JPH02270873A - Imidazopyridine compound and production thereof - Google Patents

Abstract

NEW MATERIAL:8-{2-Methyl-6-[(S) or (R)-2-hydroxypropionyl amino]benzylamino}-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine and its salt. USE:A drug. An antiulcer agent and acid-secretion suppressing agent. Useful as a remedy for gastric ulcer, duodenal ulcer, anastomatic ulcer, acute or chron ic gastritis, cholera, etc. PREPARATION:The novel substance such as the compound of formula I can be produced by reacting a novel compound of formula II or its salt with a compound of formula III (R is protected OH; X is halogen) and subjecting the resultant compound of formula N or its salt to elimination reaction of the hydroxy-protecting group.

Description

Detailed Description of the Invention "Industrial Application Field" This invention has anti-ulcer effect and acid secretion suppressing effect, such as gastric ulcer, duodenal ulcer, anastomotic ulcer, Zollinger-Ellison syndrome, acute gastritis, chronic gastritis, A pair of optical isomers of imidazopyridine compounds, i.e., 8-[2-methyl-
6-((S)-2-hydroxypropionylamino)bensylamino]-3-(2-propynyl)-2-methylimidazo[1,2-a]copyridine and 8-[2-methyl-6-((R) -2-hydroxypropionylamino)hensylamino]-3-(2-propynyl)-2-methylimidazo[1,2-a]copyridine and its salts,
The present invention relates to a method for producing the same, as well as anti-ulcer agents and acid secretion inhibitors containing the same as an active ingredient, and is useful in the pharmaceutical field.

“A means to solve problems.

A pair of optical isomers of the imidazopyridine compound of the present invention is represented by the following structural formulas (I8) and (Ib>).

[Compound (I8)”8-[2-methyl-6-((S)-
2-Hydroxypropionylamino)benzylamino]
-3-(2-propynyl)-2-methylimidazo[1,
2-a copyridine], and [Compound (Ib): 8-[
2-Methyl-6-+(R)-2-hydroxypropionylamino)benzylamino]-3-(2-propynyl)
-2-methylimidazo[1,2-a copyridine].

According to this invention, the target compounds (I8) and (I b)
can be manufactured by the following manufacturing method.

(wherein R means a protected hydroxy group and X means a halogen).

Suitable salts of the target compounds (8) and (Ib) are commonly used non-toxic salts, such as acetate, maleate, tartrate, methanesulfonate, Hensensulfonate,
Organic acid salts such as formate and toluene sulfonate; inorganic acid salts such as hydrochloride, hydrobromide, sulfate, and phosphate; salts with amino acids such as arginine, aspartic acid, and glutamine; Can be mentioned.

Suitable "protected hydroxy groups" for R include, for example, formyloxy, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, valeryloxy, isovaleryloxy, pivaloyloxy, hexanoyloxy, etc. Examples include lower alkanoyloxy groups having 1 to 6 (preferably 1 to 4) subatomic atoms, such as acyloxy groups such as sulfonyloxy groups such as mesyloxy and tosyloxy.

Suitable "halogens" include fluorine, chlorine, bromine and iodine.

The reaction in the method for producing the target compounds (Ia) and (Ib) or their salts can be carried out in substantially the same manner as disclosed later in the specification or as described in the examples.

The starting compound (I) or its salts are new and can be produced, for example, by the method described in Section 1 disclosed later in the specification.

"Effects of the Invention" In order to demonstrate the usefulness of the target compound of this invention, pharmacological test results are shown below.

Effects on gastrin-stimulated gastric acid secretion in He1denhain gastrointestinal dogs: A He1danhain gastrointestinal dog, which had been fasted for 18 to 24 hours in advance, was fixed on a suspension type fixation stand while awake.

