BR112015014669A2 - pirrolobenzodiazepinas e conjugados das mesmas - Google Patents

pirrolobenzodiazepinas e conjugados das mesmas

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Publication number
BR112015014669A2
BR112015014669A2 BR112015014669A BR112015014669A BR112015014669A2 BR 112015014669 A2 BR112015014669 A2 BR 112015014669A2 BR 112015014669 A BR112015014669 A BR 112015014669A BR 112015014669 A BR112015014669 A BR 112015014669A BR 112015014669 A2 BR112015014669 A2 BR 112015014669A2
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BR
Brazil
Prior art keywords
alkyl
group
saturated
optionally substituted
halo
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BR112015014669A
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English (en)
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BR112015014669B1 (pt
Inventor
Wilson Howard Philip
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Spirogen Sarl
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Application filed by Spirogen Sarl filed Critical Spirogen Sarl
Publication of BR112015014669A2 publication Critical patent/BR112015014669A2/pt
Publication of BR112015014669B1 publication Critical patent/BR112015014669B1/pt

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • 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
    • 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
    • A61K47/6889—Conjugates wherein the antibody being the modifying agent and wherein the linker, binder or spacer confers particular properties to the conjugates, e.g. peptidic enzyme-labile linkers or acid-labile linkers, providing for an acid-labile immuno conjugate wherein the drug may be released from its antibody conjugated part in an acidic, e.g. tumoural or environment
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Cell Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

resumo “pirrolobenzodiazepinas e conjugados das mesmas” um composto com a fórmula i: e sais e solvatos do mesmo, em que: quando houver uma ligação dupla presente entre c2 e c3, r2 é selecionado dentre o grupo que consiste de: (ia) grupo arila c5-10, opcionalmente substituído por um ou mais substituintes selecionados dentre o grupo compreendendo: halo, nitro, ciano, éter, alquila c1-7, heterociclila c3-7 e bis-oxi-c1-3 alquileno; (ib) alquila c1-5 alifática saturada; (ic) cicloalquila c3-6 saturada; (id) , em que cada um dentre r11, r12 e r13 é independente-mente selecionado dentre h, alquila c1 3 saturada, alquenila c2-3, alquinila c2-3 e ciclopropil, onde o número total de átomos de carbono no grupo r2 não é maior do que 5; (ie) , em que um dentre r15a e r15b é h e o outro é selecio-nado dentre: fenila, fenila esta que é opcionalmente substituída por um grupo selecionado dentre halo, metila, metóxi, piridil; e tiofenila; e (if) , onde r14 é selecionado dentre: h; alquila c1-3 saturada; alquenila c2-3; alquinila c2-3; ciclopropil; fenila, fenila esta que é opcionalmente substituída por um grupo selecionado dentre halo, metila, metóxi; piridil; e tiofenila; quando houver uma ligação simples presente entre c2 e c3, r2 e , onde r16a e r16b são independentemente selecionados dentre h, f, alquila c1-4 saturada, alquenila c2-3, grupos alquila e alquenila estes que são opcionalmente substituídos por um grupo selecionado dentre alquil amido c1-4 e éster alquílico c1-4; ou, quando um dentre r16a e r16b for h, o outro é selecionado dentre nitrilo e um éster alquílico c1-4; quando houver uma ligação dupla presente entre c2’ e c3’, r12 é selecionado dentre o grupo que consiste de: (ia) grupo arila c5-10, opcionalmente substituído por um ou mais substituintes selecionados dentre o grupo compreendendo: halo, nitro, ciano, carbóxi, éster, alquila c1-7, heterociclila c3-7 e bis-oxi-c1-3 alquileno; (ib) alquila c1-5 alifática saturada; (ic) cicloalquila c3-6 saturada; (id) , em que cada um dentre r21, r22 e r23 é independentemen-te selecionado dentre h, alquila c1 3 saturada, alquenila c2-3, alquinila c2-3 e ciclo-propil, onde o número total de átomos de carbono no grupo r12 não é maior do que 5; (ie) , em que um dentre r25a e r25b é h e o outro é selecionado dentre: fenila, fenila esta que é opcionalmente substituída por um grupo selecionado dentre halo, metila, metóxi, piridil; e tiofenila; e (if) , onde r24 é selecionado dentre: h; alquila c1-3 saturada; al-quenila c2-3; alquinila c2-3; ciclopropil; fenila, fenila esta que é opcionalmente substituída por um grupo selecionado dentre halo, metila, metóxi; piridil; e tiofenila; quando houver uma ligação simples presente entre c2’ e c3’, r12 é , onde r26a e r26b são independentemente selecionados dentre h, f, alquila c1-4 saturada, alquenila c2-3, grupos alquila e alquenila estes que são opcionalmente substituídos por um grupo selecionado dentre alquil amido c1-4 e éster alquílico c1-4; ou, quando um dentre r26a e r26b é h, o outro é selecionado dentre nitrilo e um éster alquílico c1-4; r6 e r9 são selecionados independentemente dentre h, r, oh, or, sh, sr, nh2, nhr, nrr’, nitro, me3sn e halo; em que r e r’ são selecionados independentemente dentre grupos alquila c1-12 opcionalmente substituída, heterociclila c3-20 e arila c5-20; r7 é selecionado dentre h, r, oh, or, sh, sr, nh2, nhr, nrrr’, nitro, me3sn e halo; r? é um grupo alquileno c3-12, cadeia esta que pode ser interrompida por um ou mais heteroátomos, por exemplo, o, s, nrn2 (onde rn2 é h ou alquila c1-4), e/ou anéis aromáticos, por exemplo, benzeno ou piridina; y e y’ são selecionados dentre o, s ou nh; r6’, r7’, r9’ são selecionados dentre os mesmos grupos que r6, r7 e r9, respectivamente; r20 é h ou me e tanto r21a quanto r21b são h ou juntos formam =o; rl é um peptídeo conector para conexão com um agente de ligação celular; r11b é selecionado dentre oh, ora, onde ra é alquila c1-4 e sozm, onde z é 2 ou 3 e m é um cátion monovalente farmaceuticamente aceitável.
BR112015014669-4A 2012-12-21 2013-12-20 Compostos pirrolobenzodiazepinas, conjugados compreendendo os mesmos e uso destes para tratar uma doença proliferativa BR112015014669B1 (pt)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261740592P 2012-12-21 2012-12-21
US61/740,592 2012-12-21
PCT/EP2013/077705 WO2014096368A1 (en) 2012-12-21 2013-12-20 Pyrrolobenzodiazepines and conjugates thereof

