711), JP-A No. 2002-284780 (WO02 / 57255), JP-A No. 2002-284682 (WO02 / 57265), JP-A No. 2002-284783. (WO02 / 57264) to JP-A-2004-099600 (WO2004 / 009592).

  In <Method J> to <Method P>, all of the raw material compounds (23), (31), (41), (46), (52) and (53) are known per se, or are publicly known This compound can be easily obtained from the above compound by treating according to a known method.

  Compound (5) can be produced according to the following <Method R>.

  In the above formula, Hy, Hy 'and L have the same meaning as described above.

  The forty-eighth step is a step for producing compound (5a) by converting the hydroxyl group of compound (3 ′), which is a tautomer of heterocyclyl ketone (3), to a leaving group. 3 ') and halogenating agents (eg fluorinating agents such as diethylaminosulfur trifluoride (DAST); such as thionyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, triphenylphosphine / carbon tetrachloride Brominating agents such as hydrobromic acid, thionyl bromide, phosphorus tribromide, triphenylphosphine / carbon tetrabromide; or iodinating agents such as hydroiodic acid, phosphorus triiodide Etc.), sulfonyl halides (for example, methanesulfonyl chloride, p-toluenesulfonyl chloride, etc.) or sulfonic anhydrides (for example, trifluoromethanesulfonic anhydride, etc.) It is carried out by.

  The 49th step is a step of producing heterocyclyl alcohol (61) by reducing heterocyclyl ketone (3). For example, alkali metal borohydride such as sodium borohydride, lithium borohydride; lithium aluminum hydride; Aluminum hydride compounds such as lithium triethoxide aluminum hydride; Tellurium hydride sodium; Diisobutylaluminum hydride, di (methoxyethoxy) aluminum sodium dihydride and other hydride reagents such as organoaluminum hydride reducing agents are used. Reduction reactions, or catalytic reduction with hydrogen, can be employed, for example, J. Dale, J. Chem. Soc., 910 (1961) and FGBordwell et al., J. Org. Chem., According to the method detailed in vol.33, 3385 (1968).

  The 50th step is a step of producing the compound (5a) by converting the hydroxyl group of the heterocyclyl alcohol (61) to a leaving group, and is carried out in the same manner as in the 48th step.

  Compound (6) is easily produced from compound (5a) or (5b) described in <Method R> by a conventional method.

  Compound (12) is produced by the <Method S> shown below.

In the above formula, the bond including the dotted line, R ¹ , R ² , R ⁷ , R ¹³ and m are as defined above.

  The 51st step and the 52nd step are performed in the same manner as the <Process A> second step, third step and fourth step.

Among the compounds (13), a compound in which R ⁵ in G is a group having the formula SO ₂ NR ^a R ^b is produced by the <Method T> shown below.

In the above formula, R ^a , R ^b , R ⁶ , L, n, X, Y and Z are as defined above.

  The 54th step is a step of producing the compound (66) by chlorosulfonylating the aromatic ring part (Z) of the compound (65) with chlorosulfonic acid, and the 55th step is a step of producing the compound (66) and the amine compound (16). ) To produce a sulfonamide compound (13a).

  The 54th and 55th steps are performed according to the method described in detail in G.E.Inskeep et. Al., JACS., Vol.69, 2237-2238 (1947).

  Furthermore, the compound (15) can also be produced by the aforementioned <Method Q>.

  After completion of each of the above reactions, the target compound is collected from the reaction mixture according to a conventional method.

  For example, the reaction mixture is appropriately neutralized, and if insoluble matter is present, it is removed by filtration, water and an immiscible organic solvent such as ethyl acetate are added, washed with water, and the target compound is then contained. The organic layer is separated, dried over anhydrous magnesium sulfate and the like, and then the solvent is distilled off.

  If necessary, the obtained target compound can be obtained by a conventional method such as recrystallization, reprecipitation, or a method usually used for separation and purification of organic compounds, for example, silica gel, alumina, magnesium-silica gel-type florisil. Adsorption column chromatography using a simple carrier; such as Sephadex LH-20 (Pharmacia), Amberlite XAD-11 (Rohm and Haas), Diaion HP-20 (Mitsubishi Chemical) A method using a synthetic adsorbent such as partition column chromatography using a simple carrier, a method using ion exchange chromatography, or a normal phase / reverse phase column chromatography method using silica gel or alkylated silica gel (preferably high-speed Liquid chromatography)) and combined elution with an appropriate eluent. Separation Te, can be purified.

  The administration form of the compound having the general formula (I) of the present invention or a pharmacologically acceptable salt thereof is, for example, oral administration by tablets, capsules, granules, powders or syrups, or injections or suppositories. Parenteral administration. These preparations are produced by known methods using additives such as excipients, lubricants, binders, disintegrants, stabilizers, flavoring agents, and diluents.

  Here, the excipient includes, for example, sugar derivatives such as lactose, sucrose, glucose, mannitol, sorbit; starch derivatives such as corn starch, potato starch, α-starch, dextrin, carboxymethyl starch; crystalline cellulose, Low substituted hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, carboxymethylcellulose calcium, cellulose derivatives such as internally cross-linked sodium carboxymethylcellulose; gum arabic; dextran; organic excipients such as pullulan; or light anhydrous silicic acid, synthetic silicic acid Aluminum, silicate derivatives such as magnesium metasilicate aluminate; phosphates such as calcium phosphate; carbonates such as calcium carbonate; sulfates such as calcium sulfate A inorganic excipients.

  Lubricants include, for example, stearic acid metal salts such as stearic acid, calcium stearate and magnesium stearate; talc; colloidal silica; waxes such as bee gum and gay wax; boric acid: adipic acid; sulfuric acid such as sodium sulfate Salt; glycol; fumaric acid; sodium benzoate; DL-leucine; fatty acid sodium salt; lauryl sulfate such as sodium lauryl sulfate and magnesium lauryl sulfate; silicic acid such as anhydrous silicic acid and silicic acid hydrate; It is.

  The binder is, for example, polyvinyl pyrrolidone, macrogol or a compound similar to the excipient.

  The disintegrant is, for example, a compound similar to the above-mentioned excipient or a chemically modified starch / cellulose such as croscarmellose sodium, sodium carboxymethyl starch, or crosslinked polyvinylpyrrolidone.

  Stabilizers include, for example, paraoxybenzoates such as methylparaben and propylparaben; alcohols such as chlorobutanol, benzyl alcohol and phenylethyl alcohol; benzalkonium chloride; phenols such as phenol and cresol; thimerosal; Dehydroacetic acid; or sorbic acid. Examples of the flavoring agent include sweeteners, acidulants, and fragrances that are usually used.

  The amount of the compound having the general formula (I) of the present invention or a pharmacologically acceptable salt thereof varies depending on the symptom, age, administration method, etc. It is desirable to administer 0.1 mg (preferably 0.5 mg) as the lower limit and 2000 mg (preferably 500 mg) as the upper limit in one or several divided doses depending on the symptoms. In the case of intravenous administration, the lower limit is 0.01 mg (preferably 0.05 mg) and the upper limit is 200 mg (preferably 50 mg) per day for adults. Is desirable.

  Hereinafter, the present invention will be described in more detail with reference to Examples, Reference Examples, Formulation Examples and Test Examples, but the present invention is not limited thereto.

Example 1
4- [1- (4-Ethoxycarbonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H- Pyrrole (Exemplary Compound No. 1-360)
2- (4-Fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole (European Patent Application Publication No. 1070711) 639 mg (2 mmol) and 4-ethoxycarbonylphenethyl bromide 1.03 g (4 mmol) are dissolved in 15 ml of dimethylformamide, 1.38 g (10 mmol) of potassium carbonate is added, and 5% at 80 ° C. is added. Stir for hours. 40 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained solid was washed with a small amount of methanol and recrystallized from methanol to obtain 434 mg of the title compound as white fine needles (yield 44%).

Melting point: 217-218 ° C
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.36 (1H, s), 8.45 (2H, d, J = 6Hz), 7.87 (2H, d, J = 8Hz),
7.37 (2H, d, J = 8Hz), 7.18-7.09 (6H, m), 6.90 (1H, d, J = 3Hz),
5.25 (1H, s), 4.30 (2H, quartet, J = 7Hz), 2.94 (2H, br.s),
2.82 (2H, t, J = 8Hz), 2.62-2.56 (4H, m), 2.16 (2H, br.s),
1.31 (3H, t, J = 7Hz).

(Example 2)
4- [1- (4-Carbamoylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole (Exemplary Compound No. 1-366)
The same reaction as in Example 1 was carried out using 4-carbamoylphenethyl chloride in place of 4-ethoxycarbonylphenethyl bromide to obtain the title compound as a light brown powder (yield 32%).

Melting point: 202-204 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.36 (1H, s), 8.46 (2H, d, J = 5Hz), 7.88 (1H, s),
7.78 (2H, d, J = 10Hz), 7.28 (2H, d, J = 10Hz), 7.25 (1H, s),
7.16-7.10 (6H, m), 6.90 (1H, s), 5.25 (1H, s), 2.92 (2H, br.s),
2.78 (2H, t, J = 10Hz), 2.58-2.53 (4H, m), 2.16 (2H, m).

(Example 3)
3- [1- (4-Carbamoylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -5- (4-fluorophenyl) -4- (pyridin-4-yl) -1H-pyrazole (Exemplary compound number 10-366)
Instead of 2- (4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, 5- (4-fluoro Phenyl) -4- (pyridin-4-yl) -3- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrazole was used for the same reaction as in Example 2, The compound was obtained as a slightly yellow powder (yield 5%).

Melting point: 182-186 ° C
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
13.17 (1H, br.s), 8.50 (2H, d, J = 6Hz), 7.86 (1H, br.s),
7.75 (2H, d, J = 8Hz), 7.31-7.21 (5H, m), 7.16 (2H, d, J = 6Hz),
7.19-7.07 (2H, br.s), 5.72 (1H, br), 3.06-2.93 (2H, br.s),
2.79 (2H, t, J = 8Hz), 2.64-2.54 (4H, m), 2.37-2.12 (2H, br.s).

Example 4
4- [1- (4-Carboxyphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole (Exemplary compound number 1-358)
4- [1- (4-Ethoxycarbonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4) obtained in Example 1 -Il) -1H-pyrrole 140 mg (0.28 mmol) was dissolved in ethanol 7 ml, 1M lithium hydroxide aqueous solution 0.85 ml (0.85 mmol) was added, and the mixture was stirred at 80 ° C. for 30 minutes, and then cooled to room temperature. . The reaction mixture was acidified with 1N hydrochloric acid and concentrated under reduced pressure. The precipitated solid was filtered and washed with ethanol to give 117 mg of the title compound as a pale yellow powder (yield 89%).

Melting point: 239-240 ° C
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.36 (1H, s), 8.44 (2H, d, J = 5Hz), 7.85 (2H, d, J = 8Hz),
7.34 (2H, d, J = 8Hz), 7.18-7.09 (6H, m), 6.91 (1H, d, J = 3Hz),
5.25 (1H, br.s), 2.94 (2H, d, J = 3Hz), 2.81 (2H, t, J = 7Hz),
2.61-2.54 (4H, m), 2.16 (2H, br.s).

(Example 5)
2- (4-Fluorophenyl) -4- [1- [4- (N-methylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole (Exemplified Compound No. 1-367)
4- [1- (4-Carboxyphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4-) obtained in Example 4 Yl) -1H-pyrrole (500 mg, 1.07 mmol) was dissolved in dimethylformamide (8 ml), carbonyldiimidazole (347 mg, 2.14 mmol) was added and the mixture was stirred at room temperature for 30 minutes, and then 2M methylamine / tetrahydrofuran solution (1.07 ml) 2.14 mmol) was added and stirred at room temperature for an additional 30 minutes. To the reaction solution was added 10 ml of saturated sodium bicarbonate solution and stirred, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained solid was washed with a small amount of ethanol to obtain 473 mg of the title compound as a light brown powder (yield 92%).

Melting point: 231-233 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.37 (1H, s), 8.46 (2H, d, J = 6Hz), 8.34-8.33 (1H, m),
7.74 (2H, d, J = 8Hz), 7.30 (2H, d, J = 8Hz), 7.18-7.09 (6H, m),
6.91 (1H, d, J = 2Hz), 5.25 (1H, s), 2.92 (2H, s),
2.80-2.73 (5H, m), 2.58-2.53 (4H, m), 2.15 (2H, br.s).

(Example 6)
4- [1- [4- (N-ethylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) ) -1H-pyrrole (Exemplified Compound No. 1-368)
The same reaction as in Example 5 was performed using ethylamine instead of methylamine to obtain the title compound as a light brown powder (yield 91%).

Melting point: 228-230 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.36 (1H, s), 8.46 (2H, dd, J = 4Hz, 2Hz), 8.36 (1H, t, J = 6Hz),
7.75 (2H, d, J = 8Hz), 7.29 (2H, d, J = 8Hz), 7.18-7.09 (6H, m),
6.91 (1H, d, J = 3Hz), 5.25 (1H, s), 3.29-3.23 (2H, m),
2.92 (2H, d, J = 2Hz), 2.78 (2H, t, J = 8Hz), 2.58-2.52 (4H, m),
2.15 (2H, s), 1.11 (3H, t, J = 7Hz).

(Example 7)
4- [1- [4- (N-cyclopropylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4- Yl) -1H-pyrrole (Exemplified Compound No. 1-374)
The same reaction as in Example 5 was performed using cyclopropylamine instead of methylamine to obtain the title compound as a light brown powder (yield 96%).

Melting point: 226-228 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.37 (1H, br.s), 8.45 (2H, d, J = 6Hz), 8.34 (1H, d, J = 5Hz),
7.72 (2H, d, J = 8Hz), 7.27 (2H, d, J = 8Hz), 7.20-7.07 (6H, m),
6.90 (1H, d, J = 3Hz), 5.28-5.22 (1H, m), 2.95-2.88 (2H, m),
2.87-2.72 (3H, m), 2.61-2.48 (4H, m), 2.19-2.10 (2H, m),
0.71-0.65 (2H, m), 0.58-0.52 (2H, m).

(Example 8)
2- (4-Fluorophenyl) -4- [1- [4- (N-isopropylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole (Exemplified Compound No. 1-370)
The same reaction as in Example 5 was performed using isopropylamine instead of methylamine to obtain the title compound as a light brown powder (yield 94%).

Melting point: 178-180 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.38 (1H, br.s), 8.45 (2H, d, J = 6Hz), 8.11 (1H, d, J = 8Hz),
7.75 (2H, d, J = 8Hz), 7.28 (2H, d, J = 8Hz), 7.22-7.06 (6H, m),
6.90 (1H, d, J = 3Hz), 5.28-5.22 (1H, m), 4.14-4.01 (1H, m),
2.98-2.88 (2H, m), 2.82-2.72 (2H, m), 2.62-2.48 (4H, m),
2.21-2.10 (2H, m), 1.15 (6H, d, J = 7Hz).

Example 9
2- (4-Fluorophenyl) -4- [1- [4- (N-propylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole (Exemplified Compound No. 1-369)
The same reaction as in Example 5 was carried out using propylamine instead of methylamine to obtain the title compound as a white powder (yield 83%).

Melting point: 227-230 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.37 (1H, br.s), 8.45 (2H, d, J = 6Hz), 8.36 (1H, t, J = 6Hz),
7.74 (2H, d, J = 8Hz), 7.29 (2H, d, J = 8Hz), 7.19-7.08 (6H, m),
6.90 (1H, d, J = 2Hz), 5.25 (1H, s), 3.24-3.16 (2H, m), 2.95-2.89 (2H, m),
2.82-2.74 (2H, m), 2.60-2.52 (4H, m), 2.19-2.12 (2H, m),
1.57-1.46 (2H, m), 0.88 (3H, t, J = 7Hz).

(Example 10)
4- [1- [4- [N- (2-Fluoroethyl) carbamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- ( Pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 1-389)
The same reaction as in Example 5 was performed using 2-fluoroethylamine instead of methylamine to obtain the title compound as a white powder (yield 78%).

Melting point: 209-211 ° C
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.37 (1H, br.s), 8.61 (1H, t, J = 6Hz), 8.45 (2H, d, J = 6Hz),
7.78 (2H, d, J = 8Hz), 7.31 (2H, d, J = 8Hz), 7.18-7.09 (6H, m),
6.90 (1H, d, J = 2Hz), 5.25 (1H, s), 4.59 (1H, t, J = 5Hz),
4.47 (1H, t, J = 5Hz), 3.58 (1H, dd, J = 11Hz, 5Hz),
3.52 (1H, dd, J = 11Hz, 5Hz), 2.93-2.88 (2H, m),
2.80-2.73 (2H, m), 2.58-2.50 (4H, m), 2.16-2.10 (2H, m).

(Example 11)
4- [1- [4- (N-cyclohexylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) ) -1H-pyrrole (Exemplified Compound No. 1-377)
The same reaction as in Example 5 was carried out using cyclohexylamine instead of methylamine to obtain the title compound as a light brown powder (yield 94%).

Melting point: 243-245 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.37 (1H, s), 8.46 (2H, d, J = 6Hz), 8.09 (1H, d, J = 8Hz),
7.75 (2H, d, J = 8Hz), 7.28 (2H, d, J = 8Hz), 7.18-7.09 (6H, m),
6.90 (1H, d, J = 3Hz), 5.25 (1H, s), 3.75 (1H, br.s), 2.92 (2H, s),
2.78 (2H, t, J = 8Hz), 2.58-2.52 (4H, m), 2.15 (2H, br.s), 1.80 (2H, br.s),
1.73 (2H, br.s), 1.59 (2H, br.s), 1.29 (4H, t, J = 10Hz).

(Example 12)
4- [1- [4- (N-cyclopentylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) ) -1H-pyrrole (Exemplified Compound No. 1-376)
The same reaction as in Example 5 was carried out using cyclopentylamine in place of methylamine to obtain the title compound as a light brown powder (yield 95%).

Melting point: 192-195 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.37 (1H, s), 8.46 (2H, d, J = 6Hz), 8.17 (1H, d, J = 7Hz),
7.75 (2H, d, J = 8Hz), 7.29 (2H, d, J = 9Hz), 7.15-7.09 (6H, m),
6.90 (1H, s), 5.25 (1H, s), 4.24-4.19 (1H, m), 2.92 (2H, s),
2.78 (2H, t, J = 7Hz), 2.58-2.54 (4H, m), 2.15 (2H, br.s), 1.87 (2H, br.s),
1.69 (2H, br.s), 1.52 (4H, br.s).

(Example 13)
4- [1- [4- [N-[(1S) -Ethoxycarbonylethyl] carbamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl)- 3- (Pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 1-397)
The same reaction as in Example 5 was carried out using L-alanine ethyl ester instead of methylamine to obtain the title compound as a white powder (yield 86%).

Melting point: 169-172 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.36 (1H, br.s), 8.66 (1H, d, J = 7Hz), 8.45 (2H, d, J = 6Hz),
7.79 (2H, d, J = 8Hz), 7.32 (2H, d, J = 8Hz), 7.18-7.06 (6H, m),
6.90 (1H, d, J = 2Hz), 5.25 (1H, s), 4.47-4.40 (1H, m), 4.14-4.06 (2H, m),
2.93-2.88 (2H, m), 2.80-2.73 (2H, m), 2.59-2.50 (4H, m),
2.16-2.10 (2H, m), 1.39 (3H, d, J = 7Hz), 1.18 (3H, t, J = 7Hz).

(Example 14)
4- [1- [4- [N- (Ethoxycarbonylmethyl) carbamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine -4-yl) -1H-pyrrole (Exemplified Compound No. 1-396)
The same reaction as in Example 5 was carried out using glycine ethyl ester instead of methylamine to obtain the title compound as a white powder (yield 94%).

