6-alkenyl-, 6-alkinyl- and 6-epoxy-epothilone derivatives, process for their production, and their use in pharmaceutical preparations

An epothilone compound of formula I,

• in which
• R1a, R1b are the same or different and mean hydrogen;
• C1–C10 alkyl, C6–C12 aryl, or C7–C20 aralkyl, each, except hydrogen, is optionally substituted;
• R2a means hydrogen, C1–C10 alkyl, C6–C12 aryl or C7–C20 aralkyl, each, except hydrogen, is optionally substituted;
• —(CH2)ra—C≡C—(CH2)pa—R26a;
• or —(CH2)ra—CH═CH—(CH2)pa—R26a,
• R2b means —(CH2)rb—C≡C—(CH2)pb—R26b, or —(CH2)rb—CH═CH—(CH2)pb—R26b,
• ra, rb are the same or different and mean 0 to 4,
• pa, pb are the same or different and mean 0 to 3,
• R3a means hydrogen or a C1–C10 alkyl, C6–C12 aryl or C7–C20 aralkyl, each, except hydrogen, is optionally substituted,
• R3b means OH or OPG14 where PG14 is a protective group,
• R14 means hydrogen, OR14a or Hal, where R14a is hydrogen, SO2-alkyl, SO2-aryl or SO2-aralkyl,
• R4 means hydrogen, C1–C10 alkyl, C6–C12 aryl or C7–C20 aralkyl, each, except hydrogen, is optionally substituted Hal;
• OR25;
• or CN;
• R25 means hydrogen or a protective group PG5,
• R26, R26b are the same or different and mean hydrogen;
• C1–C10 alkyl, C6–C12 aryl or C7–C20 aralkyl, each, except hydrogen, is optionally substituted C1–C10 acyl, or, if pa or pb>0, additionally a group OR27,
• R27 means hydrogen or a protective group PG6,
• R5 means hydrogen, C1–C10 alkyl, C6–C12 aryl, C7–C20 aralkyl, each optionally substituted;
• or (CH2)s-T,
• whereby
• s stands for 1, 2, 3 or 4,
• T stands for OR22 or Hal,
• R22 stands for hydrogen or a protective group PG4,
• R6, R7 each mean a hydrogen atom, or taken together an additional bond or an oxygen atom,
• G means a benzothiazolyl, benzoxazolyl or quinolinyl radical which is optionally substituted by halogen, OH, O-alkyl, CO2H, CO2-alkyl, —NH2, —NO2, —N3, —CN, C1–C20 alkyl, C1–C20 acyl, or C1–C20 acyloxy groups,
• D-E means a group —CH2—CH2—,
• A-Y means a group O—C(═O), or NR29—C(═O),
• R29 means hydrogen or C1–C10 alkyl,
• Z means an oxygen atom,
• Hal means halogen,
• wherein, in each occurrence “PG” together means a hydroxy protecting group.