HRP20231571T1 - Derivati fenil/piridil-nh-fenil/piridil za liječenje infekcija rna virusom - Google Patents

Derivati fenil/piridil-nh-fenil/piridil za liječenje infekcija rna virusom Download PDF

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HRP20231571T1
HRP20231571T1 HRP20231571TT HRP20231571T HRP20231571T1 HR P20231571 T1 HRP20231571 T1 HR P20231571T1 HR P20231571T T HRP20231571T T HR P20231571TT HR P20231571 T HRP20231571 T HR P20231571T HR P20231571 T1 HRP20231571 T1 HR P20231571T1
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Croatia
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pharmaceutically acceptable
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hydrogen atom
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HRP20231571TT
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Didier Scherrer
Jamal Tazi
Florence Mahuteau-Betzer
Romain Najman
Julien Santo
Cécile APOLIT
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Abivax
Cnrs Centre National De La Recherche Scientifique
Universite De Montpellier
Institut Curie
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Publication of HRP20231571T1 publication Critical patent/HRP20231571T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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    • 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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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
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    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
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    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/14—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to a carbon atom of a six-membered aromatic ring
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/80—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring
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Claims (14)

1. Spoj formule (Ic): [image] naznačen time što: prsten [image] i prsten [image] neovisno predstavljaju skupinu fenilen ili piridilen, Z" predstavlja skupinu -CH2- ili skupinu -CO-, Rg i Rh neovisno predstavljaju vodikov atom ili (C1-C4)alkilnu skupinu, X2 predstavlja -CO-NRk- skupinu, pri čemu Rk predstavlja vodikov atom ili metilnu skupinu, -NH-CO-NH- skupinu, -OCH2- skupinu, -CH(OH)- skupinu, -NH-CO- skupinu -O- skupinu, -O-(CH2)s-O-, pri čemu s je 2 ili 3, -CO- skupinu, -SO2-skupinu, dvovalentni 5-eročlani heteroaromatski prsten koji sadrži 1, 2, 3 ili 4 heteroatoma, kao što je triazol, imidazol, tetrazol ili oksadiazol, - NH-SO2-, - NH- skupinu, ili -SO2-NH- skupinu, n je 0, 1, 2 ili 3, m i m' su neovisno 0, 1 ili 2, Y2 predstavlja vodikov atom, halogeni atom, hidroksilnu skupinu, (C1-C4)alkoksi skupinu, [image] pri čemu Rf predstavlja (C1-C4)alkilnu skupinu, cijano skupinu, skupinu [image] , skupinu [image] , pri čemu Rq i R'q neovisno predstavljaju vodikov atom ili metilnu skupinu, skupinu morfolinil, po izboru supstituiranu sa (C1-C4)alkilnom skupinom, skupinu piperazinil, skupinu piperidinil, ili -CR1R2R3 skupinu, pri čemu R1, R2 i R3 neovisno predstavljaju vodikov atom, atom fluora ili (C1-C4)alkilnu skupinu, navedena (C1-C4)alkilna skupina je po izboru supstituirana sa skupinom trifluorometil i/ili po izboru supstituirana sa hidroksilnom skupinom, podrazumijeva se da je ne više od jednog R1, R2 i R3 vodikov atom, ili R1 i R2 tvore zajedno s atomom ugljika koji ih nosi (C3-C8)cikloalkilnu skupinu, navedena (C3-C8)cikloalkilna skupina je po izboru supstituirana s jednom ili dvije (C1-C4)alkilne skupine, halogenim atomom, hidroksi ili (C1-C4)alkoksi skupinom i navedena (C3-C8)cikloalkilna skupina je po izboru prekinuta na navedenom R1 i/ili R2 s jednim ili dva atoma kisika, R i R' neovisno predstavljaju (C1-C4)alkilnu skupinu, po izboru prekinutu sa -SO2- skupinom ili -SO- skupinom, (C3-C6)cikloalkilnu skupinu, trifluorometilnu skupinu, halogeni atom, (C1-C5)alkoksi skupinu, -SO2-NRaRb skupinu, -SO3H skupinu, -OH skupinu, -O-SO2-ORc skupinu, ili -O-P(=O)-(ORc)(ORd) skupinu, Ra, Rb, Rc i Rd neovisno predstavljaju vodikov atom ili (C1-C4)alkilnu skupinu, ili bilo koja od njegovih farmaceutski prihvatljivih soli.
2. Spoj formule (Ic) prema zahtjevu 1, naznačen time što prsten [image] i prsten [image] oba predstavljaju skupinu fenilen ili prsten [image] predstavlja skupinu piridilen i prsten [image] predstavlja skupinu fenilen, ili bilo koja od njegovih farmaceutski prihvatljivih soli.
