Maytansinoids and use
First Claim
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1. A compound of the formula:
- ##STR4## wherein R is C3-10 cycloalkyl, C3-10 cycloalkenyl, phenyl or a heterocyclic group selected from the class consisting of pyridyl, pyrrolidinyl, tetrazolyl, furyl and thienyl, said cycloalkyl, cycloalkenyl, phenyl and heterocyclic group being unsubstituted or substituted by C1-4 alkyl, C1-4 alkoxy, C2-4 alkanoyl, C2-4 alkanoyloxy, C2-4 alkoxycarbonyl, halogen, nitro, cyano, trifluoromethyl, di-C1-4 alkylamino, C1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C1-4 alkanoylamido, andA is C1-4 alkylene or a bond, provided that A means said alkylene when attached to a N atom in said heterocyclic group R.
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Abstract
Novel maytansinoids of the formula: ##STR1## wherein R is an alicyclic hydrocarbon group of 3 to 10 carbon atoms, phenyl or heterocyclic group, which may optionally be substituted, and
A is an alkylene group of 1 to 4 carbon atoms or a bond, provided that A means said alkylene group when attached to a N atom in said heterocyclic group R,
have antimicrobial, antimitotic and antitumor activities.
171 Citations
13 Claims
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1. A compound of the formula:
- ##STR4## wherein R is C3-10 cycloalkyl, C3-10 cycloalkenyl, phenyl or a heterocyclic group selected from the class consisting of pyridyl, pyrrolidinyl, tetrazolyl, furyl and thienyl, said cycloalkyl, cycloalkenyl, phenyl and heterocyclic group being unsubstituted or substituted by C1-4 alkyl, C1-4 alkoxy, C2-4 alkanoyl, C2-4 alkanoyloxy, C2-4 alkoxycarbonyl, halogen, nitro, cyano, trifluoromethyl, di-C1-4 alkylamino, C1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C1-4 alkanoylamido, and
A is C1-4 alkylene or a bond, provided that A means said alkylene when attached to a N atom in said heterocyclic group R. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
- ##STR4## wherein R is C3-10 cycloalkyl, C3-10 cycloalkenyl, phenyl or a heterocyclic group selected from the class consisting of pyridyl, pyrrolidinyl, tetrazolyl, furyl and thienyl, said cycloalkyl, cycloalkenyl, phenyl and heterocyclic group being unsubstituted or substituted by C1-4 alkyl, C1-4 alkoxy, C2-4 alkanoyl, C2-4 alkanoyloxy, C2-4 alkoxycarbonyl, halogen, nitro, cyano, trifluoromethyl, di-C1-4 alkylamino, C1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C1-4 alkanoylamido, and
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12. A pharmaceutical composition suitable for inhibiting the growth of tumour cells and prolonging the survival time of a warm-blooded animal which comprises as an active ingredient an effective amount of a compound of the following formula (I) and a pharmaceutically acceptable carrier or diluent therefor:
- ##STR5## wherein R is C3-10 cycloalkyl, C3-10 cycloalkenyl, phenyl or a heterocyclic group selected from the class consisting of pyridinyl, pyrrolidinyl, tetrazolyl, furyl and thienyl, said cycloalkyl, cycloalkenyl, phenyl and heterocyclic group being unsubstituted or substituted by C1-4 alkyl, C1-4 alkoxy, C2-4 alkanoyl, C2-4 alkanoyloxy, C2-4 alkoxycarbonyl, halogen, nitro, cyano, trifluoromethyl, di-C1-4 alkylamino, C1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C1-4 alkanoylamido, and
A is C1-4 alkylene or a bond, provided that A means said alkylene when attached to a N atom in said heterocyclic group R.
- ##STR5## wherein R is C3-10 cycloalkyl, C3-10 cycloalkenyl, phenyl or a heterocyclic group selected from the class consisting of pyridinyl, pyrrolidinyl, tetrazolyl, furyl and thienyl, said cycloalkyl, cycloalkenyl, phenyl and heterocyclic group being unsubstituted or substituted by C1-4 alkyl, C1-4 alkoxy, C2-4 alkanoyl, C2-4 alkanoyloxy, C2-4 alkoxycarbonyl, halogen, nitro, cyano, trifluoromethyl, di-C1-4 alkylamino, C1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C1-4 alkanoylamido, and
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13. A method for inhibiting the growth of tumour cells and prolonging the survival time of a tumour-bearing warm-blooded animal, which comprises administering to said animal an effective amount of a compound of the formula:
- ##STR6## wherein R is C3-10 cycloalkyl, C3-10 cycloalkenyl, phenyl or heterocyclic group selected from the class consisting of pyridyl, pyrrodinyl, tetrazolyl, furyl and thienyl, said cycloalkyl, cycloalkenyl, phenyl and heterocyclic group being unsubstituted or substituted by C1-4 alkyl, C1-4 alkoxy, C2-4 alkanoyl, C2-4 alkanoyloxy, C2-4 alkoxycarbonyl, halogen, nitro, cyano trifluoromethyl, di-C1-4 alkylamino, C1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C1-4 alkanoylamido, and
A is C1-4 alkylene or a bond, provided that A means said alkylene when attached to a N atom in said heterocyclic group R.
- ##STR6## wherein R is C3-10 cycloalkyl, C3-10 cycloalkenyl, phenyl or heterocyclic group selected from the class consisting of pyridyl, pyrrodinyl, tetrazolyl, furyl and thienyl, said cycloalkyl, cycloalkenyl, phenyl and heterocyclic group being unsubstituted or substituted by C1-4 alkyl, C1-4 alkoxy, C2-4 alkanoyl, C2-4 alkanoyloxy, C2-4 alkoxycarbonyl, halogen, nitro, cyano trifluoromethyl, di-C1-4 alkylamino, C1-4 alkylthio, methylsulfinyl, methylsulfonyl, oxo, thioxo or C1-4 alkanoylamido, and
Specification
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Current AssigneeTakeda Chemical Industries, Ltd. (Takeda Pharmaceutical Company Limited)
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Original AssigneeTakeda Chemical Industries, Ltd. (Takeda Pharmaceutical Company Limited)
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InventorsAkimoto, Hiroshi, Miyashita, Osamu
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Primary Examiner(s)Jiles, Henry R.
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Assistant Examiner(s)Bond, Robert T.
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Application NumberUS06/085,880Time in Patent Office474 DaysField of Search260/239.3 P, 424/248.54US Class Current514/229.5CPC Class CodesA61P 35/00 Antineoplastic agentsC07D 498/18 Bridged systems
