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Heterocyclic group contained amino-methanol derivative, its salt, its synthetic method and its use

A kind of aminomethanol, heterocyclic group technology, applied in the field of medicine

Inactive Publication Date: 2012-12-12
FORELAND PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, FTY720 not only acts on 1-phosphate-sphingosine receptor-1 (S1P1), but also acts on 1-phosphate-sphingosine receptor-3 (S1P3), thus can cause side effects such as bradycardia (6)

Method used

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  • Heterocyclic group contained amino-methanol derivative, its salt, its synthetic method and its use
  • Heterocyclic group contained amino-methanol derivative, its salt, its synthetic method and its use
  • Heterocyclic group contained amino-methanol derivative, its salt, its synthetic method and its use

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0157] Preparation of Intermediate 1:

[0158]

[0159] The raw material m-bromophenylacetic acid (100 g, 0.47 mol, 1.0 eq) was dissolved in dichloromethane (500 ml), cooled to 0°C in an ice-salt bath, and oxalyl chloride (120 g, 0.95 mol, 2.0 eq ), the dropping temperature was kept at 0°C. After the dropwise addition was completed, the reaction was changed to room temperature for 2 hours. After the reaction was completed, the mixture was concentrated under reduced pressure to obtain m-bromo-phenylacetyl chloride (110 g, 0.47 mol), which was dissolved in dichloromethane (200 ml) for further use.

[0160] In another reaction flask, aluminum trichloride (210 g, 1.9 mol, 4.0 eq ) and dichloromethane (500 mL) were added. Cool the system to -5°C in an ice-salt bath, add the dichloromethane solution of the acid chloride prepared above to the system dropwise, and keep the temperature at -5°C. , continue to pass ethylene gas for 3 hours. After the reaction was completed, it was...

example 1

[0186] Synthesis of Example 1:

[0187]

[0188] Reaction Scheme 6: Synthesis of Example 1

[0189] Preparation of Intermediate 19:

[0190]

[0191] A mixture of methyl 4-methoxybenzoate (33 g, 0.2 mol) and anhydrous hydrazine (7.7 g, 0.24 mmol) was heated to 140 °C under nitrogen, and the reaction was continued at this temperature for 30 min. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate (3 x 100ml). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the crude product of compound intermediate 19 (30 g), which was directly used in the next reaction.

[0192] Preparation of Intermediate 20:

[0193]

[0194] raw material 18 (0.5 g, 1.0 eq) was dissolved in dry dichloromethane (20 ml), DMF (0.01 g, cat) was added, the temperature was lowered to 0 °C, oxalyl chloride (500 mg, 3.0 eq) was added dropwise, and the React at room temperature for 30 min. After t...

example 2

[0203] Example 2: 6-[5-(4-ethoxyphenyl)-2-[1,3,4]oxadiazolyl]-]-2-amino-1,2,3,4-tetrahydro- 2-Naphthyl-methanol

[0204] NMR (400MHz, CD 3 OD) δ= 8.04 (2H, d), 7.92 (2H, m), 7.41 (1H, m), 7.52 (2H, d), 4.10 (2H, m), 3.60 (2H, d), 3.30 (4H, m), 3.00 (2H, m), 1.40 (3H, t); Rt = 3.34 min, MS (M + H + ): 366, theoretically calculated value: 366

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Abstract

The invention relates to a heterocyclic group contained amino-methanol derivative, its salt, its synthetic method and its use, and belongs to the medical field. The heterocyclic group contained aminomethanol derivative and its salt are used for preparing medicines for immune suppression and organ transplant repulsion reaction treatment, or medicines for treating immune inflammation diseases, such as Multiple Sclerosis, systemic lupus erythematosus and rheumatoid arthritis.

Description

technical field [0001] The invention belongs to the field of medicine and can be used for treating various transplant rejection reactions and immune inflammatory diseases such as multiple sclerosis, systemic lupus erythematosus, rheumatoid arthritis and the like. Background technique [0002] The immune system is a defensive structure for the body to protect itself. It is mainly composed of lymphoid organs (thymus, lymph nodes, spleen, tonsils), lymphoid tissues in other organs, lymphocytes and antigen-presenting cells throughout the body, as well as other organs in the blood. Plasma cells and mast cells in white blood cells and connective tissue. The core component of the immune system is lymphocytes, which enable the immune system to have the ability to recognize and remember. Lymphocytes travel around the body through the blood and lymph, from one lymphoid organ or lymphoid tissue to another lymphoid organ or lymphoid tissue, connecting the scattered lymphoid organs and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/107C07D271/06C07D249/06A61K31/4192A61K31/4245A61P37/06A61P37/02A61P29/00A61P19/02
CPCC07D249/06C07D271/06C07D271/107C07D413/04A61P19/02A61P29/00A61P37/02A61P37/06
Inventor 张兴民王恩思郭靖牛生秀戴琢琳郑楠季丽萍王震芳梁铁
Owner FORELAND PHARM CO LTD
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