- Practical one-pot synthesis of N-(tert-butoxycarbonyl)sulfamide from chlorosulfonyl isocyanate via N-(terf-butoxycarbonyl)aminosulfonylpyridinium salt
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An efficient and practical process for the one-pot synthesis of N-(tert-butoxycarbonyl)sulfamide (4), a raw material for the aminosulfamoyl-containing side chain 3 of a novel carbapenem antibiotic doripenem hydrate (S-4661: 1), is described. In the previous process, chlorosulfonyl isocyanate was converted to N-(terf-butoxycarbonyl)aminosulfonyl chloride (7), an extremely unstable intermediate against moisture, which afforded the target compound 4 using liquid ammonia at cryogenic temperatures in 90% isolated yield. The use of liquid ammonia required cryogenic reaction temperatures because of heat generated from the highly exothermic reaction and the low boiling point of ammonia. In the improved process, the deactivation of the sulfonyl chloride 7 with pyridine at 0°C afforded water-resistant N-(tert-butoxycarbonyl)aminosulfonylpyridinium salt (8) which was converted in situ to the target compound 4 in the presence of water at 0°C in 90-96% isolated yields. Aqueous ammonia can be used, and no cryogenic temperatures are necessary for this new one-pot process.
- Masui, Toshiaki,Kabaki, Mikio,Watanabe, Hideaki,Kobayashi, Tatsuya,Masui, Yoshiyuki
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Read Online
- PROCESS FOR THE PREPARATION OF SULFAMIDE DERIVATIVES
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The present invention is directed to a process for the preparation of sulfamide derivatives.
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Page/Page column 44; 45
(2013/04/13)
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- INHIBITORS OF E1 ACTIVATING ENZYMES
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This invention relates to compounds that inhibit El activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.
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Page/Page column 86-87
(2008/06/13)
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- 1-ACYLAMINO-2-HYDROXY-3-AMINO-W-ARYLALKANES AS RENIN INHIBITORS
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1-Acylamino-2-hydroxy-3-amino-ω-arylalkanes of formula I. and the salts thereof, have renin-inhibiting properties and can be used as antihypertensive, medicinally active ingredients.
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Page/Page column 106
(2008/06/13)
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- One-pot synthesis of N-acyl-substituted sulfamides from chlorosulfonyl isocyanate via the Burgess-type intermediates
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The title N-alkoxycarbonyl- or N-aryloxycarbonyl-substituted sulfamides were synthesised in one-pot in efficient yields from chlorosulfonyl isocyanate (CSI), alcohols and aqueous (or dry) amines via the corresponding water-resistant intermediates, carboxy
- Masui, Yoshiyuki,Watanabe, Hideaki,Masui, Toshiaki
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p. 1853 - 1856
(2007/10/03)
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- Practical large-scale synthesis of the 2-aminomethylpyrrolidin-4-ylthio-containing side chain of the novel carbapenem antibiotic doripenem
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The first synthesis using an original procedure and a practical large-scale process using an improved procedure for the synthesis of the N-PNZ-protected 2-aminomethylpyrrolidin-4-ylthio-containing side chain of doripenem hydrate (S-4661), a novel parenteral 1β-methylcarbapenem antibiotic, are described, trans-4-Hydroxy-L-proline (4) was converted in an efficient process to (2S,4S)-4-acetylthio-2-(N-sulfamoyl-tert-butoxycarbonylaminomethyl) -1-(4-nitrobenzyloxycarbonyl)pyrrolidine (3) in 55-56% overall yield via a six-step sequence, which includes the two alternative routes to intermediate 13. This process requires no chromatographic purifications, no cryogenic temperatures, no haloalkane solvents, and short operating times and is amenable to a multikilogram-scale preparation. Several kilograms of the side chain 3 were successfully prepared by this process.
- Nishino, Yutaka,Komurasaki, Tadafumi,Yuasa, Tetsuya,Kakinuma, Makoto,Izumi, Kenji,Kobayashi, Makoto,Fujiie, Shinichiro,Gotoh, Teruhiro,Masui, Yoshiyuki,Hajima, Makoto,Takahira, Masayuki,Okuyama, Akira,Kataoka, Takahiro
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p. 649 - 654
(2013/09/05)
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- N-hydroxysulfamides as analog of N-hydroxyurea: synthesis and biological evaluation
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A series of sulfa-analog of hydroxyurea, derived from N-hydroxysulfamide H2NSO2NHOH, were synthesized starting from chlorosulfonyl isocyanate (CSI) and O-substituted hydroxylamines. Their antiproliferative, antiviral (in synergy with
- Hajri, A.-Houssem,Dewynter, Georges,Criton, Marc,Dilda, Pierre,Montero, Jean-Louis
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- THF-CONTAINING SULFONAMIDE INHIBITORS OF ASPARTYL PROTEASE
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The present invention relates to a class of THF-containing sulfonamides which are aspartyl protease inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention.
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- Synthesis and modification of a novel 1 β-methyl carbapenem antibiotic, S-4661
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We describe an efficient method for introducing a sulfamoylamino group into the C-2' position of pyrrolidine using the Mitsunobu reaction. S-4661, its N-methyl analogues and stereoisomers were synthesized using this method and their structure-activity relationships were investigated.
- Iso,Irie,Iwaki,Kii,Sendo,Motokawa,Nishitani
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p. 478 - 484
(2007/10/03)
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- Pyrrolidylthiocarbapenem derivative
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A pyrrolidylthiocarbapenem derivative represented by Formula I is provided: STR1 wherein R1 is hydrogen or lower alkyl; R2, R3 and R4 are hydrogen, lower alkyl which can be substituted or an amino protecting group independently, or R2 and R3 together with a nitrogen atom to which R2 and R3 are bonded form a saturated or unsaturated cyclic group, or R2 and R4, or R3 and R4 together with two nitrogen atoms and one sulfur atom in the sufamide group form a saturated or unsaturated cyclic group; each cyclic group can further include at least one atom selected from the group consisting of oxygen, sulfur and nitrogen, and each cyclic group can be substituted; X1 is hydrogen or a hydroxy protecting group; X2 is hydrogen, a carboxy protecting group, an ammonio group, an alkali metal or an alkaline-earth metal; and Y2 is hydrogen or an amino protecting group.
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