Protein kinase C modulators. C. indolactam structural-types with anti-inflammatory activity

A compound of the formula:

• P.sub.2 --S.sub.x --E.sub.1
• wherein P.sub.2 is a radical of the formula:
• ##STR41## in the form of an individual isomer, an isomer mixture, a racemate or optical antipode, or a pharmaceutically acceptable salt thereof;
• wherein B.sup.1 completes a 6-membered aromatic ring which may be carbocyclic or may optionally contain a nitrogen atom at any of positions 5, 6 and 7 of the ring wherein the maximum number of nitrogen atoms at positions 5, 6 and 7 is two, wherein positions 5, 6 and/or 7 are optionally and independently substituted on any carbon by a halogen or by a straight chain or branched chain, cyclic or acyclic, saturated or unsaturated or aromatic carbon- and/or heteroatom-containing group which, taken together, contain not more than 40 carbon atoms, not more than 24 halogen atoms and not more than 9 heteroatoms selected from the group consisting of oxygen, nitrogen, silicon, phosphorus and sulfur, the groups being optionally connected to one another and/or to B.sup.2 to form 1-3 additional rings;
• B.sup.2 may be selected from the group consisting of oxygen, sulfur, sulfoxide, sulfone, monofluoromethylene, difluoromethylene and a carbon or nitrogen atom optionally substituted by straight chain or branched chain, cyclic or acyclic, saturated or unsaturated or aromatic carbon- and/or heteroatom-containing groups having not more than 15 carbon atoms, not more than 24 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen, silicon, phosphorus and sulfur, or B.sup.2 may be linked to B.sup.1 or K.sup.1 to form an additional carbocyclic or heterocyclic ring;
• B.sup.3 is a 2-carbon chain, which carries S.sub.x E.sub.1, and is optionally substituted by halogen(s) and/or one or more straight chain or branched chain, cyclic or acyclic, saturated or unsaturated or aromatic carbon- and/or heteroatom-containing groups which, taken together but excluding S.sub.x E.sub.1, contain not more than 12 carbon atoms, not more than 6 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
• provided that, including S.sub.x E.sub.1, the carbon atom of B.sup.3 bonded to K.sup.2 as defined below does not carry --CH.sub.2 OH or --CH(CH.sub.3)OH;
• K.sup.1 may be selected from the group consisting of hydrogen, halogen and a straight chain or branched chain, cyclic or acyclic, saturated or unsaturated or aromatic carbon- and/or heteroatom-containing group containing not more than 15 carbon atoms, not more than 18 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen, silicon, phosphorus and sulfur, or K.sup.1 may be linked to B.sup.2 or B.sup.3 or to both B2 and B3 to form one or more additional carbocyclic and/or heterocyclic rings;
• K.sup.2 is selected from the group consisting of oxygen, sulfur, --NK.sup.6 -- and --CK.sup.6 K.sup.7 --, wherein K.sup.6 is selected from the group consisting of hydrogen, hydroxy, methyl, ethyl, fluoro, n-propyl, allyl and propargyl, and wherein K.sup.7 is selected from the group consisting of hydrogen, methyl, ethyl, halogen, trifluoromethyl and cyano;
