MX364330B - Pirrolobenzodiazepinas y conjugados de las mismas. - Google Patents

Pirrolobenzodiazepinas y conjugados de las mismas.

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Publication number
MX364330B
MX364330B MX2015012276A MX2015012276A MX364330B MX 364330 B MX364330 B MX 364330B MX 2015012276 A MX2015012276 A MX 2015012276A MX 2015012276 A MX2015012276 A MX 2015012276A MX 364330 B MX364330 B MX 364330B
Authority
MX
Mexico
Prior art keywords
group
alkyl
halo
independently selected
optionally substituted
Prior art date
Application number
MX2015012276A
Other languages
English (en)
Other versions
MX2015012276A (es
Inventor
Wilson Howard Philip
Pillow Thomas
A Flygare John
Wei Binqing
Original Assignee
Medimmune Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Medimmune Ltd filed Critical Medimmune Ltd
Publication of MX2015012276A publication Critical patent/MX2015012276A/es
Publication of MX364330B publication Critical patent/MX364330B/es

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
    • 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
    • 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
    • A61K47/68035—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a pyrrolobenzodiazepine
    • 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
    • A61K47/6835—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 the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site
    • A61K47/6851—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 the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a determinant of a tumour cell
    • A61K47/6855—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 the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a determinant of a tumour cell the tumour determinant being from breast cancer cell
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
    • C07K16/18—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • C07K16/28—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
    • C07K16/2863—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants against receptors for growth factors, growth regulators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
    • C07K16/40—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against enzymes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K2317/00—Immunoglobulins specific features
    • C07K2317/90—Immunoglobulins specific features characterized by (pharmaco)kinetic aspects or by stability of the immunoglobulin
    • C07K2317/92—Affinity (KD), association rate (Ka), dissociation rate (Kd) or EC50 value

Abstract

La presente invención se refiere a un conjugado de la fórmula (A) (ver Fórmula) en donde: D representa cualquiera del grupo D1 o D2: (ver Fórmula) la línea punteada indica la presencia opcional de un enlace doble entre C2 y C3; cuando hay un enlace doble presente entre C2 y C3, R2 se selecciona del grupo que consiste de: (ia) grupo arilo C5-10, opcionalmente substituido por uno o más substituyentes seleccionados del grupo que comprende: halo, nitro, ciano, éter, carboxi, éster, alquilo C1-7, heterociclilo C3-7 y bis-oxi-alquileno C1-3; (ib) alquilo alifático saturado C1-5; (ic) cicloalquilo saturado C3-6; (id) (ver Fórmula) en donde cada uno de R31, R32 y R33 se seleccionan independientemente de H, alquilo saturado C1-3, alquenilo C2-3, alquinilo C2-3 y ciclopropilo, donde el número total de átomos de carbono en el grupo R2 no es más que 5; (ie) (ver Fórmula), en donde uno de R35a y R35b es H y el otro se selecciona de: fenilo, cuyo fenilo es opcionalmente substituido por un grupo seleccionado de halo, metilo, metoxi; piridilo; y tiofenilo; y (if) (ver Fórmula), donde R34 se selecciona de: H; alquilo saturado C1-3 alquenilo C2-3 alquinilo C2-3; ciclopropilo; fenilo, cuyo fenilo es opcionalmente substituido por un grupo seleccionado de halo, metilo, metoxi; piridilo; y tiofenilo; (ig) halo; cuando hay un enlace sencillo presente entre C2 yC3, R2 es (ver Fórmula) en donde R36a y R36b se seleccionan independientemente de H, F, alquilo saturado C1-4, alquenilo C2-3, cuyos grupos alquilo y alquenilo son opcionalmente substituidos por un grupo seleccionado de amido alquilo C1-4y éster alquilo C1-4 o, cuando uno de R16a y R16b es H, el otro se selecciona de nitrilo y un éster de alquilo C1-4; D' representa cualquiera de grupo D'1 o D'2: (ver Fórmula) en donde la línea punteada indica la presencia opcional de un enlace doble entre C2' y C3'; R6 y R9 se seleccionan independientemente de H, R, OH, OR, SH, SR, NH2, NHR, NRR', NO2, Me3Sn y halo; R7 está independientemente seleccionado de H, R, OH, OR, SR, SR, NR2, NHR, NRR', NO2, Me3Sn y halo; Y se selecciona de las fórmulas A1, A2, A3, A4, A5 y A6: (ver Fórmulas) n es un entero seleccionado en el intervalo de 0 hasta 48; RA4 es un grupo alquileno C1-6; cualquiera de (a) R10 es H, y R11 es OH, ORA, donde RA es alquilo C1-4; o (b) R10 y R11 forma un enlace doble nitrógeno-carbono entre los átomos de nitrógeno y carbono a los cuales se enlazan; o (c) R10 es H y R11 es OSOZM, donde z es 2 o 3 y M es un catión farmacéuticamente aceptable monovalente; R y R' son cada uno independientemente seleccionado de alquilo C1-12 opcionalmente substituido, heterociclilo C3-20 y grupos arilo C5-20, y opcionalmente en relación al grupo NRR', R y R' junto con el átomo de nitrógeno al cual se enlazan forman un anillo heterocíclico opcionalmente substituido de 4, 5, 6 o 7 miembros; en donde R16, R17, R19, R20, R21 y R22 son como se define para R6, R7, R9, R10, R11 y R2 respectivamente; en donde Z es CH o N; en donde T y T´´ se seleccionan independientemente de un enlace sencillo o un alquileno C1-9, cuya cadena se puede interrumpir por uno o más heteroátomos por ejemplo O, S, N(H), NMe, siempre que el número de átomos en la cadena más corta de átomos entre X y X' es 3 hasta 12 átomos; y X y X' se seleccionan independientemente de O, S y N(H); excepto que no puede haber enlaces dobles entre tanto C2 como C3 y C2' como C3'.
MX2015012276A 2013-03-13 2014-03-13 Pirrolobenzodiazepinas y conjugados de las mismas. MX364330B (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361778777P 2013-03-13 2013-03-13
US201361856351P 2013-07-19 2013-07-19
PCT/IB2014/001029 WO2014140862A2 (en) 2013-03-13 2014-03-13 Pyrrolobenzodiazepines and conjugates thereof

Publications (2)

Publication Number Publication Date
MX2015012276A MX2015012276A (es) 2017-03-06
MX364330B true MX364330B (es) 2019-04-23

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Family Applications (1)

Application Number Title Priority Date Filing Date
MX2015012276A MX364330B (es) 2013-03-13 2014-03-13 Pirrolobenzodiazepinas y conjugados de las mismas.

Country Status (14)

Country Link
US (1) US9649390B2 (es)
EP (1) EP2968594B1 (es)
JP (1) JP6340019B2 (es)
KR (1) KR102066318B1 (es)
CN (1) CN105142674B (es)
AU (1) AU2014229529B2 (es)
BR (1) BR112015021965B1 (es)
CA (1) CA2904044C (es)
ES (1) ES2731779T3 (es)
HK (1) HK1214140A1 (es)
MX (1) MX364330B (es)
NZ (1) NZ710746A (es)
WO (1) WO2014140862A2 (es)
ZA (1) ZA201505753B (es)

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CA2904044C (en) 2020-03-31
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BR112015021965B1 (pt) 2022-05-03
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