HRP20161286T1 - Novi anti-invazivni spojevi - Google Patents

Novi anti-invazivni spojevi Download PDF

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HRP20161286T1
HRP20161286T1 HRP20161286TT HRP20161286T HRP20161286T1 HR P20161286 T1 HRP20161286 T1 HR P20161286T1 HR P20161286T T HRP20161286T T HR P20161286TT HR P20161286 T HRP20161286 T HR P20161286T HR P20161286 T1 HRP20161286 T1 HR P20161286T1
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Croatia
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group
amino
phenyl
pyridin
propyl
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HRP20161286TT
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Pierre Roux
Florence Mahuteau
Romain Najman
Gilles Gadea
Jamal Tazi
Didier Scherrer
Carsten BROCK
Nathalie CAHUZAC
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Abivax
Centre National De La Recherche Scientifique
Institut Curie
Universite De Montpellier
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    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • 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
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Epidemiology (AREA)

Claims (17)

1. Spoj s formulom (I): [image] naznačen time da A i A' neovisno predstavljaju fenilen skupinu ili piridilen skupinu; R2 je vodikov atom ili skupina (C1-C4)alkil; R3 je skupina 2-piridil, skupina 3-piridil, skupina 4-piridil, skupina 2-pirimidinil, skupina 4-pirimidinil ili skupina 5-pirimidinil; R4 je karbonilna skupina ili sulfonilna skupina; i R5 je skupina -NH-(CH2)a-NR6R7 ili skupina 4-metilpiperazinil, pri čemu je a cijeli broj od 1 do 4, R6 i R7 predstavljaju neovisno skupinu (C1-C4)alkil, ili R6 i R7 zajedno s atomom dušika na koji su vezani tvore heterocikličku skupinu koja je odabrana od skupine 4-metilpiperazinil, morfolino skupine, pirolidinil skupine i piperidino skupine; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
2. Spoj s formulom (I) prema zahtjevu 1 naznačen time da A i A' neovisno predstavljaju fenilen skupinu ili piridilen skupinu; R2 je vodikov atom ili metilna skupina; R3 je skupina 2-piridil, skupina 4-piridil ili skupina 4-pirimidinil; R4 je karbonilna skupina ili sulfonilna skupina; i R5 je skupina -NH-(CH2)a-NR6R7 ili skupina 4-metilpiperazinil, pri čemu je a cijeli broj od 2 do 3, R6 i R7 predstavljaju etilnu skupinu, ili R6 i R7 zajedno s atomom dušika na koji su vezani tvore heterocikličku skupinu koja je odabrana između skupine 4-metilpiperazinil, morfolino skupine, pirolidinil skupine i piperidino skupine; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
3. Spoj s formulom (I) prema zahtjevu 1 ili 2 naznačen time da skupina -NH- između A i A' i skupina -R4-R5 su u meta položaju jedan prema drugom s obzirom na A'.
4. Spoj s formulom (I') prema bilo kojem od zahtjeva 1 do 3 [image] naznačen time da X i X' su neovisno CH ili N; R2 je vodikov atom ili metilna skupina; R3 je skupina 2-piridil, skupina 4-piridil ili skupina 4-pirimidinil; R4 je karbonilna skupina ili sulfonilna skupina; i R5 je skupina -NH-(CH2)a-NR6R7 ili skupina 4-metilpiperazinil, pri čemu je a cijeli broj od 2 do 3, R6 i R7 predstavljaju etilnu skupinu, ili R6 i R7 zajedno s atomom dušika na koji su vezani tvore heterocikličku skupina koja je odabrana između skupine 4-metilpiperazinil, morfolino skupine, pirolidinil skupine i piperidino skupine; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
5. Spoj s formulom (Ia) prema bilo kojem od zahtjeva 1 do 4 [image] naznačen time da R2, R3, R4 i R5 su kao što je definirano u bilo kojem od zahtjeva 1, 2 i 4; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
6. Spoj s formulom (Ia) prema bilo kojem od zahtjeva 1 do 5, naznačen time da R4 je karbonil skupina i R2, R3 i R5 su kao što je definirano u bilo kojem od zahtjeva 1, 2 i 4, ili bilo koja od njegovih farmaceutski prihvatljivih soli.
