CA2150785A1 - Conjugates of methyltrithio antitumor agents and intermediates for their synthesis - Google Patents

Conjugates of methyltrithio antitumor agents and intermediates for their synthesis

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Publication number
CA2150785A1
CA2150785A1 CA002150785A CA2150785A CA2150785A1 CA 2150785 A1 CA2150785 A1 CA 2150785A1 CA 002150785 A CA002150785 A CA 002150785A CA 2150785 A CA2150785 A CA 2150785A CA 2150785 A1 CA2150785 A1 CA 2150785A1
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alkyl
bond
nconhr
ncoor
alk2
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CA2150785C (en
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Philip Ross Hamann
Lois Hinman
Irwin Hollander
Ryan Holcomb
William Hallett
Hwei-Ru Tsou
Martin J. Weiss
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Wyeth Holdings LLC
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American Cyanamid Co
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/6807—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug or compound being a sugar, nucleoside, nucleotide, nucleic acid, e.g. RNA antisense
    • A61K47/6809—Antibiotics, e.g. antitumor antibiotics anthracyclins, adriamycin, doxorubicin or daunomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Abstract

This invention describes carrier-drug conjugates prepared from disulfide analogs of the calicheamicin family of potent antitumor antibiotics and their derivatives, as well as similar analogs from related antitumor antibiotics such as the esperamicins. The carrier can be an antibody, growth factor, or steroid which targets an undesired population of cells, such as those of a tumor. Whole protein carriers as well as their antigen-recognizing fragments and their chemically or genetically manipulated counterparts are useful for the targeting portion of the conjugates. This invention includes compounds required for the synthesis of these conjugates, appropriate pharmaceutical compositions of the carrier-drug conjugates, and their method of use.

Claims (44)

1. A cytotoxic drug conjugate of formula:
Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m wherein Z3 is a protein selected from mono- and polyclonal antibodies, their antigen-recognizing fragments, and their chemically or genetically manipulated counterparts and/growth factors and their chemically or genetically manipulated counterparts, wherein a covalent bond to the protein is an amide formed from reaction with "m" lysine side chains, or a steroid, wherein the covalent bond to the steroid is an amide or an ester;
Alk1 and Alk2 are independently a bond or branched or unbranched (C1-C10) alkylene chain;
Sp1 is a bond, -S-, -O-, -CONH-, -NHCO-, -NR'-, -N(CH2CH2)2N-, or -X-Ar'-Y-(CH2)n-Z wherein X, Y, and Z are independently a bond, -NR'-, -S-, or -O-, with the proviso that when n = 0, then at least one of Y
and Z must be a bond and Ar' is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR', with the proviso that when Alk1 is a bond, SP1 is a bond;
n is an integer from 0 to 5;
R' is a branched or unbranched (C1-C5 ) chain optionally substituted by one or two groups of -OH, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, (C1-C3) dialkylamino, or (C1-C3) trialkylammonium -A- where A- is a pharmaceutically acceptable anion completing a salt;
Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1 or a 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, or 2,7-naphthylidene or , each naphthylidene or phenothiazine optionally substituted with one, two, three, or four groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1, with the proviso that when Ar is naphthylidene, Z1 is not hydrogen and with the proviso that when Ar in phenothiazine, Sp1 is a bond only connected to nitrogen;
Sp2 is a bond, -S-, or -O-, with the proviso that when Alk2 is a bond, Sp2 is a bond;
Z1 is H, (C1-C5) alkyl, or phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1;
Z2 is Q-Sp-SS-W, wherein W is or CH3; R2 is or H;

or H; or H;
R6 or R7 is H or ;