10g of tetragastrin solution dissolved in physiological saline /
kg/hr to Q, lml/kg/
Cephalic vein (Cephalic vei) with a volume of min.
n) Continuous infusion. Collect gastric juice every 15 minutes, and after the gastric juice volume becomes constant (usually within 2 hours), administer the drug at 1 mQ/
It was administered orally in a volume of kg.

Gastric juice was collected every 15 minutes for up to 3 hours after administration. After measuring the volume of each gastric juice, using 0.1 M NaOR,
Titrated to pH 7.0.

The amount of gastric acid secretion was expressed as μEq)l''/15mln.The effect of the drug was expressed as the rate of change in the amount of gastric acid secretion before and after administration.

Test compound (1) 8-[2-methyl-6-((S)-2-hydroxypropionylamino)benzylaminoco-3-(2-
propynyl)-2-methylimidazo[1,2-a]pyridine.

Test Results: Maximum inhibition rate (%) at a dose of 3.2 mg/kg As is clear from the above test results, the target compound of the present invention is useful as an anti-ulcer agent and an acid secretion inhibitor.

For therapeutic purposes, the compounds of this invention may be mixed with pharmaceutically acceptable carriers such as organic or inorganic solid or liquid excipients suitable for oral or parenteral administration containing said compounds as active ingredients. It can be used in the form of pharmaceutical preparations. Pharmaceutical preparations are capsules, tablets, dragees, solutions, suspensions, emulsions and the like. If desired, auxiliary agents, stabilizers, wetting agents or emulsifiers, buffers and other commonly used additives may be included in the above formulations.

Although the dosage of the compound will vary depending on the age and condition of the patient, the compounds of this invention are administered at an average daily dose of about 5 mg, 1
0mg, 50mg, 100mg, 250+ng, 50
0mg.

A dose of 1000 mg is effective in treating ulcers and diarrheal diseases. Generally, amounts between 1 mg/individual and about 2000 mg/individual may be administered per day, although higher amounts may be administered per day.

1 Example” The present invention will be explained below according to production examples and examples.

Production Example 1 2.3-diaminopyridine (62.8g) and 3-medyloquin-5-hexyn-2-one (109.5g)
The mixture in methanol (126111Q) is refluxed for 20 hours. After methanol is distilled off under reduced pressure, an aqueous sodium hydrogen solution is added to the residue, then the mixture is extracted with ethyl acetate, washed with water and an aqueous sodium chloride solution, and the solvent is distilled off under reduced pressure. Silica gel (310g) was added to the residue.
The product was subjected to column chromatography using a mixture of methylene chloride and acetonitrile and eluted with a mixture of methylene chloride and acetonitrile. The eluates containing the target compound are combined and the solvent is distilled off under reduced pressure. The residue is suspended in diethyl ether and the resulting precipitate is collected by filtration to obtain 18.42 g of 8-amino-3-(2-propynyl)-2-methylimidazo[1,2-a]copyridine.

The solvent of the filtrate was distilled off, and the residue was purified with silica gel (120 g
) and eluted with a mixture of methylene chloride and methanol. The eluates containing the target compound are combined and the solvent is distilled off under reduced pressure. The residue was suspended in diethyl ether and the precipitate was collected by filtration to obtain 8-amino-3-(2--7'rovinyl)-2-methylimidazo[1,2-a copyridine (14.10 g).

IR (Sujoor): 3410. 3275.
3170. 1625°1550 cm 'NMR (CDC13,S)' 2.05 (IHL
t, J=3)1z), 2.43(3H,s>, 3.7
2 (2H, d, J=3)1z), 4.51 (2H
.

broad s), 6.27 (LH, dd, J=
IHz and 7Hz).

6.63 (IH, t, J=7)1z), 7.49
(1)1. dd, J = 1) 1z and 7Hz) 2-Methyl-6 produced by reacting 6-aminobenzaldehyde with methyl chloroformate
-Medoxycarponylaminobenzaldehyde (193
mg) and triethylamine'/ (1,4111Q
) to a mixture of titanium tetrachloride (0.5 M) in methylene chloride (3.6 mA).

