HRP20171612T1 - Umrežujuće spojnice i njihova upotreba - Google Patents
Umrežujuće spojnice i njihova upotreba Download PDFInfo
- Publication number
- HRP20171612T1 HRP20171612T1 HRP20171612TT HRP20171612T HRP20171612T1 HR P20171612 T1 HRP20171612 T1 HR P20171612T1 HR P20171612T T HRP20171612T T HR P20171612TT HR P20171612 T HRP20171612 T HR P20171612T HR P20171612 T1 HRP20171612 T1 HR P20171612T1
- Authority
- HR
- Croatia
- Prior art keywords
- disulfide
- antibody
- ester
- group
- compound
- Prior art date
Links
- 239000004971 Cross linker Substances 0.000 title claims 3
- 210000004027 cell Anatomy 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 22
- -1 p-nitrophenyl ester Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 15
- 239000011230 binding agent Substances 0.000 claims 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 10
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical group OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims 10
- 125000005179 haloacetyl group Chemical group 0.000 claims 9
- 150000003568 thioethers Chemical class 0.000 claims 9
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 6
- 125000000524 functional group Chemical group 0.000 claims 6
- 150000007970 thio esters Chemical class 0.000 claims 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 5
- 238000004132 cross linking Methods 0.000 claims 5
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- 150000001408 amides Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- QHSXWDVVFHXHHB-UHFFFAOYSA-N 3-nitro-2-[(3-nitropyridin-2-yl)disulfanyl]pyridine Chemical group [O-][N+](=O)C1=CC=CN=C1SSC1=NC=CC=C1[N+]([O-])=O QHSXWDVVFHXHHB-UHFFFAOYSA-N 0.000 claims 3
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical group C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 claims 3
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- UOWVMDUEMSNCAV-WYENRQIDSA-N rachelmycin Chemical class C1([C@]23C[C@@H]2CN1C(=O)C=1NC=2C(OC)=C(O)C4=C(C=2C=1)CCN4C(=O)C1=CC=2C=4CCN(C=4C(O)=C(C=2N1)OC)C(N)=O)=CC(=O)C1=C3C(C)=CN1 UOWVMDUEMSNCAV-WYENRQIDSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
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- INAUWOVKEZHHDM-PEDBPRJASA-N (7s,9s)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7-[(2r,4s,5s,6s)-5-hydroxy-6-methyl-4-morpholin-4-yloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCOCC1 INAUWOVKEZHHDM-PEDBPRJASA-N 0.000 claims 1
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Classifications
-
- 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
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- 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
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-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/5365—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 ortho- or peri-condensed with heterocyclic ring systems
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Claims (17)
1. Umrežujuća spojnica za dobivanje konjugata između sredstva za vezanje stanica i lijeka, gdje umrežujuću spojnicu prikazuje formula (I)
,
naznačena time što:
Y’ predstavlja funkcionalnu skupinu, koja omogućuje reakcija sa sredstvom za vezanje stanica koje se bira između protutijelo, jednolančano protutijelo ili fragment protutijela koji se veže na ciljanu stanicu, gdje se Y’ bira između N-hidroksisukcinimidnog estera, p-nitrofenilnog estera, dinitrofenilnog estera, pentafluorfenilnog estera, piridil-disulfida, nitropiridil-disulfida, maleimida, halogenacetata ili klorida karboksilne kiseline;
Q predstavlja funkcionalnu skupinu, koja omogućuje povezivanje citotoksičnog lijeka preko disulfidne, tioeterske, tioesterske, peptidne, hidrazonske, esterske, eterske, karbamatne ili amidne veze, gdje se Q bira iz skupine koju čine tiol, disulfid, amino, karboksi, aldehid, maleimido, halogenacetil, hidrazin i hidroksi;
jedan od R1, R2, R3, R4, R9 i R10 je nabijeni supstituent, kojeg se bira između SO3–, X-SO3–, OPO32–, X-OPO32–, N+R11R12R13 i X-N+R11R12R13, a ostalo su H; svaki od I, g i m je 0; n je 1, gdje:
R11, R12 i R13 su isti ili različiti i čine nerazgranati alkil s od 1 do 6 atoma ugljika, ili razgranati ili prstenasti alkil s od 3 do 6 atoma ugljika, gdje X predstavlja fenil ili nerazgranati alkil s od 1 do 6 atoma ugljika, ili razgranati ili prstenasti alkil s od 3 do 6 atoma ugljika; i
Z je odsutan.