Publications (2)

Publication Number Publication Date
BR112015014669A2 true BR112015014669A2 (pt) 2017-10-10
BR112015014669B1 BR112015014669B1 (pt) 2023-09-26

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ID=49886925

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BR112015014669-4A BR112015014669B1 (pt) 2012-12-21 2013-12-20 Compostos pirrolobenzodiazepinas, conjugados compreendendo os mesmos e uso destes para tratar uma doença proliferativa

Country Status (11)

Country Link
US (1) US9562049B2 (pt)
EP (1) EP2935268B2 (pt)
JP (1) JP6307519B2 (pt)
CN (2) CN105189507A (pt)
AU (1) AU2013366493B2 (pt)
BR (1) BR112015014669B1 (pt)
CA (1) CA2894961C (pt)
EA (1) EA031585B1 (pt)
ES (1) ES2658888T5 (pt)
HK (1) HK1216638A1 (pt)
WO (1) WO2014096368A1 (pt)

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JP6307519B2 (ja) 2018-04-04
CN105189507A (zh) 2015-12-23
AU2013366493B2 (en) 2017-08-24
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US20150344482A1 (en) 2015-12-03
JP2016508130A (ja) 2016-03-17
CN110452242A (zh) 2019-11-15
EA031585B1 (ru) 2019-01-31
US9562049B2 (en) 2017-02-07
EP2935268B2 (en) 2021-02-17
ES2658888T5 (es) 2021-10-19
HK1216638A1 (zh) 2016-11-25
CA2894961A1 (en) 2014-06-26
EP2935268B1 (en) 2017-11-22
EP2935268A1 (en) 2015-10-28
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AU2013366493A1 (en) 2015-07-09

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