Add 2.5 ml dropwise at 10° C. under nitrogen atmosphere. After stirring the mixture at the same temperature for 4 hours, chloroform and water are added to the mixture. Insoluble materials are removed by filtration, and the organic layer is separated and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in methanol (42 mg).

Sodium borohydride (44 mg) is added portionwise to the mixture and the mixture is stirred for 4 hours.

Pour the mixture into water and extract with chloroform.

The organic layer is dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The residue was triturated with diethyl ether to give 8-(2
-Methyl-6-medoxycarponylaminobenzylamino)-3-(2-propynyl)-2-methylimidazo[
1,2-a copyridine (185 mg) is obtained.

mp' 149-150℃ IR (X9-L): 3370. 3290.
1730. 1610°1590 cm-1 NMR (DMSO-ds, 8)' 2.30 (3
H,s), 2.36 (3H1s), 2.93 (1
)1. t, J=3Hz>, 3.62 (3H,s).

3.86 (2H, d, J=3Hz>, 4.35
(2H, d, J=5)1z).

5.43 (1)1. t, J=5Hz), 6.25
(IH, d, J: 87.5Hz).

6.70 (IH, t, J=7.5Hz), 6.
90-7.30 (3)1. m＞.

7.5+4 (1)1. d, J=7.5Hz),
9.03 (1)1. Broad S) Tsuyoshi 1 E1 Methyl chloroformate (0,416g) in methylene chloride (
1nn) solution was added to 2-amino-6-methylbenzyl alcohol (0,549g) and pyridine (0,364g).
The mixture was added dropwise to a methylene chloride (10 mQ) solution under water cooling. After stirring for 1 hour, the mixture is poured into IN hydrochloric acid and extracted with methylene chloride. The extract is washed with water, dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The crystalline residue was washed with n-hexane and dried to give 2-methyl-6-medoxycarponylaminobenzyl alcohol (0,6416).
get.

mp: 111-113℃ IR (streak seal): 3450. 3260.
1685. 1602°1580, 1540 cm' NMR (CDCI3.δ): 2.36 (3H,s
), 2.46 (IH, t.

J=6Hz), 3.73 <3)1. s),
4.67 (28,d,,7=6Hz).

6.87 (LH, d, J=7.5Hz), 7.1
1 <LH, t.

J=7.5Hz), 7.47 (IH, d, J=7
．． 51(z), 7.40-7.70 (11(,
2-methyl-6-tertiary-butoxycarbonylaminobenzyl alcohol is obtained in the same manner as in Production Example 3.

mp: 96-98℃ IR (streak seal): 3450. 33
20, 1695, 1600. 1580.

1520 cm"-1 NMR (CDCI 8): 1.50 (9H.
s), 2.40 (2H, s).

3' 4, 73 (2H.d, J=6Hz'), 6.80-
7.63 (4H, m) jt [dispersion of 2-methyl-6-medoxycarbonylaminobenzyl alcohol (290 ml) was added to the suspension of thionyl chloride (1
1. 46 mQ) is added dropwise at room temperature and the mixture is stirred for 2 hours.

After distilling off the solvent under reduced pressure, n-hexane is added to the residue to form a precipitate. The precipitate was collected by filtration and dried to obtain 2-methyl-6-medoxycarponylaminohenzyl chloride (28.26 g).

IR (Stripe Seal>: 3975.16
80. 1595. 1580.

1520 am-1 NMR (CDCI3.δ): 2.42 (3H.
s), 3.78 (3H.s), 4,65 (2H.s), 3.78 (3H.s), 4,65 (2H.s)
,s), 6.55-7.00 (1)1. Broad S).

