FI3789042T3 - Menetelmä anti-her3-vasta-aine-lääkekonjugaatin valmistamiseksi - Google Patents

Menetelmä anti-her3-vasta-aine-lääkekonjugaatin valmistamiseksi Download PDF

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Publication number
FI3789042T3
FI3789042T3 FIEP20200710.0T FI20200710T FI3789042T3 FI 3789042 T3 FI3789042 T3 FI 3789042T3 FI 20200710 T FI20200710 T FI 20200710T FI 3789042 T3 FI3789042 T3 FI 3789042T3
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FI
Finland
Prior art keywords
maleimid
ggfg
chch
antibody
her3 antibody
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FIEP20200710.0T
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English (en)
Inventor
Thore Hettmann
Reimar Abraham
Sabine Blum
Suguru Ueno
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Daiichi Sankyo Co Ltd
Daiichi Sankyo Europe Gmbh
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Application filed by Daiichi Sankyo Co Ltd, Daiichi Sankyo Europe Gmbh filed Critical Daiichi Sankyo Co Ltd
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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Claims (22)

PATENTTIVAATIMUKSET
1. Menetelmä vasta-aine-lääkekonjugaatin val- mistamiseksi, joka menetelmä käsittää, että annetaan yhdisteen, jota edustaa seuraava kaava: (maleimid-N-yyli)- (CH) n”C (=0) -L?-LP-NH- (CH2) n! L3- (CH>) n?-C (=0) — (NH-DX) tai (maleimid-N-yyli)- (CH,)n?3C (=0) -L2-L?- (NH-DX) , reagoida anti-HER3-vasta-aineen tai sen reaktiivisen johdannaisen kanssa ja konjugoidaan lääke-linkkeriryhmä vasta-aineeseen menetelmällä tioeetterisidoksen muodos- tamiseksi disulfidisidosryhmään, joka on läsnä vasta- aineen sarana-alueella, jossa n? edustaa kokonaislukua 2 - 8, 1? edustaa ryhmää -NH- (CH.CH,-0O)n*-CH,CH,-C (=O) - tai yksöissidosta, jossa n' edustaa kokonais- lukua 1 - 6, IP edustaa peptiditähdettä, joka koostuu 2 - 7 aminohaposta, jotka valitaan fenyylialanii- nista, glysiinistä, valiinista, lysiinistä, sitrulliinista, seriinistä, alutamiinihaposta ja asparagiinihaposta, n! edustaa kokonaislukua 0 - 6, n? edustaa kokonaislukua 0 - 5, 13 edustaa -0-:ta tai yksöissidosta, ja - (maleimid-N-yyli)- on ryhmä, jota edustaa seuraava kaava: O a) O jossa typpiatomi on yhdistävä kohta, ja
- (NH-DX) edustaa ryhmää, jota edustaa seuraava kaava: RE 00 F N | / o HOF: Me” ? jossa aminoryhmän typpiatomi asemassa 1 on yh- distävä kohta.
2. Patenttivaatimuksen 1 mukainen menetelmä, jossa LF on tetrapeptiditähde -GGFG-.
3. Patenttivaatimuksen 1 mukainen menetelmä, jossa yhdiste on jokin valittuna seuraavasta ryhmästä: (maleimid-N-yyli)-CH,CH,-C (=O) -GGFG-NH-CH,CH,- C (=O) - (NH-DX) , (maleimid-N-yyli)-CH,CH,CH>,-C (=0) -GGFG-NH- CH,CH>,-C (=0) - (NH-DX), (maleimid-N-vyli) -CH,;CH:CH,CH>-C (=0) -GGFG-NH- CH,CH>,-C (=0) - (NH-DX), (maleimid-N-yyli) -CHCH:CHCH>CH>-C (=0) -GGFG- NH-CH,CH>-C (=O) - (NH-DX) , (maleimid-N-yyli)-CH,CH,-C (=O) -GGFG-NH- CHCH,CH>,-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH,CH,-C (=0) -GGFG-NH- CH,CH,CH,-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH,CH,CH,-C (=0) -GGFG-NH- CH,CH,CH,-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH.CH,CH-CH,-C (=0) -GGFG- NH-CH,CH,CH,-C (=O) - (NH-DX) , (maleimid-N-yyli)-CH>CH2-C (=O) -GGFG-NH- CH,CH,CH,CH,CH,-C (=O) - (NH-DX) , (maleimid-N-vyyli) -CHCH:CH>-C (=0) -GGFG-NH- CH,CH,CH,CH,CH,-C (=O) - (NH-DX),