R5 is -CH3, -C2H5, or -CH (CH3)2; X is an iodine or bromine atom; R5' is a hydrogen or the group RCO, wherein R is hydrogen, branched or unbranched (C1 -C10) alkyl or (C1 - C10) alkylene group, a (C6-C11) aryl group, a (C6-C11) aryl-alkyl (C1 - C5) group, or a heteroaryl or heteroaryl-alkyl (C1 - C5) group wherein heteroaryl is 2- or 3-furyl, 2- or 3-thienyl,
2- or 3-(N-methylpyrrolyl), 2-, 3-, or 4-pyridyl, 2-, 4-, or 5-(N-methylimidizolyl), 2-, 4-, or 5-oxazolyl, 2-, 3-, 5-, or 6-pyrimidinyl, 2-, 3-, 4-, 5-, 6-, 7-, or 8-quinolyl, or 1-, 3-, 4-, 5-, 6-, 7-, or 8-isoquinolyl, all aryl and heteroaryl optionally substituted by one or more hydroxy, amino, carboxy, halo, nitro, lower (C1 - C3) alkoxy, or lower (C1 -C5) thioalkoxy groups;
Sp is a straight or branched-chain divalent or trivalent (C1 - C18) radical, divalent or trivalent aryl or heteroaryl radical, divalent or trivalent (C3 - C18) cycloalkyl or heterocycloalkyl radical, divalent or trivalent aryl- or heteroaryl-alkyl (C1 - C18) radical, divalent or trivalent cycloalkyl- or heterocycloalkyl-alkyl (C1 - C18) radical or divalent or trivalent (C2 - C18) unsaturated alkyl radical, wherein heteroaryl is furyl, thienyl, N-methylpyrrolyl, pyridinyl, N-methylimidizolyl, oxazolyl, pyrimidinyl, quinolyl, isoquinolyl, N-methylcarbazoyl, aminocoumarinyl, or phenazinyl and wherein if Sp is a trivalent radical, Sp can be additionally substituted by lower (C1 - C5) dialkylamino, lower (C1 - C5) alkoxy, hydroxy, or lower (C1 - C5) alkylthio groups; and Q is =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, or =NHO-m is an integer from about 0.1 to 15.
2. A cytotoxic drug conjugate according to claim 1 wherein Alk2 is a branched or unbranched (C1-C10) alkylene chain and Z1 is phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1.
3. A cytotoxic drug conjugate according to claim 1 wherein Alk2 is a branched or unbranched (C1-C10) alkylene chain and Z1 is H or (C1-C5) alkyl.
4. A cytotoxic drug conjugate according to claim 1 wherein Alk2 and Sp2 are together a bond and Z1 is H or (C1-C5) alkyl.
5. A cytotoxic drug conjugate according to claim 1 wherein Alk2 and Sp2 are together a bond and Z1 is phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1.
6. A cytotoxic drug conjugate according to claim 2, claim 3, claim 4, or claim 5 wherein Sp1 is a bond, -S-, -O-, -CONH-, - NHCO-, or -NR' wherein n and R' are as defined in claim 1-, with the proviso that when Alk1 is a bond, Sp1 is a bond.
7. A cytotoxic drug conjugate according to claim 6 wherein Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1 or Ar is a 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, or 2,7-naphthylidene each optionally substituted with one, two, three, or four groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1;
8. A cytotoxic drug conjugate according to claim 7 wherein Z3 is a protein selected from mono- and polyclonal antibodies, their antigen-recognizing fragments, and their chemically or genetically manipulated counterparts and growth factors and their chemically or genetically manipulated counterparts, wherein a covalent bond to the protein is an amide formed from reaction with "m" lysine side chains.
9. A cytotoxic drug conjugate according to claim 8 wherein Z2 is Q-Sp-SS-W, wherein W is R1 is ; R2 is or H;

R4 is or H;