7,00 (LH.ddj=2Hz and 7.51(z
), 7.25 (LH, t, J=7.5Hz), 7.
60 (LH, dd, J = 7.5 Hz>1) In the same manner as in B, 2-methyl-6-tertiary butquine carbonylaminobenzyl chloride is obtained.

mp: 75-76℃ 1, R (streak seal): 3355. 1
685, 1600. 1582.

1510 cm-' NMR (CDCI δ): 1.52 (91
(,s), 2.42 <3H,s).

3゛4, 67 (2H.s), 6.60 (LM.
Broad s), 7.0 <18.

d. J=7.5Hz>, 7.40 (IH, t.J
=7.5Hz>, 7.80(1)1,d,J=7.
5) 1z) Shake 2,3-diaminopyridine (1.09 g) in methanol (z2mQ) solution, add 2-methyl-6-medoxycarponylaminobenzyl chloride (2.14 g) and I! Potassium acid (1.38 g) is added at room temperature and the mixture is stirred for 1.5 hours. Insoluble matters are removed by filtration, and methanol in the filtrate is distilled off under reduced pressure. Pour the residue into silica gel (30g)
Column chromatography using a mixture of chloroform and methanol (100:1) gives a crystalline product. The crystals are triturated with diisopropyl ether to give 2-amino-3-(2-methyl-6-medoxycarponylaminobenzylamino (1.44 g)).

mp: 176-178℃ IR (streak seal): 3445. 32
90. 3125, 1730, 1645.

1590 cm"" NMR (DMSO-d6, δ) +
2.33 (3H.S), 3.58 <3)1
.

s), 4.08 (2H.d, J=5)1z), 4
．． 52 (LH, t.

J=5Hz>, 5.40 (2)! ,s), 6.3
7-6, 57 (1) 1, m).

6, 67-6, 82 (IH.+++), 6.90-
7.40 (4H, m).

8, 77 (IH.s) Production Example 8 2-Amino-3-(2-methyl-6-medoxycarbonylaminobenzylamino (180 mg) and 3-mesyloxy-5-hexyn-2-one (120 mg) (' ) meta / - le (
0. 36mQ) and chloroform (0.3
6IIQ) Reflux the warm mixture for 20 hours. After cooling, chloroform is added to the mixture and the mixture is washed with aqueous sodium carbonate solution and water. The solvent is evaporated under reduced pressure and the residue is subjected to column chromatography using silica gel (4 g) and eluted with chloroform to give an oily product. The residue was triturated with diethyl ether to give 8-(2-methyl-6-medoxycarponylaminobenzylamino).
-3-(2-propynyl)-2-methylimidazo[1.
2-a] Copyridine (127 mg) is obtained.

mp: 149-150℃ IR (streak seal): 3370, 32
90, 1730, 1610, 1590.

1560, 1540 cm-1 NMR (CDCl2.8): 2.06 (LH,
tJ=3)1z), 2.36(6H,s), 3.
66 (3H, s), 3.73 (2H, d.J-
3Hz>.

4, 35 (2H.d, J=4.5Hz), 4.8
5 (IH.t.

J=4.5Hz), 6.35 (LH.d.J=7
Hz), 6.76 (18.

t, J=7Hz), 6.98 (LH.d, J=7
Hz>, 7.25 (LH.

t. J=7Hz), 7.43-7.85 (3H.
m) Production Example 9 8-(2-Methyl-6-medoxycarponylaminobenzylaminol)-2-methylimidazo[1.2-acopyridine(9
2.2 g) of methylene chloride (920 mQ) was added 20-30 g of trimethylsilyl E-cyto (724 mQ).
Add dropwise at °C. After refluxing the mixture for 5 hours, the oil bath was removed and methanol (90 mQ) was added dropwise under reflux. After stirring for 40 minutes at room temperature, the solvent is distilled off under reduced pressure. The residue is poured into saturated aqueous sodium bicarbonate solution and extracted with chloroform. The chloroform layer is separated, washed with water, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was triturated with ethanol to give 8-(2-methyl-6-aminobenzylamino)-3-(2-propynyl)-2-methylimidazo[1.2-acopyridine. (61.8 g) is obtained.

mp: 199-201℃ IR (Stripe Seal) “3420, 3310
, 3290, 3220, 1620.