Melting point: 170-173 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.37 (1H, br.s), 8.82 (1H, t, J = 6Hz), 8.45 (2H, d, J = 7Hz),
7.78 (2H, d, J = 8Hz), 7.33 (2H, d, J = 8Hz), 7.18-7.06 (6H, m),
6.90 (1H, d, J = 2Hz), 5.26 (1H, s), 4.12 (2H, quartet, 7Hz),
3.98 (2H, d, J = 6Hz), 2.93-2.88 (2H, m), 2.80-2.73 (2H, m),
2.58-2.50 (4H, m), 2.16-2.10 (2H, m), 1.20 (3H, t, J = 7Hz).

(Example 15)
4- [1- [4- [2- (N, N-dimethylamino) ethoxycarbonyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl)- 3- (Pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 1-1338)
4- [1- (4-Carboxyphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4-) obtained in Example 4 Yl) -1H-pyrrole (500 mg, 1.07 mmol) was dissolved in dimethylformamide (10 ml), carbonyldiimidazole (347 mg, 2.14 mmol) was added, and the mixture was stirred at room temperature for 30 minutes, and then 2- (N, N-dimethylamino). Ethanol 0.21 ml (2.14 mmol) was added and stirred at 60 ° C. for 2 days. 50 ml of water was added to the reaction solution, and the precipitated solid was collected by filtration and washed with diethyl ether to obtain 433 mg of the title compound as a white powder (yield 75%).

Melting point: 178-181 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.36 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.86 (2H, d, J = 8Hz),
7.36 (2H, d, J = 8Hz), 7.18-7.09 (6H, m), 6.90 (1H, d, J = 2Hz),
5.25 (1H, s), 4.34 (2H, t, J = 6Hz), 2.93-2.88 (2H, m),
2.83-2.77 (2H, m), 2.61-2.50 (6H, m), 2.21 (6H, s), 2.16-2.11 (2H, m).

(Example 16)
4- [1- (3-Carboxyphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole (Exemplary compound number 3-2)
The same reaction as in Example 1 was carried out using 3-ethoxycarbonylphenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide to give 4- [1- (3-ethoxycarbonylphenethyl) -1,2,3,6-tetrahydro. Pyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole was obtained. The ester was then hydrolyzed in the same manner as in Example 4 to obtain the title compound as a light brown powder (yield 83%).

Melting point: 256-260 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.38 (1H, s), 8.45 (2H, d, J = 6Hz), 7.80-7.75 (2H, m),
7.47 (1H, d, J = 7Hz), 7.39 (1H, t, J = 8Hz), 7.18-7.08 (6H, m),
6.91 (1H, s), 5.25 (1H, s), 2.95 (2H, s), 2.81 (2H, t, J = 7Hz),
2.61-2.56 (4H, m), 2.17 (2H, s).

(Example 17)
4- [1- (3-carbamoylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole (Exemplary compound number 3-4)
The same reaction as in Example 1 was carried out using 3-carbamoylphenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide to obtain the title compound as a brown powder (yield 69%).

Melting point: 185-188 ° C
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.37 (1H, s), 8.46 (2H, d, J = 6Hz), 7.91 (1H, s), 7.73 (1H, s),
7.69 (1H, d, J = 7Hz), 7.36-7.30 (3H, m), 7.18-7.09 (6H, m),
6.91 (2H, d, J = 2Hz), 5.26 (1H, s), 2.94 (1H, s), 2.78 (2H, t, J = 7Hz),
2.59-2.54 (4H, m), 2.16 (2H, br.s).

(Example 18)
2- (4-Fluorophenyl) -3- (pyridin-4-yl) -4- [1- (4-sulfamoylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -1H -Pyrrole (Exemplary Compound No. 1-435)
The same reaction as in Example 1 was carried out using 4-sulfamoylphenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide to obtain the title compound as a yellow powder (yield 25%).

Melting point: 220-221 ° C
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.36 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.72 (2H, d, J = 8Hz),
7.40 (2H, d, J = 8Hz), 7.26 (2H, br.s), 7.20-7.06 (6H, m),
6.90 (1H, d, J = 2Hz), 5.26 (1H, br.s), 2.96-2.88 (2H, br.s),
2.81 (2H, t, J = 8Hz), 2.61-2.52 (4H, m), 2.19-2.10 (2H, br.s).

(Example 19)
2- (4-Fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-436)
The same reaction as in Example 1 was carried out using 4- (N-methylsulfamoyl) phenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide, and 2- (4-fluorophenyl) -4- [1- [4 -(N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole was obtained. This was then suspended in ethanol, 1 equivalent of 1N hydrochloric acid was added and the solvent was distilled off. The residue was washed with ethanol to give the title compound as a pale yellow powder (yield 60%).

Melting point: 222-223 ° C
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.35 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.67 (2H, d, J = 8Hz),
7.67 (2H, d, J = 8Hz), 7.39-7.33 (1H, m), 7.18-7.08 (6H, m),
6.92-6.89 (1H, m), 5.28-5.24 (1H, m), 2.95-2.90 (2H, m),
2.83 (2H, t, J = 8Hz), 2.60 (2H, t, J = 8Hz), 2.56-2.52 (2H, m),
2.39 (3H, s), 2.19-2.12 (2H, m).

(Example 20)
4- [1- [4- (N-ethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4 -Yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-437)
The same reaction as in Example 19 was carried out using 4- (N-ethylsulfamoyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a slightly yellow powder. (Yield 60%).

Melting point: 260-261 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.34 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.68 (2H, d, J = 8Hz),
7.49-7.41 (3H, m), 7.19-7.08 (6H, m), 6.90 (1H, d, J = 2Hz),
5.27-5.23 (1H, m), 2.95-2.90 (2H, m), 2.82 (2H, t, J = 8Hz),
2.78-2.71 (2H, m), 2.58 (2H, t, J = 8Hz), 2.54 (2H, t, J = 6Hz),
2.18-2.12 (2H, m), 0.96 (3H, t, J = 8Hz).

(Example 21)
2- (4-Fluorophenyl) -4- [1- [4- (N-propylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-438)
The same reaction as in Example 19 was carried out using 4- (N-propylsulfamoyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a pale yellow powder. (Yield 59%).

Melting point: 253-254 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.35 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.68 (2H, d, J = 8Hz),
7.51-7.46 (1H, m), 7.43 (2H, d, J = 8Hz), 7.19-7.08 (6H, m),
6.90 (1H, d, J = 2Hz), 5.27-5.23 (1H, m), 2.96-2.89 (2H, m),
2.82 (2H, t, J = 8Hz), 2.70-2.63 (2H, m), 2.58 (2H, t, J = 8Hz),
2.54 (2H, t, J = 6Hz), 2.19-2.12 (2H, m), 1.40-1.31 (2H, m), 0.78 (3H, t, J = 8Hz).

(Example 22)
2- (4-Fluorophenyl) -4- [1- [4- (N-isopropylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-439)
The same reaction as in Example 19 was carried out using 4- (N-isopropylsulfamoyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a pale yellow powder. (Yield 40%).

Melting point: 178-180 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.34 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.70 (2H, d, J = 8Hz),
7.50-7.45 (1H, m), 7.42 (2H, d, J = 8Hz), 7.19-7.08 (6H, m),
6.90 (1H, d, J = 2Hz), 5.27-5.23 (1H, m), 3.25-3.16 (1H, m),
2.94-2.89 (2H, m), 2.82 (2H, t, J = 8Hz), 2.58 (2H, t, J = 8Hz),
2.54 (2H, t, J = 6Hz), 2.18-2.12 (2H, m), 0.92 (6H, d, J = 6Hz).

(Example 23)
2- (3-Chloro-4-fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-555)
Instead of 2- (4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, 2- (3-chloro -4-Fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole was used for the same reaction as in Example 19. The title compound was obtained as a brown powder (yield 45%).

Melting point: 183-185 ° C
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.49 (1H, s), 8.50 (2H, d, J = 6Hz), 7.68 (2H, d, J = 8Hz),
7.46 (2H, d, J = 9Hz), 7.36-7.29 (3H, m), 7.17 (2H, d, J = 6Hz),
7.05-7.01 (1H, m), 6.97 (1H, d, J = 3Hz), 5.25 (1H, s),
2.89 (2H, br.s), 2.83 (2H, t, J = 8Hz),
2.62-2.53 (4H, m), 2.39 (3H, d, J = 5Hz), 2.16 (2H, br.s).

(Example 24)
4- [1- [4- (N-cyclopropylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine- 4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-443)
The same reaction as in Example 19 was carried out using 4- (N-cyclopropylsulfamoyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a pale yellow powder. (Yield 55%).

Melting point: 261-262 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.34 (1H, br.s), 8.45 (2H, t, J = 6Hz), 7.84-7.79 (1H, m),
7.71 (2H, d, J = 8Hz), 7.45 (2H, d, J = 8Hz), 7.18-7.08 (6H, m),
6.90 (1H, d, J = 3Hz), 5.27-5.23 (1H, m), 2.95-2.90 (2H, m),
2.83 (2H, t, J = 8Hz), 2.59 (2H, t, J = 8Hz), 2.54 (2H, t, J = 6Hz),
2.18-2.12 (2H, m), 2.09-2.03 (1H, m), 0.48-0.43 (2H, m), 0.38-0.33 (2H, m).

(Example 25)
4- [1- [4- [N- (2-fluoroethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- ( Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-458)
The reaction was conducted in the same manner as in Example 19 using 4- [N- (2-fluoroethyl) sulfamoyl] phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide. (Yield 42%).

Melting point: 259-260 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.34 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.90-7.82 (1H, m),
7.70 (2H, d, J = 8Hz), 7.44 (2H, d, J = 8Hz), 7.19-7.08 (6H, m),
6.90 (1H, d, J = 2Hz), 5.27-5.23 (1H, m), 4.42 (1H, t, J = 5Hz),
4.32 (1H, t, J = 5Hz), 3.06 (1H, t, J = 5Hz), 3.01 (1H, t, J = 5Hz),
2.95-2.90 (2H, m), 2.83 (2H, t, J = 8Hz), 2.58 (2H, t, J = 8Hz),
2.54 (2H, t, J = 6Hz), 2.19-2.12 (2H, m).

(Example 26)
2- (4-Fluorophenyl) -4- [1- [4- (N-phenylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-451)
The same reaction as in Example 19 was carried out using 4- (N-phenylsulfamoyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a slightly yellow powder. (Yield 52%).

Melting point: 210-211 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.34 (1H, br.s), 10.27-10.16 (1H, br.s), 8.44 (2H, d, J = 6Hz),
7.65 (2H, d, J = 8Hz), 7.38 (2H, d, J = 8Hz), 7.24-7.05 (10H, m),
6.99 (1H, t, J = 8Hz), 6.89 (1H, d, J = 3Hz), 5.25-5.21 (1H, m),
2.92-2.86 (2H, m), 2.77 (2H, t, J = 8Hz), 2.57-2.47 (4H, m),
2.16-2.09 (2H, m).

(Example 27)
2- (4-Fluorophenyl) -4- [1- [4- (N-methoxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-469)
The same reaction as in Example 19 was carried out using 4- (N-methoxysulfamoyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a pale yellow powder. (Yield 42%).

Melting point: 247-248 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.32 (1H, br.s), 10.52-10.32 (1H, br), 8.45 (2H, d, J = 6Hz),
7.73 (2H, d, J = 8Hz), 7.47 (2H, d, J = 8Hz), 7.19-7.08 (6H, m),
6.90 (1H, d, J = 3Hz), 5.28-5.23 (1H, m), 3.65 (3H, s), 2.95-2.90 (2H, m),
2.84 (2H, t, J = 8Hz), 2.59 (2H, t, J = 8Hz), 2.55 (2H, t, J = 6Hz), 2.18-2.12 (2H, m).

(Example 28)
4- [1- [4- (N, N-dimethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine -4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-442)
The same reaction as in Example 19 was carried out using 4- (N, N-dimethylsulfamoyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a white powder. (Yield 25%).

Melting point: 274-275 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.35 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.65 (2H, d, J = 8Hz),
7.50 (2H, d, J = 8Hz), 7.19-7.08 (6H, m), 6.90 (1H, d, J = 2Hz),
5.28-5.24 (1H, m), 2.96-2.91 (2H, m), 2.85 (2H, t, J = 8Hz),
2.60 (2H, t, J = 8Hz), 2.58 (6H, s), 2.55 (2H, t, J = 6Hz), 2.19-2.13 (2H, m).

(Example 29)
2- (4-Fluorophenyl) -4- [1- [4- [N- (2-methoxyethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- ( Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-459)
The reaction was conducted in the same manner as in Example 19 using 4- [N- (2-methoxyethyl) sulfamoyl] phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide. (Yield 43%).

Melting point: 235-236 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.34 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.69 (2H, d, J = 8Hz),
7.65-7.60 (1H, m), 7.43 (2H, d, J = 8Hz), 7.18-7.08 (6H, m),
6.90 (1H, d, J = 2Hz), 5.27-5.23 (1H, m), 3.28 (2H, t, J = 6Hz),
3.14 (3H, s), 2.94-2.90 (2H, m), 2.88 (2H, t, J = 6Hz), 2.82 (2H, t, J = 8Hz),
2.58 (2H, t, J = 8Hz), 2.54 (2H, t, J = 6Hz), 2.18-2.12 (2H, m).

(Example 30)
2- (4-Fluorophenyl) -4- [1- [4- [N- (2-hydroxyethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- ( Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-454)
The reaction was conducted in the same manner as in Example 19 using 4- [N- (2-hydroxyethyl) sulfamoyl] phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide. (Yield 27%).

Melting point: 270-271 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.35 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.69 (2H, d, J = 8Hz),
7.54-7.48 (1H, m), 7.43 (2H, d, J = 8Hz), 7.19-7.08 (6H, m),
6.92-6.89 (1H, m), 5.27-5.24 (1H, m), 4.69-4.65 (1H, m),
3.38-3.33 (2H, m), 2.95-2.90 (2H, m), 2.83 (2H, t, J = 8Hz),
2.76 (2H, t, J = 7Hz), 2.58 (2H, t, J = 8Hz), 2.55 (2H, t, J = 6Hz),
2.19-2.12 (2H, m).

(Example 31)
4- [1- [4- (2,2-dimethylhydrazinosulfonyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine -4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-476)
The same reaction as in Example 19 was carried out using 4- (2,2-dimethylhydrazinosulfonyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a yellow powder. (9% yield).

Melting point: 153-155 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.35 (1H, br.s), 8.57 (1H, s), 8.45 (2H, d, J = 6Hz),
7.72 (2H, d, J = 8Hz), 7.44 (2H, d, J = 8Hz), 7.18-7.08 (6H, s),
6.90 (1H, d, J = 3Hz), 5.26-5.23 (1H, m), 2.95-2.89 (2H, m),
2.87-2.80 (2H, m), 2.63-2.49 (4H, m), 2.22 (6H, s), 2.19-2.12 (2H, m).

(Example 32)
2- (4-Fluorophenyl) -3- (pyridin-4-yl) -4- [1- [4- [N- (pyridin-3-yl) methylsulfamoyl] phenethyl] -1,2,3 , 6-Tetrahydropyridin-4-yl] -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-453)
The title compound was treated in the same manner as in Example 19 using 4- [N- (pyridin-3-yl) methylsulfamoyl] phenethylbromide instead of 4- (N-methylsulfamoyl) phenethylbromide. Was obtained as a slightly yellow powder (yield 27%).

Melting point: 254-255 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.35 (1H, br.s), 8.46 (2H, d, J = 6Hz), 8.41 (1H, d, J = 3Hz),
8.20-8.13 (1H, m), 7.69 (2H, d, J = 8Hz), 7.61 (1H, d, J = 8Hz),
7.41 (2H, d, J = 8Hz), 7.28 (1H, dd, J = 8Hz, 3Hz), 7.19-7.08 (7H, m),
6.91 (1H, d, J = 3Hz), 5.28-5.25 (1H, m), 4.02 (2H, s),
2.96-2.91 (2H, m), 2.82 (2H, t, J = 8Hz), 2.58 (2H, t, J = 8Hz),
2.56 (2H, t, J = 6Hz), 2.20-2.13 (2H, m).

(Example 33)
4- [1- [4- [N- (2-dimethylaminoethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (Pyridin-4-yl) -1H-pyrrole dihydrochloride (Exemplified Compound No. 1-463)
The same reaction as in Example 19 was carried out using 4- [N- (2-dimethylaminoethyl) sulfamoyl] phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide (provided that 2 equivalents of 1N hydrochloric acid were used) To give the title compound as a pale yellow powder (yield 37%).

Melting point: 197-198 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, CDCl ₃ ) δ ppm:
8.49 (2H, d, J = 6Hz), 8.27-8.22 (1H, br.s), 7.80 (2H, d, J = 8Hz),
7.35 (2H, d, J = 8Hz), 7.28-7.24 (1H, br.s), 7.19 (2H, d, J = 6Hz),
7.14 (2H, dd, J = 9Hz, 4Hz), 6.98 (2H, t, J = 9Hz), 6.85 (1H, d, J = 3Hz),
5.50-5.46 (1H, m), 3.11-3.06 (2H, m), 2.97 (2H, t, J = 6Hz),
2.94-2.89 (2H, m), 2.71-2.62 (4H, m), 2.34-2.27 (4H, m), 2.07 (6H, s).

(Example 34)
4- [1- [4- [N- (1,3-dihydroxypropan-2-yl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluoro Phenyl) -3- (pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-455)
The same reaction as in Example 19 was carried out using 4- [N- (1,3-dihydroxypropan-2-yl) sulfamoyl] phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide. Was obtained as a pale yellow powder (yield 35%).

Melting point: 261-262 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.34 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.73 (2H, d, J = 8Hz),
7.40 (2H, d, J = 8Hz), 7.38-7.31 (1H, m), 7.19-7.08 (6H, m),
6.91 (1H, d, J = 2Hz), 5.28-5.24 (1H, m), 4.53 (2H, br.t, J = 5Hz),
3.31-3.27 (4H, m), 3.06-2.99 (1H, m), 2.95-2.90 (2H, m),
2.82 (2H, t, J = 8Hz), 2.58 (2H, t, J = 8Hz), 2.55 (2H, t, J = 6Hz),
2.19-2.12 (2H, m).

(Example 35)
4- [1- [4- (N-ethoxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4 -Yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-470)
The same reaction as in Example 19 was carried out using 4- (N-ethoxysulfamoyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a pale yellow powder. (Yield 49%).

Melting point: 217-218 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.33 (1H, br.s), 10.31-10.22 (1H, br.s), 8.45 (2H, d, J = 6Hz),
7.74 (2H, d, J = 8Hz), 7.47 (2H, d, J = 8Hz), 7.19-7.07 (6H, m),
6.90 (1H, d, J = 3Hz), 5.27-5.23 (1H, m), 3.89 (2H, quartet, J = 7Hz),
2.96-2.89 (2H, m), 2.84 (2H, t, J = 8Hz), 2.59 (2H, t, J = 8Hz),
2.55 (2H, t, J = 6Hz), 2.19-2.12 (2H, m), 1.09 (3H, t, J = 7Hz).

(Example 36)
4- [1- [4- (N-benzyloxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine- 4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-473)
The same reaction as in Example 19 was carried out using 4- (N-benzyloxysulfamoyl) phenethyl bromide in place of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a pale yellow powder. (9% yield).

Melting point: 237-238 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.34 (1H, br.s), 10.44-10.37 (1H, br.s), 8.45 (2H, d, J = 6Hz),
7.76 (2H, d, J = 8Hz), 7.46 (2H, d, J = 8Hz), 7.39-7.29 (5H, m),
7.19-7.08 (6H, m), 6.89 (1H, d, J = 2Hz), 5.26-5.23 (1H, m),
4.88 (2H, s), 2.94-2.88 (2H, m), 2.83 (2H, t, J = 8Hz), 2.58 (2H, t, J = 8Hz),
2.54 (2H, t, J = 6Hz), 2.17-2.11 (2H, m).