R5, X, R5', R, and Sp are as defigned in claim 1; and Q is =NHNCO-.
10. A cytotoxic drug conjugate according to claim 9 wherein Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1, Alk2 and Sp2 are together a bond, and Z1 is H or (C1-C5) alkyl.
11. A cytotoxic drug conjugate according to claim 10 wherein Sp1 is -O-, Alk1 is C4 alkyl, Ar is 1,4-phenylene, and Z1 is C1 alkyl.
12. A cytotoxic drug conjugate according to claim 11 wherein Z3 is antibody h- or m-P67.6, h- or m-CT-M-01, h- or m-A33, or anti-Tac and Z2 is calicheamicin gamma dimethyl hydrazide or calicheamicin N-acetyl gamma dimethyl hydrazide.
13. A cytotoxic drug conjugate according to claim 12 wherein Z3 is antibody h-CT-M-01 and Z2 is Calicheamicin N-acetyl gamma dimethyl hydrazide.
14. A cytotoxic drug conjugate according to claim 12 wherein Z3 is antibody h-P67.6 and Z2 is Calicheamicin N-acetyl gamma dimethyl hydrazide.
15. A compound of the formula:

Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m Z3 is halogen, hydroxy, OM wherein M is a metal completing a salt, -N3, , , , , ;
,or Alk1 and Alk2 are independently a bond or branched or unbranched (C1-C10) alkylene chain;
Sp1 is a bond, -S-, -O-, -CONH-, -NHCO-, -NR'-, -N(CH2CH2)2N-, or -X-Ar'-Y-(CH2)n-Z wherein X, Y, and Z are independently a bond, -NR'-, -S-, or -O-, with the proviso that when n = 0, then at least one of Y
and Z must be a bond and Ar' is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR', with the proviso that when Alk1 is a bond, Sp1 is a bond;
n is an integer from 0 to 5;
R' is a branched or unbranched (C1-C5) chain optionally substituted by one or two groups of -OH, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, (C1-C3) dialkylamino, or (C1-C3) trialkylammonium - A- where A- is a pharmaceutically acceptable anion completing a salt;
Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1 or a 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, or 2,7-naphthylidene or each naphthylidene or phenothiazine optionally substituted with one, two, three, or four groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR' or S(CH2)nCONHR' wherein n and R' are as defined in claim 1, with the proviso that when Ar is naphthylidene, Z1 is not hydrogen and with the proviso that when Ar in phenothiazine, Sp1 is a bond only connected to nitrogen;

Sp2 is a bond, -S-, or -O-, with the proviso that when Alk2 is a bond, Sp2 is a bond;
Z1 is H, (C1-C5) alkyl, or phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1;
Z2 is Q-Sp-SS-W, wherein W is R1 is or CH3; R2 is or H;

R3 is or H; R4 is or H;

R6 or R7 is H or ;