1545 cm' NMR (DMSO-d6.S): 227 (6H1s),
291 (IH.

t, J=3Hz>, 3.85 (2H.d, J=3H
z>, 4.30 (2H.

d. J: 5Hz), 4.98 (2H, s), 5.
61 (1M, t.

J: 5Hz>, 6.23-7.03 (5H, m),
7.60 (IH, d.

2-Methyl-6-tert-butoxycarbonylaminobenzyl was added to a suspension of 2,3-diaminopyridine (5.0 g) and potassium carbonate (6.3 g) in nomethanol (100 mQ). Add chloride (11.7 g) and stir at room temperature for half an hour. The mixture is poured into water and extracted with ethyl acetate. The organic layer is separated, washed with water, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was triturated with dioxane to give 2-amino-3-(2-methyl-6-tert-butoxycarbonylaminobenzylamino)pyridine (10.65 g)-20-. obtain.

mp: 151 (53℃ IR (Sujoor): 3440, 33
90, 3320. 3280, 3150.

1718, 1645. 1600. 1585, 1
545.

1520 cm-1 NMR (CDCl2, δ)' 1.46 (9H,
s), 2.37 (3H.s).

3, 31 (LH.t, J=5Hz), 4.19 (
2)! , d, J=5Hz).

4, 26 (2H.s), 6.73-6.79 (I
H, m>, 6.99 (2H, t.J=8Hz>, 7
．． 24 (IH, d, J=8)1z), 7.37 (I
H. s), 7.62-7.69 (2) 1, m> Production Example 11 2-amino-3-(2-methyl-6-tert-butoxycarbonylaminobenzylaminodine (0.9 g) and 3- Mesyloxy-5-hexyn-2-one (0.52
A solution of g) in methanol (1.8 mQ) is refluxed for 40 hours. The mixture is diluted with aqueous sodium bicarbonate solution and extracted with methylene chloride. The organic layer is separated and dried over magnesium sulfate. The solvent is removed under reduced pressure. The residue is dissolved in ethanol (3.6 mQ) and to this is added dropwise 20% ethanolic hydrogen chloride (4 mp). After stirring the mixture for 5 hours, the solid that forms is filtered off. The resulting crystals are partitioned between aqueous sodium carbonate and chloroform. The organic layer is separated and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was triturated with ethanol to give 8-(2-
0.34 g of methyl-6-aminobenzylamino)-:3-(2-propynyl)-2-methylimidazo[1,2-a]copyridine) is obtained.

NMR (DMSO-d6.δ): 2.27 (6
H,s), 2.91 (LH.

t, c3Hz), 3.85 (2H, d, t3H
z), 4.30 (2) 1°d,, C3Hz),
4.98 (2H,s), 5.61 (I
H,t.

J=5Hz), 6.23-7.03 (5H, m>,
7.66 (LH, d.

Example 1 8-(2-methyl-6-aminobenzylamino)-3-
(2-propynyl)-2-methylimidazo[1,2-a
l pyridine (6.11 g) in chloroform (183 mA
) To the solution, (5)-2-acetoxypropionyl chloride (3.16 g) is added dropwise at 5° C. and the mixture is stirred for 40 minutes. The solvent is removed under reduced pressure. 8-[2-Methyl-6-((S)-2-acetoxypropionylamino)benzylamino]-3·-(2-propynyl)-2-
Methanol (244 mQ) was added to the methylimidazo[1,2-a]copyridine residue, and potassium carbonate (4,
An aqueous solution (13 mQ) of 42 g) was added dropwise at room temperature. After stirring the mixture for 45 minutes, the precipitate was collected by filtration and dried to give 8-[
2-Methyl-6-((S)-2-hydroxypropionylamino)benzylamino]-3-(2-propynyl)
-2-methylimidazo[1,2-a copyridine (7,4
0g).

mp-196-202°C (decomposition) IR: 3375. 3230.
1690. 1600. 1585°1560, 153
0 cm-1 NMR (CDCl2.δ): 1.28 (3H, d
, J=7Hz>, 2.11 (IH, t, J=3Hz)
, 2.23 (3H,s), 2.36 (3H,s
).