(maleimid-N-yyli)-CH,CH-.CH,CH,-C (=0) -GGFG-NH- CH,CH,CH,CH,CH,-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH,CH,CH,CH,-C (=0) -GGFG- NH-CH,CH,CH,CH,CH,-C (=0) - (NH-DX) ,
(maleimid-N-yyli)-CH,CH,CH,CH-CH,-C (=0) -DGGFG- NH-CH,CH,-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH,CH,CH,CH,-C (=0) -DGGFG- NH-CH,CH,CH>,-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH,CH,CH-CH,-C (=0) -DGGFG-
NH-CH,CH,CH,CH,CH,-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH>CH2-C (=0) -GGFG-NH-CH>-O- CH,-C (=0) — (NH-DX) , (maleimid-N-yyli)-CH,CH-CH,-C (=0) -GGFG-NH-CH>,- 0-CH,-C (=O) - (NH-DX) ,
(maleimid-N-yyli)-CH,CH,CH,CH,-C (=0) -GGFG-NH- CH,-0-CH,-C (=O) - (NH-DX) , (maleimid-N-yyli)-CH,CH.CH,CH-CH,-C (=0) -GGFG- NH-CH>-O-CH>-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH,-C (=O) -GGFG-NH-CH,CH,-
O-CH>,-C (=0)- (NH-DX),
(maleimid-N-vyyli) -CHCH:CH>-C (=0) -GGFG-NH- CH,CH,-0-CH,-C (=O) - (NH-DX) , (maleimid-N-yyli)-CH,CH-.CH,CH,-C (=0) -GGFG-NH- CH,CH,-0-CH,-C (=0) - (NH-DX) ,
(maleimid-N-yyli)-CH,CH.CH,CH-CH,-C (=0) -GGFG- NH-CH,CH>-O-CH>-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH.-C (=0) -NH-CH:CH>-O- CH,CH,-0-CH,CH,-C (0) ~-GGFG-NH-CH,CH,-C (=O) - (NH- DX),
(maleimid-N-vyli)-CH>CH>-C (=0) -NH-CH:CH>-O- CHCH>-0-CH>CH>-0-CH>CH>-C (=0) -GGFG-NH-CH,CH,- C (=O) - (NH-DX) ,
(maleimid-N-vyli)-CH>CH>-C (=0) -NH-CH:CH>-O- CHCH>-0-CH>CH>-0-CH>CH>-0-CH>CH>-C (=0) -GGFG-NH- CH,CH>,-C (=0) - (NH-DX),
(maleimid-N-yyli)-CH,CH.-C (=0) -NH-CH:CH>-O- CH,CH,-0-CH,CH,-C (=0) ~-GGFG-NH-CH,CH,CH,-C (=0) - (NH-DX) ,
(maleimid-N-yyli)-CH,CH,-C (=0) -NH-CH,CH>-O-
CHCH>-0-CH>CH>-0-CH>CH>-C (=0) -GGFG-NH- CH,CH,CH,-C (=O) - (NH-DX) , (maleimid-N-vyli)-CH>CH>-C (=0) -NH-CH:CH>-O- CH,CH,-0-CH,CH,-0-CH,CH,-0-CH,CH,-C (=0) -GGFG-NH- CH,CH,CH,-C (=O) - (NH-DX) ,
(maleimid-N-yyli)-CH,CH.-C (=0) -NH-CH:CH>-O- CHCH>-0-CH>CH>-C (=0) -GGFG-NH-CH>»-0-CH>-C (=0) - (NH-DX) ,
(maleimid-N-vyli)-CH>CH>-C (=0) -NH-CH:CH>-O- CHCH>-0-CH>CH>-0-CH>CH>-C (=0) -GGFG-NH-CH,-0O-
CH,-C (=0) - (NH-DX),
(maleimid-N-vyli)-CH,CH,-C (=0) -NH-CH,CH>-O- CHCH>-0-CH>CH>-0-CH>CH>-0-CH>CH>-C (=0) -GGFG-NH- CH>-0-CH>-C (=O) — (NH-DX) , (maleimid-N-vyli)-CH>CH>-C (=0) -NH-CH:CH>-O-
CH>CH,-0-CH,CH>-C (=0) -GGFG-NH-CH,CH,-O-CH,-
C (=O) - (NH-DX) ,
(maleimid-N-vyli)-CH>CH>-C (=0) -NH-CH:CH>-O- CHCH>-0-CH>CH>-0-CH>CH>-C (=0) -GGFG-NH-CH,CH>-O0- CH,-C (=0) — (NH-DX) ,
(maleimid-N-yyli)-CH,CH.-C (=0) -NH-CH:CH>-O- CH,CH,-0-CH,CH,-0-CH,CH,-0-CH;CH>-C (=0) -GGFG-NH- CH,CH,-0-CH,-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH,-C (=0)-GGFG- (NH-DX) , (maleimid-N-yyli)-CH,CH.CH,-C (=0) -GGFG- (NH-
DX),
(maleimid-N-vyli) -CH,CH:CH,CH>-C (=0) -GGFG- (NH- DX),
(maleimid-N-yyli)-CH,CH,CH,CH,CH,-C (=0) -GGFG- (NH-DX) ,
(maleimid-N-yyli)-CH,CH,-C (=0)-DGGFG- (NH-DX) , (maleimid-N-yyli)-CH,CH.CH,-C (=0) -DGGFG- (NH- DX),
(maleimid-N-yyli)-CH,CH.CH,CH,-C (=0) -DGGFG- (NH- DX), Ja (maleimid-N-yyli)-CH,CH,CH,CH-CH,-C (=0) -DGGFG- (NH-DX) .