7. Spoj s formulom (Ic) prema bilo kojem od zahtjeva 1 do 4 [image] naznačen time da R2, R3, R4 i R5 su kao što je definirano u bilo kojem od zahtjeva 1, 2 i 4; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
8. Spoj s formulom (Ic) prema zahtjevima 1, 2, 4 i 7, naznačen time da R2 je vodikov atom ili metilna skupina; R3 je skupina 4-piridil ili skupina 4-pirimidinil; R4 je karbonilna skupina; i R5 je skupina -NH-(CH2)a-NR6R7, a je cijeli broj 3, R6 i R7 predstavljaju etilnu skupinu, ili R6 i R7 zajedno s atomom dušika na koji su vezani tvore heterocikličku skupinu koja je skupina 4-metilpiperazinil; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
9. Spoj s formulom (Id) prema bilo kojem od zahtjeva 1 do 4 [image] naznačen time da R2, R3, R4 i R5 su kao što je definirano u bilo kojem od zahtjeva 1 do 3; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
10. Spoj s formulom (Id) prema zahtjevima 1, 2, 3, 4 i 8, naznačen time da R2 je vodikov atom; R3 je skupina 4-piridil; R4 je karbonilna skupina; i R5 je skupina -NH-(CH2)a-NR6R7, a je cijeli broj 3, R6 i R7 predstavljaju etilnu skupinu, ili R6 i R7 zajedno s atomom dušika na koji su vezani tvore heterocikličku skupinu koja je skupina 4-metilpiperazinil; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
11. Spoj s formulom (Ie) prema bilo kojem od zahtjeva 1 do 4 [image] naznačen time da R2, R3, R4 i R5 su kao što je definirano u bilo kojem od zahtjeva 1, 2 i 4; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
12. Spoj s formulom (Ie) prema zahtjevima 1, 2, 3, 4 i 10, naznačen time da R2 je vodikov atom; R3 je skupina 4-piridil; R4 je karbonilna skupina ili sulfonilna skupina; i R5 je -NH-(CH2)a-NR6R7 skupina, a je cijeli broj 3, R6 i R7 predstavljaju etilnu skupinu, ili R6 i R7 zajedno s atomom dušika na koji su vezani tvore heterocikličku skupinu koja je odabrana između skupine 4-metilpiperazinil, morfolino skupine, pirolidinil skupine i piperidino skupine; ili bilo koja od njegovih farmaceutski prihvatljivih soli.
13. Spoj s formulom (I) prema zahtjevu 1 naznačen time da je odabran iz skupa koji čine - (1) N-(3-(dietilamino)propil)-3-((3-(piridin-4-ilkarbamoil)fenil)amino) benzamid - (2) 3-((4-((3-(dietilamino)propil)karbamoil)fenil)amino)-N-(piridin-4-il)benzamid - (3) N-(3-morfolinopropil)-3-((3-(piridin-4-ilkarbamoil)fenil) amino)benzamid - (4) N-(piridin-4-il)-3-((3-((3-(pirolidin-1-il)propil)karbamoil)fenil)amino) benzamid - (5) 3-((3-(N-3-(dietilamino)propil)sulfamoil)fenil)amino)-N-(piridin-4-il)benzamid - (6) N-(3-(4-metilpiperazin-1-il)propil)-3-((3-(piridin-4-ilkarbamoil)fenil) amino)benzamid - (7) N-(3-(piperidin-1-il)propil)-3-((3-(piridin-4-ilkarbamoil)fenil)amino) benzamid - (8) 3-((3-(4-metilpiperazine-1-karbonil)fenil)amino)-N-(piridin-4-il)benzamid - (9) 3-((3-(N-(3-(piperidin-1-il)propil)sulfamoil)fenil)amino)-N-(piridin-4-il) benzamid - (10) 3-((3-(N-(2-(piperidin-1-il)etil)sulfamoil)fenil)amino)-N-(piridin-4-il) benzamid - (11) N-(3-(dietilamino)propil)-3-((3-(piridin-2-ilkarbamoil)fenil)amino) benzamid - (12) 3-((3-(N-(3-morfolinopropil)sulfamoil)fenil)amino)-N-(piridin-4-il)benzamid - (13) N-(3-(dietilamino)propil)-3-((4-(piridin-4-ilkarbamoil)fenil)amino) benzamid - (14) N-(3-morfolinopropil)-3-((4-(piridin-4-ilkarbamoil)fenil)amino) benzamid - (15) 4-((3-(N-(3-morfolinopropil)sulfamoil)fenil)amino)-N-(piridin-4-il)benzamid - (16) N-(piridin-4-il)-4-((3-(N-(2-(pirolidin-1-il)etil)sulfamoil)fenil) amino)benzamid - (17) 3-((3-((3-(dietilamino)propil)karbamoil)fenil)amino)-N-metil-N-(piridin-4-il)benzamid - (18) N-metil-N-(piridin-4-il)-3-((3-((3-(pirolidin-1-il)propil)karbamoil) fenil)amino)benzamid - (19) 3-((3-(N-(3-(dietilamino)propil)sulfamoil)fenil)amino)-N-metil-N-(piridin-4-il)benzamid - (20) N-metil-3-((3-((3-(4-metilpiperazin-1-il)propil)karbamoil)fenil) amino)-N-(piridin-4-il)benzamid - (21) N-metil-3-((3-((3-(piperidin-1-il)propil)karbamoil)fenil)amino)-N-(piridin-4-il)benzamid - (22) N-metil-3-((3-((3-morfolinopropil)karbamoil)fenil)amino)-N-(piridin-4-il)benzamid - (23) N-metil-3-((3-(N-(3-morfolinopropil)sulfamoil)fenil)amino)-N-(piridin-4-il)benzamid - (24) N-metil-3-((3-(N-(3-(piperidin-1-il)propil)sulfamoil)fenil)amino)-N-(piridin-4-il)benzamid - (25) N-(3-(dietilamino)propil)-3-((3-(pirimidin-4-ilkarbamoil)fenil)amino)benzamid - (26) 3-((3-(N-(3-(dietilamino)propil)sulfamoil)fenil)amino)-N-(pirimidin-4-il)benzamid - (27) 3-((3-(N-(3-(piperidin-1-il)propil)sulfamoil)fenil)amino)-N-(pirimidin-4-il)benzamid - (28) N-(pirimidin-4-il)-3-((3-((3-(pirolidin-1-il)propil)karbamoil)fenil) amino)benzamid - (29) N-(3-(piperidin-1-il)propil)-3-((3-(pirimidin-4-ilkarbamoil)fenil) amino)benzamid - (30) N-(3-morfolinopropil)-3-((3-(pirimidin-4-ilkarbamoil)fenil)amino) benzamid - (31) N-(3-(4-metilpiperazin-1-il)propil)-3-((3-(pirimidin-4-ilkarbamoil) fenil)amino)benzamid - (32) N-(3-(dietilamino)propil)-5-((3-(piridin-4-ilkarbamoil)fenil)amino) nikotinamid - (33) N-(3-(dietilamino)propil)-2-((3-(piridin-4-ilkarbamoil)fenil)amino) izonikotinamid - (34) N-(3-(4-metilpiperazin-1-il)propil)-2-((3-(piridin-4-il)karbamoil)-fenil)amino) izonikotinamid - (35) N-(3-(dietilamino)propil)-6-((3-(piridin-4-ilkarbamoil)fenil)amino) pikolinamid - (36) N-(3-(dietilamino)propil)-6-((4-(piridin-4-ilkarbamoil)fenil)amino) pikolinamid - (37) N-(3-(dietilamino)propil)-6-((3-(metil(piridin-4-il)karbamoil)fenil) amino)pikolinamid - (38) N-(3-(dietilamino)propil)-2-((3-(metil(piridin-4-il)karbamoil)fenil) amino)izonikotinamid - (39) 2-((3-(metil(piridin-4-il)karbamoil)fenil)amino)-N-(3-(4-metilpiperazin-1-il)propil)izonikotinamid - (40) N-(3-(dietilamino)propil)-6-((3-(pirimidin-4-ilkarbamoil)fenil)amino) pikolinamid - (41) N-(3-(dietilamino)propil)-2-((3-(pirimidin-4-ilkarbamoil)fenil)amino) izonikotinamid - (42) N-(3-(4-metilpiperazin-1-il)propil)-2-((3-(pirimidin-4-ilkarbamoil)fenil) amino)izonikotinamid - (43) N-(3-(dietilamino)propil)-6-((4-(piridin-4-ilkarbamoil)piridin-2-il)amino)pikolinamid - (44) N-(3-(dietilamino)propil)-2-((4-(piridin-4-ilkarbamoil)piridin-2-il)amino)izonikotinamid - (45) N-(3-(4-metilpiperazin-1-il)propil)-2-((4-(piridin-4-ilkarbamoil)piridin-2-il)amino)izonikotinamid - (46) 2-((3-(N-(3-(dietilamino)propil)sulfamoil)fenil)amino)-N-(piridin-4-il)izonikotinamid - (47) 2-((3-((3-(dietilamino)propil)karbamoil)fenil)amino)-N-(piridin-4-il)izonikotinamid - (48) 2-((3-((3-morfolinopropil)karbamoil)fenil)amino)-N-(piridin-4-il) izonikotinamid - (49) N-(3-(piperidin-1-il)propil)-3-((3-(piridin-4-ilkarbamoil)fenil)amino) benzamid - (50) N-(piridin-4-il)-2-((3-((3-(pirolidin-1-il)propil)karbamoil)fenil) amino)izonikotinamid - (51) 2-((3-((3-(4-metilpiperazin-1-il)propil)karbamoil)fenil)amino)-N-(piridin-4-il)izonikotinamid i njihove farmaceutski prihvatljive soli.
14. Postupak za pripravu spojeva s formulom (I) prema zahtjevu 1 koji sadrži reakciju spoja s formulom (II) [image] naznačen time da R2, R3 i A su kako je definirano u zahtjevu 1, sa spojem s formulom (III) [image] pri čemu X je klorov atom, jodov atom ili bromov atom, i R4, R5 i A' su kako je definirano u zahtjevu 1.
15. Spoj s formulom (I) prema zahtjevima 1 do 13 naznačen time da je za uporabu kao lijek.
16. Spoj s formulom (I) prema zahtjevima 1 do 13 naznačen time da je za uporabu za sprječavanje i/ili inhibiciju i/ili liječenje raka.
17. Farmaceutski pripravak naznačen time da sadrži barem jedan spoj s formulom (I) kako je definirano u zahtjevima 1 do 13 i farmaceutski prihvatljivo pomoćno sredstvo.
HRP20161286TT 2012-09-28 2016-10-06 Novi anti-invazivni spojevi HRP20161286T1 (hr)