3.63 (2H, d, J=3Hz>, 4.14-4
．． 37 (3H, m>.

5.20 (LH, t, J=5Hz>, 6.07 (
II(,d,J=7)1z).

6.59 (IH, t, J=7Hz>, 7.03
(IH, d, J=7Hz).

7.22 (LH, d, J=8)fz), 7.27
(IH, dJ=7Hz).

7.62 (18,d, J=8Hz), 9.93
(IH, s) [α Koni2=-75,8° [C・1
．． 11. CHCl3:EtOH(99,5ho,5)]
East JUΔ main fire group■ Similarly to Yu, 8-[2-methyl-61(R>
2-Hydroxypropionylamino)benzylamino]
-3-(2-propynyl)-2-methylimidazo[1,
2-a Copyridine is obtained.

mp: 180 (97℃ (decomposition) IR (nujol): 3390. 3330.
3300. 1680°1560 cm-1 NMR (CI) C13, δ): 1.3 (31(,
d, J=6)1z), 2.06(IH,t, J=31
(z), 2.25 (3H,s), 2.36 (3
)1. s).

3.60 (28,d,, J:3Hz>, 4.10-
4.53 (3)1. m＞.

5.20 (IH, d, J-5) 1z), 6.1
0 <IH, dj=7.5)1z).

6.60 (18,t, J=7Hz), 6.99 (
LH, d, J-7, 51 (z).

7.16 (LH, d, J=7Hz), 7.34 (
11, d, J=7Hz).

7.67 (LH, d, , T=7.5Hz>, 9.5
2 (LH, s) [α] Otsu 4・+58.3° [C=1.
02. CHCl3:Et, 0H (99, sho, s)
]8-[2-Methyl-6-((S)-2-hydroxypropionylamino)pencylamino]-3-(2-propynyl)-2-methylimidazo[1°2-a-copyridine (51,58 g) To a moderately warm mixture of ethanol (277 mA) was added 514N ethanolic hydrogen chloride (26.7 mQ).
) is added dropwise at room temperature. After stirring the mixture for 1 hour, the resulting solid was collected by filtration to give 8-[2-methyl-6-f(S)
2-Hydroxypropionylamino)benzylamino]
-3-(2-propynyl)-2-methylimidazo[1,
2-a] Copyridine hydrochloride (46 g) is obtained.

ITlp: 217-218°C [CL: l end-15.9° (C=1.0.) 120>
Optical purity = 99.02X ee (chiral,
I (PLC) IR (Nuji 1-A): 3260.
3120. 3050. 2750. 2700°2
660, 1675.1620.1585°1510 c
m-1 NMR (DMSO-d6.δ)' 1.2
3 (3)1. d, J=7.8Hz).

2.41 (38,s), 2.48 (3H,
s), s, t6 (18, t.

J=2.6Hz), 4.06-4.16 (3H, m
>, 4.38 (2H, d.

J=3.9)1z), 6.80 (IH, Broad s), 7.03 (LH, d.

