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Benzoxazine-pyrazoles and opened loop compound

By developing benzoxazinopyrazole compounds and their ring-opening compounds, the problem of existing antithrombotic drugs being difficult to protect brain cells in stroke treatment has been solved. The compounds show strong antioxidant capacity and neuroprotective effects, and have excellent Brain protective effects of edaravone.

Inactive Publication Date: 2008-12-10
QINGDAO HUANGHAI PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] After stroke, recanalization of occluded blood vessels may restore brain function in a short period of time, but continuous ischemia over a certain period of time will cause irreversible damage to brain cells

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 Preparation of 2-methyl-benzo[d][1,3]oxazin[5-b]pyrazol-5-one (compound 1)

[0068] Preparation of ethyl 2-hydrazinobenzoate hydrochloride

[0069]

[0070] Add 600ml of concentrated hydrochloric acid, 500ml of crushed ice, and 82.5g (0.5mol) of ethyl 2-aminobenzoate into a 2000ml three-necked flask, and stir until completely dissolved. Ice-salt bath to -7~-3°C, dropwise add 34.5g (0.5mol) of sodium nitrite solution dissolved in 150ml of water, after the dropwise addition, stir for 10min to obtain an orange-yellow clear solution, which is ready for use.

[0071] Add 350g of stannous chloride and 1000ml of concentrated hydrochloric acid into a 5000ml three-neck flask, stir until completely dissolved, cool in an ice-salt bath to -5°C, add the above-mentioned diazonium salt solution dropwise, a white precipitate occurs, after the dropwise addition is complete, continue stirring for 2 hours , filtered, and the filter cake was washed with a large amount of satu...

Embodiment 2

[0079] Example 2 Preparation of 2-methyl-5-imino-benzo[d][1,3]oxazine[5-b]pyrazole (compound 2)

[0080] Preparation of 2-hydrazinobenzonitrile hydrochloride

[0081]

[0082] Add 600ml of concentrated hydrochloric acid, 500ml of crushed ice, and 59g (0.5mol) of 2-aminobenzonitrile into a 2000ml three-necked flask, and stir until completely dissolved. Ice-salt bath to -7~-3°C, dropwise add 34.5g (0.5mol) of sodium nitrite solution dissolved in 150ml of water, after the dropwise addition, stir for 10min to obtain an orange-yellow clear solution, which is ready for use.

[0083] Add 350g of stannous chloride and 1000ml of concentrated hydrochloric acid into a 5000ml three-neck flask, stir until completely dissolved, cool in an ice-salt bath to -5°C, add the above-mentioned diazonium salt solution dropwise, a white precipitate occurs, after the dropwise addition is complete, continue stirring for 2 hours , filtered, and the filter cake was washed with a large amount of satura...

Embodiment 3

[0090] Example 3 Preparation of 1-(2-carboxyphenyl)-3-methylpyrazol-5-one (compound 3)

[0091]

[0092] In a 250ml reaction flask, add 10g (0.053mol) of 2-hydrazinobenzoic acid hydrochloride (for the preparation method refer to Organic Syntheses, Coll.Vol.3, p475, 1955), 7g (0.054mol) of ethyl acetoacetate, 100ml of methanol, and stir Add 7g (0.065mol) of 50% sodium methoxide dissolved in 50ml of methanol, stir for 10min, heat to reflux for 6h, filter while hot, wash the solid with 20ml of methanol, recover the methanol to dryness, and recrystallize with 10% hydrochloric acid to obtain hydrochloric acid 6.5 g of 1-(2-carboxyphenyl)-3-methylpyrazol-5-one, yield 48%.

[0093] 1H-NMR (δ): 8.23ppm, 1H, d; 7.75ppm, 1H, t; 7.45ppm, 1H, d; 7.32ppm, d; 2.56ppm, 2H, s;

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Abstract

The invention discloses a benzoxazine pyrazole compounds with a formula I and a formula II and a ring opening compound with a formula III and a preparation method thereof. The invention also discloses an application of the compounds with the formula I and the formula II and the compound with the formula III or salt acceptable in pharmacy in preparing drugs for treating or preventing cardiovascular and cerebrovascular diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a benzoxazinopyrazole compound or a ring-opened compound thereof, a preparation method thereof, and an application in preparation of drugs for treating or preventing cardiovascular and cerebrovascular diseases. Background technique [0002] Thrombosis is the pathological basis of cardiovascular and cerebrovascular diseases with high disability and fatality rates such as stroke. And so on. Antithrombotic drugs include anticoagulant drugs, antiplatelet drugs, and drugs that target endothelial cells. Currently, antiplatelet drugs commonly used in clinical practice include aspirin, ticlopidine, and clopidogrel; platelet GP II b / 11Ia receptor antagonists include monoclonal antibody abciximab (abciximab), and synthetic peptide receptor antagonists such as Eptifibatide (eptifibatide); non-peptide receptor antagonists such as cyclic heptapeptide tirofiban (tirofiban) and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04C07D231/22A61K31/5383A61K31/4152A61P9/00A61P7/02
CPCA61K31/4152A61K31/5383C07D231/22C07D498/04A61P25/00A61P7/00A61P7/02A61P9/00A61P9/10
Owner QINGDAO HUANGHAI PHARM CO LTD
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