(Example 37)
4- [1- [4- (N-allyloxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine- 4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-472)
The same reaction as in Example 19 was carried out using 4- (N-allyloxysulfamoyl) phenethyl bromide instead of 4- (N-methylsulfamoyl) phenethyl bromide to obtain the title compound as a pale yellow powder. (Yield 23%).

Melting point: 239-240 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.34 (1H, br.s), 10.40-10.32 (1H, br.s), 8.45 (2H, d, J = 6Hz),
7.74 (2H, d, J = 8Hz), 7.47 (2H, d, J = 8Hz), 7.18-7.08 (6H, m),
6.90 (1H, d, J = 2Hz), 5.91-5.81 (1H, m), 5.29-5.17 (3H, m),
4.35 (2H, d, J = 6Hz), 2.95-2.90 (2H, m), 2.84 (2H, t, J = 8Hz),
2.59 (2H, t, J = 8Hz), 2.54 (2H, t, J = 6Hz), 2.18-2.12 (2H, m).

(Example 38)
2- (4-Fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) -β-oxophenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1290)
The same reaction as in Example 1 was carried out using α-bromo-4- (N-methylsulfamoyl) acetophenone instead of 4-ethoxycarbonylphenethyl bromide, and 2- (4-fluorophenyl) -4- [1 -[4- (N-methylsulfamoyl) -β-oxophenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole is obtained. It was. This was converted to the monohydrochloride in the same manner as in Example 19 to obtain the title compound as a yellow powder (yield 85%).

Melting point: 223-224 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.35 (1H, br.s), 8.44 (2H, d, J = 6Hz), 8.16 (2H, d, J = 8Hz),
7.90 (2H, d, J = 8Hz), 7.64 (1H, quartet, J = 5Hz), 7.19-7.08 (6H, m),
6.91 (1H, d, J = 3Hz), 5.27-5.23 (1H, m), 3.93 (2H, s),
3.04-2.99 (2H, m), 2.64 (2H, t, J = 6Hz), 2.44 (3H, d, J = 5Hz),
2.19-2.13 (2H, m).

(Example 39)
(±) -2- (4-Fluorophenyl) -4- [1- [β-hydroxy-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl ] -3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1284)
2- (4-Fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) -β-oxophenethyl] -1,2,3,6-tetrahydropyridine-4 obtained in Example 38 -Il] -3- (pyridin-4-yl) -1H-pyrrole (free form) 763 mg (1.44 mmol) was suspended in a mixture of methanol 15 ml and tetrahydrofuran 15 ml, and sodium borohydride 57 mg (1.44 mmol) was added and stirred at room temperature for 1 hour. 50 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained solid was washed with a small amount of ethyl acetate to obtain the free form of the title compound, and then 648 mg of the title compound (monohydrochloride) was obtained as a slightly yellow powder in the same manner as in Example 19 ( Yield 79%).

Melting point: 184-185 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.34 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.72 (2H, d, J = 8Hz),
7.55 (2H, d, J = 8Hz), 7.38 (1H, quartet, J = 5Hz), 7.19-7.09 (6H, m),
6.90 (1H, d, J = 3Hz), 5.27 (1H, d, J = 5Hz), 5.26-5.23 (1H, m),
4.83-4.77 (1H, m), 3.01-2.95 (2H, m), 2.64-2.52 (3H, m),
2.46 (1H, dd, J = 13Hz, 5Hz), 2.39 (3H, d, J = 5Hz), 2.17-2.11 (2H, m).

(Example 40)
2- (4-Fluorophenyl) -4- [1- (4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H- Pyrrole (Exemplary Compound No. 1-426)
2- (4-Fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole 479 mg (1.5 mmol) and 4- Dissolve 357 mg (1.8 mmol) of methanesulfonylphenylacetaldehyde in 10 ml of methanol, add 0.2 ml (3.6 mmol) of acetic acid, add 226 mg (3.6 mmol) of sodium cyanoborohydride under ice-cooling and stir at the same temperature. The mixture was stirred for 30 minutes and further at room temperature for 30 minutes, and the reaction solution was concentrated under reduced pressure. Water was added to the residue, and the precipitated solid was collected by filtration, washed with diethyl ether and then with methanol to obtain 291 mg of the title compound as a white powder (yield 39%).

Melting point: 239-241 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
8.49 (2H, d, J = 6Hz), 8.25 (1H, br.s), 7.87 (2H, d, J = 8Hz),
7.42 (2H, d, J = 9Hz), 7.19 (2H, d, J = 6Hz), 7.14 (2H, dd, J = 9, 5Hz),
6.98 (2H, t, J = 9Hz), 6.85 (1H, d, J = 3Hz), 5.48 (1H, br.s),
3.11-3.09 (2H, m), 3.05 (3H, s), 2.95 (2H, dd, J = 9Hz, 6Hz),
2.72 (2H, dd, J = 9Hz, 6Hz), 2.67 (2H, t, J = 6Hz), 2.31 (2H, br.s).

(Example 41)
2- (3-Chloro-4-fluorophenyl) -4- [1- (4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl ) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-545)
Instead of 2- (4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, 2- (3-chloro -4-Fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole was used for the same reaction as in Example 40. 2- (3-Chloro-4-fluorophenyl) -4- [1- (4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4) -Yl) -1H-pyrrole was obtained. This was then converted to the monohydrochloride in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (yield 61%).

Melting point: 225-230 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.49 (1H, s), 8.50 (2H, d, J = 7Hz), 7.83 (2H, d, J = 8Hz),
7.49 (2H, d, J = 9Hz), 7.35-7.28 (2H, m), 7.16 (2H, d, J = 6Hz),
7.05-7.01 (1H, m), 6.96 (1H, d, J = 3Hz), 5.25 (1H, s), 3.18 (3H, s),
2.92 (2H, br.s), 2.85 (2H, t, J = 7Hz), 2.61-2.50 (4H, m), 2.15 (2H, br.s).

(Example 42)
(±) -2- (4-Fluorophenyl) -4- [1- (4-methanesulfinylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole (Exemplified Compound No. 1-417)
The same reaction as in Example 1 was carried out using (±) -4-methanesulfinylphenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide to obtain the title compound as a pale pink powder (yield 73%).

Melting point: 207-209 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.38 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.58 (2H, d, J = 8Hz),
7.43 (2H, d, J = 8Hz), 7.20-7.07 (6H, m), 6.90 (1H, d, J = 2Hz),
5.28-5.23 (1H, m), 2.97-2.88 (2H, m), 2.85-2.77 (2H, m),
2.71 (3H, s), 2.62-2.50 (4H, m), 2.20-2.12 (2H, m).

(Example 43)
2- (4-Fluorophenyl) -4- [1- (4-methanesulfonyl-β-oxophenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl ) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1308)
The same reaction as in Example 1 was carried out using α-bromo-4-methanesulfonylacetophenone instead of 4-ethoxycarbonylphenethyl bromide to give 2- (4-fluorophenyl) -4- [1- (4-methanesulfonyl). -Β-oxophenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole was obtained. This was converted to the monohydrochloride in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (yield 75%).

Melting point: 183-184 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.39-11.34 (1H, br.s), 8.44 (2H, d, J = 6Hz), 8.19 (2H, d, J = 8Hz),
8.06 (2H, d, J = 8Hz), 7.19-7.07 (6H, m), 6.91 (1H, d, J = 3Hz),
5.27-5.23 (1H, m), 3.94 (2H, s), 3.29 (3H, s), 3.04-2.99 (2H, m),
2.64 (2H, t, J = 6Hz), 2.19-2.12 (2H, m).

(Example 44)
(±) -2- (4-Fluorophenyl) -4- [1- (β-hydroxy-4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine -4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1302)
2- (4-Fluorophenyl) -4- [1- (4-methanesulfonyl-β-oxophenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- obtained in Example 43 The same reaction as in Example 39 was carried out using (pyridin-4-yl) -1H-pyrrole (free form) to obtain the title compound as a slightly yellow powder (yield 77%).

Melting point: 271-272 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.34 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.87 (2H, d, J = 8Hz),
7.60 (2H, d, J = 8Hz), 7.19-7.08 (6H, m), 6.90 (1H, d, J = 3Hz),
5.32 (1H, d, J = 4Hz), 5.26-5.23 (1H, m), 4.85-4.80 (1H, m),
3.19 (3H, s), 3.00-2.95 (2H, m), 2.65-2.43 (4H, m), 2.18-2.10 (2H, m).

(Example 45)
(±) -2- (3-Chloro-4-fluorophenyl) -4- [1- (4-methanesulfinylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine -4yl) -1H-pyrrole (Exemplified Compound No. 1-536)
Instead of 4-ethoxycarbonylphenethyl bromide, (±) -4-methanesulfinylphenethyl bromide is replaced with 2- (4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6). 2-Tetrahydropyridin-4-yl) -1H-pyrrole instead of 2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydro The same reaction as in Example 1 was performed using pyridin-4-yl) -1H-pyrrole to obtain the title compound as a pale pink powder (yield 37%).

Melting point: 180-182 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.50 (1H, br.s), 8.49 (2H, d, J = 6Hz), 7.58 (2H, d, J = 8Hz),
7.42 (2H, d, J = 8Hz), 7.36-7.27 (2H, m), 7.16 (2H, d, J = 6Hz),
7.06-7.00 (1H, m), 6.90 (1H, d, J = 2Hz), 5.25 (1H, s), 2.95-2.89 (2H, m),
2.84-2.77 (2H, m), 2.61-2.52 (4H, m), 2.71 (3H, s), 2.19-2.12 (2H, m).

(Example 46)
(±) -2- (3-Chloro-4-fluorophenyl) -4- [1- (4-methanesulfinyl-β-oxophenethyl) -1,2,3,6-tetrahydropyridin-4-yl]- 3- (Pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 1-1326)
Instead of 4-ethoxycarbonylphenethyl bromide, (±) -α-bromo-4-methanesulfinylacetophenone is replaced with 2- (4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2, Instead of 3,6-tetrahydropyridin-4-yl) -1H-pyrrole, 2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,3) 6-Tetrahydropyridin-4-yl) -1H-pyrrole was used to carry out the same reaction as in Example 1 to obtain the title compound as a fine brown powder (yield 16%).

Melting point: 190-192 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.52-11.48 (1H, br.s), 8.48 (2H, d, J = 6Hz), 8.14 (2H, d, J = 8Hz),
7.81 (2H, d, J = 8Hz), 7.36-7.28 (2H, m), 7.16 (2H, d, J = 6Hz),
7.05-7.01 (1H, m), 6.96 (1H, d, J = 3Hz), 5.26-5.23 (1H, m),
3.92 (2H, s), 3.02-2.99 (2H, m), 2.80 (3H, s), 2.64 (2H, t, J = 6Hz),
2.18-2.13 (2H, m).

(Example 47)
4- [1- (4-Acetylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-527)
Instead of 4-ethoxycarbonylphenethyl bromide, 4-acetylphenethyl bromide was replaced with 2- (4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridine-4. -Yl) -1H-pyrrole instead of 2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) ) -1H-pyrrole was used to carry out the same reaction as in Example 1, and 4- [1- (4-acetylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (3 -Chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole was obtained. This was then converted to the monohydrochloride in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (yield 34%).

Melting point: 254-255 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.52-11.48 (1H, br.s), 8.49 (2H, d, J = 6Hz), 7.87 (2H, d, J = 8Hz),
7.39-7.28 (4H, m), 7.16 (2H, d, J = 6Hz), 7.06-7.01 (1H, m),
6.97-6.94 (1H, m), 5.27-5.23 (1H, m), 2.94-2.90 (2H, m),
2.81 (2H, t, J = 8Hz), 2.61-2.51 (7H, m), 2.18-2.12 (2H, m).

(Example 48)
2- (3-Chloro-4-fluorophenyl) -4-[(2S, 8aS) -2- (4-methoxycarbonylphenyl) -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-478)
a) 4-Bromo-1- (t-butyl) diphenylsilyl-2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole 3.24 g (5.49 mmol) Was dissolved in 65 ml of tetrahydrofuran, and 3.85 ml (6.04 mmol) of a 1.57 M butyllithium / hexane solution was added dropwise at −78 ° C., followed by stirring at the same temperature for 15 minutes. Separately prepared (2S, 8aS) -2- (4-methoxycarbonylphenyl) -1,2,3,5,6,7,8,8a-octahydroindolizin-7-one was added to this reaction solution. 17 ml of a tetrahydrofuran solution containing 50 g (5.49 mmol) and 0.26 g (6.04 mmol) of lithium chloride was slowly added dropwise at −78 ° C. and stirred at the same temperature for 1 hour.
b) 0.78 ml (12.08 mmol) of methanesulfonic acid, 65 ml of dichloromethane, 1.78 ml (22 mmol) of pyridine, 0.80 ml (11 mmol) of thionyl chloride and 6.5 ml (22 mmol) of methanol were sequentially added to the reaction solution and then cooled. The bath was removed and stirring was continued until room temperature was restored. The solvent was distilled off under reduced pressure, and the residue was dissolved in 200 ml of tetrahydrofuran and 200 ml of methanol. 55 ml (55 mmol) of 1M tetrabutylammonium fluoride / tetrahydrofuran solution was added and stirred at room temperature for 15 minutes. The solvent was distilled off, and the residue was extracted with 100 ml of ethyl acetate and 50 ml of water. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; ethyl acetate: methanol: isopropylamine = 20: 1: 1) to obtain 1.13 g of the title compound as a brown powder (total yield 39%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.56-11.50 (1H, br.s), 8.50 (2H, d, J = 6Hz), 7.87 (2H, d, J = 8Hz),
7.42 (2H, d, J = 8Hz), 7.36 (1H, d, J = 8Hz), 7.32 (1H, t, J = 9Hz),
7.18 (2H, d, J = 6Hz), 7.08-7.03 (1H, m), 7.01 (1H, d, J = 3Hz),
5.22-5.18 (1H, m), 3.83 (3H, s), 3.55-3.49 (1H, m),
3.47-3.39 (1H, m), 3.26-3.19 (1H, m), 2.92-2.85 (1H, m),
2.77-2.68 (1H, m), 2.64 (1H, dd, J = 10Hz, 7Hz), 2.35-2.25 (1H, m),
2.11-2.03 (1H, m), 1.90-1.82 (1H, m), 1.80-1.72 (1H, m).

(Example 49)
4-[(2S, 8aS) -2- (4-carboxyphenyl) -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (3-chloro-4-fluoro Phenyl) -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-477)
4- [1- (4-Ethoxycarbonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H- 2- (3-Chloro-4-fluorophenyl) -4-[(2S, 8aS) -2- (4-methoxycarbonylphenyl) -1,2,3,5, obtained in Example 48 instead of pyrrole 6,8a-Hexahydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole was used to carry out the same reaction as in Example 4 to obtain the title compound as a brown powder ( Yield 92%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.64-11.58 (1H, br.s), 8.51 (2H, d, J = 6Hz), 7.88 (2H, d, J = 8Hz),
7.42 (2H, d, J = 8Hz), 7.37 (1H, d, J = 8Hz), 7.32 (1H, t, J = 9Hz),
7.21 (2H, d, J = 6Hz), 7.09-7.02 (2H, m), 5.19-5.13 (1H, m),
3.86-3.74 (1H, m), 3.49 (1H, quintet, J = 8Hz), 3.38 (1H, t, J = 10Hz),
3.09-3.00 (1H, m), 2.97-2.84 (2H, m), 2.46-2.35 (1H, m),
2.27-2.16 (1H, m), 2.01-1.90 (1H, m), 1.87-1.77 (1H, m).

(Example 50)
2- (3-Chloro-4-fluorophenyl) -4-[(2S, 8aS) -2- (4-carbamoylphenyl) -1,2,3,5,6,8a-hexahydroindolizine-7- Yl] -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-485)
4- [1- (4-Carboxyphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole 4-[(2S, 8aS) -2- (4-carboxyphenyl) -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2 obtained in Example 49 instead of -(3-Chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole was reacted in the same manner as in Example 5 using ammonia gas instead of methylamine to give the title compound Was obtained as a brown powder (yield 71%).

Melting point: 215-217 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.55-11.49 (1H, br.s), 8.49 (2H, d, J = 6Hz), 7.90-7.84 (1H, br.s),
7.78 (2H, d, J = 8Hz), 7.36 (1H, dd, J = 7Hz, 2Hz), 7.34-7.28 (3H, m),
7.27-7.22 (1H, br.s), 7.18 (2H, d, J = 6Hz), 7.07-7.02 (1H, m),
7.00 (1H, d, J = 2Hz), 5.22-5.18 (1H, m), 3.54-3.47 (1H, m),
3.39 (1H, quintet, J = 8Hz), 3.20 (1H, t, J = 9Hz), 2.92-2.84 (1H, m),
2.75-2.67 (1H, m), 2.62 (1H, dd, J = 10Hz, 8Hz), 2.34-2.25 (1H, m),
2.10-2.02 (1H, m), 1.89-1.81 (1H, m), 1.79-1.70 (1H, m).

(Example 51)
2- (3-Chloro-4-fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-methylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydro Indolizine-7-yl] -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-486)
The same reaction as in Example 50 was performed using methylamine instead of ammonia gas to obtain the title compound as a light brown powder (yield 71%).

Melting point: 176-178 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.56-11.48 (1H, br.s), 8.49 (2H, d, J = 6Hz), 8.35-8.31 (1H, m),
7.73 (2H, d, J = 8Hz), 7.38-7.27 (4H, m), 7.17 (2H, d, J = 6Hz),
7.02 (1H, m), 7.00 (1H, d, J = 2Hz), 5.22-5.18 (1H, m), 3.54-3.46 (1H, m),
3.38 (1H, quintet, J = 8Hz), 3.20 (1H, t, J = 9Hz), 2.91-2.84 (1H, m),
2.76-2.67 (4H, m), 2.62- (1H, dd, J = 10Hz, 3Hz), 2.34-2.24 (1H, m),
2.10-2.01 (1H, m), 1.89-1.81 (1H, m), 1.78-1.71 (1H, m).

(Example 52)
4-[(2S, 8aS) -2- (4-carbamoylphenyl) -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4-fluorophenyl) -3 -(Pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-366)
4-bromo-1- (t-butyl) diphenylsilyl-2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole instead of 4-bromo-1- ( t-butyl) diphenylsilyl-2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole was used to carry out the same reaction as in Examples 48 and 49, and 4-[(2S, 8aS) -2- (4-Carboxyphenyl) -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4-fluorophenyl) -3- (pyridine-4- Yl) -1H-pyrrole, which is then converted to 4-[(2S, 8aS) -2- (4-carboxyphenyl) -1,2,3,5,6,8a-hexahydroindolizine-7. -Yl] -2- (3-chloro-4- Ruorofeniru) -3- (The same reaction as in Example 50 using, instead of 4-yl)-1H-pyrrole to afford the title compound as a pale brown powder (66% yield).

Melting point: 247-250 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.42-11.36 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.90-7.82 (1H, br.s),
7.77 (2H, d, J = 8Hz), 7.32 (2H, d, J = 8Hz), 7.26-7.20 (1H, br.s),
7.19-7.08 (6H, m), 6.95 (1H, d, J = 3Hz), 5.22-5.19 (1H, m),
3.54-3.58 (1H, m), 3.44-3.35 (1H, m), 3.24-3.27 (1H, m),
2.91-2.85 (1H, m), 2.75-2.68 (1H, m), 2.65-2.59 (1H, m),
2.34-2.26 (1H, m), 2.10-2.02 (1H, m), 1.89-1.82 (1H, m),
1.79-1.72 (1H, m).

  The same reaction as in Example 52 was performed using various amines instead of ammonia, and the compounds of Examples 53 to 61 were synthesized.