3. Spoj formule (Ic) prema bilo kojem od zahtjeva 1 do 2, naznačen time što Rg je vodikov atom i Rh predstavlja vodikov atom ili (C1-C4)alkilnu skupinu, kao što je metilna skupina, ili bilo koja od njegovih farmaceutski prihvatljivih soli.
4. Spoj formule (Ic) prema bilo kojem od zahtjeva 1 do 3, naznačen time što X2 predstavlja -CO-NRk- skupinu, pri čemu Rk predstavlja vodikov atom ili metilnu skupinu, -NH-CO- skupinu -O- skupinu, -CO- skupinu, -CH(OH)- skupinu, -SO2-skupinu, -NH- skupinu, dvovalentni 5-eročlani heteroaromatski prsten koji sadrži 1, 2, 3 ili 4 heteroatoma, kao što je triazol, imidazol, tetrazol ili oksadiazol, -NH-SO2-, ili -SO2-NH- skupinu, ili bilo koja od njegovih farmaceutski prihvatljivih soli.
5. Spoj formule (Ic) prema bilo kojem od zahtjeva 1 do 4, naznačen time što Y2 predstavlja vodikov atom, halogeni atom, [image] pri čemu Rf predstavlja (C1-C4)alkilnu skupinu, cijano skupinu, skupinu [image] , pri čemu Rq i R'q neovisno predstavljaju vodikov atom ili metilnu skupinu, skupinu morfolinil, po izboru supstituiranu sa (C1-C4)alkilnom skupinom, skupinu [image] , (C1-C4)alkoksi skupinu, ili -CR1R2R3 skupinu, pri čemu R1, R2 i R3 neovisno predstavljaju vodikov atom, atom fluora ili (C1-C4)alkilnu skupinu, navedena (C1-C4)alkilna skupina je po izboru supstituirana sa skupinom trifluorometil, po izboru supstituiranom sa hidroksilnom skupinom, podrazumijeva se da je ne više od jednog R1, R2 i R3 vodikov atom, ili R1 i R2 tvore zajedno s atomom ugljika koji ih nosi (C3-C8)cikloalkilnu skupinu, navedena (C3-C8)cikloalkilna skupina je po izboru supstituirana s jednom ili dvije (C1-C4)alkilne skupine, halogenim atomom, hidroksi ili (C1-C4)alkoksi skupinom i navedena (C3-C8)cikloalkilna skupina je po izboru prekinuta na navedenom R1 i/ili R2 s jednim ili dva atoma kisika, ili bilo koja od njegovih farmaceutski prihvatljivih soli.
6. Spoj formule (Ic) prema bilo kojem od zahtjeva 1 do 5, naznačen time što R i R' neovisno predstavljaju (C1-C4)alkilnu skupinu, po izboru prekinutu sa -SO2- skupinom ili -SO- skupinom, (C3-C6)cikloalkilnu skupinu, trifluorometilnu skupinu, ili halogeni atom, ili bilo koja od njegovih farmaceutski prihvatljivih soli.
7. Spoj formule (Ic) prema bilo kojem od zahtjeva 1 do 6, naznačen time što prsten [image] i prsten [image] oba predstavljaju skupinu fenilen ili prsten [image] predstavlja piridilen i prsten [image] predstavlja skupinu fenilen, m je 0 ili 1, n je 0 ili 1, X2 predstavlja -CO-NH- skupinu, -CO-N(CH3)- skupinu, -NH-CO- skupinu, -O- skupinu ili -CO- skupinu, -NH-SO2- skupinu, -CH(OH)- skupinu, -SO2-skupinu, dvovalentni triazol, dvovalentni imidazol, dvovalentni tetrazol, dvovalentni oksadiazol, -NH- skupinu, Y2 predstavlja vodik, skupinu morfolinil, po izboru supstituiranu sa (C1-C4)alkilnom skupinom, skupinu [image] , skupinu [image] pri čemu Rq i R'q neovisno predstavljaju vodikov atom ili metilnu skupinu, [image] pri čemu Rf predstavlja (C1-C4)alkilnu skupinu, cijano skupinu, (C1-C4)alkoksi skupinu, ili -CR1R2R3 skupinu, pri čemu R1, R2 i R3 neovisno predstavljaju vodikov atom, atom fluora ili (C1-C4)alkilnu skupinu, navedena (C1-C4)alkilna skupina je po izboru supstituirana sa trifluorometilnom skupinom, po izboru supstituiranom sa hidroksilnom skupinom, podrazumijeva se da je ne više od jednog R1, R2 i R3 vodikov atom, ili R1 i R2 tvore zajedno s atomom ugljika koji ih nosi (C3-C8)cikloalkilnu skupinu, navedena (C3-C8)cikloalkilna skupina je po izboru supstituirana s jednom ili dvije (C1-C4)alkilne skupine, halogenim atomom, hidroksi ili (C1-C4)alkoksi skupinom i navedena (C3-C8)cikloalkilna skupina je po izboru prekinuta na navedenom R1 i/ili R2 s jednim ili dva atoma kisika, i R i R' neovisno predstavljaju (C1-C4)alkilnu skupinu, (C3-C6)cikloalkilnu skupinu, kao što je ciklopropil, trifluorometilnu skupinu, ili halogeni atom, ili bilo koja od njegovih farmaceutski prihvatljivih soli.
