HRP20221063T1 - Konjugati pirolobenzodiazepina - Google Patents

Konjugati pirolobenzodiazepina Download PDF

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Publication number
HRP20221063T1
HRP20221063T1 HRP20221063TT HRP20221063T HRP20221063T1 HR P20221063 T1 HRP20221063 T1 HR P20221063T1 HR P20221063T T HRP20221063T T HR P20221063TT HR P20221063 T HRP20221063 T HR P20221063T HR P20221063 T1 HRP20221063 T1 HR P20221063T1
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Croatia
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image
compound according
represented
formula
conjugate
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HRP20221063TT
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English (en)
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Philip Wilson Howard
Stephen John Gregson
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Medimmune Limited
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Priority claimed from GBGB1706133.4A external-priority patent/GB201706133D0/en
Priority claimed from GBGB1721337.2A external-priority patent/GB201721337D0/en
Application filed by Medimmune Limited filed Critical Medimmune Limited
Publication of HRP20221063T1 publication Critical patent/HRP20221063T1/hr

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    • 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
    • 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
    • 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
    • A61K47/6835—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
    • A61K47/6835—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides

Claims (25)

1. Spoj, naznačen time, da je predstavljen formulom I: [image] i njegove soli i solvati, gdje: R6 i R9 se neovisno biraju od H, R, OH, OR, SH, SR, NH2, NHR, NRR', nitro, Me3Sn i halogena; pri čemu se R i R' neovisno biraju od opcionalno supstituiranih C1-12 alkil, C3-20 heterociklil i C5-20 aril skupina; R7 se bira od H, R, OH, OR, SH, SR, NH2, NHR, NRR', nitro, Me3Sn i halogena; R'' je C3-12 alkilen skupina čiji lanac može biti prekinut s jednim ili više heteroatoma, primjerice O, S, NRN2 (gdje RN2 predstavlja H ili C1-4 alkil), i/ili aromatskih prstenova, primjerice benzen ili piridin; Y i Y' se biraju od O, S, ili NH; R6', R7' i R9' se biraju od istih skupina kao i R6, R7 i R9, prema navedenom redoslijedu; R11b se bira od OH, ORA, pri čemu RA je C1-4 alkil; i RL je veznik za spajanje sa sredstvom za vezanje stanice, koji se bira od: (iiia): [image] gdje Q je: [image] pri čemu QX je takav da je Q aminokiselinski ostatak, dipeptidni ostatak ili tripeptidni ostatak; X je: [image] gdje a = 0 do 5, b = 0 do 16, c = 0 ili 1, d = 0 do 5; GL je veznik za spajanje s jedinicom liganda; i (iiib): [image] pri čemu se RL1 i RL2 neovisno biraju od H i metila, ili zajedno s ugljikovim atomom s kojim su vezani, tvore ciklopropilen ili ciklobutilen skupinu; i e je 0 ili 1; dok (a) R20 je H, i R21 je OH ili ORA, gdje RA je C1-4 alkil; ili (b) R20 i R21 tvore dvostruku vezu dušik-ugljik između dušikovog i ugljikovog atoma s kojima su vezani; ili (c) R20 je H, i R21 je SOzM, gdje z je 2 ili 3, i M je monovalentni farmaceutski prihvatljiv kation; ili (d) R20 je H, i R21 je H; ili (e) R21 je OH ili ORA, gdje RA je C1-4 alkil i R20 se bira od: [image] [image] [image] pri čemu se RZ bira od: [image] (z-ii) OC(=O)CH3; (z-iii) NO2; (z-iv) OMe; (z-v) glukoronid; (z-vi) -OC(=O)-X1-NHC(=O)X2-NH-RZC, pri čemu -OC(=O)-X1-NH- i -OC(=O)-X2-NH- predstavljaju prirodne aminokiselinske ostatke i RZC se bira od Me, OMe, OCH2CH2OMe.