(Example 53)
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-methylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-367)
Light brown powder (69% yield)
Melting point: 171-173 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.43-11.36 (1H, br.s), 8.45 (2H, d, J = 6Hz), 8.35-8.30 (1H, m),
7.73 (2H, d, J = 8Hz), 7.33 (2H, d, J = 8Hz), 7.21-7.07 (6H, m),
6.95 (1H, d, J = 3Hz), 5.22-5.18 (1H, m), 3.54-3.47 (1H, m),
3.39 (1H, quintet, J = 8Hz), 3.21 (1H, t, J = 9Hz), 2.91-2.84 (1H, m),
2.76 (3H, d, J = 4Hz), 2.75-2.67 (1H, m), 2.62 (1H, dd, J = 10Hz, 8Hz),
2.34-2.26 (1H, m), 2.10-2.02 (1H, m), 1.89-1.81 (1H, m), 1.80-1.72 (1H, m).

(Example 54)
4-[(2S, 8aS) -2- [4- (N-ethylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4- Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-368)
Light brown powder (59% yield)
Melting point: 178-180 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.43-11.37 (1H, br.s), 8.45 (2H, d, J = 6Hz), 8.38-8.33 (1H, m),
7.74 (2H, d, J = 8Hz), 7.33 (2H, d, J = 8Hz), 7.20-7.08 (6H, m),
6.97-6.93 (1H, m), 5.22-5.19 (1H, m), 3.54-3.47 (1H, m),
3.44-3.35 (1H, m), 3.30-3.18 (3H, m), 2.92-2.84 (1H, m),
2.75-2.67 (11H, m), 2.62 (1H, dd, J = 10Hz, 8Hz), 2.35-2.26 (1H, m),
2.10-2.02 (1H, m), 1.89-1.81 (1H, m), 1.80-1.71 (1H, m),
1.11 (3H, t, J = 7Hz).

(Example 55)
4-[(2S, 8aS) -2- [4- (N-benzylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4- Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-372)
Light brown powder (72% yield)
Melting point: 173-175 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.42-11.37 (1H, br.s), 8.05 (1H, t, J = 6Hz), 8.45 (2H, d, J = 6Hz),
7.81 (2H, d, J = 8Hz), 7.35 (2H, d, J = 8Hz), 7.33-7.09 (1H, m),
6.95 (1H, d, J = 2Hz), 5.22-5.19 (1H, m), 4.46 (2H, d, J = 6Hz),
3.55-3.48 (1H, m), 3.41 (1H, quintet, J = 8Hz), 3.22 (1H, t, J = 9Hz),
2.92-2.85 (1H, m), 2.75-2.68 (1H, m), 2.66-2.60 (1H, m),
2.35-2.26 (1H, m), 2.10-2.02 (1H, m), 1.90-1.82 (1H, m),
1.80-1.72 (1H, m).

(Example 56)
4-[(2S, 8aS) -2- [4- (N-cyclopropylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4 -Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-374)
Light brown powder (38% yield)
Melting point: 200-202 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.44-11.36 (1H, br.s), 8.45 (2H, d, J = 6Hz), 8.15 (1H, d, J = 4Hz),
7.72 (2H, d, J = 8Hz), 7.32 (2H, d, J = 8Hz), 7.20-7.08 (6H, m),
6.95 (1H, d, J = 2Hz), 5.22-5.17 (1H, m), 3.54-3.47 (1H, m),
3.39 (1H, quintet, J = 8Hz), 3.24-3.17 (1H, m), 2.91-2.78 (2H, m),
2.75-2.67 (1H, m), 2.61 (1H, dd, J = 10Hz, 3Hz), 2.35-2.25 (1H, m),
2.11-2.01 (1H, m), 1.88-1.80 (1H, m), 1.80-1.71 (1H, m),
0.69-0.64 (2H, m), 0.57-0.52 (2H, m).

(Example 57)
4-[(2S, 8aS) -2- [4- [N- (2-fluoroethyl) carbamoyl] phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl]- 2- (4-Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-389)
Light brown powder (27% yield)
Melting point: 183-185 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.43-11.36 (1H, br.s), 8.60 (1H, t, J = 5Hz), 8.23 (2H, d, J = 6Hz),
7.78 (2H, d, J = 8Hz), 7.35 (2H, d, J = 8Hz), 7.20-7.09 (6H, m),
6.95 (1H, d, J = 3Hz), 5.24-5.18 (1H, m), 4.57 (1H, t, J = 5Hz),
4.47 (1H, t, J = 5Hz), 3.57 (1H, quartet, J = 5Hz), 3.52 (2H, quartet, J = 5Hz),
3.41 (1H, quintet, J = 8Hz), 3.25-3.19 (1H, m), 2.92-2.84 (1H, m),
2.76-2.67 (1H, m), 2.63 (1H, dd, J = 10Hz, 3Hz), 2.35-2.25 (1H, m),
2.10-2.02 (1H, m), 1.89-1.82 (1H, m), 1.81-1.72 (1H, m).

(Example 58)
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-propylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-369)
Light brown powder (yield 79%)
Melting point: 190-192 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.44-11.36 (1H, br.s), 8.46 (2H, d, J = 6Hz), 8.38-8.32 (1H, m),
7.75 (2H, d, J = 8Hz), 7.33 (2H, d, J = 8Hz), 7.21-7.09 (6H, m),
6.96 (1H, d, J = 3Hz), 5.23-5.19 (1H, m), 3.55-3.48 (1H, m),
3.46-3.36 (1H, m), 3.25-3.16 (3H, m), 2.93-2.85 (1H, m),
2.76-2.68 (1H, m), 2.63 (1H, dd, J = 10Hz, 3Hz),
2.37-2.26 (1H, m), 2.11-2.03 (1H, m), 1.90-1.82 (1H, m),
1.81-1.72 (1H, m), 1.56-1.47 (2H, m), 0.91-0.85 (3H, m).

(Example 59)
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-isopropylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-370)
Light brown powder (yield 79%)
Melting point: 202-204 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.44-11.37 (1H, br.s), 8.46 (2H, d, J = 6Hz), 8.10 (1H, d, J = 7Hz),
7.75 (2H, d, J = 8Hz), 7.33 (2H, d, J = 8Hz), 7.20-7.09 (6H, m),
6.96 (1H, d, J = 3Hz), 5.23-5.19 (1H, m), 4.08 (1H, octet, J = 7Hz),
3.55-3.48 (1H, m), 3.40 (1H, quintet, J = 8Hz), 3.32 (1H, t, J = 9Hz),
2.93-2.85 (1H, m), 2.76-2.68 (1H, m), 2.63 (1H, dd, J = 10Hz, 3Hz),
2.37-2.26 (1H, m), 2.11-2.02 (1H, m), 1.90-1.82 (1H, m),
1.81-1.72 (1H, m), 1.15 (6H, d, J = 7Hz).

(Example 60)
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- [N- (2-hydroxyethyl) carbamoyl] phenyl] -1,2,3,5,6,8a-hexa Hydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-385)
Light brown powder (52% yield)
Melting point: 189-191 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.44-11.38 (1H, br.s), 8.46 (2H, d, J = 6Hz), 8.36-8.31 (1H, m),
7.77 (2H, d, J = 8Hz), 7.34 (2H, d, J = 8Hz), 7.21-7.10 (6H, m),
6.96 (1H, d, J = 3Hz), 5.23-5.19 (1H, m), 4.73-4.68 (1H, m),
3.55-3.46 (3H, m), 3.41 (1H, quintet, J = 8Hz), 3.34-3.28 (2H, m),
3.22 (1H, t, J = 9Hz), 2.93-2.85 (1H, m), 2.76-2.68 (1H, m),
2.63 (1H, dd, J = 10Hz, 2Hz), 2.36-2.27 (1H, m), 2.11-2.03 (1H, m),
1.90-1.82 (1H, m), 1.81-1.73 (1H, m).

(Example 61)
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- [N- (2-methoxyethyl) carbamoyl] phenyl] -1,2,3,5,6,8a-hexa Hydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole (Exemplified Compound No. 7-390)
Light brown powder (66% yield)
Melting point: 166-168 ° C
¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
11.43-11.38 (1H, br.s), 8.46 (2H, d, J = 6Hz), 8.44-8.39 (1H, m),
7.76 (2H, d, J = 8Hz), 7.34 (2H, d, J = 8Hz), 7.21-7.09 (6H, m),
6.96 (1H, d, J = 2Hz), 5.23-5.20 (1H, m), 3.55-3.48 (1H, m),
3.47-3.37 (5H, m), 3.26 (3H, s), 3.25-3.19 (1H, m), 2.92-2.85 (1H, m),
2.76-2.68 (1H, m), 2.63 (1H, dd, J = 10Hz, 3Hz), 2.35-2.27 (1H, m),
2.11-2.02 (1H, m), 1.90-1.82 (1H, m), 1.81-1.73 (1H, m).

(Example 62)
(±) -4- [1- (β-Ethyl-4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine -4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1304)
The same reaction as in Example 40 was performed using (±) -α-ethyl-4-methanesulfonylphenylacetaldehyde instead of 4-methanesulfonylphenylacetaldehyde, and (±) -4- [1- (β-ethyl-4 -Methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole was obtained. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a yellow powder (yield 54%).

Melting point: 183-185 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.34 (1H, s), 8.44 (2H, d, J = 6Hz), 7.84 (2H, d, J = 9Hz), 7.48 (2H, d, J = 8Hz), 7.16-7.08 (6H, m), 6.88 (1H, d, J = 2Hz), 5.21 (1H, s), 3.20 (3H, s),
2.89-2.84 (3H, m), 2.56-2.43 (4H, m), 2.07 (2H, s), 1.80-1.73 (1H, m),
1.52-1.44 (1H, m), 0.70 (3H, t, J = 8Hz).

(Example 63)
(±) -2- (3-Chloro-4-fluorophenyl) -4- [1- (β-ethyl-4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl]- 3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1331)
Instead of 4-methanesulfonylphenylacetaldehyde, (±) -α-ethyl-4-methanesulfonylphenylacetaldehyde was replaced with 2- (4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrole instead of 2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3 , 6-Tetrahydropyridin-4-yl) -1H-pyrrole was reacted in the same manner as in Example 40 to obtain (±) -2- (3-chloro-4-fluorophenyl) -4- [1- (β -Ethyl-4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole was obtained. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a yellow powder (yield 10%).

Melting point: 183-185 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.48 (1H, d, J = 2Hz), 8.47 (2H, d, J = 6Hz), 7.83 (2H, d, J = 8Hz),
7.47 (2H, d, J = 8Hz), 7.33-7.27 (2H, m), 7.13 (2H, d, J = 6Hz),
7.03-6.99 (1H, m), 6.92 (1H, d, J = 2Hz), 5.20 (1H, s),
3.20 (3H, s), 2.91-2.78 (3H, m), 2.58-2.41 (4H, m), 2.06 (2H, s),
1.79-1.71 (1H, m), 1.53-1.44 (1H, m), 0.69 (3H, t, J = 7Hz).

(Example 64)
4- [1- [β, β-ethylene-4- (N-methylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl]- 3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplary Compound No. 1-1292)
The same reaction as in Example 40 was carried out using 1- [4- (N-methylsulfamoyl) phenyl] cyclopropane-1-carboxaldehyde instead of 4-methanesulfonylphenylacetaldehyde to give 4- [1- [β , Β-ethylene-4- (N-methylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4- Yl) -1H-pyrrole was obtained. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (yield 28%).

Melting point: 260-261 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.33-11.28 (1H, m), 8.42 (2H, d, J = 6Hz), 7.65 (2H, d, J = 8Hz),
7.51 (2H, d, J = 8Hz), 7.36-7.29 (1H, m), 7.17-7.06 (6H, m),
6.85 (1H, d, J = 2Hz), 5.23-5.19 (1H, m), 2.91-2.86 (2H, m),
2.62 (2H, s), 2.54 (2H, t, J = 6Hz), 2.41 (3H, s), 2.08-2.03 (2H, m),
0.92-0.88 (2H, m), 0.82-0.78 (2H, m).

(Example 65)
2- (3-Chloro-4-fluorophenyl) -4- [1- [β, β-ethylene-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridine-4 -Yl] -3- (pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1319)
Instead of 4-methanesulfonylphenylacetaldehyde, 1- [4- (N-methylsulfamoyl) phenyl] cyclopropane-1-carboxaldehyde is replaced with 2- (4-fluorophenyl) -3- (pyridin-4-yl). ) -4- (1,2,3,6-Tetrahydropyridin-4-yl) -1H-pyrrole instead of 2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl)- Using 4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, the same reaction as in Example 40 was performed, and 2- (3-chloro-4-fluorophenyl) -4- [ 1- [β, β-Ethylene-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H- Pillow I got it. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (yield 16%).

Melting point: 168-170 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.48-11.44 (1H, br.s), 8.46 (2H, d, J = 6Hz), 7.64 (2H, d, J = 8Hz),
7.50 (2H, d, J = 8Hz), 7.37-7.26 (3H, m), 7.12 (2H, d, J = 6Hz),
7.04-6.99 (1H, m), 6.91 (1H, d, J = 3Hz), 5.22-5.18 (1H, m),
2.91-2.85 (2H, m), 2.61 (2H, s), 2.53 (2H, t, J = 5Hz), 2.40 (3H, s),
2.08-2.02 (2H, m), 0.92-0.88 (2H, m), 0.82-0.78 (2H, m).

Example 66
(±) -2- (4-Fluorophenyl) -4- [1- [β-methyl-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl ] -3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1285)
The same reaction as in Example 40 was carried out using (±) -α-methyl-4- (N-methylsulfamoyl) phenylacetaldehyde instead of 4-methanesulfonylphenylacetaldehyde (±) -2- (4- Fluorophenyl) -4- [1- [β-methyl-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4- Yl) -1H-pyrrole was obtained. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a yellow powder (yield 37%).

Melting point: 175-177 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.69 (1H, s), 10.34 (1H, br.s), 8.49 (2H, d, J = 6H), 7.74 (2H, d, J = 9Hz),
7.59 (2H, d, J = 8Hz), 7.48-7.42 (1H, m), 7.36 (2H, d, J = 6Hz),
7.21-7.09 (4H, m), 7.06 (1H, d, J = 3Hz), 5.09 (1H, br.s),
3.78-2.55 (9H, m), 2.40 (3H, d, J = 5Hz), 1.34 (3H, m).

(Example 67)
(±) -2- (3-Chloro-4-fluorophenyl) -4- [1- [β-methyl-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridine -4-yl] -3- (pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-11312)
Instead of 4-methanesulfonylphenylacetaldehyde, (±) -α-methyl-4- (N-methylsulfamoyl) phenylacetaldehyde was replaced with 2- (4-fluorophenyl) -3- (pyridin-4-yl)- Instead of 4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, 2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- Using (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, the same reaction as in Example 40 was carried out (±) -2- (3-chloro-4-fluorophenyl) -4 -[1- [β-Methyl-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H- Obtained pyrrole. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a yellow powder (yield 15%).

Melting point: 177-179 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.85 (1H, s), 10.34 (1H, br.s), 8.54 (2H, d, J = 6Hz), 7.74 (2H, d, J = 8Hz),
7.63-7.53 (2H, m), 7.51-7.38 (4H, m), 7.33 (1H, t, J = 9Hz), 7.12 (1H, s),
7.10-7.02 (1H, m), 5.12 (0.5H, s), 5.09 (0.5H, s), 3.79-2.59 (9H, m),
2.44-2.36 (3H, m), 1.40-1.29 (3H, m).

Example 68
(±) -4- [1- [β-Ethyl-4- (N-methylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl ] -3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1286)
The same reaction as in Example 40 was performed using (±) -α-ethyl-4- (N-methylsulfamoyl) phenylacetaldehyde instead of 4-methanesulfonylphenylacetaldehyde, and (±) -4- [1- [Β-Ethyl-4- (N-methylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4- Yl) -1H-pyrrole was obtained. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a yellow powder (yield 46%).

Melting point: 168-171 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.34 (1H, s), 8.43 (2H, d, J = 7Hz), 7.68 (2H, d, J = 8Hz),
7.42 (2H, d, J = 8Hz), 7.35 (1H, s), 7.16-7.09 (6H, m), 6.87 (1H, d, J = 2Hz),
5.21 (1H, s), 3.32 (3H, s), 2.84 (3H, s), 2.54-2.44 (4H, m),
2.06 (2H, s), 1.81-1.72 (1H, m), 1.51-1.43 (1H, m), 0.69 (3H, t, J = 7Hz).

(Example 69)
(±) -2- (3-Chloro-4-fluorophenyl) -4- [1- [β-ethyl-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridine -4-yl] -3- (pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1313)
Instead of 4-methanesulfonylphenylacetaldehyde, (±) -α-ethyl-4- (N-methylsulfamoyl) phenylacetaldehyde was replaced with 2- (4-fluorophenyl) -3- (pyridin-4-yl)- Instead of 4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, 2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- Using (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, the same reaction as in Example 40 was carried out (±) -2- (3-chloro-4-fluorophenyl) -4 -[1- [β-Ethyl-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H- Obtained pyrrole. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a yellow powder (yield 35%).

Melting point: 165-168 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.43 (1H, d, J = 2Hz), 8.44 (2H, d, J = 6Hz), 7.66 (2H, d, J = 8Hz),
7.40 (2H, d, J = 8Hz), 7.34-7.25 (3H, m), 7.11 (2H, d, J = 6Hz),
7.02-6.98 (1H, m), 6.90 (1H, d, J = 2Hz), 5.19 (1H, s), 3.30 (3H, s),
2.83 (3H, s), 2.53-2.43 (4H, m), 2.06 (2H, s), 1.80-1.73 (1H, m),
1.50-1.43 (1H, m), 0.69 (3H, t, J = 7Hz).

(Example 70)
2- (4-Fluorophenyl) -4- [1- [2- [5- (N-methylsulfamoyl) thiophen-2-yl] ethyl] -1,2,3,6-tetrahydropyridine-4- Yl] -3- (pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 6-134)
The same reaction as in Example 1 was performed using 2- [5- (N-methylsulfamoyl) thiophen-2-yl] ethyl bromide instead of 4-ethoxycarbonylphenethyl bromide, and 2- (4-fluorophenyl) was obtained. ) -4- [1- [2- [5- (N-methylsulfamoyl) thiophen-2-yl] ethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine -4-yl) -1H-pyrrole was obtained. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (44% yield).

Melting point: 225-226 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum of free body (500 MHz, DMSO-d ₆ ) δ ppm:
11.40-11.35 (1H, br.s), 8.46 (2H, d, J = 6Hz), 7.53-7.48 (1H, br.s),
7.38 (1H, d, J = 4Hz), 7.19-7.09 (6H, m), 6.95 (1H, d, J = 4Hz),
6.93 (1H, d, J = 3Hz), 5.27-5.24 (1H, m), 3.02 (2H, t, J = 7Hz),
2.96-2.92 (2H, m), 2.60 (2H, t, J = 7Hz), 2.58 (2H, t, J = 6Hz),
2.48 (3H, s), 2.23-2.28 (2H, m).

(Example 71)
2- (4-Fluorophenyl) -4- [1- [4- (N-methoxycarbonylmethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine -4-yl) -1H-pyrrole (Exemplified Compound No. 1-465)
The same reaction as in Example 1 was carried out using 4- (N-methoxycarbonylmethylsulfamoyl) phenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide to obtain the title compound as a pale yellow powder (yield 23 %).

Melting point: 220-223 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.33 (1H, s), 8.42 (2H, d, J = 6Hz), 8.10 (1H, t, J = 6Hz), 7.65 (2H, d, J = 8Hz), 7.40 (2H, d, J = 9Hz) , 7.15-7.07 (6H, m), 6.88 (1H, d, J = 3Hz),
5.24 (1H, s), 3.67 (2H, d, J = 6Hz), 3.49 (3H, s), 2.92 (2H, s),
2.81 (2H, t, J = 7Hz), 2.59-2.52 (4H, m), 2.15 (2H, s).

(Example 72)
4- [1- [4- (N-carboxymethylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine- 4-yl) -1H-pyrrole (Exemplified Compound No. 1-464)
2- (4-Fluorophenyl) -4- [1- [4- (N-methoxycarbonylmethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl obtained in Example 71 ] -3- (Pyridin-4-yl) -1H-pyrrole was hydrolyzed in the same manner as in Example 4 to obtain the title compound as a pale yellow powder (yield 81%).