R5 is -CH3, -C2H5, or -CH(CH3)2; X is an iodine or bromine atom; R5' is a hydrogen or the group RCO, wherein R is hydrogen, branched or unbranched (C1 -C10) alkyl or (C1 - C10) alkylene group, a (C6-C11) aryl group, a (C6-C11) aryl-alkyl (C1 - C5) group, or a heteroaryl or heteroaryl-alkyl (C1 - C5) group wherein heteroaryl is 2- or 3-furyl, 2- or 3-thienyl, 2- or 3-(N-methylpyrrolyl), 2-, 3-, or 4-pyridyl, 2-, 4-, or 5-(N-methylimidizolyl), 2-, 4-, or 5-oxazolyl, 2-, 3-, 5-, or 6-pyrimidinyl, 2-, 3-, 4-, 5-, 6-, 7-, or 8-quinolyl, or 1-, 3-, 4-, 5-, 6-, 7-, or 8-isoquinolyl, all aryl and heteroaryl optionally substituted by one or more hydroxy, amino, carboxy, halo, nitro, lower (C1 - C3) alkoxy, or lower (C1 -C5) thioalkoxy groups;
Sp is a straight or branched-chain divalent or trivalent (C1 - C18) radical, divalent or trivalent aryl or heteroaryl radical, divalent or trivalent (C3 - C18) cycloalkyl or heterocycloalkyl radical, divalent or trivalent aryl- or heteroaryl-alkyl (C1 - C18) radical, divalent or trivalent cycloalkyl- or heterocycloalkyl-alkyl (C1 - C18) radical or divalent or trivalent (C2 - C18) unsaturated alkyl radical, wherein heteroaryl is furyl, thienyl, N-methylpyrrolyl, pyridinyl, N-methylimidizolyl, oxazolyl, pyrimidinyl, quinolyl, isoquinolyl, N-methylcarbazoyl, aminocoumarinyl, or phenazinyl and wherein if Sp is a trivalent radical, Sp can be additionally substituted by lower (C1 - C5) dialkylamino, lower (C1 - C5) alkoxy, hydroxy, or lower (C1 - C5) alkylthio groups;
Q is =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, or =NHO-;
and m is 1.
16. A compound according to claim 15 wherein Z3 is hydroxy, , or
17. A compound according to claim 16 wherein Alk2 is a branched or unbranched (C1-C10) alkylene chain and Z1 is phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1.
18. A compound according to claim 17 wherein Alk2 is a branched or unbranched (C1-C10) alkylene chain and Z1 is H or (C1-C5) alkyl.
19. A compound according to claim 18 wherein Alk2 and Sp2 are together a bond and Z1 is H or (C1-C5) alkyl.
20. A compound according to claim 19 wherein Alk2 and Sp2 are together a bond and Z1 is phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1.
21. A compound according to claim 17, claim 18, claim 19, or claim 20 wherein Sp1 is a bond, -S-, -O-, -CONH-, - NHCO-, or -NR' wherein R' is as hereinbefore defined-, with the proviso that when Alk1 is a bond, Sp1 is a bond.
22. A compound according to claim 21 wherein Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1 or a 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, or 2,7-naphthylidene each optionally substituted with one, two, three, or four groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1;
23. A compound according to claim 22 wherein Z2 is Q-Sp-SS-W, wherein W is ; R2 is or H;
R1 is R4 is or H;

R5, X, R5', R, and Sp are as defined in claim 1; and Q is =NHNCO-.
24. A compound according to claim 23 wherein Alk2 and Sp2 are together a bond, Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1, and Z1 is H or (C1-C5) alkyl.
25. A compound according to claim 24 wherein Sp1 is -O-, Alk1 is C4 alkyl.
Ar is 1,4-phenylene, and Z1 is C1 alkyl.
26. A compound according to claim 25 wherein Z2 is calicheamicin gamma dimethyl hydrazide or calicheamicin N-acetyl gamma dimethyl hydrazide.
27. A compound of the formula:

Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m Z3 is halogen, hydroxy, OM wherein M is a metal completing a salt, -N3, , , , ,or ;

Alk1 and Alk2 are independently a bond or branched or unbranched (C1-C10) alkylene chain;
Sp1 is a bond, -S-, -O-, -CONH-, -NHCO-, -NR'-, -N(CH2CH2)2N-, or -X-Ar'-Y-(CH2)n-Z wherein X, Y, and Z are independently a bond, -NR'-, -S-, or -O-, with the proviso that when n = 0, then at least one of y and z must be a bond and Ar' is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR', with the proviso that when Alk1 is a bond, Sp1 is a bond;
n is an integer from 0 to 5;
R' is a branched or unbranched (C1-C5) chain optionally substituted by one or two groups of -OH, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, (C1-C3) dialkylamino, or (C1-C3) trialkylammonium - A- where A- is a pharmaceutically acceptable anion completing a salt;
Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as hereinbefore defined or Ar is a 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, or 2,7-naphthylidene or each naphthylidene or phenothiazine optionally substituted with one, two, three, or four groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1, with the proviso that when Ar is naphthylidene, Z1 is not hydrogen and with the proviso that when Ar in phenothiazine, Sp1 is a bond only connected to nitrogen;