2. Spoj prema patentnom zahtjevu 1, naznačen time, da oba Y i Y' su O, i R'' je: a) C3-7 alkilen; ili b) skupina s formulom: [image] , gdje r je 1 ili 2.
3. Spoj prema patentnom zahtjevu 1 ili zahtjevu 2, naznačen time, da R9 je H, i R6 je H.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da R7 je C1-4 alkoksi skupina.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da R6' je ista skupina kao R6, R7' je ista skupina kao R7, R9' je ista skupina kao R9, i Y' je ista skupina kao Y.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time, da R20 i R21 tvore dvostruku vezu dušik-ugljik između dušikovog i ugljikovog atoma s kojima su vezani.
7. Spoj prema patentnom zahtjevu 1, naznačen time, da je predstavljen formulom Ia, Ib ili Ic: [image] [image] [image] gdje se R1a bira od metila i benzila; RL i R11b su isti kao što su definirani u patentnom zahtjevu 1.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da R11b jest OH.
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da RL je predstavljen formulom IIIa, i Q je dipeptidni ostatak koji se bira od: CO-Phe-Lys-NH, CO-Val-Ala-NH, CO-Val-Lys-NH, CO-Ala-Lys-NH, CO-Val-Cit-NH, CO-Phe-Cit-NH, CO-Leu-Cit-NH, CO-Ile-Cit-NH, CO-Phe-Arg-NH, i CO-Trp-Cit-NH.
10. Spoj prema bilo kojem od patentnih zahtjeva 1 do 9, naznačen time, da je RL predstavljen formulom IIIa i a je 0.
11. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, naznačen time, da je RL predstavljen formulom IIIa i b je 0 do 8.
12. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11, naznačen time, da je RL predstavljen formulom IIIa i d je 2.
13. Spoj prema bilo kojem od patentnih zahtjeva 1 do 12, naznačen time, da je RL predstavljen formulom IIIa i GL se bira od sljedećih: [image] pri čemu Ar predstavlja C5-6 arilen skupinu.
14. Spoj prema patentnom zahtjevu 13, naznačen time, da GL jest GL1-1.
15. Spoj prema patentnom zahtjevu 1, naznačen time, da je spoj predstavljen formulom Id: [image] gdje se Q bira od: (a) -CH2-; (b) -C3H6-; i (c) [image]
16. Konjugat, naznačen time, da je predstavljen formulom II: L-(DL)p (II) pri čemu L je jedinica liganda, DL je povezna jedinica lijeka s formulom I': [image] pri čemu su R6, R7, R9, R11b, Y, R'', Y', R6', R7', R9', R20 i R21, isti kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 8; RLL je veznik za spajanje sa sredstvom za vezanje stanice, koji se bira od: (iiia): [image] gdje su Q i X isti kao što su definirani u bilo kojem od patentnih zahtjeva 1 i 9 do 12 i GLL je veznik koji je spojen s jedinicom liganda; i (iiib): [image] gdje su RL1 i RL2 isti kao što su definirani u patentnom zahtjevu 1; pri čemu p je cijeli broj od 1 do 20.
17. Konjugat prema patentnom zahtjevu 16, naznačen time, da se GLL bira od: [image] pri čemu Ar predstavlja C5-6 arilen skupinu.
18. Konjugat prema patentnom zahtjevu 17, naznačen time, da GLL jest GLL1-1.
19. Konjugat prema patentnom zahtjevu 16, naznačen time, da je DL predstavljen formulom (Id'): [image] gdje se Q bira od: (a) -CH2-; (b) -C3H6-; i (c) [image]