Melting point: 233-235 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.40 (1H, s), 8.43 (2H, d, J = 6Hz), 7.66 (2H, d, J = 9Hz), 7.39 (2H, d, J = 8Hz), 7.16-7.06 (6H, m), 6.88 (1H, d, J = 3Hz), 5.23 (1H, s), 3.08 (2H, s), 2.93 (2H, s), 2.83-2.79 (2H, m), 2.60-2.53 (4H, m), 2.15 (2H, s).

(Example 73)
4- [1- [4- (N-carbamoylmethylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine- 4-yl) -1H-pyrrole (Exemplified Compound No. 1-467)
The same reaction as in Example 1 was carried out using 4- (N-carbamoylmethylsulfamoyl) phenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide to obtain the title compound as a light brown powder (yield 15% ).

Melting point: 230-233 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.34 (1H, s), 8.42 (2H, d, J = 6Hz), 7.67 (2H, d, J = 8Hz), 7.40 (2H, d, J = 9Hz), 7.24 (1H, s), 7.15-7.07 (6H, m), 6.88 (1H, d, J = 3Hz), 5.24 (1H, s),
3.32 (2H, s), 2.92 (2H, s), 2.83-2.80 (2H, m), 2.59-2.53 (4H, m), 2.15 (2H, s).

(Example 74)
4- [1- [4- (N-cyanomethylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine- 4-yl) -1H-pyrrole (Exemplified Compound No. 1-457)
The same reaction as in Example 1 was carried out using 4- (N-cyanomethylsulfamoyl) phenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide to obtain the title compound as a pale yellow powder (yield 16% ).

Melting point: 196-199 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.36 (1H, s), 8.47 (1H, s), 8.45 (2H, d, J = 7Hz), 7.74 (2H, d, J = 8Hz),
7.47 (2H, d, J = 8Hz), 7.18-7.09 (6H, m), 6.90 (1H, d, J = 2Hz),
5.25 (1H, s), 4.07 (2H, s), 2.92 (2H, d, J = 3Hz), 2.84 (2H, t, J = 8Hz),
2.60-2.53 (4H, m), 2.15 (2H, s).

(Example 75)
4- [1- [3-Fluoro-4- (N-methylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 2-1)
The same reaction as in Example 1 was performed using 3-fluoro-4- (N-methylsulfamoyl) phenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide, and 4- [1- [3-fluoro-4- (N-methylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole Obtained. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a light brown powder (yield 48%).

Melting point: 239-241 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.38 (1H, br.s), 8.45 (2H, d, J = 7Hz), 7.69-7.59 (2H, m),
7.35 (1H, dd, J = 12Hz, 1Hz), 7.24 (1H, dd, J = 8Hz, 1Hz), 7.19-7.08 (6H, m),
6.90 (1H, d, J = 3Hz), 5.28-5.22 (1H, m), 2.97-2.89 (2H, m),
2.87-2.79 (2H, m), 2.64-2.50 (4H, m), 2.48 (3H, s), 2.21-2.12 (2H, m).

(Example 76)
4- [1- [3-Chloro-4- (N-methylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 2-2)
The same reaction as in Example 1 was carried out using 3-chloro-4- (N-methylsulfamoyl) phenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide, and 4- [1- [3-chloro-4- (N-methylsulfamoyl) phenethyl] -2- (4-fluorophenyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole Obtained. This was then converted to the monohydrochloride in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (yield 8%).

Melting point: 229-231 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.33 (1H, br.s), 8.42 (2H, d, J = 6Hz), 7.81 (1H, d, J = 8Hz),
7.59-7.54 (1H, m), 7.53 (1H, d, J = 2Hz), 7.37 (1H, dd, J = 8Hz, 2Hz),
7.17-7.06 (6H, m), 6.89 (1H, d, J = 2Hz), 5.23 (1H, br.s),
2.93-2.88 (2H, m), 2.84-2.78 (2H, m), 2.62-2.51 (4H, m),
2.45 (3H, d, J = 5Hz), 2.17-2.12 (2H, m).

(Example 77)
2- (4-Fluorophenyl) -4- [1- [3-methyl-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 2-4)
The same reaction as in Example 1 was performed using 3-methyl-4- (N-methylsulfamoyl) phenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide, and 2- (4-fluorophenyl) -4- [ 1- [3-Methyl-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole Obtained. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (yield 55%).

Melting point: 192-194 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.33 (1H, br.s), 8.43 (2H, d, J = 6Hz), 7.66 (1H, d, J = 8Hz),
7.37-7.31 (1H, m), 7.23 (1H, s), 7.20 (1H, d, J = 8Hz),
7.16-7.06 (6H, m), 6.89 (1H, d, J = 3Hz), 5.24 (1H, br.s),
2.94-2.89 (2H, m), 2.79-2.73 (2H, m), 2.60-2.50 (4H, m),
2.51 (3H, s), 2.39 (3H, d, J = 5Hz), 2.18-2.12 (2H, m).

(Example 78)
2- (4-Fluorophenyl) -4- [1- [3-methoxy-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 2-3)
The same reaction as in Example 1 was carried out using 3-methoxy-4- (N-methylsulfamoyl) phenethyl bromide instead of 4-ethoxycarbonylphenethyl bromide, and 2- (4-fluorophenyl) -4- [ 1- [3-methoxy-4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole Obtained. This was then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (yield 74%).

Melting point: 245-247 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.37 (1H, br.s), 8.45 (2H, d, J = 6Hz), 7.59 (1H, d, J = 8Hz),
7.19-7.08 (7H, m), 6.95-6.88 (3H, m), 5.28-5.23 (1H, m),
3.87 (3H, s), 2.97-2.91 (2H, m), 2.83-2.77 (2H, m),
2.64-2.51 (4H, m), 2.37 (3H, d, J = 5Hz), 2.21-2.12 (2H, m).

(Example 79)
2- (3-Chloro-4-fluorophenyl) -4- [1- [4- (2-methoxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- ( Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplified Compound No. 1-1346)

Instead of 4-ethoxycarbonylphenethyl bromide, 4- (2-methoxyethyl) sulfonylphenethyl bromide was replaced with 2- (4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3, 2- (3-Chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-) instead of 6-tetrahydropyridin-4-yl) -1H-pyrrole Using tetrahydropyridin-4-yl) -1H-pyrrole, the same reaction as in Example 1 was carried out to give 2- (3-chloro-4-fluorophenyl) -4- [1- [4- (2-methoxyethyl). ) Sulfonylsulfonyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole. This was then converted to the monohydrochloride in the same manner as in Example 19 to obtain the title compound as a pale yellow powder (yield 50%).

Melting point: 208-210 ° C (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.50 (1H, br.s), 8.48 (2H, d, J = 6Hz), 7.78 (2H, d, J = 8Hz),
7.48 (2H, d, J = 8Hz), 7.36-7.27 (2H, m), 7.15 (2H, d, J = 6Hz),
7.05-7.00 (1H, m), 6.95 (1H, d, J = 3Hz), 5.27-5.22 (1H, m),
3.62-3.53 (4H, m), 3.09 (3H, s), 2.95-2.88 (2H, m),
2.88-2.82 (2H, m), 2.63-2.50 (4H, m), 2.18-2.12 (2H, m).

(Example 80)
2- (3-Chloro-4-fluorophenyl) -4- [1- [4- (2-hydroxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- ( Pyridin-4-yl) -1H-pyrrole monohydrochloride (Exemplary Compound No. 1-1347)
1) Instead of 4-ethoxycarbonylphenethyl bromide, 4- [2- (tetrahydropyran-2-yloxy) ethyl] sulfonylphenethyl bromide is replaced with 2- (4-fluorophenyl) -3- (pyridin-4-yl)- Instead of 4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, 2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- Using (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole, the same reaction as in Example 1 was carried out to give 2- (3-chloro-4-fluorophenyl) -3- (pyridine -4-yl) -4- [1- [4- [2- (tetrahydropyran-2-yloxy) ethyl] sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl]- The H- pyrrole as a pale brown powder (yield 37%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.50 (1H, br.s), 8.49 (2H, d, J = 7Hz), 7.79 (2H, d, J = 8Hz),
7.48 (2H, d, J = 8Hz), 7.36-7.27 (2H, m), 7.15 (2H, d, J = 7Hz),
7.05-7.00 (1H, m), 6.95 (1H, d, J = 3Hz), 5.27-5.22 (1H, m),
4.46-4.42 (1H, m), 3.90-3.81 (1H, m), 3.67-3.52 (4H, m),
3.38-3.28 (1H, m), 2.94-2.88 (2H, m), 2.88-2.80 (2H, m),
2.61-2.48 (4H, m), 2.19-2.11 (2H, m), 1.44-1.22 (5H, m), 1.15-1.05 (1H, m).

  2) 2- (3-Chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- [1- [4- [2- (tetrahydropyran-2-yloxy) ethyl] sulfonyl obtained Phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -1H-pyrrole (197 mg, 0.30 mmol) was dissolved in 10 ml of tetrahydrofuran-1N hydrochloric acid (1: 1) and stirred at room temperature for 3 days. The reaction solution was neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained solid was washed with ether to obtain the free form of the title compound, and then converted to the monohydrochloride salt in the same manner as in Example 19 to obtain 151 mg of the title compound as a pale yellow powder (yield 86%). .

Melting point: 247-249 ° C. (decomposition)
¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm of free body:
11.50 (1H, br.s), 8.49 (2H, d, J = 6Hz), 7.79 (2H, d, J = 8Hz),
7.49 (2H, d, J = 8Hz), 7.37-7.27 (2H, m), 7.16 (2H, d, J = 6Hz),
7.05-7.00 (1H, m), 6.96 (1H, d, J = 3Hz), 5.27-5.23 (1H, m),
4.91-4.85 (1H, m), 3.70-3.62 (2H, m), 3.41 (2H, t, J = 7Hz),
2.96-2.88 (2H, m), 2.88-2.81 (2H, m), 2.63-2.49 (4H, m), 2.19-2.12 (2H, m).

(Reference Example 1)
4-bromo-2- (4-fluorophenyl) -3- (pyridin-4-yl) -1-triisopropylsilyl-1H-pyrrole 1) 4-ethoxycarbonyl-2- (4-fluorophenyl) -3- 36 ml (54.7 mmol) of (pyridin-4-yl) -1H-pyrrole 1.53M butyllithium / hexane solution was added into 240 ml of tetrahydrofuran, and then α- (p-toluenesulfonyl) -4-fluoro at −45 ° C. 120 ml of a tetrahydrofuran solution of 15.90 g (54.7 mmol) of benzyl isocyanide was added. After stirring for 10 minutes at the same temperature, 25.00 g (273 mmol) of 95% lithium bromide was added and stirred for 30 minutes, and further 120 ml of a tetrahydrofuran solution of 8.73 g (49.2 mmol) of 3- (4-pyridyl) acrylic acid ethyl ester. Was added. After stirring at the same temperature for 1 hour, the reactor was taken out of the cooling bath and stirred for another hour, 500 ml of water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid was washed with diethyl ether to obtain 13.61 g of the title compound as a pale yellow powder (yield 89%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
8.84 (1H, br.s), 8.51 (2H, d, J = 7Hz), 7.58 (1H, d, J = 3Hz),
7.21 (2H, d, J = 6Hz), 7.11 (2H, dd, J = 9Hz, 5Hz), 6.97 (2H, t, J = 9Hz),
4.18 (2H, q, J = 7Hz), 1.20 (3H, t, J = 7Hz).

2) 4-Ethoxycarbonyl-2- (4-fluorophenyl) -3- (pyridine-4-) obtained from 2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole 1) Yl) -1H-pyrrole (15.00 g, 48.3 mmol) was dissolved in a mixed solution of 90 ml of acetic acid, 30 ml of sulfuric acid and 60 ml of water and stirred at 100 ° C. for 16 hours. After cooling to room temperature, the mixture was made alkaline with 10% aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 11.40 g of the title compound as a pale red powder (yield 99%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
9.78 (1H, br.s), 8.42 (2H, d, J = 7Hz), 7.37 (2H, dd, J = 9Hz, 5Hz),
7.22 (2H, d, J = 6Hz), 7.06 (2H, t, J = 9Hz), 6.90 (1H, t, J = 3Hz),
6.47 (1H, t, J = 3Hz).

3) 2- (4-Fluorophenyl) -3- (pyridine-4) obtained with 2- (4-fluorophenyl) -3- (pyridin-4-yl) -1-triisopropylsilyl-1H-pyrrole 2) -Yl) -1H-pyrrole 11.30 g (47.4 mmol) was dissolved in tetrahydrofuran 300 ml, 1.57 N butyllithium / hexane solution 31 ml (47.4 mmol) was added at −78 ° C., and the mixture was stirred for 10 minutes. At temperature, 13.4 ml (49.8 mmol) of triisopropylsilyl triflate was added. Further, the reactor was removed from the cooling bath and stirred at room temperature for 30 minutes. To the reaction solution are added 200 ml of water and 300 ml of a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 18.70 g of the title compound as a red-purple oil. Obtained (yield: quantitative).

¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
8.25 (2H, d, J = 6Hz), 7.39 (2H, dd, J = 9Hz, 6Hz), 7.28 (2H, t, J = 9Hz),
7.00 (1H, d, J = 3Hz), 6.91 (2H, d, J = 7Hz), 6.71 (1H, d, J = 3Hz),
1.15-1.05 (3H, m), 0.98 (18H, d, J = 8Hz).

4) 2- (4-Fluorophenyl) -3-obtained from 4-bromo-2- (4-fluorophenyl) -3- (pyridin-4-yl) -1-triisopropylsilyl-1H-pyrrole 3) (Pyridin-4-yl) -1-triisopropylsilyl-1H-pyrrole (18.70 g, 47.4 mmol) was dissolved in tetrahydrofuran (300 ml), and N-bromosuccinimide (8.61 g, 47.4 mmol) was added at -78 ° C. 100 ml of a tetrahydrofuran suspension was gradually added, and the mixture was stirred at the same temperature for 6 hours. Further, the reactor was taken out of the cooling bath and stirred at room temperature for 1 hour, and then 400 ml of hexane was added and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (solvent; hexane: ethyl acetate = 2: 1) to obtain 9.57 g of the title compound as pale yellow prismatic crystals (yield 43%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
8.36 (2H, d, J = 6Hz), 7.34 (2H, dd, J = 9Hz, 6Hz),
7.18 (2H, t, J = 9Hz), 7.12 (1H, s), 7.04 (2H, d, J = 6Hz),
1.16-1.08 (3H, m), 0.99 (18H, d, J = 8Hz).

(Reference Example 2)
2- (3-Chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole 1) 4-bromo -1- (t-butyl) diphenylsilyl-2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole a) α- (p-toluenesulfonyl) -4- Instead of fluorobenzyl isocyanide, α- (p-toluenesulfonyl)-(3-chloro-4-fluorobenzyl) isocyanide was used as a starting material to sequentially carry out the reactions of Reference Examples 1-1) and 2), and 2- (3- Chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole was obtained as a slightly pink powder (yield 78%).
b) Next, 29.6 g (109 mmol) of this was dissolved in 300 ml of tetrahydrofuran and added dropwise to a suspension of 9.5 g (218 mmol) of 55% sodium hydride / 600 ml of tetrahydrofuran under ice-cooling and stirring at room temperature. Stir for minutes. After adding 56.7 ml (218 mmol) of (t-butyl) diphenylsilyl chloride to the reaction solution and stirring at room temperature for 1 hour, the reaction was stopped by adding ice water, and tetrahydrofuran was distilled off under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; ethyl acetate) to give 1- (t-butyl) diphenylsilyl-2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl)- 45.2 g of 1H-pyrrole was obtained as a white powder (yield 81%).
c) Next, 45.2 g (88.4 mmol) of this product was dissolved in 900 ml of toluene, and 14.3 ml (176.4 mmol) of pyridine and 33.9 g (106.1 mmol) of pyridinium hydrobromide were added to room temperature. And stirred overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; ethyl acetate: hexane = 1: 2) to give 42.3 g of the title compound as a white powder (yield) 81%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
8.36 (2H, d, J = 6Hz), 7.46-7.29 (11H, m), 7.03 (2H, d, J = 6Hz),
6.72-6.66 (1H, m), 6.56-6.53 (1H, m), 6.53-6.47 (1H, m), 1.06 (9H, s).

2) 2- (3-Chloro-4-fluorophenyl) -3- (pyridin-4-yl) -4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrole 1) 4-Bromo-1- (t-butyl) diphenylsilyl-2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole 14.0 g (23.73 mmol) obtained And 1- (t-butoxycarbonyl) piperidin-4-one 4.73 g (23.73 mmol) were subjected to the same reaction (coupling reaction) as in Example 48-a), and then the reaction solution was saturated with chloride. The reaction was stopped by adding an aqueous ammonium solution, and the solvent was concentrated under reduced pressure. The residue was extracted with ethyl acetate, the organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the residue were added 300 ml of dichloromethane and 50 ml of trifluoroacetic acid, and the mixture was stirred overnight at room temperature (dehydration and de-Boc reaction). The reaction solution was concentrated under reduced pressure, 23.73 ml (237.3 mmol) of 25% aqueous sodium hydroxide solution, 200 ml of methanol, 100 ml of tetrahydrofuran and 50 ml of water were added to the residue, and the mixture was stirred at room temperature for 1 hour (desilylation reaction), and then the solvent. Most of was distilled off under reduced pressure. The residue is extracted with ethyl acetate, and the organic layer is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is then subjected to silica gel column chromatography (solvent; ethyl acetate: methanol: isopropylamine = 100: 10: 1). ) To give 6.52 g of the title compound as a white powder (yield 78%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, DMSO-d ₆ ) δ ppm:
11.64 (1H, br.s), 8.51 (2H, d, J = 6Hz), 7.37-7.28 (2H, m),
7.18 (2H, d, J = 6Hz), 7.09-7.00 (2H, m), 5.22 (1H, br.s),
3.48-3.41 (2H, m), 3.13 (2H, t, J = 6Hz), 2.39-2.30 (2H, m).

(Reference Example 3)
5- (4-Fluorophenyl) -4- (pyridin-4-yl) -3- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrazole 1) 3-Bromo-5- ( 4-Fluorophenyl) -4- (pyridin-4-yl) pyrazole 5- (4-Fluorophenyl) -4- (pyridin-4-yl) pyrazole (Compound No. A described in WO 00/31063) -55 compound) (6.0 g, 25 mmol) was dissolved in dimethylformamide (60 ml), N-bromosuccinimide (8.93 g, 50 mmol) was added, and the mixture was stirred at room temperature for 3 days. Water was added to the reaction solution, and the precipitated crystals were collected and washed with diethyl ether to obtain 5.73 g of the title compound as a white powder (yield 72%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ -DMSO-d ₆ ) δ ppm:
8.56 (2H, d, J = 5Hz), 7.33 (2H, dd, J = 8Hz, 5Hz),
7.24 (2H, d, J = 5Hz), 7.05 (2H, t, J = 8Hz).

2) 5- (4-Fluorophenyl) -4- (pyridin-4-yl) -3- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrazole 3- Bromo-5- (4-fluorophenyl) -4- (pyridin-4-yl) pyrazole 1.20 g (3.77 mmol) and 1- (t-butoxycarbonyl) piperidin-4-one 767 mg (3.77 mmol) The same reaction (coupling reaction) as in Example 48-a) was carried out. To the reaction solution was added 50 ml of saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Concentrated hydrochloric acid (40 ml) was added to the residue and stirred at 110 ° C. for 7 hours (dehydration and de-Boc reaction). Under ice-cooling and stirring, 10% aqueous sodium hydroxide solution was added to make the reaction solution basic, and the precipitated solid was filtered. After taking, it was washed with ethyl acetate to obtain 660 mg of the title compound as a fine brown powder (yield 55%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, DMSO-d ₆ ) δ ppm:
8.52 (2H, d, J = 7Hz), 7.29 (2H, dd, J = 9Hz, 5Hz),
7.18 (2H, d, J = 6Hz), 7.15 (2H, t, J = 9Hz), 5.74 (1H, s),
3.21 (2H, d, J = 3Hz), 2.79 (2H, t, J = 6Hz), 2.13 (2H, br.s).

