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Amino methanol derivant and salt compound thereof as well as synthesizing method and medical application thereof

A technology of salt compounds and aminomethanol, which is applied in the preparation of aminohydroxyl compounds, active ingredients of heterocyclic compounds, organic chemical methods, etc., can solve the problems of non-research and development

Inactive Publication Date: 2010-07-07
FORELAND PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, FTY720 acts not only on 1-phosphate-sphingosine receptor-1 (S1P1) but also on 1-phosphate-sphingosine receptor-3 (S1P3), and thus can cause side effects such as bradycardia (6)
There is no report on the research and development of this similar drug in China

Method used

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  • Amino methanol derivant and salt compound thereof as well as synthesizing method and medical application thereof
  • Amino methanol derivant and salt compound thereof as well as synthesizing method and medical application thereof
  • Amino methanol derivant and salt compound thereof as well as synthesizing method and medical application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment approach

[0106] One embodiment of the present invention, such as the compound of formula II:

[0107]

[0108] in:

[0109] R1 = methyl, chlorine, bromine, fluorine;

[0110] R2 = H, C 4 -C 6 -C 8 Alkyl, Heptyloxy, Phenoxy, 4-Methoxyphenoxy, 4-(Benzyloxy)phenoxy, Phenyl, 6-Methoxyhexyl, 4-(Benzyloxy) Phenylthio, 3-methoxyphenoxy, 3-(benzyloxy)phenoxy, 3-(benzyloxy)phenylthio, halogen, 6-methoxyhexyl, phenoxy, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 3-methoxyphenoxy, 3-(benzyloxy)phenoxy, phenyl, 3-(benzyl Oxy)phenylthio, 6-methoxyhexyl;

[0111] R3=H, C 4 -C 6 -C 8 Alkyl, Heptyloxy, Phenoxy, 4-Methoxyphenoxy, 4-(Benzyloxy)phenoxy, Phenyl, 6-Methoxyhexyl, 4-(Benzyloxy) Phenylthio, 3-methoxyphenoxy, 3-(benzyloxy)phenoxy, 3-(benzyloxy)phenylthio, halogen, 6-methoxyhexyl, phenoxy, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 3-methoxyphenoxy, 3-(benzyloxy)phenoxy, phenyl, 3-(benzyl Oxy)phenylthio, 6-methoxyhexyl;

[0112] R4 = methyl, chlorine, bromine, flu...

Embodiment 1

[0124] The synthetic method of 2-amino-1,2,3,4-tetrahydro-2-naphthalenemethanol (FC-001) and its hydrochloride (FC-002) (hereinafter referred to as FC-001, FC-002) is as follows Show:

[0125]

[0126] Synthesis of 3',4'-dihydro-spiro[imidazoline-4,2'(1'H)-naphthalene]-2,5-dione

[0127] Take 8g (54.8mmol) of 2-tetralone, 4g (61.5mmol) of potassium cyanide, 48g (500mmol) of ammonium carbonate, and 320mL of 50% ethanol solution, heat and reflux for 2h, evaporate the ethanol, filter, and wash the filter cake with water until Neutral, dried to give 8.6 g of white solid 3',4'-dihydro-spiro[imidazoline-4,2'(1'H)-naphthalene]-2,5-dione, yield 73%; mp 150 -152°C; 1 H NMR (400MHz, DMSO) δ: 10.69(s, 1H, -NH-), 8.29(s, 1H, -NH-), 7.08-7.13(m, 4H, 4×-ArH), 3.12(d, 1H , J=17.2Hz, -CH-), 2.88-2.97 (m, 2H, -CH 2-), 2.76(d, 1H, J=16.8Hz), 1.94-1.98(m, 1H, -CH-), 1.82-1.84(m, 1H, -CH-); 13 C NMR (100 MHz, DMSO) δ: 178.1, 156.3, 134.8, 132.6, 128.9, 128.5, 125.9, 125.8, 60.7, 36.8, 30....

Embodiment 2

[0136] 2-amino-7-n-butyl-1,2,3,4-tetrahydro-2-naphthalenemethanol (FC-003) and its hydrochloride (FC-004) (hereinafter referred to as FC-003, FC-004 ) is synthesized as follows:

[0137]

[0138] Synthesis of 7-bromo-2-tetralone

[0139] Take 20g (94mmol) of m-bromophenylacetic acid, 240mL of 1,2-dichloroethane, 21mL (296mmol) of thionyl chloride, heat to reflux for 4h, spin the solvent, add 100mL of dichloromethane, and add the above acid chloride solution to Into a mixed solution of 28g (209mmol) of anhydrous aluminum chloride and 300mL of dichloromethane, feed ethylene at a temperature lower than 0°C for reaction, after the reaction (about 4h), add 200mL of water, extract with dichloromethane, The organic phase was washed successively with 1N HCl and saturated sodium carbonate solution, dried over anhydrous magnesium sulfate, and evaporated to remove the solvent. Silica gel column chromatography (developing solvent: ethyl acetate:petroleum ether=1:5) gave white solid 7-...

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Abstract

The invention relates to an amino methanol derivant and a salt compound thereof as well as a synthesizing method and medical application thereof, belonging to the field of medicines. The medical application is applied in preparing immunosuppressive drugs and drugs for treating transplant rejection, immune and inflammatory diseases, multiple sclerosis, systemic lupus erythematosus and rheumatoid arthritis. The amino methanol derivant and a physiological salt thereof only act on S1P1, downwards regulate the S1P1 expression and suppress lymphocytes from entering peripheral blood circulation.

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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IPC IPC(8): C07C215/42C07C213/00C07C217/52C07C323/38A61K31/135A61P37/06
CPCC07C2102/10C07B2200/07C07C215/42C07C323/38A61K31/33C07C217/52A61P37/06C07C2602/10
Inventor 王恩思梁铁路海滨米浩宇
Owner FORELAND PHARM CO LTD
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