2. Upotreba umrežujuće spojnice, naznačena time što je umrežujuća spojnica namijenjena dobivanju spoja u skladu s patentnim zahtjevom 6, gdje umrežujuću spojnicu prikazuje formula (I)
,
gdje:
Y’ predstavlja funkcionalnu skupinu, koja omogućuje reakcija sa sredstvom za vezanje stanica koje se bira između protutijelo, jednolančano protutijelo ili fragment protutijela koji se veže na ciljanu stanicu, gdje je Y’ skupina koja reagira s aminom ili skupina koja reagira s tiolom;
Q predstavlja funkcionalnu skupinu, koja omogućuje povezivanje citotoksičnog lijeka preko disulfidne, tioeterske, tioesterske, peptidne, hidrazonske, esterske, eterske, karbamatne ili amidne veze, gdje se Q bira iz skupine koju čine tiol, disulfid, amino, karboksi, aldehid, maleimido, halogenacetil, hidrazin i hidroksi;
jedan od R1, R2, R3, R4, R9 i R10 je nabijeni supstituent, kojeg se bira između SO3–, X-SO3–, OPO32–, X-OPO32–, N+R11R12R13 i X-N+R11R12R13, a ostalo su H; svaki od I, g i m je 0; n je 1, gdje:
R11, R12 i R13 su isti ili različiti i čine nerazgranati alkil s od 1 do 6 atoma ugljika, ili razgranati ili prstenasti alkil s od 3 do 6 atoma ugljika, gdje X predstavlja fenil ili nerazgranati alkil s od 1 do 6 atoma ugljika, ili razgranati ili prstenasti alkil s od 3 do 6 atoma ugljika; i
Z je odsutan.
3. Upotreba u skladu s patentnim zahtjevom 2, naznačena time što se Y’ bira između N-hidroksisukcinimidnog estera, p-nitrofenilnog estera, dinitrofenilnog estera, pentafluorfenilnog estera, piridil-disulfida, nitropiridil-disulfida, maleimida, halogenacetata ili klorida karboksilne kiseline.
4. Umrežujuća spojnica u skladu s patentnim zahtjevom 1 ili upotreba u skladu s patentnim zahtjevom 2, naznačene time što:
1. Q je disulfidna, maleimido, halogenacetilna skupina, ili N-hidroksisukcinimidni ester, a Y’ je disulfidna, maleimido, halogenacetilna skupina, ili N-hidroksisukcinimidni ester; ili
2. jedan od R1, R2, R3, R4, R9 i R10 je SO3– ili X-SO3–; Q je disulfidna, maleimido ili halogenacetilna skupina; a Y’ je maleimido skupina ili N-hidroksisukcinimidni ester; ili
3. jedan od R1, R2, R3, R4, R9 i R10 je SO3– ili X-SO3–; Q je piridilditio, nitropiridilditio, maleimido ili halogenacetilna skupina; a Y’ je N-hidroksisukcinimidni ester.
5. Umrežujuća spojnica u skladu s patentnim zahtjevom 1 ili upotreba u skladu s patentnim zahtjevom 2, naznačene time što umrežujuću spojnicu prikazuje jedna od sljedećih formula:
i
.
6. Spoj formule koju se bira iz skupine koju čini:
,
naznačen time što:
CB predstavlja sredstvo za vezanje stanica, gdje je sredstvo za vezanje stanica protutijelo, jednolančano protutijelo ili fragment protutijela koji se veže na ciljanu stanicu;
D predstavlja lijek povezan sa sredstvom za vezanje stanica disulfidnom, tioeterskom, tioesterskom, peptidnom, hidrazonskom, esterskom, eterskom, karbamatnom ili amidnom vezom;
jedan od R1, R2, R3, R4, R9 i R10 je nabijeni supstituent, kojeg se bira između SO3–, X-SO3–, OPO32–, X-OPO32–, N+R11R12R13 i X-N+R11R12R13, a ostalo su H; svaki od I, g i m je 0; n je 1; gdje:
R11, R12 i R13 su isti ili različiti i čine nerazgranati alkil s od 1 do 6 atoma ugljika, razgranati ili prstenasti alkil s od 3 do 6 atoma ugljika, gdje X predstavlja fenil ili nerazgranati alkil s od 1 do 6 atoma ugljika, ili razgranati ili prstenasti alkil s od 3 do 6 atoma ugljika;
Z je odsutan;
Y predstavlja karbonilnu, tioetersku, amidnu, disulfidnu ili hidrazonsku skupinu; i
q predstavlja cijeli broj od 1 do 20.