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EP12186684.2A EP2712862A1 (en) 2012-09-28 2012-09-28 New anti-invasive compounds
PCT/IB2013/058992 WO2014049578A1 (en) 2012-09-28 2013-09-30 New anti-invasive compounds
EP13812086.0A EP2900635B1 (en) 2012-09-28 2013-09-30 New anti-invasive compounds

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US9969715B2 (en) 2018-05-15
MX366633B (es) 2019-07-17
US10717724B2 (en) 2020-07-21
US11427566B2 (en) 2022-08-30
PT2900635T (pt) 2016-10-25
BR112015006979A2 (pt) 2017-07-04
CA2886804A1 (en) 2014-04-03
KR20150083845A (ko) 2015-07-20
WO2014049578A1 (en) 2014-04-03
AU2013322131B2 (en) 2017-04-13
EP2900635B1 (en) 2016-07-13
ES2598056T3 (es) 2017-01-25
US20200239444A1 (en) 2020-07-30
JP6209215B2 (ja) 2017-10-04
US20150315173A1 (en) 2015-11-05
AU2013322131A1 (en) 2015-04-30
EP2712862A1 (en) 2014-04-02
CA2886804C (en) 2020-09-22
KR102175775B1 (ko) 2020-11-06
DK2900635T3 (en) 2016-10-31
CU20150029A7 (es) 2015-09-29
BR112015006979B1 (pt) 2022-02-22
RU2015115360A (ru) 2016-11-20
RU2641650C2 (ru) 2018-01-19
JP2015531368A (ja) 2015-11-02
CU24282B1 (es) 2017-11-07
HK1213884A1 (zh) 2016-07-15
CN104903293A (zh) 2015-09-09
MX2015003706A (es) 2016-01-14

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