HRP20220215T1 - Inhibitori mcl-1 - Google Patents
Inhibitori mcl-1 Download PDFInfo
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- HRP20220215T1 HRP20220215T1 HRP20220215TT HRP20220215T HRP20220215T1 HR P20220215 T1 HRP20220215 T1 HR P20220215T1 HR P20220215T T HRP20220215T T HR P20220215TT HR P20220215 T HRP20220215 T HR P20220215T HR P20220215 T1 HRP20220215 T1 HR P20220215T1
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- Prior art keywords
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- alkyl
- heteroalkyl
- cycloalkyl
- membered heterocyclyl
- Prior art date
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- 101001056180 Homo sapiens Induced myeloid leukemia cell differentiation protein Mcl-1 Proteins 0.000 title 1
- 102100026539 Induced myeloid leukemia cell differentiation protein Mcl-1 Human genes 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 27
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 25
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 23
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 13
- 150000002431 hydrogen Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 229910003827 NRaRb Inorganic materials 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- -1 -(CH2CH2O)pR7 Chemical group 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/20—[b, f]-condensed
-
- 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
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
Claims (15)
1. Spoj, naznačen time, da je u skladu s Formulom (I):
[image]
u kojoj:
--- je jednostruka ili dvostruka veza:
X je O ili NR7;
R12 je vodik ili -C(O)R1;
R1 je C1-6 alkil, C1-6 haloalkil, C2-6 alkenil, C2-6 alkinil, C3-10 cikloalkil, C6-10 aril, 3-12-člani heterociklil, 5-10-člani heteroaril, -OR7 ili -NR8R9, pri čemu su
navedeni C1-6 alkil, C2-6 alkinil, C3-10 cikloalkil, C6-10 aril, 3-12-člani heterociklil i 5-10-člani heteroaril, opcionalno supstituirani s 1-5 skupina R10;
R2 je vodik, C1-6 alkil, C1-6 heteroalkil, C3-10 cikloalkil ili 3-12-člani heterociklil, gdje su
navedeni C1-6 alkil, C1-6 heteroalkil, C3-10 cikloalkil i 3-12-člani heterociklil, opcionalno supstituirani s 1-5 skupina R10;
R3 i R4 su neovisno vodik, C1-6 alkil, -OR7, C1-6 heteroalkil, -NR8R9, -NR8C(O)R9, -NR8C(O)OR9, C6-10 aril, C3-10 cikloalkil, 5-10-člani heteroaril, 3-12-člani heterociklil, -C(O)R7, -C(O)OR7, -C(O)NR8R9, -OC(O)NR8R9, -CN ili -SO2R7, pri čemu su
navedeni C1-6 alkil, C1-6 heteroalkil, C6-10 aril, C3-10 cikloalkil, 5-10-člani heteroaril i 3-12-člani heterociklil, opcionalno supstituirani s 1-5 skupina R10;
R5 je vodik, C1-6 alkil, -(CH2CH2O)pR7, C1-6 heteroalkil, C6-10 aril, C3-10 cikloalkil, 5-10-člani heteroaril ili 3-12-člani heterociklil, pri čemu su
navedeni C1-6 alkil, C1-6 heteroalkil, C6-10 aril, C3-10 cikloalkil, 5-10-člani heteroaril i 3-12-člani heterociklil, opcionalno supstituirani s 1-5 skupina R10;
R6 je vodik ili halogen;
svaki R7 je neovisno vodik, C1-6 alkil, C3-10 cikloalkil, C1-6 heteroalkil, 3-12-člani heterociklil, C6-10 aril ili 5-10-člani heteroaril, pri čemu su