• K.sup.3 and K.sup.4 may independently be selected from the group consisting of hydrogen, halogen and a straight chain or branched chain, cyclic or acyclic, saturated or unsaturated or aromatic carbon- and/or heteroatom-containing group, or may complete an additional ring connecting K.sup.3 and K.sup.4 or connecting either K.sup.3 or K.sup.4 to K.sup.5, such that K.sup.3 and K.sup.4 taken together contain not more than 18 carbon atoms, not more than 24 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen, silicon, phosphorus and sulfur;
• K.sup.5 is selected from the group consisting of oxygen, sulfur, sulfoxide, sulfone, --NK.sup.8 --, --NOK.sup.8 -- and --CK.sup.8 K.sup.9 --, wherein K.sup.8 is hydrogen or a straight chain or branched chain, cyclic or acyclic, saturated or unsaturated or aromatic carbon-and/or heteroatom-containing group containing not more than 30 carbon atoms, not more than 24 halogen atoms and not more than 8 heteroatoms selected from the group consisting of oxygen, nitrogen, silicon, phosphorus and sulfur, and wherein K.sup.9 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, hydroxy, halogen, allyl, propargyl, cyano and trifluoromethyl;
• provided that P.sub.2 S.sub.x E.sub.1 may not comprise (-)-1,10,14-O-trimethylindolactam V, and provided that if B.sup.1 completes an unsubstituted or substituted carbocyclic aromatic ring, and
• B.sup.2 is selected from the group consisting of --NH--, --N--(C.sub.1 -C.sub.12 linear or branched, saturated or unsaturated alkyl or alkanoyl)--, --N--COOCH.sub.2 C.sub.6 H.sub.5 -- and --N--COOC(CH.sub.3).sub.3 --, and
• B.sup.3 is --CH.sub.2 CH--, and
• K.sup.1 is hydrogen, and
• K.sup.2 is --NH--, and
• K.sup.4 is hydrogen, and
• K.sup.5 is selected from the group consisting of --NH-- and --N(C.sub.1 -C.sub.3 -alkyl)--, then:
• (i) if S.sub.x E.sub.1 is bonded to the carbon atom in B.sup.3 that is adjacent to K.sup.2, then S.sub.x E.sub.1 is not --COOMe or --COOEt;
• and (ii) if S.sub.x is a single bond directed to the carbon atom in B.sup.3 that is adjacent to K.sup.2, and E.sub.1 is --CH.sub.2 --R.sub.e.sup.e then R.sub.e.sup.e is not selected from the group consisting of hydrogen, chloro, bromo, C.sub.1 -C.sub.12 saturated or unsaturated, linear or branched alkoxy, CH.sub.3 OCH.sub.2 O--, C.sub.1 -C.sub.12 linear or branched alkanoyloxy, bromoacetoxy, benzoyloxy, azidobenzoyloxy, 3,5--(CH.sub.3).sub.2 --C.sub.6 H.sub.3 COO--, methanesulfonyloxy, toluenesulfonyloxy, dansyloxy, (tetrahydro-2H-pyran-2-yl)oxy and (C.sub.1 -C.sub.6 linear or branched alkyl).sub.n (phenyl).sub.3-n silyloxy wherein n is 0-3;
• wherein S.sub.x is selected from the group consisting of S.sub.B, S.sub.1, S.sub.2, S.sub.3, S.sub.5 and S.sub.6 ;
• wherein S.sub.B is a single or double bond;
• wherein S.sub.1 is a chain of atoms of the formula:
• ##STR42## wherein a, b, d, e, and g may independently be from 0 to 3;
• c and f may independently be 0 or 1;
• the sum of (a+b+c+d+e+f+g) is at least 1 but not more than 12;
• and
• if c and f are both 1, then the sum of (d+e) must be at least 1;
• wherein S.sub.2 is a chain of atoms of the formula:
• ##STR43## wherein h, i, k, m, p, and q may be independently be from 0 to 3;
• j and n may independently be 0 or 1;
• if j and n are both 1 and l is 0, then the sum of (k+m) must be at least 1;
• if n is 1 and o is 0, then the sum of (p+q) must be at least 1;
• the sum of (l+o) is 1-3;
• and the sum of (h+i+j+k+2l+m+n+2o+p+q) is at least 1 but not more than 12;
• wherein S.sub.3 is a chain of atoms of the formula:
• ##STR44## wherein r, s, u, y, a', and b' may independently be from 0 to 3;
