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Pyrrolopyridazine compound

A technology of pyridazine derivatives and pyrrole, applied in the field of pyrrolopyridazine derivatives, can solve problems such as ulcer recurrence

Inactive Publication Date: 2006-11-22
SANKYO CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above agents have excellent therapeutic effects on ulcerative diseases, ulcers may recur after interruption of treatment

Method used

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  • Pyrrolopyridazine compound
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0168] 3-acetyl oxymethyl-7- (4-fluofluorobyloxy) -2-methyl-1 - [(1S, 2S) -2-methylcyclopropylmethyl] pyrrole [2, 3-D ]

[0169] Take 7- (4-fluorosyloxy) -2,3-dimethyl-1 - [((1S, 2S) -2-methylcyclopropylmethyl] pyrrol [2, 3-D) at room temperature. ] 哒 0.679 g (2.00 mmol) of acetic acid (40 mL) is added to 6.58 g (12.0 mmol) of ammonium nitrate (12.0 mmol), and then stirred at 60 ° C for 3 hours. The reaction mixture was poured into water, extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: hexane / ethyl acetate = 1 / 1), the resulting oil was crystallized with hexane to obtain 0.225 g (28%) of the pale yellow crystal title compound. .

[0170] Melting point: 122-123 ° C

[0171] Mass spectrometry (CI, M / Z): 398 (M + +1).

[0172] NMR spectrum (CDCL 3 , ΔPPM): 0.13-0.20 (m, 1H), 0.37-0.44...

Embodiment 2

[0174] 7- (4-fluorobenoxy) -3-hydroxymethyl-2-methyl-1 - [(1S, 2S) -2-methylcyclopropylmethyl] pyrrol [2, 3-D] Pyridazine

[0175] Take 7- (4-fluorosyloxy) -2,3-dimethyl-1 - [((1S, 2S) -2-methylcyclopropylmethyl] pyrrol [2, 3-D) at room temperature. ] 哒 67.9 g (200 mmol) of acetic acid (800 mL) is added to 1,329 g (600 mmol) of ammonium nitrate, and then stirred at 55 ° C for 8 hours. Water was added to the reaction mixture, extracted with ethyl acetate, and the extract was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was added to the residue (500 mL) and 2N aqueous lithium hydroxide (160 mL), stirred at room temperature for 40 minutes. The reaction mixture was neutralized with 1 N hydrochloric acid, and methanol was evaporated under reduced pressure. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and ...

Embodiment 3

[0181] 7- (4-fluorobenoxy) -3-formyl-2-methyl-1 - [(1S, 2S) -2-methylcyclopropylmethyl] pyrrole [2, 3-D] 哒Namazine

[0182] Take 7- (4-fluorosyloxy) -3-hydroxymethyl-2-methyl-1-[(1S, 2S) -2-methylcyclopropyl methyl] pyrrole [2, "at room temperature. The activation of manganese dioxide 472 g (5.43 mol) was added to 64.3 g (181 mmol) of dichloromethane (900 mL) solution, and then stirred at room temperature for 18 hours. The reaction mixture was filtered through Celite (trade name), and the filtrate was concentrated under reduced pressure, and the obtained crude crystallization (45.7 g) was washed with ethyl acetate and hexane to give 44.3 g (69%) of the pale yellow crystallization title compound.

[0183] Melting point: 138.5-139.5 ° C

[0184] Mass spectrometry (CI, M / Z): 354 (M + +1).

[0185] NMR spectrum (CDCL 3 , ΔPPM): 0.19-0.26 (M, 1H), 0.40-0.77 (M, 1H), 0.71-0.78 (M, 1H), 0.84-0.91 (m, 1H), 0.92 (D; J = 5.9 Hz, 3H ), 2.75 (S, 3H), 4.19 (DD; J = 14.6 Hz, 7.1 Hz, 1H), 4.67...

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Abstract

Pyrrolopyridazine derivatives represented by general formula (I) or pharmaceutically acceptable salts thereof, in formula (I) R1 is C2-C6 alkenyl, halogenated C2-C6 alkenyl, optionally substituted C3 -C7 cycloalkyl or optionally substituted C3-C7 cycloalkyl -C1-C6 alkyl; R2 is C1-C6 alkyl; R3 is hydroxymethyl, C2-C6 aliphatic acyloxymethyl, optionally substituted C6-C10 arylcarbonyloxymethyl, C1-C6 alkoxycarbonyloxymethyl, formyl, carboxyl, C1-C6 alkoxycarbonyl or optionally substituted C6-C10 aryloxycarbonyl; R4 is optionally substituted C6-C10 aryl; A is imino, oxygen or sulfur. The pyrrolopyridazine derivative has excellent gastric acid secretion inhibitory effects, gastric mucosa protective effects, etc., and can be effectively used as a drug, especially as a preventive drug and a therapeutic drug for ulcer diseases. ∴

Description

Technical field [0001] The present invention relates to a pyrrolidazine derivative or a pharmaceutically acceptable salt thereof, a pharmaceutically acceptable salt containing a pyrrolidine derivative or a pharmaceutically acceptable salt thereof as an active ingredient (especially prevention or treatment of ulcerative diseases) Compositions), pyrrolidine derivatives or pharmacologically acceptable salts in the manufacture of pharmaceutical compositions (especially prevention or therapeutic compositions of ulcerative diseases), or involve prevention or treatment of diseases (especially ulcerative The method of the disease includes the administration of a thermosal animal (especially human), a pharmacodynamic amount of a pyrrolidine derivative or a pharmacological acceptable salt thereof. Background technique [0002] Digest ulcers have been considered to imbalance between the attack factors and defense factors of the gastric mucosa. It is useful for prevention and treatment of ul...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/5025A61P1/04C07D207/00C07D237/00
CPCA61K31/5025C07D487/04A61P1/04A61P31/04
Inventor 岩渕晴男萩原昌彦柴川信彦松言圭二藤原宽
Owner SANKYO CO LTD
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