5
4. Patenttivaatimuksen 3 mukainen menetelmä, jossa yhdiste on jokin valittuna seuraavasta ryhmästä: (maleimid-N-yyli)-CH,CH,CH,CH,CH,-C (=0) -GGFG- NH-CH,CH,CH,-C (=O) - (NH-DX) , (maleimid-N-yyli)-CH,CH,CH,CH,CH,-C (=0) -DGGFG- NH-CH,CH,CH,-C (=O) - (NH-DX) , (maleimid-N-yyli)-CH,CH,CH,CH,CH,-C (=0) -GGFG- NH-CH,-0-CH.-C (=0) - (NH-DX) , (maleimid-N-yyli)-CH,CH.-C (=0) -NH-CH:CH>-O-
CH-.CH,-0-CH,CH,-C (=0) -GGFG-NH-CH>CH>CH>-C (=0) - (NH-DX), ja (maleimid-N-yyli)-CH,CH,CH,CH-CH,-C (=0) -DGGFG- (NH-DX) .
5. Patenttivaatimuksen 4 mukainen menetelmä, jossa yhdiste on: (maleimid-N-yyli) -CHCH:CHCH>CH>-C (=0) -GGFG- —NH-CH,CH,CH>-C (=O) - (NH-DX) .
6. Patenttivaatimuksen 4 mukainen menetelmä, jossa yhdiste on: (maleimid-N-yyli) -CHCH:CH>CH>CH>-C (=0) -DGGFG- NH-CH,CH,CH,-C (=O) - (NH-DX) .
7. Patenttivaatimuksen 4 mukainen menetelmä, jossa yhdiste on: (maleimid-N-yyli)-CH,CH,CH,CH,CH,-C (=0) -GGFG- NH-CH>-O-CH>,-C (=0) - (NH-DX) .
8. Patenttivaatimuksen 4 mukainen menetelmä, jossa yhdiste on: (maleimid-N-vyli)-CH>CH>-C (=0) -NH-CH:CH>-O- CH,CH,-0-CH.CH.-C (=0) -GGFG-NH-CH,CH>CH>-C (=O) - (NH-DX) .
9. Patenttivaatimuksen 4 mukainen menetelmä, jossa yhdiste on: (maleimid-N-yyli) -CHCH:CH>CH>CH>-C (=0) -DGGFG- (NH-DX) .
10. Patenttivaatimuksen 1 mukainen menetelmä, jossa vasta-aine-lääkekonjugaatilla on lääke-linkkeri- rakenne, jota edustaa seuraava kaava: - (sukkinimid-3-yyli-N)- (CH)n3-C (=0) -L?-LP-NH- (CH2) n!-La- (CH>) n?-C (=0) - (NH-DX) tai - (sukkinimid-3-yyli-N)-(CH,)n3-C (=O) -L?-1L*- (NH-DX) , joka on konjugoitu anti-HER3-vasta-aineeseen tioeetterisidoksella, joka on muodostettu disulfidi- sidoskohtaan, joka on läsnä anti-HER3-vasta-aineen sa- rana-alueella.
11. Patenttivaatimuksen 5 mukainen menetelmä, jossa vasta-aine-lääkekonjugaatilla on lääke-linkkeri- rakenne, jota edustaa seuraava kaava: - (sukkinimid-3-yyli-N)-CH,CH,CH,CH,CH.-C (=0) - GGFG-NH-CH,CH,CH>-C (=O) - (NH-DX), joka on konjugoitu anti-HER3-vasta-aineeseen tioeetterisidoksella, joka on muodostettu disulfidi- sidoskohtaan, joka on läsnä anti-HER3-vasta-aineen sa- rana-alueella.