navedeni C1-6 alkil, C3-10 cikloalkil, C1-6 heteroalkil, 3-12-člani heterociklil, C6-10 aril i 5-10-člani heteroaril, opcionalno supstituirani s 1-5 skupina R10;
svaki R8 i R9 je neovisno vodik, C1-6 alkil, C3-10 cikloalkil, C1-6 heteroalkil, 3-12-člani heterociklil, C6-10 aril ili 5-10-člani heteroaril, ili R8 i R9 zajedno s atomima s kojima su vezani, tvore 3-12-člani heterociklil, pri čemu su
navedeni C1-6 alkil, C3-10 cikloalkil, C1-6 heteroalkil, 3-12-člani heterociklil, C6-10 aril i 5-10-člani heteroaril, opcionalno supstituirani s 1-5 skupina R10;
svaki R10 je neovisno C1-6 alkil, C3-10 cikloalkil, C1-6 heteroalkil, 3-12-člani heterociklil, C6-10 aril, 5-10-člani heteroaril, halogen, okso, -ORa, -C(O)Ra, -C(O)ORa, -C(O)NRaRb, -OC(O)NRaRb, -NRaRb, -NRaC(O)Rb, -NRaC(O)ORb, -S(O)qRa, -S(O)2NRaRb, -NRaS(O)2Rb, -N3, -CN ili NO2, ili dvije skupine R10 tvore staljeni, spiro ili premošteni C3-10 cikloalkil ili 3-12-člani heterociklil, pri čemu je
svaki C1-6 alkil, C1-6 heteroalkil, C2-6 alkinil, C3-10 cikloalkil, C6-10 aril, 3-12-člani heterociklil i 5-10-člani heteroaril, opcionalno supstituiran s 1-5 skupina R20;
svaki Ra i Rb je neovisno vodik, C1-6 alkil, C2-6 alkenil, C3-10 cikloalkil, C1-6 heteroalkil, 3-12-člani heterociklil, C6-10 aril, 5-10-člani heteroaril, ili
Ra i Rb zajedno s atomima s kojima su vezani, tvore 3-12-člani heterociklil, pri čemu je
navedeni C1-6 alkil, C2-6 alkenil, C3-10 cikloalkil, C1-6 heteroalkil, 3-12-člani heterociklil, C6-10 aril, 5-10-člani heteroaril, opcionalno supstituiran s 1-5 skupina R20;
svaki R20 je neovisno C1-6 alkil, C3-10 cikloalkil, C1-6 heteroalkil, 3-12-člani heterociklil, C6-10 aril, 5-10-člani heteroaril, hidroksil, C1-6 alkoksi, amino, -CN, -C(O)H, -C(O)NH2, -C(O)NH(C1-6 alkil), -C(O)N(C1-6 alkil)2, -COOH, -C(O)C1-6 alkil, -C(O)OC1-6 alkil ili halogen;
n je 0, 1 ili 2;
p je 0, 1 ili 2; i
q je 0, 1 ili 2;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema patentnom zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, naznačen time, da je u skladu s Formulom (IV):
[image]
u kojoj: R1 je C3-10 cikloalkil, 3-12-člani heterociklil, C6-10 aril ili 5-10-člani heteroaril;
pri čemu je R1 neovisno opcionalno supstituiran s 1-4 skupine R10;
gdje se svaki R10 neovisno bira od sljedećih: halogen, hidroksil, -CN, C1-6 alkil, C1-6 heteroalkil, C3-10 cikloalkil i 3-12-člani heterociklil;
pri čemu su C1-6 alkil, C1-6 heteroalkil, C3-10 cikloalkil i 3-12-člani heterociklil od R10, neovisno opcionalno supstituirani s 1-4 supstituenta koji se neovisno biraju od halogena, C1-4 alkila, C1-4 haloalkila i C1-4 heteroalkila;
R2 je vodik, C1-6 alkil ili C1-6 heteroalkil;
pri čemu su C1-6 alkil i C1-6 heteroalkil od R2, opcionalno supstituirani s 1-3 supstituenta koji se neovisno biraju od halogena, okso i hidroksila;
R3 i R4 su neovisno vodik, C1-6 alkil, C1-6 heteroalkil, -OR7 ili -SO2R7;
pri čemu su C1-6 alkil i C1-6 heteroalkil od R3 i R4, neovisno opcionalno supstituirani s 1-3 supstituenta koji se neovisno biraju od halogena, okso, C3-6 cikloalkila, 4-6-članog heterociklila, C6-10 arila i 5-10-članog heteroarila;
dok su C3-6 cikloalkil, 4-6-člani heterociklil, C6-10 aril i 5-10-člani heteroaril, neovisno opcionalno supstituirani s 1-3 supstituenta koji se neovisno biraju od halogena, C1-4 alkila i C1-4 heteroalkila;