• the sum of (t+z) is 0 or 1;
• the sum of (v+w+x) is 1;
• the sum of (y+z+a'+b') is at least 1;
• the sum of (r+s+2t+u+2v+3w+4x+y+2z+a'+b') is at least 1 but not than 12;
• wherein S.sub.5 is a chain of atoms defined by:
• ##STR45## wherein j', k', m', q', and s' may independently be from 0 to 3;
• l' and r' may each be 0 or 1, but the sum of (l'+r') must be 1 or 2;
• n' and p' may each be 0 or 1, but the sum of (n'+p') must be 0 or 1;
• the value of o' may be 0-2;
• if the sum of (n'+p') is 1 and l' is 0, then q' must be at least 1;
• if the sum of (n'+p') is 1 and r' is 0, then m' must be at least 1;
• the sum of (j'+k'+l'+m'+n'+o'+p'+q'+r'+s') is at least 1 but not more than 12;
• wherein S.sub.6 is a chain of atoms defined by:
• ##STR46## wherein u', v', x', y', z' and m" may each be 0 or 1;
• t' and a" may each independently be 0-6;
• the sum of (t'+u'+v'+2w'+x'+2y'+z'+a") must be 0-8;
• b", d", e", f", h", j", k" and n" may each independently be 0 or 1;
• c", g", i", and l" may each independently be 0-3;
• if d" and j" are both 1, then the sum of (g"+i") must be at least 1;
• if either j" or k" is 1, then l" must be at least 1;
• if b" is 1, then the sum of (c"+g"+h"+i"+l") must be at least 1;
• if d" is 1, then the sum of (g"+h"+i"+l") must be at least 1;
• the sum of (t'+u'+v'+2w'+x'+2y'+z'+a"+b"+c"+d"+e"+2f"+g"+2h"+i"+j"+k"+l") must be 0-14;
• if m" is zero, R.sub.3.sup.6 or R.sub.6.sup.4 may optionally comprise an additional bond, thereby completing an unsaturated linkage to G.sup.2 ;
• if n" and b" are zero, R.sub.6.sup.5 or R.sub.6.sup.6 may optionally comprise an additional bond, thereby completing an unsaturated linkage to G.sup.2 ;
• one of the substituents R.sub.6.sup.1 -R.sub.6.sup.4 and/or one of the substituents R.sub.6.sup.5 -R.sub.6.sup.12 may optionally comprise the same or different values of G.sup.1, as defined below;
• wherein, for S.sub.1 -S.sub.6, R.sub.1.sup.1 through R.sub.6.sup.12 may independently be selected from the group consisting of hydrogen, halogen and a saturated or singly or doubly unsaturated, straight or branched acyclic substituent containing not more than 20 carbon atoms, not more than 16 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, silicon and phosphorus such that for any substituent the oxygen, nitrogen, silicon, phosphorus and sulfur atoms must be situated in functional groups selected from the group consisting of hydroxy, amino, hydroxylamine, tertiary amine oxide, Schiff's base, hydrazine, thiol, nitro, nitroso, oxime, azide, ether, acetal, ketal, thioether, aldehyde, keto, hydrazone, carboxy, mercaptocarbonyl, mercaptothionocarbonyl, sulfonate, sulfonyl, sulfoxide, phosphate, phosphonate, phosphate ester, phosphonate ester, phosphine, phosphine oxide, thionophosphine, phosphite, phosphonium, phosphorothioate, thionophosphate ester, thiophosphonate, thionophosphonate ester, silane, silanol, silanediol, fluorinated silane, ester, amide, cyano, hydrazide, carbonate, carbamate, urea, isourea, carboxamidine, imidate, guanidine, thioester, thioamide, thiocarbonate, dithiocarbonate, thiocarbamate, dithiocarbamate, thiourea, isothiourea, thioimidate, nitroguanidine, cyanoguanidine and xanthate;
• one substituent selected from the group consisting of R.sub.1.sup.1, R.sub.1.sup.2, R.sub.2.sup.1, R.sub.2.sup.2, R.sub.3.sup.1, R.sub.3.sup.2, R.sub.5.sup.1, R.sub.5.sup.2, R.sub.6.sup.1 and R.sub.6.sup.2 may optionally comprise an additional bond, thereby completing an unsaturated linkage to P.sub.2 ;