8. Spoj formule (Ic) prema bilo kojem od zahtjeva 1 do 7, naznačen time što prsten [image] i prsten [image] oba predstavljaju skupinu fenilen, m je 0, n je 1, X2 predstavlja -CO-NH- skupinu, ili -O- skupinu, Y2 predstavlja -CR1R2R3 skupinu, pri čemu R1, R2 i R3 neovisno predstavljaju vodikov atom, ili (C1-C4)alkilnu skupinu, podrazumijeva se da je ne više od jednog R1, R2 i R3 vodikov atom, kao što je izopropilna skupina, ili R1 i R2 tvore zajedno s atomom ugljika koji ih nosi (C3-C8)cikloalkilnu skupinu, kao što je ciklopropil, i R' predstavlja (C1-C4)alkilnu skupinu, kao što je tertiobutilna skupina, ili (C3-C6)cikloalkilnu skupinu, kao što je ciklopropil, ili bilo koja od njegovih farmaceutski prihvatljivih soli.
9. Spoj formule (Ic) prema zahtjevu 1 naznačen time što je odabran od [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] ili bilo koja njihova farmaceutski prihvatljiva sol.
10. Spoj formule (Ic) prema bilo kojem od zahtjeva 1 do 8 ili bila koja od njegovih farmaceutski prihvatljivih soli, i bilo koji od spojeva (19) do (31) i (91) do (181) kako je definirano u zahtjevu 9 ili bilo koja od njihovih farmaceutski prihvatljivih soli, za upotrebu kao lijek.
11. Spoj formule (Ic) prema bilo kojem od zahtjeva 1 do 8 ili bila koja od njegovih farmaceutski prihvatljivih soli ili spoj prema zahtjevu 10 ili bilo koji od spojeva (19) to (31) i (91) do (181) kako je definirano u zahtjevu 9 ili bilo koja od njihovih farmaceutski prihvatljivih soli za upotrebu u liječenju i/ili prevenciji infekcije RNA virusom uzrokovane RNA virusom koji pripada skupini IV ili V Baltimore klasifikacije.
12. Spoj formule (Ic) za upotrebu prema prethodnom zahtjevu, naznačen time što je infekcija RNA virusom uzrokovana RNA virusom koji pripada grupi IV ili V Baltimore klasifikacije odabrana između RSV, Chikungunya groznice, influence i Denga virusa, a točnije između RSV i Chikungunya groznice.
13. Farmaceutski pripravak koji sadrži najmanje jedan spoj kako je definiran u bilo kojem od zahtjeva 1 do 8 ili bilo koju od njegovih farmaceutski prihvatljivih soli, ili najmanje bilo koji od spojeva (19) do (31) i (91) do (181) kako je definirano u zahtjevu 9 ili bila koja od njihovih farmaceutski prihvatljivih soli i također najmanje jednu farmaceutski prihvatljivu pomoćnu tvar.
14. Postupak sinteze za proizvodnju spoja formule (Ic) kako je definiran u bilo kojem od zahtjeva 1 do 8 ili bilo koje njegove farmaceutski prihvatljive soli ili spoja kako je definiran u zahtjevu 9 ili bilo koje njegove farmaceutski prihvatljive soli, uključujući barem sprezanja spoja formule (IIc) [image] (IIc) sa spojem formule (IIIc) [image] pri čemu su R, R', m, m', prsten [image] , prsten [image] , X2, Y2, Rh, Rg i Z" su kako je definirano u zahtjevu 1, X je atom klora, atom joda ili atom broma, u prisutnosti anorganske baze i difosfina i u prisutnosti organometalnog katalizatora, da se dobije spoj formule (Ic) kako je definiran u bilo kojem od zahtjeva 1 do 8 ili bilo koja od njegovih farmaceutski prihvatljivih soli ili spoj kako je definiran u zahtjevu 9 ili bilo koja od njegovih farmaceutski prihvatljivih soli.
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