Sp2 is a bond, -S-, or -O-, with the proviso that when Alk2 is a bond, Sp2 is a bond;
Z1 is H, (C1-C5) alkyl, or phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 1;
Z2 is oxygen; and m is 1, with the proviso that when Ar is unsubstituted 2,6-naphthylene or 1,3- or 1,4-phenylene optionally substituted with one group of (C1-C6) alkyl or (C1-C5) alkoxy and Alk2 is a bond, then Sp1 is not a bond, -O-, or -NHCO-.
28. A compound according to claim 27 wherein Z3 is hydroxy, , or
29. A compound according to claim 28 wherein Alk2 is a branched or unbranched (C1-C10) alkylene chain and Z1 is phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 27.
30. A compound according to claim 28 wherein Alk2 is a branched or unbranched (C1-C10) alkylene chain and Z1 is H or (C1-C5) alkyl.
31. A compound according to claim 28 wherein Alk2 and Sp2 are together a bond and Z1 is H or (C1-C5) alkyl.
32. A compound according to claim 28 wherein Alk2 and Sp2 are together a bond and Z1 is phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 27.
33. A compound according to claim 29, claim 30, claim 31, or claim 32 wherein Sp1 is a bond, -S-, -O-, -CONH-, - NHCO-, or -NR' wherein R' is as hereinbefore defined-, with the proviso that when Alk1 is a bond, Sp1 is a bond.
34. A compound according to claim 33 wherein Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 27 or a 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, or 2,7-naphthylidene each optionally substituted with one, two, three, or four groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 27;
35. A compound according to claim 34 wherein Alk2 and Sp2 are together a bond, Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', or S(CH2)nCONHR' wherein n and R' are as defined in claim 27, and Z1 is H or (C1-C5) alkyl.
36. A pharmaceutical composition comprising a conjugate of claim 1 and a parentally-administrable medium.
37. A pharmaceutical composition comprising a conjugate of claim 13 or 14 and a parentally-administrable medium.
38. A method of controlling the growth of an undesirable cell comprising administering a conjugate of claim 1 to a patient.
39. A method of controlling the growth of an undesirable cell comprising administering a conjugate of claim 13 or 14 to a patient.
40. A method of claim 45 or 46 wherein the undesired cells are cancer cells in a mammalian species.
41. A freeze-dried pharmaceutical composition comprising a conjugate of claim 13 or 14 which is obtained by freeze-drying an approximately 1 mg/mL
solution of the conjugate dissolved in about 5 mM
sodium phosphate buffer at a pH of about 7.4 containing about 100 mM sodium chloride and about 100 mM sucrose.
42. A process for preparing the targeted derivatives Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m of compounds of formula Z2, wherein Z2 is Q-Sp-SS-W and W is R1 is or CH3; R2 is or H;

R3 is or H; R4 is or H;

R6 or R7 is H or ;

