Preparation method of vascular leakage blockers with a high yield
AssigneeCuracle Co., Ltd.
InventorsKoo Hyeon Ahn, Myung-Hwa Kim, Jung-Ln Pyo, Chul Su Baek, Sung Hwan Kim
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Abstract
The present invention relates to a preparation method of a novel vascular leakage blocker with a high yield. The preparation method is easy to react and more productive and economical than the conventional method by using an intermediate that can easily remove impurities generated during the reaction. In addition, the preparation method can produce a novel vascular leakage blocker with a high yield by using a new reagent that has not been previously used in the step of generating an isomer, and is very advantageous in producing a high-quality active pharmaceutical ingredient.
Claims12
A preparation method of a novel vascular leakage blocker represented by formula 1 comprising the following steps, as shown in reaction formula 1 below:
- preparing a compound represented by formula 2 by reacting a compound represented by formula 4 with a compound represented by formula 5 (step 1);
- and
- preparing a compound represented by formula 1 by reacting the compound represented by formula 2 obtained in step 1 above with a compound represented by formula 3 in the presence of a catalyst comprising lithium nonafluoro-1-butyl sulfonate (Li—NFBS) and (s)-camphor sulfonic acid (step 2):
- In reaction formula 1,
- R1 is straight or branched C1-10 alkyl.
A preparation method of a novel vascular leakage blocker represented by formula 1 comprising the following steps, as shown in reaction formula 3 below:
- preparing a compound represented by formula 6 by reacting pregnenolone with a compound represented by formula 8 (step 1);
- preparing a compound represented by formula 4 by reacting the compound represented by formula 6 obtained in step 1 above with a compound represented by formula 7 and then treating it under acid condition (step 2);
- preparing a compound represented by formula 2 by reacting the compound represented by formula 4 obtained in step 2 above with a compound represented by formula 5 (step 3);
- and
- preparing a compound represented by formula 1 by reacting the compound represented by formula 2 obtained in step 3 above with a compound represented by formula 3 in the presence of a catalyst comprising lithium nonafluoro-1-butyl sulfonate (Li—NFBS) and (s)-camphor sulfonic acid (step 4):
- In reaction formula 3,
- R1 is straight or branched C1-10 alkyl.
A preparation method of a novel vascular leakage blocker represented by formula 1 comprising the following steps, as shown in reaction formula 4 below:
- preparing a compound represented by formula 10 by reacting a compound represented by formula 6, a compound represented by formula 7 and a compound represented by formula 9 (step 1);
- preparing a compound represented by formula 2 by reacting the compound represented by formula 10 obtained in step 1 above with an acid material (step 2);
- and
- preparing a compound represented by formula 1 by reacting the compound represented by formula 2 obtained in step 2 above with a compound represented by formula 3 in the presence of a catalyst comprising lithium nonafluoro-1-butyl sulfonate (Li—NFBS) and (s)-camphor sulfonic acid (step 3):
- In reaction formula 4,
- R1 is straight or branched C1-10 alkyl;
- and
- X1 is halogen.
Dependencies are inferred from the claim text.