• one or two of the substituents R.sub.1.sup.1 -R.sub.5.sup.12 may optionally comprise the same or different values of G.sup.1, as defined below;
• one substituent selected from the group consisting of R.sub.1.sup.11, R.sub.1.sup.12, R.sub.2.sup.11, R.sub.2.sup.12, R.sub.3.sup.11, R.sub.3.sup.12, R.sub.5.sup.11, R.sub.5.sup.12, R.sub.6.sup.11 and R.sub.6.sup.12 may optionally comprise an additional bond, thereby completing an unsaturated linkage to E.sub.1 ;
• one of the substituents R.sub.1.sup.1 -R.sub.6 .sup.12 may be linked to either the atom in P.sub.2 that carries the S.sub.x chain or to an atom in P.sub.2 adjacent thereto, to form a saturated or unsaturated or aromatic, carbocyclic or heterocyclic 4-8 membered ring containing 0-4 identical or different hetero ring members selected from the group consisting of --O--, --S--, --S(O)--, --S(O).sub.2 --, --C(O)--, --NH-- and .dbd.N--, the ring being optionally substituted by 1-8 identical or different substituents selected from the group consisting of halogen, hydroxy, methoxy, ethoxy, methyl, ethyl, cyano, azide, nitro, hydroxymethyl, 1-hydroxyethyl, 2-hydroxy-2-propyl, CF.sub.3, OCF.sub.3, SH, SCH.sub.3, SOCH.sub.3, SCF.sub.3, COOH, COOCH.sub.3, COCH.sub.3, CH.dbd.O, acetoxy, amino, mono- or dialkylamino totaling 1-4 carbon atoms inclusive, acetamido, N-methylacetamido, carboxamido, N-alkylated carboxamido containing 1-4 carbon atoms inclusive, hydroxyacetyl and hydroxyacetoxy;
• provided that, for any given S.sub.1, S.sub.2, S.sub.3, S.sub.5 or S.sub.6 but excluding P.sub.2 and E.sub.1 :
• the total of carbon atoms is 25 or less;
• the total of halogen atoms is 16 or less;
• the total of oxygen atoms is 6 or less;
• the total of nitrogen atoms is 4 or less;
• the sulfur, silicon and phosphorus atoms each total 3 or less;
• and the total of oxygen, nitrogen, silicon, phosphorus and sulfur atoms together is 8 or less;
• the total of --OH groups is 3 or less;
• the total of --NH.sub.2 groups is 2 or less;
• the total of --SH groups is 2 or less;
• the total of --OH, --SH and --NH.sub.2 groups together is 4 or less;
• X, X' and X" are independently selected from the group consisting of:
• ##STR47## wherein R.sub.X.sup.1, R.sub.X.sup.2, R.sub.X.sup.11 and R.sub.X.sup.12 may independently be hydrogen;
• R.sub.X.sup.1 through R.sub.X.sup.12 may independently be a saturated or singly or doubly unsaturated, straight or branched acyclic substituent containing 1-20 carbon atoms, not more than 16 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, such that for any substituent the oxygen atoms total 4 or less, the nitrogen atoms total 4 or less and the sulfur atoms total 2 or less, the heteroatoms being situated in functional groups selected from the group consisting of hydroxy, amino, thiol, nitro, azide, ether, thioether, aldehyde, keto, carboxy, ester, amide, cyano, carbamate, urea, carboxamidine, guanidine, thioester, thioamide, thiocarbamate, thiourea, nitroguanidine and cyanoguanidine;
• wherein said functional groups are separated from the atom to which R.sub.X.sup.1 -R.sub.X.sup.12 is attached by at least two carbon atoms;
• R.sub.X.sup.4, R.sub.X.sup.5, R.sub.X.sup.11 and R.sub.X.sup.12 may independently be hydroxy;