J=7.90>, 7.09 (LH, d, J=7.
20>, 7.25 (IH.

t, J=7.90), 7.37 (IH, t, J
=6.50), 7.50(1)1. d, J=7.2
0>, 8.02 (IH, d, J engineering 6.50),
9.50 (IH, s), 14.82 (18,
Broad S) Elemental analysis Calculated value as C2°H2, ClN402: C: 63.99. H: 6.10
．． N-13,57°C1: 8.59 Actual value: C: 63.85. H: 6.15. N
; 13.42°C1: 8.82 Example 4 8-[2-methyl-6-((S)-2-hydroxypropionylamino)benzylaminoco-3-(2-propynyl)-2-methylimidazo[ 1゜2-a Copyridine (
15g) of ethanol (350ml+) at medium temperature,
methanesulfonic acid (2,59 g) in ethanol (25 m
Q) Add the solution dropwise at room temperature and then stir the mixture for 4 hours. The resulting solid was collected by filtration to give 8-[2-methyl-6i
(S)-2-hydroxypropionylamino)benzylamino]-3-(2-propynyl)-2-methylimidazo[1,2-a]copyridine methanesulfonate (14
, 85 g).

mp: 208-214℃ [α 0=-12,7° (C=1.0.H2O)
Optical purity = 96.04X ee (chiral,
HPLC) IR: 3290. 3
240. 2690. 1680. 1580°151
0 cm”” NMR (DMSO-d6.δ>: 1.20 (3H
, d, J-6,8Hz>.

2.26 (3)! , s), 2.40 (3)1. s
), 2.49 (3H,s).

3.17 (IH, t, J=2.5Hz>, 4.04
-4.13 (3)1. m＞.

4.35 (2H, d, J=3.9)1z), 6
．． 16 (IH, Broad s).

7.07-7.16 (2)1. m>, 7.30 (
LH, t, J = 8Hz).

7.40 (IH, t, J=7)1z), 7.55
(IH, d, J=7Hz).

8.07 (IH, d, J=7Hz>, 9.47 <
1)1. s), 13.94 (IH, Broad S) Elemental analysis C23H28N40. Calculated value as S:
C: 58.46. H: 5.97. N: 11.
86°S: 6.78 Actual value: C: 58.64. H: 5.97. N
: 11.38°S: 6.72 Patent applicant Fujisawa Pharmaceutical Co., Ltd.

Claims (1)

[Scope of Claims] 1) 8-[2-methyl-6-{(S)-2-hydroxypropionylamino}benzylamino]-3-(2-propynyl)-2-methylimidazo[1,2-a ]pyridine, and 8-[2-methyl-6-{(R)-2-hydroxypropionylamino)benzylamino]-3-(
2-propynyl)-2-methylimidazo[1,2-a]
An imidazopyridine compound selected from the group consisting of pyridine and salts thereof. 2) 8-[2-Methyl-6-{(S)-2-hydroxypropionylamino}benzylamino]-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine The compound described in 1). 3) (i) 8-[2-Methyl-6-{(S)-2-(protected hydroxy)propionylamino}benzylamino]-3-(2-propynyl)-2-methylimidazo[1,2 -a] Pyridine or its salt is subjected to a hydroxy protecting group elimination reaction to obtain 8-[2-methyl-6-{(
(ii) 8-[2-methyl -6-{(R)-2-(protected hydroxy)propionylamino}benzylamino]-3-(2-propynyl)-2-methylimidazo[
1,2-a]pyridine or a salt thereof is subjected to a hydroxy protecting group elimination reaction to obtain 8-[2-methyl-6-{(R
)-2-hydroxypropionylamino}benzylamino]-3-(2-propynyl)-2-methylimidazo[
By obtaining 1,2-a]pyridine or its salts, 8-[2-methyl-6-{(S)-2-hydroxypropionylamino}benzylamino]-3-(2-propynyl)-2-methyl imidazo[1,2-a]pyridine and 8-[2-methyl-6-{(R)-2-hydroxypropionylamino}benzylamino]-3-(2-
A method for producing an imidazopyridine compound, which comprises obtaining a compound selected from the group consisting of (propynyl)-2-methylimidazo[1,2-a]pyridine or a salt thereof. 4) An anti-ulcer agent and an anti-acid secretion inhibitor containing the compound or salt thereof according to claim 1) as an active ingredient.