(Reference Example 4)
4-Carbamoylphenethyl chloride 185 mg (1.0 mmol) of 4-carboxyphenethyl chloride was suspended in 2 ml of dichloromethane, 0.1 ml (1.1 mmol) of oxalyl chloride and 1 drop of dimethylformamide were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added little by little to a mixture of 1 ml of t-butanol-2 ml of tetrahydrofuran-0.5 ml of 28% aqueous ammonia, stirred at room temperature for 3 hours, and then concentrated under reduced pressure. The obtained solid was washed with hexane and diethyl ether to obtain 170 mg of the title compound as a white powder (yield 92%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ ) δ ppm:
7.78 (2H, d, J = 8Hz), 7.31 (2H, d, J = 8Hz), 6.15 (2H, br.s),
3.74 (2H, t, J = 7Hz), 3.12 (2H, t, J = 7Hz).

(Reference Example 5)
3-Carbamoylphenethyl bromide The same compound as in Reference Example 4 was synthesized using 3-carboxyphenethyl bromide instead of 4-carboxyphenethyl chloride to synthesize the title compound.

(Reference Example 6)
4-Methanesulfonylphenylacetaldehyde (Methoxymethyl) triphenylphosphonium chloride 24.80 g (72.3 mmol) was dissolved in 250 ml of methanol, and 15.35 ml (79.6 mmol) of 28% sodium methoxide / methanol solution was added at room temperature. After stirring for 30 minutes, the solvent was distilled off under reduced pressure. To the residue, 375 ml of toluene was added, 10.25 g (55.6 mmol) of 4-methanesulfonylbenzaldehyde was added, and the mixture was stirred at 80 ° C. for 7 hours. The reaction mixture was cooled to room temperature and filtered, the filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (solvent; hexane: ethyl acetate = 2: 1) to give 4-methanesulfonyl-β-methoxystyrene 10 .21 g was obtained as a white powder. Next, 225 ml of tetrahydrofuran and 40.5 ml of water were added to this, and 4.5 ml of concentrated sulfuric acid was further added and heated under reflux for 19 hours. The reaction solution was concentrated under reduced pressure, and water was added to the residue, followed by extraction with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 9.16 g of the title compound as a colorless oil (yield 83%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ ) δ ppm:
9.82 (1H, s), 7.95 (2H, d, J = 8Hz), 7.43 (2H, d, J = 8Hz),
3.86 (2H, s), 3.06 (3H, s).

(Reference Example 7)
(±) -4-Methanesulfinylphenethyl bromide a) 5.97 g (32.8 mmol) of 4-methylthiophenylacetic acid was dissolved in 100 ml of methanol, and 2.63 ml (36.0 mmol) of thionyl chloride was added dropwise with stirring under ice cooling. And stirred at room temperature for 48 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 6.37 g of (±) -4-methylthiophenylacetic acid methyl ester (ester) as a colorless oil. (Yield: quantitative).
b) The ester thus obtained (total amount) was dissolved in 60 ml of tetrahydrofuran, and this solution was added dropwise to a suspension of 2.47 g (65.5 mmol) of lithium aluminum hydride / 100 ml of tetrahydrofuran under ice-cooling and stirring. Then, the mixture was stirred at room temperature for 2 hours, cooled to 0 ° C., and 10 ml of 4% aqueous sodium hydroxide solution was carefully added. The reaction mixture was filtered using Celite, and the filtrate was concentrated under reduced pressure to obtain 5.40 g of (±) -4-methylthiophenethyl alcohol (alcohol) as a white powder (yield 98%).
c) 2.50 g (14.9 mmol) of this alcohol compound was dissolved in 50 ml of dichloromethane, and 4.68 g (17.8 mmol) of triphenylphosphine and 6.41 g (19.3 mmol) of carbon tetrabromide were stirred with ice cooling. The mixture was further stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, diethyl ether was added to the residue, insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane: ethyl acetate = 19: 1) to obtain 3.17 g of (±) -4-methylthiophenethyl bromide (bromide) as a colorless oil (yield 92 %).
d) 3.15 g (13.6 mmol) of this bromide was dissolved in 65 ml of dichloromethane, and 3.62 g (13.6 mmol) of 65% m-chloroperbenzoic acid was added little by little while stirring with ice cooling, and further stirred for 10 minutes. did. The reaction mixture was filtered using Celite, and the filtrate was washed successively with 30 ml of 10% aqueous sodium thiosulfate solution and 30 ml of saturated aqueous sodium hydrogen carbonate solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (solvent; hexane: ethyl acetate = 1: 3) to obtain 2.58 g of the title compound as a colorless oil (yield 77%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ ) δ ppm:
7.62 (2H, d, J = 8Hz), 7.39 (2H, d, J = 8Hz),
3.60 (2H, t, J = 7Hz), 3.24 (2H, t, J = 7Hz), 2.73 (3H, s).

(Reference Example 8)
4- (N-methylsulfamoyl) phenethyl bromide 10.00 g (35.2 mmol) of 4- (chlorosulfonyl) phenethyl bromide was dissolved in 200 ml of tetrahydrofuran, and 9.14 ml (105.6 mmol) of 40% aqueous methylamine was added. Stir at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, water was added to the residue, extracted with dichloromethane, the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 9.63 g of the title compound as a white powder (yield) 98%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
7.82 (2H, d, J = 8Hz), 7.38 (2H, d, J = 8Hz), 4.40-4.30 (1H, m),
3.60 (2H, t, J = 8Hz), 3.25 (2H, t, J = 8Hz), 2.68 (3H, d, J = 5Hz).

  The same reactions as in Reference Example 8 were carried out using various amines instead of methylamine to synthesize compounds of Reference Examples 9-25.

(Reference Example 9)
4- (N-ethylsulfamoyl) phenethyl bromide white powder (yield 99%).

(Reference Example 10)
4- (N-propylsulfamoyl) phenethyl bromide white powder (74% yield).

(Reference Example 11)
4- (N-isopropylsulfamoyl) phenethyl bromide white powder (98% yield).

(Reference Example 12)
4- (N-cyclopropylsulfamoyl) phenethyl bromide white powder (yield 80%).

(Reference Example 13)
4- [N- (2-fluoroethyl) sulfamoyl] phenethyl bromide white powder (82% yield).

(Reference Example 14)
4- (N-phenylsulfamoyl) phenethyl bromide pale brown powder (83% yield).

(Reference Example 15)
4- (N-methoxysulfamoyl) phenethyl bromide white powder (77% yield).

(Reference Example 16)
4- (N, N-dimethylsulfamoyl) phenethyl bromide white powder (98% yield).

(Reference Example 17)
4- [N- (2-methoxyethyl) sulfamoyl] phenethyl bromide white powder (98% yield).

(Reference Example 18)
4- [N- (2-hydroxyethyl) sulfamoyl] phenethyl bromide white powder (95% yield).

(Reference Example 19)
4- (2,2-dimethylhydrazinosulfonyl) phenethyl bromide slightly yellow powder (95% yield).

(Reference Example 20)
4- [N- (Pyridin-3-yl) methylsulfamoyl] phenethyl bromide White powder (Yield; quantitative).

(Reference Example 21)
4- [N- (2-dimethylaminoethyl) sulfamoyl] phenethyl bromide white powder (56% yield).

(Reference Example 22)
4- [N- (1,3-dihydroxypropan-2-yl) sulfamoyl] phenethyl bromide white powder (97% yield).

(Reference Example 23)
4- (N-ethoxysulfamoyl) phenethyl bromide white powder (97% yield).

(Reference Example 24)
4- (N-benzyloxysulfamoyl) phenethyl bromide white powder (yield; quantitative).

(Reference Example 25)
4- (N-allyloxysulfamoyl) phenethyl bromide white powder (95% yield).

(Reference Example 26)
α-Bromo-4- (N-methylsulfamoyl) acetophenone a) The same reaction as in Reference Example 8 was carried out using 4- (chlorosulfonyl) acetophenone instead of 4- (chlorosulfonyl) phenethyl bromide, (N-methylsulfamoyl) acetophenone was obtained as a white powder (yield 97%).
b) Next, 3.30 g (15.5 mmol) of this product was dissolved in 33 ml of tetrahydrofuran, and 0.79 ml (15.5 mmol) of bromine was slowly added dropwise with stirring at room temperature. After stirring at room temperature for 1 hour, 200 ml of ethyl acetate and 50 ml of water were added for liquid separation, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (solvent; hexane: ethyl acetate = 2: 1) to obtain 3.79 g of the title compound as a white powder (yield 84%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
8.13 (2H, d, J = 8Hz), 7.99 (2H, d, J = 8Hz), 4.54 (1H, quartet, J = 5Hz),
4.45 (2H, s), 2.72 (3H, d, J = 5Hz).

(Reference Example 27)
(2S, 8aS) -2- (4-methoxycarbonylphenyl) -1,2,3,5,6,7,8,8a-octahydroindolizin-7-one 1) (S) -4-Bromo- β- (2,2-diethoxyethyl) phenethylamine a) 75.0 g (0.383 mol) of 4-bromobenzylcyanide was dissolved in 750 ml of tetrahydrofuran, cooled to −15 ° C. or lower and 1.0 M lithium bis (trimethylsilyl). ) After adding 423 ml (0.423 mol) of amide / tetrahydrofuran solution and stirring at the same temperature for 1 hour, the cooling bath was removed and the temperature was returned to room temperature, and 86.5 ml (0.575 mol) of 2,2-diethoxyethyl bromide was added dropwise. And stirred at room temperature for 6 hours. The solvent was distilled off under reduced pressure, water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane: ethyl acetate = 10: 1), and the residue was distilled under reduced pressure to obtain (±) -4-bromo-α- (2,2-diethoxyethyl) benzyl cyanide. 88.95 g was obtained as a brown oil (boiling point: 51-54 ° C./8 mmHg, yield 95%).

  b) 20.34 g (0.536 mol) of lithium aluminum hydride was suspended in 700 ml of tetrahydrofuran, 13.49 ml (0.253 mol) of concentrated sulfuric acid was added dropwise at 10 ° C. or less, and the mixture was stirred at 0 to 5 ° C. for 1 hour. The reaction solution was returned to room temperature, and 119.5 g (0.383 mol) / tetrahydrofuran solution 50 ml of (±) -4-bromo-α- (2,2-diethoxyethyl) benzyl cyanide obtained in a) above was added dropwise. And stirred for 2 hours. An additional 750 ml of tetrahydrofuran was added, 107 ml (0.28 ml) of 1N aqueous sodium hydroxide solution was carefully added, and the mixture was stirred at room temperature for 1 hour and filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (solvent; ethyl acetate: methanol: isopropylamine = 20: 1: 1) to give (±) -4-bromo-β- (2,2- Diethoxyethyl) phenethylamine 80.40 g was obtained as a yellow oil (yield 66%).

  c) 80.40 g (0.254 mol) of (±) -4-bromo-β- (2,2-diethoxyethyl) phenethylamine obtained in b) above and 28.60 g (0.191 mol) of D-tartaric acid The suspension was suspended in 402 ml of isopropanol, stirred at 100 ° C. for 30 minutes to obtain a homogeneous solution, and then allowed to stand overnight at room temperature. The precipitated crystals were collected by filtration, washed twice with 160 ml of isopropanol, and a salt of (S) -4-bromo-β- (2,2-diethoxyethyl) phenethylamine and D-tartaric acid (1: 1) 46 .81 g was obtained. Next, 470 ml of toluene and 95 ml of water were added to this, and a 25% aqueous sodium hydroxide solution was added dropwise with vigorous stirring to adjust the pH to 12-13. The reaction mixture is separated, and the organic layer is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is distilled under reduced pressure to give (S) -4-bromo-β- (2,2-diethoxyethyl) phenethylamine 29. Obtained 0.01 g as a colorless oil (boiling point: 176-178 ° C./5.8 mmHg, yield 72%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
7.45 (2H, d, J = 9Hz), 7.09 (2H, d, J = 9Hz), 4.25-4.20 (1H, m),
3.66-3.58 (1H, m), 3.55-3.48 (1H, m), 3.43-3.33 (2H, m),
2.95-2.89 (1H, m), 2.82 (1H, dd, J = 12Hz, 3Hz), 2.79-2.72 (1H, m),
2.03-1.96 (1H, m), 1.80 (1H, ddd, J = 14Hz, 10Hz, 6Hz),
1.19 (3H, t, J = 7Hz), 1.13 (3H, t, J = 7Hz).

2) (2S, 8aS) -2- (4-Bromophenyl) -1,2,3,5,6,7,8,8a-octahydroindolizin-7-one 1) (S)- 29.01 g (91.7 mmol) of 4-bromo-β- (2,2-diethoxyethyl) phenethylamine was dissolved in 145 ml of toluene, and 9.92 ml (119.2 mmol) of methyl vinyl ketone was added while stirring at 60 ° C. And stirred for 30 minutes at the same temperature. After cooling the reaction solution to room temperature, 15.25 ml (183 mmol) of concentrated hydrochloric acid and 15.25 ml of water were added for liquid separation, and 22.92 ml of concentrated hydrochloric acid and 57.3 ml of ethanol were added to the aqueous layer, followed by stirring at 50 ° C. for 6 hours. Then, the reaction solution was cooled to room temperature, adjusted to pH 12-13 with 25% aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography (solvent; hexane: ethyl acetate = 1: 1) to give 17.34 g of the title compound as a brown powder. (Yield 64%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
7.42 (2H, d, J = 8Hz), 7.11 (2H, d, J = 8Hz), 3.58-3.47 (2H, m),
3.35 (1H, dd, J = 10Hz, 7Hz), 2.69-2.54 (3H, m),
2.44 (1H, dd, J = 10Hz, 3Hz), 2.42-2.33 (2H, m), 2.32-2.27 (1H, m),
2.15-2.01 (2H, m).

3) (2S, 8aS) -2- (4-methoxycarbonylphenyl) -1,2,3,5,6,7,8,8a-octahydroindolizin-7-one 2) 8aS) -2- (4-Bromophenyl) -1,2,3,5,6,7,8,8a-octahydroindolizin-7-one 8.00 g (27.2 mmol) of methanol 272 ml and N, Dissolve in a mixture of 54 ml of N-dimethylformamide, 4.44 g (5.44 mmol) of [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II) and 9.48 ml (54.4 mmol) of ethyldiisopropylamine. ) Was added and stirred at 70 ° C. for 5 hours in a carbon monoxide atmosphere. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added for liquid separation, and the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; ethyl acetate) to obtain 6.50 g of the title compound as a light brown powder (yield 87%). As a result of HPLC analysis under the following conditions, the optical purity of this product was 91% ee.
HPLC conditions Column: CHIRALPAK AS-H (manufactured by Daicel Chemical Industries, Ltd.)
(Inner diameter 0.46cm, length 25cm)
Mobile phase: n-hexane / ethanol / isopropylamine = 90/10 / 0.1
Flow rate: 1.0 ml / min
Temperature: 40 ° C
Detection: 254 nm (UV)
Retention time: (2S, 8aS) body 15.48 minutes
(2R, 8aR) body 11.80 minutes.

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
7.98 (2H, d, J = 8Hz), 7.30 (2H, d, J = 8Hz), 3.91 (3H, s),
3.69-3.58 (1H, m), 3.57-3.50 (1H, m), 3.39-3.32 (1H, m),
2.70-2.55 (3H, m), 2.46 (1H, dd, J = 11Hz, 4Hz), 2.43-2.32 (3H, m),
2.16-2.09 (2H, m).

(Reference Example 28)
1- [4- (N-methylsulfamoyl) phenyl] cyclopropane-1-carboxaldehyde 1) 1- (4-Chlorosulfonylphenyl) cyclopropane-1-carboxylic acid methyl ester 1-phenylcyclopropane-1- 2.67 g (15.15 mmol) of carboxylic acid methyl ester was dissolved in 27 ml of dichloromethane, and 5.15 ml (77.5 mmol) of chlorosulfonic acid was added dropwise with stirring under ice cooling, followed by stirring at room temperature for 5 hours. Was concentrated under reduced pressure, ethyl acetate was added to the residue, and then water was carefully added. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane: ethyl acetate = 10: 1) to give the title compound as a white powder (yield). (Rate 52%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
7.98 (2H, d, J = 8Hz), 7.59 (2H, d, J = 8Hz), 3.66 (3H, s),
1.75-1.70 (2H, m), 1.27-1.23 (2H, m).

2) 1- [4- (N-methylsulfamoyl) phenyl] cyclopropane-1-carboxylic acid methyl ester 1- (4-chlorosulfonylphenyl) cyclopropane-1-carboxylic acid methyl ester 2 obtained in 1) .16 g (7.86 mmol) was dissolved in 22 ml of tetrahydrofuran, 2.44 g (23.6 mmol) of 30% methylamine / ethanol solution was added with stirring under ice cooling, and the mixture was stirred at room temperature for 30 minutes. Ethyl acetate and water were added to the reaction solution for liquid separation, and the organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The solid residue was washed with hexane to obtain 2.13 g of the title compound as a white powder (yield: quantitative).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
7.80 (2H, d, J = 8Hz), 7.50 (2H, d, J = 8Hz), 4.35 (1H, quartet, J = 5Hz),
3.64 (3H, s), 2.69 (3H, d, J = 5Hz), 1.70-1.66 (2H, m), 1.24-1.20 (2H, m).

3) 1- [4- (N-methylsulfamoyl) phenyl] cyclopropane-1-carboxylic acid obtained from 1- [4- (N-methylsulfamoyl) phenyl] cyclopropane-1-methanol 2) The methyl ester was reduced with lithium aluminum hydride in the same manner as in Reference Example 7 to obtain the title compound as a white powder (yield 94%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
7.79 (2H, d, J = 9Hz), 7.50 (2H, d, J = 9Hz), 4.46-4.33 (1H, m),
3.74 (2H, s), 2.66 (3H, d, J = 6Hz), 0.99-0.92 (4H, m).

4) Suspend 4.33 g (20.1 mmol) of 1- [4- (N-methylsulfamoyl) phenyl] cyclopropane-1-carboxaldehyde pyridinium chlorochromate and 4.33 g of molecular sieve 4A in 50 ml of dichloromethane. 3) After adding 0.97 g (4.02 mmol) of 1- [4- (N-methylsulfamoyl) phenyl] cyclopropane-1-methanol obtained in 1 above and stirring at room temperature for 1 hour, 50 ml of diethyl ether was added and filtered. did. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (solvent; hexane: ethyl acetate = 1: 2) to obtain 0.88 g of the title compound as a white powder (yield 92%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
9.09 (1H, s), 7.83 (2H, d, J = 9Hz), 7.44 (2H, d, J = 9Hz),
4.28 (1H, quartet, J = 5Hz), 2.69 (3H, d, J = 5Hz),
1.67-1.63 (2H, m), 1.49-1.45 (2H, m).

(Reference Example 29)
(±) -α-methyl-4- (N-methylsulfamoyl) phenylacetaldehyde instead of 1-phenylcyclopropane-1-carboxylic acid methyl ester, (±) -α-methylphenylacetic acid ethyl ester was used as a starting material The same reactions as in Reference Example 28-1), 2), 3) and 4) were sequentially carried out to obtain the title compound as a white powder (total yield 26%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ ) δ ppm:
9.71 (1H, s), 7.88 (2H, d, J = 8Hz), 7.39 (2H, d, J = 8Hz),
4.45-4.38 (1H, m), 3.75 (1H, quartet, J = 7Hz), 2.69 (3H, d, J = 5Hz),
1.50 (3H, d, J = 7Hz).