• R.sub.X.sup.1 may optionally represent an additional bond, thereby completing an unsaturated linkage to P.sub.2 ;
• and
• one or two of the substituents R.sub.X.sup.1 -R.sub.X.sup.12 may optionally comprise the same or different values of G.sup.1, as defined below;
• wherein Y and Y' are independently selected from the group consisting of:
• ##STR48## wherein R.sub.Y.sup.1 and R.sub.Y.sup.2, and R.sub.Y.sup.3 and R.sub.Y.sup.4, each pair being cis or trans relative to one another, may independently be hydrogen or a saturated or unsaturated, straight or branched acyclic substituent containing not more than 20 carbon atoms, not more than 16 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, such that for any substituent the oxygen atoms total 4 of less, the nitrogen atoms total 4 or less and the sulfur atoms total 2 or less, the heteroatoms being situated in functional groups as defined for R.sub.X.sup.1 -R.sub.X.sup.5 ;
• R.sub.Y.sup.1 and R.sub.Y.sup.2 may also independently be a halogen;
• one or two of the substituents R.sub.Y.sup.1 -R.sub.Y.sup.4 may optionally comprise the same or different values of G.sup.1, as defined below;
• one of the substituents selected from the group consisting of R.sub.X.sup.1 -R.sub.X.sup.12 and R.sub.Y.sup.1 -R.sub.Y.sup.4 may be linked to either the atom in P.sub.2 that carries the chain containing X, X', X", Y and/or Y' or to an atom in P.sub.2 adjacent thereto, to form a 4-8 membered ring defined as for the analogous R.sub.1.sup.1 -R.sub.6.sup.12 -containing ring above;
• wherein Z' is selected from the group consisting of:
• ##STR49## Z.sup.2 is selected from the group consisting of:
• ##STR50## Z.sup.3 is selected from the group consisting of:
• ##STR51## Z.sup.4 and Z.sup.4' independently are:
• ##STR52## and Z.sup.5 and Z.sup.5' independently are selected from the group consisting of:
• ##STR53## wherein R.sub.Z.sup.26 may be any of the values specified for R.sub.X.sup.1 -R.sub.X.sup.12 above;
• R.sub.Z.sup.18 and R.sub.Z.sup.19 may independently be selected from the group consisting of --O--, --S-- and --NR.sub.Z.sup.21 -- wherein R.sub.Z.sup.21 may be selected from the group consisting of hydrogen, C.sub.1-4 alkyl, 2-hydroxyethyl, 2-hydroxy-n-propyl, 2-acetoxyethyl and 2-acetoxy-n-propyl;
• R.sub.Z.sup.17 and R.sub.Z.sup.20 may independently be hydrogen or a substituent selected from the group consisting of C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, phenoxy or thiophenoxy and amino optionally mono- or disubstituted by C.sub.1-4 alkyl or monosubstituted by a substituent selected from the group consisting of cyano, nitro and phenyl (optionally substituted by moieties selected from the group consisting of halogen, hydroxy, hydroxymethyl, thiol, carboxy, carboxymethyl, amino and nitro);
• R.sub.Z.sup.1 -R.sub.Z.sup.16 , R.sub.Z.sup.22 -R.sub.Z.sup.25 and R.sub.Z.sup.27 -R.sub.Z.sup.30 may independently be hydrogen or a saturated or unsaturated substituent selected from the group consisting of C.sub.1-6 alkyl, C.sub.1-6 halogenated alkyl, cyclohexyl and phenyl or benzyl;
• R.sub.Z.sup.1 -R.sub.Z.sup.4, R.sub.Z.sup.7, R.sub.Z.sup.10, R.sub.Z.sup.12, R.sub.Z.sup.13 and R.sub.Z.sup.27 -R.sub.Z.sup.30 may also be independently selected from the group consisting of C.sub.1-6 acyl, C.sub.1-6 halogenated acyl, C.sub.2-6 monohydroxyacyl and C.sub.2-6 hydroxyalkyl;