7. Spoj formule koju se bira iz skupine koju čine:
ili
,
naznačen time što:
CB predstavlja sredstvo za vezanje stanica, gdje je sredstvo za vezanje stanica protutijelo ili fragment protutijela koji se veže na ciljanu stanicu;
D predstavlja lijek povezan sa sredstvom za vezanje stanica disulfidnom, tioeterskom, tioesterskom, peptidnom, hidrazonskom, esterskom, eterskom, karbamatnom ili amidnom vezom;
Y’ predstavlja funkcionalnu skupinu, koja omogućuje reakcija sa sredstvom za vezanje stanica, gdje se Y’ bira između N-hidroksisukcinimidnog estera, p-nitrofenilnog estera, dinitrofenilnog estera, pentafluorfenilnog estera, piridil-disulfida, nitropiridil-disulfida, maleimida, halogenacetata ili klorida karboksilne kiseline;
Q predstavlja funkcionalnu skupinu, koja omogućuje povezivanje citotoksičnog lijeka preko disulfidne, tioeterske, tioesterske, peptidne, hidrazonske, esterske, eterske, karbamatne ili amidne veze, gdje se Q bira iz skupine koju čine tiol, disulfid, amino, karboksi, aldehid, maleimido, halogenacetil, hidrazin i hidroksi;
jedan od R1, R2, R3, R4, R9 i R10 je nabijeni supstituent, kojeg se bira između SO3–, X-SO3–, OPO32–, X-OPO32–, N+R11R12R13 i X-N+R11R12R13, a ostalo su H; svaki od I, g i m je 0; n je 1; gdje:
R11, R12 i R13 su isti ili različiti i čine nerazgranati alkil s od 1 do 6 atoma ugljika, razgranati ili prstenasti alkil s od 3 do 6 atoma ugljika, gdje X predstavlja fenil ili nerazgranati alkil s od 1 do 6 atoma ugljika, ili razgranati ili prstenasti alkil s od 3 do 6 atoma ugljika;
Z je odsutan;
Y predstavlja karbonilnu, tioetersku, amidnu, disulfidnu ili hidrazonsku skupinu; i
q predstavlja cijeli broj od 1 do 20.
8. Spoj u skladu s patentnim zahtjevom 7, naznačen time što:
1. kod spoja formule (IV), jedan od R1, R2, R3, R4, R9 i R10 je SO3– ili X-SO3–; a Y’ je maleimido ostatak ili N-hidroksisukcinimidni ester; ili
2. kod spoja formule (IV), Y’ je disulfidna, maleimido, halogenacetilna skupina, ili N-hidroksisukcinimidni ester; ili
3. kod spoja formule (IV), jedan od R1, R2, R3, R4, R9 i R10 je SO3– ili X-SO3–; a Y’ je N-hidroksisukcinimidni ester; ili
4. kod spoja formule (III), jedan od R1, R2, R3, R4, R9 i R10 je SO3– ili X-SO3–; Q je disulfid, maleimid ili halogenacetil ostatak, i Y je tioeter, amid ili disulfid; ili
5. kod spoja formule (III), jedan od R1, R2, R3, R4, R9 i R10 je SO3– ili X-SO3–; Q je piridilditio ili nitropiridilditio skupina, a Y je tioeter, amid ili disulfid.
9. Spoj u skladu s patentnim zahtjevom 6, naznačen time što se lijek bira između maitansinoida, analoga CC-1065, morfolino-doksorubicina, taksana, kalheamicina, auristatina, pirolobenzodiazepinskog dimera, siRNA ili njihove kombinacije, te farmaceutski prihvatljivih soli, kiselina ili derivata bilo kojeg od gore navedenog.
