Acic (canada) Inc.

Brantford Chemicals Inc.

Brantford Chemicalss Inc.

Khashayar Karimian

Bruno K Radatus

Keshava Ks Murthy

Darren Hall

Anand Daljeet

Novel methods for the synthesis of substituted ureas and guanidines including Terazosin, Prazosin, Doxazosin, Tiodazosin, Trimazosin, Quinasin and Bunazosin (exemplary of 2-amino substituted Quinazolines), Meobentine and Bethanidine and novel intermediates suitable for use in such methods of synthesis are taught.

Methods of making ureas and guanidines including, terazosin, prazosin,

Methods of making ureas and guanidines, including terazosin, prazosin,

Methods of making ureas and guanidines, including, terazosin, prazosin,

A novel process is provided for producing a nucleoside, such as cytarabine, or a nucleoside analogue, comprising the step of reacting 2,2'-O-cyclonucleoside or an analogue thereof with an amine. Preferably, the process is conducted in the presence of an aqueous solvent. A novel process for the production of the precursor 2,2'-O-cyclonucleoside compounds and pharmaceutically acceptable salts thereof is also provided which comprises reacting a 2,3'-O-diaikylstannylene nucleoside compound with an amine in the presence of a sulfonyl compound. Cytarabine is a known antineoplastic and antiviral agent.

Process for producing 2,2'-o-cyclonucleosides nucleosides, and analogs

A process from preparing 5-halogenated 2,3-O-cyclocytidine derivatives comprising reacting 2,3-O-cyclocytidine with a halogenating reagent, preferably N-bromosuccinimide, in the presence of an acid such as acetic or trifluoroacetic.

Process for preparing halogenated 2,3-O-cyclocytidine derivatives

Compounds of Formula IV: ##STR1## are described. In the compounds of Formula IV, R.sup.6 is selected from a trifluoromethyl group, a C.sub.1 -C.sub.6 alkyl group and a C.sub.6 -C.sub.9 aryl group, and R.sup.1 is selected from hydrogen, trityl, methoxytrityl, dimethoxytrityl, acetyl, a C2-C6 alkylacyl group, a C6-C9 arylacyl group, allyl, 2,2,2-trichloroethyl, phosphates and salts thereof, tosyl and mesyl. The above organosulfonyl salts of 2,3'-O-cyclocytidine are intermediates in the preparation of 1-(B-D-xylopentofuranose)cytosine, an inhibitor of DNA synthesis.

Organosulfonyl salts of 2,3'-O-cyclocytidine

A 5'-halo-2,3'-O-cyclocytidine of Formula I: ##STR1## wherein: X is a bromide, chloride, or iodide; Y is halide, sulfate, acetate, tosyl, mesyl, benzoate, and phosphate; R.sup.1 is hydrogen; and R.sup.2 is a hydroxy protecting group. Pharmaceutical compositions containing the above compounds exhibit antineoplastic activity.

5-halo-2,3'-O-cyclocytidines

A composition of a 1:1 molar complex of guanidine and 3'-azido-3'-deoxythymidine (AZT) which is generated at about pH above 9 and disrupted by pH below about 9. This complex is a useful intermediate in the purification of AZT.

Complex of guanidine and AZT

Process for preparing 2,3'-O-cyclocytidine

A process for recovering 3'-azido-3'-deoxythymidine (AZT) or a salt thereof from a mixture of chemicals involving the reaction of the AZT with guanidine to form a salt precipitate. The salt precipitate is then acidified to pH of less than about 9 to yield free AZT, which can then be crystallized from solution. 3'-Azido-3'-deoxythymidine and its salts, also known as AZT and Zidovudine, is used in the treatment of AIDS patients.

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Brantford, Canada

Khashayar Karimian