(Reference Example 30)
(±) -α-ethyl-4- (N-methylsulfamoyl) phenylacetaldehyde instead of 1-phenylcyclopropane-1-carboxylic acid methyl ester, (±) -α-ethylphenylacetic acid ethyl ester was used as a starting material Reference Example 28-1), 2). The same reaction as 3) and 4) was sequentially performed to obtain the title compound as a colorless oil (total yield 5%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ ) δ ppm:
9.68 (1H, d, J = 2Hz), 7.85 (2H, d, J = 8Hz), 7.34 (2H, d, J = 8Hz),
4.40 (1H, quartet, J = 5Hz), 3.54-3.50 (1H, m), 2.69-2.68 (3H, m),
2.22-2.11 (1H, m), 1.85-1.74 (1H, m), 0.92 (3H, t, J = 7Hz).

(Reference Example 31)
(±) -α-ethyl-4-methanesulfonylphenylacetaldehyde instead of 1- [4- (N-methylsulfamoyl) phenyl] cyclopropane-1-carboxylic acid methyl ester (±) -α-ethyl-4 -Methanesulfonylphenylacetic acid methyl ester was used as a starting material, and the same reaction as in Reference Examples 28-2) and 3) was sequentially carried out to obtain the title compound as a yellow oil (total yield 56%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ ) δ ppm:
9.72 (1H, s), 7.96 (2H, d, J = 8Hz), 7.42 (2H, d, J = 8Hz),
3.59-3.54 (1H, m), 3.07 (3H, s), 2.24-2.14 (1H, m),
1.86-1.75 (1H, m), 0.93 (3H, t, J = 7Hz).

  The same reaction as in Reference Example 8 was performed using a glycine derivative (methyl ester, amide or nitrile) instead of methylamine to synthesize compounds of Reference Examples 32-34.

(Reference Example 32)
4- (N-methoxycarbonylmethylsulfamoyl) phenethyl bromide white powder (yield; quantitative).

(Reference Example 33)
4- (N-carbamoylmethylsulfamoyl) phenethyl bromide yellow powder (49% yield).

(Reference Example 34)
4- (N-cyanomethylsulfamoyl) phenethyl bromide yellow oil (yield 81%).

(Reference Example 35)
2- [5- (N-methylsulfamoyl) thiophen-2-yl] ethyl bromide 2- (2-bromoethyl) thiophene was used to carry out a chlorosulfonylation reaction in the same manner as in Reference Example 28. 2-Bromoethyl) -5-chlorosulfonylthiophene was obtained. This was then reacted with methylamine in the same manner as in Reference Example 8 to obtain the title compound as a white powder (yield 44%).

¹ H-nuclear magnetic resonance spectrum (500 MHz, CDCl ₃ ) δ ppm:
7.45 (1H, d, J = 4Hz), 6.88 (1H, d, J = 4Hz), 4.45-4.30 (1H, m),
3.57 (2H, t, J = 7Hz), 3.39 (2H, t, J = 7Hz), 2.73 (3H, d, J = 5Hz).

(Reference Example 36)
3-Methoxy-4- (N-methylsulfamoyl) phenethyl bromide A 3-chlorophenethyl bromide was used to carry out a chlorosulfonylation reaction in the same manner as in Reference Example 28, to give 4-chlorosulfonyl-3-methoxyphenethyl bromide. Obtained. This was then reacted with methylamine in the same manner as in Reference Example 8 to obtain the title compound as a white powder (yield 6%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ ) δ ppm:
7.86 (1H, d, J = 8Hz), 6.94 (1H, d, J = 8Hz), 6.89 (1H, s),
4.82-4.74 (1H, m), 3.99 (3H, s), 3.59 (2H, t, J = 7Hz),
3.22 (2H, t, J = 7Hz), 2.59 (3H, d, J = 6Hz).

(Reference Example 37)
3-Fluoro-4- (N-methylsulfamoyl) phenethyl bromide The same reaction as in Reference Example 36 was performed using 3-fluorophenethyl bromide to obtain the title compound as a white powder (yield 5%).

(Reference Example 38)
3-Chloro-4- (N-methylsulfamoyl) phenethyl bromide The same reaction as in Reference Example 36 was performed using 3-chlorophenethyl bromide to obtain the title compound as a white powder (yield 6%).

(Reference Example 39)
3-Methyl-4- (N-methylsulfamoyl) phenethyl bromide The same reaction as in Reference Example 36 was performed using 3-methylphenethyl bromide to obtain the title compound as a white powder (yield 11%).

(Reference Example 40)
4- (2-methoxyethyl) sulfonylphenethyl bromide 1) 1.10 g (7.13 mmol) of 4-mercaptophenethyl alcohol and 0.98 ml (10.7 mmol) of 2-methoxyethyl chloride were dissolved in 22 ml of methanol, and potassium carbonate 1 .48 g (10.7 mmol) was added and heated to reflux for 4 hours. After cooling, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (solvent; hexane: ethyl acetate = 3: 1) to obtain 1.18 g of 4- (2-methoxyethyl) sulfanylphenethyl alcohol (sulfide) as a colorless oil (yield) 78%).

2) 1.17 g (5.51 mmol) of this sulfide compound was dissolved in 30 ml of dichloromethane, and 2.93 g (11.0 mmol) of m-chloroperbenzoic acid (65%) was added with stirring under ice cooling, and the mixture was stirred at room temperature for 20 hours. Stir. After adding 1.23 g (16.5 mmol) of calcium hydroxide to the reaction solution and stirring for 15 minutes, the reaction mixture was filtered using Celite, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography (solvent; hexane: ethyl acetate = 1: 3) to obtain 1.26 g of 4- (2-methoxyethyl) sulfonylphenethyl alcohol (alcohol) as a colorless oil. (Yield 94%)
3) 1.04 g (4.26 mmol) of this alcohol is dissolved in 21 ml of dichloromethane, and 1.34 g (5.11 mmol) of triphenylphosphine and 1.84 g (5.53 mmol) of carbon tetrabromide are stirred under ice-cooling. The mixture was further stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel chromatography (solvent; hexane: ethyl acetate = 3: 2) to give 1.25 g of the title compound as a colorless oil (yield 95%).

¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ ) δ ppm:
7.88 (2H, d, J = 8Hz), 7.42 (2H, d, J = 8Hz), 3.75 (2H, t, J = 7Hz),
3.61 (2H, t, J = 7Hz), 3.39 (2H, t, J = 7Hz), 3.27 (2H, t, J = 7Hz), 3.23 (3H, s).

(Reference Example 41)
4- [2- (Tetrahydropyran-2-yloxy) ethyl] sulfonylphenethyl bromide Instead of 2-methoxyethyl chloride, 2- (tetrahydropyran-2-yloxy) ethyl chloride was used for the same reaction as in Reference Example 40. And the title compound was obtained as white crystals (yield 22%).
¹ H-nuclear magnetic resonance spectrum (400 MHz, CDCl ₃ ) δ ppm:
7.88 (2H, d, J = 8Hz), 7.41 (2H, d, J = 8Hz), 4.51-4.47 (1H, m),
4.09-4.02 (1H, m), 3.84-3.76 (1H, m), 3.75-3.67 (1H, m),
3.59 (2H, t, J = 7Hz), 3.50-3.40 (3H, m),
3.26 (2H, t, J = 7Hz), 1.62-1.36 (5H, m), 1.36-1.25 (1H, m).

[Formulation example]
A preparation containing the compound having the above general formula (I) of the present invention or a pharmacologically acceptable salt, ester or other derivative thereof as an active ingredient can be produced, for example, by the following method.

[Formulation Example 1] Powder A powder is obtained by mixing 5 g of the compound of Example 19, 895 g of lactose and 100 g of corn starch with a blender.

[Formulation Example 2] Granules After mixing 5 g of the compound of Example 23, 865 g of lactose and 100 g of low-substituted hydroxypropylcellulose, 300 g of a 10% hydroxypropylcellulose aqueous solution is added and kneaded. This is granulated using an extrusion granulator and dried to obtain granules.

[Formulation Example 3] Capsules After mixing 5 g of the compound of Example 40, 115 g of lactose, 58 g of corn starch and 2 g of magnesium stearate using a V-type mixer, a capsule is obtained by filling 180 mg into No. 3 capsules. .

[Formulation Example 4] Tablet Example 41 After mixing 5 g of the compound, 90 g of lactose, 34 g of corn starch, 20 g of crystalline cellulose and 1 g of magnesium stearate with a blender, the tablet is obtained by tableting with a tablet machine.

[Test Example 1]
Inhibition test on human whole blood IL-1β and TNFα production (in vitro)
Hartman et al. (DAHartman, SJOchalski and RPCarlson; The effects of antiinflammatory and antiallergic drugs on cytokine release after stimulation of human whole blood by lipopolysaccharide and zymosan A: Inflamm. Res., 44, 269 (1995)).

Peripheral blood was collected from healthy volunteers in the presence of heparin. 1000 μl of whole blood was added to an Eppendorf tube to which 2 μl of a dimethyl sulfoxide solution of a test compound was added in advance, and lipopolysaccharide (LPS) (derived from E. coli O26: B6, Difco) as a stimulant (final concentration 10 μg / ml) After adding 10 μl, the mixture was mixed well and cultured at 37 ° C. under 5% CO ₂ for 6 hours. After completion of the culture, the reaction was stopped by cooling to 4 ° C., and immediately centrifuged at 14,000 rpm for 5 minutes to separate and collect the supernatant plasma. IL-1β and TNFα produced and released in plasma were measured with an enzyme immunoassay (ELISA) kit (Cayman and Genzyme). The inhibition rate was determined from the amount of cytokine produced in the presence and absence of the test compound. Based on these average inhibition rates, IC ₅₀ values were determined by the method of least squares.
(Table 17)
-------------------------------------------------- ------------------------------
Human whole blood Human whole blood Test compound IL-1β production inhibition TNFα production inhibition
IC ₅₀ [μM] IC ₅₀ [μM]
-------------------------------------------------- ------------------------------
Compound of Example 6 3.6 4.3
Compound of Example 8 0.6 2.5
Compound of Example 9 1.6 4.9
Compound of Example 42 31 6.7
Compound of Example 45 2.7 5.7
Compound of Example 51 10 3.3
Compound of Example 52 2.4 1.5
Compound of Example 54 18 5.5
Compound of Example 57 4.6 3.4
Compound of Example 64 3.4 3.6
-------------------------------------------------- ------------------------------
In this test, as shown in Table 17 above, the compound of the present invention showed an excellent inhibitory effect on cytokine production.

[Test Example 2]
TNFα production inhibition test (in vivo)
Ochalski et al. (SJOchalski, DAHartman, MTBelfast, TLWalter, KBGlaser and RPCarlson; Inhibition of endotoxin-induced hypothermia and serum TNF-α levels in CD-1 mice by various pharmacological agents: Agents Actions 39, C52-C54 (1993)) It carried out according to.

  LPS production was induced by intravenous injection of LPS into mice. Balb / c mice (male, 5-7 weeks old, body weight around 22 g, Japanese Charles River) fasted overnight from the day before the experiment were prepared to 0.045 mg / ml using a physiological saline solution in the tail vein. LPS (derived from E. coli O26: B6, Difco) was administered at a rate of 10 ml / kg body weight. One hour later, the mouse was opened under ether anesthesia, and blood was collected from the abdominal vena cava. In addition, a 1 ml disposable syringe with a 23G needle attached and wetted with heparin on the inner wall was used for blood collection. After blood collection, the blood was immediately transferred to a 1.5 ml Eppendorf tube and centrifuged at 4 ° C. and 14,000 rpm to separate plasma. This plasma was stored at −20 ° C. until measurement of TNFα.

  The amount of TNFα was measured with an enzyme immunoassay (ELISA) kit (mouse TNFα ELISA KIT, Genzyme).

The test compound was suspended in 0.5% tragacanth solution and orally administered at a ratio of 10 ml / kg body weight 30 minutes before the injection of LPS. A minimum of 3 doses per test compound was administered to each of 5 mice. The average inhibition rate relative to the control group was calculated for each dose. Based on these average inhibition rates, the ID ₅₀ value was determined by the method of least squares.
(Table 18)
-------------------------------------------------- ----------
Mouse LPS induction Test compound TNFα production inhibition
ID ₅₀ [μM]
-------------------------------------------------- ---------
Compound of Example 8 0.49
Compound of Example 42 0.32
Compound of Example 45 0.71
Compound of Example 54 0.41
Compound of Example 64 0.86
-------------------------------------------------- ----------
In this test, as shown in Table 18 above, the compound of the present invention showed an excellent TNFα production inhibitory action.

[Test Example 3]
IL-1β production inhibition test (in vivo)
Griffith et al. (Richard J. Griffiths, Ethan J. Stam, James T. Downs and Ivan G. Otterness; ATP Induces the Release of IL-1 from LPS-Primed Cells In Vivo: J. Immunol., 154, 2821- 2828 (1995)).

  IL-1β production was induced by intraperitoneal injection of LPS and adenosine triphosphate (ATP) into mice. LPS prepared to a concentration of 0.0045 mg / ml in the abdominal cavity of Balb / c mice (male, 5-7 weeks old, around 22 g, Nippon Charles River) fasted overnight from the day before the experiment. (E. coli O26: derived from B6, Difco) was administered at a rate of 10 ml / kg body weight. Two more hours later, 0.5 ml of ATP prepared to 6.03 mg / ml using a physiological saline solution was intraperitoneally administered. 0.5 hours after administration of ATP, immediately after suffocating with dry ice, 3 ml of PBS for washing (heparin: 10 U / ml, PMSF: 0.25 mM, leupepsin: 1 μg / ml, pepstatin: 1 μg / ml, EDTA: 1 mM) was injected intraperitoneally and the peritoneal cavity was washed. A 1 ml disposable syringe equipped with a 21G needle was used to collect the cleaning solution. After recovery, the washing solution from the abdominal cavity was immediately transferred to a 1.5 ml Eppendorf tube, and centrifuged at 4 ° C. and 7,500 rpm to separate the supernatant. This supernatant was stored at −20 ° C. until measurement of IL-1β.

The amount of IL-1β was measured with an enzyme immunoassay (ELISA) kit (mouse ELISA KIT, Genzyme). The test compound was suspended in 0.5% tragacanth and 10 ml / body weight 30 minutes before LPS injection. Oral administration was performed at a rate of 1 kg. A minimum of 3 doses per test compound was administered to each of 5 mice. The average inhibition rate relative to the control group was calculated for each dose.

  In this test, the compound of the present invention showed an excellent IL-1β production inhibitory action.

[Test Example 4]
Adjuvant arthritis onset suppression test (in vivo)
This was performed according to the method of Winder et al. (Arthritis Rheum., 12, 472-482, 1969).

  Heat-killed Mycobacterium butyricum cells (Difco Laboratories, lot 679123) are refined in an agate mortar and suspended in dry paraffin sterilized liquid paraffin (Wako Pure Chemical Industries, Ltd., first grade) at 2 mg / ml. Adjuvant was made by turbidity and sonication. This adjuvant (100 μg / 0.05 ml / paw as a heated dead cell) was injected into the right hind paw skin of a Lewis female rat (9 weeks old, weight around 190 g, Nippon Charles River Co., Ltd.), and arthritis Evoked.

  The test compound was suspended in 0.5% sodium carboxymethylcellulose aqueous solution and orally administered at a rate of 5 ml / kg once a day from the day of adjuvant injection (Day 0) to Day 20.

  On days 3, 5, 7, 10, 13, 15, 18 and 21 after injection of the adjuvant, the volume of the right foot (foot injected with adjuvant) and the left foot (non-injected foot) were measured, and the swelling volume (adjuvant) Injection animal hind paw volume-healthy group hind paw volume) was calculated. For measuring the foot volume, a rat foot volume measuring device (Plesthymometer, Ugo Basile) was used, and the hair from the hairline of the hind limb to the tip of the foot was placed in the water tank of the measuring device.

  Furthermore, the swelling suppression rate of the test compound administration group with respect to the test compound non-administration control group on the 21st day was calculated by the following formula.

Swelling suppression rate (%) =
{1- (swelling volume of test compound administration group) / (swelling volume of control group)} × 100
(Table 19)
-------------------------------------------------- ----------

Test compound Swelling inhibition rate [%]
-------------------------------------------------- ---------
Compound of Example 45 70.6
Compound of Example 64 65.1
-------------------------------------------------- ----------
In this test, as shown in Table 19, the compound of the present invention showed an excellent inhibitory effect on the development of adjuvant arthritis.

[Test Example 5]
Anti-collagen antibody-induced arthritis suppression test (in vivo)
In this study, a mouse anti-collagen antibody-induced arthritis model was employed.

  Balb / c mice (male, 5-6 weeks old, Nippon Charles River Co., Ltd.) with 0.5 ml of anti-collagen antibody solution (4 mg / ml, Arthritis cocktail manufactured by Immunobiological Laboratories, Inc.) Three days after the administration, 0.1 ml of a lipopolysaccharide solution (0.5 mg / ml, Arthritis cocktail manufactured by Immunobiological Laboratories, Inc.) was intraperitoneally administered to induce arthritis.

  The test compound was suspended in 0.5% tragacanth solution and orally administered at a rate of 10 ml / kg once a day for 7 days from the day when the anti-collagen antibody solution was administered. In the control group, 0.5% tragacanth solution was administered instead of the suspension of the test compound.

  After the administration of the test compound (or tragacanth solution) was completed, the degree of swelling was scored for each limb according to the following criteria.

0: Normal (no swelling observed)
1: Swelling is observed in one finger 2: Swelling is observed in two or more fingers 3: The entire limb is swollen.

  For each individual, the sum of the scores of the limbs is used as the solid swelling score, and the inhibition rate is calculated from the score of each individual in the test compound administration group relative to the average score of the control group. Judged.

  In this test, the compound of the present invention showed an excellent anti-collagen antibody-induced arthritis development inhibitory effect.

[Test Example 6]
Anti-collagen antibody-induced arthritis treatment test (in vivo)
In this study, a mouse anti-collagen antibody-induced arthritis model was employed.

  Balb / c mice (male, 5-6 weeks old, Nippon Charles River Co., Ltd.) with 0.5 ml of anti-collagen antibody solution (4 mg / ml, Arthritis cocktail manufactured by Immunobiological Laboratories, Inc.) Three days after the administration, 0.1 ml of a lipopolysaccharide solution (0.5 mg / ml, Arthritis cocktail manufactured by Immunobiological Laboratories, Inc.) was intraperitoneally administered to induce arthritis.

  Seven days after the administration of the anti-collagen antibody solution, the degree of swelling was scored according to the criteria shown in Test Example 5 and mice with scores of both hind limbs of 3 were selected and used for the treatment test. I did it.

  The test compound was suspended in 0.5% tragacanth solution and orally administered at a rate of 10 ml / kg once a day for 3 days from the day of selection. In the control group, 0.5% tragacanth solution was administered instead of the suspension of the test compound.

  After the administration of the test compound (or tragacanth solution) was completed, the degree of swelling of both hind limbs was scored again according to the criteria shown in Test Example 5. The inhibition rate was calculated from the score of each individual in the test compound administration group with respect to the average score of the control group, thereby judging the inhibitory activity of the test compound.

  In this test, the compound of the present invention showed an excellent anti-collagen antibody-induced arthritis therapeutic action.

[Test Example 7]
Lifesaving study against galactosamine (GalN) / lipopolysaccharide (LPS) -induced lethality in mice (septic model) Sepsis was induced by injecting mice with GalN and LPS into the tail vein.

  Using physiological saline, prepare GalN (manufactured by Sigma) adjusted to 1 g / 5 ml and LPS (manufactured by Sigma) adjusted to 0.05 mg / 5 ml. Mix in equal amounts. The mixed solution was added to the mouse [C3H / He. N (male, 7 weeks old, Charles River Japan, Inc., 10 animals per group) was injected into the tail vein at a rate of 10 ml / kg to induce lethality due to sepsis.

  The test compound was dissolved in physiological saline and injected into the tail vein at a rate of 10 ml / kg immediately before injection of the GalN / LPS solution.