R5 is -CH3, -C2H5, or -CH (CH3)2; X is an iodine or bromine atom; R5' is a hydrogen or the group RCO, wherein R is hydrogen, branched or unbranched (C1-C10) alkyl or (C1-C10) alkylene group, a (C6-C11) aryl group, a (C6-C11) aryl-alkyl (C1-C5) group, or a heteroaryl or heteroaryl-alkyl (C1-C5) group wherein heteroaryl is 2- or 3-furyl, 2- or 3-thienyl, 2- or 3-(N-methylpyrrolyl), 2-, 3-, or 4-pyridyl, 2-, 4-, or 5-(N-methylimidazolyl), 2-, 4-, or 5-oxazolyl, 2-, 3-, 5-, or 6-pyrimidinyl, 2-, 3-, 4-, 5-, 6-, 7-, or 8-quinolyl, or 1-, 3-, 4-, 5-, 6-, 7-, or 8-isoquinolyl, all aryl and heteroaryl optionally substituted by one or more hydroxy, amino, carboxy, halo, nitro, lower (C1-C3) alkoxy, or lower (C1-C5) thioalkoxy groups;
Sp is a straight or branched-chain divalent or trivalent (C1-C18) radical, divalent or trivalent aryl or heteroaryl radical, divalent or trivalent (C3-C18) cycloalkyl or heterocycloalkyl radical, divalent or trivalent aryl- or heteroaryl-alkyl (C1-C18) radical, divalent or trivalent cycloalkyl- or heterocycloalkyl-alkyl (C1-C18) radical or divalent or trivalent (C2-C18) unsaturated alkyl radical, wherein heteroaryl is furyl, thienyl, N-methylpyrrolyl, pyridinyl, N-methylimidazolyl, oxazolyl, pyrimidinyl, quinolyl, isoquinolyl, N-methylcarbazoyl, aminocoumarinyl, or phenazinyl and wherein if Sp is a trivalent radical, Sp may be additionally substituted by lower (C1-C5) dialkylamino, lower (C1-C5) alkoxy, hydroxy, or lower (C1-C5) alkylthio groups; and Q is H2NHNCO-, H2NHNCS-, H2NHNCONH-, H2NHNCSNH-, or H2NO-,comprising reacting Z2 with a compound of formula HOCO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=O, wherein Alk1 and Alk2 are independently a bond or branched or unbranched (C1-C10) alkylene chain;
Sp1 is a bond, -S-, -O-, -CONH-, -NHCO-, -NR'-, -N(CH2CH2)2N-, or -X-Ar'-Y-(CH2)n-Z wherein X, Y, and Z are independently a bond, -NR'-, -S-, or -O-, with the proviso that when n = 0, then at least one of Y
and z must be a bond and Ar' is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, -COOR', -CONHR', -O(CH2)nCOOR', -S(CH2)nCOOR', -O(CH2)nCONHR', or -S(CH2)nCONHR', with the proviso that when Alk1 is a bond, Sp1 is a bond;
n is an integer from 0 to 5;
R' is a branched or unbranched (C1-C5) chain optionally substituted by one or two groups of -OH, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, (C1-C3) dialkylamino, or (C1-C3) trialkylammonium - A- where A- is a pharmaceutically acceptable anion completing a salt;
Sp2 is a bond, -S-, or -O-, with the proviso that when Alk2 is a bond, Sp2 is a bond;
Z1 is H, (C1-C5) alkyl, or phenyl optionally substituted with one, two, or three groups of (C1-C5) alkyl, (C1-C4) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, -COOR', -CONHR', -O(CH2)nCOOR', -S(CH2)nCOOR', -O(CH2)nCONHR', or -S(CH2)nCONHR' wherein n and R' are as hereinbefore defined;

