BR112015021965A2 - pirrolobenzodiazepinas e conjugados das mesmas - Google Patents

pirrolobenzodiazepinas e conjugados das mesmas

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Publication number
BR112015021965A2
BR112015021965A2 BR112015021965A BR112015021965A BR112015021965A2 BR 112015021965 A2 BR112015021965 A2 BR 112015021965A2 BR 112015021965 A BR112015021965 A BR 112015021965A BR 112015021965 A BR112015021965 A BR 112015021965A BR 112015021965 A2 BR112015021965 A2 BR 112015021965A2
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BR
Brazil
Prior art keywords
group
alkyl
halo
independently selected
optionally substituted
Prior art date
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BR112015021965A
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English (en)
Other versions
BR112015021965B1 (pt
Inventor
Wei Binqing
A Flygare John
Wilson Howard Philip
Pillow Thomas
Original Assignee
Medimmune Ltd
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Application filed by Medimmune Ltd filed Critical Medimmune Ltd
Publication of BR112015021965A2 publication Critical patent/BR112015021965A2/pt
Publication of BR112015021965B1 publication Critical patent/BR112015021965B1/pt

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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

resumo “pirrolobenzodiazepinas e conjugados das mesmas” um conjugado da fórmula (a): em que: d representa o grupo d1 ou d2: ; a linha pontilhada indica a presença opcional de uma ligação dupla entre c2 e c3; quando existe uma ligação dupla presente entre c2 e c3, r2 é selecionado a partir do grupo que consiste de: (ia) grupo arila c5-10 opcionalmente substituído por um ou mais substituintes selecionados a partir do grupo que compreende: halo, nitro, ciano, éter, carbóxi, éster, alquila c1-7, heterociclila c3-7 e bis-óxi-alquileno c1-3; (ib) alquila alifático saturado c1-5; (ic) cicloalquila saturado c3-6; (id) , em que cada um entre r31, r32 e r33 é, independentemente, selecionado a partir de h, alquila saturado c1-3, alquenila c2-3, alquinila c2-3 e ciclopropila, onde o número total de átomos de carbono no grupo r2 é de não mais do que 5; (ie) , em que um entre r35a e r35b é h e o outro é selecionado a partir de: fenila, em que fenila é opcionalmente substituído por um grupo selecionado a partir de halo, metila, metóxi; piridila; e tiofenila; e (if) , onde r34 é selecionado a partir de: h; alquila saturado c1-3; alquenila c2-3; alquinila c2-3; ciclopropila; fenila, em que fenila é opcionalmente substituído por um grupo selecionado a partir de halo, metila, metóxi; piridila; e tiofenila; (ig) halo; quando existe uma ligação única presente entre c2 e c3, r2 é , onde r36a e r36b são, independentemente, selecionados a partir de h, f, alquila saturado c1-4, alquenila c2-3, em que os grupos alquila e alquenila são opcionalmente substituídos por um grupo selecionado a partir de alquilamido c1-4 e éster alquílico c1-4; ou, quando um entre r16a e r16b é h, o outro é selecionado a partir de nitrila e um éster alquílico c1-4; d’ representa o grupo d’1 ou d’2: em que a linha pontilhada indica a presença opcional de uma ligação dupla entre c2’ e c3’; r6 e r9 são, independentemente, selecionados a partir de h, r, oh, or, sh, sr, nh2, nhr, nrr’, no2, me3sn e halo; r7 é, independentemente, selecionado a partir de h, r, oh, or, sh, sr, nh2, nhr, nrr’, no2, me3sn e halo; y é selecionado a partir das fórmulas a1, a2, a3, a4, a5 e a6: (a1) (a2) (a3) (a4) (a5) (a6) l é um ligador conectado a um agente de ligação celular; cba é o agente de ligação celular; n é um número inteiro selecionado na faixa de 0 a 48; ra4 é um grupo alquileno c1-6; (a) r10 é h, e r11 é oh, ora, onde ra é alquila c1-4; ou (b) r10 e r11 formam uma ligação dupla nitrogênio-carbono entre os átomos de nitrogênio e carbono aos quais eles são ligados; ou (c) r10 é h e r11 é osozm, onde z é 2 ou 3 e m é um cátion monovalente farmaceuticamente aceitável; r e r’ são, independentemente, selecionados a partir de alquila c1-12 opcionalmente substituído, grupos heterociclila c3-20 e arila c5-20, e, opcionalmente, em relação ao grupo nrr’, r e r’ juntamente com o átomo de nitrogênio a qual eles são ligados formam um anel heterocíclico de 4, 5, 6 ou 7 membros opcionalmente substituído; em que r16, r17, r19, r20, r21 e r22 são definidos para r6, r7, r9, r10, r11 e r2, respectivamente; em que z é ch ou n; em que t e t’’ são, independentemente, selecionados a partir de uma ligação única ou um alquileno c1-9, em que a cadeia pode ser interrompida por um ou mais heteroátomos, por exemplo, o, s, n(h), nme, contanto que o número de átomos na cadeia mais curta de átomos entre x e x’ seja de 3 a 12 átomos; e x e x’ são, independentemente, selecionados a partir de o, s e n(h); exceto que não pode ocorrer ligações duplas entre c2
BR112015021965-9A 2013-03-13 2014-03-13 Conjugados e compostos de pirrolobenzodiazepinas, composição farmacêutica, uso dos mesmos para o tratamento de uma doença proliferativa e método de síntese dos ditos compostos BR112015021965B1 (pt)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361778777P 2013-03-13 2013-03-13
US61/778,777 2013-03-13
US201361856351P 2013-07-19 2013-07-19
US61/856,351 2013-07-19
PCT/IB2014/001029 WO2014140862A2 (en) 2013-03-13 2014-03-13 Pyrrolobenzodiazepines and conjugates thereof

Publications (2)

Publication Number Publication Date
BR112015021965A2 true BR112015021965A2 (pt) 2017-07-18
BR112015021965B1 BR112015021965B1 (pt) 2022-05-03

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BR112015021965-9A BR112015021965B1 (pt) 2013-03-13 2014-03-13 Conjugados e compostos de pirrolobenzodiazepinas, composição farmacêutica, uso dos mesmos para o tratamento de uma doença proliferativa e método de síntese dos ditos compostos

Country Status (14)

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

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