  The life and death were observed and recorded for 3 days after the lethal induction, and the lifesaving effect was judged.

Claims (48)

The following general formula (I)

{Where,
A is a trivalent group selected from benzene, pyridine, pyridazine, pyrimidine, pyrrole, furan, thiophene, pyrazole, imidazole, isoxazole and isothiazole groups, which may be substituted with a group selected from substituent group δ Indicate
R ¹ is an aryl group optionally substituted with a group selected from substituent group α and substituent group β; or optionally substituted with a group selected from substituent group α and substituent group β Represents a heteroaryl group,
R ² represents a heteroaryl group having at least one nitrogen atom, which may be substituted with a group selected from substituent group α and substituent group β,
R ³ is a group having the following general formula (IIa) or (IIb):

[Where:
A bond including a dotted line indicates a single bond or a double bond,
Ring B represents a 4- to 7-membered heterocyclyl ring (the ring is saturated or unsaturated; may be condensed with an aryl group, heteroaryl group, cycloalkyl group, or heterocyclyl group);
X represents a linear or branched alkylene group having 1 to 5 carbon atoms,
Y represents a single bond or a group having the formula C (R ⁸ a) (R ⁸ b) (R ⁸ a and R ⁸ b are the same or different and each represents a hydrogen atom, a hydroxy group, a halogen atom, or a lower alkyl group. Or a lower alkoxy group, R ⁸ a and R ⁸ b together represent an oxo group or a methylene group, or a carbon atom to which R ⁸ a and R ⁸ b are bonded. And a 3- to 6-membered cycloalkyl group is formed.)
Z represents an arylene group or a heteroarylene group,
m represents 0 to 2,

R ⁵ is a carboxy group, a lower alkoxycarbonyl group, an aralkyloxycarbonyl group, an aryloxycarbonyl group, a group having the formula CONR ^a R ^b , a group having the formula COR ^c , a group having the formula SO ₂ NR ^a R ^b , a formula A group having SO ₂ R ^c or a group having the formula SOR ^c
R ^a and R ^b are the same or different and each represents a hydrogen atom, a hydroxy group,
A lower alkyl group which may be substituted with a group selected from substituent group α,
A lower alkenyl group optionally substituted with a group selected from substituent group α,
A lower alkynyl group optionally substituted with a group selected from substituent group α,
A lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, an aralkyloxy group,
A cycloalkyl group, a lower alkyl group substituted with a cycloalkyl group,
Aryl group, aralkyl group,
A heteroaryl group, a lower alkyl group substituted with a heteroaryl group,
Represents an amino group or a mono- or di-lower alkylamino group,
R ^c represents a hydrogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy lower alkyl group or a hydroxy lower alkyl group,

R ⁶ consists of a hydrogen atom, hydroxy group, amino group, nitro group, cyano group, halogen atom, lower alkyl group, lower alkoxy group, lower alkylthio group, halogeno lower alkyl group, halogeno lower alkoxy group and halogeno lower alkylthio group. 1 to 2 groups selected from the group,
n represents 1 to 2 (when n is 2, R ⁶ may be the same or different);

R ⁷ is 1 to 3 selected from the group consisting of a hydrogen atom, a hydroxy group, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halogeno lower alkyl group, a halogeno lower alkoxy group, and a halogeno lower alkylthio group The group of is shown. ]

Substituent group α is
Hydroxy group, nitro group, cyano group, halogen atom, lower alkoxy group, halogeno lower alkoxy group, carboxy group, lower alkoxycarbonyl group, carbamoyl group, lower acyloxy group, lower alkylthio group, halogeno lower alkylthio group and formula —NR ^d R a group having ^e (wherein R ^d and R ^e are the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, an aralkyl group, a lower alkylsulfonyl group or a lower alkylcarbonyl group; Or, together with the nitrogen atom to which R ^d and R ^e are bonded, forms a heterocyclyl group).

Substituent group β is
A lower alkyl group which may be substituted with a group selected from substituent group α,
A lower alkenyl group optionally substituted with a group selected from substituent group α,
An alkynyl group optionally substituted with a group selected from substituent group α,
Represents a group consisting of an aralkyl group and a cycloalkyl group;

Substituent group γ is
An oxo group, a hydroxyimino group, a lower alkoxyimino group, a lower alkylene group, a lower alkylenedioxy group, a lower alkylsulfinyl group and a lower alkylsulfonyl group;

Substituent group δ is
One group selected from the substituent group β;
A cycloalkyl group substituted with a group selected from substituent group α, substituent group β and substituent group γ;
An aryl group which may be substituted with a group selected from substituent group α, substituent group β and substituent group γ;
A heteroaryl group optionally substituted with a group selected from substituent group α, substituent group β and substituent group γ; and a group selected from substituent group α, substituent group β and substituent group γ The group which consists of the heterocyclyl group which may be substituted by is shown.
However, the atom on the ring A to which R ¹ and R ³ are bonded is adjacent to the atom on the ring A to which R ² is bonded. }
Or a pharmacologically acceptable salt thereof as an active ingredient.   In Claim 1, A is a pyrrole group which may be substituted with two groups selected from substituent group δ and a pyrazole group which may be substituted with one group selected from substituent group δ. A pharmaceutical composition which is a selected trivalent group.   The pharmaceutical composition according to claim 1, wherein A is a pyrrole group which may be substituted with two groups selected from the substituent group δ.   The pharmaceutical composition according to claim 1, wherein A is a pyrrole group. The pharmaceutical composition according to any one of claims 1 to 4, wherein R ¹ is an aryl group optionally substituted with a group selected from substituent group α and substituent group β. The pharmaceutical agent according to any one of claims 1 to 4, wherein R ¹ is a phenyl group or a naphthyl group which may be substituted with a group selected from substituent group α and substituent group β. Composition. In any one selected from claims 1 to 4, R ¹ is a phenyl group which may be substituted with a group selected from Substituent group alpha ¹ and Substituent group beta ^1,
Substituent group α ¹ represents a group consisting of a hydroxy group, a cyano group, a halogen atom, a lower alkoxy group and a halogeno lower alkoxy group,
Substituent group beta ¹ is a pharmaceutical composition showing the group consisting of lower alkyl groups, halogeno-lower alkyl group and a hydroxy lower alkyl group. 5. The substituent according to claim 1, wherein R ¹ is a phenyl group, or a hydroxy group, a cyano group, a halogen atom, a lower alkoxy group, a halogeno lower alkyl group, and a halogeno lower alkoxy group. A pharmaceutical composition which is a phenyl group substituted with a group selected from the group of groups. 5. The method according to claim 1, wherein R ¹ is phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 2,4- Difluorophenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,4,5-trifluorophenyl, 3-chloro-4-fluorophenyl, 3-methoxyphenyl, 3-difluoromethoxyphenyl, 3-trifluoro A pharmaceutical composition which is a methoxyphenyl, 3-trifluoromethylphenyl or 4-fluoro-3-methoxyphenyl group. 5. The method according to claim 1, wherein R ¹ is phenyl, 3-cyanophenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3,4-difluorophenyl, 3. , 4,5-trifluorophenyl, 3-chloro-4-fluorophenyl, 3-methoxyphenyl, 3-difluoromethoxyphenyl, 3-trifluoromethylphenyl or 4-fluoro-3-methoxyphenyl group . 5. The method according to claim 1, wherein R ¹ is phenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3,4-difluorophenyl, 3-chloro-4- A pharmaceutical composition which is a fluorophenyl or 3-trifluoromethylphenyl group. In any one selected from claims 1 to 11, R ² may be substituted with a group selected from Substituent group α and Substituent group beta, 1 or 2 nitrogen atoms A pharmaceutical composition comprising a 5 to 6 membered heteroaryl group. The pharmaceutical according to any one of claims 1 to 11, wherein R ² is a pyridyl group or a pyrimidinyl group optionally substituted with a group selected from substituent group α and substituent group β. Composition. The 4-pyridyl group or 4-pyrimidinyl group according to any one of claims 1 to 11, wherein R ² may be substituted with a group selected from the substituent group α and the substituent group β. A pharmaceutical composition which is a base. In any one of claims 1 to 11, R ² may be substituted at the 2-position with one group selected from substituent group α and substituent group β 4- A pharmaceutical composition which is a pyridyl group or a 4-pyrimidinyl group. The group according to any one of claims 1 to 11, wherein R ² is selected from the substituent group consisting of a methoxy, amino, methylamino, benzylamino, and α-methylbenzylamino group. The pharmaceutical composition which is 4-pyridyl group or 4-pyrimidinyl group optionally substituted at 2-position.   The pharmaceutical composition according to any one of claims 1 to 16, wherein m is 1. 18. The method according to claim 1, wherein R ³ is a group having the formula (IIa), X is an alkylene group having 1 to 4 carbon atoms, and Y is a formula C (R ⁸ a) groups having (R ⁸ b) (R ⁸ a and R ⁸ b are the same or different and are each a hydrogen atom, a hydroxy group, a halogen atom, an alkyl group having 1 to 4 carbon atoms or a carbon number of 1; Represents 4 to 4 alkoxy groups, R ⁸ a and R ⁸ b together represent an oxo group or a methylene group, or together with the carbon atom to which R ⁸ a and R ⁸ b are bonded To form a 3- to 6-membered cycloalkyl group.). 18. The method according to claim 1, wherein R ³ is a group having the formula (IIa), X is a methylene group, and Y is a formula C (R ⁸ a) (R ⁸ b ) Groups (R ⁸ a and R ⁸ b are the same or different and each represents a hydrogen atom, a hydroxy group, a fluorine atom, a methyl group, an ethyl group, a methoxy group, or an ethoxy group, or R ⁸ a and R ^{8 8} b together represents an oxo group or a methylene group, or R ⁸ a and R ⁸ b together with the carbon atom to which they are attached form a cyclopropyl group. A pharmaceutical composition. 18. The method according to claim 1, wherein R ³ is a group having the formula (IIa), X is a methylene group, and Y is a formula C (R ⁸ a) (R ⁸ b ) -Containing groups (R ⁸ a and R ⁸ b are the same or different and each represents a hydrogen atom, a fluorine atom, a methyl group, a hydroxy group or an oxo group). In any one selected from claims 1 to 17, a group R ³ has the formula (IIa), X is a methylene group, a pharmaceutical composition Y is a group having the formula CH ₂ . 18. The method according to claim 1, wherein R ³ is a group having the formula (IIb), the ring B contains one nitrogen atom, and a nitrogen atom, oxygen atom, sulfur 5- or 6-membered heterocyclyl ring optionally containing one atom or group selected from the group consisting of atoms, groups having the formula> SO and groups having the formula> SO ₂ (is the ring saturated? A pharmaceutical composition which is unsaturated; may be condensed with an aryl group, heteroaryl group, cycloalkyl group or heterocyclyl group). 18. A 5- or 6-membered heterocyclyl ring according to any one of claims 1 to 17 wherein R ³ is a group having the formula (IIb) and ring B contains one nitrogen atom. Is saturated or unsaturated; it may be condensed with an aryl group, heteroaryl group, cycloalkyl group or heterocyclyl group). The pharmaceutical composition according to any one of claims 1 to 17, wherein R ³ is a group having the formula (IIb), and ring B is a pyrrolidine ring or a pyrroline ring.   25. In any one selected from Claim 1 thru | or 24, Z is phenylene group, thiophene diyl group, frangiyl group, pyrrole diyl group, oxazole diyl group, thiazole diyl group, thiadiazole diyl group or pyridine diyl group. A pharmaceutical composition.   25. The pharmaceutical composition according to any one of claims 1 to 24, wherein Z is a phenylene group or a thiophenediyl group. In any one selected from Claim 1 thru | or Claim 26,
R ⁵ is a group having the formula CONR ^a R ^b , a group having the formula COR ^c , a group having the formula SO ₂ NR ^a R ^b , a group having the formula SO ₂ R ^c or a group having the formula SOR ^c (wherein R ^a and R ^b are the same or different and each represents a hydrogen atom,
A lower alkyl group which may be substituted with a group selected from substituent group α,
A lower alkoxy group, a lower alkenyloxy group, a cycloalkyl group,
Represents an amino group or a mono- or di-lower alkylamino group,
R ^c represents a lower alkyl group. A pharmaceutical composition. In any one selected from Claim 1 thru | or Claim 26,
R ⁵ is a group having the formula CONR ^a R ^b , a group having the formula SO ₂ NR ^a R ^b , a group having the formula SO ₂ R ^c or a group having the formula SOR ^c (wherein R ^a and R ^b are The same or different, a hydrogen atom, a lower alkyl group, a halogeno lower alkyl group, a hydroxy lower alkyl group, a lower alkoxy lower alkyl group, a lower alkoxy group or a cycloalkyl group;
R ^c represents a lower alkyl group. A pharmaceutical composition. In any one selected from Claim 1 thru | or Claim 26,
R ⁵ is carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-cyclopropylcarbamoyl, N-cyclopentylcarbamoyl, N- (2-fluoroethyl) carbamoyl, N- ( 2-methoxyethyl) carbamoyl,
N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-cyclopropylsulfamoyl, N-cyclopentylsulfamoyl, N- (2-fluoroethyl) ) Sulfamoyl, N- (2-methoxyethyl) sulfamoyl, N-methoxysulfamoyl,
Methanesulfonyl, ethanesulfonyl, propanesulfonyl,
A pharmaceutical composition which is a methanesulfinyl, ethanesulfinyl or propanesulfinyl group. In any one selected from Claim 1 thru | or Claim 29,
A pharmaceutical composition, wherein R ⁶ is 1 to 2 groups selected from the group consisting of a hydrogen atom, a fluorine atom and a methoxy group. In any one selected from claims 1 to 29, R ⁶ is a pharmaceutical composition is a hydrogen atom. In any one selected from claims 1 to 31, R ⁷ is a hydrogen atom, a pharmaceutical composition is 1 to 2 groups selected from the group consisting of hydroxy group and a lower alkyl group. In any one selected from claims 1 to 31, R ⁷ is A pharmaceutical composition is a hydrogen atom. 34. The pharmaceutical composition according to any one of claims 1 to 33, wherein the compound having the general formula (I) is represented by any one of the following general formulas:

(In the formula, R ⁴ and R ⁴ ′ are the same or different and each represents a hydrogen atom or a group selected from the substituent group δ). 34. The pharmaceutical composition according to any one of claims 1 to 33, wherein the compound having the general formula (I) is represented by any one of the following general formulas:

(In the formula, R ⁴ and R ⁴ ′ are the same or different and each represents a hydrogen atom or a group selected from the substituent group δ). A pharmaceutical composition according to claim 1, wherein the compound having general formula (I) is selected from:
4- [1- (4-Carbamoylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole ,
3- [1- (4-Carbamoylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -5- (4-fluorophenyl) -4- (pyridin-4-yl) -1H-pyrazole ,
2- (4-Fluorophenyl) -4- [1- [4- (N-methylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole,
4- [1- [4- (N-ethylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridin-4-yl) ) -1H-pyrrole,
4- [1- [4- (N-cyclopropylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4- Yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-isopropylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-propylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) ) -1H-pyrrole,
4- [1- [4- [N- (2-Fluoroethyl) carbamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- ( Pyridin-4-yl) -1H-pyrrole 4- [1- [4- (N-cyclopentylcarbamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) ) -3- (pyridin-4-yl) -1H-pyrrole,
4- [1- [4- [N- (Ethoxycarbonylmethyl) carbamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine -4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole,
4- [1- [4- (N-ethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4 -Yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-propylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (N-isopropylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4 -Yl) -1H-pyrrole,
2- (3-Chloro-4-fluorophenyl) -4- [1- [4- (N-methylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (Pyridin-4-yl) -1H-pyrrole,
4- [1- [4- (N-cyclopropylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine- 4-yl) -1H-pyrrole,
4- [1- [4- [N- (2-fluoroethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- ( Pyridin-4-yl) -1H-pyrrole,
4- [1- [4- (N, N-dimethylsulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine -4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- [N- (2-methoxyethyl) sulfamoyl] phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- ( Pyridin-4-yl) -1H-pyrrole,
4- [1- [4- (N-ethoxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine-4 -Yl) -1H-pyrrole,
4- [1- [4- (N-allyloxysulfamoyl) phenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -2- (4-fluorophenyl) -3- (pyridine- 4-yl) -1H-pyrrole 2- (4-fluorophenyl) -4- [1- (4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine -4-yl) -1H-pyrrole,
2- (3-Chloro-4-fluorophenyl) -4- [1- (4-methanesulfonylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl ) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- (4-methanesulfinylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H- Pyrrole,
2- (3-Chloro-4-fluorophenyl) -4- [1- (4-methanesulfinylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridin-4yl) -1H-pyrrole,
4- [1- (4-Acetylphenethyl) -1,2,3,6-tetrahydropyridin-4-yl] -2- (3-chloro-4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
2- (3-Chloro-4-fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-methylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydro Indolizine-7-yl] -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- (4-carbamoylphenyl) -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4-fluorophenyl) -3 -(Pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-methylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- [4- (N-ethylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4- Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- [4- (N-benzylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4- Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- [4- (N-cyclopropylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl] -2- (4 -Fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
4-[(2S, 8aS) -2- [4- [N- (2-fluoroethyl) carbamoyl] phenyl] -1,2,3,5,6,8a-hexahydroindolizin-7-yl]- 2- (4-fluorophenyl) -3- (pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-propylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- (N-isopropylcarbamoyl) phenyl] -1,2,3,5,6,8a-hexahydroindolizine-7 -Yl] -3- (pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4-[(2S, 8aS) -2- [4- [N- (2-methoxyethyl) carbamoyl] phenyl] -1,2,3,5,6,8a-hexa Hydroindolizin-7-yl] -3- (pyridin-4-yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (2-methoxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4- Yl) -1H-pyrrole,
2- (4-Fluorophenyl) -4- [1- [4- (2-hydroxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- (pyridine-4- Yl) -1H-pyrrole,
2- (3-Chloro-4-fluorophenyl) -4- [1- [4- (2-methoxyethyl) sulfonylphenethyl] -1,2,3,6-tetrahydropyridin-4-yl] -3- ( Pyridin-4-yl) -1H-pyrrole and 2- (3-chloro-4-fluorophenyl) -4- [1- [4- (2-hydroxyethyl) sulfonylphenethyl] -1,2,3,6- Tetrahydropyridin-4-yl] -3- (pyridin-4-yl) -1H-pyrrole.   The pharmaceutical composition according to any one of claims 1 to 36, which is used for suppressing the production of inflammatory cytokines.   37. The pharmaceutical composition according to any one of claims 1 to 36, which is used as an antipyretic / analgesic agent having an inhibitory action on inflammatory cytokine production.   The pharmaceutical composition according to any one of claims 1 to 36, which is used as an anti-inflammatory agent.   The pharmaceutical composition according to any one of claims 1 to 36, which is used as a prophylactic or therapeutic agent for rheumatoid arthritis.   The pharmaceutical composition according to any one of claims 1 to 36, which is used as a prophylactic or therapeutic agent for osteoarthritis.   The pharmaceutical composition according to any one of claims 1 to 36, which is used as a prophylactic or therapeutic agent for allergic diseases.   The pharmaceutical composition according to any one of claims 1 to 36, which is used as an agent for preventing or treating osteoporosis.   The pharmaceutical composition according to any one of claims 1 to 36, which is used as a prophylactic or therapeutic agent for arteriosclerosis.   The pharmaceutical composition according to any one of claims 1 to 36, which is used as a prophylactic or therapeutic agent for tumors.   The pharmaceutical composition according to any one of claims 1 to 36, which is used as a prophylactic or therapeutic agent for ischemic heart disease.   The pharmaceutical composition according to any one of claims 1 to 36, which is used as a preventive or therapeutic agent for sepsis, psoriasis, Crohn's disease, ulcerative colitis, diabetes or hepatitis.   Use of a compound according to any one of claims 1 to 36 or a pharmacologically acceptable salt thereof for the manufacture of a pharmaceutical composition.