• R.sub.Z.sup.5 and R.sub.Z.sup.6 may also be independently selected from the group consisting of C.sub.1-6 hydroxyalkyl, C.sub.1-6 alkoxy and C.sub.1-6 hydroxyalkoxy;
• R.sub.Z.sup.8, R.sub.Z.sup.9, R.sub.Z.sup.23 and R.sub.Z.sup.24 may also independently be C.sub.2-6 hydroxyalkyl;
• one of the substituents R.sub.Z.sup.1 -R.sub.Z.sup.17, R.sub.Z.sup.20, R.sub.Z.sup.21, R.sub.Z.sup.22 and R.sub.Z.sup.25 may be linked to either the atom in P.sub.2 that carries the chain containing Z.sup.1, Z.sup.2 or Z.sup.3 or to an atom in P.sub.2 adjacent thereto, to form a saturated or unsaturated or aromatic, carbocyclic or heterocyclic 4-8 membered ring containing 0-4 identical or different hetero ring members selected from the group consisting of O, S, .dbd.N-- and NH, the ring being optionally substituted on its carbon and/or NH members by 1-8 identical or different substituents selected from the group consisting of halogen, hydroxy, methoxy, ethoxy, methyl, ethyl, cyano, azide, nitro, hydroxymethyl, 1-hydroxyethyl, 2-hydroxy-2-propyl, CF.sub.3, OCF.sub.3, SH, SCH.sub.3, SOCH.sub.3, SCF.sub.3, COOH, COOCH.sub.3, COCH.sub.3, CH.dbd.O, acetoxy, amino, mono- or dialkylamino totaling 1-4 carbon atoms inclusive, acetamido, N-methylacetamido, carboxamido, N-alkylated carboxamido containing 1-4 carbon atoms inclusive, hydroxyacetyl and hydroxyacetoxy;
• R.sub.Z.sup.26 may comprise G.sup.1 as defined below, and an optional ring may be formed between R.sub.Z.sup.26 and P.sub.2 as described above for R.sub.1.sup.1 -R.sub.6.sup.12 ;
• R.sub.Z.sup.1, R.sub.Z.sup.4, R.sub.Z.sup.7, R.sub.Z.sup.26 or R.sub.Z.sup.27 may comprise an additional bond, thereby completing an unsaturated linkage to P.sub.2 ;
• only one of the substituents R.sub.Z.sup.1 -R.sub.Z.sup.25 may be substituted or unsubstituted phenyl or benzyl;
• wherein M and M' are independently selected from the group consisting of:
• ##STR54## wherein R.sub.M.sup.1 and R.sub.M.sup.2 may independently be hydrogen or a saturated or singly or multiply unsaturated, straight or branched acyclic substituent containing 1-20 carbon atoms, not more than 16 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, in which the oxygen atoms total 4 or less, the nitrogen atoms total 4 or less and the sulfur atoms total 2 or less, the heteroatoms being situated in functional groups selected from the group consisting of hydroxy, amino, thiol, nitro, azide, ether, thioether, aldehyde, keto, carboxy, ester, amide, cyano, nitroguanidine and cyanoguanidine;
• R.sub.M.sup.1 may optionally comprise an additional bond, thereby completing an unsaturated linkage to P.sub.2 ;
• R.sub.M.sup.1 or R.sub.M.sup.2 may optionally comprise the same or different values of G.sub.1, as defined below;
• and
• R.sub.M.sup.1 or R.sub.M.sup.2 may be linked to either the atom in P.sub.2 that carries the chain containing M and/or M' or to an atom in P.sub.2 adjacent thereto, to form a 4-8 membered ring defined as for the analogous R.sub.1.sup.1 -R.sub.6.sup.12 -containing ring above;
• wherein R.sup.Q -R.sup.Q"' are independently selected from the group consisting of:
• ##STR55## wherein and R.sub.Q.sup.3 and R.sub.Q.sup.4 may independently be selected from the group consisting of halogen, hydrogen and a saturated or singly or multiply unsaturated, straight or branched acyclic substituent containing 1-20 carbon atoms, not more than 16 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, in which the oxygen atoms total 4 or less, the nitrogen atoms total 4 or less and the sulfur atoms total 2 or less, the heteroatoms being situated in functional groups selected from the group consisting of hydroxy, amino, thiol nitro, azide, ether, thioether, aldehyde, keto, carboxy, ester, amide, cyano, nitroguanidine and cyanoguanidine;
• R.sub.Q.sup.3 and/or R.sub.Q.sup.4 may optionally comprise the same or different values of G.sup.1, as defined below;
• one of R.sub.Q.sup.3 and R.sub.Q.sup.4 may be linked to either the atom in P.sub.2 bonded to the chain that carries R.sup.Q or to an atom in P.sub.2 adjacent thereto, to form a 4-8 membered ring defined as for the analogous R.sub.1.sup.1 -R.sub.6.sup.12 -containing ring above;
• wherein Q, Q' and Q"' are independently selected from the group consisting of:
• ##STR56## and wherein Q" is selected from the group consisting of:
• ##STR57## wherein R.sub.Q.sup.1 and R.sub.Q.sup.2 may independently be hydrogen or a saturated or singly or multiply unsaturated, straight or branched acyclic substituent containing 1-20 carbon atoms, not more than 16 halogen atoms and not more than 6 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, in which the oxvgen atoms total 4 or less, the nitrogen atoms total 4 or less and the sulfur atoms total 2 or less, the heteroatoms being situated in functional groups selected from the group consisting of hydroxy, amino, thiol, nitro, azide, ether, thioether, aldehyde, keto, carboxy, ester, amide, cyano, nitroguanidine and cyanoguanidine;
• R.sub.Q.sup.1 and/or R.sub.Q.sup.2 may optionally comprise the same or different values of G.sup.1, as defined below;
• R.sub.Q.sup.1 may be linked to either the atom in P.sub.2 that carries the chain containing Q and/or Q' or to an atom in P.sub.2 adjacent thereto, to form a 4-8 membered ring defined as for the analogous R.sub.1.sup.1 -R.sub.6.sup.12 -containing ring above;
• wherein G.sup.1 and G.sup.2 independently comprise a group containing 1-3 fused or separate, saturated or unsaturated or aromatic, carbocyclic or heterocyclic 4-8 membered rings, each ring containing 0-4 identical or different hetero ring members selected from the group consisting of --O--, --S--, --S(O)--, --S(O).sub.2 --, --C(O)--, --NH-- and .dbd.N--, each ring being optionally substituted on its carbon and/or NH members by 1-8 identical or different substituents selected from the group consisting of halogen, hydroxy, methoxy, ethoxy, methyl, ethyl, cyano, azide, nitro, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxy-2-propyl, CF.sub.3, OCF.sub.3, SH, SCH.sub.3, SOCH.sub.3, SCF.sub.3, COOH, COOCH.sub.3, COCH.sub.3, CH.dbd.O, acetoxy, amino, mono- or dialkylamino totaling 1-4 carbon atoms inclusive, acetamido, N-methylacetamido, carboxamido, N-alkylated carboxamido containing 1-4 carbon atoms inclusive, hydroxyacetyl and hydroxyacetoxy;
• wherein for G.sup.1 the optional second and third rings may be fused to the first ring and/or to one another or may be separate rings connected to one another and/or to the atom bearing G.sup.1 by a single or double bond or by an intervening substituted or unsubstituted, linear or branched, saturated or unsaturated chain containing not more than 8 carbon atoms, not more than 8 halogens and not more than 4 heteroatoms selected from the group consisting of oxygen, nitrogen, silicon, phosphorus and sulfur;
