Patent ES-8602795-A1 (ES)
Title: Pentacyclic compounds.
IPC: C07D223/32
Filed: 1983-10-06
Abstract: EP--88575 A Octahydro-10b,13 diazabenzo(gh)pleiadene derivs. and analogues of formula (I) and their N-oxides and salts are new. (R1 is H, 1-7C alkyl, 3-7C cycloalkyl, 4-7C cycloalkenyl or 1-4C alkyl substd. by 2-7C alkenyl, 2-7C alkynyl, 3-7C cycloalkyl, OH, SH, 1-4C alkoxy, 1-4C alkylthio, COOH, (1-4C) alkoxycarbonyl, 1-4C alkanoyl, NH2 opt. substd. by 1 or 2 alkyls having 1-4C or by 4-6C polymethylene opt. contg. a O or N atom, aminocarbonyl opt. N-substd. by 1 or 2 alkyls having 1-4C, or PhCO or Ph both opt. ring substd. by 1-4C alkyl, 1-4C alkoxy, halogen or CF3 R2 and R3 are H, OH, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio, halogen or CF3 m is 1-3 n is 1 or 2 and the H atom bonded to C(a) is trans to the H atom bonded to C(b)). - Intermediates are also claimed. Specifically claimed are 17 cpds. (I), including trans-13-methyl-1,2,6,11,12,13,13a,13b octahydro-10b,13 diazabenzo(gh)pleiadene (Ia). - Cpds. (I) are CNS active agents esp. mood modifiers for antidepressant use. Dose is 0.01-10 mg/kg daily. (0/0) EPAB- EP--88575 B Octahydro-10b,13 diazabenzo(gh)pleiadene derivs. and analogues of formula (I) and their N-oxides and salts are new. (R1 is H, 1-7C alkyl, 3-7C cycloalkyl, 4-7C cycloalkenyl or 1-4C alkyl substd. by 2-7C alkenyl, 2-7C alkynyl, 3-7C cycloalkyl, OH, SH, 1-4C alkoxy, 1-4C alkylthio, COOH, (1-4C) alkoxycarbonyl, 1-4C alkanoyl, NH2 opt. substd. by 1 or 2 alkyls having 1-4C or by 4-6C polymethylene opt. contg. a O or N atom, aminocarbonyl opt. N-substd. by 1 or 2 alkyls having 1-4C, or PhCO or Ph both opt. ring substd. by 1-4C alkyl, 1-4C alkoxy, halogen or CF3 R2 and R3 are H, OH, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio, halogen or CF3 m is 1-3 n is 1 or 2 and the H atom bonded to C(a) is trans to the H atom bonded to C(b)). - Intermediates are also claimed. Specifically claimed are 17 cpds. (I), including trans-13-methyl-1,2,6,11,12,13,13a,13b octahydro-10b,13 diazabenzo(gh)pleiadene (Ia). - Cpds. (I) are CNS active agents esp. mood modifiers for antidepressant use. Dose is 0.01-10 mg/kg daily. (94pp Dwg.No. 0/0) - EP--88575 B A compound of formula (I), or an N-oxide or pharmaceutically acceptable salt thereof, wherein R1 is hydrogen, C1-7 alkyl, C3-7 cycloalkyl, C4-7 cycloalkenyl or C1-4 alkyl substituted by 2-7 alkenyl, C2-7 alkynyl, C3-7 cycloalkyl, hydroxy, thiol, C1-4 alkoxy, C1-4 alkylthio, carboxy, C1-4 alkoxycarbonyl, C1-4 alkanoyl, amino optionally substituted by one or two C1-4 alkyl or by C4-6 polymethylene optionally containing an oxygen or nitrogen atom, aminocarbonyl optionally N-substituted by one or two C1-4 alkyl, or benzoyl or phenyl either being optionally ring substituted by C1-4 alkyl, C1-4 alkoxy, halogen or trifluoromethyl, R2 and R3 are the same or different and are hydrogen, hydroxy, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, halogen or trifluoromethyl, m is 2 and n is 1 or 2, the hydrogen atom bonded to the Ca carbon atom being trans to the hydrogen atom bonded to the Cb carbon atom. (38pp) USAB- US4504480 A Cpd. of formula (I), or N-oxide or pharmaceutically acceptable salt is new. (R1 is H, 1-4C alkyl, 3-7C cycloalkyl, 4-7C cycloalkenyl or 1-4C alkyl substd. by 2-7C alkenyl, 2-7c alkylnyl, 3-7C cycloalkyl, hydroxy, thiol, 1-4C alkoxy, 1-4C alkylthio, carboxy, 1-4C alkoxycarbonyl, 1-4C alkanoyl, amino opt. substd. by one or two 1-4C alkyls or by 4-6C polymethylene opt. having an oxygen or nitrogen atom, aminocarbonyl opt. N-substd. by one or two 1-4C alkyls, or benzoyl or phenyl either being opt. ring-substd. by 1-4C alkyl, 1-4C alkoxy, halogen or trifluoromethyl R2 and R3 are opt. the same and are H, hydroxy, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio, halogen or trifluoromethyl m is 2, and n is 1 or 2, the H atom bonded to the Ca carbon atom being trans to the hydrogen atom bonded to the Cb carbon atom.a - US4585588 A Cpds. of formula (I) are claimed. where R2 and R3 are each H, OH, alkyl, alkoxy, alkylthio, halogen or CF3 n is 1 or 2 H atoms bonded to Ca and Cb are trans Z is either (A) methylene, and R13 is (i) COOR4 (where R4 is alkyl, phenyl or benzyl) or is (ii) R10 (where R10 is alkyl substd. by halogen or halocarbonyl or is alkylcarbonyl, cycloalkylcarbonyl, cycloalkyl-alkylcarbonyl, haloalkylcarbonyl R14 and R15 together are alkylene, or (iii) R13 is H, alkyl, cycloalkyl, cycloalkenyl or alkyl substd. by e.g. alkenyl, alkynyl, OH, amino (itself opt. substd.) benzoyl or phenyl (opt. ring substd.), phenoxycarbonyl, benzoxycarbonyl, and R14 and R15 are H, or R14 is W and R15 is V (where either V and W is H and the other is (CH2)L9 (where L9 is a leaving gp.) or either R14 or R15 is H and the other is hydroxyethyl or R14 and R15 are (CO)s-(CH2)t-(CO)u (where s+t+u is 1-3, and at least 1 of s and u is 1) or (B) Z is Co or CHOH and R13 is as above, and R14 and R15 are alkylene.