12. Patenttivaatimuksen 6 mukainen menetelmä, jossa vasta-aine-lääkekonjugaatilla on lääke-linkkeri- rakenne, jota edustaa seuraava kaava: - (sukkinimid-3-yyli-N)-CH,CH,CH,CH,CH.-C (=0) - DGGFG-NH-CH>CH>CH>-C (=O) - (NH-DX), joka on konjugoitu anti-HER3-vasta-aineeseen tioeetterisidoksella, joka on muodostettu disulfidi- sidoskohtaan, joka on läsnä anti-HER3-vasta-aineen sa- rana-alueella.
13. Patenttivaatimuksen 7 mukainen menetelmä, jossa vasta-aine-lääkekonjugaatilla on lääke-linkkeri- rakenne, jota edustaa seuraava kaava: - (sukkinimid-3-yyli-N)-CH,CH,CH,CH,CH.-C (=0)- GGFG-NH-CH>-O-CH>-C (=0) - (NH-DX), joka on konjugoitu anti-HER3-vasta-aineeseen tioeetterisidoksella, joka on muodostettu disulfidi- sidoskohtaan, joka on läsnä anti-HER3-vasta-aineen sa- rana-alueella.
14. Patenttivaatimuksen 8 mukainen menetelmä, jossa vasta-aine-lääkekonjugaatilla on lääke-linkkeri- rakenne, jota edustaa seuraava kaava: - (sukkinimid-3-yyli-N)-CH,CH,-C (=0) -NH-CH>CH>- O-CHCH>-O0-CH>CH>-C (=0) -GGFG-NH-CH,CH,CH>-C (=O) - (NH-DX) , joka on konjugoitu anti-HER3-vasta-aineeseen tioeetterisidoksella, joka on muodostettu disulfidi- sidoskohtaan, joka on läsnä anti-HER3-vasta-aineen sa- rana-alueella.
15. Patenttivaatimuksen 9 mukainen menetelmä, jossa vasta-aine-lääkekonjugaatilla on lääke-linkkeri- rakenne, jota edustaa seuraava kaava: - (sukkinimid-3-yyli-N)-CH,CH,CH,CH,CH.-C (=0) - DGGFCG- (NH-DX) , joka on konjugoitu anti-HER3-vasta-aineeseen tioeetterisidoksella, joka on muodostettu disulfidi- sidoskohtaan, joka on läsnä anti-HER3-vasta-aineen sa- rana-alueella.
16. Jonkin patenttivaatimuksista 1 - 15 mukai- nen menetelmä, jossa anti-HER3-vasta-aine käsittää Ul- 49:n, Ul-53:n, U1-59:n, Ul-7:n tai Ul-9:n CDRH1- -
CDRH3-alueet ja CDRL1- - CDRL3-alueet vastaavasti ras- kas- ja kevytketjuissa.
17. Jonkin patenttivaatimuksista 1 - 15 mukai- nen menetelmä, jossa anti-HER3-vasta-aine käsittää Ul- 49:n, Ul-53:n, U1-59:n, Ul-7:n tai Ul-9:n raskasketjun variaabelialueen ja kevytketjun variaabelialueen vas- taavasti raskas- ja kevytketjuissa.
18. Jonkin patenttivaatimuksista 1 - 15 mukai- nen menetelmä, jossa anti-HER3-vasta-aine käsittää ami- nohapposekvenssit, joita edustavat sekvenssit SEQ ID nro 42 ja 44, SEO ID nro 54 ja 56, SEO ID nro 70 ja 72, SEO ID nro 92 ja 94 tai SEO ID nro 96 ja 98 vastaavasti raskas- ja kevytketjuissa.
19. Jonkin patenttivaatimuksista 1 - 15 mukai- nen menetelmä, jossa anti-HER3-vasta-aine käsittää ami- nohapposekvenssit, joita edustavat sekvenssit SEO ID nro 583 ja 584 vastaavasti raskas- ja kevytketjuissa.
20. Patenttivaatimuksen 19 mukainen menetelmä, jossa anti-HER3-vasta-aineesta puuttuu lysiinitähde raskasketjun karboksipäässä.
21. Jonkin patenttivaatimuksista 1 - 20 mukai- nen menetelmä, jossa valitun lääke-linkkerirakenteen konjugoitujen yksiköiden keskimääräinen määrä per vasta-aine on alueella, joka on 2 - 8.
22. Jonkin patenttivaatimuksista 1 - 20 mukai- nen menetelmä, jossa valitun lääke-linkkerirakenteen konjugoitujen yksiköiden keskimääräinen määrä per vasta-aine on alueella, joka on 3 - 8.
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