• and wherein for G.sup.2 the first ring is singly or doubly bonded to P.sub.2 or to a component atom of the S.sub.6 chain connecting P.sub.2 and G.sup.2, and the optional second and third rings may be fused to the first ring or to one another or may be separate rings connected to one another and/or to the first ring by single or double bonds or by an intervening substituted or unsubstituted, linear or branched, saturated or unsaturated chain containing not more than 8 carbon atoms, not more than 8 halogens and not more than 4 heteroatoms selected from the group consisting of oxygen, nitrogen, silicon, phosphorus and sulfur;
• wherein E.sub.1 is selected from the group consisting of .dbd.O, .dbd.S, .dbd.NH, .dbd.NOR.sub.E.sup.8 wherein R.sub.E.sup.8 is selected from the group consisting of hydrogen and a C.sub.1 -C.sub.8 normal or branched alkyl radical, .dbd.N--NH.sub.2, hydrogen, halogen, --OH, --SH, --NH.sub.2, --NH--NH.sub.2, --N.sub.3, --CN, --NO, --NO.sub.2, --NHOH, --ONH.sub.2, ##STR58## wherein T.sup.1 is selected from the group consisting of --O--, --S-- and --NH--;
• T.sup.2 is selected from the group consisting of .dbd.O, .dbd.S and .dbd.N--R.sub.E.sup.6 wherein R.sub.E.sup.6 is selected from the group consisting of hydrogen, hydroxy, cyano and nitro;
• T.sup.2 is selected from the group consisting of .dbd.O and .dbd.S;
• T.sup.3, T.sup.4 and T.sup.4' may independently be selected from the group consisting of hydrogen, --OH, --NH.sub.2, --SH, --N.sub.3, --NH--NH.sub.2 and --NH--OR.sub.E.sup.7 wherein R.sub.E.sup.7 is selected from the group consisting of hydrogen, C.sub.1-3 alkyl and C.sub.1-3 acyl;
• T.sup.3 may also be hydrogen or halogen;
• T.sup.5 is selected from the group consisting of hydrogen, halogen and hydroxy;
• T.sup.5' and T.sup.5" are independently hydrogen or hydroxy;
• R.sub.E.sup.1 is selected from the group consisting of hydrogen, halogen, hydroxy, nitro, nitroso, cyano, azide, --NH.sub.2, --NH--OH, --SH, --O--NH.sub.2, --NH--NH.sub.2, --T.sup.1 --C(.dbd.T.sup.2)--T.sup.3, --C(.dbd.T.sup.2)--T.sup.3, --SiT.sup.5 T.sup.5' T.sup.5", --T.sup.1 --S(.dbd.O)(.dbd.T.sup.2)--T.sup.4, --S(.dbd.O)(.dbd.T.sup.2)--T.sup.4, --T.sup.1 --P(--T.sup.4)--T.sup.4', --P(--T.sup.4)--T.sup.4', --T.sup.1 --P(.dbd.T.sup.2)(--T.sup.3)--T.sup.4 and --P(.dbd.T.sup.2')(--T.sup.3)--T.sup.4 ;
• R.sub.E.sup.2 and R.sub.E.sup.3 may individually be selected from the group consisting of hydrogen, --C(.dbd.T.sup.2)--T.sup.3, cyano, nitro, azide, halogen and a C.sub.1 -C.sub.15 straight or branched chain, saturated or unsaturated or aromatic-containing alkyl moiety optionally containing not more than 10 halogen atoms and not more than 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
• if R.sub.E.sup.1 is cyano or --C(.dbd.T.sup.2)--T.sup.3, then R.sub.E.sup.2 or R.sub.E.sup.3 may optionally be selected from --SiT.sup.5 T.sup.5' T.sup.5", --T.sup.1 --P(.dbd.T.sup.2')(--T.sup.3)--T.sup.4 and --P(.dbd.T.sup.2')(--T.sup.3)--T.sup.4 ;
• and
• R.sub.E.sup.4 and R.sub.E.sup.5 are individually selected from the group consisting of hydrogen, halogen, cyano, nitro, --C(.dbd.T.sup.2)--T.sup.3, --T.sup.1 --C(.dbd.T.sup.2)--T.sup.3, --CR.sub.E.sup.1 R.sub.E.sup.2 R.sub.E.sup.3, --SiT.sup.5 T.sup.5' T.sup.5", --S(.dbd.O)(.dbd.T.sup.2)--T.sup.4 and --P(.dbd.T.sup.2')(--T.sup.3)--T.sup.4.