Ar is 1,2-, 1,3-, or 1,4-phenylene optionally substituted with one, two, or three groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, or -COOR', -CONHR', -O(CH2)nCOOR', -S(CH2)nCOOR', -O(CH2)nCONHR', or -S(CH2)nCONHR' wherein n and R' are as hereinbefore defined or a 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, or 2,7-naphthylidene or each naphthylidene or phenothiazine optionally substituted with one, two, three, or four groups of (C1-C6) alkyl, (C1-C5) alkoxy, (C1-C4) thioalkoxy, halogen, nitro, -COOR', -CONHR', -O(CH2)nCOOR', -StCH2)nCOOR', -O(CH2)nCONHR', or -S(CH2)nCONHR' wherein n and R' are as hereinbefore defined, with the proviso that when Ar is naphthylidene, Z1 is not hydrogen and with the proviso that when Ar in phenothiazine, Sp1 is a bond only connected to nitrogen, in an alcoholic solvent with a boiling point of less than about 100°C in the presence of about 5% acetic acid or other similar acid catalyst at about 20° to 70°C for about 1-24 hours and isolating the intermediate of formula HOCO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2, wherein Alk1, Sp1, Ar, Sp2, Alk2, and Z1 are as hereinbefore defined;
Z2 is Q-Sp-SS-W wherein Sp and W are as hereinbefore defined; and Q is =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, or =NO-, then reacting the compound of formula HOCO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2 with N-hydroxysuccinimide, 2, 3, 5, 6-tetrafluorophenol, pentafluorophenol, 4-nitrophenol, 2,4-dinitrophenol, or other suitable activating group in the presence of DCC, EDCI, or other coupling agent in an inert organic solvent such as acetonitrile or acetonitrile containing 5-50% DMF to generate the compound Z3'CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2, wherein Alk1, Sp1, Ar, Sp2, Alk2, and Z1, are as hereinbefore defined;
Z2 is Q-Sp-SS-W wherein Sp and W are as hereinbefore defined;
Q is =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, or =NO-;
and , , , , , , or other comparable acid activating group, and finally reacting the compound Z3'CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2 with a carrier Z3, wherein Z3 is a protein selected from mono- and polyclonal antibodies, their antigen-recognizing fragments, and their chemically or genetically manipulated counterparts and growth factors and their chemically or genetically manipulated counterparts in an aqueous, buffered solution at a pH of between 6.5 and 9.0 and a temperature of 4° to 40°C for 1-48 hours to generate a compound of formula Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m, wherein Alk1, Sp1, Ar, Sp2, Alk2, Z1 and Z3, are as hereinbefore defined;
Z2 is Q-Sp-SS-W wherein Sp and W are as hereinbefore defined;
Q is =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, or =NO-;
and m is an integer from about 0.1 to 15 or by reacting a compound of formula HOCO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O, wherein Alk1, Sp1, Ar, Sp2, and Alk2 are as hereinbefore defined, with N-hydroxysuccinimide, 2, 3, 5, 6-tetrafluorophenol, pentafluorophenol, 4-nitrophenol, 2,4-dinitrophenol, of other suitable activating group in the presence of DCC, EDCI, or other coupling agent in an inert organic solvent such as acetonitrile or acetonitrile containing 5-50% DMF to generate the compound Z3'CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O

wherein Alk1, Sp1, Ar, Sp2, Alk2, and Z3' are as hereinbefore defined, and then reacting the compound Z3'CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O

with a carrier Z3, wherein Z3 is as hereinbefore defined, in an aqueous, buffered solution at a pH of between 6.5 and 9.0 and a temperature of 4° to 40°C
for 1-48 hours to generate a compound of formula Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O]m wherein Alk1, Sp1, Ar, Sp2, Alk2, Z3, and m are as hereinbefore defined, and finally reacting the compound Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O]m with a compound of formula Z2 wherein Z2 is Q-Sp-SS-W wherein Sp and W are as hereinbefore defined and Q is H2NHNCO-, H2NHNCS-, H2NHNCONH-, H2NHNCSNH-, or H2NO-,in an aqueous, buffered solution at a pH of between 4.0 and 6.0 and a temperature of 4° to 40°C for 1-48 hours to generate a compound of formula Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=Z2]m wherein Alk1, Sp1, Ar, Sp2, and Alk2, Z3, and m are as hereinbefore defined, Z2 is Q-Sp-SS-W wherein Sp and W are as hereinbefore defined, and Q is =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, or =NO-.
43. A cytotoxic drug conjugate according to claim 10 wherein Sp1 is -O- or a bond, Alk1 is a bond or branched or unbranched (C1-C10) alkylene chain, with the proviso that when Alk1 is a bond, Sp1 is a bond, Z1 is (C1-C5) alkyl, and Z2 is Calicheamicin N-acetyl gamma dimethyl hydrazide.
44. A protein carrier of formula:
Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m wherein Z3 is humanized P67.6 (h-P67.6) and m is zero.
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