R5 je vodik, C1-6 alkil ili C1-6 heteroalkil;
pri čemu su C1-6 alkil i C1-6 heteroalkil od R5, opcionalno supstituirani s 1-3 supstituenta koji se neovisno biraju od halogena, okso, C3-6 cikloalkila i 4-6-članog heterociklila; i
R7 je neovisno vodik, C1-6 alkil, C1-6 heteroalkil, C3-10 cikloalkil, 3-10-člani heterociklil, C6-10 aril ili 5-10-člani heteroaril;
pri čemu su C1-6 alkil, C1-6 heteroalkil, C3-10 cikloalkil, 3-10-člani heterociklil, C6-10 aril i 5-10-člani heteroaril od R7, opcionalno supstituirani s 1-4 supstituenta koji se neovisno biraju od halogena, okso, C1-4 alkila, C1-4 haloalkila i C1-4 heteroalkila.
3. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time, da:
R2 je vodik ili C1-3 alkil;
R3 je vodik ili C1-3 alkil;
R4 je vodik;
R5 je C1-3 alkil, gdje je
navedeni C1-3 alkil opcionalno supstituiran s 5-6-članim heterociklilom;
ili njegova farmaceutski prihvatljiva sol.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da:
R2 je vodik, metil ili etil;
R3 je vodik ili metil;
R4 je vodik; i
R5 je vodik, metil,
[image]
ili njegova farmaceutski prihvatljiva sol.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, ili njegova farmaceutski prihvatljiva sol, naznačen time, da R3 je metil.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, ili njegova farmaceutski prihvatljiva sol, naznačen time, da R4 je vodik.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, ili njegova farmaceutski prihvatljiva sol, naznačen time, da R5 je metil.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 7, ili njegova farmaceutski prihvatljiva sol, naznačen time, da R1 je
[image]
supstituiran s dvije skupine koje se biraju od C1-4 alkila i C1-4 alkoksila.
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, ili njegova farmaceutski prihvatljiva sol, naznačen time, da R1 je
[image]
10. Spoj prema bilo kojem od patentnih zahtjeva 1 i 3 do 7, ili njegova farmaceutski prihvatljiva sol, naznačen time, da se R1 bira od:
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11. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time, da se bira od:
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12. Spoj prema bilo kojem od patentnih zahtjeva 1 do 9 i 11, naznačen time, da je:
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ili njegova farmaceutski prihvatljiva sol.
13. Spoj prema bilo kojem od patentnih zahtjeva 1 do 7 i 11, naznačen time, da je:
[image]
ili njegova farmaceutski prihvatljiva sol.
14. Farmaceutski pripravak, naznačen time, da sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 9 i 11 do 13, ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljivo pomoćno sredstvo.
15. Spoj prema bilo kojem od patentnih zahtjeva 1 do 9 i 11 do 13, ili njegova farmaceutski prihvatljiva sol, ili farmaceutski pripravak prema patentnom zahtjevu 14, naznačen time, da je za uporabu u postupku liječenja raka kod pacijenta, pri čemu to obuhvaća davanje pacijentu spoja, njegove farmaceutski prihvatljive soli, ili farmaceutskog pripravka.
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