10. Spoj u skladu s patentnim zahtjevom 6, naznačen time što je jedan od R1, R2, R3, R4, R9 i R10 SO3– ili X-SO3–, a lijek je maitansinoid, analog CC-1065 ili pirolobenzodiazepinski dimer, povezan preko disulfidne, tioesterske ili tioeterske veze.
11. Spoj u skladu s patentnim zahtjevom 10, naznačen time što spoj prikazuje sljedeća formula:
,
gdje D’-S-S predstavlja lijek povezan sa sredstvom za vezanje stanica preko disulfidne veze.
12. Spoj u skladu s patentnim zahtjevom 11, naznačen time što je lijek maitansinoid.
13. Spoj u skladu s bilo kojim od patentnih zahtjeva 6 ili 9-12, naznačen time što se protutijelo, jednolančano protutijelo ili fragment veže na ciljane stanice, koje se bira između tumorskih stanica, stanica inficiranih virusom, stanica inficiranih mikroorganizmom, stanica inficiranih parazitom, autoimunih stanica, aktiviranih stanica, mijeloidnih stanica, aktiviranih T-stanica, B-stanica ili melanocita, stanica koje eksprimiraju jedan ili više od IGF-IR, CanAg, EGFR, receptora EphA2, MUC1, MUC 16, VEGF, TF, EpCAM, CD2, CD3, CD4, CD5, CD6, CD11, CD11a, CD18, CD19, CD20, CD22, CD26, CD30, CD33, CD37, CD38, CD40, CD44, CD56, CD79, CD105, CD138, receptora EphA, receptora EphB, EGFr, EGFRvIII, HER2/neu, HER3, mezotelina, kripto, alfavbeta3, integrina, alfavbeta5 integrina, alfavbeta6 integrina, te antigena Apo2 i C242; i stanica koje eksprimiraju receptor inzulinskog čimbenika rasta, receptor epidermnog čimbenika rasta ili folatni receptor, te izborno gdje se tumorske stanice bira između stanica raka dojke, stanica raka prostate, stanica raka jajnika, stanica kolorektalnog raka, stanica raka želuca, raka pločastih stanica, stanica raka malih stanica pluća, te stanica raka testisa.
14. Spoj u skladu s bilo kojim od patentnih zahtjeva 6 ili 9-13, naznačen time što se protutijelo, jednolančano protutijelo ili fragment biraju iz skupine koju čine:
(i) resurfacirano protutijelo, resurfacirano jednolančano protutijelo, ili fragment resurfaciranog protutijela; ili
(ii) monoklonsko protutijelo, jednolančano monoklonsko protutijelo, ili fragment monoklonskog protutijela; ili
(iii) ljudsko protutijelo, humanizirano protutijelo ili resurfacirano protutijelo, humanizirano jednolančano protutijelo, ili fragment humaniziranog protutijela; ili
(iv) kimerno protutijelo, fragment kimernog protutijela; ili
(v) domensko protutijelo, ili fragment domenskog protutijela.
15. Spoj u skladu s patentnim zahtjevom 14, naznačen time što je protutijelo My9-6, B4, C242, N901, DS6, CNTO 95, B-B4, trastuzumab, bivatuzumab, sibrotuzumab, pertuzumab ili rituksimab.
16. Spoj s formulom (II) u skladu s bilo kojim od patentnih zahtjeva 6 ili 9-15, naznačen time što je namijenjen upotrebi u liječenju tumora kod subjekta kojem je potrebno liječenje.
17. Farmaceutski pripravak, naznačen time što sadrži djelotvornu količinu spoja s formulom (II) u skladu s bilo kojim od patentnih zahtjeva 6 ili 9-15, njegove farmaceutski prihvatljive soli ili solvata, kao i farmaceutski prihvatljivu podlogu, razrjeđivač ili pomoćnu tvar.
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US8088387B2 (en) * | 2003-10-10 | 2012-01-03 | Immunogen Inc. | Method of targeting specific cell populations using cell-binding agent maytansinoid conjugates linked via a non-cleavable linker, said conjugates, and methods of making said conjugates |
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- 2019-10-14 US US16/601,065 patent/US11046762B2/en active Active
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2021
- 2021-05-13 IL IL283205A patent/IL283205A/en unknown
- 2021-07-09 JP JP2021114005A patent/JP2021176864A/ja active Pending
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2022
- 2022-12-27 JP JP2022209429A patent/JP2023036868A/ja active Pending
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