20. Konjugat prema bilo kojem od patentnih zahtjeva 16 do 19, naznačen time, da jedinica liganda je protutijelo ili njegov aktivni fragment koji se veže na jedan ili više antigena povezanih s tumorom ili na receptorne površine stanice odabrane od (1) do (88): (1) BMPR1B; (2) E16; (3) STEAP1; (4) 0772P; (5) MPF; (6) Napi3b; (7) Sema 5b; (8) PSCA hlg; (9) ETBR; (10) MSG783; (11) STEAP2; (12) TrpM4; (13) CRIPTO; (14) CD21; (15) CD79b; (16) FcRH2; (17) HER2; (18) NCA; (19) MDP; (20) IL20R-alfa; (21) Brevican; (22) EphB2R; (23) ASLG659; (24) PSCA; (25) GEDA; (26) BAFF-R; (27) CD22; (28) CD79a; (29) CXCR5; (30) HLA-DOB; (31) P2X5; (32) CD72; (33) LY64; (34) FcRH1; (35) IRTA2; (36) TENB2; (37) PSMA-FOLH1; (38) SST; (38.1) SSTR2; (38.2) SSTR5; (38.3) SSTR1; (38.4) SSTR3; (38.5) SSTR4; (39) ITGAV; (40) ITGB6; (41) CEACAM5; (42) MET; (43) MUC1; (44) CA9; (45) EGFRvIII; (46) CD33; (47) CD19; (48) IL2RA; (49) AXL; (50) CD30 - TNFRSF8; (51) BCMA - TNFRSF17; (52) CT Ags - CTA; (53) CD174 (Lewis Y) – FUT3; (54) CLEC14A; (55) GRP78 – HSPA5; (56) CD70; (57) specifični antigeni matične stanice; (58) ASG-5; (59) ENPP3; (60) PRR4; (61) GCC – GUCY2C; (62) Liv-1 – SLC39A6; (63) 5T4; (64) CD56 – NCMA1; (65) CanAg; (66) FOLR1; (67) GPNMB; (68) TIM-1 – HAVCR1; (69) RG-1/Mindin, meta za tumor prostate – Mindin/RG-1; (70) B7-H4 – VTCN1; (71) PTK7; (72) CD37; (73) CD138 – SDC1; (74) CD74; (75) Klaudini – CLs; (76) EGFR; (77) Her3; (78) RON – MST1R; (79) EPHA2; (80) CD20 – MS4A1; (81) Tenaskin C - TNC; (82) FAP; (83) DKK-1; (84) CD52; (85) CS1 – SLAMF7; (86) Endoglin - ENG; (87) Aneksin A1 – ANXA1; (88) V-CAM (CD106) – VCAM1.
21. Konjugat prema bilo kojem od patentnih zahtjeva 16 do 20, naznačen time, da p je cijeli broj od 1 do 8.
22. Konjugat prema bilo kojem od patentnih zahtjeva 16 do 21, naznačen time, da je za uporabu u liječenju.
23. Farmaceutski pripravak, naznačen time, da sadrži konjugat prema bilo kojem od patentnih zahtjeva 16 do 21, i farmaceutski prihvatljiv razrjeđivač, nosač ili pomoćno sredstvo.
24. Konjugat prema bilo kojem od patentnih zahtjeva 16 do 21, ili farmaceutski pripravak prema patentnom zahtjevu 23, naznačen time, da je za uporabu u liječenju proliferativne bolesti kod pojedinca.
25. Konjugat za uporabu prema patentnom zahtjevu 24, naznačen time, da bolest koja se liječi jest rak.
HRP20221063TT 2017-04-18 2018-04-18 Konjugati pirolobenzodiazepina HRP20221063T1 (hr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB1706133.4A GB201706133D0 (en) 2017-04-18 2017-04-18 Pyrrolobenzodiazepine conjugates
GBGB1721337.2A GB201721337D0 (en) 2017-12-19 2017-12-19 Pyrrolobenzodiazepine conjugates
EP18718452.8A EP3612537B1 (en) 2017-04-18 2018-04-18 Pyrrolobenzodiazepine conjugates
PCT/EP2018/059846 WO2018192944A1 (en) 2017-04-18 2018-04-18 Pyrrolobenzodiazepine conjugates

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HRP20221063T1 true HRP20221063T1 (hr) 2022-11-11

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US (1) US11370801B2 (hr)
EP (1) EP3612537B1 (hr)
JP (2) JP2020517609A (hr)
KR (1) KR102189731B1 (hr)
CN (1) CN110582505B (hr)
AU (1) AU2018255876B2 (hr)
BR (1) BR112019021942A2 (hr)
CA (1) CA3059519C (hr)
DK (1) DK3612537T3 (hr)
ES (1) ES2926144T3 (hr)
HR (1) HRP20221063T1 (hr)
HU (1) HUE059828T2 (hr)
IL (1) IL269945B (hr)
LT (1) LT3612537T (hr)
MX (1) MX2019012467A (hr)
PL (1) PL3612537T3 (hr)
PT (1) PT3612537T (hr)
RS (1) RS63502B1 (hr)
SI (1) SI3612537T1 (hr)
WO (1) WO2018192944A1 (hr)
ZA (1) ZA201906675B (hr)

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