S-(2-aminoethyl) ethanethioate;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The coupling reaction of 13 (3.93 mmol) with S-acetylcysteamine hydrochloride is carried out according to method B described in the first synthetic route (example 1). After the various treatments, the expected compound is isolated by flash chromatography on a silica gel column (eluent: AcOEt/petroleum ether 60%). 14 is collected in the form of a colorless foam with a yield of 67%. Rf (AcOEt/petroleum ether, 6/4): 0.5. [α]D20=+9.3° (c 0.97, CHCl3).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The coupling reaction of 13 (3.93 mmol) with S-acetylcysteamine hydrochloride is carried out according to method B described in the first synthetic route (example 1). After the various treatments, the expected compound is isolated by flash chromatography on a silica gel column (eluent: AcOEt/petroleum ether 60%). 14 is collected in the form of a colorless foam with a yield of 67%. Rf (AcOEt/petroleum ether, 6/4): 0.5. [α]D20=+9.3° (c 0.97, CHCl3).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The coupling reaction of 7 (7.41 mmol) is carried out according to Method B described in the first synthetic route (example 1): S-acetylcysteamine hydrochloride was replaced by S-benzoylcysteamine hydrochloride (T. Wieland and E. Bokelman, Ann. Chem., 1952, 576, 20-34. After the various treatments, the expected compound is isolated by flash chromatography on a silica gel column (eluent: CH2Cl2/ether 15%). 12 is collected in the form of a colorless foam with a yield of 62%. Rf (AcOEt/petroleum ether, 7/3): 0.42. [α]D20=+10.8° (c 1.11, CHCl3).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The coupling reaction of 7 (7.4 mmol) with S-pivaloylcysteamine hydrochloride [(compound obtained according to the same methods as those described by T. Wieland and E. Bokelman, Ann. Chem., 1952, 576, 20-34, during the syntheses of S-acetylcysteamine hydrochloride and S-benzoylcysteamine hydrochloride) M.p.=212-213° C.] is carried out according to method B described in the first synthetic route (example 1). After the various treatments, the expected compound is isolated by flash chromatography on a silica gel column (eluent: CH2Cl2/ether 30%). 11 is collected in the form of a colorless foam with a yield of 86%. Rf (AcOEt/petroleum ether, 7/3): 0.5. [α]D20=+8.5° (c 1.29, CHCl3). obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The coupling reaction of 7 (4.5 mmol) with S-isobutyrylcysteamine hydrochloride [(compound obtained according to the same methods as those described by T. Wieland and E. Bokelman, Ann. Chem., 1952, 576; 20-34; during the syntheses of S-acetylcysteamine hydrochloride and S-benzoylcysteamine hydrochloride) M.p.=147-148° C.] is carried out according to method B described in the first synthetic route (example 1). After the various treatments, the expected compound is isolated by flash chromatography on a silica gel column (eluent: CH2Cl2/ether 30%). 10 is collected in the form of a colorless foam with a yield of 80%. Rf (AcOEt/petroleum ether, 8/2): 0.37. [α]D20=+10° (c 1.1, CHCl3). obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The first process for the preparation of the compound I-152 (scheme 1) corresponds to the process for the preparation of the compound of general formula (I) described above and involves correctly protected L-cysteine. This preparation process is characterized in that it comprises the following stages (i) of coupling of N-acetyl-S-trityl-L-cysteine (7) with S-acetylcysteamine hydrochloride to provide the compound N-(N-acetyl-S-trityl-L-cysteinyl)-S-acetylcysteamine (8); then (ii) of S-detritylation reaction of the compound N-(N-acetyl-S-trityl-L-cysteinyl)-S-acetylcysteamine, in solution in methanol and chloroform, with a mixture of silver nitrate, pyridine and methanol to provide the corresponding silver sulfide (9); then (iii) of suspending said corresponding silver sulfide in chloroform; then (iv) of release of the free thiol in the presence of HCl or H2S.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The coupling reaction of 13 (3.93 mmol) with S-acetylcysteamine hydrochloride is carried out according to method B described in the first synthetic route (example 1). After the various treatments, the expected compound is isolated by flash chromatography on a silica gel column (eluent: AcOEt/petroleum ether 60%). 14 is collected in the form of a colorless foam with a yield of 67%. Rf (AcOEt/petroleum ether, 6/4): 0.5. [α]D20=+9.3° (c 0.97, CHCl3).